#------------------------------------------------------------------------------
#$Date: 2020-02-04 22:04:10 +0200 (Tue, 04 Feb 2020) $
#$Revision: 247590 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/58/7125815.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_7125815
loop_
_publ_author_name
'Zhao, Xiaolei'
'Zheng, Wei'
'Zhang, Yi'
'Huang, Wei'
_publ_section_title
;
 cis alkenes stabilized by intramolecular sulphurπ interactions.
;
_journal_issue                   5
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              814
_journal_page_last               817
_journal_paper_doi               10.1039/c9cc08558k
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C23 H21 Cl N4 S'
_chemical_formula_sum            'C23 H21 Cl N4 S'
_chemical_formula_weight         420.95
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-01-22 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.253(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7727(15)
_cell_length_b                   7.6261(8)
_cell_length_c                   19.442(2)
_cell_measurement_reflns_used    2172
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      20.773
_cell_measurement_theta_min      2.411
_cell_volume                     2181.1(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (BRUKER 2000)'
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15589
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.104
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.158
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3811
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0662
_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)+(0.0822P)²+1.9678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1768
_refine_ls_wR_factor_ref         0.1920
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2730
_reflns_number_total             3811
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc08558k2.cif
_cod_data_source_block           trans-6
_cod_depositor_comments
'Adding full bibliography for 7125813--7125817.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7125815
_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_min   0.966
_shelx_estimated_absorpt_t_max   0.972
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
C1 C 0.1418(2) 0.0840(4) 0.03920(18) 0.0509(9) Uani 1 1 d . .
C2 C 0.1939(2) 0.0865(5) -0.01501(18) 0.0512(8) Uani 1 1 d . .
C3 C 0.2453(2) 0.2417(5) -0.02023(18) 0.0519(9) Uani 1 1 d . .
C4 C 0.2306(2) 0.3597(5) 0.03079(18) 0.0499(8) Uani 1 1 d . .
C5 C 0.0861(2) -0.0584(5) 0.0600(2) 0.0547(9) Uani 1 1 d . .
H5 H 0.0834 -0.1580 0.0323 0.066 Uiso 1 1 calc R U
C6 C 0.0379(3) -0.0623(5) 0.1148(2) 0.0612(10) Uani 1 1 d . .
H6 H 0.0381 0.0386 0.1417 0.073 Uiso 1 1 calc R U
C7 C -0.0151(2) -0.2108(5) 0.1364(2) 0.0583(10) Uani 1 1 d . .
C8 C -0.0661(3) -0.1916(7) 0.1919(2) 0.0800(13) Uani 1 1 d . .
H8 H -0.0650 -0.0853 0.2154 0.096 Uiso 1 1 calc R U
C9 C -0.1193(4) -0.3285(9) 0.2134(3) 0.0986(17) Uani 1 1 d . .
H9 H -0.1537 -0.3136 0.2507 0.118 Uiso 1 1 calc R U
C10 C -0.1205(4) -0.4849(9) 0.1789(3) 0.1014(18) Uani 1 1 d . .
H10 H -0.1560 -0.5768 0.1928 0.122 Uiso 1 1 calc R U
C11 C -0.0699(3) -0.5069(7) 0.1245(3) 0.0929(15) Uani 1 1 d . .
H11 H -0.0707 -0.6138 0.1014 0.112 Uiso 1 1 calc R U
C12 C -0.0173(3) -0.3708(6) 0.1034(3) 0.0765(12) Uani 1 1 d . .
H12 H 0.0172 -0.3875 0.0663 0.092 Uiso 1 1 calc R U
C13 C 0.3078(3) 0.2718(6) -0.0704(2) 0.0731(12) Uani 1 1 d . .
C14 C 0.3012(2) 0.7570(4) 0.10654(18) 0.0487(8) Uani 1 1 d . .
C15 C 0.3664(3) 0.8263(5) 0.06699(18) 0.0582(10) Uani 1 1 d . .
H15 H 0.3798 0.7687 0.0270 0.070 Uiso 1 1 calc R U
C16 C 0.4109(3) 0.9770(5) 0.08591(19) 0.0656(11) Uani 1 1 d . .
H16 H 0.4526 1.0224 0.0576 0.079 Uiso 1 1 calc R U
C17 C 0.3957(3) 1.0668(5) 0.14719(19) 0.0579(9) Uani 1 1 d . .
C18 C 0.3291(2) 0.9962(5) 0.18672(19) 0.0537(9) Uani 1 1 d . .
H18 H 0.3161 1.0518 0.2272 0.064 Uiso 1 1 calc R U
C19 C 0.2833(2) 0.8462(5) 0.16598(18) 0.0511(8) Uani 1 1 d . .
H19 H 0.2389 0.8031 0.1925 0.061 Uiso 1 1 calc R U
C20 C 0.4886(4) 1.3274(8) 0.1133(3) 0.118(2) Uani 1 1 d D U
H20A H 0.4627 1.3038 0.0665 0.142 Uiso 1 1 calc R U
H20B H 0.4840 1.4518 0.1229 0.142 Uiso 1 1 calc R U
C21 C 0.5812(5) 1.2662(9) 0.1246(3) 0.132(2) Uani 1 1 d D U
H21A H 0.6047 1.2920 0.1712 0.198 Uiso 1 1 calc R U
H21B H 0.6177 1.3240 0.0930 0.198 Uiso 1 1 calc R U
H21C H 0.5829 1.1419 0.1171 0.198 Uiso 1 1 calc R U
C22 C 0.4393(3) 1.2888(6) 0.2369(2) 0.0736(12) Uani 1 1 d . .
H22A H 0.4974 1.3422 0.2516 0.088 Uiso 1 1 calc R U
H22B H 0.4287 1.1956 0.2692 0.088 Uiso 1 1 calc R U
C23 C 0.3657(5) 1.4241(7) 0.2387(3) 0.1067(19) Uani 1 1 d . .
H23A H 0.3788 1.5215 0.2099 0.160 Uiso 1 1 calc R U
H23B H 0.3628 1.4638 0.2853 0.160 Uiso 1 1 calc R U
H23C H 0.3084 1.3733 0.2219 0.160 Uiso 1 1 calc R U
Cl1 Cl 0.20183(7) -0.08581(13) -0.07081(5) 0.0702(4) Uani 1 1 d . .
N1 N 0.2751(2) 0.5178(4) 0.03933(15) 0.0532(7) Uani 1 1 d . .
N2 N 0.2538(2) 0.6029(4) 0.09258(15) 0.0523(7) Uani 1 1 d . .
N3 N 0.3580(4) 0.2954(7) -0.1097(3) 0.123(2) Uani 1 1 d . .
N4 N 0.4427(3) 1.2136(5) 0.16746(19) 0.0875(12) Uani 1 1 d D U
S1 S 0.15379(6) 0.27983(12) 0.08519(5) 0.0557(3) 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C2 C1 C5 127.3(3)
C2 C1 S1 110.3(3)
C5 C1 S1 122.3(3)
C1 C2 C3 114.4(3)
C1 C2 Cl1 123.7(3)
C3 C2 Cl1 121.8(3)
C4 C3 C2 112.0(3)
C4 C3 C13 123.1(3)
C2 C3 C13 124.8(3)
C3 C4 N1 123.8(3)
C3 C4 S1 111.5(3)
N1 C4 S1 124.6(3)
C6 C5 C1 126.9(4)
C6 C5 H5 116.5
C1 C5 H5 116.5
C5 C6 C7 125.8(4)
C5 C6 H6 117.1
C7 C6 H6 117.1
C12 C7 C8 117.8(4)
C12 C7 C6 123.0(4)
C8 C7 C6 119.2(4)
C7 C8 C9 121.2(5)
C7 C8 H8 119.4
C9 C8 H8 119.4
C10 C9 C8 119.2(5)
C10 C9 H9 120.4
C8 C9 H9 120.4
C11 C10 C9 120.4(5)
C11 C10 H10 119.8
C9 C10 H10 119.8
C10 C11 C12 120.2(5)
C10 C11 H11 119.9
C12 C11 H11 119.9
C7 C12 C11 121.2(5)
C7 C12 H12 119.4
C11 C12 H12 119.4
N3 C13 C3 179.4(6)
N2 C14 C19 116.7(3)
N2 C14 C15 125.4(3)
C19 C14 C15 117.9(3)
C16 C15 C14 121.0(3)
C16 C15 H15 119.5
C14 C15 H15 119.5
C15 C16 C17 121.9(4)
C15 C16 H16 119.0
C17 C16 H16 119.0
N4 C17 C18 121.4(3)
N4 C17 C16 121.9(4)
C18 C17 C16 116.7(3)
C19 C18 C17 120.6(3)
C19 C18 H18 119.7
C17 C18 H18 119.7
C18 C19 C14 121.8(3)
C18 C19 H19 119.1
C14 C19 H19 119.1
C21 C20 N4 100.4(5)
C21 C20 H20A 111.7
N4 C20 H20A 111.7
C21 C20 H20B 111.7
N4 C20 H20B 111.7
H20A C20 H20B 109.5
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
N4 C22 C23 112.0(4)
N4 C22 H22A 109.2
C23 C22 H22A 109.2
N4 C22 H22B 109.2
C23 C22 H22B 109.2
H22A C22 H22B 107.9
C22 C23 H23A 109.5
C22 C23 H23B 109.5
H23A C23 H23B 109.5
C22 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
N2 N1 C4 113.0(3)
N1 N2 C14 115.5(3)
C17 N4 C22 121.9(4)
C17 N4 C20 120.2(4)
C22 N4 C20 117.0(4)
C4 S1 C1 91.70(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.360(5)
C1 C5 1.443(5)
C1 S1 1.741(3)
C2 C3 1.415(5)
C2 Cl1 1.715(4)
C3 C4 1.371(5)
C3 C13 1.422(5)
C4 N1 1.376(4)
C4 S1 1.732(4)
C5 C6 1.335(5)
C5 H5 0.9300
C6 C7 1.459(5)
C6 H6 0.9300
C7 C12 1.378(6)
C7 C8 1.379(6)
C8 C9 1.394(7)
C8 H8 0.9300
C9 C10 1.368(8)
C9 H9 0.9300
C10 C11 1.360(7)
C10 H10 0.9300
C11 C12 1.380(6)
C11 H11 0.9300
C12 H12 0.9300
C13 N3 1.126(6)
C14 N2 1.382(4)
C14 C19 1.387(5)
C14 C15 1.391(5)
C15 C16 1.358(5)
C15 H15 0.9300
C16 C17 1.410(5)
C16 H16 0.9300
C17 N4 1.358(5)
C17 C18 1.409(5)
C18 C19 1.371(5)
C18 H18 0.9300
C19 H19 0.9300
C20 C21 1.443(7)
C20 N4 1.566(6)
C20 H20A 0.9700
C20 H20B 0.9700
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
C22 N4 1.472(5)
C22 C23 1.501(7)
C22 H22A 0.9700
C22 H22B 0.9700
C23 H23A 0.9600
C23 H23B 0.9600
C23 H23C 0.9600
N1 N2 1.285(4)
