# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_VM1855
_database_code_depnum_ccdc_archive 'CCDC 2107310'
loop_
_audit_author_name
_audit_author_address
'Darina Ildarovna Nasyrova'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-09-03 deposited with the CCDC.	2022-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H11 Cl F N O S'
_chemical_formula_sum            'C19 H11 Cl F N O S'
_chemical_formula_weight         355.80

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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'

_cell_length_a                   11.9876(12)
_cell_length_b                   10.8264(11)
_cell_length_c                   13.1607(14)
_cell_angle_alpha                90
_cell_angle_beta                 108.645(3)
_cell_angle_gamma                90
_cell_volume                     1618.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      31.89
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.380
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4771
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-Ray tube'
_diffrn_source_power             50
_diffrn_source_current           30
_diffrn_source_size              '0.6 mm, fine-focus'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            31501
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_av_R_equivalents  0.0870
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.491
_diffrn_reflns_theta_max         30.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4930
_reflns_number_gt                3516
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    
'SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0622P)²+2.2847P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4930
_refine_ls_number_parameters     239
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0674
_refine_ls_wR_factor_ref         0.1837
_refine_ls_wR_factor_gt          0.1647
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C7A C 0.4751(3) 0.4947(3) 0.2480(2) 0.0239(6) Uani 0.7822(14) 1 d D . P A 1
C8A C 0.3663(3) 0.4785(3) 0.2638(3) 0.0260(6) Uani 0.7822(14) 1 d D . P A 1
C9A C 0.2759(3) 0.4109(3) 0.1920(3) 0.0307(7) Uani 0.7822(14) 1 d D . P A 1
H9A H 0.202392 0.400894 0.204040 0.037 Uiso 0.7822(14) 1 calc R U P A 1
C10A C 0.2951(4) 0.3587(4) 0.1033(3) 0.0374(8) Uani 0.7822(14) 1 d D . P A 1
H10A H 0.234637 0.311264 0.054715 0.045 Uiso 0.7822(14) 1 calc R U P A 1
C11A C 0.4015(3) 0.3747(4) 0.0840(3) 0.0354(7) Uani 0.7822(14) 1 d D . P A 1
H11A H 0.413455 0.338981 0.022346 0.043 Uiso 0.7822(14) 1 calc R U P A 1
C12A C 0.4908(3) 0.4434(3) 0.1558(3) 0.0293(6) Uani 0.7822(14) 1 d D . P A 1
H12A H 0.563093 0.455512 0.142056 0.035 Uiso 0.7822(14) 1 calc R U P A 1
Cl1A Cl 0.34257(7) 0.53516(9) 0.37844(7) 0.0342(2) Uani 0.7822(14) 1 d D . P A
1
C7B C 0.4584(6) 0.4933(12) 0.2824(7) 0.0239(6) Uani 0.2178(14) 1 d D . P A 2
C12B C 0.3649(7) 0.4782(11) 0.3231(9) 0.0293(6) Uani 0.2178(14) 1 d D . P A 2
H12B H 0.369960 0.511062 0.391376 0.035 Uiso 0.2178(14) 1 calc R U P A 2
C11B C 0.2642(10) 0.4146(12) 0.2632(9) 0.0354(7) Uani 0.2178(14) 1 d D . P A 2
H11B H 0.198942 0.406801 0.288835 0.043 Uiso 0.2178(14) 1 calc R U P A 2
C10B C 0.2605(11) 0.3627(14) 0.1656(9) 0.0374(8) Uani 0.2178(14) 1 d D . P A 2
H10B H 0.193217 0.315900 0.126982 0.045 Uiso 0.2178(14) 1 calc R U P A 2
C9B C 0.3509(8) 0.3765(12) 0.1226(9) 0.0307(7) Uani 0.2178(14) 1 d D . P A 2
H9B H 0.345831 0.342499 0.054765 0.037 Uiso 0.2178(14) 1 calc R U P A 2
C8B C 0.4498(7) 0.4425(11) 0.1829(7) 0.0260(6) Uani 0.2178(14) 1 d D . P A 2
Cl1B Cl 0.5630(3) 0.4634(3) 0.1291(2) 0.0342(2) Uani 0.2178(14) 1 d D . P A 2
O1 O 0.84337(16) 0.36873(19) 0.41396(17) 0.0350(4) Uani 1 1 d . . . . .
C1 C 0.5737(2) 0.5573(3) 0.3322(2) 0.0302(5) Uani 1 1 d D . . . .
S1 S 0.77053(7) 0.82926(7) 0.50356(6) 0.0375(2) Uani 1 1 d . . . . .
F1 F 0.48955(15) 0.76285(16) 0.32728(16) 0.0449(5) Uani 1 1 d . . . . .
C2 C 0.5781(2) 0.6807(3) 0.3617(2) 0.0326(6) Uani 1 1 d . . . . .
N1 N 0.75459(18) 0.6025(2) 0.44270(17) 0.0273(4) Uani 1 1 d . . . . .
C3 C 0.6896(2) 0.7086(3) 0.4300(2) 0.0307(5) Uani 1 1 d . . . . .
C4 C 0.8912(2) 0.7306(3) 0.5509(2) 0.0361(6) Uani 1 1 d . . . . .
H4 H 0.965049 0.756151 0.599036 0.043 Uiso 1 1 calc R U . . .
C6 C 0.6858(2) 0.5060(2) 0.3850(2) 0.0280(5) Uani 1 1 d . . . . .
C5 C 0.8698(2) 0.6157(3) 0.5129(2) 0.0319(6) Uani 1 1 d . . . . .
H5 H 0.925855 0.550597 0.531291 0.038 Uiso 1 1 calc R U . . .
C15 C 0.5540(2) 0.2631(3) 0.3832(2) 0.0303(5) Uani 1 1 d . . . . .
H15 H 0.533042 0.326664 0.423481 0.036 Uiso 1 1 calc R U . . .
C14 C 0.6551(2) 0.2754(2) 0.3533(2) 0.0265(5) Uani 1 1 d . . . . .
C13 C 0.7351(2) 0.3840(3) 0.3857(2) 0.0278(5) Uani 1 1 d . . . . .
C16 C 0.4839(3) 0.1584(3) 0.3545(3) 0.0386(7) Uani 1 1 d . . . . .
H16 H 0.415716 0.149472 0.375820 0.046 Uiso 1 1 calc R U . . .
C17 C 0.5145(3) 0.0666(3) 0.2941(3) 0.0464(8) Uani 1 1 d . . . . .
H17 H 0.465518 -0.003894 0.272258 0.056 Uiso 1 1 calc R U . . .
C18 C 0.6159(3) 0.0774(3) 0.2655(3) 0.0431(7) Uani 1 1 d . . . . .
H18 H 0.636741 0.013695 0.225314 0.052 Uiso 1 1 calc R U . . .
C19 C 0.6867(3) 0.1809(3) 0.2956(2) 0.0345(6) Uani 1 1 d . . . . .
H19 H 0.756851 0.187553 0.277059 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C7A C8A 1.396(4) . ?
C7A C12A 1.400(4) . ?
C7A C1 1.499(4) . ?
C8A C9A 1.396(5) . ?
C8A Cl1A 1.735(3) . ?
C9A C10A 1.381(5) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.388(5) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.394(5) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C7B C8B 1.393(5) . ?
C7B C12B 1.398(5) . ?
C7B C1 1.497(5) . ?
C12B C11B 1.394(6) . ?
C12B H12B 0.9500 . ?
C11B C10B 1.390(6) . ?
C11B H11B 0.9500 . ?
C10B C9B 1.382(6) . ?
C10B H10B 0.9500 . ?
C9B C8B 1.395(5) . ?
C9B H9B 0.9500 . ?
C8B Cl1B 1.733(4) . ?
O1 C13 1.242(3) . ?
C1 C2 1.388(4) . ?
C1 C6 1.414(4) . ?
S1 C3 1.727(3) . ?
S1 C4 1.746(3) . ?
F1 C2 1.347(3) . ?
C2 C3 1.385(4) . ?
N1 C3 1.367(4) . ?
N1 C6 1.396(3) . ?
N1 C5 1.402(3) . ?
C4 C5 1.334(4) . ?
C4 H4 0.9500 . ?
C6 C13 1.445(4) . ?
C5 H5 0.9500 . ?
C15 C16 1.390(4) . ?
C15 C14 1.395(3) . ?
C15 H15 0.9500 . ?
C14 C19 1.397(4) . ?
C14 C13 1.491(4) . ?
C16 C17 1.393(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

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
C8A C7A C12A 118.0(3) . . ?
C8A C7A C1 120.0(3) . . ?
C12A C7A C1 121.8(3) . . ?
C7A C8A C9A 121.7(3) . . ?
C7A C8A Cl1A 120.4(2) . . ?
C9A C8A Cl1A 117.8(2) . . ?
C10A C9A C8A 118.9(3) . . ?
C10A C9A H9A 120.6 . . ?
C8A C9A H9A 120.6 . . ?
C9A C10A C11A 121.0(3) . . ?
C9A C10A H10A 119.5 . . ?
C11A C10A H10A 119.5 . . ?
C10A C11A C12A 119.5(3) . . ?
C10A C11A H11A 120.2 . . ?
C12A C11A H11A 120.2 . . ?
C11A C12A C7A 120.8(3) . . ?
C11A C12A H12A 119.6 . . ?
C7A C12A H12A 119.6 . . ?
C8B C7B C12B 119.1(6) . . ?
C8B C7B C1 112.0(6) . . ?
C12B C7B C1 128.8(6) . . ?
C11B C12B C7B 119.7(9) . . ?
C11B C12B H12B 120.1 . . ?
C7B C12B H12B 120.1 . . ?
C10B C11B C12B 119.3(12) . . ?
C10B C11B H11B 120.4 . . ?
C12B C11B H11B 120.4 . . ?
C9B C10B C11B 122.4(12) . . ?
C9B C10B H10B 118.8 . . ?
C11B C10B H10B 118.8 . . ?
C10B C9B C8B 117.3(10) . . ?
C10B C9B H9B 121.3 . . ?
C8B C9B H9B 121.3 . . ?
C7B C8B C9B 122.0(6) . . ?
C7B C8B Cl1B 120.0(6) . . ?
C9B C8B Cl1B 118.0(6) . . ?
C2 C1 C6 107.2(2) . . ?
C2 C1 C7B 121.0(6) . . ?
C6 C1 C7B 129.2(6) . . ?
C2 C1 C7A 126.3(3) . . ?
C6 C1 C7A 125.9(3) . . ?
C3 S1 C4 89.42(14) . . ?
F1 C2 C3 124.6(3) . . ?
F1 C2 C1 125.9(2) . . ?
C3 C2 C1 109.5(2) . . ?
C3 N1 C6 110.4(2) . . ?
C3 N1 C5 113.5(2) . . ?
C6 N1 C5 136.1(2) . . ?
N1 C3 C2 106.9(2) . . ?
N1 C3 S1 111.76(19) . . ?
C2 C3 S1 141.4(2) . . ?
C5 C4 S1 113.5(2) . . ?
C5 C4 H4 123.3 . . ?
S1 C4 H4 123.3 . . ?
N1 C6 C1 106.0(2) . . ?
N1 C6 C13 120.7(2) . . ?
C1 C6 C13 133.2(2) . . ?
C4 C5 N1 111.9(3) . . ?
C4 C5 H5 124.1 . . ?
N1 C5 H5 124.1 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C14 C19 119.7(2) . . ?
C15 C14 C13 122.1(2) . . ?
C19 C14 C13 118.2(2) . . ?
O1 C13 C6 120.7(2) . . ?
O1 C13 C14 119.7(2) . . ?
C6 C13 C14 119.6(2) . . ?
C15 C16 C17 119.3(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?

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
C12A C7A C8A C9A 1.5(5) . . . . ?
C1 C7A C8A C9A -174.0(3) . . . . ?
C12A C7A C8A Cl1A 177.8(3) . . . . ?
C1 C7A C8A Cl1A 2.3(4) . . . . ?
C7A C8A C9A C10A 0.1(5) . . . . ?
Cl1A C8A C9A C10A -176.3(3) . . . . ?
C8A C9A C10A C11A -1.2(6) . . . . ?
C9A C10A C11A C12A 0.6(6) . . . . ?
C10A C11A C12A C7A 1.1(6) . . . . ?
C8A C7A C12A C11A -2.1(5) . . . . ?
C1 C7A C12A C11A 173.4(3) . . . . ?
C8B C7B C12B C11B -1(2) . . . . ?
C1 C7B C12B C11B -179.9(12) . . . . ?
C7B C12B C11B C10B 3(2) . . . . ?
C12B C11B C10B C9B -3(2) . . . . ?
C11B C10B C9B C8B 2(2) . . . . ?
C12B C7B C8B C9B 0(2) . . . . ?
C1 C7B C8B C9B 178.8(11) . . . . ?
C12B C7B C8B Cl1B 178.4(10) . . . . ?
C1 C7B C8B Cl1B -2.6(15) . . . . ?
C10B C9B C8B C7B 0(2) . . . . ?
C10B C9B C8B Cl1B -178.8(11) . . . . ?
C8B C7B C1 C2 123.2(9) . . . . ?
C12B C7B C1 C2 -58.0(16) . . . . ?
C8B C7B C1 C6 -77.3(11) . . . . ?
C12B C7B C1 C6 101.5(14) . . . . ?
C8A C7A C1 C2 -67.8(4) . . . . ?
C12A C7A C1 C2 116.8(4) . . . . ?
C8A C7A C1 C6 121.8(3) . . . . ?
C12A C7A C1 C6 -53.5(5) . . . . ?
C6 C1 C2 F1 178.9(3) . . . . ?
C7B C1 C2 F1 -17.6(6) . . . . ?
C7A C1 C2 F1 7.1(5) . . . . ?
C6 C1 C2 C3 0.8(3) . . . . ?
C7B C1 C2 C3 164.3(5) . . . . ?
C7A C1 C2 C3 -171.0(3) . . . . ?
C6 N1 C3 C2 -1.1(3) . . . . ?
C5 N1 C3 C2 -178.3(2) . . . . ?
C6 N1 C3 S1 178.16(18) . . . . ?
C5 N1 C3 S1 1.0(3) . . . . ?
F1 C2 C3 N1 -177.9(3) . . . . ?
C1 C2 C3 N1 0.2(3) . . . . ?
F1 C2 C3 S1 3.2(6) . . . . ?
C1 C2 C3 S1 -178.7(3) . . . . ?
C4 S1 C3 N1 -0.5(2) . . . . ?
C4 S1 C3 C2 178.4(4) . . . . ?
C3 S1 C4 C5 0.0(2) . . . . ?
C3 N1 C6 C1 1.6(3) . . . . ?
C5 N1 C6 C1 177.9(3) . . . . ?
C3 N1 C6 C13 179.9(2) . . . . ?
C5 N1 C6 C13 -3.8(4) . . . . ?
C2 C1 C6 N1 -1.4(3) . . . . ?
C7B C1 C6 N1 -163.1(4) . . . . ?
C7A C1 C6 N1 170.4(3) . . . . ?
C2 C1 C6 C13 -179.5(3) . . . . ?
C7B C1 C6 C13 18.8(6) . . . . ?
C7A C1 C6 C13 -7.6(5) . . . . ?
S1 C4 C5 N1 0.6(3) . . . . ?
C3 N1 C5 C4 -1.0(3) . . . . ?
C6 N1 C5 C4 -177.2(3) . . . . ?
C16 C15 C14 C19 -1.0(4) . . . . ?
C16 C15 C14 C13 -177.8(3) . . . . ?
N1 C6 C13 O1 -18.1(4) . . . . ?
C1 C6 C13 O1 159.7(3) . . . . ?
N1 C6 C13 C14 161.3(2) . . . . ?
C1 C6 C13 C14 -20.9(4) . . . . ?
C15 C14 C13 O1 139.4(3) . . . . ?
C19 C14 C13 O1 -37.4(4) . . . . ?
C15 C14 C13 C6 -40.0(4) . . . . ?
C19 C14 C13 C6 143.2(3) . . . . ?
C14 C15 C16 C17 -1.0(5) . . . . ?
C15 C16 C17 C18 2.0(5) . . . . ?
C16 C17 C18 C19 -1.0(6) . . . . ?
C17 C18 C19 C14 -1.0(5) . . . . ?
C15 C14 C19 C18 2.0(4) . . . . ?
C13 C14 C19 C18 178.9(3) . . . . ?

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.083

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_VM1966
_database_code_depnum_ccdc_archive 'CCDC 2107335'
loop_
_audit_author_name
_audit_author_address
'Egor Igorevich Tuzharov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-09-03 deposited with the CCDC.	2022-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16 Cl F N2 O'
_chemical_formula_sum            'C24 H16 Cl F N2 O'
_chemical_formula_weight         402.84

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'

_cell_length_a                   27.2572(12)
_cell_length_b                   10.8688(5)
_cell_length_c                   13.4118(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.945(2)
_cell_angle_gamma                90
_cell_volume                     3735.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9890
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      34.80
_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             1664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.440
_exptl_absorpt_coefficient_mu    0.233
_shelx_estimated_absorpt_T_min   0.890
_shelx_estimated_absorpt_T_max   0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6941
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-Ray tube'
_diffrn_source_power             50
_diffrn_source_current           30
_diffrn_source_size              '0.6 mm, fine-focus'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            54826
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.035
_diffrn_reflns_theta_max         33.140
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7131
_reflns_number_gt                5652
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+4.4024P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7131
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.0995
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Cl1 Cl 0.50459(2) 0.84059(3) 0.41205(3) 0.02700(8) Uani 1 1 d . . . . .
C1 C 0.29831(4) 0.58652(10) 0.54925(8) 0.01434(19) Uani 1 1 d . . . . .
F1 F 0.32196(3) 0.42141(7) 0.34015(6) 0.02052(15) Uani 1 1 d . . . . .
O1 O 0.25991(3) 0.72606(8) 0.63468(7) 0.01869(17) Uani 1 1 d . . . . .
N1 N 0.21240(4) 0.47918(9) 0.53904(7) 0.01591(18) Uani 1 1 d . . . . .
N2 N 0.25712(4) 0.50526(9) 0.51390(7) 0.01418(17) Uani 1 1 d . . . . .
C2 C 0.32968(4) 0.56336(10) 0.48509(8) 0.01444(19) Uani 1 1 d . . . . .
C3 C 0.30549(4) 0.46834(11) 0.41619(8) 0.01536(19) Uani 1 1 d . . . . .
C5 C 0.21567(4) 0.35262(10) 0.40267(8) 0.01476(19) Uani 1 1 d . . . . .
C4 C 0.26018(4) 0.43210(11) 0.43317(8) 0.01475(19) Uani 1 1 d . . . . .
C6 C 0.19649(5) 0.26422(11) 0.32326(9) 0.0171(2) Uani 1 1 d . . . . .
H6 H 0.214185 0.246238 0.275008 0.020 Uiso 1 1 calc R U . . .
C7 C 0.15074(5) 0.20345(11) 0.31709(9) 0.0196(2) Uani 1 1 d . . . . .
H7 H 0.136858 0.142917 0.263783 0.024 Uiso 1 1 calc R U . . .
C8 C 0.12474(5) 0.23019(12) 0.38844(10) 0.0206(2) Uani 1 1 d . . . . .
H8 H 0.093887 0.186023 0.383195 0.025 Uiso 1 1 calc R U . . .
C9 C 0.14283(5) 0.31954(11) 0.46671(10) 0.0190(2) Uani 1 1 d . . . . .
H9 H 0.124859 0.337670 0.514444 0.023 Uiso 1 1 calc R U . . .
C10 C 0.18837(4) 0.38117(11) 0.47201(9) 0.01511(19) Uani 1 1 d . . . . .
C11 C 0.21635(5) 0.48096(12) 0.65066(9) 0.0196(2) Uani 1 1 d . . . . .
H11A H 0.191157 0.422860 0.661577 0.029 Uiso 1 1 calc R U . . .
H11B H 0.208819 0.564012 0.669969 0.029 Uiso 1 1 calc R U . . .
H11C H 0.251736 0.457183 0.695171 0.029 Uiso 1 1 calc R U . . .
C12 C 0.29992(4) 0.68615(10) 0.62281(8) 0.01454(19) Uani 1 1 d . . . . .
C13 C 0.35186(4) 0.74069(11) 0.68352(8) 0.01505(19) Uani 1 1 d . . . . .
C17 C 0.44332(5) 0.72179(13) 0.78627(10) 0.0233(2) Uani 1 1 d . . . . .
H17 H 0.473194 0.671941 0.818315 0.028 Uiso 1 1 calc R U . . .
C16 C 0.44687(5) 0.84895(14) 0.79848(10) 0.0259(3) Uani 1 1 d . . . . .
H16 H 0.479370 0.885857 0.837356 0.031 Uiso 1 1 calc R U . . .
C15 C 0.40302(5) 0.92214(12) 0.75399(10) 0.0234(2) Uani 1 1 d . . . . .
H15 H 0.405574 1.009059 0.761462 0.028 Uiso 1 1 calc R U . . .
C14 C 0.35547(5) 0.86760(11) 0.69857(9) 0.0187(2) Uani 1 1 d . . . . .
H14 H 0.325156 0.917216 0.670696 0.022 Uiso 1 1 calc R U . . .
C18 C 0.39619(5) 0.66755(12) 0.72734(9) 0.0179(2) Uani 1 1 d . . . . .
H18 H 0.394107 0.580996 0.716849 0.022 Uiso 1 1 calc R U . . .
C23 C 0.45654(4) 0.63351(12) 0.44242(9) 0.0194(2) Uani 1 1 d . . . . .
H23 H 0.484593 0.590122 0.431702 0.023 Uiso 1 1 calc R U . . .
C24 C 0.41627(4) 0.56995(11) 0.46121(9) 0.0172(2) Uani 1 1 d . . . . .
H24 H 0.417204 0.482621 0.464281 0.021 Uiso 1 1 calc R U . . .
C22 C 0.45522(4) 0.76121(12) 0.43952(9) 0.0186(2) Uani 1 1 d . . . . .
C21 C 0.41462(5) 0.82606(11) 0.45544(9) 0.0182(2) Uani 1 1 d . . . . .
H21 H 0.414632 0.913465 0.455191 0.022 Uiso 1 1 calc R U . . .
C20 C 0.37399(4) 0.76164(11) 0.47175(8) 0.0158(2) Uani 1 1 d . . . . .
H20 H 0.345568 0.805576 0.480344 0.019 Uiso 1 1 calc R U . . .
C19 C 0.37432(4) 0.63296(11) 0.47569(8) 0.01452(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Cl1 C22 1.7404(12) . ?
C1 N2 1.3792(14) . ?
C1 C2 1.4272(15) . ?
C1 C12 1.4555(16) . ?
F1 C3 1.3468(12) . ?
O1 C12 1.2332(13) . ?
N1 N2 1.4002(13) . ?
N1 C10 1.4037(15) . ?
N1 C11 1.4640(14) . ?
N2 C4 1.3686(14) . ?
C2 C3 1.3927(16) . ?
C2 C19 1.4742(15) . ?
C3 C4 1.3872(15) . ?
C5 C6 1.3968(16) . ?
C5 C10 1.4097(15) . ?
C5 C4 1.4306(16) . ?
C6 C7 1.3886(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.4017(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.3910(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.3908(16) . ?
C9 H9 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.4942(16) . ?
C13 C14 1.3927(17) . ?
C13 C18 1.3975(16) . ?
C17 C18 1.3891(17) . ?
C17 C16 1.391(2) . ?
C17 H17 0.9500 . ?
C16 C15 1.390(2) . ?
C16 H16 0.9500 . ?
C15 C14 1.3880(18) . ?
C15 H15 0.9500 . ?
C14 H14 0.9500 . ?
C18 H18 0.9500 . ?
C23 C22 1.3886(18) . ?
C23 C24 1.3909(16) . ?
C23 H23 0.9500 . ?
C24 C19 1.4021(15) . ?
C24 H24 0.9500 . ?
C22 C21 1.3886(17) . ?
C21 C20 1.3892(16) . ?
C21 H21 0.9500 . ?
C20 C19 1.3995(16) . ?
C20 H20 0.9500 . ?

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
N2 C1 C2 105.35(9) . . ?
N2 C1 C12 122.83(10) . . ?
C2 C1 C12 130.86(10) . . ?
N2 N1 C10 104.70(8) . . ?
N2 N1 C11 118.50(9) . . ?
C10 N1 C11 121.36(10) . . ?
C4 N2 C1 112.45(9) . . ?
C4 N2 N1 111.46(9) . . ?
C1 N2 N1 136.09(9) . . ?
C3 C2 C1 106.59(9) . . ?
C3 C2 C19 122.79(9) . . ?
C1 C2 C19 130.00(10) . . ?
F1 C3 C4 124.21(10) . . ?
F1 C3 C2 125.35(10) . . ?
C4 C3 C2 110.37(9) . . ?
C6 C5 C10 120.66(10) . . ?
C6 C5 C4 133.93(10) . . ?
C10 C5 C4 105.40(9) . . ?
N2 C4 C3 105.24(10) . . ?
N2 C4 C5 107.61(9) . . ?
C3 C4 C5 147.15(10) . . ?
C7 C6 C5 117.88(11) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C6 C7 C8 120.90(11) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 121.90(11) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C10 C9 C8 117.07(11) . . ?
C10 C9 H9 121.5 . . ?
C8 C9 H9 121.5 . . ?
C9 C10 N1 127.70(10) . . ?
C9 C10 C5 121.54(11) . . ?
N1 C10 C5 110.70(10) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 C1 121.72(10) . . ?
O1 C12 C13 120.35(10) . . ?
C1 C12 C13 117.93(9) . . ?
C14 C13 C18 119.63(11) . . ?
C14 C13 C12 118.61(10) . . ?
C18 C13 C12 121.74(11) . . ?
C18 C17 C16 120.15(12) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C15 C16 C17 120.21(12) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C14 C15 C16 119.65(12) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C14 C13 120.49(12) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C17 C18 C13 119.80(12) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
C22 C23 C24 119.14(11) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C23 C24 C19 120.92(11) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C21 C22 C23 121.16(11) . . ?
C21 C22 Cl1 119.68(10) . . ?
C23 C22 Cl1 119.13(9) . . ?
C22 C21 C20 119.23(11) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C20 C19 120.96(11) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C19 C24 118.55(10) . . ?
C20 C19 C2 121.42(10) . . ?
C24 C19 C2 119.81(10) . . ?

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
C2 C1 N2 C4 0.46(12) . . . . ?
C12 C1 N2 C4 170.35(10) . . . . ?
C2 C1 N2 N1 -178.77(12) . . . . ?
C12 C1 N2 N1 -8.87(19) . . . . ?
C10 N1 N2 C4 2.38(12) . . . . ?
C11 N1 N2 C4 141.38(10) . . . . ?
C10 N1 N2 C1 -178.39(12) . . . . ?
C11 N1 N2 C1 -39.40(18) . . . . ?
N2 C1 C2 C3 -0.75(12) . . . . ?
C12 C1 C2 C3 -169.51(11) . . . . ?
N2 C1 C2 C19 170.18(11) . . . . ?
C12 C1 C2 C19 1.4(2) . . . . ?
C1 C2 C3 F1 177.86(10) . . . . ?
C19 C2 C3 F1 6.12(18) . . . . ?
C1 C2 C3 C4 0.80(13) . . . . ?
C19 C2 C3 C4 -170.93(10) . . . . ?
C1 N2 C4 C3 0.03(13) . . . . ?
N1 N2 C4 C3 179.45(9) . . . . ?
C1 N2 C4 C5 -179.69(9) . . . . ?
N1 N2 C4 C5 -0.27(12) . . . . ?
F1 C3 C4 N2 -177.62(10) . . . . ?
C2 C3 C4 N2 -0.52(13) . . . . ?
F1 C3 C4 C5 1.9(3) . . . . ?
C2 C3 C4 C5 178.98(17) . . . . ?
C6 C5 C4 N2 176.32(12) . . . . ?
C10 C5 C4 N2 -1.95(12) . . . . ?
C6 C5 C4 C3 -3.2(3) . . . . ?
C10 C5 C4 C3 178.55(17) . . . . ?
C10 C5 C6 C7 -1.81(17) . . . . ?
C4 C5 C6 C7 -179.87(12) . . . . ?
C5 C6 C7 C8 -0.02(18) . . . . ?
C6 C7 C8 C9 1.21(19) . . . . ?
C7 C8 C9 C10 -0.52(18) . . . . ?
C8 C9 C10 N1 175.81(11) . . . . ?
C8 C9 C10 C5 -1.34(17) . . . . ?
N2 N1 C10 C9 178.95(11) . . . . ?
C11 N1 C10 C9 41.43(17) . . . . ?
N2 N1 C10 C5 -3.64(12) . . . . ?
C11 N1 C10 C5 -141.17(11) . . . . ?
C6 C5 C10 C9 2.56(17) . . . . ?
C4 C5 C10 C9 -178.89(11) . . . . ?
C6 C5 C10 N1 -175.03(10) . . . . ?
C4 C5 C10 N1 3.52(13) . . . . ?
N2 C1 C12 O1 -20.99(17) . . . . ?
C2 C1 C12 O1 146.09(12) . . . . ?
N2 C1 C12 C13 159.73(10) . . . . ?
C2 C1 C12 C13 -33.20(17) . . . . ?
O1 C12 C13 C14 -39.18(15) . . . . ?
C1 C12 C13 C14 140.12(11) . . . . ?
O1 C12 C13 C18 139.22(11) . . . . ?
C1 C12 C13 C18 -41.49(14) . . . . ?
C18 C17 C16 C15 1.57(19) . . . . ?
C17 C16 C15 C14 0.92(19) . . . . ?
C16 C15 C14 C13 -2.67(18) . . . . ?
C18 C13 C14 C15 1.92(16) . . . . ?
C12 C13 C14 C15 -179.65(10) . . . . ?
C16 C17 C18 C13 -2.32(18) . . . . ?
C14 C13 C18 C17 0.58(16) . . . . ?
C12 C13 C18 C17 -177.80(10) . . . . ?
C22 C23 C24 C19 0.88(18) . . . . ?
C24 C23 C22 C21 0.26(18) . . . . ?
C24 C23 C22 Cl1 -178.08(9) . . . . ?
C23 C22 C21 C20 -1.72(18) . . . . ?
Cl1 C22 C21 C20 176.62(9) . . . . ?
C22 C21 C20 C19 2.06(17) . . . . ?
C21 C20 C19 C24 -0.95(16) . . . . ?
C21 C20 C19 C2 -175.46(10) . . . . ?
C23 C24 C19 C20 -0.54(17) . . . . ?
C23 C24 C19 C2 174.06(10) . . . . ?
C3 C2 C19 C20 127.65(12) . . . . ?
C1 C2 C19 C20 -41.99(17) . . . . ?
C3 C2 C19 C24 -46.79(16) . . . . ?
C1 C2 C19 C24 143.57(12) . . . . ?

_refine_diff_density_max         0.438
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.061

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_VM1833
_database_code_depnum_ccdc_archive 'CCDC 2107330'
loop_
_audit_author_name
_audit_author_address
'Egor Igorevich Tuzharov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-09-03 deposited with the CCDC.	2022-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 Cl N O S'
_chemical_formula_sum            'C19 H12 Cl N O S'
_chemical_formula_weight         337.81

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3208(2)
_cell_length_b                   9.0728(2)
_cell_length_c                   12.5495(3)
_cell_angle_alpha                73.2120(10)
_cell_angle_beta                 81.3380(10)
_cell_angle_gamma                73.1940(10)
_cell_volume                     761.88(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9625
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      34.96
_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.391
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6227
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-Ray tube'
_diffrn_source_power             50
_diffrn_source_current           30
_diffrn_source_size              '0.6 mm, fine-focus'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            35340
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.428
_diffrn_reflns_theta_max         34.336
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6388
_reflns_number_gt                5443
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+0.2864P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6388
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0848
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Cl1 Cl 0.58480(4) 0.29164(3) 0.94708(2) 0.02443(6) Uani 1 1 d . . . . .
C1 C 0.83477(13) 1.00885(11) 0.26442(8) 0.01570(15) Uani 1 1 d . . . . .
H3 H 0.863997 1.092891 0.283716 0.019 Uiso 1 1 calc R U . . .
S1 S 0.77681(4) 0.83100(3) 0.15174(2) 0.01907(6) Uani 1 1 d . . . . .
O1 O 0.77548(11) 1.06908(8) 0.48586(6) 0.01911(13) Uani 1 1 d . . . . .
N1 N 0.78246(11) 0.88003(9) 0.34192(6) 0.01369(13) Uani 1 1 d . . . . .
C2 C 0.83872(14) 0.99936(12) 0.15884(8) 0.01847(16) Uani 1 1 d . . . . .
H4 H 0.871743 1.076275 0.095069 0.022 Uiso 1 1 calc R U . . .
C3 C 0.74930(13) 0.77110(11) 0.29556(7) 0.01507(15) Uani 1 1 d . . . . .
C4 C 0.70377(13) 0.64700(11) 0.38028(8) 0.01547(15) Uani 1 1 d . . . . .
H5 H 0.673924 0.556069 0.371707 0.019 Uiso 1 1 calc R U . . .
C5 C 0.71059(12) 0.68270(10) 0.48170(7) 0.01372(14) Uani 1 1 d . . . . .
C6 C 0.76176(12) 0.82792(10) 0.45797(7) 0.01341(14) Uani 1 1 d . . . . .
C7 C 0.66678(12) 0.58309(10) 0.59324(7) 0.01356(14) Uani 1 1 d . . . . .
C8 C 0.53307(12) 0.64907(11) 0.67000(8) 0.01503(15) Uani 1 1 d . . . . .
H10 H 0.460190 0.756687 0.647530 0.018 Uiso 1 1 calc R U . . .
C9 C 0.50508(13) 0.55975(11) 0.77863(8) 0.01636(15) Uani 1 1 d . . . . .
H11 H 0.415557 0.605731 0.830795 0.020 Uiso 1 1 calc R U . . .
C10 C 0.61081(13) 0.40174(11) 0.80938(8) 0.01666(16) Uani 1 1 d . . . . .
C11 C 0.73694(13) 0.33040(11) 0.73347(8) 0.01736(16) Uani 1 1 d . . . . .
H12 H 0.803667 0.220923 0.755106 0.021 Uiso 1 1 calc R U . . .
C12 C 0.76423(13) 0.42159(11) 0.62516(8) 0.01623(15) Uani 1 1 d . . . . .
H2 H 0.849792 0.373802 0.572408 0.019 Uiso 1 1 calc R U . . .
C16 C 0.73498(15) 0.87122(12) 0.83774(8) 0.01975(17) Uani 1 1 d . . . . .
H7 H 0.663920 0.927403 0.890271 0.024 Uiso 1 1 calc R U . . .
C17 C 0.86242(16) 0.72286(13) 0.87425(8) 0.02099(18) Uani 1 1 d . . . . .
H1 H 0.877571 0.677457 0.951746 0.025 Uiso 1 1 calc R U . . .
C18 C 0.96775(14) 0.64093(12) 0.79720(8) 0.01853(16) Uani 1 1 d . . . . .
H6 H 1.057053 0.540983 0.822139 0.022 Uiso 1 1 calc R U . . .
C19 C 0.94251(13) 0.70509(11) 0.68387(8) 0.01516(15) Uani 1 1 d . . . . .
H19 H 1.013229 0.648433 0.631528 0.018 Uiso 1 1 calc R U . . .
C15 C 0.71172(13) 0.93716(11) 0.72431(8) 0.01638(15) Uani 1 1 d . . . . .
H8 H 0.626972 1.039467 0.699275 0.020 Uiso 1 1 calc R U . . .
C14 C 0.81293(12) 0.85302(10) 0.64719(7) 0.01339(14) Uani 1 1 d . . . . .
C13 C 0.78292(12) 0.92654(10) 0.52621(7) 0.01399(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Cl1 C10 1.7418(9) . ?
C1 C2 1.3478(13) . ?
C1 N1 1.3959(12) . ?
C1 H3 0.9500 . ?
S1 C3 1.7264(9) . ?
S1 C2 1.7429(11) . ?
O1 C13 1.2333(11) . ?
N1 C3 1.3739(12) . ?
N1 C6 1.3945(11) . ?
C2 H4 0.9500 . ?
C3 C4 1.3886(13) . ?
C4 C5 1.4121(13) . ?
C4 H5 0.9500 . ?
C5 C6 1.4107(12) . ?
C5 C7 1.4766(12) . ?
C6 C13 1.4563(12) . ?
C7 C8 1.3982(12) . ?
C7 C12 1.3996(12) . ?
C8 C9 1.3896(13) . ?
C8 H10 0.9500 . ?
C9 C10 1.3900(13) . ?
C9 H11 0.9500 . ?
C10 C11 1.3874(14) . ?
C11 C12 1.3914(13) . ?
C11 H12 0.9500 . ?
C12 H2 0.9500 . ?
C16 C15 1.3911(14) . ?
C16 C17 1.3923(15) . ?
C16 H7 0.9500 . ?
C17 C18 1.3933(14) . ?
C17 H1 0.9500 . ?
C18 C19 1.3908(13) . ?
C18 H6 0.9500 . ?
C19 C14 1.3970(12) . ?
C19 H19 0.9500 . ?
C15 C14 1.3972(12) . ?
C15 H8 0.9500 . ?
C14 C13 1.4930(12) . ?

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 N1 111.70(8) . . ?
C2 C1 H3 124.1 . . ?
N1 C1 H3 124.1 . . ?
C3 S1 C2 90.34(4) . . ?
C3 N1 C6 109.61(7) . . ?
C3 N1 C1 114.33(8) . . ?
C6 N1 C1 135.99(8) . . ?
C1 C2 S1 112.84(7) . . ?
C1 C2 H4 123.6 . . ?
S1 C2 H4 123.6 . . ?
N1 C3 C4 109.13(8) . . ?
N1 C3 S1 110.76(7) . . ?
C4 C3 S1 140.10(7) . . ?
C3 C4 C5 106.41(8) . . ?
C3 C4 H5 126.8 . . ?
C5 C4 H5 126.8 . . ?
C6 C5 C4 108.94(8) . . ?
C6 C5 C7 126.67(8) . . ?
C4 C5 C7 124.38(8) . . ?
N1 C6 C5 105.89(7) . . ?
N1 C6 C13 119.96(8) . . ?
C5 C6 C13 134.04(8) . . ?
C8 C7 C12 118.89(8) . . ?
C8 C7 C5 120.87(8) . . ?
C12 C7 C5 120.20(8) . . ?
C9 C8 C7 121.05(8) . . ?
C9 C8 H10 119.5 . . ?
C7 C8 H10 119.5 . . ?
C8 C9 C10 118.62(8) . . ?
C8 C9 H11 120.7 . . ?
C10 C9 H11 120.7 . . ?
C11 C10 C9 121.66(9) . . ?
C11 C10 Cl1 119.42(7) . . ?
C9 C10 Cl1 118.91(7) . . ?
C10 C11 C12 119.01(8) . . ?
C10 C11 H12 120.5 . . ?
C12 C11 H12 120.5 . . ?
C11 C12 C7 120.60(8) . . ?
C11 C12 H2 119.7 . . ?
C7 C12 H2 119.7 . . ?
C15 C16 C17 119.98(9) . . ?
C15 C16 H7 120.0 . . ?
C17 C16 H7 120.0 . . ?
C16 C17 C18 120.05(9) . . ?
C16 C17 H1 120.0 . . ?
C18 C17 H1 120.0 . . ?
C19 C18 C17 120.17(9) . . ?
C19 C18 H6 119.9 . . ?
C17 C18 H6 119.9 . . ?
C18 C19 C14 119.86(8) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
C16 C15 C14 120.05(9) . . ?
C16 C15 H8 120.0 . . ?
C14 C15 H8 120.0 . . ?
C19 C14 C15 119.86(8) . . ?
C19 C14 C13 121.49(8) . . ?
C15 C14 C13 118.64(8) . . ?
O1 C13 C6 121.15(8) . . ?
O1 C13 C14 119.81(8) . . ?
C6 C13 C14 119.04(8) . . ?

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
C2 C1 N1 C3 0.92(11) . . . . ?
C2 C1 N1 C6 177.64(9) . . . . ?
N1 C1 C2 S1 0.26(10) . . . . ?
C3 S1 C2 C1 -1.01(8) . . . . ?
C6 N1 C3 C4 0.82(10) . . . . ?
C1 N1 C3 C4 178.39(7) . . . . ?
C6 N1 C3 S1 -179.25(6) . . . . ?
C1 N1 C3 S1 -1.67(10) . . . . ?
C2 S1 C3 N1 1.48(7) . . . . ?
C2 S1 C3 C4 -178.61(11) . . . . ?
N1 C3 C4 C5 -0.22(10) . . . . ?
S1 C3 C4 C5 179.87(9) . . . . ?
C3 C4 C5 C6 -0.44(10) . . . . ?
C3 C4 C5 C7 178.49(8) . . . . ?
C3 N1 C6 C5 -1.06(9) . . . . ?
C1 N1 C6 C5 -177.89(9) . . . . ?
C3 N1 C6 C13 -177.71(8) . . . . ?
C1 N1 C6 C13 5.47(15) . . . . ?
C4 C5 C6 N1 0.92(9) . . . . ?
C7 C5 C6 N1 -177.98(8) . . . . ?
C4 C5 C6 C13 176.87(9) . . . . ?
C7 C5 C6 C13 -2.02(16) . . . . ?
C6 C5 C7 C8 51.52(13) . . . . ?
C4 C5 C7 C8 -127.22(10) . . . . ?
C6 C5 C7 C12 -126.14(10) . . . . ?
C4 C5 C7 C12 55.12(12) . . . . ?
C12 C7 C8 C9 4.11(13) . . . . ?
C5 C7 C8 C9 -173.58(8) . . . . ?
C7 C8 C9 C10 -1.05(14) . . . . ?
C8 C9 C10 C11 -2.50(14) . . . . ?
C8 C9 C10 Cl1 177.04(7) . . . . ?
C9 C10 C11 C12 2.87(14) . . . . ?
Cl1 C10 C11 C12 -176.67(7) . . . . ?
C10 C11 C12 C7 0.31(14) . . . . ?
C8 C7 C12 C11 -3.72(14) . . . . ?
C5 C7 C12 C11 173.99(8) . . . . ?
C15 C16 C17 C18 0.49(16) . . . . ?
C16 C17 C18 C19 -1.62(15) . . . . ?
C17 C18 C19 C14 0.82(14) . . . . ?
C17 C16 C15 C14 1.45(15) . . . . ?
C18 C19 C14 C15 1.12(14) . . . . ?
C18 C19 C14 C13 179.49(9) . . . . ?
C16 C15 C14 C19 -2.25(14) . . . . ?
C16 C15 C14 C13 179.33(9) . . . . ?
N1 C6 C13 O1 16.71(13) . . . . ?
C5 C6 C13 O1 -158.80(10) . . . . ?
N1 C6 C13 C14 -163.65(8) . . . . ?
C5 C6 C13 C14 20.84(15) . . . . ?
C19 C14 C13 O1 -135.24(9) . . . . ?
C15 C14 C13 O1 43.16(12) . . . . ?
C19 C14 C13 C6 45.12(12) . . . . ?
C15 C14 C13 C6 -136.48(9) . . . . ?

_refine_diff_density_max         0.524
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.058

