#------------------------------------------------------------------------------
#$Date: 2022-05-05 23:37:41 +0300 (Thu, 05 May 2022) $
#$Revision: 274991 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/44/7244482.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_7244482
loop_
_publ_author_name
'He, Jin-Yu'
'Qian, Wei-Feng'
'Wang, Yan-Zhao'
'Yao, Chaochao'
'Wang, Nana'
'Liu, Huilin'
'Zhong, Bing'
'Zhu, Cuiju'
'Xu, Hao'
_publ_section_title
;
 Sustainable electrochemical dehydrogenative C(sp3)--H mono/di-alkylations
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              2483
_journal_page_last               2491
_journal_paper_doi               10.1039/D1GC04479F
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C20 H19 N O2 S'
_chemical_formula_sum            'C20 H19 N O2 S'
_chemical_formula_weight         337.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-21
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2021-10-27 deposited with the CCDC.	2022-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.602(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.979(4)
_cell_length_b                   9.2286(12)
_cell_length_c                   14.3392(19)
_cell_measurement_reflns_used    8268
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      31.60
_cell_measurement_theta_min      2.34
_cell_volume                     3484.1(8)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18183
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.030
_diffrn_reflns_theta_min         1.547
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         5678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0692P)²+1.8249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1375
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4333
_reflns_number_total             5678
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1gc04479f3.cif
_cod_data_source_block           mo_210618a_0m
_cod_depositor_comments
'Adding full bibliography for 7244482--7244484.cif.'
_cod_database_code               7244482
_shelx_shelxl_version_number     2014/7
_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   0.962
_shelx_estimated_absorpt_t_min   0.943
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H) groups 
2.a Ternary CH refined with riding coordinates: 
 C10(H10) 
2.b Secondary CH2 refined with riding coordinates: 
 C9(H9A,H9B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C2(H2), C6(H6), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), 
 C20(H20) 
2.d Idealised Me refined as rotating group: 
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C) 
2.e Idealised tetrahedral OH refined as rotating group: 
 O1(H1) 
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C1 C 0.81479(4) 0.22707(14) 0.39385(8) 0.0328(2) Uani 1 1 d . . . . .
C2 C 0.80573(5) 0.35731(15) 0.43509(9) 0.0368(3) Uani 1 1 d . . . . .
H2 H 0.8326 0.4047 0.4750 0.044 Uiso 1 1 calc R . . . .
C3 C 0.75759(5) 0.41944(14) 0.41869(9) 0.0360(3) Uani 1 1 d . . . . .
C4 C 0.71759(5) 0.34655(14) 0.35977(9) 0.0342(2) Uani 1 1 d . . . . .
C5 C 0.72472(5) 0.21372(15) 0.31825(10) 0.0385(3) Uani 1 1 d . . . . .
C6 C 0.77381(5) 0.15699(15) 0.33560(10) 0.0391(3) Uani 1 1 d . . . . .
H6 H 0.7793 0.0695 0.3073 0.047 Uiso 1 1 calc R . . . .
C7 C 0.74888(7) 0.56236(18) 0.46273(14) 0.0576(4) Uani 1 1 d . . . . .
H7A H 0.7793 0.5915 0.5069 0.086 Uiso 1 1 calc GR . . . .
H7B H 0.7218 0.5527 0.4960 0.086 Uiso 1 1 calc GR . . . .
H7C H 0.7400 0.6341 0.4135 0.086 Uiso 1 1 calc GR . . . .
C8 C 0.68082(6) 0.1316(2) 0.25879(16) 0.0675(6) Uani 1 1 d . . . . .
H8A H 0.6552 0.1175 0.2949 0.101 Uiso 1 1 calc GR . . . .
H8B H 0.6924 0.0391 0.2415 0.101 Uiso 1 1 calc GR . . . .
H8C H 0.6669 0.1857 0.2019 0.101 Uiso 1 1 calc GR . . . .
C9 C 0.86716(5) 0.15998(16) 0.41248(9) 0.0363(3) Uani 1 1 d . . . . .
H9A H 0.8656 0.0639 0.4391 0.044 Uiso 1 1 calc R . . . .
H9B H 0.8900 0.2179 0.4596 0.044 Uiso 1 1 calc R . . . .
C10 C 0.88869(4) 0.14859(13) 0.32158(8) 0.0294(2) Uani 1 1 d . . . . .
H10 H 0.8613 0.1151 0.2694 0.035 Uiso 1 1 calc R . . . .
C11 C 0.90744(5) 0.29368(13) 0.29202(9) 0.0324(2) Uani 1 1 d . . . . .
C12 C 0.90747(5) 0.31184(13) 0.19056(9) 0.0332(2) Uani 1 1 d . . . . .
C13 C 0.88506(5) 0.22811(16) 0.11368(9) 0.0406(3) Uani 1 1 d . . . . .
H13 H 0.8662 0.1451 0.1185 0.049 Uiso 1 1 calc R . . . .
C14 C 0.89382(7) 0.2821(2) 0.02656(11) 0.0544(4) Uani 1 1 d . . . . .
H14 H 0.8812 0.2390 -0.0325 0.065 Uiso 1 1 calc R . . . .
C15 C 0.92256(7) 0.4036(2) 0.03871(12) 0.0573(4) Uani 1 1 d . . . . .
H15 H 0.9320 0.4533 -0.0111 0.069 Uiso 1 1 calc R . . . .
C16 C 0.93118(4) 0.03720(12) 0.33493(8) 0.0292(2) Uani 1 1 d . . . . .
C17 C 0.98170(5) 0.07217(15) 0.37089(10) 0.0389(3) Uani 1 1 d . . . . .
H17 H 0.9915 0.1682 0.3830 0.047 Uiso 1 1 calc R . . . .
C18 C 1.01738(5) -0.03771(18) 0.38847(11) 0.0470(3) Uani 1 1 d . . . . .
H18 H 1.0515 -0.0165 0.4124 0.056 Uiso 1 1 calc R . . . .
C19 C 1.00183(6) -0.17820(17) 0.37021(11) 0.0480(3) Uani 1 1 d . . . . .
H19 H 1.0250 -0.2541 0.3831 0.058 Uiso 1 1 calc R . . . .
C20 C 0.95123(6) -0.20460(15) 0.33246(11) 0.0451(3) Uani 1 1 d . . . . .
H20 H 0.9410 -0.3000 0.3191 0.054 Uiso 1 1 calc R . . . .
N1 N 0.91596(4) -0.10013(12) 0.31400(8) 0.0373(2) Uani 1 1 d . . . . .
O1 O 0.67029(4) 0.40982(12) 0.34695(8) 0.0480(3) Uani 1 1 d . . . . .
H1 H 0.6516 0.3761 0.2990 0.072 Uiso 1 1 calc GR . . . .
O2 O 0.92363(5) 0.38846(12) 0.34964(8) 0.0506(3) Uani 1 1 d . . . . .
S1 S 0.93946(2) 0.45528(4) 0.15501(3) 0.05391(13) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.96(11) . . ?
C2 C1 C9 121.68(12) . . ?
C6 C1 C9 120.35(11) . . ?
C1 C2 H2 119.0 . . ?
C1 C2 C3 122.04(12) . . ?
C3 C2 H2 119.0 . . ?
C2 C3 C7 121.08(12) . . ?
C4 C3 C2 118.38(12) . . ?
C4 C3 C7 120.54(12) . . ?
C3 C4 C5 121.57(11) . . ?
O1 C4 C3 116.70(11) . . ?
O1 C4 C5 121.70(11) . . ?
C4 C5 C6 117.90(12) . . ?
C4 C5 C8 121.34(12) . . ?
C6 C5 C8 120.74(13) . . ?
C1 C6 C5 122.12(12) . . ?
C1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 C9 H9A 109.0 . . ?
C1 C9 H9B 109.0 . . ?
C1 C9 C10 112.86(10) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C9 C10 H10 107.8 . . ?
C11 C10 C9 112.60(10) . . ?
C11 C10 H10 107.8 . . ?
C16 C10 C9 110.63(9) . . ?
C16 C10 H10 107.8 . . ?
C16 C10 C11 110.02(9) . . ?
C12 C11 C10 116.68(10) . . ?
O2 C11 C10 122.31(11) . . ?
O2 C11 C12 120.94(12) . . ?
C11 C12 S1 119.49(9) . . ?
C13 C12 C11 129.59(12) . . ?
C13 C12 S1 110.92(10) . . ?
C12 C13 H13 123.8 . . ?
C12 C13 C14 112.48(13) . . ?
C14 C13 H13 123.8 . . ?
C13 C14 H14 123.8 . . ?
C15 C14 C13 112.36(15) . . ?
C15 C14 H14 123.8 . . ?
C14 C15 H15 123.7 . . ?
C14 C15 S1 112.52(12) . . ?
S1 C15 H15 123.7 . . ?
C17 C16 C10 122.86(11) . . ?
N1 C16 C10 115.07(10) . . ?
N1 C16 C17 121.98(11) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 C16 119.08(13) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.14(13) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 H19 120.7 . . ?
C18 C19 C20 118.61(13) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 H20 118.3 . . ?
N1 C20 C19 123.45(14) . . ?
N1 C20 H20 118.3 . . ?
C20 N1 C16 117.69(11) . . ?
C4 O1 H1 109.5 . . ?
C15 S1 C12 91.73(7) . . ?
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
C1 C2 1.3845(18) . ?
C1 C6 1.3911(18) . ?
C1 C9 1.5121(16) . ?
C2 H2 0.9300 . ?
C2 C3 1.3919(17) . ?
C3 C4 1.3905(18) . ?
C3 C7 1.5029(19) . ?
C4 C5 1.3943(18) . ?
C4 O1 1.3786(14) . ?
C5 C6 1.3952(17) . ?
C5 C8 1.505(2) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.5421(16) . ?
C10 H10 0.9800 . ?
C10 C11 1.5238(17) . ?
C10 C16 1.5203(15) . ?
C11 C12 1.4646(17) . ?
C11 O2 1.2170(15) . ?
C12 C13 1.3736(18) . ?
C12 S1 1.7174(13) . ?
C13 H13 0.9300 . ?
C13 C14 1.412(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.352(3) . ?
C15 H15 0.9300 . ?
C15 S1 1.6985(19) . ?
C16 C17 1.3860(17) . ?
C16 N1 1.3458(16) . ?
C17 H17 0.9300 . ?
C17 C18 1.3830(19) . ?
C18 H18 0.9300 . ?
C18 C19 1.370(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(2) . ?
C20 H20 0.9300 . ?
C20 N1 1.3398(17) . ?
O1 H1 0.8200 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.82 2.17 2.8994(16) 148.3 4_655
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
C1 C2 C3 C4 0.7(2) . . . . ?
C1 C2 C3 C7 -178.80(14) . . . . ?
C1 C9 C10 C11 76.12(13) . . . . ?
C1 C9 C10 C16 -160.31(11) . . . . ?
C2 C1 C6 C5 -0.1(2) . . . . ?
C2 C1 C9 C10 -116.53(13) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C2 C3 C4 O1 178.59(12) . . . . ?
C3 C4 C5 C6 -1.6(2) . . . . ?
C3 C4 C5 C8 176.73(16) . . . . ?
C4 C5 C6 C1 1.4(2) . . . . ?
C6 C1 C2 C3 -0.94(19) . . . . ?
C6 C1 C9 C10 64.77(16) . . . . ?
C7 C3 C4 C5 -179.88(15) . . . . ?
C7 C3 C4 O1 -1.9(2) . . . . ?
C8 C5 C6 C1 -176.98(16) . . . . ?
C9 C1 C2 C3 -179.67(12) . . . . ?
C9 C1 C6 C5 178.62(12) . . . . ?
C9 C10 C11 C12 -153.97(10) . . . . ?
C9 C10 C11 O2 28.98(16) . . . . ?
C9 C10 C16 C17 -89.98(14) . . . . ?
C9 C10 C16 N1 86.66(13) . . . . ?
C10 C11 C12 C13 12.65(19) . . . . ?
C10 C11 C12 S1 -166.95(8) . . . . ?
C10 C16 C17 C18 174.47(12) . . . . ?
C10 C16 N1 C20 -174.20(11) . . . . ?
C11 C10 C16 C17 35.06(15) . . . . ?
C11 C10 C16 N1 -148.30(10) . . . . ?
C11 C12 C13 C14 179.90(13) . . . . ?
C11 C12 S1 C15 -179.99(11) . . . . ?
C12 C13 C14 C15 0.4(2) . . . . ?
C13 C12 S1 C15 0.34(11) . . . . ?
C13 C14 C15 S1 -0.1(2) . . . . ?
C14 C15 S1 C12 -0.12(15) . . . . ?
C16 C10 C11 C12 82.13(12) . . . . ?
C16 C10 C11 O2 -94.93(14) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C17 C16 N1 C20 2.47(19) . . . . ?
C17 C18 C19 C20 1.7(2) . . . . ?
C18 C19 C20 N1 -1.2(2) . . . . ?
C19 C20 N1 C16 -0.9(2) . . . . ?
N1 C16 C17 C18 -1.9(2) . . . . ?
O1 C4 C5 C6 -179.49(13) . . . . ?
O1 C4 C5 C8 -1.1(2) . . . . ?
O2 C11 C12 C13 -170.24(14) . . . . ?
O2 C11 C12 S1 10.15(17) . . . . ?
S1 C12 C13 C14 -0.46(16) . . . . ?
