#------------------------------------------------------------------------------
#$Date: 2024-06-28 12:32:51 +0300 (Fri, 28 Jun 2024) $
#$Revision: 292638 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157511.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_7157511
loop_
_publ_author_name
'Singh, Manpreet'
'Vaishali, ?'
'Paul, Avijit Kumar'
'Singh, Virender'
_publ_section_title
;
 Isatin as a 2-aminobenzaldehyde surrogate: transition metal-free
 efficient synthesis of 2-(2'-aminophenyl)benzothiazole derivatives.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4459
_journal_page_last               4469
_journal_paper_doi               10.1039/d0ob00888e
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C14 H10 N2 O2 S'
_chemical_formula_weight         270.30
_chemical_name_common            NRVS1
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-01-30 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.677(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.7318(10)
_cell_length_b                   9.1027(7)
_cell_length_c                   20.8094(15)
_cell_measurement_reflns_used    4170
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.997
_cell_measurement_theta_min      1.610
_cell_volume                     2395.3(3)
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_collection       'Apex3 v2016.9-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23759
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.610
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2016/2)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Block like'
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0415
_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)+(0.0618P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1191
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2928
_reflns_number_total             4170
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00888e2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157511.cif.

 Adding full bibliography for 7157511.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C28 H20 N4 O4 S2'
_cod_original_formula_weight         540.60
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157511
_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.
;
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
S2 S -0.06976(5) 0.39289(7) 0.59331(3) 0.0520(2) Uani 1 1 d . . . . .
S1 S 0.65130(5) 0.42043(7) 0.53822(3) 0.0518(2) Uani 1 1 d . . . . .
O1 O 0.43682(14) 0.0636(2) 0.37335(8) 0.0638(5) Uani 1 1 d . . . . .
O2 O 0.31302(14) 0.0243(2) 0.44420(8) 0.0659(5) Uani 1 1 d . . . . .
O3 O 0.02740(17) 0.0440(2) 0.37524(9) 0.0767(6) Uani 1 1 d . . . . .
N2 N 0.50204(14) 0.3473(2) 0.60636(9) 0.0466(5) Uani 1 1 d . . . . .
N4 N 0.11787(15) 0.3763(2) 0.55835(9) 0.0505(5) Uani 1 1 d . . . . .
N1 N 0.50805(18) 0.4216(3) 0.73428(10) 0.0703(7) Uani 1 1 d . . . . .
H1A H 0.485199 0.419449 0.771565 0.084 Uiso 1 1 calc R U . . .
H1B H 0.479157 0.366976 0.703433 0.084 Uiso 1 1 calc R U . . .
N3 N 0.28874(16) 0.5161(2) 0.62284(11) 0.0688(6) Uani 1 1 d . . . . .
H3A H 0.354644 0.539094 0.629227 0.083 Uiso 1 1 calc R U . . .
H3B H 0.266020 0.459260 0.591237 0.083 Uiso 1 1 calc R U . . .
O4 O -0.14780(16) 0.0355(2) 0.39548(10) 0.0782(6) Uani 1 1 d . . . . .
C1 C 0.58976(19) 0.5112(3) 0.72410(11) 0.0530(6) Uani 1 1 d . . . . .
C20 C 0.11050(18) 0.5364(2) 0.65289(11) 0.0468(6) Uani 1 1 d . . . . .
C13 C 0.39509(18) 0.1818(3) 0.53138(11) 0.0490(6) Uani 1 1 d . . . . .
H13 H 0.344690 0.164457 0.559441 0.059 Uiso 1 1 calc R U . . .
C8 C 0.48141(17) 0.2743(2) 0.54765(10) 0.0439(5) Uani 1 1 d . . . . .
C12 C 0.38932(18) 0.1186(3) 0.47172(11) 0.0473(6) Uani 1 1 d . . . . .
C15 C 0.22034(18) 0.5697(3) 0.66278(12) 0.0511(6) Uani 1 1 d . . . . .
C6 C 0.63018(18) 0.5185(2) 0.66370(11) 0.0473(6) Uani 1 1 d . . . . .
C7 C 0.58724(18) 0.4280(2) 0.60856(11) 0.0446(5) Uani 1 1 d . . . . .
C9 C 0.55554(17) 0.3000(2) 0.50408(11) 0.0443(5) Uani 1 1 d . . . . .
C21 C 0.06573(18) 0.4379(2) 0.60113(11) 0.0458(6) Uani 1 1 d . . . . .
C27 C -0.1285(2) 0.2000(3) 0.48925(12) 0.0556(6) Uani 1 1 d . . . . .
H27 H -0.198848 0.196169 0.497134 0.067 Uiso 1 1 calc R U . . .
C19 C 0.0449(2) 0.5989(3) 0.69426(12) 0.0584(7) Uani 1 1 d . . . . .
H19 H -0.027066 0.577810 0.688046 0.070 Uiso 1 1 calc R U . . .
C11 C 0.46346(19) 0.1430(2) 0.42925(10) 0.0488(6) Uani 1 1 d . . . . .
C10 C 0.54779(19) 0.2327(3) 0.44297(11) 0.0509(6) Uani 1 1 d . . . . .
H10 H 0.597049 0.248740 0.414034 0.061 Uiso 1 1 calc R U . . .
C22 C -0.05250(18) 0.2837(2) 0.52726(11) 0.0476(6) Uani 1 1 d . . . . .
C5 C 0.71481(19) 0.6137(3) 0.65742(13) 0.0576(7) Uani 1 1 d . . . . .
H5 H 0.742153 0.619040 0.617945 0.069 Uiso 1 1 calc R U . . .
C18 C 0.0827(2) 0.6914(3) 0.74429(13) 0.0676(7) Uani 1 1 d . . . . .
H18 H 0.037149 0.732463 0.771161 0.081 Uiso 1 1 calc R U . . .
C23 C 0.05360(19) 0.2892(2) 0.51600(11) 0.0488(6) Uani 1 1 d . . . . .
C24 C 0.0889(2) 0.2088(3) 0.46450(12) 0.0572(7) Uani 1 1 d . . . . .
H24 H 0.159048 0.210020 0.456162 0.069 Uiso 1 1 calc R U . . .
C2 C 0.6365(2) 0.5999(3) 0.77442(13) 0.0679(8) Uani 1 1 d . . . . .
H2 H 0.611109 0.595586 0.814509 0.082 Uiso 1 1 calc R U . . .
C25 C 0.0138(2) 0.1300(3) 0.42809(12) 0.0561(6) Uani 1 1 d . . . . .
C26 C -0.0920(2) 0.1254(3) 0.44025(12) 0.0552(6) Uani 1 1 d . . . . .
C4 C 0.7589(2) 0.7001(3) 0.70828(16) 0.0697(8) Uani 1 1 d . . . . .
H4 H 0.815211 0.762383 0.703176 0.084 Uiso 1 1 calc R U . . .
C16 C 0.2569(2) 0.6621(3) 0.71425(13) 0.0657(7) Uani 1 1 d . . . . .
H16 H 0.328697 0.683481 0.721729 0.079 Uiso 1 1 calc R U . . .
C14 C 0.3418(2) -0.0119(3) 0.38186(12) 0.0612(7) Uani 1 1 d . . . . .
H14A H 0.352315 -0.117092 0.378663 0.073 Uiso 1 1 calc R U . . .
H14B H 0.285989 0.017120 0.348537 0.073 Uiso 1 1 calc R U . . .
C17 C 0.1902(2) 0.7216(3) 0.75360(14) 0.0715(8) Uani 1 1 d . . . . .
H17 H 0.216959 0.783368 0.787185 0.086 Uiso 1 1 calc R U . . .
C3 C 0.7180(2) 0.6922(3) 0.76646(15) 0.0737(9) Uani 1 1 d . . . . .
H3 H 0.746427 0.750669 0.800809 0.088 Uiso 1 1 calc R U . . .
C28 C -0.0746(2) -0.0173(3) 0.35453(14) 0.0728(8) Uani 1 1 d . . . . .
H28A H -0.097132 0.010935 0.310118 0.087 Uiso 1 1 calc R U . . .
H28B H -0.071160 -0.123669 0.356635 0.087 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'
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
C22 S2 C21 89.64(11) . . ?
C9 S1 C7 89.65(11) . . ?
C11 O1 C14 106.16(18) . . ?
C12 O2 C14 106.28(19) . . ?
C25 O3 C28 105.5(2) . . ?
C7 N2 C8 111.79(19) . . ?
C21 N4 C23 111.9(2) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C15 N3 H3A 120.0 . . ?
C15 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C26 O4 C28 106.5(2) . . ?
N1 C1 C2 119.8(2) . . ?
N1 C1 C6 122.1(2) . . ?
C2 C1 C6 118.1(2) . . ?
C19 C20 C15 118.4(2) . . ?
C19 C20 C21 119.7(2) . . ?
C15 C20 C21 121.9(2) . . ?
C12 C13 C8 115.7(2) . . ?
C12 C13 H13 122.2 . . ?
C8 C13 H13 122.2 . . ?
N2 C8 C13 124.4(2) . . ?
N2 C8 C9 114.6(2) . . ?
C13 C8 C9 121.0(2) . . ?
C13 C12 O2 127.3(2) . . ?
C13 C12 C11 123.1(2) . . ?
O2 C12 C11 109.7(2) . . ?
N3 C15 C16 120.2(2) . . ?
N3 C15 C20 121.5(2) . . ?
C16 C15 C20 118.2(2) . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 C7 119.7(2) . . ?
C1 C6 C7 121.9(2) . . ?
N2 C7 C6 125.2(2) . . ?
N2 C7 S1 114.35(17) . . ?
C6 C7 S1 120.48(18) . . ?
C8 C9 C10 122.1(2) . . ?
C8 C9 S1 109.61(17) . . ?
C10 C9 S1 128.33(18) . . ?
N4 C21 C20 125.6(2) . . ?
N4 C21 S2 114.16(18) . . ?
C20 C21 S2 120.22(17) . . ?
C26 C27 C22 115.0(2) . . ?
C26 C27 H27 122.5 . . ?
C22 C27 H27 122.5 . . ?
C18 C19 C20 122.3(3) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C10 C11 O1 127.3(2) . . ?
C10 C11 C12 123.1(2) . . ?
O1 C11 C12 109.6(2) . . ?
C11 C10 C9 115.1(2) . . ?
C11 C10 H10 122.4 . . ?
C9 C10 H10 122.4 . . ?
C23 C22 C27 122.8(2) . . ?
C23 C22 S2 109.07(18) . . ?
C27 C22 S2 128.12(19) . . ?
C4 C5 C6 121.9(3) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C19 C18 C17 118.6(3) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
N4 C23 C22 115.2(2) . . ?
N4 C23 C24 124.3(2) . . ?
C22 C23 C24 120.4(2) . . ?
C25 C24 C23 115.7(2) . . ?
C25 C24 H24 122.2 . . ?
C23 C24 H24 122.2 . . ?
C3 C2 C1 122.0(3) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C24 C25 O3 127.0(2) . . ?
C24 C25 C26 123.1(2) . . ?
O3 C25 C26 109.9(2) . . ?
C27 C26 O4 127.9(2) . . ?
C27 C26 C25 123.0(2) . . ?
O4 C26 C25 109.1(2) . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C17 C16 C15 121.7(3) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
O1 C14 O2 108.29(19) . . ?
O1 C14 H14A 110.0 . . ?
O2 C14 H14A 110.0 . . ?
O1 C14 H14B 110.0 . . ?
O2 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
O4 C28 O3 108.9(2) . . ?
O4 C28 H28A 109.9 . . ?
O3 C28 H28A 109.9 . . ?
O4 C28 H28B 109.9 . . ?
O3 C28 H28B 109.9 . . ?
H28A C28 H28B 108.3 . . ?
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
S2 C22 1.731(2) . ?
S2 C21 1.762(2) . ?
S1 C9 1.729(2) . ?
S1 C7 1.758(2) . ?
O1 C11 1.378(3) . ?
O1 C14 1.420(3) . ?
O2 C12 1.371(3) . ?
O2 C14 1.427(3) . ?
O3 C25 1.377(3) . ?
O3 C28 1.433(3) . ?
N2 C7 1.307(3) . ?
N2 C8 1.389(3) . ?
N4 C21 1.298(3) . ?
N4 C23 1.381(3) . ?
N1 C1 1.358(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N3 C15 1.362(3) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
O4 C26 1.374(3) . ?
O4 C28 1.418(3) . ?
C1 C2 1.399(4) . ?
C1 C6 1.414(3) . ?
C20 C19 1.389(3) . ?
C20 C15 1.422(3) . ?
C20 C21 1.465(3) . ?
C13 C12 1.363(3) . ?
C13 C8 1.394(3) . ?
C13 H13 0.9300 . ?
C8 C9 1.402(3) . ?
C12 C11 1.384(3) . ?
C15 C16 1.399(4) . ?
C6 C5 1.401(3) . ?
C6 C7 1.465(3) . ?
C9 C10 1.405(3) . ?
C27 C26 1.352(3) . ?
C27 C22 1.401(3) . ?
C27 H27 0.9300 . ?
C19 C18 1.381(3) . ?
C19 H19 0.9300 . ?
C11 C10 1.353(3) . ?
C10 H10 0.9300 . ?
C22 C23 1.398(3) . ?
C5 C4 1.384(4) . ?
C5 H5 0.9300 . ?
C18 C17 1.387(4) . ?
C18 H18 0.9300 . ?
C23 C24 1.413(3) . ?
C24 C25 1.354(3) . ?
C24 H24 0.9300 . ?
C2 C3 1.360(4) . ?
C2 H2 0.9300 . ?
C25 C26 1.400(4) . ?
C4 C3 1.374(4) . ?
C4 H4 0.9300 . ?
C16 C17 1.359(4) . ?
C16 H16 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C17 H17 0.9300 . ?
C3 H3 0.9300 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
