#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/24/8102411.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102411
loop_
_publ_author_name
'Richard J. Staples'
'Julian A. Gingold'
_publ_section_title
;
 Crystal structure of isopropyl-N-(3-chlorophenyl)carbamate,
 C10H12ClNO2, Chloropropham
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              121
_journal_volume                  224
_journal_year                    2009
_chemical_compound_source        'Purchased from Aldrich'
_chemical_formula_moiety         'C10 H12 Cl N O2'
_chemical_formula_sum            'C10 H12 Cl N O2'
_chemical_formula_weight         213.66
_chemical_name_common            Chloropropham
_chemical_name_systematic        Isopropyl-N-(3-chlorophenyl)carbamate
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            24
_cell_length_a                   20.935(5)
_cell_length_b                   13.964(3)
_cell_length_c                   22.386(5)
_cell_measurement_reflns_used    5419
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.17
_cell_measurement_theta_min      2.43
_cell_volume                     6544(3)
_computing_cell_refinement       'Bruker (1997) SMART V5.054[12]'
_computing_data_collection       'Bruker (1997) SMART V5.054[12]'
_computing_data_reduction        'Bruker (2003) SAINT V6.25[13]'
_computing_molecular_graphics    'Bruker (2000) SHELXTL V6.14[14]'
_computing_publication_material  'Bruker (2000) SHELXTL V6.14[14]'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)[14]'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)[14]'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       'ω, 0.3 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            51968
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.82
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Chunk
_exptl_crystal_F_000             2688
_exptl_crystal_recrystallization_method 'Sublimation under mild conditions.'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         8138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0590P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                5568
_reflns_number_total             8138
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2514.cff
_cod_data_source_block           HU21
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               8102411
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
Cl1A Cl 0.48396(2) -0.07549(4) 0.67058(2) 0.06643(15) Uani 1 1 d . . .
O1A O 0.17389(5) -0.00673(7) 0.76921(4) 0.0424(3) Uani 1 1 d . . .
O2A O 0.14724(5) 0.03427(8) 0.67459(4) 0.0425(3) Uani 1 1 d . . .
N1A N 0.24752(6) -0.00313(9) 0.69330(6) 0.0357(3) Uani 1 1 d . . .
H1A H 0.2508(7) 0.0117(11) 0.6597(8) 0.038(5) Uiso 1 1 d . . .
C1A C 0.18869(7) 0.00729(10) 0.71725(6) 0.0355(3) Uani 1 1 d . . .
C2A C 0.30306(7) -0.03587(10) 0.72211(6) 0.0351(3) Uani 1 1 d . . .
C3A C 0.35871(7) -0.03899(11) 0.68786(7) 0.0369(3) Uani 1 1 d . . .
H2A H 0.3583(8) -0.0177(11) 0.6486(8) 0.042(4) Uiso 1 1 d . . .
C4A C 0.41454(8) -0.07167(11) 0.71350(7) 0.0431(4) Uani 1 1 d . . .
C5A C 0.41725(9) -0.10216(13) 0.77213(8) 0.0508(4) Uani 1 1 d . . .
H3A H 0.4575(8) -0.1248(11) 0.7886(8) 0.049(5) Uiso 1 1 d . . .
C6A C 0.36190(9) -0.09915(13) 0.80544(8) 0.0544(5) Uani 1 1 d . . .
H4A H 0.3640(8) -0.1227(13) 0.8465(9) 0.056(5) Uiso 1 1 d . . .
C7A C 0.30497(9) -0.06614(12) 0.78164(7) 0.0459(4) Uani 1 1 d . . .
H5A H 0.2678(8) -0.0633(11) 0.8043(7) 0.041(4) Uiso 1 1 d . . .
C8A C 0.08097(8) 0.04986(13) 0.69342(8) 0.0514(4) Uani 1 1 d . . .
H6A H 0.0737(8) 0.0025(13) 0.7233(8) 0.055(5) Uiso 1 1 d . . .
C9A C 0.07451(13) 0.14934(19) 0.71801(12) 0.0749(7) Uani 1 1 d . . .
H7A H 0.0308(12) 0.1627(17) 0.7291(11) 0.095(8) Uiso 1 1 d . . .
H8A H 0.0847(13) 0.198(2) 0.6898(13) 0.113(10) Uiso 1 1 d . . .
H9A H 0.1017(12) 0.1611(19) 0.7543(13) 0.111(10) Uiso 1 1 d . . .
C10A C 0.04123(10) 0.0312(2) 0.63886(10) 0.0653(6) Uani 1 1 d . . .
H11A H -0.0035(10) 0.0378(13) 0.6474(9) 0.067(6) Uiso 1 1 d . . .
H10A H 0.0533(10) 0.0776(15) 0.6092(9) 0.072(6) Uiso 1 1 d . . .
H12A H 0.0471(10) -0.0335(16) 0.6248(9) 0.075(7) Uiso 1 1 d . . .
Cl1B Cl 0.48511(2) 0.21788(5) 0.64008(3) 0.08243(19) Uani 1 1 d . . .
O1B O 0.27990(5) 0.06521(7) 0.57355(4) 0.0403(2) Uani 1 1 d . . .
O2B O 0.22144(5) 0.05521(7) 0.48840(4) 0.0412(2) Uani 1 1 d . . .
N1B N 0.31141(6) 0.13476(9) 0.48574(6) 0.0384(3) Uani 1 1 d . . .
H1B H 0.2982(8) 0.1419(11) 0.4506(8) 0.043(5) Uiso 1 1 d . . .
C1B C 0.27176(7) 0.08294(10) 0.52092(6) 0.0339(3) Uani 1 1 d . . .
C2B C 0.37069(7) 0.17421(10) 0.50067(7) 0.0378(3) Uani 1 1 d . . .
C3B C 0.39553(7) 0.17465(11) 0.55810(8) 0.0411(4) Uani 1 1 d . . .
H2B H 0.3723(8) 0.1455(11) 0.5897(7) 0.042(4) Uiso 1 1 d . . .
C4B C 0.45378(8) 0.21818(12) 0.56796(9) 0.0528(4) Uani 1 1 d . . .
C5B C 0.48784(9) 0.26141(14) 0.52275(13) 0.0669(6) Uani 1 1 d . . .
H3B H 0.5275(9) 0.2922(14) 0.5333(8) 0.065(6) Uiso 1 1 d . . .
C6B C 0.46308(10) 0.25911(14) 0.46604(13) 0.0707(7) Uani 1 1 d . . .
H4B H 0.4841(10) 0.2863(15) 0.4343(10) 0.072(6) Uiso 1 1 d . . .
C7B C 0.40515(9) 0.21581(13) 0.45409(10) 0.0539(5) Uani 1 1 d . . .
H5B H 0.3883(9) 0.2124(13) 0.4163(8) 0.054(5) Uiso 1 1 d . . .
C8B C 0.16964(7) 0.00626(11) 0.51999(7) 0.0415(3) Uani 1 1 d . . .
H6B H 0.1640(7) 0.0401(10) 0.5571(7) 0.032(4) Uiso 1 1 d . . .
C9B C 0.11236(10) 0.01719(18) 0.47935(11) 0.0633(5) Uani 1 1 d . . .
H8B H 0.0713(11) -0.0110(16) 0.4978(9) 0.087(7) Uiso 1 1 d . . .
H9B H 0.1213(10) -0.0151(16) 0.4420(11) 0.087(7) Uiso 1 1 d . . .
H7B H 0.1046(10) 0.0859(16) 0.4736(10) 0.079(7) Uiso 1 1 d . . .
C10B C 0.18690(10) -0.09608(13) 0.53186(11) 0.0582(5) Uani 1 1 d . . .
H12B H 0.2280(9) -0.0999(13) 0.5556(8) 0.062(5) Uiso 1 1 d . . .
H10B H 0.1939(10) -0.1275(15) 0.4948(10) 0.073(6) Uiso 1 1 d . . .
H11B H 0.1521(10) -0.1251(15) 0.5515(9) 0.071(6) Uiso 1 1 d . . .
Cl1C Cl 0.15258(3) 0.26048(3) 0.574885(19) 0.06125(14) Uani 1 1 d . . .
O1C O 0.26625(5) 0.23374(8) 0.37705(5) 0.0451(3) Uani 1 1 d . . .
O2C O 0.26572(5) 0.31137(7) 0.28823(4) 0.0449(3) Uani 1 1 d . . .
N1C N 0.19753(7) 0.35690(10) 0.35682(6) 0.0439(3) Uani 1 1 d . . .
H1C H 0.1887(8) 0.3971(12) 0.3309(7) 0.042(5) Uiso 1 1 d . . .
C1C C 0.24521(7) 0.29515(11) 0.34420(6) 0.0370(3) Uani 1 1 d . . .
C2C C 0.16330(7) 0.36775(10) 0.41044(6) 0.0357(3) Uani 1 1 d . . .
C3C C 0.17320(8) 0.31113(11) 0.46052(7) 0.0388(3) Uani 1 1 d . . .
H2C H 0.2037(8) 0.2624(11) 0.4606(7) 0.043(4) Uiso 1 1 d . . .
C4C C 0.13846(8) 0.33103(11) 0.51180(6) 0.0405(3) Uani 1 1 d . . .
C5C C 0.09404(8) 0.40275(12) 0.51452(7) 0.0443(4) Uani 1 1 d . . .
H3C H 0.0718(8) 0.4136(11) 0.5495(8) 0.048(5) Uiso 1 1 d . . .
C6C C 0.08337(8) 0.45607(12) 0.46363(8) 0.0450(4) Uani 1 1 d . . .
H4C H 0.0515(8) 0.5044(13) 0.4644(7) 0.051(5) Uiso 1 1 d . . .
C7C C 0.11745(8) 0.43977(11) 0.41219(7) 0.0415(4) Uani 1 1 d . . .
H5C H 0.1094(8) 0.4769(12) 0.3787(8) 0.047(5) Uiso 1 1 d . . .
C8C C 0.31970(9) 0.25461(12) 0.26706(7) 0.0465(4) Uani 1 1 d . . .
H6C H 0.3167(7) 0.1915(12) 0.2859(7) 0.046(4) Uiso 1 1 d . . .
C9C C 0.31007(13) 0.24602(15) 0.20049(9) 0.0592(5) Uani 1 1 d . . .
H9C H 0.2678(10) 0.2189(13) 0.1906(8) 0.057(5) Uiso 1 1 d . . .
H8C H 0.3117(9) 0.3075(15) 0.1815(8) 0.059(5) Uiso 1 1 d . . .
H7C H 0.3436(10) 0.2084(16) 0.1836(9) 0.072(6) Uiso 1 1 d . . .
C10C C 0.38084(10) 0.30377(16) 0.28438(11) 0.0597(5) Uani 1 1 d . . .
H11C H 0.4162(10) 0.2677(14) 0.2701(9) 0.068(6) Uiso 1 1 d . . .
H12C H 0.3807(10) 0.3155(15) 0.3273(10) 0.073(6) Uiso 1 1 d . . .
H10C H 0.3849(10) 0.3625(16) 0.2633(10) 0.077(6) Uiso 1 1 d . . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C1A O2A C8A 116.62(12) . . ?
C1A N1A C2A 127.37(13) . . ?
C1A N1A H1A 115.6(12) . . ?
C2A N1A H1A 117.0(12) . . ?
O1A C1A O2A 123.96(14) . . ?
O1A C1A N1A 126.34(14) . . ?
O2A C1A N1A 109.68(12) . . ?
C3A C2A C7A 119.35(14) . . ?
C3A C2A N1A 116.67(13) . . ?
C7A C2A N1A 123.97(14) . . ?
C4A C3A C2A 119.28(14) . . ?
C4A C3A H2A 120.5(10) . . ?
C2A C3A H2A 120.2(10) . . ?
C3A C4A C5A 122.15(16) . . ?
C3A C4A Cl1A 119.15(12) . . ?
C5A C4A Cl1A 118.70(13) . . ?
C6A C5A C4A 118.05(16) . . ?
C6A C5A H3A 122.3(10) . . ?
C4A C5A H3A 119.7(10) . . ?
C5A C6A C7A 121.70(16) . . ?
C5A C6A H4A 117.4(11) . . ?
C7A C6A H4A 120.9(11) . . ?
C6A C7A C2A 119.47(17) . . ?
C6A C7A H5A 121.7(10) . . ?
C2A C7A H5A 118.8(10) . . ?
O2A C8A C9A 109.16(17) . . ?
O2A C8A C10A 105.35(14) . . ?
C9A C8A C10A 114.17(19) . . ?
O2A C8A H6A 104.5(10) . . ?
C9A C8A H6A 111.8(10) . . ?
C10A C8A H6A 111.2(11) . . ?
C8A C9A H7A 111.0(15) . . ?
C8A C9A H8A 113.2(17) . . ?
H7A C9A H8A 104(2) . . ?
C8A C9A H9A 113.3(15) . . ?
H7A C9A H9A 107(2) . . ?
H8A C9A H9A 107(2) . . ?
C8A C10A H11A 111.3(12) . . ?
C8A C10A H10A 107.4(12) . . ?
H11A C10A H10A 109.2(17) . . ?
C8A C10A H12A 110.9(13) . . ?
H11A C10A H12A 106.2(17) . . ?
H10A C10A H12A 111.9(17) . . ?
C1B O2B C8B 117.10(11) . . ?
C1B N1B C2B 128.00(13) . . ?
C1B N1B H1B 113.9(11) . . ?
C2B N1B H1B 118.0(11) . . ?
O1B C1B O2B 125.37(13) . . ?
O1B C1B N1B 125.91(14) . . ?
O2B C1B N1B 108.72(12) . . ?
C3B C2B C7B 119.82(16) . . ?
C3B C2B N1B 123.79(13) . . ?
C7B C2B N1B 116.39(16) . . ?
C4B C3B C2B 118.78(16) . . ?
C4B C3B H2B 121.4(10) . . ?
C2B C3B H2B 119.8(10) . . ?
C5B C4B C3B 122.20(19) . . ?
C5B C4B Cl1B 119.14(16) . . ?
C3B C4B Cl1B 118.66(15) . . ?
C6B C5B C4B 118.31(19) . . ?
C6B C5B H3B 124.2(12) . . ?
C4B C5B H3B 117.5(12) . . ?
C5B C6B C7B 121.4(2) . . ?
C5B C6B H4B 121.7(13) . . ?
C7B C6B H4B 116.9(14) . . ?
C6B C7B C2B 119.4(2) . . ?
C6B C7B H5B 122.6(12) . . ?
C2B C7B H5B 118.0(12) . . ?
O2B C8B C10B 110.63(14) . . ?
O2B C8B C9B 104.45(14) . . ?
C10B C8B C9B 113.21(17) . . ?
O2B C8B H6B 106.2(8) . . ?
C10B C8B H6B 110.2(9) . . ?
C9B C8B H6B 111.8(9) . . ?
C8B C9B H8B 112.4(12) . . ?
C8B C9B H9B 108.6(13) . . ?
H8B C9B H9B 109.2(17) . . ?
C8B C9B H7B 108.0(13) . . ?
H8B C9B H7B 106.8(18) . . ?
H9B C9B H7B 111.9(19) . . ?
C8B C10B H12B 110.4(10) . . ?
C8B C10B H10B 108.8(13) . . ?
H12B C10B H10B 107.6(17) . . ?
C8B C10B H11B 107.9(12) . . ?
H12B C10B H11B 113.0(16) . . ?
H10B C10B H11B 109.1(18) . . ?
C1C O2C C8C 117.30(12) . . ?
C1C N1C C2C 128.66(13) . . ?
C1C N1C H1C 116.9(11) . . ?
C2C N1C H1C 114.2(11) . . ?
O1C C1C O2C 124.65(14) . . ?
O1C C1C N1C 126.43(14) . . ?
O2C C1C N1C 108.90(12) . . ?
C3C C2C C7C 119.49(14) . . ?
C3C C2C N1C 123.53(14) . . ?
C7C C2C N1C 116.98(13) . . ?
C4C C3C C2C 118.44(15) . . ?
C4C C3C H2C 120.2(10) . . ?
C2C C3C H2C 121.3(10) . . ?
C5C C4C C3C 122.68(15) . . ?
C5C C4C Cl1C 119.46(12) . . ?
C3C C4C Cl1C 117.86(12) . . ?
C4C C5C C6C 117.93(15) . . ?
C4C C5C H3C 120.1(10) . . ?
C6C C5C H3C 122.0(10) . . ?
C7C C6C C5C 121.26(16) . . ?
C7C C6C H4C 119.9(10) . . ?
C5C C6C H4C 118.8(10) . . ?
C6C C7C C2C 120.13(15) . . ?
C6C C7C H5C 119.3(10) . . ?
C2C C7C H5C 120.5(10) . . ?
O2C C8C C10C 109.12(15) . . ?
O2C C8C C9C 105.10(15) . . ?
C10C C8C C9C 113.89(17) . . ?
O2C C8C H6C 107.4(9) . . ?
C10C C8C H6C 110.8(9) . . ?
C9C C8C H6C 110.2(10) . . ?
C8C C9C H9C 111.8(11) . . ?
C8C C9C H8C 111.2(11) . . ?
H9C C9C H8C 106.1(16) . . ?
C8C C9C H7C 109.7(12) . . ?
H9C C9C H7C 111.0(16) . . ?
H8C C9C H7C 106.9(17) . . ?
C8C C10C H11C 109.6(12) . . ?
C8C C10C H12C 109.2(12) . . ?
H11C C10C H12C 115.0(18) . . ?
C8C C10C H10C 110.1(13) . . ?
H11C C10C H10C 102.7(17) . . ?
H12C C10C H10C 110.2(18) . . ?
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
Cl1A C4A 1.7431(17) . ?
O1A C1A 1.2196(16) . ?
O2A C1A 1.3442(18) . ?
O2A C8A 1.4664(19) . ?
N1A C1A 1.3510(19) . ?
N1A C2A 1.4060(19) . ?
N1A H1A 0.783(17) . ?
C2A C3A 1.395(2) . ?
C2A C7A 1.399(2) . ?
C3A C4A 1.380(2) . ?
C3A H2A 0.928(17) . ?
C4A C5A 1.381(2) . ?
C5A C6A 1.379(3) . ?
C5A H3A 0.973(17) . ?
C6A C7A 1.385(2) . ?
C6A H4A 0.977(19) . ?
C7A H5A 0.930(16) . ?
C8A C9A 1.500(3) . ?
C8A C10A 1.500(3) . ?
C8A H6A 0.952(18) . ?
C9A H7A 0.97(3) . ?
C9A H8A 0.95(3) . ?
C9A H9A 1.00(3) . ?
C10A H11A 0.96(2) . ?
C10A H10A 0.96(2) . ?
C10A H12A 0.96(2) . ?
Cl1B C4B 1.743(2) . ?
O1B C1B 1.2158(16) . ?
O2B C1B 1.3377(17) . ?
O2B C8B 1.4642(18) . ?
N1B C1B 1.3539(18) . ?
N1B C2B 1.398(2) . ?
N1B H1B 0.841(17) . ?
C2B C3B 1.387(2) . ?
C2B C7B 1.395(2) . ?
C3B C4B 1.380(2) . ?
C3B H2B 0.951(16) . ?
C4B C5B 1.377(3) . ?
C5B C6B 1.372(3) . ?
C5B H3B 0.96(2) . ?
C6B C7B 1.381(3) . ?
C6B H4B 0.92(2) . ?
C7B H5B 0.918(18) . ?
C8B C10B 1.498(3) . ?
C8B C9B 1.513(2) . ?
C8B H6B 0.963(15) . ?
C9B H8B 1.03(2) . ?
C9B H9B 0.97(2) . ?
C9B H7B 0.98(2) . ?
C10B H12B 1.01(2) . ?
C10B H10B 0.95(2) . ?
C10B H11B 0.94(2) . ?
Cl1C C4C 1.7471(16) . ?
O1C C1C 1.2125(17) . ?
O2C C1C 1.3438(17) . ?
O2C C8C 1.4593(19) . ?
N1C C1C 1.3491(19) . ?
N1C C2C 1.4061(19) . ?
N1C H1C 0.828(17) . ?
C2C C3C 1.387(2) . ?
C2C C7C 1.391(2) . ?
C3C C4C 1.387(2) . ?
C3C H2C 0.933(16) . ?
C4C C5C 1.368(2) . ?
C5C C6C 1.379(2) . ?
C5C H3C 0.924(17) . ?
C6C C7C 1.374(2) . ?
C6C H4C 0.949(18) . ?
C7C H5C 0.926(17) . ?
C8C C10C 1.503(3) . ?
C8C C9C 1.509(3) . ?
C8C H6C 0.979(17) . ?
C9C H9C 0.99(2) . ?
C9C H8C 0.96(2) . ?
C9C H7C 0.96(2) . ?
C10C H11C 0.95(2) . ?
C10C H12C 0.98(2) . ?
C10C H10C 0.95(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1A O1B 0.783(17) 2.156(17) 2.9253(17) 167.2(16) .
N1B H1B O1C 0.841(17) 2.190(17) 2.9535(17) 150.9(15) .
N1C H1C O1A 0.828(17) 2.085(18) 2.9100(18) 174.3(16) 7_565
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
C8A O2A C1A O1A 1.8(2) . . . . ?
C8A O2A C1A N1A -179.32(13) . . . . ?
C2A N1A C1A O1A 2.9(2) . . . . ?
C2A N1A C1A O2A -175.91(13) . . . . ?
C1A N1A C2A C3A -179.05(13) . . . . ?
C1A N1A C2A C7A 2.0(2) . . . . ?
C7A C2A C3A C4A -0.2(2) . . . . ?
N1A C2A C3A C4A -179.17(13) . . . . ?
C2A C3A C4A C5A 0.4(2) . . . . ?
C2A C3A C4A Cl1A 179.99(11) . . . . ?
C3A C4A C5A C6A -0.1(2) . . . . ?
Cl1A C4A C5A C6A -179.71(14) . . . . ?
C4A C5A C6A C7A -0.4(3) . . . . ?
C5A C6A C7A C2A 0.7(3) . . . . ?
C3A C2A C7A C6A -0.4(2) . . . . ?
N1A C2A C7A C6A 178.58(15) . . . . ?
C1A O2A C8A C9A 83.88(19) . . . . ?
C1A O2A C8A C10A -153.11(16) . . . . ?
C8B O2B C1B O1B 5.3(2) . . . . ?
C8B O2B C1B N1B -174.00(12) . . . . ?
C2B N1B C1B O1B 3.6(2) . . . . ?
C2B N1B C1B O2B -177.11(13) . . . . ?
C1B N1B C2B C3B -7.5(2) . . . . ?
C1B N1B C2B C7B 173.28(15) . . . . ?
C7B C2B C3B C4B 1.2(2) . . . . ?
N1B C2B C3B C4B -178.09(14) . . . . ?
C2B C3B C4B C5B 0.2(2) . . . . ?
C2B C3B C4B Cl1B -179.57(11) . . . . ?
C3B C4B C5B C6B -1.2(3) . . . . ?
Cl1B C4B C5B C6B 178.59(15) . . . . ?
C4B C5B C6B C7B 0.8(3) . . . . ?
C5B C6B C7B C2B 0.6(3) . . . . ?
C3B C2B C7B C6B -1.6(2) . . . . ?
N1B C2B C7B C6B 177.75(16) . . . . ?
C1B O2B C8B C10B -78.17(18) . . . . ?
C1B O2B C8B C9B 159.69(15) . . . . ?
C8C O2C C1C O1C -3.8(2) . . . . ?
C8C O2C C1C N1C 177.03(13) . . . . ?
C2C N1C C1C O1C 2.9(3) . . . . ?
C2C N1C C1C O2C -177.96(14) . . . . ?
C1C N1C C2C C3C -2.0(3) . . . . ?
C1C N1C C2C C7C 177.90(15) . . . . ?
C7C C2C C3C C4C -2.5(2) . . . . ?
N1C C2C C3C C4C 177.32(14) . . . . ?
C2C C3C C4C C5C 1.4(2) . . . . ?
C2C C3C C4C Cl1C -178.83(11) . . . . ?
C3C C4C C5C C6C 0.8(2) . . . . ?
Cl1C C4C C5C C6C -178.99(12) . . . . ?
C4C C5C C6C C7C -1.8(2) . . . . ?
C5C C6C C7C C2C 0.7(2) . . . . ?
C3C C2C C7C C6C 1.6(2) . . . . ?
N1C C2C C7C C6C -178.31(14) . . . . ?
C1C O2C C8C C10C -87.15(17) . . . . ?
C1C O2C C8C C9C 150.34(14) . . . . ?
