Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2002

data_global

_journal_coden_Cambridge      182


loop_
_publ_author_name
'Shinji Yamada'
'Akie Homma'

_publ_contact_author_name     	'Dr Shinji Yamada'  
_publ_contact_author_address 
;
Department of Chemistry
Ochanomizu University
Faculty of Science
2-1-1 Otsuka
Bunkyo-ku
Tokyo
112-8610
JAPAN
;

_publ_contact_author_email       'YAMADA@CC.OCHA.AC.JP'

_publ_requested_journal       'Chemical Communications'


_publ_section_title		
;
N-Substituent effect on the cis-trans geometry of
nine-membered lactams
;
data_shelxl_1a
_database_code_CSD 190921
_audit_creation_method            SHELXL
_chemical_name_systematic
;
1-Acetylazonan-2-one
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum             'C10 H17 N O2'
_chemical_formula_weight          183.25
_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'   0.0181   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'
'O'  'O'   0.0492   0.0322
'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                    11.988(2)
_cell_length_b                    7.2178(14)
_cell_length_c                    11.4456(15)
_cell_angle_alpha                 90.00
_cell_angle_beta                  99.370(12)
_cell_angle_gamma                 90.00
_cell_volume                      977.1(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     230(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?

_exptl_crystal_description        prismatic
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.4
_exptl_crystal_size_mid           0.3
_exptl_crystal_size_min           0.3
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.246
_exptl_crystal_density_method     ?
_exptl_crystal_F_000              400
_exptl_absorpt_coefficient_mu     0.692
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?

_exptl_special_details
;
?
;

_diffrn_ambient_temperature       230(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device        'Rigaku afc7r'
_diffrn_measurement_method        ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             1870
_diffrn_reflns_av_R_equivalents   0.0344
_diffrn_reflns_av_sigmaI/netI     0.0109
_diffrn_reflns_limit_h_min        0
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        0
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          4.95
_diffrn_reflns_theta_max          67.98
_reflns_number_total              1781
_reflns_number_observed           1680
_reflns_observed_criterion        >2sigma(I)

_computing_data_collection        'Rigaku afc7r'
_computing_cell_refinement        'Rigaku afc7r'
_computing_data_reduction         ?
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics     SHELXTL
_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^)+(0.0565P)^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      SHELXL
_refine_ls_extinction_coef        0.0660(63)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns          1781
_refine_ls_number_parameters      119
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0426
_refine_ls_R_factor_obs           0.0409
_refine_ls_wR_factor_all          0.1681
_refine_ls_wR_factor_obs          0.1665
_refine_ls_goodness_of_fit_all    2.581
_refine_ls_goodness_of_fit_obs    2.637
_refine_ls_restrained_S_all       2.581
_refine_ls_restrained_S_obs       2.637
_refine_ls_shift/esd_max          -0.059
_refine_ls_shift/esd_mean         0.010

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
O1 O 0.67431(8) 0.49523(13) 0.76142(10) 0.0451(4) Uani 1 d . .
O2 O 0.44261(9) 0.1995(2) 0.89313(10) 0.0501(4) Uani 1 d . .
N1 N 0.50780(8) 0.47144(14) 0.83291(9) 0.0283(4) Uani 1 d . .
C1 C 0.59431(9) 0.5728(2) 0.79207(10) 0.0308(4) Uani 1 d . .
C2 C 0.58630(10) 0.7819(2) 0.79083(11) 0.0338(4) Uani 1 d . .
C3 C 0.54842(11) 0.8718(2) 0.66880(11) 0.0373(4) Uani 1 d . .
C4 C 0.42095(12) 0.8910(2) 0.62678(12) 0.0392(4) Uani 1 d . .
C5 C 0.36591(12) 0.7396(2) 0.54317(11) 0.0412(4) Uani 1 d . .
C6 C 0.38277(11) 0.5387(2) 0.58333(11) 0.0356(4) Uani 1 d . .
C7 C 0.32799(10) 0.4813(2) 0.68919(12) 0.0366(4) Uani 1 d . .
C8 C 0.39053(10) 0.5397(2) 0.81014(11) 0.0320(4) Uani 1 d . .
C9 C 0.52396(10) 0.2918(2) 0.87928(10) 0.0328(4) Uani 1 d . .
C10 C 0.64182(11) 0.2217(2) 0.91816(12) 0.0382(4) Uani 1 d . .
H1 H 0.5400 0.8290 0.8496 0.057 Uiso 1 d . .
H2 H 0.6600 0.8248 0.8203 0.057 Uiso 1 d . .
H3 H 0.5800 0.9956 0.6764 0.057 Uiso 1 d . .
H4 H 0.5800 0.8000 0.6055 0.057 Uiso 1 d . .
H5 H 0.3800 0.9071 0.6987 0.057 Uiso 1 d . .
H6 H 0.4000 1.0106 0.5819 0.057 Uiso 1 d . .
H7 H 0.2800 0.7695 0.5207 0.057 Uiso 1 d . .
H8 H 0.4000 0.7501 0.4586 0.057 Uiso 1 d . .
H9 H 0.3400 0.4641 0.5150 0.057 Uiso 1 d . .
H10 H 0.4600 0.5023 0.5994 0.057 Uiso 1 d . .
H11 H 0.2600 0.5290 0.6817 0.057 Uiso 1 d . .
H12 H 0.3200 0.3418 0.6930 0.057 Uiso 1 d . .
H13 H 0.4000 0.6757 0.8200 0.057 Uiso 1 d . .
H14 H 0.3600 0.4883 0.8742 0.057 Uiso 1 d . .
H15 H 0.6800 0.1736 0.8475 0.057 Uiso 1 d . .
H16 H 0.7000 0.3193 0.9508 0.057 Uiso 1 d . .
H17 H 0.6400 0.1194 0.9716 0.057 Uiso 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
O1 0.0304(6) 0.0468(7) 0.0624(7) 0.0077(5) 0.0204(5) 0.0066(4)
O2 0.0399(6) 0.0447(6) 0.0656(7) 0.0155(5) 0.0087(5) -0.0069(4)
N1 0.0226(6) 0.0325(6) 0.0301(6) 0.0021(4) 0.0055(4) 0.0015(4)
C1 0.0243(6) 0.0358(7) 0.0321(7) 0.0015(4) 0.0041(5) -0.0009(5)
C2 0.0315(7) 0.0334(7) 0.0359(7) 0.0007(5) 0.0033(5) -0.0061(5)
C3 0.0383(8) 0.0365(7) 0.0375(7) 0.0045(5) 0.0078(6) -0.0032(5)
C4 0.0408(8) 0.0411(7) 0.0365(7) 0.0068(5) 0.0083(5) 0.0083(6)
C5 0.0351(8) 0.0564(9) 0.0307(7) 0.0054(6) 0.0011(5) 0.0018(6)
C6 0.0264(7) 0.0497(8) 0.0309(7) -0.0081(5) 0.0049(5) -0.0037(5)
C7 0.0201(7) 0.0493(8) 0.0405(8) 0.0013(5) 0.0054(5) -0.0025(5)
C8 0.0239(7) 0.0407(7) 0.0340(7) 0.0014(5) 0.0123(5) 0.0031(5)
C9 0.0337(7) 0.0327(7) 0.0314(7) 0.0001(5) 0.0037(5) -0.0010(5)
C10 0.0375(8) 0.0359(7) 0.0388(8) 0.0006(5) -0.0008(6) 0.0047(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
O1 C1 1.2108(15) . ?
O2 C9 1.212(2) . ?
N1 C9 1.403(2) . ?
N1 C1 1.4096(15) . ?
N1 C8 1.4723(15) . ?
C1 C2 1.512(2) . ?
C2 C3 1.540(2) . ?
C3 C4 1.532(2) . ?
C4 C5 1.529(2) . ?
C5 C6 1.525(2) . ?
C6 C7 1.526(2) . ?
C7 C8 1.522(2) . ?
C9 C10 1.499(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
C9 N1 C1 122.80(10) . . ?
C9 N1 C8 116.43(10) . . ?
C1 N1 C8 120.04(10) . . ?
O1 C1 N1 121.08(12) . . ?
O1 C1 C2 120.72(11) . . ?
N1 C1 C2 118.17(10) . . ?
C1 C2 C3 115.98(10) . . ?
C4 C3 C2 117.05(11) . . ?
C5 C4 C3 116.00(11) . . ?
C6 C5 C4 117.93(10) . . ?
C5 C6 C7 116.37(11) . . ?
C8 C7 C6 115.79(10) . . ?
N1 C8 C7 112.53(10) . . ?
O2 C9 N1 119.53(11) . . ?
O2 C9 C10 121.01(12) . . ?
N1 C9 C10 119.34(11) . . ?

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
C9 N1 C1 O1 22.6(2) . . . . ?
C8 N1 C1 O1 -147.25(13) . . . . ?
C9 N1 C1 C2 -155.67(11) . . . . ?
C8 N1 C1 C2 34.5(2) . . . . ?
O1 C1 C2 C3 78.0(2) . . . . ?
N1 C1 C2 C3 -103.76(12) . . . . ?
C1 C2 C3 C4 86.62(14) . . . . ?
C2 C3 C4 C5 -97.21(13) . . . . ?
C3 C4 C5 C6 54.4(2) . . . . ?
C4 C5 C6 C7 66.67(15) . . . . ?
C5 C6 C7 C8 -78.51(14) . . . . ?
C9 N1 C8 C7 -85.50(13) . . . . ?
C1 N1 C8 C7 84.98(13) . . . . ?
C6 C7 C8 N1 -56.6(2) . . . . ?
C1 N1 C9 O2 -166.87(12) . . . . ?
C8 N1 C9 O2 3.3(2) . . . . ?
C1 N1 C9 C10 17.0(2) . . . . ?
C8 N1 C9 C10 -172.76(11) . . . . ?

_refine_diff_density_max    0.229
_refine_diff_density_min   -0.181
_refine_diff_density_rms    0.042


data_shelxl_1b
_database_code_CSD 190922
_audit_creation_method            SHELXL
_chemical_name_systematic
;
1-Isobutyrylazonan-2-one
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum             'C12 H21 N O2'
_chemical_formula_weight          211.30
_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'   0.0181   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'
'O'  'O'   0.0492   0.0322
'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                    10.068(4)
_cell_length_b                    23.305(2)
_cell_length_c                    5.1428(13)
_cell_angle_alpha                 90.00
_cell_angle_beta                  91.86(3)
_cell_angle_gamma                 90.00
_cell_volume                      1206.0(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     230(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?

_exptl_crystal_description        prismatic
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.5
_exptl_crystal_size_mid           0.4
_exptl_crystal_size_min           0.3
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.164
_exptl_crystal_density_method     ?
_exptl_crystal_F_000              464
_exptl_absorpt_coefficient_mu     0.621
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?

_exptl_special_details
;
?
;

_diffrn_ambient_temperature       230(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device        'Rigaku afc7r'
_diffrn_measurement_method        ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             6101
_diffrn_reflns_av_R_equivalents   0.0741
_diffrn_reflns_av_sigmaI/netI     0.0469
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -27
_diffrn_reflns_limit_k_max        27
_diffrn_reflns_limit_l_min        -4
_diffrn_reflns_limit_l_max        6
_diffrn_reflns_theta_min          3.79
_diffrn_reflns_theta_max          67.98
_reflns_number_total              2190
_reflns_number_observed           1975
_reflns_observed_criterion        >2sigma(I)

_computing_data_collection        'Rigaku afc7r'
_computing_cell_refinement        'Rigaku afc7r'
_computing_data_reduction         ?
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics     SHELXTL
_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^)+(0.0641P)^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      SHELXL
_refine_ls_extinction_coef        0.0087(20)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns          2190
_refine_ls_number_parameters      137
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0503
_refine_ls_R_factor_obs           0.0460
_refine_ls_wR_factor_all          0.1776
_refine_ls_wR_factor_obs          0.1740
_refine_ls_goodness_of_fit_all    2.004
_refine_ls_goodness_of_fit_obs    2.074
_refine_ls_restrained_S_all       2.004
_refine_ls_restrained_S_obs       2.074
_refine_ls_shift/esd_max          0.086
_refine_ls_shift/esd_mean         0.011

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
O1 O 0.01262(9) 0.93032(4) 0.0621(2) 0.0368(3) Uani 1 d . .
O2 O 0.28542(12) 0.82500(5) -0.2269(3) 0.0568(4) Uani 1 d . .
N1 N 0.09413(11) 0.87506(4) -0.2649(2) 0.0300(3) Uani 1 d . .
C1 C 0.00152(12) 0.91337(5) -0.1603(2) 0.0288(4) Uani 1 d . .
C2 C -0.11033(14) 0.93506(6) -0.3359(3) 0.0357(4) Uani 1 d . .
C3 C -0.24766(14) 0.90858(8) -0.2918(3) 0.0461(4) Uani 1 d . .
C4 C -0.2796(2) 0.85098(9) -0.4242(3) 0.0531(5) Uani 1 d . .
C5 C -0.2547(2) 0.79725(9) -0.2591(4) 0.0550(5) Uani 1 d . .
C6 C -0.1151(2) 0.78655(7) -0.1475(3) 0.0444(4) Uani 1 d . .
C7 C -0.0066(2) 0.77849(6) -0.3432(3) 0.0397(4) Uani 1 d . .
C8 C 0.04822(14) 0.83303(6) -0.4628(2) 0.0343(4) Uani 1 d . .
C9 C 0.22382(14) 0.86686(6) -0.1607(3) 0.0368(4) Uani 1 d . .
C10 C 0.28908(15) 0.91331(7) 0.0051(3) 0.0432(4) Uani 1 d . .
C11 C 0.3093(2) 0.96633(8) -0.1590(5) 0.0653(6) Uani 1 d . .
C12 C 0.4188(2) 0.89112(9) 0.1288(4) 0.0628(5) Uani 1 d . .
H1 H -0.1000 0.9329 -0.5144 0.067 Uiso 1 d . .
H2 H -0.1200 0.9760 -0.2862 0.067 Uiso 1 d . .
H3 H -0.3200 0.9364 -0.3511 0.067 Uiso 1 d . .
H4 H -0.2600 0.9053 -0.1067 0.067 Uiso 1 d . .
H5 H -0.2400 0.8484 -0.5958 0.067 Uiso 1 d . .
H6 H -0.3800 0.8517 -0.4799 0.067 Uiso 1 d . .
H7 H -0.2800 0.7641 -0.3670 0.067 Uiso 1 d . .
H8 H -0.3200 0.7990 -0.1187 0.067 Uiso 1 d . .
H9 H -0.1200 0.7511 -0.0325 0.067 Uiso 1 d . .
H10 H -0.1000 0.8174 -0.0255 0.067 Uiso 1 d . .
H11 H -0.0400 0.7543 -0.4869 0.067 Uiso 1 d . .
H12 H 0.0600 0.7564 -0.2513 0.067 Uiso 1 d . .
H13 H -0.0200 0.8511 -0.5722 0.067 Uiso 1 d . .
H14 H 0.1200 0.8242 -0.5763 0.067 Uiso 1 d . .
H15 H 0.2200 0.9229 0.1506 0.067 Uiso 1 d . .
H16 H 0.3600 0.9566 -0.2812 0.067 Uiso 1 d . .
H17 H 0.3600 0.9948 -0.0671 0.067 Uiso 1 d . .
H18 H 0.2200 0.9851 -0.2157 0.067 Uiso 1 d . .
H19 H 0.4600 0.9212 0.2430 0.067 Uiso 1 d . .
H20 H 0.4000 0.8563 0.2492 0.067 Uiso 1 d . .
H21 H 0.4800 0.8832 -0.0105 0.067 Uiso 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
O1 0.0401(6) 0.0402(6) 0.0303(5) -0.0033(4) 0.0042(4) 0.0004(4)
O2 0.0456(7) 0.0435(7) 0.0805(9) -0.0177(6) -0.0088(6) 0.0147(5)
N1 0.0319(6) 0.0268(6) 0.0311(6) -0.0023(4) 0.0002(4) 0.0019(4)
C1 0.0321(7) 0.0243(6) 0.0302(6) 0.0039(4) 0.0047(5) -0.0006(5)
C2 0.0388(8) 0.0352(8) 0.0330(7) 0.0032(5) 0.0017(5) 0.0089(6)
C3 0.0342(8) 0.0551(10) 0.0486(9) -0.0005(7) -0.0023(6) 0.0079(7)
C4 0.0383(8) 0.0684(12) 0.0519(9) -0.0077(8) -0.0113(7) -0.0028(8)
C5 0.0459(9) 0.0562(11) 0.0629(10) -0.0074(8) 0.0033(7) -0.0184(8)
C6 0.0575(9) 0.0375(8) 0.0379(8) 0.0031(6) -0.0018(7) -0.0137(7)
C7 0.0492(8) 0.0278(8) 0.0414(8) -0.0015(5) -0.0089(6) -0.0031(6)
C8 0.0415(7) 0.0314(8) 0.0299(7) -0.0042(5) -0.0003(5) 0.0017(6)
C9 0.0329(7) 0.0332(8) 0.0442(8) -0.0002(6) -0.0003(6) 0.0033(6)
C10 0.0343(7) 0.0407(8) 0.0543(9) -0.0078(7) -0.0031(6) -0.0017(6)
C11 0.0697(12) 0.0421(11) 0.0836(13) 0.0021(9) -0.0040(10) -0.0122(9)
C12 0.0429(9) 0.0641(12) 0.0801(13) -0.0001(10) -0.0180(9) -0.0037(9)

_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
O1 C1 1.212(2) . ?
O2 C9 1.211(2) . ?
N1 C9 1.408(2) . ?
N1 C1 1.410(2) . ?
N1 C8 1.476(2) . ?
C1 C2 1.507(2) . ?
C2 C3 1.538(2) . ?
C3 C4 1.535(3) . ?
C4 C5 1.529(3) . ?
C5 C6 1.521(3) . ?
C6 C7 1.521(2) . ?
C7 C8 1.523(2) . ?
C9 C10 1.515(2) . ?
C10 C11 1.514(3) . ?
C10 C12 1.525(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
C9 N1 C1 123.86(11) . . ?
C9 N1 C8 115.98(11) . . ?
C1 N1 C8 119.16(11) . . ?
O1 C1 N1 121.63(12) . . ?
O1 C1 C2 120.03(12) . . ?
N1 C1 C2 118.29(11) . . ?
C1 C2 C3 115.78(12) . . ?
C4 C3 C2 117.54(13) . . ?
C5 C4 C3 116.22(14) . . ?
C6 C5 C4 118.45(14) . . ?
C7 C6 C5 116.43(13) . . ?
C6 C7 C8 116.20(12) . . ?
N1 C8 C7 112.64(10) . . ?
O2 C9 N1 118.64(13) . . ?
O2 C9 C10 121.17(14) . . ?
N1 C9 C10 119.81(12) . . ?
C11 C10 C9 109.45(14) . . ?
C11 C10 C12 112.38(15) . . ?
C9 C10 C12 110.03(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
C9 N1 C1 O1 -20.3(2) . . . . ?
C8 N1 C1 O1 147.76(12) . . . . ?
C9 N1 C1 C2 157.30(12) . . . . ?
C8 N1 C1 C2 -34.6(2) . . . . ?
O1 C1 C2 C3 -77.4(2) . . . . ?
N1 C1 C2 C3 104.97(14) . . . . ?
C1 C2 C3 C4 -83.8(2) . . . . ?
C2 C3 C4 C5 95.4(2) . . . . ?
C3 C4 C5 C6 -58.5(2) . . . . ?
C4 C5 C6 C7 -62.0(2) . . . . ?
C5 C6 C7 C8 79.8(2) . . . . ?
C9 N1 C8 C7 83.7(2) . . . . ?
C1 N1 C8 C7 -85.32(14) . . . . ?
C6 C7 C8 N1 53.5(2) . . . . ?
C1 N1 C9 O2 164.27(14) . . . . ?
C8 N1 C9 O2 -4.2(2) . . . . ?
C1 N1 C9 C10 -22.8(2) . . . . ?
C8 N1 C9 C10 168.80(12) . . . . ?
O2 C9 C10 C11 108.0(2) . . . . ?
N1 C9 C10 C11 -64.8(2) . . . . ?
O2 C9 C10 C12 -16.0(2) . . . . ?
N1 C9 C10 C12 171.26(14) . . . . ?

_refine_diff_density_max    0.339
_refine_diff_density_min   -0.242
_refine_diff_density_rms    0.039


data_shelxl_1c
_database_code_CSD 190923
_audit_creation_method            SHELXL
_chemical_name_systematic
;
1-(2,2-Dimethylpropionyl)azonan-2-one
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum             'C13 H23 N O2'
_chemical_formula_weight          225.32
_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'   0.0181   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'
'O'  'O'   0.0492   0.0322
'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                    10.462(2)
_cell_length_b                    22.892(5)
_cell_length_c                    5.5006(9)
_cell_angle_alpha                 90.00
_cell_angle_beta                  94.201(14)
_cell_angle_gamma                 90.00
_cell_volume                      1313.8(4)
_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        prismatic
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.5
_exptl_crystal_size_mid           0.3
_exptl_crystal_size_min           0.2
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.139
_exptl_crystal_density_method     ?
_exptl_crystal_F_000              496
_exptl_absorpt_coefficient_mu     0.598
_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      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device        'Rigaku afc7r'
_diffrn_measurement_method        ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             3322
_diffrn_reflns_av_R_equivalents   0.0178
_diffrn_reflns_av_sigmaI/netI     0.0204
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        0
_diffrn_reflns_limit_k_max        27
_diffrn_reflns_limit_l_min        -6
_diffrn_reflns_limit_l_max        4
_diffrn_reflns_theta_min          3.86
_diffrn_reflns_theta_max          67.94
_reflns_number_total              2395
_reflns_number_observed           2135
_reflns_observed_criterion        >2sigma(I)

_computing_data_collection        'Rigaku afc7r'
_computing_cell_refinement        'Rigaku afc7r'
_computing_data_reduction         ?
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics     SHELXTL
_computing_publication_material   ?

_refine_special_details
;
Refinement on F^2^ for ALL reflections except for 5 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^)+(0.1000P)^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      SHELXL
_refine_ls_extinction_coef        0.0121(22)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns          2390
_refine_ls_number_parameters      146
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0498
_refine_ls_R_factor_obs           0.0435
_refine_ls_wR_factor_all          0.1849
_refine_ls_wR_factor_obs          0.1698
_refine_ls_goodness_of_fit_all    1.525
_refine_ls_goodness_of_fit_obs    1.559
_refine_ls_restrained_S_all       1.601
_refine_ls_restrained_S_obs       1.559
_refine_ls_shift/esd_max          -0.062
_refine_ls_shift/esd_mean         0.009

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
O1 O 0.02471(10) 0.92193(5) 0.0267(2) 0.0414(3) Uani 1 d . .
O2 O 0.27909(10) 0.81591(5) -0.2247(2) 0.0481(4) Uani 1 d . .
N1 N 0.10154(10) 0.87080(4) -0.2874(2) 0.0283(3) Uani 1 d . .
C1 C 0.01348(12) 0.90823(5) -0.1874(2) 0.0304(4) Uani 1 d . .
C2 C -0.09429(13) 0.93246(6) -0.3539(3) 0.0370(4) Uani 1 d . .
C3 C -0.22837(14) 0.90744(7) -0.3181(3) 0.0443(4) Uani 1 d . .
C4 C -0.26229(14) 0.84874(8) -0.4385(3) 0.0521(5) Uani 1 d . .
C5 C -0.2399(2) 0.79474(8) -0.2793(4) 0.0576(5) Uani 1 d . .
C6 C -0.1047(2) 0.78260(7) -0.1715(3) 0.0503(5) Uani 1 d . .
C7 C -0.00243(15) 0.77247(6) -0.3520(3) 0.0423(4) Uani 1 d . .
C8 C 0.05183(12) 0.82654(6) -0.4678(2) 0.0331(4) Uani 1 d . .
C9 C 0.22829(12) 0.86238(5) -0.1900(2) 0.0306(4) Uani 1 d . .
C10 C 0.30784(13) 0.91280(6) -0.0710(2) 0.0335(4) Uani 1 d . .
C11 C 0.26563(15) 0.97356(6) -0.1625(3) 0.0405(4) Uani 1 d . .
C12 C 0.3067(2) 0.90869(8) 0.2071(3) 0.0522(5) Uani 1 d . .
C13 C 0.4460(2) 0.90299(7) -0.1360(3) 0.0460(4) Uani 1 d . .
H1 H -0.0800 0.9288 -0.5314 0.065 Uiso 1 d . .
H2 H -0.1000 0.9744 -0.3040 0.065 Uiso 1 d . .
H3 H -0.2400 0.9054 -0.1504 0.065 Uiso 1 d . .
H4 H -0.3000 0.9360 -0.3789 0.065 Uiso 1 d . .
H5 H -0.2200 0.8450 -0.5984 0.065 Uiso 1 d . .
H6 H -0.3400 0.8485 -0.4940 0.065 Uiso 1 d . .
H7 H -0.2600 0.7640 -0.3777 0.065 Uiso 1 d . .
H8 H -0.3000 0.7992 -0.1589 0.065 Uiso 1 d . .
H9 H -0.1000 0.7468 -0.0583 0.065 Uiso 1 d . .
H10 H -0.0800 0.8151 -0.0435 0.065 Uiso 1 d . .
H11 H 0.0600 0.7496 -0.2608 0.065 Uiso 1 d . .
H12 H -0.0400 0.7499 -0.4921 0.065 Uiso 1 d . .
H13 H 0.1200 0.8152 -0.5614 0.065 Uiso 1 d . .
H14 H -0.0200 0.8461 -0.5870 0.065 Uiso 1 d . .
H15 H 0.3400 1.0020 -0.1062 0.065 Uiso 1 d . .
H16 H 0.2600 0.9756 -0.3464 0.065 Uiso 1 d . .
H17 H 0.1800 0.9883 -0.1072 0.065 Uiso 1 d . .
H18 H 0.3600 0.9386 0.2812 0.065 Uiso 1 d . .
H19 H 0.3400 0.8740 0.2718 0.065 Uiso 1 d . .
H20 H 0.2200 0.9133 0.2625 0.065 Uiso 1 d . .
H21 H 0.5000 0.9344 -0.0539 0.065 Uiso 1 d . .
H22 H 0.4800 0.8658 -0.0687 0.065 Uiso 1 d . .
H23 H 0.4600 0.9018 -0.2782 0.065 Uiso 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
O1 0.0433(6) 0.0443(6) 0.0382(6) -0.0101(4) 0.0127(4) -0.0032(4)
O2 0.0399(6) 0.0329(6) 0.0701(7) -0.0079(5) -0.0052(5) 0.0077(4)
N1 0.0297(6) 0.0240(6) 0.0313(6) -0.0043(4) 0.0044(4) -0.0015(4)
C1 0.0323(7) 0.0239(6) 0.0365(7) -0.0015(4) 0.0118(5) -0.0041(4)
C2 0.0329(7) 0.0320(7) 0.0471(8) 0.0014(5) 0.0102(6) 0.0038(5)
C3 0.0308(8) 0.0440(9) 0.0593(9) -0.0020(7) 0.0110(6) 0.0033(6)
C4 0.0296(7) 0.0623(11) 0.0649(10) -0.0151(8) 0.0063(7) -0.0053(7)
C5 0.0493(9) 0.0447(9) 0.0822(12) -0.0162(8) 0.0277(9) -0.0180(7)
C6 0.0645(11) 0.0348(8) 0.0531(9) 0.0023(6) 0.0135(8) -0.0161(7)
C7 0.0450(8) 0.0266(7) 0.0551(9) -0.0060(6) 0.0012(6) -0.0039(6)
C8 0.0332(7) 0.0312(7) 0.0350(7) -0.0093(5) 0.0035(5) -0.0013(5)
C9 0.0322(7) 0.0276(7) 0.0322(7) 0.0013(5) 0.0039(5) 0.0006(5)
C10 0.0328(7) 0.0355(8) 0.0323(7) -0.0038(5) 0.0027(5) -0.0039(5)
C11 0.0446(8) 0.0293(7) 0.0482(8) -0.0054(5) 0.0081(6) -0.0084(6)
C12 0.0558(10) 0.0684(11) 0.0318(8) -0.0025(6) -0.0007(7) -0.0089(8)
C13 0.0315(8) 0.0555(9) 0.0508(9) -0.0062(7) 0.0018(6) -0.0043(6)

_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
O1 C1 1.216(2) . ?
O2 C9 1.211(2) . ?
N1 C1 1.400(2) . ?
N1 C9 1.407(2) . ?
N1 C8 1.485(2) . ?
C1 C2 1.505(2) . ?
C2 C3 1.541(2) . ?
C3 C4 1.528(2) . ?
C4 C5 1.523(3) . ?
C5 C6 1.519(3) . ?
C6 C7 1.530(2) . ?
C7 C8 1.521(2) . ?
C9 C10 1.541(2) . ?
C10 C13 1.531(2) . ?
C10 C11 1.533(2) . ?
C10 C12 1.533(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
C1 N1 C9 124.30(10) . . ?
C1 N1 C8 118.14(10) . . ?
C9 N1 C8 115.80(10) . . ?
O1 C1 N1 121.23(12) . . ?
O1 C1 C2 120.59(12) . . ?
N1 C1 C2 118.16(11) . . ?
C1 C2 C3 115.71(11) . . ?
C4 C3 C2 117.14(11) . . ?
C5 C4 C3 116.31(14) . . ?
C6 C5 C4 118.19(13) . . ?
C5 C6 C7 116.75(14) . . ?
C8 C7 C6 116.65(12) . . ?
N1 C8 C7 113.49(10) . . ?
O2 C9 N1 118.22(11) . . ?
O2 C9 C10 119.71(12) . . ?
N1 C9 C10 121.60(11) . . ?
C13 C10 C11 108.10(11) . . ?
C13 C10 C12 107.49(12) . . ?
C11 C10 C12 111.10(12) . . ?
C13 C10 C9 106.30(11) . . ?
C11 C10 C9 113.99(11) . . ?
C12 C10 C9 109.54(12) . . ?

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
C9 N1 C1 O1 -23.6(2) . . . . ?
C8 N1 C1 O1 140.59(12) . . . . ?
C9 N1 C1 C2 154.89(11) . . . . ?
C8 N1 C1 C2 -40.9(2) . . . . ?
O1 C1 C2 C3 -73.2(2) . . . . ?
N1 C1 C2 C3 108.29(13) . . . . ?
C1 C2 C3 C4 -81.5(2) . . . . ?
C2 C3 C4 C5 95.0(2) . . . . ?
C3 C4 C5 C6 -59.8(2) . . . . ?
C4 C5 C6 C7 -61.3(2) . . . . ?
C5 C6 C7 C8 79.3(2) . . . . ?
C1 N1 C8 C7 -80.69(14) . . . . ?
C9 N1 C8 C7 84.84(13) . . . . ?
C6 C7 C8 N1 53.4(2) . . . . ?
C1 N1 C9 O2 151.98(13) . . . . ?
C8 N1 C9 O2 -12.6(2) . . . . ?
C1 N1 C9 C10 -35.9(2) . . . . ?
C8 N1 C9 C10 159.59(11) . . . . ?
O2 C9 C10 C13 27.7(2) . . . . ?
N1 C9 C10 C13 -144.31(12) . . . . ?
O2 C9 C10 C11 146.69(13) . . . . ?
N1 C9 C10 C11 -25.3(2) . . . . ?
O2 C9 C10 C12 -88.1(2) . . . . ?
N1 C9 C10 C12 99.83(14) . . . . ?

_refine_diff_density_max    0.275
_refine_diff_density_min   -0.189
_refine_diff_density_rms    0.041


data_shelxl_1d
_database_code_CSD 190924
_audit_creation_method            SHELXL
_chemical_name_systematic
;
2-Oxoazonane-1-carboxylic acid benzyl ester
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum             'C16 H21 N O3'
_chemical_formula_weight          275.34
_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'   0.0181   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'
'O'  'O'   0.0492   0.0322
'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                    8.2108(13)
_cell_length_b                    12.2287(15)
_cell_length_c                    7.602(2)
_cell_angle_alpha                 96.600(14)
_cell_angle_beta                  99.012(15)
_cell_angle_gamma                 103.634(11)
_cell_volume                      723.4(2)
_cell_formula_units_Z             2
_cell_measurement_temperature     230(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?

_exptl_crystal_description        prismatic
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.5
_exptl_crystal_size_mid           0.35
_exptl_crystal_size_min           0.3
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.264
_exptl_crystal_density_method     ?
_exptl_crystal_F_000              296
_exptl_absorpt_coefficient_mu     0.701
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?

_exptl_special_details
;
?
;

_diffrn_ambient_temperature       230(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device        'Rigaku afc7r'
_diffrn_measurement_method        ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             4655
_diffrn_reflns_av_R_equivalents   0.0601
_diffrn_reflns_av_sigmaI/netI     0.0336
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -6
_diffrn_reflns_limit_l_max        9
_diffrn_reflns_theta_min          3.77
_diffrn_reflns_theta_max          67.93
_reflns_number_total              2627
_reflns_number_observed           2534
_reflns_observed_criterion        >2sigma(I)

_computing_data_collection        'Rigaku afc7r'
_computing_cell_refinement        'Rigaku afc7r'
_computing_data_reduction         ?
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics     SHELXTL
_computing_publication_material   ?

_refine_special_details
;
Refinement on F^2^ for ALL reflections except for 10 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^)+(0.0584P)^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      SHELXL
_refine_ls_extinction_coef        0.0135(43)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns          2617
_refine_ls_number_parameters      182
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0449
_refine_ls_R_factor_obs           0.0432
_refine_ls_wR_factor_all          0.2064
_refine_ls_wR_factor_obs          0.1907
_refine_ls_goodness_of_fit_all    2.864
_refine_ls_goodness_of_fit_obs    2.896
_refine_ls_restrained_S_all       3.090
_refine_ls_restrained_S_obs       2.896
_refine_ls_shift/esd_max          0.041
_refine_ls_shift/esd_mean         0.010

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
O1 O 0.32200(14) 0.92029(9) 0.69016(14) 0.0424(4) Uani 1 d . .
O2 O 0.79186(12) 0.93118(9) 0.64720(12) 0.0374(3) Uani 1 d . .
O3 O 0.70063(11) 0.82848(8) 0.36849(12) 0.0325(3) Uani 1 d . .
N1 N 0.50543(13) 0.86344(9) 0.52737(13) 0.0279(3) Uani 1 d . .
C1 C 0.4488(2) 0.88594(11) 0.6915(2) 0.0316(4) Uani 1 d . .
C2 C 0.5340(2) 0.84892(14) 0.8566(2) 0.0397(4) Uani 1 d . .
C3 C 0.4437(2) 0.72432(14) 0.8625(2) 0.0408(4) Uani 1 d . .
C4 C 0.4594(2) 0.63530(14) 0.7077(2) 0.0422(4) Uani 1 d . .
C5 C 0.2918(2) 0.57508(13) 0.5770(2) 0.0451(4) Uani 1 d . .
C6 C 0.2053(2) 0.64795(12) 0.4631(2) 0.0376(4) Uani 1 d . .
C7 C 0.3020(2) 0.69839(12) 0.3201(2) 0.0344(4) Uani 1 d . .
C8 C 0.3758(2) 0.82674(11) 0.3593(2) 0.0302(4) Uani 1 d . .
C9 C 0.6774(2) 0.87839(10) 0.5247(2) 0.0282(4) Uani 1 d . .
C10 C 0.8776(2) 0.85742(13) 0.3440(2) 0.0397(4) Uani 1 d . .
C11 C 0.8901(2) 0.78455(11) 0.1769(2) 0.0306(4) Uani 1 d . .
C12 C 0.8199(2) 0.66743(13) 0.1467(2) 0.0397(4) Uani 1 d . .
C13 C 0.8407(2) 0.60173(15) -0.0053(3) 0.0547(5) Uani 1 d . .
C14 C 0.9284(2) 0.6529(2) -0.1288(2) 0.0578(6) Uani 1 d . .
C15 C 0.9962(2) 0.7684(2) -0.0998(2) 0.0499(5) Uani 1 d . .
C16 C 0.9780(2) 0.83433(13) 0.0522(2) 0.0382(4) Uani 1 d . .
H1 H 0.5203 0.9000 0.9596 0.058 Uiso 1 d . .
H2 H 0.6449 0.8400 0.8495 0.058 Uiso 1 d . .
H3 H 0.3272 0.7200 0.8627 0.058 Uiso 1 d . .
H4 H 0.4889 0.7000 0.9717 0.058 Uiso 1 d . .
H5 H 0.5017 0.5800 0.7661 0.058 Uiso 1 d . .
H6 H 0.5448 0.6800 0.6385 0.058 Uiso 1 d . .
H7 H 0.2177 0.5400 0.6513 0.058 Uiso 1 d . .
H8 H 0.3159 0.5200 0.4975 0.058 Uiso 1 d . .
H9 H 0.1822 0.7000 0.5390 0.058 Uiso 1 d . .
H10 H 0.0906 0.6000 0.3966 0.058 Uiso 1 d . .
H11 H 0.2329 0.6800 0.2084 0.058 Uiso 1 d . .
H12 H 0.3947 0.6600 0.3081 0.058 Uiso 1 d . .
H13 H 0.2913 0.8600 0.3751 0.058 Uiso 1 d . .
H14 H 0.4301 0.8600 0.2601 0.058 Uiso 1 d . .
H15 H 0.9198 0.9400 0.3339 0.058 Uiso 1 d . .
H16 H 0.9405 0.8400 0.4490 0.058 Uiso 1 d . .
H17 H 0.7515 0.6400 0.2308 0.058 Uiso 1 d . .
H18 H 0.7933 0.5200 -0.0247 0.058 Uiso 1 d . .
H19 H 0.9390 0.6000 -0.2354 0.058 Uiso 1 d . .
H20 H 1.0573 0.8000 -0.1905 0.058 Uiso 1 d . .
H21 H 1.0250 0.9200 0.0642 0.058 Uiso 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
O1 0.0462(7) 0.0426(6) 0.0479(6) 0.0094(5) 0.0239(5) 0.0188(5)
O2 0.0291(6) 0.0426(6) 0.0348(5) 0.0004(4) 0.0063(4) 0.0008(4)
O3 0.0237(6) 0.0357(6) 0.0357(6) -0.0013(4) 0.0126(4) 0.0020(4)
N1 0.0253(6) 0.0283(6) 0.0299(6) 0.0040(4) 0.0101(4) 0.0037(4)
C1 0.0327(7) 0.0270(7) 0.0350(7) 0.0028(5) 0.0145(5) 0.0036(5)
C2 0.0386(8) 0.0510(9) 0.0280(7) 0.0036(6) 0.0108(5) 0.0071(6)
C3 0.0364(8) 0.0545(9) 0.0375(8) 0.0188(6) 0.0122(6) 0.0147(7)
C4 0.0401(8) 0.0424(8) 0.0502(9) 0.0168(6) 0.0090(6) 0.0177(6)
C5 0.0444(9) 0.0331(7) 0.0579(9) 0.0152(7) 0.0095(7) 0.0067(6)
C6 0.0291(7) 0.0323(7) 0.0487(8) 0.0097(6) 0.0052(6) 0.0027(6)
C7 0.0291(7) 0.0372(8) 0.0336(7) 0.0007(5) 0.0031(5) 0.0064(6)
C8 0.0272(7) 0.0355(7) 0.0294(6) 0.0073(5) 0.0073(5) 0.0087(5)
C9 0.0260(7) 0.0249(6) 0.0319(6) 0.0032(5) 0.0075(5) 0.0024(5)
C10 0.0222(7) 0.0472(8) 0.0447(8) -0.0036(6) 0.0128(5) 0.0003(6)
C11 0.0211(6) 0.0353(7) 0.0359(7) 0.0046(5) 0.0065(5) 0.0081(5)
C12 0.0333(8) 0.0367(8) 0.0496(8) 0.0087(6) 0.0091(6) 0.0081(6)
C13 0.0408(9) 0.0410(9) 0.0751(11) -0.0136(8) 0.0021(8) 0.0135(7)
C14 0.0406(9) 0.0841(14) 0.0451(9) -0.0187(8) 0.0045(7) 0.0253(9)
C15 0.0382(9) 0.0798(12) 0.0397(8) 0.0140(8) 0.0146(6) 0.0236(8)
C16 0.0302(7) 0.0449(8) 0.0447(8) 0.0132(6) 0.0117(5) 0.0141(6)

_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
O1 C1 1.210(2) . ?
O2 C9 1.212(2) . ?
O3 C9 1.333(2) . ?
O3 C10 1.4591(14) . ?
N1 C9 1.384(2) . ?
N1 C1 1.418(2) . ?
N1 C8 1.478(2) . ?
C1 C2 1.508(2) . ?
C2 C3 1.538(2) . ?
C3 C4 1.551(2) . ?
C4 C5 1.533(2) . ?
C5 C6 1.527(2) . ?
C6 C7 1.545(2) . ?
C7 C8 1.519(2) . ?
C10 C11 1.497(2) . ?
C11 C12 1.389(2) . ?
C11 C16 1.389(2) . ?
C12 C13 1.387(2) . ?
C13 C14 1.387(3) . ?
C14 C15 1.368(3) . ?
C15 C16 1.380(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
C9 O3 C10 113.85(9) . . ?
C9 N1 C1 120.84(11) . . ?
C9 N1 C8 121.15(9) . . ?
C1 N1 C8 117.99(10) . . ?
O1 C1 N1 119.44(12) . . ?
O1 C1 C2 121.95(12) . . ?
N1 C1 C2 117.94(11) . . ?
C1 C2 C3 109.19(12) . . ?
C2 C3 C4 115.54(11) . . ?
C5 C4 C3 114.99(12) . . ?
C6 C5 C4 117.45(12) . . ?
C5 C6 C7 115.71(12) . . ?
C8 C7 C6 114.83(11) . . ?
N1 C8 C7 112.41(10) . . ?
O2 C9 O3 124.42(11) . . ?
O2 C9 N1 124.48(11) . . ?
O3 C9 N1 111.10(10) . . ?
O3 C10 C11 108.45(10) . . ?
C12 C11 C16 119.27(13) . . ?
C12 C11 C10 121.22(12) . . ?
C16 C11 C10 119.48(12) . . ?
C13 C12 C11 119.73(14) . . ?
C12 C13 C14 120.2(2) . . ?
C15 C14 C13 120.00(14) . . ?
C14 C15 C16 120.2(2) . . ?
C15 C16 C11 120.53(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
C9 N1 C1 O1 148.33(13) . . . . ?
C8 N1 C1 O1 -30.0(2) . . . . ?
C9 N1 C1 C2 -40.9(2) . . . . ?
C8 N1 C1 C2 140.78(12) . . . . ?
O1 C1 C2 C3 84.0(2) . . . . ?
N1 C1 C2 C3 -86.58(14) . . . . ?
C1 C2 C3 C4 65.30(15) . . . . ?
C2 C3 C4 C5 -113.52(14) . . . . ?
C3 C4 C5 C6 64.7(2) . . . . ?
C4 C5 C6 C7 67.2(2) . . . . ?
C5 C6 C7 C8 -110.50(14) . . . . ?
C9 N1 C8 C7 93.71(13) . . . . ?
C1 N1 C8 C7 -87.95(13) . . . . ?
C6 C7 C8 N1 62.52(13) . . . . ?
C10 O3 C9 O2 -9.2(2) . . . . ?
C10 O3 C9 N1 169.91(11) . . . . ?
C1 N1 C9 O2 -15.3(2) . . . . ?
C8 N1 C9 O2 162.94(12) . . . . ?
C1 N1 C9 O3 165.56(11) . . . . ?
C8 N1 C9 O3 -16.16(15) . . . . ?
C9 O3 C10 C11 172.50(11) . . . . ?
O3 C10 C11 C12 -48.8(2) . . . . ?
O3 C10 C11 C16 133.11(12) . . . . ?
C16 C11 C12 C13 1.1(2) . . . . ?
C10 C11 C12 C13 -176.97(13) . . . . ?
C11 C12 C13 C14 -1.3(2) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C14 C15 C16 C11 -0.3(2) . . . . ?
C12 C11 C16 C15 -0.3(2) . . . . ?
C10 C11 C16 C15 177.77(13) . . . . ?

_refine_diff_density_max    0.244
_refine_diff_density_min   -0.220
_refine_diff_density_rms    0.040

