# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2005
data_global

_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Prof Keith Smith'
_publ_contact_author_address     
;
Department of Chemistry
University of Wales - Swansea
Singleton Park
Swansea
SA2 8PP
UNITED KINGDOM
;

_publ_contact_author_email       K.SMITH@SWANSEA.AC.UK

_publ_section_title              
;
Bromination of cis,trans,trans-1,5,9-cyclododecatriene
with bromine; an extensive study
;
loop_
_publ_author_name
'Keith Smith'
'Alex D. Checquer'
'Simon G. Clement'
'Gamal A. El-Hiti'
'Oliver W. Howarth'
;
M.B.Hursthouse
;
'Elfyn Jones'
'Gurvinder S. Kang'
'Chia-Hui Liu'

data_03HUR307
_database_code_depnum_ccdc_archive 'CCDC 217888'

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C12 H18 Br6'
_chemical_formula_weight         641.72
_chemical_melting_point          ?
_chemical_compound_source        ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.676(4)
_cell_length_b                   6.4009(4)
_cell_length_c                   18.702(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.578(8)
_cell_angle_gamma                90.00
_cell_volume                     1732.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.460
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    13.886
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       ?
_diffrn_measurement_method       ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7273
_diffrn_reflns_av_R_equivalents  0.0862
_diffrn_reflns_av_sigmaI/netI    0.1334
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2684
_reflns_number_observed          1967
_reflns_observed_criterion       >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-92 (Sheldrick, 1993)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^
or flagged by the user for potential systematic errors.  Weighted R-factors
wR and all goodnesses of fit S are based on F^2^, conventional R-factors R
are based on F, with F set to zero for negative F^2^. The observed criterion
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      
'calc w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2684
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_obs          0.0451
_refine_ls_wR_factor_all         0.1116
_refine_ls_wR_factor_obs         0.1098
_refine_ls_goodness_of_fit_all   1.001
_refine_ls_goodness_of_fit_obs   1.163
_refine_ls_restrained_S_all      1.001
_refine_ls_restrained_S_obs      1.163
_refine_ls_shift/esd_max         0.002
_refine_ls_shift/esd_mean        0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Br1 Br 0.09005(7) 0.20233(13) 0.01009(5) 0.0224(3) Uani 1 d . .
Br2 Br 0.03592(7) 0.32007(14) -0.17960(5) 0.0269(3) Uani 1 d . .
Br3 Br 0.35120(7) 0.8056(2) -0.17455(6) 0.0310(3) Uani 1 d . .
Br4 Br 0.36083(7) 1.23546(13) -0.05881(6) 0.0282(3) Uani 1 d . .
Br5 Br 0.48245(7) 0.5817(2) 0.15929(6) 0.0291(3) Uani 1 d . .
Br6 Br 0.34749(7) 0.6081(2) 0.27629(6) 0.0294(3) Uani 1 d . .
C1 C 0.1415(6) 0.4504(13) -0.0227(5) 0.023(2) Uani 1 d . .
H1 H 0.1955(6) 0.4045(13) -0.0326(5) 0.027 Uiso 1 calc R .
C2 C 0.0710(6) 0.5387(13) -0.0987(5) 0.020(2) Uani 1 d . .
H2 H 0.0154(6) 0.5775(13) -0.0897(5) 0.024 Uiso 1 calc R .
C3 C 0.1047(7) 0.7318(13) -0.1275(6) 0.025(2) Uani 1 d . .
H3A H 0.1194(7) 0.8393(13) -0.0880(6) 0.030 Uiso 1 calc R .
H3B H 0.0549(7) 0.7839(13) -0.1732(6) 0.030 Uiso 1 calc R .
C4 C 0.1920(6) 0.6930(13) -0.1478(5) 0.021(2) Uani 1 d . .
H4A H 0.2295(6) 0.5842(13) -0.1142(5) 0.025 Uiso 1 calc R .
H4B H 0.1718(6) 0.6432(13) -0.2007(5) 0.025 Uiso 1 calc R .
C5 C 0.2510(6) 0.8862(13) -0.1391(5) 0.018(2) Uani 1 d . .
H5 H 0.2130(6) 0.9938(13) -0.1742(5) 0.022 Uiso 1 calc R .
C6 C 0.2919(6) 0.9772(12) -0.0591(5) 0.021(2) Uani 1 d . .
H6 H 0.2394(6) 1.0201(12) -0.0463(5) 0.026 Uiso 1 calc R .
C7 C 0.3534(6) 0.8382(13) 0.0093(5) 0.020(2) Uani 1 d . .
H7A H 0.3232(6) 0.7046(13) 0.0068(5) 0.024 Uiso 1 calc R .
H7B H 0.4118(6) 0.8125(13) 0.0042(5) 0.024 Uiso 1 calc R .
C8 C 0.3715(6) 0.9371(13) 0.0861(5) 0.021(2) Uani 1 d . .
H8A H 0.3180(6) 1.0214(13) 0.0810(5) 0.026 Uiso 1 calc R .
H8B H 0.4233(6) 1.0319(13) 0.0972(5) 0.026 Uiso 1 calc R .
C9 C 0.3920(6) 0.7962(13) 0.1561(5) 0.021(2) Uani 1 d . .
H9 H 0.4228(6) 0.8852(13) 0.2013(5) 0.025 Uiso 1 calc R .
C10 C 0.3087(6) 0.6994(13) 0.1683(5) 0.021(2) Uani 1 d . .
H10 H 0.2647(6) 0.8137(13) 0.1617(5) 0.025 Uiso 1 calc R .
C11 C 0.2550(7) 0.5268(13) 0.1125(6) 0.027(2) Uani 1 d . .
H11A H 0.2968(7) 0.4532(13) 0.0942(6) 0.032 Uiso 1 calc R .
H11B H 0.2328(7) 0.4275(13) 0.1405(6) 0.032 Uiso 1 calc R .
C12 C 0.1748(6) 0.6051(14) 0.0442(5) 0.025(2) Uani 1 d . .
H12A H 0.1922(6) 0.7343(14) 0.0263(5) 0.030 Uiso 1 calc R .
H12B H 0.1242(6) 0.6360(14) 0.0603(5) 0.030 Uiso 1 calc R .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0242(6) 0.0225(5) 0.0231(6) -0.0005(4) 0.0120(4) -0.0027(4)
Br2 0.0328(6) 0.0246(6) 0.0196(5) -0.0043(4) 0.0059(4) -0.0037(4)
Br3 0.0322(7) 0.0366(6) 0.0348(6) 0.0011(5) 0.0246(5) 0.0034(5)
Br4 0.0247(6) 0.0205(5) 0.0421(7) 0.0072(4) 0.0159(5) -0.0005(4)
Br5 0.0206(6) 0.0426(6) 0.0248(6) 0.0063(5) 0.0095(5) 0.0066(4)
Br6 0.0259(6) 0.0447(6) 0.0181(5) 0.0007(4) 0.0091(4) -0.0036(5)
C1 0.016(5) 0.025(5) 0.028(6) 0.001(4) 0.009(4) -0.006(4)
C2 0.024(6) 0.021(5) 0.013(5) -0.004(4) 0.007(4) 0.001(4)
C3 0.025(6) 0.022(5) 0.025(6) 0.001(4) 0.005(5) -0.005(4)
C4 0.026(6) 0.021(5) 0.018(5) -0.004(4) 0.010(4) 0.001(4)
C5 0.022(6) 0.020(5) 0.019(5) 0.012(4) 0.015(4) 0.009(4)
C6 0.021(6) 0.016(5) 0.036(6) 0.008(4) 0.020(5) 0.004(4)
C7 0.010(5) 0.027(5) 0.027(6) 0.005(4) 0.012(4) 0.005(4)
C8 0.012(5) 0.024(5) 0.026(6) 0.001(4) 0.003(4) -0.005(4)
C9 0.014(5) 0.023(5) 0.022(5) -0.005(4) 0.003(4) 0.003(4)
C10 0.018(5) 0.024(5) 0.015(5) 0.011(4) 0.001(4) 0.002(4)
C11 0.032(6) 0.014(5) 0.030(6) -0.004(4) 0.007(5) -0.006(4)
C12 0.017(6) 0.030(6) 0.027(6) 0.005(4) 0.007(5) 0.001(4)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.982(9) . ?
Br2 C2 1.978(8) . ?
Br3 C5 1.993(9) . ?
Br4 C6 1.974(8) . ?
Br5 C9 1.957(8) . ?
Br6 C10 1.962(8) . ?
C1 C12 1.522(12) . ?
C1 C2 1.534(12) . ?
C2 C3 1.522(12) . ?
C3 C4 1.574(13) . ?
C4 C5 1.515(12) . ?
C5 C6 1.501(12) . ?
C6 C7 1.552(12) . ?
C7 C8 1.494(12) . ?
C8 C9 1.519(12) . ?
C9 C10 1.540(12) . ?
C10 C11 1.530(12) . ?
C11 C12 1.494(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C1 C2 114.8(7) . . ?
C12 C1 Br1 108.6(6) . . ?
C2 C1 Br1 110.3(6) . . ?
C3 C2 C1 113.7(8) . . ?
C3 C2 Br2 109.6(6) . . ?
C1 C2 Br2 109.8(6) . . ?
C2 C3 C4 114.2(7) . . ?
C5 C4 C3 113.4(7) . . ?
C6 C5 C4 115.6(7) . . ?
C6 C5 Br3 110.0(6) . . ?
C4 C5 Br3 106.2(5) . . ?
C5 C6 C7 119.4(7) . . ?
C5 C6 Br4 110.6(6) . . ?
C7 C6 Br4 108.2(6) . . ?
C8 C7 C6 112.2(7) . . ?
C7 C8 C9 118.4(7) . . ?
C8 C9 C10 117.1(7) . . ?
C8 C9 Br5 110.8(6) . . ?
C10 C9 Br5 111.0(6) . . ?
C11 C10 C9 117.7(8) . . ?
C11 C10 Br6 111.0(6) . . ?
C9 C10 Br6 109.1(6) . . ?
C12 C11 C10 113.8(7) . . ?
C11 C12 C1 113.3(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C1 C2 C3 56.2(11) . . . . ?
Br1 C1 C2 C3 179.3(6) . . . . ?
C12 C1 C2 Br2 179.4(6) . . . . ?
Br1 C1 C2 Br2 -57.5(7) . . . . ?
C1 C2 C3 C4 62.7(10) . . . . ?
Br2 C2 C3 C4 -60.6(9) . . . . ?
C2 C3 C4 C5 -152.6(8) . . . . ?
C3 C4 C5 C6 61.5(10) . . . . ?
C3 C4 C5 Br3 -176.2(6) . . . . ?
C4 C5 C6 C7 56.6(11) . . . . ?
Br3 C5 C6 C7 -63.7(9) . . . . ?
C4 C5 C6 Br4 -176.9(6) . . . . ?
Br3 C5 C6 Br4 62.7(6) . . . . ?
C5 C6 C7 C8 -167.8(8) . . . . ?
Br4 C6 C7 C8 64.7(8) . . . . ?
C6 C7 C8 C9 153.6(8) . . . . ?
C7 C8 C9 C10 -82.4(10) . . . . ?
C7 C8 C9 Br5 46.2(10) . . . . ?
C8 C9 C10 C11 71.5(10) . . . . ?
Br5 C9 C10 C11 -57.0(9) . . . . ?
C8 C9 C10 Br6 -160.8(6) . . . . ?
Br5 C9 C10 Br6 70.6(6) . . . . ?
C9 C10 C11 C12 -92.5(10) . . . . ?
Br6 C10 C11 C12 140.8(7) . . . . ?
C10 C11 C12 C1 161.2(8) . . . . ?
C2 C1 C12 C11 -169.7(8) . . . . ?
Br1 C1 C12 C11 66.3(9) . . . . ?

_refine_diff_density_max         1.818
_refine_diff_density_min         -1.017
_refine_diff_density_rms         0.269

data_03HUR315
_database_code_depnum_ccdc_archive 'CCDC 217896'

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C12 H18 Br4'
_chemical_formula_weight         481.90
_chemical_melting_point          ?
_chemical_compound_source        ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   6.5740(2)
_cell_length_b                   31.5300(6)
_cell_length_c                   7.6670(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.030(6)
_cell_angle_gamma                90.00
_cell_volume                     1511.16(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.118
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    10.627
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       ?
_diffrn_measurement_method       ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2544
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0629
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         24.95
_reflns_number_total             1531
_reflns_number_observed          1419
_reflns_observed_criterion       >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-92 (Sheldrick, 1993)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^
or flagged by the user for potential systematic errors.  Weighted R-factors
wR and all goodnesses of fit S are based on F^2^, conventional R-factors R
are based on F, with F set to zero for negative F^2^. The observed criterion
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      
'calc w=1/[\s^2^(Fo^2^)+(0.0568P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_number_reflns         1531
_refine_ls_number_parameters     145
_refine_ls_number_restraints     74
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_obs          0.0396
_refine_ls_wR_factor_all         0.1050
_refine_ls_wR_factor_obs         0.1047
_refine_ls_goodness_of_fit_all   1.101
_refine_ls_goodness_of_fit_obs   1.144
_refine_ls_restrained_S_all      1.082
_refine_ls_restrained_S_obs      1.122
_refine_ls_shift/esd_max         -0.002
_refine_ls_shift/esd_mean        0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Br1 Br 0.3074(2) 0.03975(4) 0.0709(2) 0.0228(3) Uani 1 d . .
Br2 Br 0.8755(2) 0.02142(4) 0.2384(2) 0.0233(3) Uani 1 d . .
Br3 Br 1.2856(2) 0.17388(4) 0.2344(2) 0.0275(4) Uani 1 d . .
Br4 Br 0.8234(2) 0.23351(4) 0.2066(2) 0.0287(4) Uani 1 d . .
C1 C 0.7198(19) 0.1085(4) -0.3251(17) 0.017(3) Uani 1 d U .
H1 H 0.8505(19) 0.0946(4) -0.2833(17) 0.020 Uiso 1 calc R .
C2 C 0.7249(20) 0.1509(4) -0.3332(18) 0.024(3) Uani 1 d U .
H2 H 0.5935(20) 0.1644(4) -0.3799(18) 0.029 Uiso 1 calc R .
C3 C 0.9172(21) 0.1790(4) -0.2757(20) 0.024(3) Uani 1 d U .
H3A H 0.9288(21) 0.1943(4) -0.3819(20) 0.029 Uiso 1 calc R .
H3B H 1.0444(21) 0.1616(4) -0.2293(20) 0.029 Uiso 1 calc R .
C4 C 0.9067(21) 0.2110(4) -0.1267(19) 0.026(3) Uani 1 d U .
H4A H 1.0444(21) 0.2249(4) -0.0797(19) 0.031 Uiso 1 calc R .
H4B H 0.8014(21) 0.2326(4) -0.1825(19) 0.031 Uiso 1 calc R .
C5 C 0.8492(19) 0.1911(4) 0.0337(17) 0.019(3) Uani 1 d U .
H5 H 0.7048(19) 0.1796(4) -0.0198(17) 0.023 Uiso 1 calc R .
C6 C 0.9869(18) 0.1535(4) 0.1217(18) 0.017(3) Uani 1 d U .
H6 H 0.9874(18) 0.1335(4) 0.0237(18) 0.021 Uiso 1 calc R .
C7 C 0.9194(19) 0.1290(4) 0.2658(17) 0.020(3) Uani 1 d U .
H7A H 0.9024(19) 0.1485(4) 0.3582(17) 0.024 Uiso 1 calc R .
H7B H 1.0297(19) 0.1087(4) 0.3258(17) 0.024 Uiso 1 calc R .
C8 C 0.7094(19) 0.1058(4) 0.1781(17) 0.021(3) Uani 1 d U .
H8A H 0.6090(19) 0.1255(4) 0.0993(17) 0.025 Uiso 1 calc R .
H8B H 0.6511(19) 0.0972(4) 0.2745(17) 0.025 Uiso 1 calc R .
C9 C 0.7240(19) 0.0662(4) 0.0641(18) 0.017(3) Uani 1 d U .
H9 H 0.8156(19) 0.0737(4) -0.0106(18) 0.020 Uiso 1 calc R .
C10 C 0.5139(19) 0.0497(4) -0.0666(18) 0.019(3) Uani 1 d U .
H10 H 0.5431(19) 0.0223(4) -0.1144(18) 0.022 Uiso 1 calc R .
C11 C 0.4072(22) 0.0776(4) -0.2279(19) 0.026(3) Uani 1 d U .
H11A H 0.3934(22) 0.1059(4) -0.1824(19) 0.032 Uiso 1 calc R .
H11B H 0.2638(22) 0.0669(4) -0.2858(19) 0.032 Uiso 1 calc R .
C12 C 0.5216(19) 0.0815(4) -0.3776(18) 0.024(3) Uani 1 d U .
H12A H 0.5597(19) 0.0533(4) -0.4072(18) 0.028 Uiso 1 calc R .
H12B H 0.4212(19) 0.0932(4) -0.4879(18) 0.028 Uiso 1 calc R .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0191(7) 0.0231(7) 0.0280(8) 0.0014(6) 0.0103(6) -0.0023(5)
Br2 0.0225(7) 0.0201(7) 0.0276(8) 0.0076(6) 0.0080(6) 0.0011(5)
Br3 0.0185(7) 0.0197(7) 0.0397(9) -0.0031(7) 0.0023(6) -0.0002(5)
Br4 0.0318(9) 0.0216(7) 0.0353(9) -0.0073(6) 0.0140(7) 0.0050(5)
C1 0.015(4) 0.020(5) 0.021(5) 0.002(4) 0.014(4) -0.001(4)
C2 0.029(5) 0.024(5) 0.020(5) 0.002(4) 0.010(4) 0.003(4)
C3 0.028(5) 0.019(5) 0.026(5) 0.006(4) 0.008(4) -0.010(4)
C4 0.026(5) 0.026(5) 0.026(5) 0.003(4) 0.007(4) -0.004(4)
C5 0.021(5) 0.020(5) 0.015(5) -0.001(4) 0.003(4) -0.005(4)
C6 0.022(4) 0.012(4) 0.019(5) -0.004(4) 0.008(4) 0.001(4)
C7 0.025(5) 0.015(4) 0.020(5) 0.002(4) 0.009(4) -0.001(4)
C8 0.023(5) 0.024(5) 0.019(5) -0.004(4) 0.010(4) 0.006(4)
C9 0.019(4) 0.011(4) 0.018(5) 0.003(4) 0.004(4) 0.002(3)
C10 0.019(4) 0.017(4) 0.020(5) -0.001(4) 0.007(4) 0.002(3)
C11 0.025(5) 0.031(5) 0.025(5) 0.003(4) 0.010(4) -0.005(4)
C12 0.022(5) 0.026(5) 0.022(5) 0.001(4) 0.006(4) -0.000(4)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C10 1.985(12) . ?
Br2 C9 1.988(12) . ?
Br3 C6 1.992(12) . ?
Br4 C5 1.927(13) . ?
C1 C2 1.34(2) . ?
C1 C12 1.50(2) . ?
C1 H1 0.93 . ?
C2 C3 1.49(2) . ?
C2 H2 0.93 . ?
C3 C4 1.54(2) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C4 C5 1.53(2) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C5 C6 1.52(2) . ?
C5 H5 0.98 . ?
C6 C7 1.52(2) . ?
C6 H6 0.98 . ?
C7 C8 1.52(2) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.54(2) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 C10 1.53(2) . ?
C9 H9 0.98 . ?
C10 C11 1.50(2) . ?
C10 H10 0.98 . ?
C11 C12 1.56(2) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C12 125.8(12) . . ?
C2 C1 H1 117.1(8) . . ?
C12 C1 H1 117.1(7) . . ?
C1 C2 C3 127.6(12) . . ?
C1 C2 H2 116.2(8) . . ?
C3 C2 H2 116.2(7) . . ?
C2 C3 C4 112.3(10) . . ?
C2 C3 H3A 109.1(7) . . ?
C4 C3 H3A 109.1(7) . . ?
C2 C3 H3B 109.1(7) . . ?
C4 C3 H3B 109.1(7) . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 114.0(10) . . ?
C5 C4 H4A 108.8(7) . . ?
C3 C4 H4A 108.8(7) . . ?
C5 C4 H4B 108.8(7) . . ?
C3 C4 H4B 108.8(7) . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 114.6(10) . . ?
C6 C5 Br4 113.8(9) . . ?
C4 C5 Br4 111.4(9) . . ?
C6 C5 H5 105.3(6) . . ?
C4 C5 H5 105.3(7) . . ?
Br4 C5 H5 105.3(4) . . ?
C5 C6 C7 116.8(10) . . ?
C5 C6 Br3 108.2(8) . . ?
C7 C6 Br3 108.6(8) . . ?
C5 C6 H6 107.7(7) . . ?
C7 C6 H6 107.7(6) . . ?
Br3 C6 H6 107.7(3) . . ?
C6 C7 C8 110.6(10) . . ?
C6 C7 H7A 109.5(6) . . ?
C8 C7 H7A 109.5(6) . . ?
C6 C7 H7B 109.5(6) . . ?
C8 C7 H7B 109.5(6) . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 C9 115.6(10) . . ?
C7 C8 H8A 108.4(6) . . ?
C9 C8 H8A 108.4(6) . . ?
C7 C8 H8B 108.4(7) . . ?
C9 C8 H8B 108.4(7) . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 C8 116.5(10) . . ?
C10 C9 Br2 111.2(8) . . ?
C8 C9 Br2 107.4(8) . . ?
C10 C9 H9 107.1(7) . . ?
C8 C9 H9 107.1(7) . . ?
Br2 C9 H9 107.1(4) . . ?
C11 C10 C9 116.0(10) . . ?
C11 C10 Br1 108.0(8) . . ?
C9 C10 Br1 109.5(9) . . ?
C11 C10 H10 107.7(7) . . ?
C9 C10 H10 107.7(6) . . ?
Br1 C10 H10 107.7(4) . . ?
C10 C11 C12 116.3(11) . . ?
C10 C11 H11A 108.2(7) . . ?
C12 C11 H11A 108.2(7) . . ?
C10 C11 H11B 108.2(7) . . ?
C12 C11 H11B 108.2(7) . . ?
H11A C11 H11B 107.4 . . ?
C1 C12 C11 115.0(11) . . ?
C1 C12 H12A 108.5(7) . . ?
C11 C12 H12A 108.5(7) . . ?
C1 C12 H12B 108.5(7) . . ?
C11 C12 H12B 108.5(7) . . ?
H12A C12 H12B 107.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C1 C2 C3 177.5(12) . . . . ?
C1 C2 C3 C4 -121.3(15) . . . . ?
C2 C3 C4 C5 48.7(16) . . . . ?
C3 C4 C5 C6 52.2(15) . . . . ?
C3 C4 C5 Br4 -176.7(9) . . . . ?
C4 C5 C6 C7 -172.5(11) . . . . ?
Br4 C5 C6 C7 57.5(13) . . . . ?
C4 C5 C6 Br3 64.7(12) . . . . ?
Br4 C5 C6 Br3 -65.2(9) . . . . ?
C5 C6 C7 C8 68.1(14) . . . . ?
Br3 C6 C7 C8 -169.4(8) . . . . ?
C6 C7 C8 C9 73.6(13) . . . . ?
C7 C8 C9 C10 -163.6(11) . . . . ?
C7 C8 C9 Br2 70.9(12) . . . . ?
C8 C9 C10 C11 68.4(15) . . . . ?
Br2 C9 C10 C11 -168.1(9) . . . . ?
C8 C9 C10 Br1 -54.1(12) . . . . ?
Br2 C9 C10 Br1 69.5(9) . . . . ?
C9 C10 C11 C12 69.5(15) . . . . ?
Br1 C10 C11 C12 -167.2(9) . . . . ?
C2 C1 C12 C11 -81.4(17) . . . . ?
C10 C11 C12 C1 -74.2(15) . . . . ?

_refine_diff_density_max         0.836
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.170

data_03HUR316
_database_code_depnum_ccdc_archive 'CCDC 217897'

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C12 H18 Br4'
_chemical_formula_weight         481.90
_chemical_melting_point          ?
_chemical_compound_source        ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/a

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   9.9321(10)
_cell_length_b                   13.1468(5)
_cell_length_c                   11.9463(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.373(8)
_cell_angle_gamma                90.00
_cell_volume                     1471.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.175
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    10.913
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       ?
_diffrn_measurement_method       ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6176
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_sigmaI/netI    0.0811
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         25.04
_reflns_number_total             2243
_reflns_number_observed          1732
_reflns_observed_criterion       >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-92 (Sheldrick, 1993)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^
or flagged by the user for potential systematic errors.  Weighted R-factors
wR and all goodnesses of fit S are based on F^2^, conventional R-factors R
are based on F, with F set to zero for negative F^2^. The observed criterion
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      
'calc w=1/[\s^2^(Fo^2^)+(0.0940P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2243
_refine_ls_number_parameters     145
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_obs          0.0496
_refine_ls_wR_factor_all         0.1349
_refine_ls_wR_factor_obs         0.1320
_refine_ls_goodness_of_fit_all   0.950
_refine_ls_goodness_of_fit_obs   1.067
_refine_ls_restrained_S_all      0.964
_refine_ls_restrained_S_obs      1.079
_refine_ls_shift/esd_max         -0.011
_refine_ls_shift/esd_mean        0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Br1 Br 0.18801(8) 0.55627(6) 0.59897(8) 0.0200(3) Uani 1 d . .
Br2 Br 0.29611(9) 0.56835(7) 0.91128(8) 0.0275(3) Uani 1 d . .
Br3 Br 0.60162(9) 0.23817(6) 0.56648(8) 0.0235(3) Uani 1 d . .
Br4 Br 0.84976(10) 0.27165(7) 0.88320(8) 0.0312(3) Uani 1 d . .
C1 C 0.6402(12) 0.6644(8) 0.8134(12) 0.056(3) Uani 1 d U .
H1A H 0.6725(12) 0.7317(8) 0.8441(12) 0.067 Uiso 1 calc R .
H1B H 0.6868(12) 0.6170(8) 0.8766(12) 0.067 Uiso 1 calc R .
C2 C 0.4790(9) 0.6604(6) 0.7990(8) 0.025(2) Uani 1 d U .
H2A H 0.4609(9) 0.7072(6) 0.8552(8) 0.030 Uiso 1 calc R .
H2B H 0.4242(9) 0.6836(6) 0.7198(8) 0.030 Uiso 1 calc R .
C3 C 0.4267(9) 0.5550(6) 0.8181(8) 0.021(2) Uani 1 d U .
H3 H 0.5105(9) 0.5177(6) 0.8682(8) 0.025 Uiso 1 calc R .
C4 C 0.3569(9) 0.4883(6) 0.7119(8) 0.018(2) Uani 1 d U .
H4 H 0.3236(9) 0.4265(6) 0.7404(8) 0.022 Uiso 1 calc R .
C5 C 0.4534(9) 0.4558(6) 0.6416(8) 0.019(2) Uani 1 d U .
H5A H 0.4813(9) 0.5151(6) 0.6064(8) 0.022 Uiso 1 calc R .
H5B H 0.4014(9) 0.4103(6) 0.5780(8) 0.022 Uiso 1 calc R .
C6 C 0.5882(8) 0.4013(6) 0.7233(7) 0.017(2) Uani 1 d U .
H6A H 0.6410(8) 0.4482(6) 0.7850(7) 0.021 Uiso 1 calc R .
H6B H 0.5589(8) 0.3444(6) 0.7615(7) 0.021 Uiso 1 calc R .
C7 C 0.6862(8) 0.3626(5) 0.6587(7) 0.016(2) Uani 1 d U .
H7 H 0.6884(8) 0.4149(5) 0.6009(7) 0.019 Uiso 1 calc R .
C8 C 0.8404(9) 0.3407(6) 0.7330(8) 0.020(2) Uani 1 d U .
H8 H 0.8756(9) 0.2914(6) 0.6878(8) 0.024 Uiso 1 calc R .
C9 C 0.9423(10) 0.4298(6) 0.7567(10) 0.033(2) Uani 1 d U .
H9A H 0.9526(10) 0.4506(6) 0.6820(10) 0.039 Uiso 1 calc R .
H9B H 1.0351(10) 0.4069(6) 0.8079(10) 0.039 Uiso 1 calc R .
C10 C 0.8961(15) 0.5305(10) 0.8184(15) 0.081(4) Uani 1 d U .
H10 H 0.9204(15) 0.5471(10) 0.8983(15) 0.097 Uiso 1 calc R .
C11 C 0.8190(16) 0.5793(11) 0.7283(14) 0.082(4) Uani 1 d U .
H11 H 0.8375(16) 0.5740(11) 0.6572(14) 0.098 Uiso 1 calc R .
C12 C 0.6922(16) 0.6486(10) 0.7348(13) 0.078(4) Uani 1 d U .
H12A H 0.7168(16) 0.7158(10) 0.7143(13) 0.094 Uiso 1 calc R .
H12B H 0.6116(16) 0.6269(10) 0.6675(13) 0.094 Uiso 1 calc R .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0133(4) 0.0277(5) 0.0180(5) 0.0044(4) 0.0039(4) 0.0042(4)
Br2 0.0284(5) 0.0380(5) 0.0184(6) 0.0017(4) 0.0109(4) 0.0107(4)
Br3 0.0244(5) 0.0250(5) 0.0232(6) -0.0081(4) 0.0106(4) -0.0043(4)
Br4 0.0316(6) 0.0437(6) 0.0178(6) 0.0043(4) 0.0074(5) 0.0161(5)
C1 0.050(5) 0.046(5) 0.079(6) -0.014(4) 0.032(5) -0.003(4)
C2 0.025(4) 0.022(4) 0.030(4) -0.008(3) 0.010(4) -0.001(3)
C3 0.018(4) 0.026(4) 0.020(4) 0.000(3) 0.009(3) 0.008(3)
C4 0.020(4) 0.016(3) 0.019(4) 0.004(3) 0.007(3) 0.006(3)
C5 0.014(3) 0.020(4) 0.024(4) 0.001(3) 0.009(3) -0.004(3)
C6 0.015(3) 0.016(3) 0.022(4) 0.000(3) 0.006(3) -0.001(3)
C7 0.019(4) 0.011(3) 0.018(4) -0.001(3) 0.007(3) -0.004(3)
C8 0.023(4) 0.021(4) 0.019(4) -0.004(3) 0.011(3) 0.001(3)
C9 0.023(4) 0.031(4) 0.047(5) -0.011(4) 0.015(4) -0.004(4)
C10 0.069(6) 0.073(6) 0.090(7) 0.007(5) 0.010(5) -0.016(5)
C11 0.086(6) 0.087(6) 0.075(6) 0.005(5) 0.031(5) -0.032(5)
C12 0.086(6) 0.067(6) 0.078(7) 0.004(5) 0.022(5) -0.013(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.982(8) . ?
Br2 C3 1.978(8) . ?
Br3 C7 1.995(8) . ?
Br4 C8 1.985(8) . ?
C1 C12 1.23(2) . ?
C1 C2 1.553(13) . ?
C2 C3 1.524(11) . ?
C3 C4 1.508(12) . ?
C4 C5 1.530(11) . ?
C5 C6 1.546(12) . ?
C6 C7 1.518(10) . ?
C7 C8 1.522(12) . ?
C8 C9 1.512(12) . ?
C9 C10 1.65(2) . ?
C10 C11 1.27(2) . ?
C11 C12 1.58(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C1 C2 126.0(13) . . ?
C3 C2 C1 113.8(7) . . ?
C4 C3 C2 119.2(7) . . ?
C4 C3 Br2 108.7(5) . . ?
C2 C3 Br2 108.8(5) . . ?
C3 C4 C5 115.3(7) . . ?
C3 C4 Br1 111.1(5) . . ?
C5 C4 Br1 107.2(6) . . ?
C4 C5 C6 110.6(7) . . ?
C7 C6 C5 113.7(7) . . ?
C6 C7 C8 117.2(7) . . ?
C6 C7 Br3 109.4(5) . . ?
C8 C7 Br3 109.0(5) . . ?
C9 C8 C7 116.4(7) . . ?
C9 C8 Br4 111.0(6) . . ?
C7 C8 Br4 110.5(5) . . ?
C8 C9 C10 115.9(8) . . ?
C11 C10 C9 101.9(15) . . ?
C10 C11 C12 121.2(15) . . ?
C1 C12 C11 132.8(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C1 C2 C3 87.9(16) . . . . ?
C1 C2 C3 C4 -96.2(10) . . . . ?
C1 C2 C3 Br2 138.5(7) . . . . ?
C2 C3 C4 C5 64.3(10) . . . . ?
Br2 C3 C4 C5 -170.3(5) . . . . ?
C2 C3 C4 Br1 -57.8(8) . . . . ?
Br2 C3 C4 Br1 67.6(6) . . . . ?
C3 C4 C5 C6 56.1(9) . . . . ?
Br1 C4 C5 C6 -179.7(5) . . . . ?
C4 C5 C6 C7 177.4(6) . . . . ?
C5 C6 C7 C8 160.0(7) . . . . ?
C5 C6 C7 Br3 -75.2(7) . . . . ?
C6 C7 C8 C9 -85.9(9) . . . . ?
Br3 C7 C8 C9 149.1(6) . . . . ?
C6 C7 C8 Br4 41.8(8) . . . . ?
Br3 C7 C8 Br4 -83.2(5) . . . . ?
C7 C8 C9 C10 55.2(12) . . . . ?
Br4 C8 C9 C10 -72.2(10) . . . . ?
C8 C9 C10 C11 -87.7(13) . . . . ?
C9 C10 C11 C12 149.7(12) . . . . ?
C2 C1 C12 C11 -130.6(16) . . . . ?
C10 C11 C12 C1 -4.7(26) . . . . ?

_refine_diff_density_max         2.762
_refine_diff_density_min         -1.153
_refine_diff_density_rms         0.212

data_03HUR317
_database_code_depnum_ccdc_archive 'CCDC 217898'

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C12 H18 Br4'
_chemical_formula_weight         481.90
_chemical_melting_point          ?
_chemical_compound_source        ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.4559(14)
_cell_length_b                   7.4771(13)
_cell_length_c                   17.7504(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.342(7)
_cell_angle_gamma                90.00
_cell_volume                     1520.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.106
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    10.565
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       ?
_diffrn_measurement_method       ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5014
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_sigmaI/netI    0.0915
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         24.95
_reflns_number_total             2240
_reflns_number_observed          1670
_reflns_observed_criterion       >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-92 (Sheldrick, 1993)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^
or flagged by the user for potential systematic errors.  Weighted R-factors
wR and all goodnesses of fit S are based on F^2^, conventional R-factors R
are based on F, with F set to zero for negative F^2^. The observed criterion
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      
'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2240
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_obs          0.0442
_refine_ls_wR_factor_all         0.1089
_refine_ls_wR_factor_obs         0.1075
_refine_ls_goodness_of_fit_all   0.967
_refine_ls_goodness_of_fit_obs   1.117
_refine_ls_restrained_S_all      0.967
_refine_ls_restrained_S_obs      1.117
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Br1 Br 0.87985(6) 0.17068(10) 0.70152(4) 0.0274(2) Uani 1 d . .
Br2 Br 0.56391(6) 0.22878(9) 0.69655(4) 0.0268(2) Uani 1 d . .
Br3 Br 0.50886(6) 0.25544(10) 0.41339(5) 0.0311(3) Uani 1 d . .
Br4 Br 0.76711(7) 0.24833(10) 0.30366(4) 0.0360(3) Uani 1 d . .
C1 C 0.7152(5) 0.4420(9) 0.3713(4) 0.019(2) Uani 1 d . .
H1 H 0.6559(5) 0.5133(9) 0.3443(4) 0.023 Uiso 1 calc R .
C2 C 0.6608(5) 0.3631(8) 0.4411(4) 0.0171(15) Uani 1 d . .
H2 H 0.6450(5) 0.4631(8) 0.4750(4) 0.021 Uiso 1 calc R .
C3 C 0.7339(6) 0.2300(8) 0.4856(4) 0.018(2) Uani 1 d . .
H3A H 0.8106(6) 0.2815(8) 0.4948(4) 0.022 Uiso 1 calc R .
H3B H 0.7440(6) 0.1241(8) 0.4548(4) 0.022 Uiso 1 calc R .
C4 C 0.6841(6) 0.1723(9) 0.5616(4) 0.024(2) Uani 1 d . .
H4A H 0.6062(6) 0.1252(9) 0.5522(4) 0.028 Uiso 1 calc R .
H4B H 0.7318(6) 0.0749(9) 0.5813(4) 0.028 Uiso 1 calc R .
C5 C 0.6768(5) 0.3136(9) 0.6219(4) 0.019(2) Uani 1 d . .
H5 H 0.6418(5) 0.4193(9) 0.5978(4) 0.023 Uiso 1 calc R .
C6 C 0.7851(5) 0.3755(8) 0.6619(4) 0.019(2) Uani 1 d . .
H6 H 0.7600(5) 0.4434(8) 0.7059(4) 0.023 Uiso 1 calc R .
C7 C 0.8689(5) 0.4976(9) 0.6192(4) 0.021(2) Uani 1 d . .
H7A H 0.9371(5) 0.5209(9) 0.6511(4) 0.025 Uiso 1 calc R .
H7B H 0.8948(5) 0.4352(9) 0.5747(4) 0.025 Uiso 1 calc R .
C8 C 0.8150(5) 0.6757(8) 0.5951(4) 0.0152(15) Uani 1 d . .
H8A H 0.7435(5) 0.6536(8) 0.5663(4) 0.018 Uiso 1 calc R .
H8B H 0.7954(5) 0.7438(8) 0.6396(4) 0.018 Uiso 1 calc R .
C9 C 0.8964(6) 0.7824(8) 0.5485(4) 0.023(2) Uani 1 d . .
H9 H 0.9609(6) 0.8331(8) 0.5731(4) 0.027 Uiso 1 calc R .
C10 C 0.8847(6) 0.8112(9) 0.4751(4) 0.024(2) Uani 1 d . .
H10 H 0.9413(6) 0.8813(9) 0.4527(4) 0.029 Uiso 1 calc R .
C11 C 0.7882(6) 0.7408(9) 0.4248(4) 0.022(2) Uani 1 d . .
H11A H 0.7710(6) 0.8273(9) 0.3853(4) 0.027 Uiso 1 calc R .
H11B H 0.7183(6) 0.7258(9) 0.4540(4) 0.027 Uiso 1 calc R .
C12 C 0.8200(5) 0.5613(9) 0.3888(4) 0.020(2) Uani 1 d . .
H12A H 0.8606(5) 0.5843(9) 0.3424(4) 0.024 Uiso 1 calc R .
H12B H 0.8734(5) 0.4979(9) 0.4226(4) 0.024 Uiso 1 calc R .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0249(5) 0.0262(4) 0.0311(5) 0.0100(4) -0.0003(3) 0.0029(3)
Br2 0.0230(5) 0.0312(5) 0.0264(5) 0.0054(3) 0.0071(3) -0.0068(3)
Br3 0.0207(5) 0.0290(5) 0.0433(5) 0.0037(4) -0.0067(3) -0.0066(3)
Br4 0.0543(6) 0.0309(5) 0.0231(5) -0.0098(4) 0.0090(4) 0.0004(4)
C1 0.021(4) 0.016(4) 0.021(4) 0.002(3) 0.005(3) 0.004(3)
C2 0.016(4) 0.012(4) 0.023(4) -0.003(3) -0.002(3) -0.001(3)
C3 0.016(4) 0.017(4) 0.022(4) -0.001(3) 0.002(3) 0.004(3)
C4 0.032(4) 0.014(4) 0.025(4) 0.002(3) 0.003(3) -0.005(3)
C5 0.022(4) 0.016(4) 0.020(4) 0.011(3) 0.008(3) -0.003(3)
C6 0.016(4) 0.014(4) 0.026(4) 0.007(3) -0.000(3) 0.007(3)
C7 0.014(4) 0.016(4) 0.033(5) -0.000(3) 0.005(3) -0.000(3)
C8 0.014(4) 0.016(4) 0.016(4) 0.001(3) 0.000(3) -0.001(3)
C9 0.021(4) 0.013(4) 0.034(5) -0.005(3) 0.004(3) -0.003(3)
C10 0.022(4) 0.015(4) 0.037(5) -0.003(3) 0.009(3) -0.007(3)
C11 0.029(4) 0.017(4) 0.021(4) 0.008(3) -0.002(3) 0.003(3)
C12 0.018(4) 0.018(4) 0.025(4) 0.004(3) 0.003(3) 0.000(3)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C6 1.996(6) . ?
Br2 C5 1.977(6) . ?
Br3 C2 1.969(6) . ?
Br4 C1 1.981(6) . ?
C1 C2 1.519(9) . ?
C1 C12 1.522(9) . ?
C2 C3 1.511(9) . ?
C3 C4 1.538(9) . ?
C4 C5 1.509(10) . ?
C5 C6 1.489(9) . ?
C6 C7 1.537(8) . ?
C7 C8 1.524(9) . ?
C8 C9 1.492(9) . ?
C9 C10 1.324(10) . ?
C10 C11 1.500(10) . ?
C11 C12 1.534(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C12 113.5(6) . . ?
C2 C1 Br4 110.2(4) . . ?
C12 C1 Br4 107.8(4) . . ?
C3 C2 C1 116.7(5) . . ?
C3 C2 Br3 109.7(4) . . ?
C1 C2 Br3 109.4(4) . . ?
C2 C3 C4 115.5(5) . . ?
C5 C4 C3 117.0(6) . . ?
C6 C5 C4 119.8(5) . . ?
C6 C5 Br2 109.4(4) . . ?
C4 C5 Br2 107.4(4) . . ?
C5 C6 C7 118.2(6) . . ?
C5 C6 Br1 111.7(4) . . ?
C7 C6 Br1 106.8(4) . . ?
C8 C7 C6 113.8(5) . . ?
C9 C8 C7 111.6(5) . . ?
C10 C9 C8 125.6(7) . . ?
C9 C10 C11 125.8(6) . . ?
C10 C11 C12 112.1(5) . . ?
C1 C12 C11 113.8(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C1 C2 C3 -66.7(7) . . . . ?
Br4 C1 C2 C3 54.3(7) . . . . ?
C12 C1 C2 Br3 168.1(4) . . . . ?
Br4 C1 C2 Br3 -71.0(4) . . . . ?
C1 C2 C3 C4 171.8(6) . . . . ?
Br3 C2 C3 C4 -63.1(7) . . . . ?
C2 C3 C4 C5 -66.1(8) . . . . ?
C3 C4 C5 C6 -73.7(8) . . . . ?
C3 C4 C5 Br2 160.9(5) . . . . ?
C4 C5 C6 C7 73.7(8) . . . . ?
Br2 C5 C6 C7 -161.8(4) . . . . ?
C4 C5 C6 Br1 -50.8(7) . . . . ?
Br2 C5 C6 Br1 73.7(5) . . . . ?
C5 C6 C7 C8 61.9(8) . . . . ?
Br1 C6 C7 C8 -171.2(5) . . . . ?
C6 C7 C8 C9 -175.2(6) . . . . ?
C7 C8 C9 C10 108.0(8) . . . . ?
C8 C9 C10 C11 -0.6(11) . . . . ?
C9 C10 C11 C12 -92.2(8) . . . . ?
C2 C1 C12 C11 -71.5(7) . . . . ?
Br4 C1 C12 C11 166.2(5) . . . . ?
C10 C11 C12 C1 151.1(6) . . . . ?

_refine_diff_density_max         1.062
_refine_diff_density_min         -0.910
_refine_diff_density_rms         0.218

data_compound_03HUR967
_database_code_depnum_ccdc_archive 'CCDC 260841'

_audit_creation_method           'manually at CCDC'

_chemical_name_systematic        
;

;
_chemical_name_common            ?
_chemical_formula_sum            C12H18Br2
_chemical_formula_moiety         ?
_chemical_formula_weight         322.08
_chemical_melting_point          ?

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/a
_symmetry_Int_Tables_number      ?

loop_
_symmetry_equiv_pos_as_xyz
?
?
?

_cell_length_a                   7.733
_cell_length_b                   15.842
_cell_length_c                   10.62
_cell_angle_alpha                90
_cell_angle_beta                 102.83
_cell_angle_gamma                90
_cell_volume                     1268.53
_cell_formula_units_Z            4

_exptl_crystal_density_diffrn    1.68
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_special_details           
;
?
;
_exptl_absorpt_correction_type   ?
_exptl_absorpt_coefficient_mu    62.94
_exptl_crystal_F_000             640

_diffrn_ambient_temperature      293
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo k alpha'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_number            9725
_diffrn_reflns_theta_max         23
_diffrn_reflns_av_R_equivalents  ?

_reflns_number_total             9725
_reflns_observed_criterion       Fo>3sigma(Fo)
_reflns_number_gt                2475

_refine_ls_R_factor_gt           0.079
_refine_ls_wR_factor_ref         0.076
_refine_ls_number_reflns         2475
_refine_ls_hydrogen_treatment    ?
_refine_ls_number_parameters     145
_refine_ls_number_restraints     ?

_refine_special_details          
;
?
;

_refine_diff_density_max         ?
_refine_diff_density_min         ?

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
Br1 0.0210,2 0.6514,1 0.8705,1
Br2 0.0292,2 0.6344,1 0.5328,1
C1 0.0857,11 0.5521,5 0.7773,8
C2 0.1905,12 0.5801,5 0.6802,8
C3 0.3486,11 0.6357,5 0.7273,8
C4 0.4922,12 0.6270,7 0.6499,10
C5 0.5817,12 0.5417,7 0.6595,10
C6 0.5979,12 0.4860,7 0.7483,10
C7 0.6818,13 0.4012,7 0.7518,10
C8 0.5484,13 0.3284,6 0.7530,10
C9 0.4905,13 0.3224,5 0.8776,9
C10 0.3486,11 0.3532,6 0.9064,9
C11 0.2099,11 0.4040,5 0.8196,9
C12 0.1896,12 0.4911,5 0.8795,8
H11 -0.0390,77 0.5278,37 0.7165,56
H21 0.2166,81 0.5392,40 0.6502,59
H31 0.3071,11 0.6930,5 0.7206,8
H32 0.3995,11 0.6227,5 0.8161,8
H41 0.4394,12 0.6379,7 0.5607,10
H42 0.5823,12 0.6683,7 0.6809,10
H51 0.6308,12 0.5256,7 0.5876,10
H61 0.5513,12 0.5015,7 0.8217,10
H71 0.7316,13 0.3958,7 0.6771,10
H72 0.7748,13 0.3979,7 0.8284,10
H81 0.6075,13 0.2768,6 0.7405,10
H82 0.4462,13 0.3357,6 0.6838,10
H91 0.5679,13 0.2919,5 0.9456,9
H101 0.3305,11 0.3409,6 0.9911,9
H111 0.2431,11 0.4121,5 0.7385,9
H112 0.0982,11 0.3750,5 0.8053,9
H121 0.1277,12 0.4845,5 0.9479,8
H122 0.3050,12 0.5144,5 0.9137,8

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 Br1 1.981,9
C2 Br2 1.970,10
C2 C1 1.512,14
C12 C1 1.540,13
C3 C2 1.501,13
C4 C3 1.527,14
C5 C4 1.512,16
C6 C5 1.277,14
C7 C6 1.488,14
C8 C7 1.550,15
C9 C8 1.491,14
C10 C9 1.298,13
C11 C10 1.486,12
C12 C11 1.542,14

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
? ? ? ? ? ? ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
? ? ? ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
? ? ? ? ?

data_05sjc00001
_database_code_depnum_ccdc_archive 'CCDC 261191'

_audit_creation_date             2005-01-18T23:04:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_sum            'C14 H21 Br6 N'
_chemical_formula_weight         682.78

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2529(7)
_cell_length_b                   13.9866(17)
_cell_length_c                   14.4984(13)
_cell_angle_alpha                75.851(7)
_cell_angle_beta                 79.144(7)
_cell_angle_gamma                83.639(8)
_cell_volume                     1975.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8853
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    2.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1288
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    12.189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 9.091
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_standards_number         none
_diffrn_standards_decay_%        negligible
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_number            39119
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_full        27.5
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             9016
_reflns_number_gt                7371
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_cell_refinement       'DENZO, COLLECT'
_computing_data_reduction        'DENZO, COLLECT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+7.3754P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         9016
_refine_ls_number_parameters     381
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1201
_refine_ls_wR_factor_gt          0.1124
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.166
_refine_diff_density_min         -1.923
_refine_diff_density_rms         0.255

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6416(5) -0.0167(4) 0.2221(4) 0.0118(11) Uani 1 1 d . . .
H1 H 0.5985 -0.0595 0.2837 0.014 Uiso 1 1 calc R . .
C2 C 0.6374(5) 0.0870(4) 0.2389(4) 0.0109(11) Uani 1 1 d . . .
H2 H 0.6967 0.086 0.2865 0.013 Uiso 1 1 calc R . .
C3 C 0.4984(6) 0.1280(4) 0.2764(4) 0.0119(11) Uani 1 1 d . . .
H3A H 0.4373 0.1236 0.2325 0.014 Uiso 1 1 calc R . .
H3B H 0.5019 0.1987 0.2753 0.014 Uiso 1 1 calc R . .
C4 C 0.4420(5) 0.0730(4) 0.3797(4) 0.0119(11) Uani 1 1 d . . .
H4A H 0.4583 0.0008 0.3856 0.014 Uiso 1 1 calc R . .
H4B H 0.4882 0.0914 0.4263 0.014 Uiso 1 1 calc R . .
C5 C 0.2925(5) 0.0990(4) 0.4035(4) 0.0107(11) Uani 1 1 d U . .
H5 H 0.2763 0.1724 0.3844 0.013 Uiso 1 1 calc R . .
C6 C 0.2128(5) 0.0531(4) 0.3499(4) 0.0093(10) Uani 1 1 d . . .
H6 H 0.2567 0.0668 0.2807 0.011 Uiso 1 1 calc R . .
C7 C 0.2021(6) -0.0579(4) 0.3834(4) 0.0118(11) Uani 1 1 d . . .
H7A H 0.133 -0.0715 0.4418 0.014 Uiso 1 1 calc R . .
H7B H 0.2879 -0.0889 0.4019 0.014 Uiso 1 1 calc R . .
C8 C 0.1678(6) -0.1067(4) 0.3083(4) 0.0125(11) Uani 1 1 d . . .
H8A H 0.0833 -0.075 0.2879 0.015 Uiso 1 1 calc R . .
H8B H 0.1546 -0.1774 0.3376 0.015 Uiso 1 1 calc R . .
C9 C 0.2785(5) -0.0975(4) 0.2196(4) 0.0100(11) Uani 1 1 d . . .
H9 H 0.3 -0.0266 0.2005 0.012 Uiso 1 1 calc R . .
C10 C 0.4083(6) -0.1576(4) 0.2361(4) 0.0122(11) Uani 1 1 d . . .
H10 H 0.4324 -0.1444 0.2953 0.015 Uiso 1 1 calc R . .
C11 C 0.5267(6) -0.1330(4) 0.1553(4) 0.0159(12) Uani 1 1 d . . .
H11A H 0.503 -0.1394 0.0941 0.019 Uiso 1 1 calc R . .
H11B H 0.6026 -0.1813 0.1696 0.019 Uiso 1 1 calc R . .
C12 C 0.5700(5) -0.0278(4) 0.1425(4) 0.0112(11) Uani 1 1 d . . .
H12A H 0.6297 -0.0096 0.0797 0.013 Uiso 1 1 calc R . .
H12B H 0.4903 0.019 0.1407 0.013 Uiso 1 1 calc R . .
C13 C 0.7615(5) 0.6362(4) 0.3862(4) 0.0111(11) Uani 1 1 d . . .
H13 H 0.7571 0.638 0.3174 0.013 Uiso 1 1 calc R . .
C14 C 0.8936(6) 0.6751(4) 0.3878(4) 0.0130(11) Uani 1 1 d . . .
H14 H 0.8935 0.7456 0.3511 0.016 Uiso 1 1 calc R . .
C15 C 1.0147(6) 0.6189(4) 0.3421(4) 0.0156(12) Uani 1 1 d . . .
H15A H 1.0109 0.5476 0.3728 0.019 Uiso 1 1 calc R . .
H15B H 1.0963 0.6414 0.3551 0.019 Uiso 1 1 calc R . .
C16 C 1.0242(6) 0.6332(4) 0.2327(4) 0.0152(12) Uani 1 1 d . . .
H16A H 1.0523 0.7003 0.2 0.018 Uiso 1 1 calc R . .
H16B H 0.9353 0.6276 0.218 0.018 Uiso 1 1 calc R . .
C17 C 1.1241(6) 0.5559(4) 0.1935(4) 0.0129(11) Uani 1 1 d . . .
H17 H 1.2058 0.5503 0.2234 0.016 Uiso 1 1 calc R . .
C18 C 1.0694(5) 0.4544(4) 0.2187(4) 0.0120(11) Uani 1 1 d . . .
H18 H 1.0328 0.4399 0.2893 0.014 Uiso 1 1 calc R . .
C19 C 0.9573(6) 0.4430(4) 0.1673(4) 0.0138(12) Uani 1 1 d . . .
H19A H 0.9965 0.4323 0.1025 0.017 Uiso 1 1 calc R . .
H19B H 0.9002 0.5053 0.1584 0.017 Uiso 1 1 calc R . .
C20 C 0.8704(6) 0.3576(4) 0.2211(4) 0.0110(11) Uani 1 1 d . . .
H20A H 0.8068 0.3505 0.1799 0.013 Uiso 1 1 calc R . .
H20B H 0.928 0.2955 0.2317 0.013 Uiso 1 1 calc R . .
C21 C 0.7925(6) 0.3709(4) 0.3182(4) 0.0132(11) Uani 1 1 d . . .
H21 H 0.8587 0.386 0.3543 0.016 Uiso 1 1 calc R . .
C22 C 0.6863(6) 0.4550(4) 0.3144(4) 0.0134(12) Uani 1 1 d . . .
H22 H 0.7269 0.5144 0.2693 0.016 Uiso 1 1 calc R . .
C23 C 0.6320(6) 0.4833(4) 0.4098(4) 0.0156(12) Uani 1 1 d . . .
H23A H 0.6035 0.4235 0.4592 0.019 Uiso 1 1 calc R . .
H23B H 0.5528 0.5301 0.4023 0.019 Uiso 1 1 calc R . .
C24 C 0.7354(6) 0.5311(4) 0.4447(4) 0.0148(12) Uani 1 1 d . . .
H24A H 0.7043 0.5328 0.5133 0.018 Uiso 1 1 calc R . .
H24B H 0.8201 0.4896 0.441 0.018 Uiso 1 1 calc R . .
C25 C 0.1986(7) 0.1534(5) 0.0678(5) 0.0212(14) Uani 1 1 d . . .
C26 C 0.0665(8) 0.1704(7) 0.0395(7) 0.043(2) Uani 1 1 d . . .
H26A H -0.002 0.1592 0.0974 0.064 Uiso 1 1 calc R . .
H26B H 0.0582 0.1248 -0.0004 0.064 Uiso 1 1 calc R . .
H26C H 0.055 0.2387 0.0025 0.064 Uiso 1 1 calc R . .
C27 C 0.6569(6) 0.6438(5) 0.0754(5) 0.0207(14) Uani 1 1 d . . .
C28 C 0.5497(7) 0.6369(6) 0.0257(5) 0.0296(16) Uani 1 1 d . . .
H28A H 0.4685 0.6215 0.0728 0.044 Uiso 1 1 calc R . .
H28B H 0.5738 0.5844 -0.0098 0.044 Uiso 1 1 calc R . .
H28C H 0.5344 0.7 -0.0197 0.044 Uiso 1 1 calc R . .
N1 N 0.2984(6) 0.1410(4) 0.0898(4) 0.0259(13) Uani 1 1 d . . .
N2 N 0.7390(6) 0.6497(4) 0.1156(4) 0.0247(12) Uani 1 1 d . . .
Br1 Br 0.82900(6) -0.06859(4) 0.19730(4) 0.01698(14) Uani 1 1 d . . .
Br2 Br 0.70287(6) 0.18028(4) 0.11748(4) 0.01384(13) Uani 1 1 d . . .
Br3 Br 0.23257(6) 0.05589(4) 0.54319(4) 0.01301(13) Uani 1 1 d . . .
Br4 Br 0.03173(5) 0.11766(4) 0.35430(4) 0.01451(13) Uani 1 1 d . . .
Br5 Br 0.21031(6) -0.12327(5) 0.11151(4) 0.01879(14) Uani 1 1 d . . .
Br6 Br 0.38377(6) -0.30045(4) 0.26327(5) 0.01895(14) Uani 1 1 d . . .
Br7 Br 0.61334(6) 0.72515(4) 0.43199(5) 0.01822(14) Uani 1 1 d . . .
Br8 Br 0.91539(6) 0.67097(5) 0.52037(4) 0.01926(14) Uani 1 1 d . . .
Br9 Br 1.17508(6) 0.60090(5) 0.05355(4) 0.01880(14) Uani 1 1 d . . .
Br10 Br 1.21528(6) 0.35413(4) 0.19965(5) 0.01992(14) Uani 1 1 d . . .
Br11 Br 0.72079(6) 0.24533(4) 0.39336(4) 0.01555(13) Uani 1 1 d . . .
Br12 Br 0.53437(6) 0.42786(4) 0.26064(5) 0.02041(14) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.012(3) 0.015(3) 0.008(3) -0.001(2) -0.003(2) -0.001(2)
C2 0.012(3) 0.018(3) 0.003(2) -0.003(2) 0.001(2) -0.004(2)
C3 0.018(3) 0.012(3) 0.005(3) -0.001(2) -0.001(2) -0.001(2)
C4 0.015(3) 0.018(3) 0.003(3) -0.002(2) -0.005(2) -0.001(2)
C5 0.0118(13) 0.0110(13) 0.0096(14) -0.0029(9) -0.0015(9) -0.0009(9)
C6 0.014(3) 0.012(3) 0.001(2) -0.001(2) -0.002(2) 0.003(2)
C7 0.017(3) 0.015(3) 0.003(2) -0.002(2) 0.002(2) -0.004(2)
C8 0.015(3) 0.017(3) 0.009(3) -0.007(2) -0.004(2) -0.004(2)
C9 0.013(3) 0.015(3) 0.005(3) -0.005(2) -0.005(2) -0.002(2)
C10 0.019(3) 0.004(2) 0.014(3) -0.001(2) -0.005(2) -0.001(2)
C11 0.022(3) 0.015(3) 0.011(3) -0.008(2) 0.004(2) -0.005(2)
C12 0.014(3) 0.016(3) 0.005(3) -0.005(2) 0.000(2) -0.005(2)
C13 0.018(3) 0.009(3) 0.007(3) -0.002(2) -0.002(2) 0.001(2)
C14 0.021(3) 0.014(3) 0.006(3) -0.002(2) -0.006(2) -0.002(2)
C15 0.017(3) 0.016(3) 0.016(3) -0.005(2) -0.006(2) -0.002(2)
C16 0.027(3) 0.009(3) 0.010(3) -0.005(2) -0.001(2) -0.001(2)
C17 0.015(3) 0.019(3) 0.003(3) -0.001(2) 0.004(2) -0.004(2)
C18 0.013(3) 0.009(3) 0.012(3) -0.001(2) -0.002(2) 0.003(2)
C19 0.015(3) 0.019(3) 0.008(3) -0.002(2) -0.001(2) -0.003(2)
C20 0.017(3) 0.013(3) 0.004(3) -0.006(2) 0.000(2) -0.002(2)
C21 0.016(3) 0.010(3) 0.013(3) 0.000(2) -0.004(2) -0.004(2)
C22 0.015(3) 0.015(3) 0.009(3) 0.001(2) -0.002(2) -0.004(2)
C23 0.017(3) 0.009(3) 0.017(3) 0.000(2) 0.004(2) -0.005(2)
C24 0.024(3) 0.011(3) 0.007(3) 0.001(2) 0.001(2) -0.002(2)
C25 0.030(4) 0.017(3) 0.014(3) -0.002(2) 0.000(3) 0.001(3)
C26 0.028(4) 0.048(5) 0.051(6) -0.008(4) -0.012(4) 0.001(3)
C27 0.026(3) 0.016(3) 0.014(3) 0.005(2) 0.000(3) 0.001(2)
C28 0.027(4) 0.039(4) 0.026(4) -0.009(3) -0.009(3) -0.005(3)
N1 0.033(3) 0.022(3) 0.023(3) 0.002(2) -0.015(3) 0.000(2)
N2 0.027(3) 0.021(3) 0.026(3) 0.000(2) -0.013(3) 0.004(2)
Br1 0.0155(3) 0.0205(3) 0.0142(3) -0.0043(2) -0.0028(2) 0.0033(2)
Br2 0.0201(3) 0.0142(3) 0.0056(3) -0.0002(2) 0.0018(2) -0.0060(2)
Br3 0.0196(3) 0.0174(3) 0.0019(2) -0.0019(2) -0.0003(2) -0.0040(2)
Br4 0.0136(3) 0.0152(3) 0.0134(3) -0.0006(2) -0.0033(2) 0.0008(2)
Br5 0.0277(3) 0.0244(3) 0.0080(3) -0.0064(2) -0.0064(2) -0.0056(2)
Br6 0.0241(3) 0.0102(3) 0.0224(3) -0.0033(2) -0.0030(2) -0.0035(2)
Br7 0.0196(3) 0.0145(3) 0.0215(3) -0.0072(2) -0.0034(2) 0.0013(2)
Br8 0.0311(3) 0.0204(3) 0.0104(3) -0.0083(2) -0.0121(2) 0.0068(2)
Br9 0.0253(3) 0.0219(3) 0.0064(3) 0.0011(2) 0.0023(2) -0.0078(2)
Br10 0.0195(3) 0.0182(3) 0.0196(3) -0.0030(2) -0.0014(2) 0.0030(2)
Br11 0.0189(3) 0.0104(3) 0.0138(3) 0.0021(2) 0.0001(2) -0.0015(2)
Br12 0.0220(3) 0.0163(3) 0.0265(3) -0.0050(3) -0.0135(3) 0.0001(2)

#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.523(8) . ?
C1 C12 1.526(8) . ?
C1 Br1 1.976(5) . ?
C1 H1 1 . ?
C2 C3 1.527(8) . ?
C2 Br2 1.969(5) . ?
C2 H2 1 . ?
C3 C4 1.542(7) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.530(7) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 C6 1.511(8) . ?
C5 Br3 1.965(6) . ?
C5 H5 1 . ?
C6 C7 1.519(8) . ?
C6 Br4 1.970(5) . ?
C6 H6 1 . ?
C7 C8 1.528(8) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C9 1.536(8) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.519(7) . ?
C9 Br5 1.954(5) . ?
C9 H9 1 . ?
C10 C11 1.525(8) . ?
C10 Br6 1.975(5) . ?
C10 H10 1 . ?
C11 C12 1.541(8) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 C14 1.521(8) . ?
C13 C24 1.531(8) . ?
C13 Br7 1.975(5) . ?
C13 H13 1 . ?
C14 C15 1.525(8) . ?
C14 Br8 1.963(6) . ?
C14 H14 1 . ?
C15 C16 1.535(8) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C17 1.541(8) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 C18 1.519(8) . ?
C17 Br9 1.959(5) . ?
C17 H17 1 . ?
C18 C19 1.525(8) . ?
C18 Br10 1.962(5) . ?
C18 H18 1 . ?
C19 C20 1.533(8) . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 C21 1.525(8) . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C21 C22 1.510(8) . ?
C21 Br11 1.965(5) . ?
C21 H21 1 . ?
C22 C23 1.520(8) . ?
C22 Br12 1.978(6) . ?
C22 H22 1 . ?
C23 C24 1.534(8) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C25 N1 1.111(9) . ?
C25 C26 1.467(10) . ?
C26 H26A 0.98 . ?
C26 H26B 0.98 . ?
C26 H26C 0.98 . ?
C27 N2 1.131(9) . ?
C27 C28 1.447(10) . ?
C28 H28A 0.98 . ?
C28 H28B 0.98 . ?
C28 H28C 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C12 116.4(5) . . ?
C2 C1 Br1 109.3(4) . . ?
C12 C1 Br1 109.5(4) . . ?
C2 C1 H1 107.1 . . ?
C12 C1 H1 107.1 . . ?
Br1 C1 H1 107.1 . . ?
C1 C2 C3 114.2(5) . . ?
C1 C2 Br2 110.2(4) . . ?
C3 C2 Br2 106.7(4) . . ?
C1 C2 H2 108.6 . . ?
C3 C2 H2 108.6 . . ?
Br2 C2 H2 108.6 . . ?
C2 C3 C4 113.2(5) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 110.6(4) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C6 C5 C4 112.3(5) . . ?
C6 C5 Br3 110.0(4) . . ?
C4 C5 Br3 109.5(4) . . ?
C6 C5 H5 108.3 . . ?
C4 C5 H5 108.3 . . ?
Br3 C5 H5 108.3 . . ?
C5 C6 C7 116.3(4) . . ?
C5 C6 Br4 110.0(4) . . ?
C7 C6 Br4 108.5(4) . . ?
C5 C6 H6 107.2 . . ?
C7 C6 H6 107.2 . . ?
Br4 C6 H6 107.2 . . ?
C6 C7 C8 114.4(5) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C9 111.3(4) . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108 . . ?
C10 C9 C8 115.6(5) . . ?
C10 C9 Br5 112.0(4) . . ?
C8 C9 Br5 109.8(4) . . ?
C10 C9 H9 106.2 . . ?
C8 C9 H9 106.2 . . ?
Br5 C9 H9 106.2 . . ?
C9 C10 C11 115.7(5) . . ?
C9 C10 Br6 110.6(4) . . ?
C11 C10 Br6 109.0(4) . . ?
C9 C10 H10 107 . . ?
C11 C10 H10 107 . . ?
Br6 C10 H10 107 . . ?
C10 C11 C12 112.5(5) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C1 C12 C11 113.7(5) . . ?
C1 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C1 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C24 117.0(5) . . ?
C14 C13 Br7 109.7(4) . . ?
C24 C13 Br7 107.4(4) . . ?
C14 C13 H13 107.4 . . ?
C24 C13 H13 107.4 . . ?
Br7 C13 H13 107.4 . . ?
C13 C14 C15 113.9(5) . . ?
C13 C14 Br8 110.9(4) . . ?
C15 C14 Br8 107.8(4) . . ?
C13 C14 H14 108 . . ?
C15 C14 H14 108 . . ?
Br8 C14 H14 108 . . ?
C14 C15 C16 113.2(5) . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 111.6(5) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108 . . ?
C18 C17 C16 112.3(4) . . ?
C18 C17 Br9 110.4(4) . . ?
C16 C17 Br9 109.7(4) . . ?
C18 C17 H17 108.1 . . ?
C16 C17 H17 108.1 . . ?
Br9 C17 H17 108.1 . . ?
C17 C18 C19 116.5(5) . . ?
C17 C18 Br10 109.7(4) . . ?
C19 C18 Br10 109.9(4) . . ?
C17 C18 H18 106.7 . . ?
C19 C18 H18 106.7 . . ?
Br10 C18 H18 106.7 . . ?
C18 C19 C20 113.9(5) . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 113.9(5) . . ?
C21 C20 H20A 108.8 . . ?
C19 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C22 C21 C20 115.9(5) . . ?
C22 C21 Br11 111.5(4) . . ?
C20 C21 Br11 109.9(4) . . ?
C22 C21 H21 106.3 . . ?
C20 C21 H21 106.3 . . ?
Br11 C21 H21 106.3 . . ?
C21 C22 C23 115.6(5) . . ?
C21 C22 Br12 111.5(4) . . ?
C23 C22 Br12 108.1(4) . . ?
C21 C22 H22 107.1 . . ?
C23 C22 H22 107.1 . . ?
Br12 C22 H22 107.1 . . ?
C22 C23 C24 112.1(5) . . ?
C22 C23 H23A 109.2 . . ?
C24 C23 H23A 109.2 . . ?
C22 C23 H23B 109.2 . . ?
C24 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C13 C24 C23 113.3(5) . . ?
C13 C24 H24A 108.9 . . ?
C23 C24 H24A 108.9 . . ?
C13 C24 H24B 108.9 . . ?
C23 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
N1 C25 C26 179.4(8) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N2 C27 C28 178.8(8) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?


data_compound_TBCD-5
_database_code_depnum_ccdc_archive 'CCDC 261487'

_audit_creation_method           'manually at CCDC'

_chemical_name_systematic        
;

;
_chemical_name_common            ?
_chemical_formula_sum            'C12 H18 Br4'
_chemical_formula_moiety         ?
_chemical_formula_weight         481.89
_chemical_melting_point          ?

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_Int_Tables_number      ?

loop_
_symmetry_equiv_pos_as_xyz
'0.5+x, 0.5-y, 0.5-z'
'-x, 0.5+y, 0.5-z'
'0.5-x, -y, 0.5+z'

_cell_length_a                   17.163(2)
_cell_length_b                   12.517(1)
_cell_length_c                   14.250(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3061.32
_cell_formula_units_Z            8

_exptl_crystal_density_diffrn    2.09
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_special_details           
;
?
;
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_coefficient_mu    103.95
_exptl_crystal_F_000             1840

_diffrn_ambient_temperature      219
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Mok\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_number            3112
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_av_R_equivalents  ?

_reflns_number_total             2691
_reflns_observed_criterion       Fo>3\s(Fo)
_reflns_number_gt                1125

_refine_ls_R_factor_gt           0.068
_refine_ls_wR_factor_ref         0.087
_refine_ls_number_reflns         1125
_refine_ls_hydrogen_treatment    ?
_refine_ls_number_parameters     166
_refine_ls_number_restraints     ?

_refine_special_details          
;
?
;

_refine_diff_density_max         ?
_refine_diff_density_min         ?

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
Br1 0.1878(1) -0.1269(2) 0.0790(2)
Br2 0.3293(1) 0.0619(2) 0.1312(2)
Br3 -0.0187(1) 0.0709(2) 0.1435(2)
Br4 -0.0458(2) 0.3566(2) 0.1628(2)
C1 0.1952(12) 0.0141(15) 0.0190(13)
C2 0.2240(11) 0.0972(16) 0.0861(14)
C3 0.1715(12) 0.1270(18) 0.1678(15)
C4 0.1112(12) 0.2124(16) 0.1438(14)
C5 0.0404(11) 0.1826(15) 0.0811(13)
C6 -0.0094(12) 0.2746(15) 0.0539(13)
C7 0.0269(13) 0.3529(17) -0.0138(15)
C8 0.0558(15) 0.3049(21) -0.1076(16)
C9 0.1337(11) 0.2536(18) -0.1020(14)
C10 0.1548(12) 0.1596(17) -0.1353(14)
C11 0.2354(14) 0.1100(20) -0.1289(18)
C12 0.2368(12) 0.0050(18) -0.0747(15)
H11 0.1387(80) 0.0154(107) 0.0128(90)
H21 0.2429(91) 0.1493(139) 0.0462(108)
H31 0.1468(77) 0.0723(113) 0.1857(92)
H32 0.2012(67) 0.1581(92) 0.2365(84)
H41 0.0854(68) 0.2096(92) 0.2078(96)
H42 0.1392(96) 0.2789(141) 0.1258(108)
H51 0.0501(194) 0.1542(288) 0.0232(255)
H61 -0.0211(107) 0.4058(144) -0.0276(276)
H72 0.0850(82) 0.3830(108) 0.0029(98)
H81 0.0549(104) 0.3788(141) -0.1600(118)
H82 0.0208(79) 0.2639(101) -0.1092(81)
H91 0.1791(118) 0.2978(147) -0.0589(143)
H101 0.1158(102) 0.1158(132) -0.1754(107)
H111 0.2781(93) 0.1588(133) -0.0833(108)
H112 0.2592(157) 0.0997(207) -0.1847(166)
H121 0.3054(72) -0.0015(95) -0.0704(88)
H122 0.2198(125) -0.0364(182) -0.1169(133)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 Br1 1.964(1)
C5 Br3 1.943(1)
C2 Br2 1.969(22)
C8 Br4 1.963(21)
C2 C1 1.497(28)
C12 C1 1.519(31)
C3 C2 1.519(29)
C4 C3 1.527(30)
C5 C4 1.554(30)
C6 C5 1.486(27)
C7 C6 1.509(29)
C8 C7 1.547(33)
C9 C8 1.485(31)
C10 C9 1.318(30)
C11 C10 1.519(34)
C12 C11 1.525(34)

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
? ? ? ? ? ? ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
? ? ? ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
? ? ? ? ?

#END


#END

data_compound_hbcd-1
_database_code_depnum_ccdc_archive 'CCDC 261488'

_audit_creation_method           'manually at CCDC'

_chemical_name_systematic        
;

;
_chemical_name_common            ?
_chemical_formula_sum            'C12 H18 Br6'
_chemical_formula_moiety         ?
_chemical_formula_weight         641.73
_chemical_melting_point          ?

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_Int_Tables_number      61

loop_
_symmetry_equiv_pos_as_xyz
'0.5+x, 0.5-y, 0.5-z'
'-x, 0.5+y, 0.5-z'
'0.5-x, -y, 0.5+z'

_cell_length_a                   11.670(2)
_cell_length_b                   28.998(6)
_cell_length_c                   10.483(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3547.52(6)
_cell_formula_units_Z            8

_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_special_details           
;
?
;
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_coefficient_mu    133.01
_exptl_crystal_F_000             2336

_diffrn_ambient_temperature      219.0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_number            3613
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_av_R_equivalents  ?

_reflns_number_total             1740
_reflns_observed_criterion       Fo>3\s(Fo)
_reflns_number_gt                1358

_refine_ls_R_factor_gt           0.054
_refine_ls_wR_factor_ref         0.072
_refine_ls_number_reflns         1358
_refine_ls_hydrogen_treatment    ?
_refine_ls_number_parameters     103
_refine_ls_number_restraints     ?

_refine_special_details          
;
?
;

_refine_diff_density_max         ?
_refine_diff_density_min         ?

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
BR1 0.07002 0.01497 0.33659
BR2 0.35612 -0.00438 0.42888
BR3 0.11110 -0.15643 0.86825
BR4 0.28357 -0.23608 0.68592
BR5 -0.10747 -0.12676 0.44005
BR6 -0.05473 -0.17649 0.14518
C1 0.13170 -0.04637 0.39416
C2 0.22274 -0.03678 0.49775
C3 0.26023 -0.07979 0.56725
C4 0.16524 -0.09696 0.66145
C5 0.20645 -0.14350 0.71714
C6 0.19378 -0.18475 0.62060
C7 0.06958 -0.19921 0.59112
C8 0.05341 -0.20200 0.44179
C9 0.04050 -0.15269 0.39414
C10 0.06725 -0.14726 0.25078
C11 0.07375 -0.09517 0.20237
C12 0.17816 -0.07166 0.27795

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 2.012
Br2 C2 1.956
Br3 C5 1.972
Br4 C6 1.945
Br5 C9 1.944
Br6 C10 1.993
C1 C2 1.544
C1 C12 1.522
C2 C3 1.509
C3 C4 1.566
C4 C5 1.547
C5 C6 1.574
C6 C7 1.540
C7 C8 1.579
C8 C9 1.522
C9 C10 1.543
C10 C11 1.595
C11 C12 1.605

#END