#------------------------------------------------------------------------------
#$Date: 2019-11-28 18:29:55 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244285 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/86/7238678.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_7238678
loop_
_publ_author_name
'Paul, Rajesh'
'Punniyamurthy, Tharmalingam'
_publ_section_title
;
 Copper-catalysed one-pot synthesis of N-substituted
 benzo[d]isothiazol-3(2H)-ones via C-S/N-S bond formation
;
_journal_issue                   18
_journal_name_full               'RSC Advances'
_journal_page_first              7057
_journal_paper_doi               10.1039/c2ra20724a
_journal_volume                  2
_journal_year                    2012
_chemical_formula_sum            'C14 H11 N O2 S'
_chemical_formula_weight         257.31
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.028(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5093(14)
_cell_length_b                   13.6166(17)
_cell_length_c                   9.1287(12)
_cell_measurement_reflns_used    5668
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.94
_cell_measurement_theta_min      2.85
_cell_volume                     1193.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15718
_diffrn_reflns_theta_full        29.94
_diffrn_reflns_theta_max         29.94
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADBAS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0049(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0345P)²+0.2869P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0947
_reflns_number_gt                3340
_reflns_number_total             3382
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ra20724a.txt
_cod_data_source_block           platon
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7238678
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.19664(4) 0.03386(3) 0.35189(5) 0.04736(14) Uani 1 1 d .
O2 O -0.13855(12) 0.40800(8) -0.11190(15) 0.0584(3) Uani 1 1 d .
O1 O 0.33087(13) 0.09770(8) 0.03293(14) 0.0571(3) Uani 1 1 d .
N1 N 0.21164(13) 0.09647(9) 0.19618(15) 0.0449(3) Uani 1 1 d .
C12 C -0.08157(18) 0.23443(12) -0.1067(2) 0.0560(5) Uani 1 1 d .
H12 H -0.1557 0.2228 -0.2047 0.067 Uiso 1 1 calc R
C13 C 0.00702(19) 0.15904(12) -0.0258(2) 0.0572(5) Uani 1 1 d .
H13 H -0.0076 0.0964 -0.0703 0.069 Uiso 1 1 calc R
C8 C 0.11635(16) 0.17518(10) 0.11919(18) 0.0418(4) Uani 1 1 d .
C9 C 0.13568(16) 0.26729(11) 0.1882(2) 0.0480(4) Uani 1 1 d .
H9 H 0.2073 0.2781 0.2885 0.058 Uiso 1 1 calc R
C10 C 0.04853(17) 0.34302(11) 0.1079(2) 0.0515(4) Uani 1 1 d .
H10 H 0.0621 0.4052 0.1538 0.062 Uiso 1 1 calc R
C11 C -0.05900(15) 0.32728(11) -0.04043(19) 0.0436(4) Uani 1 1 d .
C14 C -0.2300(2) 0.40059(15) -0.2778(2) 0.0714(6) Uani 1 1 d .
H14A H -0.3037 0.3553 -0.2904 0.107 Uiso 1 1 calc R
H14B H -0.1788 0.3776 -0.3374 0.107 Uiso 1 1 calc R
H14C H -0.2689 0.4640 -0.3172 0.107 Uiso 1 1 calc R
C6 C 0.37376(15) -0.02615(10) 0.23797(18) 0.0406(3) Uani 1 1 d .
C5 C 0.47487(17) -0.08520(12) 0.2197(2) 0.0502(4) Uani 1 1 d .
H5 H 0.5071 -0.0712 0.1411 0.060 Uiso 1 1 calc R
C4 C 0.52605(18) -0.16450(13) 0.3202(2) 0.0562(4) Uani 1 1 d .
H4 H 0.5927 -0.2049 0.3086 0.067 Uiso 1 1 calc R
C3 C 0.47895(18) -0.18465(12) 0.4388(2) 0.0556(4) Uani 1 1 d .
H3 H 0.5156 -0.2382 0.5063 0.067 Uiso 1 1 calc R
C2 C 0.37931(17) -0.12741(12) 0.45913(19) 0.0506(4) Uani 1 1 d .
H2 H 0.3488 -0.1413 0.5392 0.061 Uiso 1 1 calc R
C1 C 0.32556(15) -0.04778(11) 0.35566(18) 0.0419(4) Uani 1 1 d .
C7 C 0.30786(16) 0.06074(11) 0.14214(19) 0.0430(4) Uani 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
N1 S1 C1 90.02(7)
C11 O2 C14 117.59(13)
C7 N1 C8 123.55(13)
C7 N1 S1 116.59(10)
C8 N1 S1 119.55(10)
C11 C12 C13 119.27(15)
C11 C12 H12 120.4
C13 C12 H12 120.4
C8 C13 C12 120.95(14)
C8 C13 H13 119.5
C12 C13 H13 119.5
C13 C8 C9 119.70(14)
C13 C8 N1 119.65(13)
C9 C8 N1 120.64(14)
C10 C9 C8 119.70(15)
C10 C9 H9 120.1
C8 C9 H9 120.1
C9 C10 C11 120.47(14)
C9 C10 H10 119.8
C11 C10 H10 119.8
C12 C11 O2 124.20(14)
C12 C11 C10 119.84(14)
O2 C11 C10 115.96(13)
O2 C14 H14A 109.5
O2 C14 H14B 109.5
H14A C14 H14B 109.5
O2 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C1 C6 C5 120.26(14)
C1 C6 C7 113.50(14)
C5 C6 C7 126.24(15)
C4 C5 C6 118.84(16)
C4 C5 H5 120.6
C6 C5 H5 120.6
C5 C4 C3 120.52(16)
C5 C4 H4 119.7
C3 C4 H4 119.7
C2 C3 C4 121.66(16)
C2 C3 H3 119.2
C4 C3 H3 119.2
C3 C2 C1 117.94(16)
C3 C2 H2 121.0
C1 C2 H2 121.0
C6 C1 C2 120.76(15)
C6 C1 S1 111.96(11)
C2 C1 S1 127.28(13)
O1 C7 N1 124.16(14)
O1 C7 C6 127.93(15)
N1 C7 C6 107.91(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 N1 1.7189(13)
S1 C1 1.7420(16)
O2 C11 1.3742(18)
O2 C14 1.429(2)
O1 C7 1.2255(18)
N1 C7 1.382(2)
N1 C8 1.4395(19)
C12 C11 1.380(2)
C12 C13 1.381(2)
C12 H12 0.9300
C13 C8 1.372(2)
C13 H13 0.9300
C8 C9 1.381(2)
C9 C10 1.376(2)
C9 H9 0.9300
C10 C11 1.382(2)
C10 H10 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C6 C1 1.393(2)
C6 C5 1.395(2)
C6 C7 1.467(2)
C5 C4 1.376(2)
C5 H5 0.9300
C4 C3 1.389(3)
C4 H4 0.9300
C3 C2 1.377(2)
C3 H3 0.9300
C2 C1 1.397(2)
C2 H2 0.9300
