#------------------------------------------------------------------------------
#$Date: 2024-07-05 20:23:39 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293163 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/87/7248765.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_7248765
loop_
_publ_author_name
'Wen, Changting'
'Sun, Guojin'
'Liu, Lang'
'Zhang, Jun'
'She, Mengyao'
'Yang, Zheng'
'Liu, Ping'
'Zhang, Shengyong'
'Li, Jianli'
_publ_section_title
;
 Light-assisted green and efficient construction of
 thiadiazole/selenadiazole derivatives
;
_journal_issue                   13
_journal_name_full               'Green Chemistry'
_journal_page_first              7944
_journal_page_last               7950
_journal_paper_doi               10.1039/D4GC02211D
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C17 H10 Br N3 S, 0.3[CHCl3]'
_chemical_formula_sum            'C17.3 H10.3 Br Cl0.9 N3 S'
_chemical_formula_weight         404.06
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-21
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-06-07 deposited with the CCDC.	2024-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.657(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.47(2)
_cell_length_b                   3.862(3)
_cell_length_c                   32.65(3)
_cell_measurement_reflns_used    8859
_cell_measurement_temperature    220.00
_cell_measurement_theta_max      54.623
_cell_measurement_theta_min      2.529
_cell_volume                     3219(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      220.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            24073
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.965
_diffrn_reflns_theta_min         2.533
_diffrn_source_current           2.23
_diffrn_source_power             0.1557878
_diffrn_source_voltage           69.86
_exptl_absorpt_coefficient_mu    4.026
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1693 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.6974.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_description       block
_exptl_crystal_F_000             1611
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0417P)²+3.6824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0825
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2501
_reflns_number_total             3068
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4gc02211d2.cif
_cod_data_source_block           m3
_cod_depositor_comments
'Adding full bibliography for 7248764--7248765.cif.'
_cod_original_cell_volume        3220(4)
_cod_original_formula_sum        'C17.30 H10.30 Br Cl0.90 N3 S'
_cod_database_code               7248765
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 144 electrons were 
found in a volume of 460Å³ in 1 void per unit cell. 
This is consistent with the presence of 
0.3[CHCl3] per Asymmetric Unit 
which account for 139 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
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
Br1 Br 0.65244(2) 0.02193(7) 0.76009(2) 0.04645(12) Uani 1 1 d . . . . .
S1 S 0.66139(2) 0.89586(18) 0.50872(2) 0.03554(16) Uani 1 1 d . . . . .
N1 N 0.64614(8) 0.6317(5) 0.58814(6) 0.0320(4) Uani 1 1 d . . . . .
N2 N 0.57489(9) 1.0383(6) 0.44687(7) 0.0457(6) Uani 1 1 d . . . . .
N3 N 0.56175(8) 0.9126(7) 0.48088(7) 0.0462(6) Uani 1 1 d . . . . .
C1 C 0.60024(9) 0.6870(6) 0.55614(7) 0.0323(5) Uani 1 1 d . . . . .
C2 C 0.63988(12) 1.4305(7) 0.35658(9) 0.0470(7) Uani 1 1 d . . . . .
H2 H 0.618521 1.532991 0.329879 0.056 Uiso 1 1 calc R U . . .
C3 C 0.61803(11) 1.3184(7) 0.38606(8) 0.0428(6) Uani 1 1 d . . . . .
H3 H 0.581891 1.345009 0.379380 0.051 Uiso 1 1 calc R U . . .
C4 C 0.64529(10) 0.4936(6) 0.62629(7) 0.0311(5) Uani 1 1 d . . . . .
C5 C 0.62505(10) 1.0432(6) 0.45637(7) 0.0330(6) Uani 1 1 d . . . . .
C6 C 0.59838(10) 0.4027(7) 0.63189(8) 0.0338(5) Uani 1 1 d . . . . .
C7 C 0.72439(11) 1.2425(8) 0.40529(8) 0.0455(7) Uani 1 1 d . . . . .
H7 H 0.760487 1.215937 0.411784 0.055 Uiso 1 1 calc R U . . .
C8 C 0.60270(9) 0.8296(7) 0.51528(7) 0.0330(5) Uani 1 1 d . . . . .
C9 C 0.70257(10) 1.1314(7) 0.43491(8) 0.0405(6) Uani 1 1 d . . . . .
H9 H 0.724087 1.030850 0.461700 0.049 Uiso 1 1 calc R U . . .
C10 C 0.64864(10) 0.2103(6) 0.70526(7) 0.0355(6) Uani 1 1 d . . . . .
C11 C 0.55153(10) 0.6144(7) 0.55900(8) 0.0405(6) Uani 1 1 d . . . . .
H11 H 0.520190 0.665527 0.535423 0.049 Uiso 1 1 calc R U . . .
C12 C 0.69374(10) 0.4403(6) 0.66147(8) 0.0354(6) Uani 1 1 d . . . . .
H12 H 0.725153 0.502125 0.658114 0.043 Uiso 1 1 calc R U . . .
C13 C 0.55069(10) 0.4687(7) 0.59659(8) 0.0414(6) Uani 1 1 d . . . . .
H13 H 0.518622 0.412206 0.599093 0.050 Uiso 1 1 calc R U . . .
C14 C 0.69511(10) 0.3002(7) 0.70010(7) 0.0380(6) Uani 1 1 d . . . . .
H14 H 0.727399 0.264160 0.723287 0.046 Uiso 1 1 calc R U . . .
C15 C 0.69284(12) 1.3933(7) 0.36598(9) 0.0452(7) Uani 1 1 d . . . . .
H15 H 0.707486 1.470180 0.345729 0.054 Uiso 1 1 calc R U . . .
C16 C 0.64921(10) 1.1663(6) 0.42561(7) 0.0338(5) Uani 1 1 d . . . . .
C17 C 0.60097(10) 0.2571(7) 0.67240(8) 0.0381(6) Uani 1 1 d . . . . .
H17 H 0.570148 0.193136 0.676640 0.046 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
Br Br -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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
C8 S1 C5 86.92(12) . . ?
C1 N1 C4 116.8(2) . . ?
C5 N2 N3 112.6(2) . . ?
C8 N3 N2 112.5(2) . . ?
N1 C1 C8 115.3(2) . . ?
N1 C1 C11 124.7(2) . . ?
C11 C1 C8 120.0(2) . . ?
C3 C2 H2 119.8 . . ?
C3 C2 C15 120.5(3) . . ?
C15 C2 H2 119.8 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C16 120.2(3) . . ?
C16 C3 H3 119.9 . . ?
N1 C4 C6 122.7(2) . . ?
N1 C4 C12 118.1(2) . . ?
C6 C4 C12 119.2(2) . . ?
N2 C5 S1 114.02(18) . . ?
N2 C5 C16 123.3(2) . . ?
C16 C5 S1 122.7(2) . . ?
C4 C6 C13 117.7(2) . . ?
C4 C6 C17 119.1(2) . . ?
C13 C6 C17 123.1(2) . . ?
C9 C7 H7 120.2 . . ?
C9 C7 C15 119.7(3) . . ?
C15 C7 H7 120.2 . . ?
N3 C8 S1 113.98(19) . . ?
N3 C8 C1 124.2(2) . . ?
C1 C8 S1 121.87(17) . . ?
C7 C9 H9 119.6 . . ?
C7 C9 C16 120.8(2) . . ?
C16 C9 H9 119.6 . . ?
C14 C10 Br1 118.42(18) . . ?
C17 C10 Br1 119.67(19) . . ?
C17 C10 C14 121.9(2) . . ?
C1 C11 H11 120.7 . . ?
C13 C11 C1 118.5(2) . . ?
C13 C11 H11 120.7 . . ?
C4 C12 H12 119.8 . . ?
C14 C12 C4 120.4(2) . . ?
C14 C12 H12 119.8 . . ?
C6 C13 H13 120.3 . . ?
C11 C13 C6 119.5(2) . . ?
C11 C13 H13 120.3 . . ?
C10 C14 H14 120.0 . . ?
C12 C14 C10 119.9(2) . . ?
C12 C14 H14 120.0 . . ?
C2 C15 C7 119.9(3) . . ?
C2 C15 H15 120.1 . . ?
C7 C15 H15 120.1 . . ?
C3 C16 C5 119.5(2) . . ?
C3 C16 C9 118.9(2) . . ?
C9 C16 C5 121.6(2) . . ?
C6 C17 H17 120.3 . . ?
C10 C17 C6 119.4(2) . . ?
C10 C17 H17 120.3 . . ?
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
Br1 C10 1.899(3) . ?
S1 C5 1.727(3) . ?
S1 C8 1.722(3) . ?
N1 C1 1.325(3) . ?
N1 C4 1.363(3) . ?
N2 N3 1.376(3) . ?
N2 C5 1.296(4) . ?
N3 C8 1.303(3) . ?
C1 C8 1.468(3) . ?
C1 C11 1.404(4) . ?
C2 H2 0.9400 . ?
C2 C3 1.379(4) . ?
C2 C15 1.379(4) . ?
C3 H3 0.9400 . ?
C3 C16 1.389(3) . ?
C4 C6 1.411(4) . ?
C4 C12 1.416(3) . ?
C5 C16 1.472(3) . ?
C6 C13 1.412(4) . ?
C6 C17 1.415(3) . ?
C7 H7 0.9400 . ?
C7 C9 1.381(4) . ?
C7 C15 1.384(4) . ?
C9 H9 0.9400 . ?
C9 C16 1.390(4) . ?
C10 C14 1.392(4) . ?
C10 C17 1.364(3) . ?
C11 H11 0.9400 . ?
C11 C13 1.358(4) . ?
C12 H12 0.9400 . ?
C12 C14 1.360(4) . ?
C13 H13 0.9400 . ?
C14 H14 0.9400 . ?
C15 H15 0.9400 . ?
C17 H17 0.9400 . ?
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
Br1 C10 C14 C12 -179.07(19) . . . . ?
Br1 C10 C17 C6 178.98(19) . . . . ?
S1 C5 C16 C3 -172.5(2) . . . . ?
S1 C5 C16 C9 8.1(3) . . . . ?
N1 C1 C8 S1 3.5(3) . . . . ?
N1 C1 C8 N3 -177.4(2) . . . . ?
N1 C1 C11 C13 -1.8(4) . . . . ?
N1 C4 C6 C13 -1.8(4) . . . . ?
N1 C4 C6 C17 179.3(2) . . . . ?
N1 C4 C12 C14 -179.4(2) . . . . ?
N2 N3 C8 S1 -0.5(3) . . . . ?
N2 N3 C8 C1 -179.6(2) . . . . ?
N2 C5 C16 C3 6.8(4) . . . . ?
N2 C5 C16 C9 -172.6(2) . . . . ?
N3 N2 C5 S1 -0.5(3) . . . . ?
N3 N2 C5 C16 -179.9(2) . . . . ?
C1 N1 C4 C6 1.7(3) . . . . ?
C1 N1 C4 C12 -178.4(2) . . . . ?
C1 C11 C13 C6 1.6(4) . . . . ?
C2 C3 C16 C5 -179.0(2) . . . . ?
C2 C3 C16 C9 0.4(4) . . . . ?
C3 C2 C15 C7 0.0(4) . . . . ?
C4 N1 C1 C8 -178.9(2) . . . . ?
C4 N1 C1 C11 0.2(4) . . . . ?
C4 C6 C13 C11 0.1(4) . . . . ?
C4 C6 C17 C10 0.6(4) . . . . ?
C4 C12 C14 C10 -0.4(4) . . . . ?
C5 S1 C8 N3 0.1(2) . . . . ?
C5 S1 C8 C1 179.3(2) . . . . ?
C5 N2 N3 C8 0.6(3) . . . . ?
C6 C4 C12 C14 0.6(4) . . . . ?
C7 C9 C16 C3 -0.6(4) . . . . ?
C7 C9 C16 C5 178.8(2) . . . . ?
C8 S1 C5 N2 0.2(2) . . . . ?
C8 S1 C5 C16 179.6(2) . . . . ?
C8 C1 C11 C13 177.2(2) . . . . ?
C9 C7 C15 C2 -0.2(4) . . . . ?
C11 C1 C8 S1 -175.5(2) . . . . ?
C11 C1 C8 N3 3.5(4) . . . . ?
C12 C4 C6 C13 178.2(2) . . . . ?
C12 C4 C6 C17 -0.7(4) . . . . ?
C13 C6 C17 C10 -178.3(2) . . . . ?
C14 C10 C17 C6 -0.3(4) . . . . ?
C15 C2 C3 C16 0.0(4) . . . . ?
C15 C7 C9 C16 0.5(4) . . . . ?
C17 C6 C13 C11 178.9(3) . . . . ?
C17 C10 C14 C12 0.2(4) . . . . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.471 0.250 115.0 36.2 '0.6 CHCl3'
2 0.000 -0.634 0.750 115.0 36.2 '0.6 CHCl3'
3 0.500 -0.639 0.250 115.0 36.2 '0.6 CHCl3'
4 0.500 -0.875 0.750 115.0 36.2 '0.6 CHCl3'
