#------------------------------------------------------------------------------
#$Date: 2023-11-06 09:01:48 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287320 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/99/1569937.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_1569937
loop_
_publ_author_name
'Zhang, Xiang-Xin'
'Zheng, Hao'
'Mei, Yong-Kang'
'Liu, Yan'
'Liu, Ying-Ying'
'Ji, Ding-Wei'
'Wan, Boshun'
'Chen, Qing-An'
_publ_section_title
;
 Photo-induced imino functionalizations of alkenes via
 intermolecular charge transfer.
;
_journal_issue                   40
_journal_name_full               'Chemical science'
_journal_page_first              11170
_journal_page_last               11179
_journal_paper_doi               10.1039/d3sc03667g
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C27 H21 N O2 S'
_chemical_formula_sum            'C27 H21 N O2 S'
_chemical_formula_weight         423.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2fh3wy
_audit_creation_date             2023-03-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-15 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.874(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2324(6)
_cell_length_b                   9.0288(4)
_cell_length_c                   19.0515(9)
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.21
_cell_measurement_theta_min      2.50
_cell_volume                     2259.77(18)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294.8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            52161
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.670
_diffrn_reflns_theta_min         2.500
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1250 before and 0.0578 after correction. The Ratio of minimum to maximum transmission is 0.9136. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.901
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0780P)²+0.6390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3524
_reflns_number_total             5226
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc03667g2.cif
_cod_data_source_block           zhl
_cod_depositor_comments
'Adding full bibliography for 1569937--1569940.cif.'
_cod_database_code               1569937
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C27(H27), C26(H26), C14(H14), C21(H21), C23(H23), C17(H17), C10(H10),
 C25(H25), C18(H18), C20(H20), C24(H24), C13(H13), C19(H19), C11(H11), C12(H12),
  C2(H2), C6(H6), C4(H4), C3(H3), C5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
S1 S 0.58073(3) 0.38662(5) 0.40411(2) 0.05303(16) Uani 1 1 d . . . . .
O1 O 0.64463(10) 0.38025(15) 0.34862(7) 0.0607(4) Uani 1 1 d . . . . .
O2 O 0.50658(11) 0.50355(17) 0.40262(8) 0.0734(4) Uani 1 1 d . . . . .
N1 N 0.81155(11) 0.30686(15) 0.45179(7) 0.0456(3) Uani 1 1 d . . . . .
C8 C 0.74900(13) 0.34651(17) 0.50270(9) 0.0433(4) Uani 1 1 d . . . . .
C16 C 0.84989(13) 0.56326(19) 0.42180(9) 0.0465(4) Uani 1 1 d . . . . .
C22 C 0.90558(13) 0.33619(19) 0.35507(9) 0.0444(4) Uani 1 1 d . . . . .
C15 C 0.85248(12) 0.39857(18) 0.41283(9) 0.0428(4) Uani 1 1 d . . . . .
C9 C 0.79229(12) 0.31773(19) 0.57711(9) 0.0473(4) Uani 1 1 d . . . . .
C7 C 0.65052(13) 0.38564(18) 0.48682(9) 0.0476(4) Uani 1 1 d . . . . .
H7 H 0.6165 0.4153 0.5244 0.057 Uiso 1 1 calc R . . . .
C27 C 0.87164(15) 0.2039(2) 0.32373(10) 0.0542(5) Uani 1 1 d . . . . .
H27 H 0.8143 0.1579 0.3375 0.065 Uiso 1 1 calc R . . . .
C1 C 0.51561(15) 0.2164(2) 0.40452(10) 0.0599(5) Uani 1 1 d . . . . .
C26 C 0.92221(17) 0.1399(2) 0.27232(11) 0.0635(5) Uani 1 1 d . . . . .
H26 H 0.8981 0.0521 0.2510 0.076 Uiso 1 1 calc R . . . .
C14 C 0.74993(15) 0.3791(2) 0.63380(10) 0.0607(5) Uani 1 1 d . . . . .
H14 H 0.6959 0.4452 0.6255 0.073 Uiso 1 1 calc R . . . .
C21 C 0.87962(15) 0.6267(2) 0.48685(11) 0.0575(5) Uani 1 1 d . . . . .
H21 H 0.9016 0.5670 0.5255 0.069 Uiso 1 1 calc R . . . .
C23 C 0.99042(16) 0.4035(2) 0.33305(10) 0.0602(5) Uani 1 1 d . . . . .
H23 H 1.0128 0.4942 0.3522 0.072 Uiso 1 1 calc R . . . .
C17 C 0.81777(16) 0.6537(2) 0.36506(11) 0.0617(5) Uani 1 1 d . . . . .
H17 H 0.7992 0.6125 0.3206 0.074 Uiso 1 1 calc R . . . .
C10 C 0.87428(15) 0.2221(2) 0.59093(11) 0.0630(5) Uani 1 1 d . . . . .
H10 H 0.9050 0.1823 0.5537 0.076 Uiso 1 1 calc R . . . .
C25 C 1.00748(18) 0.2048(3) 0.25257(12) 0.0724(6) Uani 1 1 d . . . . .
H25 H 1.0423 0.1602 0.2186 0.087 Uiso 1 1 calc R . . . .
C18 C 0.8131(2) 0.8055(2) 0.37418(15) 0.0798(7) Uani 1 1 d . . . . .
H18 H 0.7894 0.8657 0.3361 0.096 Uiso 1 1 calc R . . . .
C20 C 0.87691(19) 0.7792(2) 0.49481(13) 0.0752(6) Uani 1 1 d . . . . .
H20 H 0.8982 0.8213 0.5386 0.090 Uiso 1 1 calc R . . . .
C24 C 1.04175(19) 0.3363(3) 0.28287(12) 0.0762(6) Uani 1 1 d . . . . .
H24 H 1.1000 0.3803 0.2694 0.091 Uiso 1 1 calc R . . . .
C13 C 0.78761(18) 0.3426(3) 0.70224(12) 0.0791(7) Uani 1 1 d . . . . .
H13 H 0.7590 0.3844 0.7399 0.095 Uiso 1 1 calc R . . . .
C19 C 0.8434(2) 0.8679(2) 0.43903(15) 0.0816(7) Uani 1 1 d . . . . .
H19 H 0.8410 0.9701 0.4448 0.098 Uiso 1 1 calc R . . . .
C11 C 0.9104(2) 0.1857(3) 0.65979(14) 0.0856(7) Uani 1 1 d . . . . .
H11 H 0.9647 0.1203 0.6687 0.103 Uiso 1 1 calc R . . . .
C12 C 0.8670(2) 0.2451(3) 0.71505(14) 0.0906(8) Uani 1 1 d . . . . .
H12 H 0.8913 0.2193 0.7612 0.109 Uiso 1 1 calc R . . . .
C2 C 0.5668(2) 0.0893(3) 0.39144(14) 0.0860(7) Uani 1 1 d . . . . .
H2 H 0.6338 0.0944 0.3815 0.103 Uiso 1 1 calc R . . . .
C6 C 0.41741(19) 0.2107(3) 0.42024(14) 0.0916(8) Uani 1 1 d . . . . .
H6 H 0.3832 0.2964 0.4307 0.110 Uiso 1 1 calc R . . . .
C4 C 0.4212(4) -0.0522(5) 0.40641(17) 0.1268(15) Uani 1 1 d . . . . .
H4 H 0.3882 -0.1432 0.4063 0.152 Uiso 1 1 calc R . . . .
C3 C 0.5191(3) -0.0460(3) 0.39301(17) 0.1150(11) Uani 1 1 d . . . . .
H3 H 0.5540 -0.1325 0.3849 0.138 Uiso 1 1 calc R . . . .
C5 C 0.3705(3) 0.0735(5) 0.4200(2) 0.1286(13) Uani 1 1 d . . . . .
H5 H 0.3032 0.0674 0.4293 0.154 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
_geom_angle_publ_flag
O1 S1 O2 118.45(8) . . ?
O1 S1 C7 112.00(8) . . ?
O1 S1 C1 107.49(9) . . ?
O2 S1 C7 108.08(9) . . ?
O2 S1 C1 107.89(10) . . ?
C7 S1 C1 101.52(8) . . ?
C15 N1 C8 124.53(14) . . ?
N1 C8 C9 115.15(15) . . ?
C7 C8 N1 123.29(16) . . ?
C7 C8 C9 120.74(16) . . ?
C21 C16 C15 120.46(16) . . ?
C21 C16 C17 119.08(18) . . ?
C17 C16 C15 120.46(17) . . ?
C27 C22 C15 119.22(15) . . ?
C27 C22 C23 118.71(16) . . ?
C23 C22 C15 122.03(16) . . ?
N1 C15 C16 124.13(15) . . ?
N1 C15 C22 117.16(15) . . ?
C22 C15 C16 118.71(14) . . ?
C14 C9 C8 121.72(17) . . ?
C10 C9 C8 119.55(17) . . ?
C10 C9 C14 118.67(18) . . ?
S1 C7 H7 116.5 . . ?
C8 C7 S1 127.02(14) . . ?
C8 C7 H7 116.5 . . ?
C22 C27 H27 119.7 . . ?
C26 C27 C22 120.51(18) . . ?
C26 C27 H27 119.7 . . ?
C2 C1 S1 118.48(17) . . ?
C6 C1 S1 120.7(2) . . ?
C6 C1 C2 120.7(2) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 C27 120.28(19) . . ?
C25 C26 H26 119.9 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C16 C21 H21 119.9 . . ?
C16 C21 C20 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.11(19) . . ?
C24 C23 H23 119.9 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.1(2) . . ?
C18 C17 H17 120.0 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 119.9 . . ?
C26 C25 H25 120.1 . . ?
C26 C25 C24 119.88(19) . . ?
C24 C25 H25 120.1 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.8 . . ?
C21 C20 H20 119.7 . . ?
C19 C20 C21 120.6(2) . . ?
C19 C20 H20 119.7 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.5(2) . . ?
C25 C24 H24 119.8 . . ?
C14 C13 H13 119.8 . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.8 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.6(2) . . ?
C20 C19 H19 120.2 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 120.1 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.1(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C6 H6 121.0 . . ?
C1 C6 C5 118.0(3) . . ?
C5 C6 H6 121.0 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.5(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.5 . . ?
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 1.4318(14) . ?
S1 O2 1.4392(14) . ?
S1 C7 1.7284(19) . ?
S1 C1 1.762(2) . ?
N1 C8 1.395(2) . ?
N1 C15 1.275(2) . ?
C8 C9 1.487(2) . ?
C8 C7 1.349(2) . ?
C16 C15 1.498(2) . ?
C16 C21 1.379(3) . ?
C16 C17 1.381(3) . ?
C22 C15 1.486(2) . ?
C22 C27 1.386(2) . ?
C22 C23 1.385(2) . ?
C9 C14 1.390(3) . ?
C9 C10 1.387(3) . ?
C7 H7 0.9300 . ?
C27 H27 0.9300 . ?
C27 C26 1.377(3) . ?
C1 C2 1.371(3) . ?
C1 C6 1.369(3) . ?
C26 H26 0.9300 . ?
C26 C25 1.364(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.379(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.386(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.378(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.373(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(4) . ?
C20 H20 0.9300 . ?
C20 C19 1.362(3) . ?
C24 H24 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.370(4) . ?
C19 H19 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.368(4) . ?
C12 H12 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.377(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.385(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.351(5) . ?
C4 C5 1.359(5) . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
