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#$Date: 2022-04-04 11:59:37 +0300 (Mon, 04 Apr 2022) $
#$Revision: 274312 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/50/8105010.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_8105010
loop_
_publ_author_name
'Cui, Chuansheng'
'Zhang, Haichao'
'Gu, Xiaoyu'
_publ_section_title
;
 The crystal structure of
 13-ethoxycarbonyl-9-methyl-4-chlor-11-thioxo-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6-triene,
 C14H15ClN2O3S
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              43
_journal_page_last               44
_journal_paper_doi               10.1515/ncrs-2019-0459
_journal_volume                  235
_journal_year                    2019
_chemical_formula_sum            'C14 H15 Cl N2 O3 S'
_chemical_formula_weight         326.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 93.9770(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.0104(15)
_cell_length_b                   8.6786(7)
_cell_length_c                   20.4283(18)
_cell_measurement_reflns_used    2728
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.184
_cell_measurement_theta_min      2.401
_cell_volume                     3008.5(4)
_computing_cell_refinement       'SMART [1]'
_computing_data_collection       'SMART [1]'
_computing_data_reduction        'SMART [1]'
_computing_molecular_graphics    'XP in SHELXTL [2]'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018) [2]'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018) [2]'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7314
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.014
_diffrn_reflns_theta_max         25.014
_diffrn_reflns_theta_min         2.400
_exptl_absorpt_coefficient_mu    0.403
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0378P)²+2.4917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0937
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1995
_reflns_number_total             2663
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0459_suppl.cif
_cod_data_source_block           cui
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               8105010
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.916
_shelx_estimated_absorpt_t_max   0.927
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.11588(4) -0.35761(8) 0.71458(3) 0.0641(2) Uani 1 1 d . . . . .
N1 N 0.06821(9) 0.0225(2) 0.94534(8) 0.0330(4) Uani 1 1 d . . . . .
H1 H 0.055255 -0.057886 0.966746 0.040 Uiso 1 1 calc R U . . .
N2 N 0.14020(10) 0.2420(2) 0.93765(9) 0.0396(5) Uani 1 1 d . . . . .
H2' H 0.181880 0.292362 0.950801 0.047 Uiso 1 1 calc R U . . .
O1 O 0.13201(9) 0.26888(18) 0.82184(7) 0.0418(4) Uani 1 1 d . . . . .
O2 O -0.03187(10) 0.2768(2) 0.98376(8) 0.0561(5) Uani 1 1 d . . . . .
O3 O -0.10555(9) 0.3461(2) 0.89435(8) 0.0596(5) Uani 1 1 d . . . . .
S1 S 0.17459(4) 0.07202(8) 1.04340(3) 0.0536(2) Uani 1 1 d . . . . .
C1 C 0.12131(13) -0.1732(3) 0.74840(11) 0.0419(6) Uani 1 1 d . . . . .
C2 C 0.07630(12) -0.1373(3) 0.79964(10) 0.0356(5) Uani 1 1 d . . . . .
H2 H 0.044550 -0.212230 0.816848 0.043 Uiso 1 1 calc R U . . .
C3 C 0.07804(11) 0.0105(2) 0.82581(9) 0.0316(5) Uani 1 1 d . . . . .
C4 C 0.12640(12) 0.1198(3) 0.79940(10) 0.0353(5) Uani 1 1 d . . . . .
C5 C 0.17109(13) 0.0824(3) 0.74739(11) 0.0448(6) Uani 1 1 d . . . . .
H5 H 0.202840 0.156832 0.729790 0.054 Uiso 1 1 calc R U . . .
C6 C 0.16866(14) -0.0640(3) 0.72175(11) 0.0489(6) Uani 1 1 d . . . . .
H6 H 0.198567 -0.089196 0.686857 0.059 Uiso 1 1 calc R U . . .
C7 C 0.02769(11) 0.0543(2) 0.88126(10) 0.0315(5) Uani 1 1 d . . . . .
H7 H -0.022422 -0.001663 0.876893 0.038 Uiso 1 1 calc R U . . .
C8 C 0.01257(12) 0.2277(2) 0.87586(10) 0.0342(5) Uani 1 1 d . . . . .
H8 H -0.011639 0.248734 0.831832 0.041 Uiso 1 1 calc R U . . .
C9 C 0.09414(12) 0.3037(2) 0.88131(10) 0.0353(5) Uani 1 1 d . . . . .
C10 C 0.09252(16) 0.4771(3) 0.88448(13) 0.0526(6) Uani 1 1 d . . . . .
H10A H 0.145375 0.516158 0.885158 0.079 Uiso 1 1 calc R U . . .
H10B H 0.068825 0.508941 0.923587 0.079 Uiso 1 1 calc R U . . .
H10C H 0.062337 0.516707 0.846733 0.079 Uiso 1 1 calc R U . . .
C11 C 0.12453(12) 0.1145(3) 0.97135(10) 0.0341(5) Uani 1 1 d . . . . .
C12 C -0.04272(13) 0.2859(3) 0.92506(11) 0.0376(5) Uani 1 1 d . . . . .
C13 C -0.16934(15) 0.3969(4) 0.93384(14) 0.0754(10) Uani 1 1 d . . . . .
H13A H -0.163620 0.350688 0.977138 0.091 Uiso 1 1 calc R U . . .
H13B H -0.168211 0.508104 0.938725 0.091 Uiso 1 1 calc R U . . .
C14 C -0.24317(16) 0.3486(4) 0.89970(16) 0.0806(10) Uani 1 1 d . . . . .
H14A H -0.248500 0.396211 0.857210 0.121 Uiso 1 1 calc R U . . .
H14B H -0.286385 0.379070 0.924633 0.121 Uiso 1 1 calc R U . . .
H14C H -0.243337 0.238584 0.894742 0.121 Uiso 1 1 calc R U . . .
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_
_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
C11 N1 C7 121.72(17) . .
C11 N2 C9 126.70(18) . .
C4 O1 C9 116.91(15) . .
C12 O3 C13 117.87(19) . .
C2 C1 C6 121.0(2) . .
C2 C1 Cl1 119.56(19) . .
C6 C1 Cl1 119.38(18) . .
C1 C2 C3 120.3(2) . .
C2 C3 C4 118.59(19) . .
C2 C3 C7 121.44(18) . .
C4 C3 C7 119.96(19) . .
O1 C4 C5 116.54(19) . .
O1 C4 C3 122.89(18) . .
C5 C4 C3 120.6(2) . .
C6 C5 C4 120.3(2) . .
C5 C6 C1 119.2(2) . .
N1 C7 C3 111.46(16) . .
N1 C7 C8 108.48(16) . .
C3 C7 C8 107.11(17) . .
C12 C8 C7 112.98(17) . .
C12 C8 C9 114.21(18) . .
C7 C8 C9 105.73(16) . .
O1 C9 N2 110.00(17) . .
O1 C9 C10 104.81(17) . .
N2 C9 C10 110.22(19) . .
O1 C9 C8 107.62(17) . .
N2 C9 C8 109.58(16) . .
C10 C9 C8 114.43(19) . .
N1 C11 N2 117.02(18) . .
N1 C11 S1 121.52(16) . .
N2 C11 S1 121.45(17) . .
O2 C12 O3 124.6(2) . .
O2 C12 C8 125.6(2) . .
O3 C12 C8 109.86(18) . .
C14 C13 O3 107.3(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1 1.743(2) .
N1 C11 1.329(3) .
N1 C7 1.463(2) .
N2 C11 1.339(3) .
N2 C9 1.449(3) .
O1 C4 1.374(3) .
O1 C9 1.446(2) .
O2 C12 1.203(2) .
O3 C12 1.310(3) .
O3 C13 1.464(3) .
S1 C11 1.689(2) .
C1 C2 1.375(3) .
C1 C6 1.380(3) .
C2 C3 1.389(3) .
C3 C4 1.389(3) .
C3 C7 1.515(3) .
C4 C5 1.387(3) .
C5 C6 1.374(3) .
C7 C8 1.529(3) .
C8 C12 1.510(3) .
C8 C9 1.533(3) .
C9 C10 1.506(3) .
C13 C14 1.455(4) .
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
C6 C1 C2 C3 -0.3(3) . . . .
Cl1 C1 C2 C3 -177.97(15) . . . .
C1 C2 C3 C4 -0.4(3) . . . .
C1 C2 C3 C7 178.62(19) . . . .
C9 O1 C4 C5 -172.00(18) . . . .
C9 O1 C4 C3 9.0(3) . . . .
C2 C3 C4 O1 179.87(18) . . . .
C7 C3 C4 O1 0.8(3) . . . .
C2 C3 C4 C5 0.9(3) . . . .
C7 C3 C4 C5 -178.15(19) . . . .
O1 C4 C5 C6 -179.7(2) . . . .
C3 C4 C5 C6 -0.7(3) . . . .
C4 C5 C6 C1 0.0(3) . . . .
C2 C1 C6 C5 0.5(3) . . . .
Cl1 C1 C6 C5 178.21(18) . . . .
C11 N1 C7 C3 77.5(2) . . . .
C11 N1 C7 C8 -40.2(2) . . . .
C2 C3 C7 N1 88.2(2) . . . .
C4 C3 C7 N1 -92.8(2) . . . .
C2 C3 C7 C8 -153.27(18) . . . .
C4 C3 C7 C8 25.7(2) . . . .
N1 C7 C8 C12 -64.2(2) . . . .
C3 C7 C8 C12 175.34(17) . . . .
N1 C7 C8 C9 61.37(19) . . . .
C3 C7 C8 C9 -59.1(2) . . . .
C4 O1 C9 N2 75.0(2) . . . .
C4 O1 C9 C10 -166.53(18) . . . .
C4 O1 C9 C8 -44.3(2) . . . .
C11 N2 C9 O1 -103.1(2) . . . .
C11 N2 C9 C10 141.8(2) . . . .
C11 N2 C9 C8 15.0(3) . . . .
C12 C8 C9 O1 -164.89(17) . . . .
C7 C8 C9 O1 70.26(19) . . . .
C12 C8 C9 N2 75.5(2) . . . .
C7 C8 C9 N2 -49.3(2) . . . .
C12 C8 C9 C10 -48.9(3) . . . .
C7 C8 C9 C10 -173.70(18) . . . .
C7 N1 C11 N2 3.0(3) . . . .
C7 N1 C11 S1 -176.58(14) . . . .
C9 N2 C11 N1 10.8(3) . . . .
C9 N2 C11 S1 -169.65(16) . . . .
C13 O3 C12 O2 -4.1(4) . . . .
C13 O3 C12 C8 174.8(2) . . . .
C7 C8 C12 O2 59.8(3) . . . .
C9 C8 C12 O2 -61.1(3) . . . .
C7 C8 C12 O3 -119.2(2) . . . .
C9 C8 C12 O3 119.9(2) . . . .
C12 O3 C13 C14 -137.7(3) . . . .
