#------------------------------------------------------------------------------
#$Date: 2023-12-04 10:54:44 +0200 (Mon, 04 Dec 2023) $
#$Revision: 287964 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/77/8107702.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_8107702
loop_
_publ_author_name
'Wang, Qian'
'Liu, Yong-Lang'
'Ye, Jiang-Hai'
'Zou, Juan'
'Wu, Chong'
'Yang, Wu-De'
_publ_section_title
;
 Crystal structure of O-(3-(benzo[d]thiazol-2-yl)naphthalen-2-yl) O-phenyl
 carbonothioate, C24H15NO2S2
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1201
_journal_page_last               1203
_journal_paper_doi               10.1515/ncrs-2023-0403
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C24 H15 N O2 S2'
_chemical_formula_sum            'C24 H15 N O2 S2'
_chemical_formula_weight         413.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 106.278(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.8250(11)
_cell_length_b                   5.3649(3)
_cell_length_c                   18.8787(11)
_cell_measurement_reflns_used    5627
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.56
_cell_measurement_theta_min      3.25
_cell_volume                     2024.7(2)
_computing_cell_refinement       'SAINT (Brucker, 2012)[2]'
_computing_data_collection       'APEX2 (Brucker, 2012)[2]'
_computing_data_reduction        'SAINT (Brucker, 2012)[2]'
_computing_molecular_graphics    'Diamond 4.0[4]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)[1]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)[3]'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15411
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         3.248
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_correction_T_min  0.9782
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0439
_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)+(0.0325P)²+1.0580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1015
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3094
_reflns_number_total             3962
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0403_suppl_001.cif
_cod_data_source_block           a
_cod_database_code               8107702
_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_max   0.956
_shelx_estimated_absorpt_t_min   0.946
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S1 S 0.72952(3) 0.39603(12) 0.55527(3) 0.05553(17) Uani 1 1 d . . . . .
S2 S 0.66977(3) 0.53092(14) 0.74311(3) 0.0655(2) Uani 1 1 d . . . . .
O1 O 0.60388(7) 0.7204(3) 0.61382(9) 0.0659(5) Uani 1 1 d . . . . .
O2 O 0.70763(7) 0.7949(3) 0.64322(8) 0.0523(4) Uani 1 1 d . . . . .
N1 N 0.85437(8) 0.2923(3) 0.61284(9) 0.0475(4) Uani 1 1 d . . . . .
C1 C 0.42010(19) 0.4931(13) 0.6311(3) 0.140(2) Uani 1 1 d . . . . .
H1 H 0.3775 0.4471 0.6330 0.168 Uiso 1 1 calc R . . . .
C2 C 0.44948(18) 0.6971(10) 0.6679(2) 0.1252(16) Uani 1 1 d . . . . .
H2 H 0.4277 0.7875 0.6963 0.150 Uiso 1 1 calc R . . . .
C3 C 0.51185(13) 0.7732(7) 0.66372(18) 0.0891(9) Uani 1 1 d . . . . .
H3 H 0.5317 0.9168 0.6877 0.107 Uiso 1 1 calc R . . . .
C4 C 0.54291(11) 0.6335(5) 0.62405(13) 0.0613(6) Uani 1 1 d . . . . .
C5 C 0.66030(10) 0.6834(4) 0.66718(12) 0.0488(5) Uani 1 1 d . . . . .
C6 C 0.77354(10) 0.8014(4) 0.69139(11) 0.0453(5) Uani 1 1 d . . . . .
C7 C 0.82069(9) 0.6284(4) 0.67908(11) 0.0427(5) Uani 1 1 d . . . . .
C8 C 0.80731(9) 0.4400(4) 0.62040(11) 0.0430(5) Uani 1 1 d . . . . .
C9 C 0.83140(10) 0.1343(4) 0.55365(11) 0.0457(5) Uani 1 1 d . . . . .
C10 C 0.86972(12) -0.0444(4) 0.53115(13) 0.0589(6) Uani 1 1 d . . . . .
H10 H 0.9145 -0.0658 0.5568 0.071 Uiso 1 1 calc R . . . .
C11 C 0.84110(13) -0.1888(5) 0.47096(14) 0.0652(6) Uani 1 1 d . . . . .
H11 H 0.8665 -0.3092 0.4558 0.078 Uiso 1 1 calc R . . . .
C12 C 0.77430(14) -0.1570(5) 0.43216(14) 0.0683(7) Uani 1 1 d . . . . .
H12 H 0.7558 -0.2563 0.3911 0.082 Uiso 1 1 calc R . . . .
C13 C 0.76405(10) 0.1621(4) 0.51484(11) 0.0493(5) Uani 1 1 d . . . . .
C14 C 0.73529(13) 0.0162(5) 0.45283(13) 0.0656(7) Uani 1 1 d . . . . .
H14 H 0.6907 0.0367 0.4264 0.079 Uiso 1 1 calc R . . . .
C15 C 0.4519(2) 0.3553(9) 0.5917(3) 0.1287(16) Uani 1 1 d . . . . .
H15 H 0.4314 0.2143 0.5667 0.154 Uiso 1 1 calc R . . . .
C16 C 0.51537(17) 0.4229(7) 0.58808(18) 0.0928(9) Uani 1 1 d . . . . .
H16 H 0.5382 0.3272 0.5620 0.111 Uiso 1 1 calc R . . . .
C17 C 0.78918(11) 0.9792(4) 0.74349(13) 0.0517(5) Uani 1 1 d . . . . .
H17 H 0.7565 1.0911 0.7482 0.062 Uiso 1 1 calc R . . . .
C18 C 0.85467(11) 0.9983(4) 0.79121(12) 0.0491(5) Uani 1 1 d . . . . .
C19 C 0.87377(13) 1.1793(4) 0.84736(14) 0.0619(6) Uani 1 1 d . . . . .
H19 H 0.8427 1.2958 0.8534 0.074 Uiso 1 1 calc R . . . .
C20 C 0.93741(14) 1.1848(5) 0.89274(15) 0.0693(7) Uani 1 1 d . . . . .
H20 H 0.9494 1.3048 0.9296 0.083 Uiso 1 1 calc R . . . .
C21 C 0.98494(12) 1.0116(5) 0.88432(15) 0.0670(7) Uani 1 1 d . . . . .
H21 H 1.0281 1.0165 0.9160 0.080 Uiso 1 1 calc R . . . .
C22 C 0.96860(11) 0.8369(4) 0.83053(13) 0.0576(6) Uani 1 1 d . . . . .
H22 H 1.0008 0.7240 0.8253 0.069 Uiso 1 1 calc R . . . .
C23 C 0.90292(10) 0.8240(4) 0.78208(12) 0.0467(5) Uani 1 1 d . . . . .
C24 C 0.88446(10) 0.6464(4) 0.72581(11) 0.0468(5) Uani 1 1 d . . . . .
H24 H 0.9168 0.5352 0.7197 0.056 Uiso 1 1 calc R . . . .
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'
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
C13 S1 C8 89.46(10) . .
C5 O1 C4 118.88(17) . .
C5 O2 C6 117.84(15) . .
C8 N1 C9 111.32(17) . .
C2 C1 H1 119.8 . .
C2 C1 C15 120.5(4) . .
C15 C1 H1 119.8 . .
C1 C2 H2 119.7 . .
C1 C2 C3 120.5(4) . .
C3 C2 H2 119.7 . .
C2 C3 H3 120.9 . .
C4 C3 C2 118.2(4) . .
C4 C3 H3 120.9 . .
C3 C4 O1 118.8(3) . .
C3 C4 C16 122.6(3) . .
C16 C4 O1 118.3(3) . .
O1 C5 S2 127.60(16) . .
O1 C5 O2 104.81(17) . .
O2 C5 S2 127.57(15) . .
C7 C6 O2 118.00(19) . .
C17 C6 O2 118.63(18) . .
C17 C6 C7 123.26(19) . .
C6 C7 C8 125.54(18) . .
C24 C7 C6 115.96(19) . .
C24 C7 C8 118.49(17) . .
N1 C8 S1 114.71(16) . .
N1 C8 C7 120.91(18) . .
C7 C8 S1 124.38(14) . .
N1 C9 C10 125.09(19) . .
N1 C9 C13 115.44(18) . .
C10 C9 C13 119.5(2) . .
C9 C10 H10 120.3 . .
C11 C10 C9 119.5(2) . .
C11 C10 H10 120.3 . .
C10 C11 H11 119.7 . .
C10 C11 C12 120.5(2) . .
C12 C11 H11 119.7 . .
C11 C12 H12 119.3 . .
C14 C12 C11 121.5(2) . .
C14 C12 H12 119.3 . .
C9 C13 S1 109.08(16) . .
C14 C13 S1 130.10(18) . .
C14 C13 C9 120.8(2) . .
C12 C14 C13 118.2(2) . .
C12 C14 H14 120.9 . .
C13 C14 H14 120.9 . .
C1 C15 H15 119.8 . .
C1 C15 C16 120.3(4) . .
C16 C15 H15 119.8 . .
C4 C16 C15 117.8(4) . .
C4 C16 H16 121.1 . .
C15 C16 H16 121.1 . .
C6 C17 H17 119.6 . .
C6 C17 C18 120.75(19) . .
C18 C17 H17 119.6 . .
C17 C18 C23 117.7(2) . .
C19 C18 C17 123.2(2) . .
C19 C18 C23 119.0(2) . .
C18 C19 H19 119.7 . .
C20 C19 C18 120.5(2) . .
C20 C19 H19 119.7 . .
C19 C20 H20 119.7 . .
C19 C20 C21 120.6(2) . .
C21 C20 H20 119.7 . .
C20 C21 H21 119.7 . .
C22 C21 C20 120.5(2) . .
C22 C21 H21 119.7 . .
C21 C22 H22 119.6 . .
C21 C22 C23 120.8(2) . .
C23 C22 H22 119.6 . .
C18 C23 C22 118.5(2) . .
C24 C23 C18 119.24(19) . .
C24 C23 C22 122.23(19) . .
C7 C24 C23 123.02(19) . .
C7 C24 H24 118.5 . .
C23 C24 H24 118.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C8 1.754(2) .
S1 C13 1.727(2) .
S2 C5 1.614(2) .
O1 C4 1.416(3) .
O1 C5 1.331(2) .
O2 C5 1.336(2) .
O2 C6 1.419(2) .
N1 C8 1.299(2) .
N1 C9 1.377(3) .
C1 H1 0.9300 .
C1 C2 1.348(7) .
C1 C15 1.349(7) .
C2 H2 0.9300 .
C2 C3 1.385(5) .
C3 H3 0.9300 .
C3 C4 1.346(4) .
C4 C16 1.360(4) .
C6 C7 1.417(3) .
C6 C17 1.343(3) .
C7 C8 1.467(3) .
C7 C24 1.376(3) .
C9 C10 1.388(3) .
C9 C13 1.396(3) .
C10 H10 0.9300 .
C10 C11 1.366(3) .
C11 H11 0.9300 .
C11 C12 1.389(3) .
C12 H12 0.9300 .
C12 C14 1.362(4) .
C13 C14 1.396(3) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C15 C16 1.389(5) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C17 C18 1.412(3) .
C18 C19 1.410(3) .
C18 C23 1.418(3) .
C19 H19 0.9300 .
C19 C20 1.362(3) .
C20 H20 0.9300 .
C20 C21 1.399(4) .
C21 H21 0.9300 .
C21 C22 1.353(3) .
C22 H22 0.9300 .
C22 C23 1.418(3) .
C23 C24 1.398(3) .
C24 H24 0.9300 .
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
C17 H17 S2 0.93 2.96 3.864(2) 165.6 1_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
S1 C13 C14 C12 179.64(19) . . . .
O1 C4 C16 C15 -172.7(3) . . . .
O2 C6 C7 C8 -0.2(3) . . . .
O2 C6 C7 C24 178.17(17) . . . .
O2 C6 C17 C18 -177.96(17) . . . .
N1 C9 C10 C11 -179.5(2) . . . .
N1 C9 C13 S1 0.0(2) . . . .
N1 C9 C13 C14 178.66(19) . . . .
C1 C2 C3 C4 -2.1(6) . . . .
C1 C15 C16 C4 -1.4(6) . . . .
C2 C1 C15 C16 -0.4(7) . . . .
C2 C3 C4 O1 174.5(3) . . . .
C2 C3 C4 C16 0.2(4) . . . .
C3 C4 C16 C15 1.5(5) . . . .
C4 O1 C5 S2 4.5(3) . . . .
C4 O1 C5 O2 -177.0(2) . . . .
C5 O1 C4 C3 81.7(3) . . . .
C5 O1 C4 C16 -103.8(3) . . . .
C5 O2 C6 C7 101.4(2) . . . .
C5 O2 C6 C17 -82.4(2) . . . .
C6 O2 C5 S2 -5.7(3) . . . .
C6 O2 C5 O1 175.77(17) . . . .
C6 C7 C8 S1 -0.4(3) . . . .
C6 C7 C8 N1 178.76(18) . . . .
C6 C7 C24 C23 -0.4(3) . . . .
C6 C17 C18 C19 -179.3(2) . . . .
C6 C17 C18 C23 0.0(3) . . . .
C7 C6 C17 C18 -1.9(3) . . . .
C8 S1 C13 C9 0.25(16) . . . .
C8 S1 C13 C14 -178.3(2) . . . .
C8 N1 C9 C10 179.8(2) . . . .
C8 N1 C9 C13 -0.3(3) . . . .
C8 C7 C24 C23 178.09(18) . . . .
C9 N1 C8 S1 0.5(2) . . . .
C9 N1 C8 C7 -178.72(17) . . . .
C9 C10 C11 C12 0.3(4) . . . .
C9 C13 C14 C12 1.3(3) . . . .
C10 C9 C13 S1 179.89(17) . . . .
C10 C9 C13 C14 -1.4(3) . . . .
C10 C11 C12 C14 -0.4(4) . . . .
C11 C12 C14 C13 -0.3(4) . . . .
C13 S1 C8 N1 -0.46(16) . . . .
C13 S1 C8 C7 178.76(17) . . . .
C13 C9 C10 C11 0.6(3) . . . .
C15 C1 C2 C3 2.2(7) . . . .
C17 C6 C7 C8 -176.31(19) . . . .
C17 C6 C7 C24 2.1(3) . . . .
C17 C18 C19 C20 178.5(2) . . . .
C17 C18 C23 C22 -178.68(19) . . . .
C17 C18 C23 C24 1.5(3) . . . .
C18 C19 C20 C21 0.2(4) . . . .
C18 C23 C24 C7 -1.3(3) . . . .
C19 C18 C23 C22 0.7(3) . . . .
C19 C18 C23 C24 -179.11(19) . . . .
C19 C20 C21 C22 0.6(4) . . . .
C20 C21 C22 C23 -0.6(4) . . . .
C21 C22 C23 C18 0.0(3) . . . .
C21 C22 C23 C24 179.8(2) . . . .
C22 C23 C24 C7 178.9(2) . . . .
C23 C18 C19 C20 -0.8(3) . . . .
C24 C7 C8 S1 -178.80(15) . . . .
C24 C7 C8 N1 0.4(3) . . . .
