# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_4FSME_YEL
_database_code_depnum_ccdc_archive 'CCDC 2002966'
loop_
_audit_author_name
_audit_author_address
'Tafeenko Victor'
;Moscow State University (MSU)
Russia
;
_audit_update_record             
;
2020-05-10 deposited with the CCDC.	2020-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 Cl2 Cu1 F1 N3 O1 S1'
_chemical_formula_sum            'C16 H13 Cl2 Cu1 F1 N3 O1 S1'
_chemical_formula_weight         448.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   10.7555(3)
_cell_length_b                   11.7896(3)
_cell_length_c                   15.2935(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.304(2)
_cell_angle_gamma                90
_cell_volume                     1841.14(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3892
_cell_measurement_theta_min      4.5
_cell_measurement_theta_max      60.5

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .21
_exptl_crystal_size_mid          .14
_exptl_crystal_size_min          .12
_exptl_absorpt_coefficient_mu    5.581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.344
_exptl_absorpt_correction_T_max  0.715


_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            21916
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.443
_diffrn_reflns_theta_max         67.868
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3266
_reflns_number_gt                1976
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00057(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3266
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_restrained_S_all      0.921
_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
Cu1 Cu 0.72794(5) 0.74471(5) 0.65961(4) 0.0681(2) Uani 1 1 d . . . . .
S1 S 0.67548(8) 0.58034(9) 0.88353(6) 0.0675(3) Uani 1 1 d . . . . .
Cl1 Cl 0.92777(9) 0.71248(9) 0.68268(8) 0.0829(3) Uani 1 1 d . . . . .
Cl2 Cl 0.52996(8) 0.77713(9) 0.64387(7) 0.0723(3) Uani 1 1 d . . . . .
O1 O 0.3550(2) 0.4182(2) 0.60350(15) 0.0611(6) Uani 1 1 d . . . . .
F1 F 0.13037(19) 0.5969(2) 0.92292(15) 0.0949(8) Uani 1 1 d . . . . .
N1 N 0.8554(3) 0.4281(3) 0.6365(2) 0.0563(8) Uani 1 1 d . . . . .
N2 N 0.6840(2) 0.4860(2) 0.72463(16) 0.0463(6) Uani 1 1 d . . . . .
N3 N 0.4825(2) 0.5007(2) 0.73974(17) 0.0460(6) Uani 1 1 d . . . . .
C2 C 0.9801(3) 0.4256(3) 0.6371(3) 0.0670(10) Uani 1 1 d . . . . .
H2 H 1.0463 0.4538 0.6873 0.080 Uiso 1 1 calc R U . . .
C3 C 1.0093(4) 0.3814(3) 0.5637(3) 0.0679(11) Uani 1 1 d . . . . .
H3 H 1.0954 0.3788 0.5630 0.081 Uiso 1 1 calc R U . . .
C4 C 0.9092(4) 0.3407(3) 0.4908(3) 0.0703(11) Uani 1 1 d . . . . .
H4 H 0.9276 0.3102 0.4402 0.084 Uiso 1 1 calc R U . . .
C5 C 0.7818(3) 0.3445(3) 0.4917(2) 0.0599(9) Uani 1 1 d . . . . .
H5 H 0.7145 0.3169 0.4419 0.072 Uiso 1 1 calc R U . . .
C6 C 0.7544(3) 0.3899(3) 0.5672(2) 0.0484(8) Uani 1 1 d . . . . .
C7 C 0.6232(3) 0.3966(3) 0.5747(2) 0.0478(8) Uani 1 1 d . . . . .
H7 H 0.5545 0.3683 0.5261 0.057 Uiso 1 1 calc R U . . .
C8 C 0.5940(3) 0.4405(3) 0.6464(2) 0.0438(7) Uani 1 1 d . . . . .
C9 C 0.4597(3) 0.4478(3) 0.6551(2) 0.0476(8) Uani 1 1 d . . . . .
C10 C 0.6157(3) 0.5200(3) 0.7773(2) 0.0456(8) Uani 1 1 d . . . . .
C11 C 0.3871(3) 0.5261(3) 0.7849(2) 0.0473(8) Uani 1 1 d . . . . .
C12 C 0.3353(3) 0.4388(3) 0.8228(2) 0.0646(9) Uani 1 1 d . . . . .
H12 H 0.3600 0.3642 0.8174 0.078 Uiso 1 1 calc R U . . .
C13 C 0.2470(4) 0.4630(4) 0.8687(3) 0.0750(11) Uani 1 1 d . . . . .
H13 H 0.2112 0.4055 0.8949 0.090 Uiso 1 1 calc R U . . .
C14 C 0.2136(3) 0.5734(4) 0.8746(2) 0.0633(10) Uani 1 1 d . . . . .
C15 C 0.2594(3) 0.6595(4) 0.8361(2) 0.0692(11) Uani 1 1 d . . . . .
H15 H 0.2324 0.7336 0.8407 0.083 Uiso 1 1 calc R U . . .
C16 C 0.3478(3) 0.6354(3) 0.7892(2) 0.0640(10) Uani 1 1 d . . . . .
H16 H 0.3800 0.6933 0.7610 0.077 Uiso 1 1 calc R U . . .
C17 C 0.8480(3) 0.5809(3) 0.8976(2) 0.0646(10) Uani 1 1 d . . . . .
H17A H 0.8780 0.5043 0.8969 0.097 Uiso 1 1 calc R U . . .
H17B H 0.8947 0.6157 0.9554 0.097 Uiso 1 1 calc R U . . .
H17C H 0.8634 0.6229 0.8482 0.097 Uiso 1 1 calc R U . . .
H1 H 0.842(3) 0.460(3) 0.680(2) 0.048(10) Uiso 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
Cu1 Cl1 2.1005(10) . ?
Cu1 Cl2 2.1015(10) . ?
S1 C10 1.704(3) . ?
S1 C17 1.800(3) . ?
O1 C9 1.206(3) . ?
F1 C14 1.357(3) . ?
N1 C6 1.335(4) . ?
N1 C2 1.339(4) . ?
N1 H1 0.82(3) . ?
N2 C10 1.311(4) . ?
N2 C8 1.389(4) . ?
N3 C10 1.384(4) . ?
N3 C9 1.388(4) . ?
N3 C11 1.437(4) . ?
C2 C3 1.361(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.454(4) . ?
C7 C8 1.336(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.494(4) . ?
C11 C16 1.365(5) . ?
C11 C12 1.380(4) . ?
C12 C13 1.376(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.360(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.343(5) . ?
C15 C16 1.388(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
Cl1 Cu1 Cl2 177.06(5) . . ?
C10 S1 C17 100.48(15) . . ?
C6 N1 C2 124.1(3) . . ?
C6 N1 H1 119(2) . . ?
C2 N1 H1 116(2) . . ?
C10 N2 C8 105.9(2) . . ?
C10 N3 C9 108.5(2) . . ?
C10 N3 C11 124.7(2) . . ?
C9 N3 C11 126.7(2) . . ?
N1 C2 C3 119.6(3) . . ?
N1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 118.6(3) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
N1 C6 C5 117.3(3) . . ?
N1 C6 C7 119.1(3) . . ?
C5 C6 C7 123.6(3) . . ?
C8 C7 C6 124.8(3) . . ?
C8 C7 H7 117.6 . . ?
C6 C7 H7 117.6 . . ?
C7 C8 N2 125.2(3) . . ?
C7 C8 C9 125.3(3) . . ?
N2 C8 C9 109.4(2) . . ?
O1 C9 N3 126.6(3) . . ?
O1 C9 C8 130.9(3) . . ?
N3 C9 C8 102.5(3) . . ?
N2 C10 N3 113.6(3) . . ?
N2 C10 S1 126.7(2) . . ?
N3 C10 S1 119.7(2) . . ?
C16 C11 C12 120.8(3) . . ?
C16 C11 N3 119.9(3) . . ?
C12 C11 N3 119.3(3) . . ?
C13 C12 C11 119.6(4) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 118.1(3) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C15 C14 F1 118.7(4) . . ?
C15 C14 C13 123.6(3) . . ?
F1 C14 C13 117.7(3) . . ?
C14 C15 C16 118.5(4) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C11 C16 C15 119.4(3) . . ?
C11 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C6 N1 C2 C3 -0.3(6) . . . . ?
N1 C2 C3 C4 0.1(6) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C2 N1 C6 C5 0.2(5) . . . . ?
C2 N1 C6 C7 179.6(3) . . . . ?
C4 C5 C6 N1 0.0(5) . . . . ?
C4 C5 C6 C7 -179.4(3) . . . . ?
N1 C6 C7 C8 1.1(5) . . . . ?
C5 C6 C7 C8 -179.6(3) . . . . ?
C6 C7 C8 N2 -0.2(5) . . . . ?
C6 C7 C8 C9 -180.0(3) . . . . ?
C10 N2 C8 C7 179.6(3) . . . . ?
C10 N2 C8 C9 -0.6(3) . . . . ?
C10 N3 C9 O1 179.7(3) . . . . ?
C11 N3 C9 O1 3.2(5) . . . . ?
C10 N3 C9 C8 -1.2(3) . . . . ?
C11 N3 C9 C8 -177.7(3) . . . . ?
C7 C8 C9 O1 0.0(6) . . . . ?
N2 C8 C9 O1 -179.8(3) . . . . ?
C7 C8 C9 N3 -179.1(3) . . . . ?
N2 C8 C9 N3 1.1(3) . . . . ?
C8 N2 C10 N3 -0.1(4) . . . . ?
C8 N2 C10 S1 178.6(2) . . . . ?
C9 N3 C10 N2 0.9(4) . . . . ?
C11 N3 C10 N2 177.5(3) . . . . ?
C9 N3 C10 S1 -178.0(2) . . . . ?
C11 N3 C10 S1 -1.4(4) . . . . ?
C17 S1 C10 N2 -0.2(3) . . . . ?
C17 S1 C10 N3 178.5(3) . . . . ?
C10 N3 C11 C16 76.8(4) . . . . ?
C9 N3 C11 C16 -107.2(4) . . . . ?
C10 N3 C11 C12 -103.7(4) . . . . ?
C9 N3 C11 C12 72.3(4) . . . . ?
C16 C11 C12 C13 -2.6(5) . . . . ?
N3 C11 C12 C13 177.9(3) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C12 C13 C14 C15 1.9(6) . . . . ?
C12 C13 C14 F1 -177.5(3) . . . . ?
F1 C14 C15 C16 178.0(3) . . . . ?
C13 C14 C15 C16 -1.4(6) . . . . ?
C12 C11 C16 C15 3.1(5) . . . . ?
N3 C11 C16 C15 -177.5(3) . . . . ?
C14 C15 C16 C11 -1.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5 Cl2 0.93 2.77 3.638(4) 155.0 3_666
C12 H12 Cl1 0.93 2.90 3.709(4) 146.1 2_646
C13 H13 Cl2 0.93 2.90 3.654(4) 139.2 2_546
C15 H15 O1 0.93 2.62 3.519(4) 163.3 2_556
C16 H16 Cl2 0.93 2.93 3.782(4) 152.5 .
C17 H17A Cl2 0.96 2.99 3.934(4) 168.6 2_646
N1 H1 N2 0.82(3) 2.04(3) 2.691(4) 136(3) .

_refine_diff_density_max         0.542
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_shelx_2fse
_database_code_depnum_ccdc_archive 'CCDC 2002968'
loop_
_audit_author_name
_audit_author_address
'Tafeenko Victor'
;Moscow State University (MSU)
Russia
;
_audit_update_record             
;
2020-05-10 deposited with the CCDC.	2020-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 Cl Cu F N3 O S'
_chemical_formula_sum            'C16 H12 Cl Cu F N3 O S'
_chemical_formula_weight         412.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   28.4118(8)
_cell_length_b                   9.2731(3)
_cell_length_c                   13.7925(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.2410(10)
_cell_angle_gamma                90
_cell_volume                     3386.98(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3542
_cell_measurement_theta_min      5.6
_cell_measurement_theta_max      67.8

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_F_000             1664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .24
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .14
_exptl_absorpt_coefficient_mu    4.593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.449
_exptl_absorpt_correction_T_max  0.841


_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            17508
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_av_R_equivalents  0.0844
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.338
_diffrn_reflns_theta_max         68.805
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3095
_reflns_number_gt                2031
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0868P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00142(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3095
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1460
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.000
_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
Cu1 Cu 0.48694(3) 0.51600(6) 0.63069(5) 0.0498(3) Uani 1 1 d . . . . .
Cl1 Cl 0.43286(4) 0.34125(10) 0.59893(9) 0.0550(3) Uani 1 1 d . . . . .
S1 S 0.61998(5) 0.37336(12) 0.67024(11) 0.0616(4) Uani 1 1 d . . . . .
O1 O 0.62671(12) 0.9019(3) 0.6476(3) 0.0614(9) Uani 1 1 d . . . . .
N1 N 0.44660(14) 0.7107(3) 0.6139(3) 0.0454(8) Uani 1 1 d . . . . .
N2 N 0.55260(13) 0.5965(3) 0.6459(2) 0.0434(8) Uani 1 1 d . . . . .
N3 N 0.63256(14) 0.6541(3) 0.6664(3) 0.0472(9) Uani 1 1 d . . . . .
F1 F 0.70858(14) 0.6086(6) 0.8531(3) 0.1191(15) Uani 1 1 d . . . . .
C2 C 0.39777(18) 0.7073(5) 0.5990(4) 0.0527(11) Uani 1 1 d . . . . .
H2 H 0.382891 0.617818 0.598468 0.063 Uiso 1 1 calc R U . . .
C3 C 0.36812(19) 0.8268(5) 0.5844(4) 0.0602(13) Uani 1 1 d . . . . .
H3 H 0.334016 0.818797 0.574083 0.072 Uiso 1 1 calc R U . . .
C4 C 0.3899(2) 0.9596(5) 0.5853(4) 0.0656(14) Uani 1 1 d . . . . .
H4 H 0.370545 1.043089 0.575262 0.079 Uiso 1 1 calc R U . . .
C5 C 0.4402(2) 0.9677(5) 0.6010(4) 0.0568(12) Uani 1 1 d . . . . .
H5 H 0.455540 1.056673 0.602556 0.068 Uiso 1 1 calc R U . . .
C6 C 0.46796(17) 0.8409(4) 0.6146(3) 0.0438(10) Uani 1 1 d . . . . .
C7 C 0.52095(17) 0.8499(4) 0.6279(3) 0.0470(11) Uani 1 1 d . . . . .
H7 H 0.532733 0.943539 0.628153 0.056 Uiso 1 1 calc R U . . .
C8 C 0.55595(16) 0.7477(4) 0.6398(3) 0.0416(9) Uani 1 1 d . . . . .
C9 C 0.60812(17) 0.7861(4) 0.6503(3) 0.0482(11) Uani 1 1 d . . . . .
C10 C 0.59787(18) 0.5476(4) 0.6601(3) 0.0465(10) Uani 1 1 d . . . . .
C11 C 0.68382(17) 0.6308(5) 0.6732(4) 0.0540(12) Uani 1 1 d . . . . .
C12 C 0.6959(2) 0.6287(6) 0.5847(4) 0.0716(15) Uani 1 1 d . . . . .
H12 H 0.671005 0.642995 0.519523 0.086 Uiso 1 1 calc R U . . .
C13 C 0.7452(2) 0.6052(7) 0.5941(5) 0.0851(17) Uani 1 1 d . . . . .
H13 H 0.753801 0.605606 0.535182 0.102 Uiso 1 1 calc R U . . .
C14 C 0.7817(2) 0.5812(7) 0.6900(5) 0.0854(18) Uani 1 1 d . . . . .
H14 H 0.814709 0.562729 0.695453 0.103 Uiso 1 1 calc R U . . .
C15 C 0.7699(2) 0.5842(8) 0.7773(5) 0.0878(19) Uani 1 1 d . . . . .
H15 H 0.794708 0.569534 0.842465 0.105 Uiso 1 1 calc R U . . .
C16 C 0.7212(2) 0.6089(6) 0.7675(4) 0.0713(15) Uani 1 1 d . . . . .
C17 C 0.5659(2) 0.2631(5) 0.6494(4) 0.0657(14) Uani 1 1 d . . . . .
H17A H 0.553521 0.277894 0.704773 0.099 Uiso 1 1 calc R U . . .
H17B H 0.574972 0.163616 0.647848 0.099 Uiso 1 1 calc R U . . .
H17C H 0.540111 0.288313 0.584281 0.099 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
Cu1 N2 1.949(4) . ?
Cu1 N1 2.106(3) . ?
Cu1 Cl1 2.1658(12) . ?
S1 C10 1.721(4) . ?
S1 C17 1.780(5) . ?
O1 C9 1.203(5) . ?
N1 C2 1.327(6) . ?
N1 C6 1.349(5) . ?
N2 C10 1.310(5) . ?
N2 C8 1.410(5) . ?
N3 C10 1.376(6) . ?
N3 C9 1.385(5) . ?
N3 C11 1.441(6) . ?
F1 C16 1.353(6) . ?
C2 C3 1.362(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.452(6) . ?
C7 C8 1.340(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.480(6) . ?
C11 C16 1.365(7) . ?
C11 C12 1.382(7) . ?
C12 C13 1.376(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.362(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.359(8) . ?
C15 H15 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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 Cu1 N1 98.33(14) . . ?
N2 Cu1 Cl1 152.83(10) . . ?
N1 Cu1 Cl1 107.54(11) . . ?
C10 S1 C17 105.0(2) . . ?
C2 N1 C6 117.7(3) . . ?
C2 N1 Cu1 119.6(3) . . ?
C6 N1 Cu1 122.7(3) . . ?
C10 N2 C8 105.6(4) . . ?
C10 N2 Cu1 137.2(3) . . ?
C8 N2 Cu1 117.2(3) . . ?
C10 N3 C9 108.5(4) . . ?
C10 N3 C11 125.5(3) . . ?
C9 N3 C11 125.4(3) . . ?
N1 C2 C3 124.0(4) . . ?
N1 C2 H2 118.0 . . ?
C3 C2 H2 118.0 . . ?
C2 C3 C4 118.4(5) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 119.0(4) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
N1 C6 C5 121.6(4) . . ?
N1 C6 C7 119.7(3) . . ?
C5 C6 C7 118.7(4) . . ?
C8 C7 C6 131.6(4) . . ?
C8 C7 H7 114.2 . . ?
C6 C7 H7 114.2 . . ?
C7 C8 N2 130.4(4) . . ?
C7 C8 C9 120.9(4) . . ?
N2 C8 C9 108.7(3) . . ?
O1 C9 N3 126.4(4) . . ?
O1 C9 C8 130.3(4) . . ?
N3 C9 C8 103.3(3) . . ?
N2 C10 N3 113.8(4) . . ?
N2 C10 S1 130.3(3) . . ?
N3 C10 S1 115.9(3) . . ?
C16 C11 C12 118.9(5) . . ?
C16 C11 N3 120.2(5) . . ?
C12 C11 N3 120.9(4) . . ?
C13 C12 C11 119.2(5) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 120.3(6) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.5(6) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 118.9(5) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
F1 C16 C15 119.7(5) . . ?
F1 C16 C11 118.1(5) . . ?
C15 C16 C11 122.1(5) . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C6 N1 C2 C3 0.0(7) . . . . ?
Cu1 N1 C2 C3 -178.1(4) . . . . ?
N1 C2 C3 C4 -0.1(8) . . . . ?
C2 C3 C4 C5 -0.2(8) . . . . ?
C3 C4 C5 C6 0.7(8) . . . . ?
C2 N1 C6 C5 0.5(6) . . . . ?
Cu1 N1 C6 C5 178.5(3) . . . . ?
C2 N1 C6 C7 -178.4(4) . . . . ?
Cu1 N1 C6 C7 -0.3(6) . . . . ?
C4 C5 C6 N1 -0.8(7) . . . . ?
C4 C5 C6 C7 178.0(4) . . . . ?
N1 C6 C7 C8 0.6(7) . . . . ?
C5 C6 C7 C8 -178.2(5) . . . . ?
C6 C7 C8 N2 -1.8(8) . . . . ?
C6 C7 C8 C9 179.0(4) . . . . ?
C10 N2 C8 C7 -178.5(4) . . . . ?
Cu1 N2 C8 C7 2.2(6) . . . . ?
C10 N2 C8 C9 0.8(4) . . . . ?
Cu1 N2 C8 C9 -178.5(2) . . . . ?
C10 N3 C9 O1 -177.8(4) . . . . ?
C11 N3 C9 O1 -6.1(7) . . . . ?
C10 N3 C9 C8 3.1(4) . . . . ?
C11 N3 C9 C8 174.8(4) . . . . ?
C7 C8 C9 O1 -2.1(7) . . . . ?
N2 C8 C9 O1 178.5(4) . . . . ?
C7 C8 C9 N3 176.9(4) . . . . ?
N2 C8 C9 N3 -2.4(4) . . . . ?
C8 N2 C10 N3 1.3(5) . . . . ?
Cu1 N2 C10 N3 -179.7(3) . . . . ?
C8 N2 C10 S1 -177.9(3) . . . . ?
Cu1 N2 C10 S1 1.2(7) . . . . ?
C9 N3 C10 N2 -3.0(5) . . . . ?
C11 N3 C10 N2 -174.6(4) . . . . ?
C9 N3 C10 S1 176.3(3) . . . . ?
C11 N3 C10 S1 4.6(6) . . . . ?
C17 S1 C10 N2 3.4(5) . . . . ?
C17 S1 C10 N3 -175.7(3) . . . . ?
C10 N3 C11 C16 -86.3(6) . . . . ?
C9 N3 C11 C16 103.5(6) . . . . ?
C10 N3 C11 C12 93.1(6) . . . . ?
C9 N3 C11 C12 -77.2(6) . . . . ?
C16 C11 C12 C13 -0.2(8) . . . . ?
N3 C11 C12 C13 -179.6(5) . . . . ?
C11 C12 C13 C14 1.3(10) . . . . ?
C12 C13 C14 C15 -1.8(11) . . . . ?
C13 C14 C15 C16 1.1(11) . . . . ?
C14 C15 C16 F1 178.3(6) . . . . ?
C14 C15 C16 C11 0.1(11) . . . . ?
C12 C11 C16 F1 -178.8(5) . . . . ?
N3 C11 C16 F1 0.6(7) . . . . ?
C12 C11 C16 C15 -0.5(9) . . . . ?
N3 C11 C16 C15 178.9(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 Cl1 0.93 2.93 3.538(4) 124.2 .
C5 H5 Cl1 0.93 2.71 3.469(4) 139.1 1_565
C12 H12 Cl1 0.93 2.81 3.628(6) 147.1 5_666
C17 H17A Cl1 0.96 2.66 3.534(5) 151.9 2_656

_refine_diff_density_max         1.031
_refine_diff_density_min         -1.015
_refine_diff_density_rms         0.348

####################################################################### 
# 
# 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_3sfsmek
_database_code_depnum_ccdc_archive 'CCDC 2002969'
loop_
_audit_author_name
_audit_author_address
'Tafeenko Victor'
;Moscow State University (MSU)
Russia
;
_audit_update_record             
;
2020-05-10 deposited with the CCDC.	2020-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 Cl2 Cu F N3 O S'
_chemical_formula_sum            'C16 H13 Cl2 Cu F N3 O S'
_chemical_formula_weight         448.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.5590(6)
_cell_length_b                   11.5979(7)
_cell_length_c                   15.9749(12)
_cell_angle_alpha                90
_cell_angle_beta                 72.947(6)
_cell_angle_gamma                90
_cell_volume                     1870.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3843
_cell_measurement_theta_min      4.5
_cell_measurement_theta_max      65

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .19
_exptl_crystal_size_mid          .13
_exptl_crystal_size_min          .11
_exptl_absorpt_coefficient_mu    5.494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.343
_exptl_absorpt_correction_T_max  0.640


_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            19780
_diffrn_reflns_av_unetI/netI     0.0772
_diffrn_reflns_av_R_equivalents  0.1023
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.380
_diffrn_reflns_theta_max         71.537
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3580
_reflns_number_gt                1496
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0851P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3580
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1280
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1586
_refine_ls_wR_factor_gt          0.1362
_refine_ls_goodness_of_fit_ref   0.822
_refine_ls_restrained_S_all      0.822
_refine_ls_shift/su_max          0.000
_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
Cu1 Cu 0.94262(9) 0.24482(7) 0.36220(5) 0.1025(4) Uani 1 1 d . . . . .
S1 S 0.14770(13) 0.40783(13) 0.11873(9) 0.0920(5) Uani 1 1 d . . . . .
Cl1 Cl 1.12883(17) 0.20730(16) 0.37470(10) 0.1179(6) Uani 1 1 d . . . . .
Cl2 Cl 0.75726(18) 0.28104(15) 0.34576(18) 0.1587(9) Uani 1 1 d . . . . .
O1 O 0.2296(3) 0.5639(4) 0.3886(3) 0.1005(12) Uani 1 1 d . . . . .
N1 N -0.2475(4) 0.5691(4) 0.3513(3) 0.0759(12) Uani 1 1 d . . . . .
N2 N 0.0036(3) 0.5051(3) 0.2690(2) 0.0651(10) Uani 1 1 d . . . . .
N3 N 0.2215(4) 0.4883(3) 0.2556(2) 0.0702(10) Uani 1 1 d . . . . .
C2 C -0.3704(5) 0.5766(5) 0.3490(4) 0.0912(16) Uani 1 1 d . . . . .
H2 H -0.3919 0.5533 0.2991 0.109 Uiso 1 1 calc R U . . .
C3 C -0.4666(5) 0.6185(5) 0.4190(4) 0.0872(15) Uani 1 1 d . . . . .
H3 H -0.5545 0.6222 0.4187 0.105 Uiso 1 1 calc R U . . .
C4 C -0.4293(5) 0.6550(5) 0.4902(4) 0.0897(16) Uani 1 1 d . . . . .
H4 H -0.4929 0.6853 0.5385 0.108 Uiso 1 1 calc R U . . .
C5 C -0.3024(5) 0.6478(4) 0.4913(3) 0.0800(14) Uani 1 1 d . . . . .
H5 H -0.2790 0.6727 0.5401 0.096 Uiso 1 1 calc R U . . .
C6 C -0.2068(4) 0.6031(4) 0.4195(3) 0.0640(11) Uani 1 1 d . . . . .
C7 C -0.0687(4) 0.5926(4) 0.4146(3) 0.0701(12) Uani 1 1 d . . . . .
H7 H -0.0429 0.6182 0.4623 0.084 Uiso 1 1 calc R U . . .
C8 C 0.0267(4) 0.5480(4) 0.3452(3) 0.0646(11) Uani 1 1 d . . . . .
C9 C 0.1679(5) 0.5382(4) 0.3382(3) 0.0729(13) Uani 1 1 d . . . . .
C10 C 0.1180(4) 0.4714(4) 0.2199(3) 0.0643(11) Uani 1 1 d . . . . .
C17 C -0.0182(5) 0.3991(5) 0.1117(3) 0.0972(17) Uani 1 1 d . . . . .
H17A H -0.0710 0.3534 0.1593 0.146 Uiso 1 1 calc R U . . .
H17B H -0.0175 0.3641 0.0572 0.146 Uiso 1 1 calc R U . . .
H17C H -0.0551 0.4752 0.1150 0.146 Uiso 1 1 calc R U . . .
H H -0.184(5) 0.542(4) 0.311(3) 0.065(14) Uiso 1 1 d . . . . .
C11 C 0.3560(4) 0.4606(4) 0.2147(3) 0.0733(13) Uani 0.337(6) 1 d . . P A 1
C12 C 0.4131(6) 0.3679(5) 0.2414(4) 0.0952(16) Uani 0.337(6) 1 d . . P A 1
H12 H 0.3654 0.3216 0.2875 0.114 Uiso 0.337(6) 1 calc R U P A 1
C13 C 0.5435(8) 0.3448(7) 0.1981(6) 0.118(2) Uani 0.337(6) 1 d . . P A 1
C14 C 0.6173(6) 0.4083(9) 0.1320(5) 0.116(2) Uani 0.337(6) 1 d . . P A 1
H14 H 0.7049 0.3898 0.1027 0.139 Uiso 0.337(6) 1 calc R U P A 1
C15 C 0.5573(7) 0.4991(8) 0.1112(5) 0.128(2) Uani 0.337(6) 1 d . . P A 1
H15 H 0.6077 0.5467 0.0671 0.153 Uiso 0.337(6) 1 calc R U P A 1
C16 C 0.4278(5) 0.5295(5) 0.1486(4) 0.1069(19) Uani 0.337(6) 1 d . . P A 1
H16 H 0.3908 0.5937 0.1300 0.128 Uiso 0.337(6) 1 calc R U P A 1
F1 F 0.5887(13) 0.2499(17) 0.2202(10) 0.191(3) Uani 0.337(6) 1 d . . P A 1
C111 C 0.3560(4) 0.4606(4) 0.2147(3) 0.0733(13) Uani 0.663(6) 1 d . . P A 2
C121 C 0.4131(6) 0.3679(5) 0.2414(4) 0.0952(16) Uani 0.663(6) 1 d . . P A 2
H121 H 0.3654 0.3216 0.2875 0.114 Uiso 0.663(6) 1 calc R U P A 2
C131 C 0.5435(8) 0.3448(7) 0.1981(6) 0.118(2) Uani 0.663(6) 1 d . . P A 2
H131 H 0.5827 0.2812 0.2158 0.142 Uiso 0.663(6) 1 calc R U P A 2
C141 C 0.6173(6) 0.4083(9) 0.1320(5) 0.116(2) Uani 0.663(6) 1 d . . P A 2
H141 H 0.7049 0.3898 0.1027 0.139 Uiso 0.663(6) 1 calc R U P A 2
C151 C 0.5573(7) 0.4991(8) 0.1112(5) 0.128(2) Uani 0.663(6) 1 d . . P A 2
C161 C 0.4278(5) 0.5295(5) 0.1486(4) 0.1069(19) Uani 0.663(6) 1 d . . P A 2
H161 H 0.3908 0.5937 0.1300 0.128 Uiso 0.663(6) 1 calc R U P A 2
F11 F 0.6262(7) 0.5665(8) 0.0471(5) 0.191(3) Uani 0.663(6) 1 d . . P A 2


_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
Cu1 Cl1 2.0798(19) . ?
Cu1 Cl2 2.092(2) . ?
S1 C10 1.719(5) . ?
S1 C17 1.791(5) . ?
O1 C9 1.212(6) . ?
N1 C2 1.312(6) . ?
N1 C6 1.343(6) . ?
N1 H 0.84(4) . ?
N2 C10 1.293(5) . ?
N2 C8 1.401(6) . ?
N3 C10 1.388(6) . ?
N3 C9 1.399(6) . ?
N3 C111 1.415(6) . ?
N3 C11 1.415(6) . ?
C2 C3 1.361(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.348(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.442(6) . ?
C7 C8 1.363(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.467(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C11 C12 1.360(7) . ?
C11 C16 1.364(7) . ?
C12 C13 1.375(9) . ?
C12 H12 0.9300 . ?
C13 F1 1.290(17) . ?
C13 C14 1.334(9) . ?
C14 C15 1.321(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.368(9) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C111 C121 1.360(7) . ?
C111 C161 1.364(7) . ?
C121 C131 1.375(9) . ?
C121 H121 0.9300 . ?
C131 C141 1.334(9) . ?
C131 H131 0.9300 . ?
C141 C151 1.321(10) . ?
C141 H141 0.9300 . ?
C151 F11 1.324(9) . ?
C151 C161 1.368(9) . ?
C161 H161 0.9300 . ?

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
Cl1 Cu1 Cl2 178.31(10) . . ?
C10 S1 C17 99.8(2) . . ?
C2 N1 C6 123.9(4) . . ?
C2 N1 H 125(3) . . ?
C6 N1 H 111(3) . . ?
C10 N2 C8 105.4(4) . . ?
C10 N3 C9 107.3(4) . . ?
C10 N3 C111 125.7(4) . . ?
C9 N3 C111 127.1(4) . . ?
C10 N3 C11 125.7(4) . . ?
C9 N3 C11 127.1(4) . . ?
N1 C2 C3 120.5(5) . . ?
N1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 117.6(5) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 H3 121.2 . . ?
C5 C4 C3 121.3(5) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.8(5) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
N1 C6 C5 116.9(4) . . ?
N1 C6 C7 119.4(4) . . ?
C5 C6 C7 123.7(5) . . ?
C8 C7 C6 124.8(4) . . ?
C8 C7 H7 117.6 . . ?
C6 C7 H7 117.6 . . ?
C7 C8 N2 124.5(4) . . ?
C7 C8 C9 125.7(4) . . ?
N2 C8 C9 109.8(4) . . ?
O1 C9 N3 125.5(4) . . ?
O1 C9 C8 131.5(5) . . ?
N3 C9 C8 103.0(4) . . ?
N2 C10 N3 114.6(4) . . ?
N2 C10 S1 125.5(4) . . ?
N3 C10 S1 119.9(3) . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C11 C16 120.6(5) . . ?
C12 C11 N3 120.8(5) . . ?
C16 C11 N3 118.6(5) . . ?
C11 C12 C13 117.8(6) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
F1 C13 C14 120.7(10) . . ?
F1 C13 C12 115.1(10) . . ?
C14 C13 C12 123.9(7) . . ?
C15 C14 C13 115.3(6) . . ?
C15 C14 H14 122.4 . . ?
C13 C14 H14 122.4 . . ?
C14 C15 C16 125.9(7) . . ?
C14 C15 H15 117.0 . . ?
C16 C15 H15 117.0 . . ?
C11 C16 C15 116.4(6) . . ?
C11 C16 H16 121.8 . . ?
C15 C16 H16 121.8 . . ?
C121 C111 C161 120.6(5) . . ?
C121 C111 N3 120.8(5) . . ?
C161 C111 N3 118.6(5) . . ?
C111 C121 C131 117.8(6) . . ?
C111 C121 H121 121.1 . . ?
C131 C121 H121 121.1 . . ?
C141 C131 C121 123.9(7) . . ?
C141 C131 H131 118.0 . . ?
C121 C131 H131 118.0 . . ?
C151 C141 C131 115.3(6) . . ?
C151 C141 H141 122.4 . . ?
C131 C141 H141 122.4 . . ?
C141 C151 F11 118.1(8) . . ?
C141 C151 C161 125.9(7) . . ?
F11 C151 C161 115.9(8) . . ?
C111 C161 C151 116.4(6) . . ?
C111 C161 H161 121.8 . . ?
C151 C161 H161 121.8 . . ?

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
C6 N1 C2 C3 -1.6(8) . . . . ?
N1 C2 C3 C4 1.8(8) . . . . ?
C2 C3 C4 C5 -1.2(8) . . . . ?
C3 C4 C5 C6 0.2(8) . . . . ?
C2 N1 C6 C5 0.6(7) . . . . ?
C2 N1 C6 C7 -179.0(5) . . . . ?
C4 C5 C6 N1 0.1(7) . . . . ?
C4 C5 C6 C7 179.7(5) . . . . ?
N1 C6 C7 C8 -1.2(7) . . . . ?
C5 C6 C7 C8 179.3(4) . . . . ?
C6 C7 C8 N2 -0.6(7) . . . . ?
C6 C7 C8 C9 179.0(4) . . . . ?
C10 N2 C8 C7 179.9(4) . . . . ?
C10 N2 C8 C9 0.3(5) . . . . ?
C10 N3 C9 O1 179.3(5) . . . . ?
C111 N3 C9 O1 -1.2(8) . . . . ?
C11 N3 C9 O1 -1.2(8) . . . . ?
C10 N3 C9 C8 -0.2(5) . . . . ?
C111 N3 C9 C8 179.3(4) . . . . ?
C11 N3 C9 C8 179.3(4) . . . . ?
C7 C8 C9 O1 0.9(9) . . . . ?
N2 C8 C9 O1 -179.5(5) . . . . ?
C7 C8 C9 N3 -179.6(4) . . . . ?
N2 C8 C9 N3 0.0(5) . . . . ?
C8 N2 C10 N3 -0.5(5) . . . . ?
C8 N2 C10 S1 178.3(3) . . . . ?
C9 N3 C10 N2 0.5(5) . . . . ?
C111 N3 C10 N2 -179.0(4) . . . . ?
C11 N3 C10 N2 -179.0(4) . . . . ?
C9 N3 C10 S1 -178.4(3) . . . . ?
C111 N3 C10 S1 2.1(6) . . . . ?
C11 N3 C10 S1 2.1(6) . . . . ?
C17 S1 C10 N2 -3.0(5) . . . . ?
C17 S1 C10 N3 175.7(4) . . . . ?
C10 N3 C11 C12 -106.1(6) . . . . ?
C9 N3 C11 C12 74.5(6) . . . . ?
C10 N3 C11 C16 74.6(6) . . . . ?
C9 N3 C11 C16 -104.8(6) . . . . ?
C16 C11 C12 C13 -1.7(8) . . . . ?
N3 C11 C12 C13 179.1(5) . . . . ?
C11 C12 C13 F1 -173.5(10) . . . . ?
C11 C12 C13 C14 0.5(10) . . . . ?
F1 C13 C14 C15 175.2(12) . . . . ?
C12 C13 C14 C15 1.6(11) . . . . ?
C13 C14 C15 C16 -2.8(12) . . . . ?
C12 C11 C16 C15 0.7(9) . . . . ?
N3 C11 C16 C15 180.0(5) . . . . ?
C14 C15 C16 C11 1.6(11) . . . . ?
C10 N3 C111 C121 -106.1(6) . . . . ?
C9 N3 C111 C121 74.5(6) . . . . ?
C10 N3 C111 C161 74.6(6) . . . . ?
C9 N3 C111 C161 -104.8(6) . . . . ?
C161 C111 C121 C131 -1.7(8) . . . . ?
N3 C111 C121 C131 179.1(5) . . . . ?
C111 C121 C131 C141 0.5(10) . . . . ?
C121 C131 C141 C151 1.6(11) . . . . ?
C131 C141 C151 F11 178.9(7) . . . . ?
C131 C141 C151 C161 -2.8(12) . . . . ?
C121 C111 C161 C151 0.7(9) . . . . ?
N3 C111 C161 C151 180.0(5) . . . . ?
C141 C151 C161 C111 1.6(11) . . . . ?
F11 C151 C161 C111 -180.0(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 O1 0.93 2.55 3.440(7) 159.2 1_455
C5 H5 Cl1 0.93 2.75 3.615(6) 154.8 3_666
C17 H17B Cl1 0.96 2.99 3.850(5) 150.2 4_465
C17 H17C Cl1 0.96 2.79 3.747(6) 172.2 2_655
N1 H N2 0.84(4) 1.94(5) 2.695(5) 148(4) .
C12 H12 Cl1 0.93 2.81 3.641(6) 149.4 1_455
C16 H16 Cl2 0.93 2.64 3.498(6) 154.0 2_655
C121 H121 Cl1 0.93 2.81 3.641(6) 149.4 1_455
C161 H161 Cl2 0.93 2.64 3.498(6) 154.0 2_655

_refine_diff_density_max         0.481
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_4fseme_needle
_database_code_depnum_ccdc_archive 'CCDC 2002967'
loop_
_audit_author_name
_audit_author_address
'Tafeenko Victor'
;Moscow State University (MSU)
Russia
;
_audit_update_record             
;
2020-05-10 deposited with the CCDC.	2020-09-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 Cl2 Cu F N3 O S'
_chemical_formula_sum            'C16 H12 Cl2 Cu F N3 O S'
_chemical_formula_weight         447.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   46.8170(10)
_cell_length_b                   20.7265(5)
_cell_length_c                   7.27860(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7062.8(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1595
_cell_measurement_theta_min      4.5
_cell_measurement_theta_max      65.5

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_F_000             3600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .23
_exptl_crystal_size_mid          .17
_exptl_crystal_size_min          .14
_exptl_absorpt_coefficient_mu    5.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.449
_exptl_absorpt_correction_T_max  0.841


_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            33441
_diffrn_reflns_av_unetI/netI     0.0840
_diffrn_reflns_av_R_equivalents  0.1099
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       55
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.777
_diffrn_reflns_theta_max         66.904
_diffrn_reflns_theta_full        66.904
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.949
_reflns_number_total             2989
_reflns_number_gt                2086
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_max     0.895
_reflns_Friedel_fraction_full    0.895

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 693 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2989
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_restrained_S_all      0.902
_refine_ls_shift/su_max          0.000
_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
Cu1 Cu 0.42822(2) 0.25176(5) 0.71541(16) 0.0325(3) Uani 1 1 d . . . . .
Cl1 Cl 0.43965(5) 0.20527(8) 0.4499(3) 0.0447(5) Uani 1 1 d . . . . .
Cl2 Cl 0.44602(4) 0.17404(9) 0.8907(3) 0.0442(5) Uani 1 1 d . . . . .
S1 S 0.48248(5) 0.35555(9) 0.4554(3) 0.0469(5) Uani 1 1 d . . . . .
F1 F 0.47584(13) 0.5541(2) -0.2017(7) 0.0689(16) Uani 1 1 d . . . . .
O1 O 0.38637(12) 0.4487(3) 0.3563(8) 0.0486(15) Uani 1 1 d . . . . .
N1 N 0.39927(13) 0.2858(3) 0.9056(8) 0.0289(14) Uani 1 1 d . . . . .
N2 N 0.42920(14) 0.3404(3) 0.6060(8) 0.0313(15) Uani 1 1 d . . . . .
N3 N 0.43294(13) 0.4101(3) 0.3709(9) 0.0341(16) Uani 1 1 d . . . . .
C2 C 0.39920(18) 0.2623(3) 1.0778(10) 0.0347(19) Uani 1 1 d . . . . .
H2 H 0.4142 0.2357 1.1134 0.042 Uiso 1 1 calc R U . . .
C3 C 0.37827(18) 0.2754(3) 1.2037(13) 0.042(2) Uani 1 1 d . . . . .
H3 H 0.3793 0.2587 1.3221 0.051 Uiso 1 1 calc R U . . .
C4 C 0.35573(19) 0.3136(4) 1.1525(12) 0.044(2) Uani 1 1 d . . . . .
H4 H 0.3410 0.3226 1.2343 0.053 Uiso 1 1 calc R U . . .
C5 C 0.35545(17) 0.3385(3) 0.9764(12) 0.040(2) Uani 1 1 d . . . . .
H5 H 0.3402 0.3641 0.9385 0.048 Uiso 1 1 calc R U . . .
C6 C 0.37758(16) 0.3257(3) 0.8557(11) 0.0303(18) Uani 1 1 d . . . . .
C7 C 0.37911(16) 0.3597(3) 0.6823(11) 0.0335(18) Uani 1 1 d . . . . .
H7 H 0.3622 0.3772 0.6383 0.040 Uiso 1 1 calc R U . . .
C8 C 0.40219(17) 0.3684(3) 0.5796(10) 0.0309(18) Uani 1 1 d . . . . .
C9 C 0.40420(17) 0.4142(3) 0.4209(10) 0.034(2) Uani 1 1 d . . . . .
C10 C 0.44686(16) 0.3662(3) 0.4823(11) 0.0349(18) Uani 1 1 d . . . . .
C11 C 0.44536(15) 0.4471(3) 0.2244(11) 0.0325(17) Uani 1 1 d . . . . .
C12 C 0.45516(18) 0.5087(3) 0.2558(11) 0.041(2) Uani 1 1 d . . . . .
H12 H 0.4547 0.5259 0.3739 0.050 Uiso 1 1 calc R U . . .
C13 C 0.4655(2) 0.5447(4) 0.1136(12) 0.045(2) Uani 1 1 d . . . . .
H13 H 0.4722 0.5864 0.1336 0.054 Uiso 1 1 calc R U . . .
C14 C 0.46593(18) 0.5186(4) -0.0581(13) 0.043(2) Uani 1 1 d . . . . .
C15 C 0.4567(2) 0.4578(4) -0.0929(12) 0.057(3) Uani 1 1 d . . . . .
H15 H 0.4576 0.4410 -0.2112 0.068 Uiso 1 1 calc R U . . .
C16 C 0.4462(2) 0.4217(4) 0.0493(13) 0.055(3) Uani 1 1 d . . . . .
H16 H 0.4396 0.3801 0.0278 0.066 Uiso 1 1 calc R U . . .
C17 C 0.49178(18) 0.3073(4) 0.6525(13) 0.054(2) Uani 1 1 d . . . . .
H17A H 0.4814 0.3223 0.7578 0.081 Uiso 1 1 calc R U . . .
H17B H 0.5119 0.3108 0.6755 0.081 Uiso 1 1 calc R U . . .
H17C H 0.4870 0.2630 0.6291 0.081 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
Cu1 N2 2.002(6) . ?
Cu1 N1 2.062(6) . ?
Cu1 Cl2 2.218(2) . ?
Cu1 Cl1 2.225(2) . ?
S1 C10 1.693(8) . ?
S1 C17 1.802(9) . ?
F1 C14 1.360(9) . ?
O1 C9 1.195(8) . ?
N1 C2 1.344(9) . ?
N1 C6 1.359(9) . ?
N2 C10 1.334(9) . ?
N2 C8 1.404(9) . ?
N3 C10 1.382(9) . ?
N3 C9 1.396(9) . ?
N3 C11 1.437(9) . ?
C2 C3 1.369(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.448(10) . ?
C7 C8 1.326(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.499(10) . ?
C11 C12 1.376(10) . ?
C11 C16 1.380(11) . ?
C12 C13 1.365(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.362(12) . ?
C13 H13 0.9300 . ?
C14 C15 1.354(11) . ?
C15 C16 1.369(12) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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 Cu1 N1 88.2(2) . . ?
N2 Cu1 Cl2 152.4(2) . . ?
N1 Cu1 Cl2 96.24(17) . . ?
N2 Cu1 Cl1 92.65(18) . . ?
N1 Cu1 Cl1 152.82(18) . . ?
Cl2 Cu1 Cl1 95.44(8) . . ?
C10 S1 C17 102.6(4) . . ?
C2 N1 C6 117.9(7) . . ?
C2 N1 Cu1 120.3(5) . . ?
C6 N1 Cu1 121.3(5) . . ?
C10 N2 C8 107.5(6) . . ?
C10 N2 Cu1 130.6(5) . . ?
C8 N2 Cu1 114.4(5) . . ?
C10 N3 C9 110.0(6) . . ?
C10 N3 C11 126.6(6) . . ?
C9 N3 C11 123.4(6) . . ?
N1 C2 C3 123.6(8) . . ?
N1 C2 H2 118.2 . . ?
C3 C2 H2 118.2 . . ?
C2 C3 C4 118.9(8) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 118.4(8) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 120.7(7) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
N1 C6 C5 120.4(7) . . ?
N1 C6 C7 119.5(7) . . ?
C5 C6 C7 119.8(7) . . ?
C8 C7 C6 126.7(7) . . ?
C8 C7 H7 116.6 . . ?
C6 C7 H7 116.6 . . ?
C7 C8 N2 126.9(7) . . ?
C7 C8 C9 124.8(7) . . ?
N2 C8 C9 108.1(6) . . ?
O1 C9 N3 127.4(7) . . ?
O1 C9 C8 129.7(7) . . ?
N3 C9 C8 102.8(6) . . ?
N2 C10 N3 111.6(6) . . ?
N2 C10 S1 129.5(6) . . ?
N3 C10 S1 118.8(6) . . ?
C12 C11 C16 119.9(7) . . ?
C12 C11 N3 120.5(7) . . ?
C16 C11 N3 119.5(6) . . ?
C13 C12 C11 120.0(7) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 118.9(7) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 F1 117.9(9) . . ?
C15 C14 C13 122.5(8) . . ?
F1 C14 C13 119.6(7) . . ?
C14 C15 C16 118.8(8) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C11 120.0(7) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C6 N1 C2 C3 1.3(11) . . . . ?
Cu1 N1 C2 C3 -170.3(6) . . . . ?
N1 C2 C3 C4 1.2(12) . . . . ?
C2 C3 C4 C5 -1.4(12) . . . . ?
C3 C4 C5 C6 -0.8(12) . . . . ?
C2 N1 C6 C5 -3.5(10) . . . . ?
Cu1 N1 C6 C5 168.1(5) . . . . ?
C2 N1 C6 C7 170.6(7) . . . . ?
Cu1 N1 C6 C7 -17.9(9) . . . . ?
C4 C5 C6 N1 3.3(11) . . . . ?
C4 C5 C6 C7 -170.8(7) . . . . ?
N1 C6 C7 C8 -16.2(11) . . . . ?
C5 C6 C7 C8 157.9(8) . . . . ?
C6 C7 C8 N2 7.9(12) . . . . ?
C6 C7 C8 C9 -167.5(7) . . . . ?
C10 N2 C8 C7 -174.7(7) . . . . ?
Cu1 N2 C8 C7 32.3(9) . . . . ?
C10 N2 C8 C9 1.4(8) . . . . ?
Cu1 N2 C8 C9 -151.6(4) . . . . ?
C10 N3 C9 O1 177.9(7) . . . . ?
C11 N3 C9 O1 -1.9(12) . . . . ?
C10 N3 C9 C8 1.0(7) . . . . ?
C11 N3 C9 C8 -178.7(6) . . . . ?
C7 C8 C9 O1 -2.0(13) . . . . ?
N2 C8 C9 O1 -178.2(8) . . . . ?
C7 C8 C9 N3 174.7(7) . . . . ?
N2 C8 C9 N3 -1.5(7) . . . . ?
C8 N2 C10 N3 -0.8(8) . . . . ?
Cu1 N2 C10 N3 146.2(5) . . . . ?
C8 N2 C10 S1 175.4(6) . . . . ?
Cu1 N2 C10 S1 -37.6(10) . . . . ?
C9 N3 C10 N2 -0.2(8) . . . . ?
C11 N3 C10 N2 179.5(6) . . . . ?
C9 N3 C10 S1 -176.8(5) . . . . ?
C11 N3 C10 S1 2.9(9) . . . . ?
C17 S1 C10 N2 -6.2(8) . . . . ?
C17 S1 C10 N3 169.7(6) . . . . ?
C10 N3 C11 C12 -94.4(9) . . . . ?
C9 N3 C11 C12 85.3(9) . . . . ?
C10 N3 C11 C16 88.7(10) . . . . ?
C9 N3 C11 C16 -91.6(9) . . . . ?
C16 C11 C12 C13 0.4(12) . . . . ?
N3 C11 C12 C13 -176.5(8) . . . . ?
C11 C12 C13 C14 0.0(12) . . . . ?
C12 C13 C14 C15 -0.8(14) . . . . ?
C12 C13 C14 F1 179.1(8) . . . . ?
F1 C14 C15 C16 -178.8(9) . . . . ?
C13 C14 C15 C16 1.1(15) . . . . ?
C14 C15 C16 C11 -0.7(15) . . . . ?
C12 C11 C16 C15 -0.1(14) . . . . ?
N3 C11 C16 C15 176.9(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 Cl1 0.93 2.80 3.510(8) 134.4 1_556
C2 H2 Cl2 0.93 2.54 3.163(8) 124.2 .
C3 H3 O1 0.93 2.52 3.403(10) 158.1 16_546
C5 H5 Cl2 0.93 3.02 3.862(9) 151.4 12_554
C7 H7 Cl2 0.93 2.89 3.774(8) 158.9 12_554
C13 H13 Cl2 0.93 2.88 3.477(9) 123.0 5_554
C17 H17B Cl2 0.96 2.88 3.501(9) 123.7 6_654
C17 H17C Cl1 0.96 2.84 3.550(9) 131.8 .

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 2019537'
loop_
_audit_author_name
_audit_author_address
'Elena Beloglazkina'
;Moscow State University
Russia
;
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-09-24 downloaded from the CCDC.
;
_audit_creation_date             2020-07-24
_audit_creation_method           
;
Olex2 1.3-beta
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_chemical_formula_moiety         'C16 H12 Cl2 Cu F N3 O S'
_chemical_formula_sum            'C16 H12 Cl2 Cu F N3 O S'
_chemical_formula_weight         447.808
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu 0.34125 1.28947 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   7.287(2)
_cell_length_b                   22.731(7)
_cell_length_c                   11.092(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.638(6)
_cell_angle_gamma                90
_cell_volume                     1741.1(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2371
_cell_measurement_temperature    120
_cell_measurement_theta_max      24.73
_cell_measurement_theta_min      2.64
_exptl_absorpt_coefficient_mu    1.701
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0623 before and 0.0483 after correction.
The Ratio of minimum to maximum transmission is 0.7719.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_meas      .
_exptl_crystal_description       prism
_exptl_crystal_F_000             903.414
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.1025
_diffrn_reflns_av_unetI/netI     0.1126
_diffrn_reflns_Laue_measured_fraction_full 0.9883
_diffrn_reflns_Laue_measured_fraction_max 0.9891
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16266
_diffrn_reflns_point_group_measured_fraction_full 0.9883
_diffrn_reflns_point_group_measured_fraction_max 0.9891
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.13
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.9883
_diffrn_measured_fraction_theta_max 0.9891
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              28
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2701
_reflns_number_total             3373
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3-beta (Bourhis et al., 2015)'
_refine_diff_density_max         2.0323
_refine_diff_density_min         -1.2969
_refine_diff_density_rms         0.2636
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             9.5399
_refine_ls_goodness_of_fit_ref   1.0291
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0600
_refine_ls_restrained_S_all      1.0282
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²+14.7149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1443
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.808(2)
 0.192(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C15) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(F1A) = Uanis(F1)
4. Others
 Sof(F1)=Sof(H15)=1-FVAR(1)
 Sof(H11)=Sof(F1A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C11(H11), C4(H4), C3(H3), C1(H1), C6(H6), C13(H13), C12(H12),
 C14(H14), C15(H15)
5.b Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_group
Cu1 Cu 0.22105(13) 0.35687(4) 0.52611(8) 0.0170(2) Uani 1.000000 . . .
Cl1 Cl 0.5316(3) 0.38129(7) 0.61787(16) 0.0199(4) Uani 1.000000 . . .
Cl2 Cl 0.1175(3) 0.39740(8) 0.67546(16) 0.0232(4) Uani 1.000000 . . .
S1 S 0.3754(3) 0.46765(8) 0.31834(17) 0.0243(4) Uani 1.000000 . . .
O1 O 0.3918(8) 0.2688(2) 0.1351(5) 0.0262(12) Uani 1.000000 . . .
N1 N 0.0021(9) 0.2968(2) 0.4624(5) 0.0167(12) Uani 1.000000 . . .
N3 N 0.4202(9) 0.3647(3) 0.2157(5) 0.0213(13) Uani 1.000000 . . .
N2 N 0.2477(8) 0.3573(3) 0.3512(5) 0.0170(12) Uani 1.000000 . . .
C7 C 0.2478(11) 0.3014(3) 0.2970(6) 0.0194(16) Uani 1.000000 . . .
C10 C 0.5216(12) 0.3919(3) 0.1386(6) 0.0238(17) Uani 1.000000 . . .
C2 C -0.2894(11) 0.2545(3) 0.4813(7) 0.0221(16) Uani 1.000000 . . .
H2 H -0.3935(11) 0.2567(3) 0.5152(7) 0.0265(19) Uiso 1.000000 R . .
C11 C 0.4247(11) 0.4079(3) 0.0148(7) 0.0222(16) Uani 1.000000 . . .
H11 H 0.2887(11) 0.4020(3) -0.0189(7) 0.0267(19) Uiso 0.379(8) R . 1
C4 C -0.1243(12) 0.2067(3) 0.3544(7) 0.0229(16) Uani 1.000000 . . .
H4 H -0.1122(12) 0.1747(3) 0.3024(7) 0.0275(19) Uiso 1.000000 R . .
C8 C 0.3607(11) 0.3050(3) 0.2066(7) 0.0198(16) Uani 1.000000 . . .
C3 C -0.2767(12) 0.2090(3) 0.4031(7) 0.0245(17) Uani 1.000000 . . .
H3 H -0.3726(12) 0.1790(3) 0.3825(7) 0.029(2) Uiso 1.000000 R . .
C1 C -0.1467(11) 0.2974(3) 0.5096(7) 0.0214(16) Uani 1.000000 . . .
H1 H -0.1541(11) 0.3286(3) 0.5648(7) 0.0257(19) Uiso 1.000000 R . .
F1 F 0.2332(11) 0.4046(4) -0.0133(7) 0.0389(18) Uani 0.621(8) . . 2
C5 C 0.0111(11) 0.2520(3) 0.3826(6) 0.0171(15) Uani 1.000000 . . .
C16 C 0.2179(12) 0.4859(3) 0.4106(7) 0.0244(17) Uani 1.000000 . . .
H16a H 0.091(3) 0.4676(19) 0.372(3) 0.037(3) Uiso 1.000000 GR . .
H16b H 0.275(4) 0.471(2) 0.4977(15) 0.037(3) Uiso 1.000000 GR . .
H16c H 0.203(6) 0.5287(3) 0.412(4) 0.037(3) Uiso 1.000000 GR . .
C6 C 0.1523(10) 0.2537(3) 0.3138(6) 0.0179(15) Uani 1.000000 . . .
H6 H 0.1779(10) 0.2178(3) 0.2781(6) 0.0214(18) Uiso 1.000000 R . .
C9 C 0.3441(11) 0.3928(3) 0.3002(6) 0.0191(15) Uani 1.000000 . . .
C13 C 0.7169(14) 0.4410(4) -0.0123(8) 0.034(2) Uani 1.000000 . . .
H13 H 0.7842(14) 0.4583(4) -0.0638(8) 0.040(2) Uiso 1.000000 R . .
C12 C 0.5228(13) 0.4323(3) -0.0608(7) 0.0274(18) Uani 1.000000 . . .
H12 H 0.4549(13) 0.4430(3) -0.1463(7) 0.033(2) Uiso 1.000000 R . .
C14 C 0.8169(14) 0.4249(6) 0.1102(9) 0.058(3) Uani 1.000000 . . .
H14 H 0.9526(14) 0.4312(6) 0.1438(9) 0.070(4) Uiso 1.000000 R . .
C15 C 0.7174(15) 0.3992(5) 0.1849(8) 0.050(3) Uani 1.000000 . U .
H15 H 0.7865(15) 0.3866(5) 0.2688(8) 0.060(3) Uiso 0.621(8) R . 2
F1A F 0.7821(18) 0.4037(7) 0.3159(11) 0.0389(18) Uani 0.379(8) . . 1


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
Cu1 Cl1 2.235(2) . ?
Cu1 Cl2 2.228(2) . ?
Cu1 N1 2.047(6) . ?
Cu1 N2 2.010(5) . ?
S1 C16 1.813(8) . ?
S1 C9 1.720(7) . ?
O1 C8 1.214(9) . ?
N1 C1 1.346(10) . ?
N1 C5 1.364(9) . ?
N3 C10 1.438(9) . ?
N3 C8 1.417(9) . ?
N3 C9 1.388(9) . ?
N2 C7 1.405(9) . ?
N2 C9 1.312(9) . ?
C7 C8 1.489(10) . ?
C7 C6 1.333(10) . ?
C10 C11 1.377(10) . ?
C10 C15 1.364(12) . ?
C2 H2 0.9500 . ?
C2 C3 1.373(11) . ?
C2 C1 1.386(10) . ?
C11 H11 0.9500 . ?
C11 F1 1.331(11) . ?
C11 C12 1.381(11) . ?
C4 H4 0.9500 . ?
C4 C3 1.383(11) . ?
C4 C5 1.390(10) . ?
C3 H3 0.9500 . ?
C1 H1 0.9500 . ?
C5 C6 1.464(10) . ?
C16 H16a 0.9800 . ?
C16 H16b 0.9800 . ?
C16 H16c 0.9800 . ?
C6 H6 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.358(12) . ?
C13 C14 1.370(12) . ?
C12 H12 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.392(12) . ?
C15 H15 0.9500 . ?
C15 F1A 1.381(15) . ?

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
Cl2 Cu1 Cl1 95.34(7) . . ?
N1 Cu1 Cl1 152.52(18) . . ?
N1 Cu1 Cl2 96.93(17) . . ?
N2 Cu1 Cl1 92.42(17) . . ?
N2 Cu1 Cl2 151.16(19) . . ?
N2 Cu1 N1 88.6(2) . . ?
C9 S1 C16 102.0(3) . . ?
C1 N1 Cu1 119.6(5) . . ?
C5 N1 Cu1 121.9(5) . . ?
C5 N1 C1 118.2(6) . . ?
C8 N3 C10 125.0(6) . . ?
C9 N3 C10 126.5(6) . . ?
C9 N3 C8 108.1(6) . . ?
C7 N2 Cu1 115.0(4) . . ?
C9 N2 Cu1 130.5(5) . . ?
C9 N2 C7 107.4(6) . . ?
C8 C7 N2 108.3(6) . . ?
C6 C7 N2 127.1(7) . . ?
C6 C7 C8 124.3(6) . . ?
C11 C10 N3 120.6(7) . . ?
C15 C10 N3 120.2(7) . . ?
C15 C10 C11 119.0(7) . . ?
C3 C2 H2 120.8(5) . . ?
C1 C2 H2 120.8(4) . . ?
C1 C2 C3 118.5(7) . . ?
H11 C11 C10 119.6(5) . . ?
F1 C11 C10 112.6(7) . . ?
F1 C11 H11 10.4(5) . . ?
C12 C11 C10 120.8(7) . . ?
C12 C11 H11 119.6(5) . . ?
C12 C11 F1 126.0(7) . . ?
C3 C4 H4 120.5(4) . . ?
C5 C4 H4 120.5(4) . . ?
C5 C4 C3 119.1(7) . . ?
N3 C8 O1 125.3(6) . . ?
C7 C8 O1 131.5(7) . . ?
C7 C8 N3 103.1(6) . . ?
C4 C3 C2 119.9(7) . . ?
H3 C3 C2 120.0(5) . . ?
H3 C3 C4 120.0(4) . . ?
C2 C1 N1 122.9(7) . . ?
H1 C1 N1 118.5(4) . . ?
H1 C1 C2 118.5(4) . . ?
C4 C5 N1 121.3(7) . . ?
C6 C5 N1 120.4(6) . . ?
C6 C5 C4 118.0(6) . . ?
H16a C16 S1 109.5 . . ?
H16b C16 S1 109.5 . . ?
H16b C16 H16a 109.5 . . ?
H16c C16 S1 109.5 . . ?
H16c C16 H16a 109.5 . . ?
H16c C16 H16b 109.5 . . ?
C5 C6 C7 125.4(7) . . ?
H6 C6 C7 117.3(4) . . ?
H6 C6 C5 117.3(4) . . ?
N3 C9 S1 117.9(5) . . ?
N2 C9 S1 128.9(6) . . ?
N2 C9 N3 113.1(6) . . ?
C12 C13 H13 119.6(5) . . ?
C14 C13 H13 119.6(5) . . ?
C14 C13 C12 120.7(8) . . ?
C13 C12 C11 119.6(7) . . ?
H12 C12 C11 120.2(5) . . ?
H12 C12 C13 120.2(5) . . ?
H14 C14 C13 120.4(5) . . ?
C15 C14 C13 119.3(9) . . ?
C15 C14 H14 120.4(6) . . ?
C14 C15 C10 120.5(8) . . ?
H15 C15 C10 119.7(5) . . ?
H15 C15 C14 119.7(6) . . ?
F1A C15 C10 111.7(9) . . ?
F1A C15 C14 121.8(10) . . ?
F1A C15 H15 25.2(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
Cu1 N1 C1 C2 -173.1(5) . . . . ?
Cu1 N1 C5 C4 170.7(5) . . . . ?
Cu1 N1 C5 C6 -15.8(6) . . . . ?
Cu1 N2 C7 C8 -152.3(5) . . . . ?
Cu1 N2 C7 C6 32.6(6) . . . . ?
Cu1 N2 C9 S1 -38.0(7) . . . . ?
Cu1 N2 C9 N3 145.6(6) . . . . ?
S1 C9 N3 C10 -1.1(8) . . . . ?
S1 C9 N3 C8 -174.2(6) . . . . ?
S1 C9 N2 C7 173.9(7) . . . . ?
O1 C8 N3 C10 2.0(10) . . . . ?
O1 C8 N3 C9 175.2(8) . . . . ?
O1 C8 C7 N2 -176.3(9) . . . . ?
O1 C8 C7 C6 -1.1(10) . . . . ?
N1 C1 C2 C3 1.0(8) . . . . ?
N1 C5 C4 C3 3.5(8) . . . . ?
N1 C5 C6 C7 -16.6(8) . . . . ?
N3 C10 C11 F1 10.7(9) . . . . ?
N3 C10 C11 C12 -177.9(7) . . . . ?
N3 C10 C15 C14 179.2(10) . . . . ?
N3 C10 C15 F1A -27.4(10) . . . . ?
N3 C8 C7 N2 0.2(6) . . . . ?
N3 C8 C7 C6 175.4(6) . . . . ?
N3 C9 N2 C7 -2.4(7) . . . . ?
N2 C7 C6 C5 6.7(9) . . . . ?
C7 C6 C5 C4 157.2(8) . . . . ?
C10 C11 C12 C13 -0.4(9) . . . . ?
C10 C15 C14 C13 -2.3(13) . . . . ?
C2 C3 C4 C5 -2.0(9) . . . . ?
C11 C12 C13 C14 1.0(11) . . . . ?
C13 C14 C15 F1A -153.0(12) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
C15 0.0200

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.808(2)
2 0.192(2)
