#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:56:51 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299065 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160221.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_7160221
loop_
_publ_author_name
'Dolas, Atul Jankiram'
'Yadav, Jyothi'
'Nagare, Yadav Kacharu'
'Rangan, Krishnan'
'Iype, Eldhose'
'Kumar, Indresh'
_publ_section_title
;
 Enantioselective synthesis of α-(3-pyrrolyl)methanamines with an
 aza-tetrasubstituted center under metal-free conditions.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              98
_journal_page_last               102
_journal_paper_doi               10.1039/d4ob01729c
_journal_volume                  23
_journal_year                    2024
_chemical_formula_moiety         'C13 H14 N2 O3 S'
_chemical_formula_sum            'C13 H14 N2 O3 S'
_chemical_formula_weight         278.32
_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     dual
_audit_creation_date             2023-02-02
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-06-07 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.644(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0312(2)
_cell_length_b                   16.1924(3)
_cell_length_c                   9.2203(2)
_cell_measurement_reflns_used    4146
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      79.2810
_cell_measurement_theta_min      4.9050
_cell_volume                     1336.37(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  13.00   0.50    1.03    --    0.00 -57.00-120.00   84
  2  ω    -88.00 -52.00   0.50    1.03    --    0.00 -57.00-120.00   72
  3  ω    -87.00 -49.00   0.50    1.03    --    0.00 -57.00 -30.00   76
  4  ω    -39.00  20.00   0.50    1.03    --    0.00 -57.00 -30.00  118
  5  ω     36.00 139.00   0.50    4.11    --  107.20 -82.00 -30.00  206
  6  ω     84.00 150.00   0.50    4.11    --  107.20  15.00  90.00  132
  7  ω     91.00 127.00   0.50    4.11    --  107.20 -30.00 -30.00   72
  8  ω     26.00  52.00   0.50    4.11    --  107.20 -82.00 -90.00   52
  9  ω     52.00  85.00   0.50    4.11    --  107.20 -30.00 -30.00   66
 10  ω     68.00 108.00   0.50    4.11    --  107.20 -82.00 -90.00   80
 11  ω     21.00 135.00   0.50    4.11    --  107.20 -15.00-120.00  228
 12  ω     20.00  56.00   0.50    4.11    --  107.20 -30.00 -90.00   72
 13  ω     83.00 110.00   0.50    4.11    --  107.20 -30.00 -90.00   54
 14  ω     20.00 132.00   0.50    4.11    --  107.20 -61.00 -30.00  224
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0783438000
_diffrn_orient_matrix_UB_12      -0.0113111000
_diffrn_orient_matrix_UB_13      -0.1576453000
_diffrn_orient_matrix_UB_21      0.1531228000
_diffrn_orient_matrix_UB_22      -0.0020923000
_diffrn_orient_matrix_UB_23      -0.0561990000
_diffrn_orient_matrix_UB_31      0.0058049000
_diffrn_orient_matrix_UB_32      -0.0944594000
_diffrn_orient_matrix_UB_33      0.0201268000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7241
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.568
_diffrn_reflns_theta_min         4.941
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.217
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0404
_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)+(0.0549P)²+0.6433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1129
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2508
_reflns_number_total             2808
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01729c2.cif
_cod_data_source_block           exp_1355_ad-686_20230202
_cod_depositor_comments
'Adding full bibliography for 7160220--7160222.cif.'
_cod_database_code               7160221
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C13 H14 N2 O3 S'
_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.
;
_shelx_estimated_absorpt_t_max   0.897
_shelx_estimated_absorpt_t_min   0.793
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.014
_oxdiff_exptl_absorpt_empirical_full_min 0.763
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
S1 S 0.29142(4) 0.42753(2) 0.50636(4) 0.02471(14) Uani 1 1 d . . . . .
O1 O 0.35341(14) 0.36921(7) 0.63990(14) 0.0294(3) Uani 1 1 d . . . . .
O2 O 0.14040(14) 0.40528(8) 0.46049(14) 0.0308(3) Uani 1 1 d . . . . .
O3 O 0.39860(16) 0.42018(8) 0.40740(16) 0.0361(3) Uani 1 1 d . . . . .
N1 N 0.29611(17) 0.51797(8) 0.57655(16) 0.0261(3) Uani 1 1 d . . . . .
H1 H 0.349136 0.558533 0.546249 0.031 Uiso 1 1 calc R U . . .
N2 N 0.20634(17) 0.74099(8) 0.83215(16) 0.0270(3) Uani 1 1 d . . . . .
C1 C 0.29036(19) 0.38087(10) 0.77104(19) 0.0257(3) Uani 1 1 d . . . . .
C2 C 0.22646(18) 0.45571(10) 0.80409(18) 0.0228(3) Uani 1 1 d . . . . .
C3 C 0.1737(2) 0.46096(11) 0.9391(2) 0.0301(4) Uani 1 1 d . . . . .
H3 H 0.131048 0.511358 0.966190 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1817(2) 0.39462(12) 1.0349(2) 0.0375(4) Uani 1 1 d . . . . .
H4 H 0.144515 0.399675 1.126140 0.045 Uiso 1 1 calc R U . . .
C5 C 0.2443(3) 0.32084(12) 0.9967(2) 0.0415(5) Uani 1 1 d . . . . .
H5 H 0.249227 0.275125 1.061772 0.050 Uiso 1 1 calc R U . . .
C6 C 0.2996(2) 0.31351(11) 0.8646(2) 0.0355(4) Uani 1 1 d . . . . .
H6 H 0.343072 0.263190 0.838295 0.043 Uiso 1 1 calc R U . . .
C7 C 0.20305(18) 0.52790(9) 0.69781(17) 0.0219(3) Uani 1 1 d . . . . .
H7 H 0.095831 0.527524 0.653370 0.026 Uiso 1 1 calc R U . . .
C8 C 0.23517(19) 0.61055(9) 0.76722(18) 0.0233(3) Uani 1 1 d . . . . .
C9 C 0.13889(19) 0.67656(10) 0.75420(18) 0.0244(3) Uani 1 1 d . . . . .
H9 H 0.041746 0.677238 0.700065 0.029 Uiso 1 1 calc R U . . .
C10 C 0.3457(2) 0.71736(11) 0.8930(2) 0.0335(4) Uani 1 1 d . . . . .
H10 H 0.416068 0.751185 0.951307 0.040 Uiso 1 1 calc R U . . .
C11 C 0.3674(2) 0.63667(11) 0.8561(2) 0.0320(4) Uani 1 1 d . . . . .
H11 H 0.454249 0.604408 0.884497 0.038 Uiso 1 1 calc R U . . .
C12 C 0.1437(2) 0.82418(11) 0.8378(2) 0.0342(4) Uani 1 1 d . . . . .
H12A H 0.168168 0.846356 0.938240 0.041 Uiso 1 1 calc R U . . .
H12B H 0.033567 0.821080 0.815410 0.041 Uiso 1 1 calc R U . . .
C13 C 0.2026(3) 0.88220(12) 0.7317(2) 0.0459(5) Uani 1 1 d . . . . .
H13A H 0.174139 0.862020 0.631622 0.069 Uiso 1 1 calc R U . . .
H13B H 0.311703 0.885057 0.752764 0.069 Uiso 1 1 calc R U . . .
H13C H 0.160216 0.937333 0.741384 0.069 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O1 S1 N1 104.02(7) . . ?
O2 S1 O1 107.74(8) . . ?
O2 S1 O3 119.81(8) . . ?
O2 S1 N1 109.00(8) . . ?
O3 S1 O1 104.32(8) . . ?
O3 S1 N1 110.67(8) . . ?
C1 O1 S1 116.17(10) . . ?
S1 N1 H1 122.8 . . ?
C7 N1 S1 114.47(10) . . ?
C7 N1 H1 122.8 . . ?
C9 N2 C12 125.10(16) . . ?
C10 N2 C9 108.99(14) . . ?
C10 N2 C12 125.69(15) . . ?
C2 C1 O1 121.87(15) . . ?
C6 C1 O1 115.39(15) . . ?
C6 C1 C2 122.73(17) . . ?
C1 C2 C7 123.60(15) . . ?
C3 C2 C1 116.69(15) . . ?
C3 C2 C7 119.58(14) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.80(17) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.61(19) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.32(17) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.83(17) . . ?
C5 C6 H6 120.6 . . ?
N1 C7 C2 110.81(13) . . ?
N1 C7 H7 107.6 . . ?
N1 C7 C8 108.68(12) . . ?
C2 C7 H7 107.6 . . ?
C8 C7 C2 114.17(13) . . ?
C8 C7 H7 107.6 . . ?
C9 C8 C7 125.09(15) . . ?
C9 C8 C11 107.02(14) . . ?
C11 C8 C7 127.89(15) . . ?
N2 C9 C8 108.43(15) . . ?
N2 C9 H9 125.8 . . ?
C8 C9 H9 125.8 . . ?
N2 C10 H10 125.7 . . ?
N2 C10 C11 108.68(16) . . ?
C11 C10 H10 125.7 . . ?
C8 C11 H11 126.6 . . ?
C10 C11 C8 106.87(16) . . ?
C10 C11 H11 126.6 . . ?
N2 C12 H12A 109.1 . . ?
N2 C12 H12B 109.1 . . ?
N2 C12 C13 112.30(16) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
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
S1 O1 1.5931(13) . ?
S1 O2 1.4197(13) . ?
S1 O3 1.4208(13) . ?
S1 N1 1.5994(14) . ?
O1 C1 1.416(2) . ?
N1 H1 0.8800 . ?
N1 C7 1.494(2) . ?
N2 C9 1.364(2) . ?
N2 C10 1.363(2) . ?
N2 C12 1.465(2) . ?
C1 C2 1.393(2) . ?
C1 C6 1.386(2) . ?
C2 C3 1.393(2) . ?
C2 C7 1.522(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(3) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.495(2) . ?
C8 C9 1.373(2) . ?
C8 C11 1.420(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.371(2) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.504(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
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
S1 O1 C1 C2 -24.7(2) . . . . ?
S1 O1 C1 C6 156.59(13) . . . . ?
S1 N1 C7 C2 45.54(16) . . . . ?
S1 N1 C7 C8 171.76(11) . . . . ?
O1 S1 N1 C7 -60.11(13) . . . . ?
O1 C1 C2 C3 -177.36(15) . . . . ?
O1 C1 C2 C7 6.8(2) . . . . ?
O1 C1 C6 C5 178.18(17) . . . . ?
O2 S1 O1 C1 -67.60(13) . . . . ?
O2 S1 N1 C7 54.61(14) . . . . ?
O3 S1 O1 C1 164.06(11) . . . . ?
O3 S1 N1 C7 -171.62(12) . . . . ?
N1 S1 O1 C1 48.01(13) . . . . ?
N1 C7 C8 C9 108.58(18) . . . . ?
N1 C7 C8 C11 -70.8(2) . . . . ?
N2 C10 C11 C8 0.6(2) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C1 C2 C7 N1 -17.0(2) . . . . ?
C1 C2 C7 C8 -140.12(16) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C2 C7 C8 C9 -127.16(17) . . . . ?
C2 C7 C8 C11 53.5(2) . . . . ?
C3 C2 C7 N1 167.28(15) . . . . ?
C3 C2 C7 C8 44.2(2) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C6 C1 C2 C3 1.3(3) . . . . ?
C6 C1 C2 C7 -174.53(16) . . . . ?
C7 C2 C3 C4 174.85(17) . . . . ?
C7 C8 C9 N2 179.99(15) . . . . ?
C7 C8 C11 C10 179.38(17) . . . . ?
C9 N2 C10 C11 -1.0(2) . . . . ?
C9 N2 C12 C13 -96.7(2) . . . . ?
C9 C8 C11 C10 -0.1(2) . . . . ?
C10 N2 C9 C8 1.0(2) . . . . ?
C10 N2 C12 C13 77.3(2) . . . . ?
C11 C8 C9 N2 -0.6(2) . . . . ?
C12 N2 C9 C8 175.83(16) . . . . ?
C12 N2 C10 C11 -175.83(17) . . . . ?
