#------------------------------------------------------------------------------
#$Date: 2021-09-30 04:45:36 +0300 (Thu, 30 Sep 2021) $
#$Revision: 269396 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/36/7243644.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_7243644
loop_
_publ_author_name
'Luo, Xiai'
'Zhao, Yu'
'Tao, Susu'
'Yang, Zhong-Tao'
'Luo, Hui'
'Yang, Weiguang'
_publ_section_title
;
 A simple and efficient copper-catalyzed three-component reaction to
 synthesize (Z)-1,2-dihydro-2-iminoquinolines
;
_journal_issue                   50
_journal_name_full               'RSC Advances'
_journal_page_first              31152
_journal_page_last               31158
_journal_paper_doi               10.1039/D1RA06330H
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C19 H18 N2 O3 S'
_chemical_formula_sum            'C19 H18 N2 O3 S'
_chemical_formula_weight         354.41
_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
_audit_creation_date             2021-05-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-06-25 deposited with the CCDC.	2021-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.953(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.929(18)
_cell_length_b                   10.763(18)
_cell_length_c                   15.62(3)
_cell_measurement_reflns_used    3022
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.959
_cell_measurement_theta_min      2.346
_cell_volume                     1727(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.965
_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  0.0659
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9388
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.127
_diffrn_reflns_theta_min         1.982
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0904 before and 0.0559 after correction.
The Ratio of minimum to maximum transmission is 0.7064.
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    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.1629
_refine_ls_R_factor_gt           0.0968
_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)+6.0103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1674
_refine_ls_wR_factor_ref         0.1968
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1990
_reflns_number_total             3319
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra06330h2.cif
_cod_data_source_block           mo_052301_0m_a
_cod_original_cell_volume        1726(5)
_cod_database_code               7243644
_shelx_shelxl_version_number     2016/6
_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   0.984
_shelx_estimated_absorpt_t_min   0.975
_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 Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C5(H5), C19(H19), C15(H15), C18(H18), C1(H1A), C6(H6),
 C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.70821(14) 0.58161(13) 0.08840(9) 0.0428(4) Uani 1 1 d . . . . .
O2 O 0.6624(4) 0.4667(3) 0.1136(2) 0.0477(9) Uani 1 1 d . . . . .
O3 O 0.7489(4) 0.5781(4) 0.0101(2) 0.0546(10) Uani 1 1 d . . . . .
N2 N 0.8204(4) 0.6446(4) 0.1703(3) 0.0389(10) Uani 1 1 d . . . . .
N1 N 0.7719(4) 0.5428(4) 0.2900(3) 0.0403(10) Uani 1 1 d . . . . .
H1 H 0.724819 0.488983 0.252427 0.048 Uiso 1 1 calc R U . . .
O1 O 0.9555(5) 0.9079(4) 0.2713(3) 0.0754(14) Uani 1 1 d . . . . .
C10 C 0.8328(5) 0.6293(4) 0.2571(3) 0.0349(11) Uani 1 1 d . . . . .
C9 C 0.9198(5) 0.7105(4) 0.3229(3) 0.0368(12) Uani 1 1 d . . . . .
C4 C 0.8598(5) 0.6168(4) 0.4433(3) 0.0393(12) Uani 1 1 d . . . . .
C14 C 0.5312(5) 0.7055(5) 0.1429(3) 0.0444(13) Uani 1 1 d . . . . .
C3 C 0.7797(5) 0.5344(5) 0.3802(3) 0.0377(12) Uani 1 1 d . . . . .
C7 C 0.9311(5) 0.7084(5) 0.4122(3) 0.0399(12) Uani 1 1 d . . . . .
C2 C 0.7096(6) 0.4448(5) 0.4057(4) 0.0544(16) Uani 1 1 d . . . . .
H2 H 0.657497 0.389647 0.362811 0.065 Uiso 1 1 calc R U . . .
C5 C 0.8639(6) 0.6074(5) 0.5339(4) 0.0515(15) Uani 1 1 d . . . . .
H5 H 0.914452 0.662897 0.577252 0.062 Uiso 1 1 calc R U . . .
C19 C 0.4318(6) 0.6329(5) 0.1504(4) 0.0528(15) Uani 1 1 d . . . . .
H19 H 0.388925 0.578051 0.103807 0.063 Uiso 1 1 calc R U . . .
C11 C 0.9890(6) 0.8028(5) 0.2831(4) 0.0483(14) Uani 1 1 d . . . . .
C15 C 0.5912(6) 0.7884(5) 0.2123(4) 0.0540(15) Uani 1 1 d . . . . .
H15 H 0.656487 0.840314 0.207289 0.065 Uiso 1 1 calc R U . . .
C13 C 0.5769(5) 0.6899(5) 0.0631(3) 0.0467(14) Uani 1 1 d . . . . .
H13A H 0.605062 0.769632 0.047532 0.056 Uiso 1 1 calc R U . . .
H13B H 0.505209 0.660810 0.010808 0.056 Uiso 1 1 calc R U . . .
C8 C 1.0181(6) 0.7981(6) 0.4792(4) 0.0581(16) Uani 1 1 d . . . . .
H8A H 1.061232 0.850530 0.448679 0.087 Uiso 1 1 calc R U . . .
H8B H 1.081821 0.752836 0.526819 0.087 Uiso 1 1 calc R U . . .
H8C H 0.966860 0.848279 0.505021 0.087 Uiso 1 1 calc R U . . .
C18 C 0.3950(7) 0.6405(6) 0.2267(5) 0.0692(19) Uani 1 1 d . . . . .
H18 H 0.327621 0.591106 0.231101 0.083 Uiso 1 1 calc R U . . .
C1 C 0.7168(7) 0.4372(6) 0.4952(4) 0.0649(18) Uani 1 1 d . . . . .
H1A H 0.668984 0.377067 0.512738 0.078 Uiso 1 1 calc R U . . .
C6 C 0.7947(7) 0.5183(6) 0.5590(4) 0.0621(17) Uani 1 1 d . . . . .
H6 H 0.799884 0.512008 0.619539 0.075 Uiso 1 1 calc R U . . .
C16 C 0.5553(7) 0.7950(6) 0.2892(4) 0.0659(19) Uani 1 1 d . . . . .
H16 H 0.597637 0.849780 0.335912 0.079 Uiso 1 1 calc R U . . .
C17 C 0.4583(8) 0.7214(6) 0.2962(4) 0.071(2) Uani 1 1 d . . . . .
H17 H 0.434504 0.725568 0.347878 0.085 Uiso 1 1 calc R U . . .
C12 C 1.1032(6) 0.7526(7) 0.2629(4) 0.0706(19) Uani 1 1 d . . . . .
H12A H 1.121468 0.804717 0.218907 0.106 Uiso 1 1 calc R U . . .
H12B H 1.084182 0.669886 0.239000 0.106 Uiso 1 1 calc R U . . .
H12C H 1.177537 0.750679 0.317921 0.106 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 0.0033 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
O2 S1 N2 113.1(2) . . ?
O2 S1 C13 107.0(3) . . ?
O3 S1 O2 116.6(2) . . ?
O3 S1 N2 108.6(3) . . ?
O3 S1 C13 106.7(3) . . ?
N2 S1 C13 103.9(3) . . ?
C10 N2 S1 123.4(4) . . ?
C10 N1 H1 117.7 . . ?
C10 N1 C3 124.6(4) . . ?
C3 N1 H1 117.7 . . ?
N2 C10 N1 125.9(4) . . ?
N2 C10 C9 117.9(4) . . ?
N1 C10 C9 116.2(4) . . ?
C10 C9 C11 114.2(4) . . ?
C7 C9 C10 122.1(5) . . ?
C7 C9 C11 123.6(5) . . ?
C3 C4 C7 118.7(4) . . ?
C3 C4 C5 117.6(5) . . ?
C5 C4 C7 123.7(5) . . ?
C19 C14 C15 118.5(5) . . ?
C19 C14 C13 120.2(5) . . ?
C15 C14 C13 121.2(5) . . ?
N1 C3 C4 118.9(4) . . ?
C2 C3 N1 119.7(5) . . ?
C2 C3 C4 121.4(5) . . ?
C9 C7 C4 119.2(5) . . ?
C9 C7 C8 121.3(5) . . ?
C4 C7 C8 119.5(5) . . ?
C3 C2 H2 120.2 . . ?
C3 C2 C1 119.5(5) . . ?
C1 C2 H2 120.2 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(5) . . ?
C6 C5 H5 119.6 . . ?
C14 C19 H19 119.7 . . ?
C14 C19 C18 120.6(6) . . ?
C18 C19 H19 119.7 . . ?
O1 C11 C9 121.5(6) . . ?
O1 C11 C12 123.4(6) . . ?
C12 C11 C9 115.0(5) . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.8(6) . . ?
C16 C15 H15 119.6 . . ?
S1 C13 H13A 109.4 . . ?
S1 C13 H13B 109.4 . . ?
C14 C13 S1 111.0(4) . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 120.0(6) . . ?
C17 C18 H18 120.0 . . ?
C2 C1 H1A 119.9 . . ?
C2 C1 C6 120.3(6) . . ?
C6 C1 H1A 119.9 . . ?
C5 C6 C1 120.4(5) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0(6) . . ?
C17 C16 H16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 120.0(6) . . ?
C16 C17 H17 120.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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 O2 1.438(4) . ?
S1 O3 1.437(4) . ?
S1 N2 1.590(4) . ?
S1 C13 1.786(6) . ?
N2 C10 1.325(6) . ?
N1 H1 0.8600 . ?
N1 C10 1.343(6) . ?
N1 C3 1.384(6) . ?
O1 C11 1.184(7) . ?
C10 C9 1.435(7) . ?
C9 C7 1.356(7) . ?
C9 C11 1.506(7) . ?
C4 C3 1.391(7) . ?
C4 C7 1.440(7) . ?
C4 C5 1.404(7) . ?
C14 C19 1.375(8) . ?
C14 C15 1.384(7) . ?
C14 C13 1.503(7) . ?
C3 C2 1.373(7) . ?
C7 C8 1.500(7) . ?
C2 H2 0.9300 . ?
C2 C1 1.374(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.360(8) . ?
C19 H19 0.9300 . ?
C19 C18 1.383(8) . ?
C11 C12 1.489(9) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C18 H18 0.9300 . ?
C18 C17 1.379(9) . ?
C1 H1A 0.9300 . ?
C1 C6 1.379(8) . ?
C6 H6 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.357(9) . ?
C17 H17 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
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 N2 C10 N1 13.7(7) . . . . ?
S1 N2 C10 C9 -167.1(4) . . . . ?
O2 S1 N2 C10 -27.9(5) . . . . ?
O2 S1 C13 C14 57.4(4) . . . . ?
O3 S1 N2 C10 -158.9(4) . . . . ?
O3 S1 C13 C14 -177.1(4) . . . . ?
N2 S1 C13 C14 -62.5(4) . . . . ?
N2 C10 C9 C7 174.6(5) . . . . ?
N2 C10 C9 C11 -1.2(7) . . . . ?
N1 C10 C9 C7 -6.1(7) . . . . ?
N1 C10 C9 C11 178.0(5) . . . . ?
N1 C3 C2 C1 -179.5(5) . . . . ?
C10 N1 C3 C4 -2.8(7) . . . . ?
C10 N1 C3 C2 177.7(5) . . . . ?
C10 C9 C7 C4 4.0(8) . . . . ?
C10 C9 C7 C8 -177.1(5) . . . . ?
C10 C9 C11 O1 102.1(6) . . . . ?
C10 C9 C11 C12 -79.7(6) . . . . ?
C4 C3 C2 C1 1.0(9) . . . . ?
C4 C5 C6 C1 -1.5(10) . . . . ?
C14 C19 C18 C17 -0.1(10) . . . . ?
C14 C15 C16 C17 -1.4(9) . . . . ?
C3 N1 C10 N2 -175.3(5) . . . . ?
C3 N1 C10 C9 5.5(7) . . . . ?
C3 C4 C7 C9 -1.1(7) . . . . ?
C3 C4 C7 C8 -180.0(5) . . . . ?
C3 C4 C5 C6 1.9(8) . . . . ?
C3 C2 C1 C6 -0.5(10) . . . . ?
C7 C9 C11 O1 -73.7(8) . . . . ?
C7 C9 C11 C12 104.4(6) . . . . ?
C7 C4 C3 N1 0.4(7) . . . . ?
C7 C4 C3 C2 179.8(5) . . . . ?
C7 C4 C5 C6 -179.7(5) . . . . ?
C2 C1 C6 C5 0.7(10) . . . . ?
C5 C4 C3 N1 178.8(5) . . . . ?
C5 C4 C3 C2 -1.7(8) . . . . ?
C5 C4 C7 C9 -179.4(5) . . . . ?
C5 C4 C7 C8 1.7(8) . . . . ?
C19 C14 C15 C16 2.3(8) . . . . ?
C19 C14 C13 S1 -92.0(6) . . . . ?
C19 C18 C17 C16 1.0(10) . . . . ?
C11 C9 C7 C4 179.5(5) . . . . ?
C11 C9 C7 C8 -1.6(8) . . . . ?
C15 C14 C19 C18 -1.5(9) . . . . ?
C15 C14 C13 S1 85.0(6) . . . . ?
C15 C16 C17 C18 -0.3(10) . . . . ?
C13 S1 N2 C10 87.8(5) . . . . ?
C13 C14 C19 C18 175.6(5) . . . . ?
C13 C14 C15 C16 -174.8(5) . . . . ?
