#------------------------------------------------------------------------------
#$Date: 2022-11-21 11:39:49 +0200 (Mon, 21 Nov 2022) $
#$Revision: 279430 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/61/8106182.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_8106182
loop_
_publ_author_name
'Huang, Xie'
'Wang, Ping-an'
'He, Wei'
'Ye, Xiaoxia'
_publ_section_title
;
 Crystal structure of
 5-methyl-3,3-diphenyl-1-tosyl-1,2,3,4-tetrahydropyridine, C25H25NO2S
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              457
_journal_page_last               458
_journal_paper_doi               10.1515/ncrs-2017-0350
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C25 H25 N O2 S'
_chemical_formula_weight         403.52
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 95.117(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.371(4)
_cell_length_b                   11.397(4)
_cell_length_c                   9.777(4)
_cell_measurement_reflns_used    1836
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.08
_cell_measurement_theta_min      2.75
_cell_volume                     1040.0(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5068
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.9714
_exptl_absorpt_correction_T_min  0.9347
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.11(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0389P)²+0.1319P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0921
_reflns_number_gt                2874
_reflns_number_total             3373
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0350_suppl.cif
_cod_data_source_block           x
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               8106182
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.75726(9) 0.25438(6) 0.78180(7) 0.0423(2) Uani 1 1 d . . .
N1 N 0.7289(2) 0.2942(2) 0.6209(2) 0.0393(6) Uani 1 1 d . . .
O1 O 0.6424(2) 0.17697(18) 0.8069(2) 0.0542(6) Uani 1 1 d . . .
O2 O 0.9025(2) 0.2161(2) 0.8022(2) 0.0602(7) Uani 1 1 d . . .
C1 C 0.7110(4) 0.7004(3) 1.1058(4) 0.0701(11) Uani 1 1 d . . .
H1A H 0.8040 0.7226 1.1468 0.105 Uiso 1 1 calc R . .
H1B H 0.6470 0.6902 1.1763 0.105 Uiso 1 1 calc R . .
H1C H 0.6747 0.7608 1.0436 0.105 Uiso 1 1 calc R . .
C2 C 0.7223(3) 0.5872(3) 1.0285(3) 0.0449(8) Uani 1 1 d . . .
C3 C 0.6010(3) 0.5315(3) 0.9699(3) 0.0477(8) Uani 1 1 d . . .
H3 H 0.5115 0.5638 0.9803 0.057 Uiso 1 1 calc R . .
C4 C 0.6100(3) 0.4296(3) 0.8967(3) 0.0436(7) Uani 1 1 d . . .
H4 H 0.5273 0.3930 0.8582 0.052 Uiso 1 1 calc R . .
C5 C 0.7422(3) 0.3820(2) 0.8808(2) 0.0342(6) Uani 1 1 d . . .
C6 C 0.8644(3) 0.4348(3) 0.9405(3) 0.0444(8) Uani 1 1 d . . .
H6 H 0.9537 0.4014 0.9315 0.053 Uiso 1 1 calc R . .
C7 C 0.8540(3) 0.5371(3) 1.0135(3) 0.0494(8) Uani 1 1 d . . .
H7 H 0.9367 0.5729 1.0532 0.059 Uiso 1 1 calc R . .
C8 C 0.8287(3) 0.3717(3) 0.5678(3) 0.0444(8) Uani 1 1 d . . .
H8 H 0.9178 0.3816 0.6165 0.053 Uiso 1 1 calc R . .
C9 C 0.8003(3) 0.4302(3) 0.4526(3) 0.0411(7) Uani 1 1 d . . .
C10 C 0.6593(3) 0.4179(3) 0.3693(3) 0.0430(8) Uani 1 1 d . . .
H10A H 0.6748 0.4208 0.2725 0.052 Uiso 1 1 calc R . .
H10B H 0.5986 0.4837 0.3887 0.052 Uiso 1 1 calc R . .
C11 C 0.5819(3) 0.3033(3) 0.3987(2) 0.0351(6) Uani 1 1 d . . .
C12 C 0.5811(3) 0.3008(3) 0.5577(3) 0.0403(7) Uani 1 1 d . . .
H12A H 0.5353 0.3711 0.5887 0.048 Uiso 1 1 calc R . .
H12B H 0.5272 0.2334 0.5849 0.048 Uiso 1 1 calc R . .
C13 C 0.9056(4) 0.5146(4) 0.4000(3) 0.0661(10) Uani 1 1 d . . .
H13A H 0.9912 0.5160 0.4616 0.099 Uiso 1 1 calc R . .
H13B H 0.8642 0.5917 0.3940 0.099 Uiso 1 1 calc R . .
H13C H 0.9286 0.4901 0.3106 0.099 Uiso 1 1 calc R . .
C14 C 0.4247(3) 0.3014(3) 0.3381(3) 0.0370(6) Uani 1 1 d . . .
C15 C 0.3631(3) 0.3923(3) 0.2617(3) 0.0469(8) Uani 1 1 d . . .
H15 H 0.4182 0.4576 0.2441 0.056 Uiso 1 1 calc R . .
C16 C 0.2206(4) 0.3886(3) 0.2103(4) 0.0635(10) Uani 1 1 d . . .
H16 H 0.1813 0.4514 0.1592 0.076 Uiso 1 1 calc R . .
C17 C 0.1372(4) 0.2940(3) 0.2338(4) 0.0625(10) Uani 1 1 d . . .
H17 H 0.0417 0.2914 0.1988 0.075 Uiso 1 1 calc R . .
C18 C 0.1975(4) 0.2028(3) 0.3102(4) 0.0586(9) Uani 1 1 d . . .
H18 H 0.1420 0.1379 0.3283 0.070 Uiso 1 1 calc R . .
C19 C 0.3381(3) 0.2063(3) 0.3598(3) 0.0494(8) Uani 1 1 d . . .
H19 H 0.3769 0.1427 0.4098 0.059 Uiso 1 1 calc R . .
C20 C 0.6597(3) 0.1964(3) 0.3463(3) 0.0337(6) Uani 1 1 d . . .
C21 C 0.7077(3) 0.1977(3) 0.2154(3) 0.0503(8) Uani 1 1 d . . .
H21 H 0.6947 0.2649 0.1618 0.060 Uiso 1 1 calc R . .
C22 C 0.7735(4) 0.1021(4) 0.1641(3) 0.0612(10) Uani 1 1 d . . .
H22 H 0.8063 0.1058 0.0772 0.073 Uiso 1 1 calc R . .
C23 C 0.7913(4) 0.0020(3) 0.2387(4) 0.0615(10) Uani 1 1 d . . .
H23 H 0.8356 -0.0626 0.2027 0.074 Uiso 1 1 calc R . .
C24 C 0.7435(3) -0.0037(3) 0.3687(4) 0.0554(9) Uani 1 1 d . . .
H24 H 0.7544 -0.0723 0.4202 0.066 Uiso 1 1 calc R . .
C25 C 0.6796(3) 0.0937(3) 0.4204(3) 0.0446(7) Uani 1 1 d . . .
H25 H 0.6489 0.0901 0.5082 0.053 Uiso 1 1 calc R . .
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
O2 S1 O1 120.73(15) . .
O2 S1 N1 106.86(12) . .
O1 S1 N1 106.02(12) . .
O2 S1 C5 107.34(14) . .
O1 S1 C5 108.49(13) . .
N1 S1 C5 106.63(12) . .
C8 N1 C12 116.3(2) . .
C8 N1 S1 117.95(19) . .
C12 N1 S1 119.01(17) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C3 C2 C7 118.4(3) . .
C3 C2 C1 120.7(3) . .
C7 C2 C1 120.9(3) . .
C4 C3 C2 121.3(3) . .
C4 C3 H3 119.3 . .
C2 C3 H3 119.3 . .
C5 C4 C3 119.5(3) . .
C5 C4 H4 120.3 . .
C3 C4 H4 120.3 . .
C6 C5 C4 120.3(3) . .
C6 C5 S1 119.3(2) . .
C4 C5 S1 120.4(2) . .
C5 C6 C7 119.7(3) . .
C5 C6 H6 120.2 . .
C7 C6 H6 120.2 . .
C2 C7 C6 120.8(3) . .
C2 C7 H7 119.6 . .
C6 C7 H7 119.6 . .
C9 C8 N1 122.6(3) . .
C9 C8 H8 118.7 . .
N1 C8 H8 118.7 . .
C8 C9 C10 121.4(3) . .
C8 C9 C13 122.0(3) . .
C10 C9 C13 116.6(3) . .
C9 C10 C11 112.8(2) . .
C9 C10 H10A 109.0 . .
C11 C10 H10A 109.0 . .
C9 C10 H10B 109.0 . .
C11 C10 H10B 109.0 . .
H10A C10 H10B 107.8 . .
C20 C11 C10 111.6(2) . .
C20 C11 C14 109.1(2) . .
C10 C11 C14 113.1(2) . .
C20 C11 C12 111.4(2) . .
C10 C11 C12 104.4(2) . .
C14 C11 C12 107.1(2) . .
N1 C12 C11 109.4(2) . .
N1 C12 H12A 109.8 . .
C11 C12 H12A 109.8 . .
N1 C12 H12B 109.8 . .
C11 C12 H12B 109.8 . .
H12A C12 H12B 108.2 . .
C9 C13 H13A 109.5 . .
C9 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C9 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C15 C14 C19 116.8(3) . .
C15 C14 C11 122.7(3) . .
C19 C14 C11 120.5(3) . .
C14 C15 C16 121.2(3) . .
C14 C15 H15 119.4 . .
C16 C15 H15 119.4 . .
C17 C16 C15 120.8(3) . .
C17 C16 H16 119.6 . .
C15 C16 H16 119.6 . .
C16 C17 C18 118.5(3) . .
C16 C17 H17 120.8 . .
C18 C17 H17 120.8 . .
C19 C18 C17 120.6(3) . .
C19 C18 H18 119.7 . .
C17 C18 H18 119.7 . .
C18 C19 C14 122.0(3) . .
C18 C19 H19 119.0 . .
C14 C19 H19 119.0 . .
C25 C20 C21 116.8(3) . .
C25 C20 C11 123.1(2) . .
C21 C20 C11 120.0(2) . .
C22 C21 C20 121.4(3) . .
C22 C21 H21 119.3 . .
C20 C21 H21 119.3 . .
C23 C22 C21 120.7(3) . .
C23 C22 H22 119.7 . .
C21 C22 H22 119.7 . .
C22 C23 C24 119.9(3) . .
C22 C23 H23 120.0 . .
C24 C23 H23 120.0 . .
C25 C24 C23 119.0(3) . .
C25 C24 H24 120.5 . .
C23 C24 H24 120.5 . .
C24 C25 C20 122.2(3) . .
C24 C25 H25 118.9 . .
C20 C25 H25 118.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.426(2) .
S1 O1 1.430(2) .
S1 N1 1.636(2) .
S1 C5 1.760(3) .
N1 C8 1.418(3) .
N1 C12 1.468(3) .
C1 C2 1.504(4) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C3 1.381(4) .
C2 C7 1.379(4) .
C3 C4 1.371(4) .
C3 H3 0.9300 .
C4 C5 1.374(4) .
C4 H4 0.9300 .
C5 C6 1.376(4) .
C6 C7 1.375(4) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 C9 1.316(4) .
C8 H8 0.9300 .
C9 C10 1.496(4) .
C9 C13 1.502(4) .
C10 C11 1.533(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C20 1.531(4) .
C11 C14 1.539(4) .
C11 C12 1.556(3) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 C15 1.374(4) .
C14 C19 1.382(4) .
C15 C16 1.385(4) .
C15 H15 0.9300 .
C16 C17 1.362(5) .
C16 H16 0.9300 .
C17 C18 1.373(5) .
C17 H17 0.9300 .
C18 C19 1.363(5) .
C18 H18 0.9300 .
C19 H19 0.9300 .
C20 C25 1.380(4) .
C20 C21 1.394(4) .
C21 C22 1.369(5) .
C21 H21 0.9300 .
C22 C23 1.356(5) .
C22 H22 0.9300 .
C23 C24 1.386(5) .
C23 H23 0.9300 .
C24 C25 1.380(4) .
C24 H24 0.9300 .
C25 H25 0.9300 .
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
O2 S1 N1 C8 -49.7(2) . . . .
O1 S1 N1 C8 -179.7(2) . . . .
C5 S1 N1 C8 64.8(2) . . . .
O2 S1 N1 C12 160.1(2) . . . .
O1 S1 N1 C12 30.2(2) . . . .
C5 S1 N1 C12 -85.3(2) . . . .
C7 C2 C3 C4 -0.9(4) . . . .
C1 C2 C3 C4 178.6(3) . . . .
C2 C3 C4 C5 -0.2(5) . . . .
C3 C4 C5 C6 1.4(4) . . . .
C3 C4 C5 S1 -177.5(2) . . . .
O2 S1 C5 C6 10.1(3) . . . .
O1 S1 C5 C6 142.1(2) . . . .
N1 S1 C5 C6 -104.1(2) . . . .
O2 S1 C5 C4 -170.9(2) . . . .
O1 S1 C5 C4 -39.0(3) . . . .
N1 S1 C5 C4 74.8(2) . . . .
C4 C5 C6 C7 -1.5(4) . . . .
S1 C5 C6 C7 177.4(2) . . . .
C3 C2 C7 C6 0.8(4) . . . .
C1 C2 C7 C6 -178.7(3) . . . .
C5 C6 C7 C2 0.4(4) . . . .
C12 N1 C8 C9 -12.8(4) . . . .
S1 N1 C8 C9 -163.8(2) . . . .
N1 C8 C9 C10 -0.2(4) . . . .
N1 C8 C9 C13 178.2(3) . . . .
C8 C9 C10 C11 -21.9(4) . . . .
C13 C9 C10 C11 159.6(3) . . . .
C9 C10 C11 C20 -68.8(3) . . . .
C9 C10 C11 C14 167.6(2) . . . .
C9 C10 C11 C12 51.6(3) . . . .
C8 N1 C12 C11 46.1(3) . . . .
S1 N1 C12 C11 -163.31(19) . . . .
C20 C11 C12 N1 56.8(3) . . . .
C10 C11 C12 N1 -63.8(3) . . . .
C14 C11 C12 N1 176.1(2) . . . .
C20 C11 C14 C15 -122.8(3) . . . .
C10 C11 C14 C15 2.1(4) . . . .
C12 C11 C14 C15 116.5(3) . . . .
C20 C11 C14 C19 57.6(3) . . . .
C10 C11 C14 C19 -177.5(2) . . . .
C12 C11 C14 C19 -63.1(3) . . . .
C19 C14 C15 C16 0.6(4) . . . .
C11 C14 C15 C16 -179.0(3) . . . .
C14 C15 C16 C17 -0.3(5) . . . .
C15 C16 C17 C18 0.4(5) . . . .
C16 C17 C18 C19 -0.8(5) . . . .
C17 C18 C19 C14 1.2(5) . . . .
C15 C14 C19 C18 -1.0(4) . . . .
C11 C14 C19 C18 178.5(3) . . . .
C10 C11 C20 C25 137.6(3) . . . .
C14 C11 C20 C25 -96.6(3) . . . .
C12 C11 C20 C25 21.4(4) . . . .
C10 C11 C20 C21 -45.7(3) . . . .
C14 C11 C20 C21 80.1(3) . . . .
C12 C11 C20 C21 -161.9(3) . . . .
C25 C20 C21 C22 -1.1(4) . . . .
C11 C20 C21 C22 -177.9(3) . . . .
C20 C21 C22 C23 1.4(5) . . . .
C21 C22 C23 C24 -0.5(5) . . . .
C22 C23 C24 C25 -0.7(5) . . . .
C23 C24 C25 C20 1.0(5) . . . .
C21 C20 C25 C24 -0.1(4) . . . .
C11 C20 C25 C24 176.7(3) . . . .
