#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2203338.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_2203338
loop_
_publ_author_name
'Liu, Xin-Gang'
'Feng, Ya-Qing'
'Li, Xiao-Fang'
'Liang, Zu-Pei'
_publ_section_title
;
Ethyl
2-(2,4-dichlorobenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-
5H-thiazolo[3,2-a]pyrimidine-6-carboxylate dichloromethane solvate
;
_journal_issue                 3
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o344
_journal_page_last             o345
_journal_volume                60
_journal_year                  2004
_chemical_formula_analytical   ?
_chemical_formula_iupac        'C23 H18 Cl2 N2 O3 S, C H2 Cl2'
_chemical_formula_moiety       'C23 H18 Cl2 N2 O3 S, C H2 Cl2'
_chemical_formula_structural   ?
_chemical_formula_sum          'C24 H20 Cl4 N2 O3 S'
_chemical_formula_weight       558.28
_chemical_melting_point        .182E-180
_chemical_name_common          ?
_chemical_name_systematic
;
Ethyl
2-(2,4-dichlorobenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-
5H-thiazolo[3,2-a]pyrimidine-6-carboxylate dichloromethane solvate
;
_symmetry_cell_setting         Triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_cell_angle_alpha              84.546(7)
_cell_angle_beta               74.655(6)
_cell_angle_gamma              78.378(6)
_cell_formula_units_Z          2
_cell_length_a                 9.747(4)
_cell_length_b                 11.291(4)
_cell_length_c                 12.297(5)
_cell_measurement_reflns_used  1016
_cell_measurement_temperature  293(2)
_cell_measurement_theta_max    26.07
_cell_measurement_theta_min    2.20
_cell_volume                   1277.1(9)
_computing_cell_refinement     SMART
_computing_data_collection     'SMART (Bruker, 1997)'
_computing_data_reduction      'SAINT (Bruker, 1997)'
_computing_molecular_graphics  'SHELXTL (Bruker, 1997)'
_computing_publication_material SHELXTL
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature    293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method     '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source       'fine-focus sealed tube'
_diffrn_radiation_type         MoK\a
_diffrn_radiation_wavelength   0.71073
_diffrn_reflns_av_R_equivalents 0.0319
_diffrn_reflns_av_sigmaI/netI  0.0661
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_l_max     14
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_number          6583
_diffrn_reflns_reduction_process ?
_diffrn_reflns_theta_full      25.00
_diffrn_reflns_theta_max       25.00
_diffrn_reflns_theta_min       1.72
_diffrn_standards_decay_%      ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  0.575
_exptl_absorpt_correction_T_max 0.933
_exptl_absorpt_correction_T_min 0.777
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS, Bruker, 1997)'
_exptl_crystal_colour          colorless
_exptl_crystal_density_diffrn  1.452
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     block
_exptl_crystal_F_000           572
_exptl_crystal_size_max        0.22
_exptl_crystal_size_mid        0.16
_exptl_crystal_size_min        0.12
_exptl_crystal_size_rad        ?
_refine_diff_density_max       0.503
_refine_diff_density_min       -0.455
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack ?
_refine_ls_abs_structure_Rogers ?
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_all ?
_refine_ls_goodness_of_fit_ref 1.051
_refine_ls_hydrogen_treatment  constr
_refine_ls_matrix_type         full
_refine_ls_number_constraints  ?
_refine_ls_number_parameters   309
_refine_ls_number_reflns       4478
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    1.051
_refine_ls_restrained_S_obs    ?
_refine_ls_R_factor_all        0.1092
_refine_ls_R_factor_gt         0.0588
_refine_ls_shift/su_max        0.000
_refine_ls_shift/su_mean       0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0864P)^2^+0.2487P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_all       ?
_refine_ls_wR_factor_ref       0.1795
_reflns_number_gt              2711
_reflns_number_total           4478
_reflns_threshold_expression   I>2\s(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 0.31284(12) 0.21167(11) 0.97506(9) 0.0570(3) Uani d . 1 . . S
Cl1 0.26079(15) -0.29145(12) 0.96659(13) 0.0866(5) Uani d . 1 . . Cl
Cl2 -0.21001(13) -0.15015(14) 1.29760(10) 0.0810(5) Uani d . 1 . . Cl
O1 0.5779(3) -0.0232(3) 0.7739(2) 0.0559(8) Uani d . 1 . . O
O2 0.8771(5) 0.4473(4) 0.6447(3) 0.1065(15) Uani d . 1 . . O
O3 0.8904(3) 0.2702(3) 0.5744(2) 0.0573(8) Uani d . 1 . . O
N1 0.5409(3) 0.1799(3) 0.8048(2) 0.0414(8) Uani d . 1 . . N
N2 0.4691(4) 0.3797(3) 0.8725(3) 0.0546(9) Uani d . 1 . . N
C1 0.1000(5) 0.0240(4) 1.1163(4) 0.0613(12) Uani d . 1 . . C
H1 0.1219 0.1009 1.1133 0.074 Uiso calc R 1 . . H
C2 -0.0227(5) -0.0004(5) 1.1941(4) 0.0642(12) Uani d . 1 . . C
H2 -0.0820 0.0587 1.2420 0.077 Uiso calc R 1 . . H
C3 -0.0558(5) -0.1150(5) 1.1996(4) 0.0569(12) Uani d . 1 . . C
C4 0.0317(5) -0.2033(4) 1.1298(4) 0.0598(12) Uani d . 1 . . C
H4 0.0088 -0.2800 1.1345 0.072 Uiso calc R 1 . . H
C5 0.1546(5) -0.1765(4) 1.0523(3) 0.0536(11) Uani d . 1 . . C
C6 0.1938(4) -0.0611(4) 1.0411(3) 0.0455(10) Uani d . 1 . . C
C7 0.3213(4) -0.0366(4) 0.9557(3) 0.0483(10) Uani d . 1 . . C
H7 0.3751 -0.1039 0.9160 0.058 Uiso calc R 1 . . H
C8 0.3760(4) 0.0653(4) 0.9233(3) 0.0440(9) Uani d . 1 . . C
C9 0.5079(4) 0.0640(4) 0.8269(3) 0.0429(9) Uani d . 1 . . C
C10 0.4534(4) 0.2682(4) 0.8741(3) 0.0457(10) Uani d . 1 . . C
C11 0.5993(4) 0.4080(4) 0.7995(3) 0.0488(10) Uani d . 1 . . C
C12 0.6213(6) 0.5305(4) 0.8229(4) 0.0701(13) Uani d . 1 . . C
H12A 0.7146 0.5440 0.7791 0.105 Uiso calc R 1 . . H
H12B 0.6158 0.5336 0.9018 0.105 Uiso calc R 1 . . H
H12C 0.5474 0.5920 0.8029 0.105 Uiso calc R 1 . . H
C13 0.6887(4) 0.3316(4) 0.7206(3) 0.0443(9) Uani d . 1 . . C
C14 0.6453(4) 0.2147(3) 0.7007(3) 0.0412(9) Uani d . 1 . . C
H14 0.7318 0.1510 0.6872 0.049 Uiso calc R 1 . . H
C15 0.5798(4) 0.2250(3) 0.5999(3) 0.0421(9) Uani d . 1 . . C
C16 0.4818(5) 0.3279(4) 0.5802(4) 0.0558(11) Uani d . 1 . . C
H16 0.4591 0.3924 0.6276 0.067 Uiso calc R 1 . . H
C17 0.4177(5) 0.3357(5) 0.4910(4) 0.0673(13) Uani d . 1 . . C
H17 0.3517 0.4045 0.4791 0.081 Uiso calc R 1 . . H
C18 0.4525(6) 0.2405(5) 0.4199(4) 0.0725(15) Uani d . 1 . . C
H18 0.4094 0.2454 0.3602 0.087 Uiso calc R 1 . . H
C19 0.5490(6) 0.1398(5) 0.4365(4) 0.0709(14) Uani d . 1 . . C
H19 0.5723 0.0764 0.3879 0.085 Uiso calc R 1 . . H
C20 0.6132(5) 0.1315(4) 0.5266(4) 0.0608(12) Uani d . 1 . . C
H20 0.6793 0.0623 0.5375 0.073 Uiso calc R 1 . . H
C21 0.8248(5) 0.3592(4) 0.6451(4) 0.0536(11) Uani d . 1 . . C
C22 1.0221(5) 0.2864(5) 0.4892(4) 0.0655(13) Uani d . 1 . . C
H22A 1.0959 0.2974 0.5250 0.079 Uiso calc R 1 . . H
H22B 1.0027 0.3573 0.4406 0.079 Uiso calc R 1 . . H
C23 1.0718(6) 0.1761(6) 0.4223(5) 0.0948(18) Uani d . 1 . . C
H23A 1.0936 0.1070 0.4709 0.142 Uiso calc R 1 . . H
H23B 1.1570 0.1850 0.3638 0.142 Uiso calc R 1 . . H
H23C 0.9968 0.1650 0.3891 0.142 Uiso calc R 1 . . H
Cl3 0.75820(17) 0.38100(16) 0.31070(14) 0.1007(5) Uani d . 1 . . Cl
Cl4 1.0218(2) 0.4050(2) 0.13995(18) 0.1519(9) Uani d . 1 . . Cl
C24 0.8621(7) 0.4808(6) 0.2227(7) 0.125(3) Uani d . 1 . . C
H24A 0.8057 0.5287 0.1743 0.150 Uiso calc R 1 . . H
H24B 0.8840 0.5357 0.2691 0.150 Uiso calc R 1 . . H
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
S1 0.0482(6) 0.0654(7) 0.0518(6) -0.0183(5) 0.0041(5) -0.0066(5)
Cl1 0.0782(9) 0.0739(9) 0.1017(10) -0.0288(7) 0.0035(8) -0.0175(8)
Cl2 0.0536(7) 0.1247(12) 0.0630(8) -0.0368(7) -0.0073(6) 0.0268(7)
O1 0.0542(18) 0.0500(18) 0.0578(18) -0.0116(14) -0.0031(15) -0.0015(15)
O2 0.107(3) 0.100(3) 0.108(3) -0.073(3) 0.032(2) -0.033(2)
O3 0.0394(16) 0.0639(19) 0.0650(19) -0.0183(14) -0.0003(14) -0.0029(16)
N1 0.0355(17) 0.0469(19) 0.0404(17) -0.0113(14) -0.0050(14) 0.0001(15)
N2 0.051(2) 0.056(2) 0.056(2) -0.0160(17) -0.0030(17) -0.0131(18)
C1 0.061(3) 0.068(3) 0.056(3) -0.027(2) -0.006(2) -0.002(2)
C2 0.055(3) 0.085(4) 0.049(3) -0.018(2) -0.003(2) -0.004(2)
C3 0.042(2) 0.084(3) 0.047(2) -0.022(2) -0.014(2) 0.017(2)
C4 0.056(3) 0.068(3) 0.064(3) -0.031(2) -0.020(2) 0.015(2)
C5 0.050(3) 0.066(3) 0.051(2) -0.021(2) -0.017(2) 0.004(2)
C6 0.041(2) 0.058(3) 0.041(2) -0.0164(19) -0.0150(18) 0.0065(19)
C7 0.044(2) 0.057(3) 0.046(2) -0.0128(19) -0.0144(19) 0.003(2)
C8 0.040(2) 0.056(3) 0.038(2) -0.0147(18) -0.0106(18) 0.0018(18)
C9 0.043(2) 0.051(3) 0.038(2) -0.0140(19) -0.0143(18) 0.0005(19)
C10 0.037(2) 0.059(3) 0.042(2) -0.0110(19) -0.0090(18) -0.002(2)
C11 0.049(2) 0.048(2) 0.054(3) -0.0150(19) -0.018(2) 0.001(2)
C12 0.072(3) 0.061(3) 0.075(3) -0.021(2) -0.007(3) -0.012(2)
C13 0.045(2) 0.047(2) 0.046(2) -0.0157(18) -0.0145(19) 0.0017(19)
C14 0.034(2) 0.046(2) 0.044(2) -0.0106(17) -0.0082(17) -0.0018(18)
C15 0.038(2) 0.049(2) 0.040(2) -0.0178(18) -0.0053(17) 0.0013(18)
C16 0.050(3) 0.063(3) 0.056(3) -0.013(2) -0.015(2) 0.000(2)
C17 0.056(3) 0.078(3) 0.072(3) -0.020(2) -0.025(3) 0.021(3)
C18 0.082(4) 0.099(4) 0.057(3) -0.053(3) -0.034(3) 0.021(3)
C19 0.093(4) 0.073(3) 0.058(3) -0.035(3) -0.022(3) -0.006(3)
C20 0.066(3) 0.062(3) 0.058(3) -0.023(2) -0.014(2) 0.003(2)
C21 0.047(2) 0.062(3) 0.056(3) -0.024(2) -0.010(2) 0.002(2)
C22 0.043(3) 0.094(4) 0.056(3) -0.027(2) 0.000(2) 0.005(3)
C23 0.062(4) 0.107(5) 0.102(4) -0.013(3) 0.008(3) -0.031(4)
Cl3 0.0764(10) 0.1109(12) 0.1040(11) -0.0235(8) -0.0027(8) 0.0047(9)
Cl4 0.0777(12) 0.232(3) 0.1399(17) -0.0523(14) 0.0141(11) -0.0440(17)
C24 0.073(4) 0.109(5) 0.175(7) -0.021(4) 0.004(4) -0.006(5)
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'
S S 0.1246 0.1234 '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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 S1 C10 . . 91.40(19) ?
C21 O3 C22 . . 118.3(3) ?
C10 N1 C9 . . 116.4(3) ?
C10 N1 C14 . . 119.4(3) ?
C9 N1 C14 . . 123.2(3) ?
C10 N2 C11 . . 115.5(3) ?
C2 C1 C6 . . 123.5(4) ?
C2 C1 H1 . . 118.2 ?
C6 C1 H1 . . 118.2 ?
C1 C2 C3 . . 118.6(5) ?
C1 C2 H2 . . 120.7 ?
C3 C2 H2 . . 120.7 ?
C4 C3 C2 . . 121.1(4) ?
C4 C3 Cl2 . . 118.8(4) ?
C2 C3 Cl2 . . 120.1(4) ?
C3 C4 C5 . . 119.2(4) ?
C3 C4 H4 . . 120.4 ?
C5 C4 H4 . . 120.4 ?
C4 C5 C6 . . 122.7(4) ?
C4 C5 Cl1 . . 117.1(3) ?
C6 C5 Cl1 . . 120.3(3) ?
C1 C6 C5 . . 114.9(4) ?
C1 C6 C7 . . 124.7(4) ?
C5 C6 C7 . . 120.4(4) ?
C8 C7 C6 . . 132.0(4) ?
C8 C7 H7 . . 114.0 ?
C6 C7 H7 . . 114.0 ?
C7 C8 C9 . . 119.9(4) ?
C7 C8 S1 . . 129.8(3) ?
C9 C8 S1 . . 110.3(3) ?
O1 C9 N1 . . 123.5(4) ?
O1 C9 C8 . . 126.5(4) ?
N1 C9 C8 . . 110.0(3) ?
N2 C10 N1 . . 126.7(4) ?
N2 C10 S1 . . 121.5(3) ?
N1 C10 S1 . . 111.8(3) ?
C13 C11 N2 . . 122.7(4) ?
C13 C11 C12 . . 126.5(4) ?
N2 C11 C12 . . 110.7(3) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 C21 . . 123.4(4) ?
C11 C13 C14 . . 120.2(4) ?
C21 C13 C14 . . 116.3(3) ?
N1 C14 C15 . . 110.1(3) ?
N1 C14 C13 . . 108.3(3) ?
C15 C14 C13 . . 113.2(3) ?
N1 C14 H14 . . 108.4 ?
C15 C14 H14 . . 108.4 ?
C13 C14 H14 . . 108.4 ?
C20 C15 C16 . . 118.1(4) ?
C20 C15 C14 . . 121.1(4) ?
C16 C15 C14 . . 120.8(4) ?
C17 C16 C15 . . 121.0(4) ?
C17 C16 H16 . . 119.5 ?
C15 C16 H16 . . 119.5 ?
C18 C17 C16 . . 119.5(5) ?
C18 C17 H17 . . 120.2 ?
C16 C17 H17 . . 120.2 ?
C19 C18 C17 . . 120.6(4) ?
C19 C18 H18 . . 119.7 ?
C17 C18 H18 . . 119.7 ?
C18 C19 C20 . . 120.0(5) ?
C18 C19 H19 . . 120.0 ?
C20 C19 H19 . . 120.0 ?
C15 C20 C19 . . 120.8(5) ?
C15 C20 H20 . . 119.6 ?
C19 C20 H20 . . 119.6 ?
O2 C21 O3 . . 121.6(4) ?
O2 C21 C13 . . 127.1(4) ?
O3 C21 C13 . . 111.2(4) ?
O3 C22 C23 . . 107.4(4) ?
O3 C22 H22A . . 110.2 ?
C23 C22 H22A . . 110.2 ?
O3 C22 H22B . . 110.2 ?
C23 C22 H22B . . 110.2 ?
H22A C22 H22B . . 108.5 ?
C22 C23 H23A . . 109.5 ?
C22 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C22 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
Cl4 C24 Cl3 . . 112.2(4) ?
Cl4 C24 H24A . . 109.2 ?
Cl3 C24 H24A . . 109.2 ?
Cl4 C24 H24B . . 109.2 ?
Cl3 C24 H24B . . 109.2 ?
H24A C24 H24B . . 107.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 . 1.761(4) ?
S1 C10 . 1.769(4) ?
Cl1 C5 . 1.735(5) ?
Cl2 C3 . 1.749(4) ?
O1 C9 . 1.215(4) ?
O2 C21 . 1.204(5) ?
O3 C21 . 1.337(5) ?
O3 C22 . 1.458(5) ?
N1 C10 . 1.372(5) ?
N1 C9 . 1.395(5) ?
N1 C14 . 1.484(4) ?
N2 C10 . 1.296(5) ?
N2 C11 . 1.423(5) ?
C1 C2 . 1.378(6) ?
C1 C6 . 1.408(6) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.387(7) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.375(6) ?
C4 C5 . 1.386(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.415(6) ?
C6 C7 . 1.455(5) ?
C7 C8 . 1.346(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.499(5) ?
C11 C13 . 1.361(5) ?
C11 C12 . 1.507(6) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C21 . 1.476(6) ?
C13 C14 . 1.525(5) ?
C14 C15 . 1.522(5) ?
C14 H14 . 0.9800 ?
C15 C20 . 1.386(6) ?
C15 C16 . 1.394(6) ?
C16 C17 . 1.387(6) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.381(7) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.359(7) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.396(6) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
C22 C23 . 1.484(7) ?
C22 H22A . 0.9700 ?
C22 H22B . 0.9700 ?
C23 H23A . 0.9600 ?
C23 H23B . 0.9600 ?
C23 H23C . 0.9600 ?
Cl3 C24 . 1.764(7) ?
Cl4 C24 . 1.726(7) ?
C24 H24A . 0.9700 ?
C24 H24B . 0.9700 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.3(7) ?
C1 C2 C3 C4 . . . . 0.5(7) ?
C1 C2 C3 Cl2 . . . . 179.7(3) ?
C2 C3 C4 C5 . . . . -0.4(7) ?
Cl2 C3 C4 C5 . . . . -179.6(3) ?
C3 C4 C5 C6 . . . . -0.5(6) ?
C3 C4 C5 Cl1 . . . . 180.0(3) ?
C2 C1 C6 C5 . . . . -1.1(6) ?
C2 C1 C6 C7 . . . . 177.9(4) ?
C4 C5 C6 C1 . . . . 1.2(6) ?
Cl1 C5 C6 C1 . . . . -179.3(3) ?
C4 C5 C6 C7 . . . . -177.9(4) ?
Cl1 C5 C6 C7 . . . . 1.6(5) ?
C1 C6 C7 C8 . . . . -3.8(7) ?
C5 C6 C7 C8 . . . . 175.2(4) ?
C6 C7 C8 C9 . . . . -177.0(4) ?
C6 C7 C8 S1 . . . . 0.9(7) ?
C10 S1 C8 C7 . . . . -177.9(4) ?
C10 S1 C8 C9 . . . . 0.2(3) ?
C10 N1 C9 O1 . . . . -178.3(3) ?
C14 N1 C9 O1 . . . . 13.0(6) ?
C10 N1 C9 C8 . . . . 1.8(4) ?
C14 N1 C9 C8 . . . . -166.8(3) ?
C7 C8 C9 O1 . . . . -2.6(6) ?
S1 C8 C9 O1 . . . . 179.1(3) ?
C7 C8 C9 N1 . . . . 177.2(3) ?
S1 C8 C9 N1 . . . . -1.1(4) ?
C11 N2 C10 N1 . . . . -7.4(6) ?
C11 N2 C10 S1 . . . . 170.2(3) ?
C9 N1 C10 N2 . . . . 176.1(4) ?
C14 N1 C10 N2 . . . . -14.9(6) ?
C9 N1 C10 S1 . . . . -1.7(4) ?
C14 N1 C10 S1 . . . . 167.3(2) ?
C8 S1 C10 N2 . . . . -177.1(3) ?
C8 S1 C10 N1 . . . . 0.9(3) ?
C10 N2 C11 C13 . . . . 12.1(6) ?
C10 N2 C11 C12 . . . . -167.6(4) ?
N2 C11 C13 C21 . . . . -179.3(4) ?
C12 C11 C13 C21 . . . . 0.4(7) ?
N2 C11 C13 C14 . . . . 5.2(6) ?
C12 C11 C13 C14 . . . . -175.1(4) ?
C10 N1 C14 C15 . . . . -95.5(4) ?
C9 N1 C14 C15 . . . . 72.8(4) ?
C10 N1 C14 C13 . . . . 28.8(4) ?
C9 N1 C14 C13 . . . . -162.9(3) ?
C11 C13 C14 N1 . . . . -24.3(5) ?
C21 C13 C14 N1 . . . . 160.0(3) ?
C11 C13 C14 C15 . . . . 98.2(4) ?
C21 C13 C14 C15 . . . . -77.6(4) ?
N1 C14 C15 C20 . . . . -98.9(4) ?
C13 C14 C15 C20 . . . . 139.7(4) ?
N1 C14 C15 C16 . . . . 79.7(4) ?
C13 C14 C15 C16 . . . . -41.7(5) ?
C20 C15 C16 C17 . . . . 1.1(6) ?
C14 C15 C16 C17 . . . . -177.5(4) ?
C15 C16 C17 C18 . . . . -0.6(7) ?
C16 C17 C18 C19 . . . . -0.2(7) ?
C17 C18 C19 C20 . . . . 0.5(7) ?
C16 C15 C20 C19 . . . . -0.8(6) ?
C14 C15 C20 C19 . . . . 177.8(4) ?
C18 C19 C20 C15 . . . . 0.0(7) ?
C22 O3 C21 O2 . . . . -5.1(6) ?
C22 O3 C21 C13 . . . . 176.3(3) ?
C11 C13 C21 O2 . . . . 2.7(7) ?
C14 C13 C21 O2 . . . . 178.3(5) ?
C11 C13 C21 O3 . . . . -178.8(4) ?
C14 C13 C21 O3 . . . . -3.1(5) ?
C21 O3 C22 C23 . . . . -179.7(4) ?