#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/31/1513146.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_1513146
loop_
_publ_author_name
'Singh, Neetu'
'Singh, Rahul'
'Raghuvanshi, Dushyant S.'
'Singh, Krishna Nand'
_publ_section_title
;
 Convenient MW-Assisted Synthesis of Unsymmetrical Sulfides Using Sulfonyl
 Hydrazides as Aryl Thiol Surrogate
;
_journal_issue                   22
_journal_name_full               'Organic Letters'
_journal_page_first              5874
_journal_paper_doi               10.1021/ol402948k
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C13 H11 N O2 S'
_chemical_formula_sum            'C13 H11 N O2 S'
_chemical_formula_weight         245.29
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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                 112.890(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.173(14)
_cell_length_b                   8.197(13)
_cell_length_c                   14.575(16)
_cell_measurement_reflns_used    2090
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1230(3)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_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  0.1704
_diffrn_reflns_av_sigmaI/netI    0.0885
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8447
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.9514
_exptl_absorpt_correction_T_min  0.9061
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Acta Crystallogr A. (1995), 51, 33'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2478
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0848
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1373P)²+0.1344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2173
_refine_ls_wR_factor_ref         0.2402
_reflns_number_gt                1972
_reflns_number_total             2478
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol402948k_si_001.cif
_cod_data_source_block           datam
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1513146
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
C1 C 0.9709(3) 0.1522(4) 0.3470(2) 0.0564(8) Uani 1 1 d .
C2 C 1.0071(3) 0.0779(4) 0.2771(3) 0.0660(9) Uani 1 1 d .
H2 H 1.0872 0.0261 0.2959 0.079 Uiso 1 1 calc R
C3 C 0.9220(3) 0.0818(4) 0.1780(2) 0.0640(8) Uani 1 1 d .
H3 H 0.9456 0.0329 0.1299 0.077 Uiso 1 1 calc R
C4 C 0.8001(3) 0.1588(3) 0.1493(2) 0.0465(6) Uani 1 1 d .
C5 C 0.7664(3) 0.2330(4) 0.2225(2) 0.0589(8) Uani 1 1 d .
H5 H 0.6861 0.2840 0.2048 0.071 Uiso 1 1 calc R
C6 C 0.8530(3) 0.2305(5) 0.3221(2) 0.0651(9) Uani 1 1 d .
H6 H 0.8316 0.2808 0.3708 0.078 Uiso 1 1 calc R
C7 C 0.5712(3) 0.3002(4) 0.0085(2) 0.0626(8) Uani 1 1 d .
H7B H 0.5182 0.2620 0.0434 0.075 Uiso 1 1 calc R
H7A H 0.6091 0.4043 0.0367 0.075 Uiso 1 1 calc R
C8 C 0.4881(3) 0.3193(3) -0.1023(2) 0.0509(7) Uani 1 1 d .
C9 C 0.5322(3) 0.4125(4) -0.1623(2) 0.0595(8) Uani 1 1 d .
H9 H 0.6121 0.4650 -0.1346 0.071 Uiso 1 1 calc R
C10 C 0.4575(3) 0.4279(4) -0.2638(2) 0.0676(9) Uani 1 1 d .
H10 H 0.4879 0.4906 -0.3034 0.081 Uiso 1 1 calc R
C11 C 0.3381(3) 0.3504(4) -0.3063(2) 0.0669(9) Uani 1 1 d .
H11 H 0.2884 0.3612 -0.3741 0.080 Uiso 1 1 calc R
C12 C 0.2931(3) 0.2566(4) -0.2471(3) 0.0680(9) Uani 1 1 d .
H12 H 0.2133 0.2039 -0.2751 0.082 Uiso 1 1 calc R
C13 C 0.3687(3) 0.2416(4) -0.1446(2) 0.0585(7) Uani 1 1 d .
H13 H 0.3384 0.1791 -0.1049 0.070 Uiso 1 1 calc R
N1 N 1.0646(3) 0.1547(4) 0.4532(2) 0.0775(9) Uani 1 1 d .
O1A O 1.1661(3) 0.0808(5) 0.4748(2) 0.1226(13) Uani 1 1 d .
O1B O 1.0363(3) 0.2324(6) 0.5125(2) 0.1327(15) Uani 1 1 d .
S1 S 0.69870(8) 0.15280(9) 0.02129(5) 0.0586(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
C2 C1 C6 122.4(3)
C2 C1 N1 118.9(3)
C6 C1 N1 118.6(3)
C1 C2 C3 118.8(3)
C1 C2 H2 120.6
C3 C2 H2 120.6
C2 C3 C4 120.8(3)
C2 C3 H3 119.6
C4 C3 H3 119.6
C5 C4 C3 119.0(3)
C5 C4 S1 124.3(2)
C3 C4 S1 116.7(2)
C6 C5 C4 120.1(3)
C6 C5 H5 119.9
C4 C5 H5 119.9
C1 C6 C5 119.0(3)
C1 C6 H6 120.5
C5 C6 H6 120.5
C8 C7 S1 107.8(2)
C8 C7 H7B 110.1
S1 C7 H7B 110.1
C8 C7 H7A 110.1
S1 C7 H7A 110.1
H7B C7 H7A 108.5
C9 C8 C13 119.2(3)
C9 C8 C7 120.3(3)
C13 C8 C7 120.5(3)
C8 C9 C10 120.4(3)
C8 C9 H9 119.8
C10 C9 H9 119.8
C11 C10 C9 120.5(3)
C11 C10 H10 119.8
C9 C10 H10 119.8
C12 C11 C10 119.6(3)
C12 C11 H11 120.2
C10 C11 H11 120.2
C11 C12 C13 119.7(3)
C11 C12 H12 120.2
C13 C12 H12 120.2
C8 C13 C12 120.6(3)
C8 C13 H13 119.7
C12 C13 H13 119.7
O1B N1 O1A 123.6(3)
O1B N1 C1 118.3(3)
O1A N1 C1 118.0(4)
C4 S1 C7 104.15(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.376(5)
C1 C6 1.381(5)
C1 N1 1.494(4)
C2 C3 1.386(4)
C2 H2 0.9300
C3 C4 1.409(4)
C3 H3 0.9300
C4 C5 1.402(4)
C4 S1 1.768(3)
C5 C6 1.396(4)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.525(4)
C7 S1 1.822(4)
C7 H7B 0.9700
C7 H7A 0.9700
C8 C9 1.388(4)
C8 C13 1.388(4)
C9 C10 1.393(4)
C9 H9 0.9300
C10 C11 1.387(5)
C10 H10 0.9300
C11 C12 1.387(5)
C11 H11 0.9300
C12 C13 1.407(4)
C12 H12 0.9300
C13 H13 0.9300
N1 O1B 1.211(5)
N1 O1A 1.214(5)
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
C6 C1 C2 C3 0.0(5)
N1 C1 C2 C3 -177.4(3)
C1 C2 C3 C4 -0.6(5)
C2 C3 C4 C5 0.5(5)
C2 C3 C4 S1 -178.9(3)
C3 C4 C5 C6 0.2(5)
S1 C4 C5 C6 179.6(2)
C2 C1 C6 C5 0.8(5)
N1 C1 C6 C5 178.1(3)
C4 C5 C6 C1 -0.9(5)
S1 C7 C8 C9 -77.3(3)
S1 C7 C8 C13 101.5(3)
C13 C8 C9 C10 0.0(5)
C7 C8 C9 C10 178.9(3)
C8 C9 C10 C11 0.0(5)
C9 C10 C11 C12 -0.2(5)
C10 C11 C12 C13 0.3(5)
C9 C8 C13 C12 0.1(4)
C7 C8 C13 C12 -178.8(3)
C11 C12 C13 C8 -0.2(5)
C2 C1 N1 O1B 173.7(4)
C6 C1 N1 O1B -3.7(5)
C2 C1 N1 O1A -5.1(5)
C6 C1 N1 O1A 177.5(4)
C5 C4 S1 C7 13.3(3)
C3 C4 S1 C7 -167.3(2)
C8 C7 S1 C4 172.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 1485576
