#------------------------------------------------------------------------------
#$Date: 2023-04-20 14:53:48 +0300 (Thu, 20 Apr 2023) $
#$Revision: 282777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/77/1567719.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_1567719
loop_
_publ_author_name
'Dhara, Samiran'
'Saha, Moumita'
'Das, Asish R.'
_publ_section_title
;
 Ligand-free access to benzisothiazolones and benzisoselenazolones through
 NiFe ₂ O ₄ catalyzed concomitant annulation of
 2-halobenzanilides with chalcogens and their late-stage transformations
;
_journal_issue                   40
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19501
_journal_page_last               19513
_journal_paper_doi               10.1039/D2NJ04326B
_journal_volume                  46
_journal_year                    2022
_chemical_formula_sum            'C14 H11 N O S'
_chemical_formula_weight         241.30
_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   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2022-04-08 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.172(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6609(7)
_cell_length_b                   6.3361(5)
_cell_length_c                   19.6298(14)
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.995
_cell_measurement_theta_min      2.087
_cell_volume                     1194.62(15)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9949
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.087
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.027(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0645
_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)+(0.1000P)²+0.9269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1727
_refine_ls_wR_factor_ref         0.1767
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1906
_reflns_number_total             2109
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj04326b2.cif
_cod_data_source_block           AP_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1567719
_shelx_shelxl_version_number     2017/1
_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
S001 S 0.57110(7) 0.61097(12) 0.58140(4) 0.0590(4) Uani 1 1 d . . . . .
O002 O 0.9271(2) 0.6416(4) 0.68292(11) 0.0592(6) Uani 1 1 d . . . . .
N1 N 0.7323(2) 0.7055(4) 0.60819(11) 0.0481(6) Uani 1 1 d . . . . .
C2 C 0.7282(2) 0.4081(4) 0.67560(12) 0.0392(6) Uani 1 1 d . . . . .
C9 C 0.8074(3) 0.8806(4) 0.50471(13) 0.0441(6) Uani 1 1 d . . . . .
C1 C 0.8095(3) 0.5909(4) 0.65829(12) 0.0413(6) Uani 1 1 d . . . . .
C3 C 0.5961(3) 0.4006(4) 0.63820(14) 0.0443(6) Uani 1 1 d . . . . .
C7 C 0.7683(3) 0.2496(5) 0.72256(13) 0.0502(7) Uani 1 1 d . . . . .
C4 C 0.5032(3) 0.2392(5) 0.64809(16) 0.0569(8) Uani 1 1 d . . . . .
C8 C 0.7808(4) 0.8999(4) 0.57884(15) 0.0543(7) Uani 1 1 d . . . . .
C10 C 0.8552(3) 0.6958(5) 0.47820(16) 0.0580(8) Uani 1 1 d . . . . .
C14 C 0.7901(3) 1.0562(5) 0.46335(16) 0.0586(8) Uani 1 1 d . . . . .
C5 C 0.5432(4) 0.0877(5) 0.69578(18) 0.0630(9) Uani 1 1 d . . . . .
C6 C 0.6757(4) 0.0908(5) 0.73274(16) 0.0617(8) Uani 1 1 d . . . . .
C11 C 0.8871(3) 0.6890(7) 0.41054(19) 0.0710(10) Uani 1 1 d . . . . .
C12 C 0.8714(4) 0.8666(8) 0.37015(18) 0.0776(12) Uani 1 1 d . . . . .
C13 C 0.8228(4) 1.0480(7) 0.39639(18) 0.0765(11) Uani 1 1 d . . . . .
H1 H 0.413(5) 0.249(7) 0.625(2) 0.103(14) Uiso 1 1 d . . . . .
H2 H 0.488(4) -0.023(7) 0.7048(19) 0.076(11) Uiso 1 1 d . . . . .
H3 H 0.696(3) -0.020(6) 0.7629(18) 0.066(9) Uiso 1 1 d . . . . .
H4 H 0.856(4) 0.257(6) 0.743(2) 0.077(11) Uiso 1 1 d . . . . .
H5 H 0.705(4) 1.007(7) 0.5856(19) 0.078(10) Uiso 1 1 d . . . . .
H6 H 0.872(5) 0.937(6) 0.607(2) 0.085(12) Uiso 1 1 d . . . . .
H7 H 0.871(4) 0.568(6) 0.505(2) 0.085(12) Uiso 1 1 d . . . . .
H8 H 0.916(4) 0.557(6) 0.396(2) 0.076(11) Uiso 1 1 d . . . . .
H9 H 0.903(5) 0.863(7) 0.324(3) 0.119(17) Uiso 1 1 d . . . . .
H10 H 0.817(5) 1.177(8) 0.371(3) 0.109(15) Uiso 1 1 d . . . . .
H11 H 0.753(4) 1.183(6) 0.4817(17) 0.065(9) Uiso 1 1 d . . . . .
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
N1 S001 C3 90.71(11) . . ?
C1 N1 C8 123.7(2) . . ?
C1 N1 S001 116.34(18) . . ?
C8 N1 S001 119.9(2) . . ?
C7 C2 C3 119.7(2) . . ?
C7 C2 C1 127.6(2) . . ?
C3 C2 C1 112.8(2) . . ?
C14 C9 C10 119.2(3) . . ?
C14 C9 C8 118.7(3) . . ?
C10 C9 C8 122.0(2) . . ?
O002 C1 N1 123.4(2) . . ?
O002 C1 C2 127.8(2) . . ?
N1 C1 C2 108.8(2) . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 S001 127.4(2) . . ?
C2 C3 S001 111.43(19) . . ?
C6 C7 C2 119.1(3) . . ?
C6 C7 H4 125(2) . . ?
C2 C7 H4 116(3) . . ?
C5 C4 C3 118.3(3) . . ?
C5 C4 H1 123(3) . . ?
C3 C4 H1 118(3) . . ?
N1 C8 C9 114.1(2) . . ?
N1 C8 H5 104(2) . . ?
C9 C8 H5 112(2) . . ?
N1 C8 H6 107(2) . . ?
C9 C8 H6 108(2) . . ?
H5 C8 H6 112(3) . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 H7 123(2) . . ?
C11 C10 H7 117(2) . . ?
C9 C14 C13 120.2(3) . . ?
C9 C14 H11 119(2) . . ?
C13 C14 H11 121(2) . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H2 123(3) . . ?
C6 C5 H2 116(2) . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 H3 123(2) . . ?
C5 C6 H3 116(2) . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H8 125(2) . . ?
C10 C11 H8 115(2) . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H9 121(3) . . ?
C11 C12 H9 119(3) . . ?
C12 C13 C14 120.9(4) . . ?
C12 C13 H10 122(3) . . ?
C14 C13 H10 117(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
S001 N1 1.698(2) . ?
S001 C3 1.738(3) . ?
O002 C1 1.229(3) . ?
N1 C1 1.376(3) . ?
N1 C8 1.458(4) . ?
C2 C7 1.390(4) . ?
C2 C3 1.403(3) . ?
C2 C1 1.460(4) . ?
C9 C14 1.377(4) . ?
C9 C10 1.381(4) . ?
C9 C8 1.510(4) . ?
C3 C4 1.388(4) . ?
C7 C6 1.375(5) . ?
C7 H4 0.90(4) . ?
C4 C5 1.367(5) . ?
C4 H1 0.93(5) . ?
C8 H5 1.02(4) . ?
C8 H6 1.01(4) . ?
C10 C11 1.396(5) . ?
C10 H7 0.96(4) . ?
C14 C13 1.385(5) . ?
C14 H11 0.97(3) . ?
C5 C6 1.402(5) . ?
C5 H2 0.91(4) . ?
C6 H3 0.93(4) . ?
C11 C12 1.376(6) . ?
C11 H8 0.94(4) . ?
C12 C13 1.363(6) . ?
C12 H9 0.99(6) . ?
C13 H10 0.96(5) . ?
