Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2003


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

loop_
_publ_author_name
'Francois Diederich'
'Corinne Boudon'
'Jean-Paul Gisselbrecht'
'Robin Gist'
'Maurice Gross'
'Masahiro Irie'
;
T.Kawai
;
'Atsushi Kishioka'
'Paul Seiler'

_publ_contact_author_name        'Prof Francois Diederich'
_publ_contact_author_address     
;
Laboratorium fur Organische Chemie
ETH Hoenggerberg
ETH Hoengerberg, HCI
Zuerich
8093
SWITZERLAND
;

_publ_contact_author_email       DIEDERICH@ORG.CHEM.ETHZ.CH

_publ_section_title              
;
Donor-substituted cyanoethynylethenes: powerful 
chromophores for opto-electronic applications
;

data_moon3_D_02
_database_code_CSD               207516
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H10 N4'
_chemical_formula_sum            'C15 H10 N4'
_chemical_formula_weight         246.27
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_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                   7.014(1)
_cell_length_b                   7.085(1)
_cell_length_c                   14.149(2)
_cell_angle_alpha                77.79(2)
_cell_angle_beta                 89.21(1)
_cell_angle_gamma                77.40(2)
_cell_volume                     670.28(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    243(2)
_cell_measurement_reflns_used    18
_cell_measurement_theta_min      18.80
_cell_measurement_theta_max      27.10
_exptl_crystal_description       'Cut fragment'
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_type   non
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      243(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'NONIUS CAD4'
_diffrn_measurement_method       \q/\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  '167 min.'
_diffrn_standards_decay_%        0.800
_diffrn_reflns_number            2922
_diffrn_reflns_av_R_equivalents  0.008
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         74.87
_reflns_number_total             2631
_reflns_number_gt                2304
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CAD4 VMS-software (Nonius, 1989)'
_computing_cell_refinement       'CAD4 VMS-software (Nonius, 1989)'
_computing_data_reduction        'MOLEN VMS-software (Nonius, 1990)'
_computing_structure_solution    'SIR92 (Altomare et al.,1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Johnson,1976)'
_computing_publication_material  SHELXL97
_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     
'w=1/[\s^2^(Fo^2^)+(0.0940P)^2^+0.1788P] 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    'H-atoms riding'
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef       0.0026(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2631
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1787
_refine_ls_wR_factor_gt          0.1721
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.004
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4159(2) 0.2533(2) -0.07767(10) 0.0421(4) Uani 1 d . . .
C2 C 0.2214(3) 0.2811(3) -0.10724(11) 0.0469(4) Uani 1 d . . .
H2A H 0.1225 0.3023 -0.0627 0.069(6) Uiso 1 calc R . .
C3 C 0.1715(3) 0.2781(3) -0.19984(12) 0.0483(4) Uani 1 d . . .
H3A H 0.0389 0.2986 -0.2180 0.063(6) Uiso 1 calc R . .
C4 C 0.3161(3) 0.2448(2) -0.26880(10) 0.0458(4) Uani 1 d . . .
C5 C 0.5125(3) 0.2174(3) -0.23812(12) 0.0501(4) Uani 1 d . . .
H5A H 0.6122 0.1962 -0.2823 0.081(7) Uiso 1 calc R . .
C6 C 0.5610(3) 0.2210(2) -0.14514(12) 0.0473(4) Uani 1 d . . .
H6A H 0.6931 0.2016 -0.1264 0.054(5) Uiso 1 calc R . .
N7 N 0.2667(3) 0.2356(2) -0.35977(10) 0.0630(5) Uani 1 d . . .
C8 C 0.0648(4) 0.2685(4) -0.39125(16) 0.0839(8) Uani 1 d . . .
H8A H 0.0586 0.2567 -0.4581 0.132(12) Uiso 1 calc R . .
H8B H -0.0036 0.4001 -0.3857 0.107(10) Uiso 1 calc R . .
H8C H 0.0039 0.1708 -0.3511 0.085(8) Uiso 1 calc R . .
C9 C 0.4148(5) 0.2254(4) -0.43342(14) 0.0892(9) Uani 1 d . . .
H9A H 0.3550 0.2202 -0.4940 0.122(11) Uiso 1 calc R . .
H9B H 0.5173 0.1076 -0.4126 0.112(10) Uiso 1 calc R . .
H9C H 0.4703 0.3418 -0.4425 0.122(12) Uiso 1 calc R . .
C10 C 0.4650(3) 0.2590(2) 0.01784(11) 0.0466(4) Uani 1 d . . .
C11 C 0.5046(3) 0.2646(2) 0.09996(11) 0.0490(4) Uani 1 d . . .
C12 C 0.5438(3) 0.2693(2) 0.19568(11) 0.0460(4) Uani 1 d . . .
C13 C 0.3827(3) 0.2997(3) 0.25918(12) 0.0501(4) Uani 1 d . . .
N14 N 0.2544(3) 0.3204(3) 0.30835(14) 0.0790(6) Uani 1 d . . .
C15 C 0.7278(3) 0.2456(2) 0.23338(11) 0.0474(4) Uani 1 d . . .
C16 C 0.7574(3) 0.2535(3) 0.33228(12) 0.0504(4) Uani 1 d . . .
N17 N 0.7836(3) 0.2588(3) 0.41084(11) 0.0679(5) Uani 1 d . . .
C18 C 0.8924(3) 0.2069(3) 0.17396(13) 0.0525(4) Uani 1 d . . .
N19 N 1.0240(3) 0.1745(4) 0.12828(16) 0.0859(6) Uani 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 0.0617(9) 0.0370(8) 0.0286(7) -0.0071(5) -0.0021(6) -0.0126(6)
C2 0.0580(9) 0.0502(9) 0.0337(7) -0.0107(6) 0.0056(6) -0.0132(7)
C3 0.0557(9) 0.0511(9) 0.0383(8) -0.0102(7) -0.0040(7) -0.0117(7)
C4 0.0727(11) 0.0358(8) 0.0286(7) -0.0075(6) -0.0016(6) -0.0106(7)
C5 0.0662(10) 0.0467(9) 0.0389(8) -0.0139(7) 0.0115(7) -0.0116(8)
C6 0.0540(9) 0.0441(9) 0.0445(8) -0.0111(7) 0.0003(7) -0.0106(7)
N7 0.1021(13) 0.0559(9) 0.0299(7) -0.0132(6) -0.0077(7) -0.0101(8)
C8 0.124(2) 0.0732(15) 0.0513(11) -0.0189(10) -0.0400(12) -0.0059(14)
C9 0.149(2) 0.0824(16) 0.0310(9) -0.0190(9) 0.0132(11) -0.0084(17)
C10 0.0659(10) 0.0412(9) 0.0340(8) -0.0064(6) -0.0040(7) -0.0156(7)
C11 0.0675(11) 0.0445(9) 0.0368(8) -0.0079(6) -0.0030(7) -0.0166(8)
C12 0.0604(10) 0.0426(8) 0.0356(8) -0.0084(6) 0.0017(6) -0.0124(7)
C13 0.0537(9) 0.0584(10) 0.0397(8) -0.0137(7) 0.0000(7) -0.0121(8)
N14 0.0638(10) 0.1094(16) 0.0653(11) -0.0264(10) 0.0165(9) -0.0157(10)
C15 0.0596(10) 0.0447(9) 0.0386(8) -0.0099(6) 0.0000(7) -0.0118(7)
C16 0.0583(10) 0.0522(10) 0.0415(9) -0.0117(7) -0.0057(7) -0.0119(8)
N17 0.0790(11) 0.0895(13) 0.0396(8) -0.0206(8) -0.0083(7) -0.0203(9)
C18 0.0529(9) 0.0578(10) 0.0500(9) -0.0180(8) 0.0046(7) -0.0132(8)
N19 0.0700(12) 0.1017(15) 0.0948(15) -0.0397(12) 0.0283(11) -0.0213(11)
_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 1.392(2) . ?
C1 C6 1.401(2) . ?
C1 C10 1.410(2) . ?
C2 C3 1.366(2) . ?
C3 C4 1.415(2) . ?
C4 N7 1.356(2) . ?
C4 C5 1.410(3) . ?
C5 C6 1.370(2) . ?
N7 C8 1.445(3) . ?
N7 C9 1.463(3) . ?
C10 C11 1.209(2) . ?
C11 C12 1.394(2) . ?
C12 C15 1.365(3) . ?
C12 C13 1.442(2) . ?
C13 N14 1.133(2) . ?
C15 C18 1.431(2) . ?
C15 C16 1.432(2) . ?
C16 N17 1.139(2) . ?
C18 N19 1.129(3) . ?
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 C6 118.46(15) . . ?
C2 C1 C10 120.59(15) . . ?
C6 C1 C10 120.95(15) . . ?
C3 C2 C1 121.24(15) . . ?
C2 C3 C4 121.06(16) . . ?
N7 C4 C5 121.82(17) . . ?
N7 C4 C3 120.97(17) . . ?
C5 C4 C3 117.20(14) . . ?
C6 C5 C4 121.27(16) . . ?
C5 C6 C1 120.77(16) . . ?
C4 N7 C8 121.42(19) . . ?
C4 N7 C9 120.2(2) . . ?
C8 N7 C9 117.60(18) . . ?
C11 C10 C1 179.17(18) . . ?
C10 C11 C12 177.93(19) . . ?
C15 C12 C11 123.57(16) . . ?
C15 C12 C13 117.64(15) . . ?
C11 C12 C13 118.79(16) . . ?
N14 C13 C12 178.4(2) . . ?
C12 C15 C18 119.45(15) . . ?
C12 C15 C16 120.63(16) . . ?
C18 C15 C16 119.90(16) . . ?
N17 C16 C15 179.1(2) . . ?
N19 C18 C15 178.9(2) . . ?
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
C6 C1 C2 C3 -0.3(3) . . . . ?
C10 C1 C2 C3 179.28(15) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 N7 177.87(15) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
N7 C4 C5 C6 -177.98(15) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C10 C1 C6 C5 -179.41(14) . . . . ?
C5 C4 N7 C8 -178.51(18) . . . . ?
C3 C4 N7 C8 2.9(3) . . . . ?
C5 C4 N7 C9 -9.0(3) . . . . ?
C3 C4 N7 C9 172.46(18) . . . . ?
C2 C1 C10 C11 -6(11) . . . . ?
C6 C1 C10 C11 173(100) . . . . ?
C1 C10 C11 C12 29(15) . . . . ?
C10 C11 C12 C15 158(5) . . . . ?
C10 C11 C12 C13 -21(5) . . . . ?
C15 C12 C13 N14 -133(7) . . . . ?
C11 C12 C13 N14 47(7) . . . . ?
C11 C12 C15 C18 -2.2(3) . . . . ?
C13 C12 C15 C18 177.41(15) . . . . ?
C11 C12 C15 C16 179.60(15) . . . . ?
C13 C12 C15 C16 -0.8(3) . . . . ?
C12 C15 C16 N17 170(12) . . . . ?
C18 C15 C16 N17 -8(12) . . . . ?
C12 C15 C18 N19 -145(11) . . . . ?
C16 C15 C18 N19 33(12) . . . . ?
_diffrn_measured_fraction_theta_max 0.956
_diffrn_reflns_theta_full        74.87
_diffrn_measured_fraction_theta_full 0.956
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.041

data_moon4_D_02
_database_code_CSD               207517
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H20 N4'
_chemical_formula_sum            'C24 H20 N4'
_chemical_formula_weight         364.44
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   3.9477(2)
_cell_length_b                   11.1064(4)
_cell_length_c                   22.3725(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.769(2)
_cell_angle_gamma                90.00
_cell_volume                     978.79(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1778
_cell_measurement_theta_min      2.05
_cell_measurement_theta_max      27.52
_exptl_crystal_description       'Cut fragment'
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   non
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_reflns_number            4186
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0702
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         27.52
_reflns_number_total             2232
_reflns_number_gt                1350
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Kappa CCD'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'Denzo + Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Johnson,1976)'
_computing_publication_material  SHELXL97
_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     
'w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+0.0806P] 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    'H-atoms riding'
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef       0.061(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2232
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1582
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   1.267
_refine_ls_restrained_S_all      1.267
_refine_ls_shift/su_max          0.106
_refine_ls_shift/su_mean         0.008
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.9970(5) -0.04818(19) -0.98078(8) 0.0285(5) Uani 1 d . . .
C2 C -1.1246(5) -0.1621(2) -1.00341(9) 0.0335(5) Uani 1 d . . .
N3 N -1.2263(5) -0.2524(2) -1.02167(9) 0.0496(6) Uani 1 d . . .
C4 C -0.8674(5) -0.04151(19) -0.92028(9) 0.0298(5) Uani 1 d . . .
C5 C -0.7538(5) -0.02860(19) -0.86928(9) 0.0288(5) Uani 1 d . . .
C6 C -0.6189(5) -0.00817(19) -0.80964(8) 0.0269(5) Uani 1 d . . .
C7 C -0.4373(5) 0.09687(19) -0.79510(9) 0.0273(5) Uani 1 d . . .
H7A H -0.4012 0.1533 -0.8253 0.025 Uiso 1 d R . .
C8 C -0.3107(5) 0.11914(19) -0.73769(9) 0.0264(5) Uani 1 d . . .
H8A H -0.1906 0.1909 -0.7293 0.023 Uiso 1 d R . .
C9 C -0.3572(5) 0.03669(18) -0.69099(8) 0.0256(5) Uani 1 d . . .
C10 C -0.5412(5) -0.06934(19) -0.70576(9) 0.0268(5) Uani 1 d . . .
H10A H -0.5768 -0.1264 -0.6758 0.032 Uiso 1 d R . .
C11 C -0.6692(5) -0.09016(19) -0.76344(9) 0.0274(5) Uani 1 d . . .
H11A H -0.7931 -0.1610 -0.7721 0.026 Uiso 1 d R . .
N12 N -0.2292(4) 0.05905(17) -0.63378(7) 0.0303(5) Uani 1 d . . .
C13 C -0.0507(5) 0.1709(2) -0.61991(9) 0.0328(5) Uani 1 d . . .
H13A H 0.0252 0.1721 -0.5778 0.039 Uiso 1 d R . .
H13B H -0.2023 0.2383 -0.6287 0.036 Uiso 1 d R . .
H13C H 0.1441 0.1772 -0.6440 0.036 Uiso 1 d R . .
C14 C -0.3042(6) -0.0213(2) -0.58504(9) 0.0377(6) Uani 1 d . . .
H14A H -0.1926 0.0079 -0.5479 0.058 Uiso 1 d R . .
H14B H -0.2222 -0.1015 -0.5934 0.062 Uiso 1 d R . .
H14C H -0.5475 -0.0239 -0.5813 0.045 Uiso 1 d 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
C1 0.0248(10) 0.0313(12) 0.0291(12) -0.0045(9) 0.0003(9) -0.0002(9)
C2 0.0359(12) 0.0363(14) 0.0282(12) 0.0000(10) 0.0018(9) -0.0021(11)
N3 0.0617(14) 0.0394(13) 0.0477(13) -0.0070(10) 0.0035(10) -0.0106(10)
C4 0.0277(11) 0.0298(12) 0.0322(13) -0.0023(9) 0.0032(9) -0.0012(9)
C5 0.0251(11) 0.0286(12) 0.0328(12) -0.0005(9) 0.0037(9) 0.0008(9)
C6 0.0235(10) 0.0307(12) 0.0264(11) -0.0025(9) 0.0018(8) 0.0045(9)
C7 0.0255(11) 0.0268(12) 0.0298(12) 0.0036(9) 0.0039(9) 0.0028(9)
C8 0.0235(11) 0.0233(11) 0.0324(12) -0.0029(9) 0.0013(8) -0.0004(8)
C9 0.0208(10) 0.0274(12) 0.0286(11) -0.0027(9) 0.0021(8) 0.0050(8)
C10 0.0258(10) 0.0254(12) 0.0295(12) 0.0030(9) 0.0033(8) 0.0023(9)
C11 0.0225(10) 0.0250(12) 0.0350(12) -0.0035(9) 0.0023(8) 0.0010(9)
N12 0.0301(10) 0.0338(11) 0.0265(10) -0.0010(8) -0.0016(7) -0.0014(8)
C13 0.0278(11) 0.0369(13) 0.0333(12) -0.0056(10) -0.0019(9) 0.0018(10)
C14 0.0382(12) 0.0420(15) 0.0324(12) 0.0034(11) -0.0013(9) 0.0007(11)
_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 C1 1.372(4) 3_353 ?
C1 C4 1.417(3) . ?
C1 C2 1.441(3) . ?
C2 N3 1.146(3) . ?
C4 C5 1.207(3) . ?
C5 C6 1.422(3) . ?
C6 C7 1.397(3) . ?
C6 C11 1.401(3) . ?
C7 C8 1.370(3) . ?
C8 C9 1.410(3) . ?
C9 N12 1.368(2) . ?
C9 C10 1.411(3) . ?
C10 C11 1.374(3) . ?
N12 C13 1.452(3) . ?
N12 C14 1.454(3) . ?
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
C1 C1 C4 123.2(2) 3_353 . ?
C1 C1 C2 118.3(2) 3_353 . ?
C4 C1 C2 118.51(18) . . ?
N3 C2 C1 179.7(2) . . ?
C5 C4 C1 176.1(2) . . ?
C4 C5 C6 177.6(2) . . ?
C7 C6 C11 117.81(18) . . ?
C7 C6 C5 120.45(18) . . ?
C11 C6 C5 121.73(19) . . ?
C8 C7 C6 121.29(19) . . ?
C7 C8 C9 121.34(19) . . ?
N12 C9 C8 121.15(18) . . ?
N12 C9 C10 121.57(18) . . ?
C8 C9 C10 117.28(17) . . ?
C11 C10 C9 120.80(19) . . ?
C10 C11 C6 121.47(18) . . ?
C9 N12 C13 119.98(17) . . ?
C9 N12 C14 120.62(18) . . ?
C13 N12 C14 118.99(16) . . ?
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
C1 C1 C2 N3 5(42) 3_353 . . . ?
C4 C1 C2 N3 -174(100) . . . . ?
C1 C1 C4 C5 3(3) 3_353 . . . ?
C2 C1 C4 C5 -178(100) . . . . ?
C1 C4 C5 C6 4(8) . . . . ?
C4 C5 C6 C7 -20(5) . . . . ?
C4 C5 C6 C11 158(5) . . . . ?
C11 C6 C7 C8 0.3(3) . . . . ?
C5 C6 C7 C8 178.82(18) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 N12 179.73(18) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
N12 C9 C10 C11 179.76(18) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C6 0.7(3) . . . . ?
C7 C6 C11 C10 -0.8(3) . . . . ?
C5 C6 C11 C10 -179.31(18) . . . . ?
C8 C9 N12 C13 1.9(3) . . . . ?
C10 C9 N12 C13 -178.00(17) . . . . ?
C8 C9 N12 C14 174.51(18) . . . . ?
C10 C9 N12 C14 -5.4(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.941
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.941
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.092