data_2203298
loop_
_publ_author_name
'Liu, Xin-Gang'
'Feng, Ya-Qing'
'Li, Xiao-Fang'
'Gao, Bo'
_publ_section_title
;
Ethyl
5-(2,6-dichlorophenyl)-7-methyl-2-(1-naphthylmethylene)-3-oxo-2,3-dihydro-
5H-thiazolo[3,2-a]pyrimidine-6-carboxylate
;
_journal_issue                 3
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o464
_journal_page_last             o465
_journal_volume                60
_journal_year                  2004
_chemical_formula_analytical   ?
_chemical_formula_iupac        'C27 H20 Cl2 N2 O3 S'
_chemical_formula_moiety       'C27 H20 Cl2 N2 O3 S'
_chemical_formula_structural   ?
_chemical_formula_sum          'C27 H20 Cl2 N2 O3 S'
_chemical_formula_weight       523.41
_chemical_melting_point        .241E-239
_chemical_name_common          ?
_chemical_name_systematic
;
Ethyl
5-(2,6-dichlorophenyl)-7-methyl-2-(1-naphthylmethylene)-3-oxo-2,3-dihydro-
5H-thiazolo[3,2-a]pyrimidine-6-carboxylate
;
_symmetry_cell_setting         Triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_cell_angle_alpha              84.194(6)
_cell_angle_beta               87.085(6)
_cell_angle_gamma              62.970(5)
_cell_formula_units_Z          2
_cell_length_a                 8.974(3)
_cell_length_b                 9.126(3)
_cell_length_c                 16.463(6)
_cell_measurement_reflns_used  826
_cell_measurement_temperature  293(2)
_cell_measurement_theta_max    26.33
_cell_measurement_theta_min    2.83
_cell_volume                   1194.8(8)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type 'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method     '\f and \w'
_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 0.0246
_diffrn_reflns_av_sigmaI/netI  0.0491
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_l_max     19
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_number          6116
_diffrn_reflns_reduction_process ?
_diffrn_reflns_theta_full      25.00
_diffrn_reflns_theta_max       25.00
_diffrn_reflns_theta_min       1.24
_diffrn_standards_decay_%      stable
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number       ?
_exptl_absorpt_coefficient_mu  0.393
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_correction_T_min 0.867
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Bruker, 1997)'
_exptl_crystal_colour          colorless
_exptl_crystal_density_diffrn  1.455
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     block
_exptl_crystal_F_000           540
_exptl_crystal_size_max        0.18
_exptl_crystal_size_mid        0.16
_exptl_crystal_size_min        0.16
_exptl_crystal_size_rad        ?
_refine_diff_density_max       0.250
_refine_diff_density_min       -0.227
_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 1.059
_refine_ls_hydrogen_treatment  constr
_refine_ls_matrix_type         full
_refine_ls_number_constraints  ?
_refine_ls_number_parameters   335
_refine_ls_number_reflns       4182
_refine_ls_number_restraints   16
_refine_ls_restrained_S_all    1.067
_refine_ls_restrained_S_obs    ?
_refine_ls_R_factor_all        0.0745
_refine_ls_R_factor_gt         0.0404
_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^)+(0.065P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_all       ?
_refine_ls_wR_factor_ref       0.1261
_reflns_number_gt              2795
_reflns_number_total           4182
_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 0.26886(9) 0.96157(9) 0.41771(5) 0.0477(2) Uani d . 1 . . S
Cl1 0.89795(12) 0.98332(12) 0.20761(6) 0.0766(3) Uani d . 1 . . Cl
Cl2 0.28046(11) 1.03349(12) 0.15243(6) 0.0729(3) Uani d . 1 . . Cl
O1 0.7411(3) 0.5357(3) 0.11188(15) 0.0802(8) Uani d . 1 . . O
O2 0.8756(3) 0.6607(3) 0.15878(14) 0.0701(7) Uani d D 1 . . O
O3 0.5775(3) 1.1281(3) 0.34046(13) 0.0580(6) Uani d . 1 . . O
N1 0.5020(3) 0.9320(3) 0.31175(13) 0.0367(5) Uani d . 1 . . N
N2 0.3907(3) 0.7412(3) 0.30876(15) 0.0474(6) Uani d . 1 . . N
C1 0.7140(4) 1.0564(4) 0.15223(19) 0.0586(9) Uani d . 1 . . C
C2 0.6952(6) 1.1690(5) 0.0866(3) 0.0814(12) Uani d . 1 . . C
H2 0.7785 1.2015 0.0736 0.098 Uiso calc R 1 . . H
C3 0.5541(7) 1.2328(5) 0.0408(3) 0.0944(14) Uani d . 1 . . C
H3 0.5424 1.3068 -0.0045 0.113 Uiso calc R 1 . . H
C4 0.4284(5) 1.1884(4) 0.0611(2) 0.0791(11) Uani d . 1 . . C
H4 0.3312 1.2330 0.0302 0.095 Uiso calc R 1 . . H
C5 0.4484(4) 1.0765(4) 0.12802(19) 0.0568(8) Uani d . 1 . . C
C6 0.5925(4) 1.0034(3) 0.17501(17) 0.0458(7) Uani d . 1 . . C
C7 0.6236(3) 0.8693(3) 0.24490(16) 0.0386(6) Uani d . 1 A . C
H7 0.7356 0.8346 0.2665 0.046 Uiso calc R 1 . . H
C8 0.6178(3) 0.7177(3) 0.21689(16) 0.0413(6) Uani d . 1 . . C
C9 0.7464(4) 0.6275(4) 0.15753(18) 0.0493(7) Uani d . 1 A . C
C10 1.0362(13) 0.5611(13) 0.1179(6) 0.069(3) Uani d PD 0.61(2) A 1 C
H10A 1.0315 0.4718 0.0927 0.082 Uiso calc PR 0.61(2) A 1 H
H10B 1.1274 0.5146 0.1568 0.082 Uiso calc PR 0.61(2) A 1 H
C11 1.0597(18) 0.6788(11) 0.0547(7) 0.082(3) Uani d PDU 0.61(2) A 1 C
H11A 1.1635 0.6218 0.0263 0.123 Uiso calc PR 0.61(2) A 1 H
H11B 1.0616 0.7675 0.0807 0.123 Uiso calc PR 0.61(2) A 1 H
H11C 0.9690 0.7226 0.0166 0.123 Uiso calc PR 0.61(2) A 1 H
C10' 0.988(2) 0.589(3) 0.0897(12) 0.082(6) Uani d PD 0.39(2) A 2 C
H10C 0.9270 0.6262 0.0387 0.099 Uiso calc PR 0.39(2) A 2 H
H10D 1.0398 0.4698 0.0968 0.099 Uiso calc PR 0.39(2) A 2 H
C11' 1.1185(18) 0.651(2) 0.0899(14) 0.091(5) Uani d PDU 0.39(2) A 2 C
H11D 1.2014 0.6006 0.0489 0.136 Uiso calc PR 0.39(2) A 2 H
H11E 1.1707 0.6216 0.1425 0.136 Uiso calc PR 0.39(2) A 2 H
H11F 1.0662 0.7684 0.0785 0.136 Uiso calc PR 0.39(2) A 2 H
C12 0.5073(3) 0.6646(3) 0.24741(17) 0.0437(7) Uani d . 1 A . C
C13 0.4940(4) 0.5159(4) 0.2230(2) 0.0643(9) Uani d . 1 . . C
H13A 0.4055 0.5041 0.2535 0.096 Uiso calc PR 0.50 A . H
H13B 0.5978 0.4187 0.2342 0.096 Uiso calc PR 0.50 . . H
H13C 0.4704 0.5304 0.1657 0.096 Uiso calc PR 0.50 . . H
H13D 0.5769 0.4647 0.1821 0.096 Uiso calc PR 0.50 . . H
H13E 0.3846 0.5501 0.2014 0.096 Uiso calc PR 0.50 . . H
H13F 0.5120 0.4384 0.2699 0.096 Uiso calc PR 0.50 . . H
C14 0.3972(3) 0.8632(3) 0.33713(16) 0.0396(6) Uani d . 1 . . C
C15 0.3570(3) 1.0974(3) 0.41762(16) 0.0377(6) Uani d . 1 . . C
C16 0.4898(3) 1.0595(3) 0.35471(16) 0.0395(6) Uani d . 1 . . C
C17 0.3212(3) 1.2216(3) 0.46485(16) 0.0407(6) Uani d . 1 . . C
H17 0.3859 1.2771 0.4536 0.049 Uiso calc R 1 . . H
C18 0.2005(3) 1.2844(3) 0.52992(16) 0.0388(6) Uani d . 1 . . C
C19 0.0925(4) 1.2189(4) 0.55458(17) 0.0511(8) Uani d . 1 . . C
H19 0.1016 1.1270 0.5307 0.061 Uiso calc R 1 . . H
C20 -0.0297(4) 1.2857(4) 0.61408(18) 0.0575(8) Uani d . 1 . . C
H20 -0.1014 1.2392 0.6289 0.069 Uiso calc R 1 . . H
C21 -0.0444(4) 1.4181(4) 0.65039(18) 0.0553(8) Uani d . 1 . . C
H21 -0.1269 1.4620 0.6899 0.066 Uiso calc R 1 . . H
C22 0.0625(3) 1.4910(3) 0.62960(16) 0.0442(7) Uani d . 1 . . C
C23 0.0468(4) 1.6292(4) 0.66767(18) 0.0546(8) Uani d . 1 . . C
H23 -0.0355 1.6730 0.7072 0.066 Uiso calc R 1 . . H
C24 0.1505(4) 1.6994(4) 0.6472(2) 0.0620(9) Uani d . 1 . . C
H24 0.1394 1.7901 0.6729 0.074 Uiso calc R 1 . . H
C25 0.2736(4) 1.6347(4) 0.5876(2) 0.0568(8) Uani d . 1 . . C
H25 0.3439 1.6831 0.5736 0.068 Uiso calc R 1 . . H
C26 0.2921(4) 1.5019(3) 0.54981(18) 0.0494(7) Uani d . 1 . . C
H26 0.3755 1.4607 0.5105 0.059 Uiso calc R 1 . . H
C27 0.1874(3) 1.4245(3) 0.56869(16) 0.0386(6) Uani d . 1 . . C
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 0.0499(4) 0.0491(4) 0.0584(5) -0.0336(4) 0.0194(3) -0.0203(4)
Cl1 0.0825(6) 0.0978(7) 0.0871(7) -0.0701(6) 0.0355(5) -0.0435(5)
Cl2 0.0597(5) 0.0786(6) 0.0743(6) -0.0276(5) -0.0072(4) 0.0046(5)
O1 0.0894(18) 0.0921(18) 0.0812(17) -0.0535(15) 0.0279(13) -0.0555(15)
O2 0.0658(15) 0.0825(16) 0.0832(17) -0.0473(13) 0.0426(12) -0.0518(14)
O3 0.0678(14) 0.0641(13) 0.0698(14) -0.0515(12) 0.0312(11) -0.0341(11)
N1 0.0388(12) 0.0366(12) 0.0415(13) -0.0221(10) 0.0104(10) -0.0141(10)
N2 0.0500(14) 0.0431(13) 0.0613(16) -0.0304(12) 0.0123(12) -0.0176(12)
C1 0.081(2) 0.0528(19) 0.0581(19) -0.0432(18) 0.0309(17) -0.0253(16)
C2 0.118(4) 0.069(2) 0.078(3) -0.061(3) 0.041(3) -0.019(2)
C3 0.141(4) 0.066(3) 0.070(3) -0.047(3) 0.033(3) 0.005(2)
C4 0.100(3) 0.059(2) 0.060(2) -0.023(2) 0.010(2) 0.0009(19)
C5 0.072(2) 0.0448(17) 0.0505(19) -0.0242(16) 0.0133(17) -0.0071(15)
C6 0.0600(18) 0.0383(15) 0.0455(16) -0.0270(14) 0.0171(14) -0.0159(13)
C7 0.0407(15) 0.0362(14) 0.0450(16) -0.0216(12) 0.0098(12) -0.0138(12)
C8 0.0448(16) 0.0377(15) 0.0456(16) -0.0208(13) 0.0043(13) -0.0137(13)
C9 0.0603(19) 0.0464(17) 0.0465(17) -0.0276(15) 0.0095(14) -0.0147(14)
C10 0.081(6) 0.081(6) 0.061(5) -0.047(5) 0.027(4) -0.041(5)
C11 0.093(6) 0.085(5) 0.074(5) -0.044(5) 0.034(5) -0.032(4)
C10' 0.057(8) 0.125(13) 0.073(11) -0.043(9) 0.044(8) -0.060(11)
C11' 0.061(7) 0.110(8) 0.090(9) -0.031(6) 0.021(6) -0.011(7)
C12 0.0485(17) 0.0375(15) 0.0508(17) -0.0228(13) 0.0027(13) -0.0132(13)
C13 0.077(2) 0.058(2) 0.079(2) -0.0454(18) 0.0154(18) -0.0301(18)
C14 0.0369(15) 0.0391(15) 0.0479(16) -0.0216(13) 0.0037(12) -0.0060(13)
C15 0.0372(14) 0.0410(15) 0.0416(15) -0.0231(12) 0.0067(12) -0.0088(12)
C16 0.0420(15) 0.0382(15) 0.0454(16) -0.0230(13) 0.0066(13) -0.0135(13)
C17 0.0393(15) 0.0446(16) 0.0470(16) -0.0258(13) 0.0051(12) -0.0105(13)
C18 0.0386(15) 0.0456(16) 0.0390(15) -0.0237(13) 0.0045(12) -0.0123(13)
C19 0.0570(19) 0.0625(19) 0.0517(18) -0.0406(17) 0.0106(15) -0.0197(15)
C20 0.0599(19) 0.084(2) 0.0507(18) -0.0509(19) 0.0171(15) -0.0198(17)
C21 0.0456(17) 0.080(2) 0.0435(17) -0.0295(17) 0.0151(14) -0.0215(16)
C22 0.0390(15) 0.0515(17) 0.0418(16) -0.0183(14) 0.0010(13) -0.0140(14)
C23 0.0527(19) 0.0556(19) 0.0487(18) -0.0160(16) 0.0060(15) -0.0207(15)
C24 0.072(2) 0.0516(19) 0.067(2) -0.0275(18) -0.0043(18) -0.0251(17)
C25 0.062(2) 0.0519(18) 0.068(2) -0.0331(16) 0.0059(17) -0.0200(16)
C26 0.0498(17) 0.0513(18) 0.0546(18) -0.0274(15) 0.0100(14) -0.0199(15)
C27 0.0362(15) 0.0417(15) 0.0396(15) -0.0180(13) 0.0003(12) -0.0097(12)
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
C14 S1 C15 . . 91.74(12) ?
C9 O2 C10' . . 109.2(6) ?
C9 O2 C10 . . 122.0(6) ?
C14 N1 C16 . . 115.8(2) ?
C14 N1 C7 . . 121.9(2) ?
C16 N1 C7 . . 122.2(2) ?
C14 N2 C12 . . 116.6(2) ?
C2 C1 C6 . . 122.7(4) ?
C2 C1 Cl1 . . 116.3(3) ?
C6 C1 Cl1 . . 121.0(3) ?
C3 C2 C1 . . 119.6(4) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
C2 C3 C4 . . 120.4(4) ?
C2 C3 H3 . . 119.8 ?
C4 C3 H3 . . 119.8 ?
C3 C4 C5 . . 119.1(4) ?
C3 C4 H4 . . 120.4 ?
C5 C4 H4 . . 120.4 ?
C4 C5 C6 . . 122.7(3) ?
C4 C5 Cl2 . . 116.5(3) ?
C6 C5 Cl2 . . 120.8(2) ?
C5 C6 C1 . . 115.3(3) ?
C5 C6 C7 . . 123.7(3) ?
C1 C6 C7 . . 121.0(3) ?
N1 C7 C8 . . 108.9(2) ?
N1 C7 C6 . . 111.4(2) ?
C8 C7 C6 . . 112.4(2) ?
N1 C7 H7 . . 108.0 ?
C8 C7 H7 . . 108.0 ?
C6 C7 H7 . . 108.0 ?
C12 C8 C9 . . 121.7(2) ?
C12 C8 C7 . . 122.4(2) ?
C9 C8 C7 . . 115.8(2) ?
O1 C9 O2 . . 122.0(3) ?
O1 C9 C8 . . 126.8(3) ?
O2 C9 C8 . . 111.3(2) ?
O2 C10 C11 . . 105.3(7) ?
O2 C10 H10A . . 110.7 ?
C11 C10 H10A . . 110.7 ?
O2 C10 H10B . . 110.7 ?
C11 C10 H10B . . 110.7 ?
H10A C10 H10B . . 108.8 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O2 C10' C11' . . 105.5(10) ?
O2 C10' H10C . . 110.6 ?
C11' C10' H10C . . 110.6 ?
O2 C10' H10D . . 110.6 ?
C11' C10' H10D . . 110.6 ?
H10C C10' H10D . . 108.8 ?
C10' C11' H11D . . 109.5 ?
C10' C11' H11E . . 109.5 ?
H11D C11' H11E . . 109.5 ?
C10' C11' H11F . . 109.5 ?
H11D C11' H11F . . 109.5 ?
H11E C11' H11F . . 109.5 ?
C8 C12 N2 . . 123.0(2) ?
C8 C12 C13 . . 125.5(3) ?
N2 C12 C13 . . 111.4(2) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C12 C13 H13D . . 109.5 ?
H13A C13 H13D . . 141.1 ?
H13B C13 H13D . . 56.3 ?
H13C C13 H13D . . 56.3 ?
C12 C13 H13E . . 109.5 ?
H13A C13 H13E . . 56.3 ?
H13B C13 H13E . . 141.1 ?
H13C C13 H13E . . 56.3 ?
H13D C13 H13E . . 109.5 ?
C12 C13 H13F . . 109.5 ?
H13A C13 H13F . . 56.3 ?
H13B C13 H13F . . 56.3 ?
H13C C13 H13F . . 141.1 ?
H13D C13 H13F . . 109.5 ?
H13E C13 H13F . . 109.5 ?
N2 C14 N1 . . 126.9(3) ?
N2 C14 S1 . . 121.4(2) ?
N1 C14 S1 . . 111.64(18) ?
C17 C15 C16 . . 120.1(2) ?
C17 C15 S1 . . 129.8(2) ?
C16 C15 S1 . . 110.15(18) ?
O3 C16 N1 . . 122.9(2) ?
O3 C16 C15 . . 126.5(2) ?
N1 C16 C15 . . 110.6(2) ?
C15 C17 C18 . . 131.7(3) ?
C15 C17 H17 . . 114.1 ?
C18 C17 H17 . . 114.1 ?
C19 C18 C27 . . 118.4(2) ?
C19 C18 C17 . . 122.4(2) ?
C27 C18 C17 . . 119.2(2) ?
C18 C19 C20 . . 122.1(3) ?
C18 C19 H19 . . 118.9 ?
C20 C19 H19 . . 118.9 ?
C21 C20 C19 . . 120.2(3) ?
C21 C20 H20 . . 119.9 ?
C19 C20 H20 . . 119.9 ?
C20 C21 C22 . . 121.3(3) ?
C20 C21 H21 . . 119.3 ?
C22 C21 H21 . . 119.3 ?
C21 C22 C23 . . 121.2(3) ?
C21 C22 C27 . . 119.2(2) ?
C23 C22 C27 . . 119.7(3) ?
C24 C23 C22 . . 120.9(3) ?
C24 C23 H23 . . 119.5 ?
C22 C23 H23 . . 119.5 ?
C23 C24 C25 . . 119.7(3) ?
C23 C24 H24 . . 120.1 ?
C25 C24 H24 . . 120.1 ?
C26 C25 C24 . . 120.9(3) ?
C26 C25 H25 . . 119.6 ?
C24 C25 H25 . . 119.6 ?
C25 C26 C27 . . 121.7(3) ?
C25 C26 H26 . . 119.2 ?
C27 C26 H26 . . 119.2 ?
C26 C27 C22 . . 117.1(2) ?
C26 C27 C18 . . 124.0(2) ?
C22 C27 C18 . . 118.9(2) ?
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 C14 . 1.743(3) ?
S1 C15 . 1.747(3) ?
Cl1 C1 . 1.741(4) ?
Cl2 C5 . 1.742(4) ?
O1 C9 . 1.198(3) ?
O2 C9 . 1.327(3) ?
O2 C10' . 1.474(9) ?
O2 C10 . 1.480(7) ?
O3 C16 . 1.211(3) ?
N1 C14 . 1.377(3) ?
N1 C16 . 1.381(3) ?
N1 C7 . 1.472(3) ?
N2 C14 . 1.276(3) ?
N2 C12 . 1.405(3) ?
C1 C2 . 1.374(5) ?
C1 C6 . 1.402(4) ?
C2 C3 . 1.360(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.378(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.384(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.388(4) ?
C6 C7 . 1.529(4) ?
C7 C8 . 1.526(3) ?
C7 H7 . 0.9800 ?
C8 C12 . 1.344(4) ?
C8 C9 . 1.466(4) ?
C10 C11 . 1.496(8) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C10' C11' . 1.507(10) ?
C10' H10C . 0.9700 ?
C10' H10D . 0.9700 ?
C11' H11D . 0.9600 ?
C11' H11E . 0.9600 ?
C11' H11F . 0.9600 ?
C12 C13 . 1.510(4) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C13 H13D . 0.9600 ?
C13 H13E . 0.9600 ?
C13 H13F . 0.9600 ?
C15 C17 . 1.347(4) ?
C15 C16 . 1.478(4) ?
C17 C18 . 1.446(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.378(4) ?
C18 C27 . 1.441(3) ?
C19 C20 . 1.392(4) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.352(4) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.407(4) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.412(4) ?
C22 C27 . 1.421(4) ?
C23 C24 . 1.363(4) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.395(4) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.358(4) ?
C25 H25 . 0.9300 ?
C26 C27 . 1.416(4) ?
C26 H26 . 0.9300 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?
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(5) ?
Cl1 C1 C2 C3 . . . . -179.4(3) ?
C1 C2 C3 C4 . . . . 1.7(6) ?
C2 C3 C4 C5 . . . . -0.8(6) ?
C3 C4 C5 C6 . . . . -1.6(5) ?
C3 C4 C5 Cl2 . . . . 177.3(3) ?
C4 C5 C6 C1 . . . . 2.8(4) ?
Cl2 C5 C6 C1 . . . . -176.0(2) ?
C4 C5 C6 C7 . . . . -174.9(3) ?
Cl2 C5 C6 C7 . . . . 6.4(4) ?
C2 C1 C6 C5 . . . . -1.9(4) ?
Cl1 C1 C6 C5 . . . . 177.2(2) ?
C2 C1 C6 C7 . . . . 175.8(3) ?
Cl1 C1 C6 C7 . . . . -5.0(4) ?
C14 N1 C7 C8 . . . . -3.8(3) ?
C16 N1 C7 C8 . . . . 173.9(2) ?
C14 N1 C7 C6 . . . . 120.7(3) ?
C16 N1 C7 C6 . . . . -61.6(3) ?
C5 C6 C7 N1 . . . . -64.2(3) ?
C1 C6 C7 N1 . . . . 118.3(3) ?
C5 C6 C7 C8 . . . . 58.3(3) ?
C1 C6 C7 C8 . . . . -119.2(3) ?
N1 C7 C8 C12 . . . . 4.3(4) ?
C6 C7 C8 C12 . . . . -119.7(3) ?
N1 C7 C8 C9 . . . . -172.6(2) ?
C6 C7 C8 C9 . . . . 63.5(3) ?
C10' O2 C9 O1 . . . . 8.4(14) ?
C10 O2 C9 O1 . . . . -13.7(7) ?
C10' O2 C9 C8 . . . . -170.9(13) ?
C10 O2 C9 C8 . . . . 167.0(5) ?
C12 C8 C9 O1 . . . . 24.4(5) ?
C7 C8 C9 O1 . . . . -158.8(3) ?
C12 C8 C9 O2 . . . . -156.3(3) ?
C7 C8 C9 O2 . . . . 20.5(4) ?
C9 O2 C10 C11 . . . . 118.5(11) ?
C10' O2 C10 C11 . . . . 56(3) ?
C9 O2 C10' C11' . . . . 173.3(18) ?
C10 O2 C10' C11' . . . . -60(2) ?
C9 C8 C12 N2 . . . . 175.1(3) ?
C7 C8 C12 N2 . . . . -1.5(4) ?
C9 C8 C12 C13 . . . . -3.3(5) ?
C7 C8 C12 C13 . . . . -179.9(3) ?
C14 N2 C12 C8 . . . . -2.3(4) ?
C14 N2 C12 C13 . . . . 176.3(3) ?
C12 N2 C14 N1 . . . . 2.8(4) ?
C12 N2 C14 S1 . . . . -176.0(2) ?
C16 N1 C14 N2 . . . . -177.3(3) ?
C7 N1 C14 N2 . . . . 0.5(4) ?
C16 N1 C14 S1 . . . . 1.6(3) ?
C7 N1 C14 S1 . . . . 179.41(19) ?
C15 S1 C14 N2 . . . . 178.9(2) ?
C15 S1 C14 N1 . . . . -0.1(2) ?
C14 S1 C15 C17 . . . . 179.1(3) ?
C14 S1 C15 C16 . . . . -1.3(2) ?
C14 N1 C16 O3 . . . . 177.9(3) ?
C7 N1 C16 O3 . . . . 0.1(4) ?
C14 N1 C16 C15 . . . . -2.5(3) ?
C7 N1 C16 C15 . . . . 179.6(2) ?
C17 C15 C16 O3 . . . . 1.5(4) ?
S1 C15 C16 O3 . . . . -178.1(2) ?
C17 C15 C16 N1 . . . . -178.0(2) ?
S1 C15 C16 N1 . . . . 2.4(3) ?
C16 C15 C17 C18 . . . . -179.8(3) ?
S1 C15 C17 C18 . . . . -0.3(5) ?
C15 C17 C18 C19 . . . . -0.7(5) ?
C15 C17 C18 C27 . . . . -178.3(3) ?
C27 C18 C19 C20 . . . . 1.4(4) ?
C17 C18 C19 C20 . . . . -176.3(3) ?
C18 C19 C20 C21 . . . . -0.7(5) ?
C19 C20 C21 C22 . . . . -0.3(5) ?
C20 C21 C22 C23 . . . . -180.0(3) ?
C20 C21 C22 C27 . . . . 0.5(5) ?
C21 C22 C23 C24 . . . . -179.9(3) ?
C27 C22 C23 C24 . . . . -0.4(4) ?
C22 C23 C24 C25 . . . . 0.3(5) ?
C23 C24 C25 C26 . . . . -0.3(5) ?
C24 C25 C26 C27 . . . . 0.4(5) ?
C25 C26 C27 C22 . . . . -0.5(4) ?
C25 C26 C27 C18 . . . . 179.4(3) ?
C21 C22 C27 C26 . . . . 180.0(3) ?
C23 C22 C27 C26 . . . . 0.5(4) ?
C21 C22 C27 C18 . . . . 0.1(4) ?
C23 C22 C27 C18 . . . . -179.4(2) ?
C19 C18 C27 C26 . . . . 179.1(3) ?
C17 C18 C27 C26 . . . . -3.1(4) ?
C19 C18 C27 C22 . . . . -1.0(4) ?
C17 C18 C27 C22 . . . . 176.7(2) ?