# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_a21072701a0805
_database_code_depnum_ccdc_archive 'CCDC 2130391'
loop_
_audit_author_name
_audit_author_address
'Yaping Gong'
;Sun YatSen University
China
;
_audit_update_record             
;
2021-12-22 deposited with the CCDC.	2022-03-01 downloaded from the CCDC.
;
_audit_creation_date             2021-12-20
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Cu, 2(C8 H11 F N)'
_chemical_formula_sum            'C16 H22 Cl4 Cu F2 N2'
_chemical_formula_weight         485.69
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONFClCu
_chemical_oxdiff_usercomment     GYP-7
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'

_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.
;
_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_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                   20.0414(5)
_cell_length_b                   7.3061(2)
_cell_length_c                   7.3103(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.732(2)
_cell_angle_gamma                90
_cell_volume                     1063.03(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2591
_cell_measurement_temperature    297.98(10)
_cell_measurement_theta_max      73.8600
_cell_measurement_theta_min      4.4250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.40t (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             494
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3816
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.991
_diffrn_reflns_theta_min         4.443
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -48.00   1.00    1.00    --  -41.14 -38.00 150.00   66
  2  ω     25.00 115.00   1.00    1.00    --   41.14  38.00  30.00   90
  3  ω     15.00  81.00   1.00    1.00    --   41.14 -99.00 150.00   66
  4  ω     16.00  41.00   1.00    1.00    --   41.14 -99.00-150.00   25
  5  ω     87.00 156.00   1.00    2.00    --  107.79  30.00  90.00   69
  6  ω    121.00 177.00   1.00    2.00    --  107.79 125.00 150.00   56
  7  ω    145.00 172.00   1.00    2.00    --  107.79  45.00 -90.00   27
  8  ω     86.00 115.00   1.00    2.00    --  107.79  45.00 -90.00   29
  9  ω     95.00 164.00   1.00    2.00    --  107.79 125.00  90.00   69
 10  ω     51.00 112.00   1.00    2.00    --  107.79-125.00-180.00   61
 11  ω     63.00 141.00   1.00    2.00    --  107.79  15.00  60.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0575968000
_diffrn_orient_matrix_UB_12      -0.1403212000
_diffrn_orient_matrix_UB_13      -0.0065617000
_diffrn_orient_matrix_UB_21      0.0489163000
_diffrn_orient_matrix_UB_22      -0.1420781000
_diffrn_orient_matrix_UB_23      0.0964851000
_diffrn_orient_matrix_UB_31      -0.0167649000
_diffrn_orient_matrix_UB_32      0.0676194000
_diffrn_orient_matrix_UB_33      0.1889232000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1896
_reflns_number_total             2077
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.0075(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         2077
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0810P)²+0.5580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1285
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C7(H7a,H7b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C2(H2), C6(H6)
2.c Idealised Me refined as rotating group:
 N1(H1a,H1b,H1c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.5000 0.5000 0.0000 0.0311(2) Uani 1 2 d S T P . .
Cl1 Cl 0.49032(4) 0.71639(8) 0.22132(8) 0.0394(2) Uani 1 1 d . . . . .
Cl2 Cl 0.61494(3) 0.52736(11) 0.04810(11) 0.0460(2) Uani 1 1 d . . . . .
N1 N 0.39314(13) 0.4879(4) 0.4698(4) 0.0458(6) Uani 1 1 d . . . . .
H1A H 0.4199 0.5374 0.3944 0.055 Uiso 1 1 calc GR . . . .
H1B H 0.3989 0.3671 0.4729 0.055 Uiso 1 1 calc GR . . . .
H1C H 0.4032 0.5335 0.5826 0.055 Uiso 1 1 calc GR . . . .
F1 F 0.00461(16) 0.5394(7) 0.2192(7) 0.1493(19) Uani 1 1 d . . . . .
C8 C 0.32202(19) 0.5307(6) 0.4022(6) 0.0605(9) Uani 1 1 d . . . . .
H8A H 0.3164 0.6626 0.3993 0.073 Uiso 1 1 calc R . . . .
H8B H 0.3123 0.4861 0.2770 0.073 Uiso 1 1 calc R . . . .
C4 C 0.2016(2) 0.4824(7) 0.4307(7) 0.0720(12) Uani 1 1 d . . . . .
C7 C 0.2738(2) 0.4526(9) 0.5125(7) 0.0851(15) Uani 1 1 d . . . . .
H7A H 0.2803 0.5065 0.6345 0.102 Uiso 1 1 calc R . . . .
H7B H 0.2820 0.3221 0.5256 0.102 Uiso 1 1 calc R . . . .
C1 C 0.0697(2) 0.5218(8) 0.2880(9) 0.0880(16) Uani 1 1 d . . . . .
C3 C 0.1629(2) 0.6186(10) 0.4878(8) 0.1006(19) Uani 1 1 d . . . . .
H3 H 0.1819 0.7040 0.5728 0.121 Uiso 1 1 calc R . . . .
C5 C 0.1721(2) 0.3751(10) 0.2897(9) 0.112(2) Uani 1 1 d . . . . .
H5 H 0.1976 0.2854 0.2404 0.134 Uiso 1 1 calc R . . . .
C2 C 0.0960(3) 0.6323(10) 0.4218(9) 0.111(2) Uani 1 1 d . . . . .
H2 H 0.0691 0.7189 0.4708 0.133 Uiso 1 1 calc R . . . .
C6 C 0.1057(3) 0.3967(11) 0.2189(9) 0.108(2) Uani 1 1 d . . . . .
H6 H 0.0868 0.3227 0.1230 0.130 Uiso 1 1 calc R . . . .


_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 2.2866(6) . ?
Cu1 Cl1 2.2866(6) 3_665 ?
Cu1 Cl2 2.2977(7) 3_665 ?
Cu1 Cl2 2.2978(7) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C8 1.486(5) . ?
F1 C1 1.349(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.447(6) . ?
C4 C7 1.514(6) . ?
C4 C3 1.358(7) . ?
C4 C5 1.373(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C1 C2 1.328(8) . ?
C1 C6 1.302(8) . ?
C3 H3 0.9300 . ?
C3 C2 1.374(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(7) . ?
C2 H2 0.9300 . ?
C6 H6 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 Cl1 180.0 . 3_665 ?
Cl1 Cu1 Cl2 89.90(3) . . ?
Cl1 Cu1 Cl2 90.10(3) . 3_665 ?
Cl1 Cu1 Cl2 90.10(3) 3_665 . ?
Cl1 Cu1 Cl2 89.90(3) 3_665 3_665 ?
Cl2 Cu1 Cl2 180.0 3_665 . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C8 N1 H1A 109.5 . . ?
C8 N1 H1B 109.5 . . ?
C8 N1 H1C 109.5 . . ?
N1 C8 H8A 108.7 . . ?
N1 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C7 C8 N1 114.2(4) . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C3 C4 C7 122.6(5) . . ?
C3 C4 C5 116.0(5) . . ?
C5 C4 C7 121.5(5) . . ?
C8 C7 C4 113.1(4) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C4 C7 H7A 109.0 . . ?
C4 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C2 C1 F1 120.0(5) . . ?
C6 C1 F1 118.5(5) . . ?
C6 C1 C2 121.5(5) . . ?
C4 C3 H3 119.5 . . ?
C4 C3 C2 121.0(5) . . ?
C2 C3 H3 119.5 . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 121.9(5) . . ?
C6 C5 H5 119.0 . . ?
C1 C2 C3 120.1(5) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C6 C5 119.2(5) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?

_olex2_date_sample_data_collection 2021-07-27
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.811
_oxdiff_exptl_absorpt_empirical_full_min 0.583
####################################################################### 
# 
# 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_a21072703a0805
_database_code_depnum_ccdc_archive 'CCDC 2130395'
loop_
_audit_author_name
_audit_author_address
'Yaping Gong'
;Sun YatSen University
China
;
_audit_update_record             
;
2021-12-22 deposited with the CCDC.	2022-03-01 downloaded from the CCDC.
;
_audit_creation_date             2021-08-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Cu, 2(C8 H11 F N)'
_chemical_formula_sum            'C16 H22 Cl4 Cu F2 N2'
_chemical_formula_weight         485.69
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNFClCu
_chemical_oxdiff_usercomment     'GYP-7 415K'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c e'
_space_group_name_Hall           '-C 2bc 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   40.211(5)
_cell_length_b                   7.3967(3)
_cell_length_c                   7.3999(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2201.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2296
_cell_measurement_temperature    415.00(10)
_cell_measurement_theta_max      72.3660
_cell_measurement_theta_min      4.3760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.038
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.40t (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5878
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.895
_diffrn_reflns_theta_min         4.398
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      415.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -109.00 -22.00   1.00    1.61    --  -41.14 -38.00 -60.00   87
  2  ω    -74.00  35.00   1.00    1.61    --  -41.14  77.00  90.00  109
  3  ω     17.00 113.00   1.00    1.61    --   41.14  57.00-150.00   96
  4  ω     29.00  82.00   1.00    1.61    --   41.14-125.00 -30.00   53
  5  ω    100.00 126.00   1.00    6.45    --  107.79 -61.00 -60.00   26
  6  ω     86.00 171.00   1.00    6.45    --  107.79  45.00 -90.00   85
  7  ω     69.00  96.00   1.00    6.45    --  107.79 -77.00  90.00   27
  8  ω     36.00 116.00   1.00    6.45    --  107.79-125.00 120.00   80
  9  ω     36.00 137.00   1.00    6.45    --  107.79 -61.00-180.00  101
 10  ω     55.00 107.00   1.00    6.45    --  107.79 -94.00-180.00   52
 11  ω     72.00 117.00   1.00    6.45    --  107.79-125.00  60.00   45
 12  ω     64.00 109.00   1.00    6.45    --  107.79 -94.00 -60.00   45
 13  ω     37.00 131.00   1.00    6.45    --  107.79 -45.00  60.00   94
 14  ω     38.00 125.00   1.00    6.45    --  107.79 -45.00 -90.00   87
 15  ω     46.00 174.00   1.00    6.45    --  107.79   0.00  60.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0301130000
_diffrn_orient_matrix_UB_12      0.0114157000
_diffrn_orient_matrix_UB_13      -0.1278652000
_diffrn_orient_matrix_UB_21      -0.0220747000
_diffrn_orient_matrix_UB_22      0.0881119000
_diffrn_orient_matrix_UB_23      -0.1458320000
_diffrn_orient_matrix_UB_31      0.0085120000
_diffrn_orient_matrix_UB_32      0.1883121000
_diffrn_orient_matrix_UB_33      0.0760044000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                703
_reflns_number_total             1045
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.922
_refine_diff_density_min         -1.339
_refine_diff_density_rms         0.150
_refine_ls_extinction_coef       0.0037(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         1045
_refine_ls_number_restraints     161
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.0978
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²+8.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2765
_refine_ls_wR_factor_ref         0.3325
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.716(18)
 0.284(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
3. Restrained distances
 N1-C8
 1.5 with sigma of 0.02
 C7-N1
 2.5 with sigma of 0.02
 C7-C4 = C8-C7
 1.52 with sigma of 0.02
 F1-C1
 1.43 with sigma of 0.02
 C1-C2 \\sim C2-C3 \\sim C3-C4 \\sim C4-C5 \\sim C5-C6 \\sim C6-C1
 with sigma of 0.04
 C1-C5 \\sim C1-C3 \\sim C6-C4 \\sim C2-C6 \\sim C3-C5 \\sim C2-C4
 with sigma of 0.04
 F1-C6 \\sim F1-C2
 with sigma of 0.04
4. Restrained planarity
 F1, C1, C2, C3, C4, C5, C6, C7
 with sigma of 0.05
5. Uiso/Uaniso restraints and constraints
F1 \\sim N1 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7
\\sim C8: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C6) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C7) \\sim
Ueq, Uanis(C4) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C2)
\\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(F1) \\sim Ueq: with sigma of 0.04 and
sigma for terminal atoms of 0.08
6. Others
 Fixed Sof: F1(0.5) N1(0.5) H1A(0.5) H1B(0.5) H1C(0.5) C1(0.5) C2(0.5) H2(0.5)
 C3(0.5) H3(0.5) C4(0.5) C5(0.5) H5(0.5) C6(0.5) H6(0.5) C7(0.5) H7A(0.5)
 H7B(0.5) C8(0.5) H8A(0.5) H8B(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
7.c Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,C6)
7.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.5000 0.5000 0.5000 0.0723(11) Uani 1 4 d S T P . .
Cl2 Cl 0.55678(11) 0.5000 0.5000 0.1043(14) Uani 1 2 d S T P . .
Cl1 Cl 0.5000 0.7180(4) 0.2826(4) 0.0878(13) Uani 1 2 d S T P . .
F1 F 0.2543(5) 0.998(6) 0.589(5) 0.261(16) Uani 0.5 1 d D U . A -1
N1 N 0.4482(4) 0.994(10) 0.506(9) 0.115(7) Uani 0.5 1 d D U . A -1
H1A H 0.4513 0.9861 0.3876 0.138 Uiso 0.5 1 calc GR . . A -1
H1B H 0.4572 0.8987 0.5604 0.138 Uiso 0.5 1 calc GR . . A -1
H1C H 0.4577 1.0948 0.5474 0.138 Uiso 0.5 1 calc GR . . A -1
C1 C 0.2878(4) 0.998(6) 0.537(3) 0.225(11) Uani 0.5 1 d D U . A -1
C2 C 0.3046(8) 0.835(6) 0.511(4) 0.227(12) Uani 0.5 1 d DG U . A -1
H2 H 0.2936 0.7262 0.5280 0.272 Uiso 0.5 1 calc R . . A -1
C3 C 0.3378(8) 0.836(8) 0.458(4) 0.222(12) Uani 0.5 1 d DG U . A -1
H3 H 0.3489 0.7278 0.4404 0.267 Uiso 0.5 1 calc R . . A -1
C4 C 0.3542(5) 1.000(9) 0.432(4) 0.201(11) Uani 0.5 1 d DG U . A -1
C5 C 0.3375(8) 1.162(8) 0.459(4) 0.221(12) Uani 0.5 1 d DG U . A -1
H5 H 0.3485 1.2711 0.4412 0.265 Uiso 0.5 1 calc R . . A -1
C6 C 0.3043(8) 1.161(6) 0.511(4) 0.225(12) Uani 0.5 1 d DG U . A -1
H6 H 0.2931 1.2695 0.5288 0.270 Uiso 0.5 1 calc R . . A -1
C7 C 0.3905(6) 0.999(6) 0.380(4) 0.175(10) Uani 0.5 1 d D U . A -1
H7A H 0.3953 0.8926 0.3083 0.210 Uiso 0.5 1 calc R . . A -1
H7B H 0.3954 1.1050 0.3077 0.210 Uiso 0.5 1 calc R . . A -1
C8 C 0.4117(5) 0.999(8) 0.546(5) 0.139(10) Uani 0.5 1 d D U . A -1
H8A H 0.4069 1.1071 0.6160 0.167 Uiso 0.5 1 calc R . . A -1
H8B H 0.4060 0.8954 0.6196 0.167 Uiso 0.5 1 calc R . . A -1


_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 Cl2 2.283(4) 9_666 ?
Cu1 Cl2 2.283(4) . ?
Cu1 Cl1 2.278(2) . ?
Cu1 Cl1 2.278(2) 9_666 ?
F1 C1 1.404(18) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C8 1.495(18) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 H2 0.9300 . ?
C2 C3 1.3900 . ?
C3 H3 0.9300 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C4 C7 1.508(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.3900 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.496(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

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 Cl2 180.0 9_666 . ?
Cl1 Cu1 Cl2 90.0 . 9_666 ?
Cl1 Cu1 Cl2 90.0 . . ?
Cl1 Cu1 Cl2 90.0 9_666 9_666 ?
Cl1 Cu1 Cl2 90.0 9_666 . ?
Cl1 Cu1 Cl1 180.00(9) . 9_666 ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C8 N1 H1A 109.5 . . ?
C8 N1 H1B 109.5 . . ?
C8 N1 H1C 109.5 . . ?
C2 C1 F1 120.4(17) . . ?
C2 C1 C6 120.0 . . ?
C6 C1 F1 119.6(17) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 C7 120(4) . . ?
C5 C4 C7 120(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C4 C7 H7A 109.6 . . ?
C4 C7 H7B 109.6 . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 C4 110.1(18) . . ?
C8 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
N1 C8 C7 114(2) . . ?
N1 C8 H8A 108.9 . . ?
N1 C8 H8B 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?

_olex2_date_sample_data_collection 2021-07-27
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.093
_oxdiff_exptl_absorpt_empirical_full_min 0.506
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.716(18)
2 0.284(18)

####################################################################### 
# 
# 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_new
_database_code_depnum_ccdc_archive 'CCDC 2130394'
loop_
_audit_author_name
_audit_author_address
'Yaping Gong'
;Sun YatSen University
China
;
_audit_update_record             
;
2022-02-12 deposited with the CCDC.	2022-03-01 downloaded from the CCDC.
;
_audit_creation_date             2022-02-11
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Cu, 2(C8 H11 F N)'
_chemical_formula_sum            'C16 H22 Cl4 Cu F2 N2'
_chemical_formula_weight         485.69
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'A 1 2/m 1'
_space_group_name_Hall           '-A 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x, y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z'
'-x, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   20.4140(9)
_cell_length_b                   7.3636(3)
_cell_length_c                   7.3256(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.344(3)
_cell_angle_gamma                90
_cell_volume                     1083.29(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2112
_cell_measurement_temperature    364.99(10)
_cell_measurement_theta_max      74.0230
_cell_measurement_theta_min      4.3820
_shelx_estimated_absorpt_T_max   0.887
_shelx_estimated_absorpt_T_min   0.309
_exptl_absorpt_coefficient_mu    6.134
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.40t (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             494
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3423
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.218
_diffrn_reflns_theta_min         4.403
_diffrn_ambient_temperature      364.99(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1124
_reflns_number_total             1183
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-beta (Bourhis et al., 2015)'
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0082(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1183
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.367
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0758P)²+0.3124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1138
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.498(7)
 0.502(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
3. Restrained distances
 N1-C8
 1.47 with sigma of 0.02
 C7-C8 = C4-C7
 1.5 with sigma of 0.01
 C7-C3 \\sim C7-C5
 with sigma of 0.02
 F1-C2 \\sim F1-C6
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(Cu1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Others
 Fixed Sof: Cl1(0.5) F1(0.5) N1(0.5) H1A(0.5) H1B(0.5) H1C(0.5) C8(0.5)
 H8A(0.5) H8B(0.5) C7(0.5) H7A(0.5) H7B(0.5) C4(0.5) C3(0.5) H3(0.5) C2(0.5)
 H2(0.5) C1(0.5) C6(0.5) H6(0.5) C5(0.5) H5(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C6(H6), C5(H5)
6.c Fitted hexagon refined as free rotating group:
 C4(C3,C2,C1,C6,C5)
6.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.5000 0.5000 0.5000 0.0440(3) Uani 1 4 d S TU P . .
Cl2 Cl 0.61388(4) 0.5000 0.5548(6) 0.0715(3) Uani 1 2 d S T P . .
Cl1 Cl 0.4997(3) 0.28095(13) 0.7206(2) 0.0608(4) Uani 0.5 1 d . . P . .
F1 F 0.9929(3) 0.556(3) 0.233(3) 0.260(10) Uani 0.5 1 d D . P A -1
N1 N 0.60531(18) 0.501(3) 0.0428(17) 0.0675(14) Uani 0.5 1 d D . P A -1
H1A H 0.5957 0.5292 -0.0771 0.081 Uiso 0.5 1 calc R U P A -1
H1B H 0.5803 0.5671 0.1052 0.081 Uiso 0.5 1 calc R U P A -1
H1C H 0.5971 0.3834 0.0573 0.081 Uiso 0.5 1 calc R U P A -1
C8 C 0.6763(3) 0.5380(7) 0.114(2) 0.077(3) Uani 0.5 1 d D . P A -1
H8A H 0.6856 0.6624 0.0836 0.093 Uiso 0.5 1 calc R U P A -1
H8B H 0.6840 0.5285 0.2484 0.093 Uiso 0.5 1 calc R U P A -1
C7 C 0.7224(4) 0.4216(14) 0.0455(15) 0.104(3) Uani 0.5 1 d D . P A -1
H7A H 0.7198 0.4432 -0.0862 0.125 Uiso 0.5 1 calc R U P A -1
H7B H 0.7102 0.2960 0.0616 0.125 Uiso 0.5 1 calc R U P A -1
C4 C 0.7927(2) 0.4532(9) 0.1448(18) 0.137(5) Uani 0.5 1 d DG . P A -1
C3 C 0.8183(3) 0.5849(15) 0.2741(19) 0.197(12) Uani 0.5 1 d DG . P A -1
H3 H 0.7900 0.6470 0.3388 0.236 Uiso 0.5 1 calc R U P A -1
C2 C 0.8860(4) 0.6237(19) 0.307(2) 0.208(12) Uani 0.5 1 d DG . P A -1
H2 H 0.9031 0.7118 0.3931 0.250 Uiso 0.5 1 calc R U P A -1
C1 C 0.9282(3) 0.531(2) 0.210(2) 0.140(7) Uani 0.5 1 d G . P A -1
C6 C 0.9027(3) 0.3990(18) 0.0806(19) 0.138(6) Uani 0.5 1 d DG . P A -1
H6 H 0.9309 0.3369 0.0159 0.166 Uiso 0.5 1 calc R U P A -1
C5 C 0.8349(3) 0.3603(13) 0.0480(17) 0.198(11) Uani 0.5 1 d DG . P A -1
H5 H 0.8179 0.2721 -0.0385 0.237 Uiso 0.5 1 calc R U P A -1


_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 Cl2 2.2870(9) 5_666 ?
Cu1 Cl2 2.2870(8) . ?
Cu1 Cl1 2.2839(7) 2_656 ?
Cu1 Cl1 2.2839(7) 6_565 ?
Cu1 Cl1 2.2840(7) 5_666 ?
Cu1 Cl1 2.2840(7) . ?
Cl1 Cl1 0.6259(15) 7_656 ?
F1 C1 1.314(9) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C8 1.475(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.430(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C4 1.507(8) . ?
C4 C3 1.3900 . ?
C4 C5 1.3900 . ?
C3 H3 0.9300 . ?
C3 C2 1.3900 . ?
C2 H2 0.9300 . ?
C2 C1 1.3900 . ?
C1 C6 1.3900 . ?
C6 H6 0.9300 . ?
C6 C5 1.3900 . ?
C5 H5 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
Cl2 Cu1 Cl2 180.0 5_666 . ?
Cl1 Cu1 Cl2 89.57(17) 2_656 . ?
Cl1 Cu1 Cl2 90.43(17) 5_666 5_666 ?
Cl1 Cu1 Cl2 90.43(17) 6_565 . ?
Cl1 Cu1 Cl2 90.43(17) . . ?
Cl1 Cu1 Cl2 89.57(17) 6_565 5_666 ?
Cl1 Cu1 Cl2 89.57(17) 5_666 . ?
Cl1 Cu1 Cl2 90.43(17) 2_656 5_666 ?
Cl1 Cu1 Cl2 89.57(17) . 5_666 ?
Cl1 Cu1 Cl1 90.14(6) 6_565 5_666 ?
Cl1 Cu1 Cl1 180.0 . 5_666 ?
Cl1 Cu1 Cl1 90.14(6) 2_656 . ?
Cl1 Cu1 Cl1 89.86(6) 6_565 . ?
Cl1 Cu1 Cl1 180.0 6_565 2_656 ?
Cl1 Cu1 Cl1 89.86(6) 2_656 5_666 ?
Cl1 Cl1 Cu1 177.8(8) 7_656 . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C8 N1 H1A 109.5 . . ?
C8 N1 H1B 109.5 . . ?
C8 N1 H1C 109.5 . . ?
N1 C8 H8A 108.4 . . ?
N1 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C7 C8 N1 115.5(10) . . ?
C7 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C8 C7 C4 111.6(7) . . ?
H7A C7 H7B 108.0 . . ?
C4 C7 H7A 109.3 . . ?
C4 C7 H7B 109.3 . . ?
C3 C4 C7 130.2(5) . . ?
C3 C4 C5 120.0 . . ?
C5 C4 C7 107.6(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C1 C2 H2 120.0 . . ?
F1 C1 C2 124.3(7) . . ?
F1 C1 C6 115.7(7) . . ?
C6 C1 C2 120.0 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?

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
N1 H1A Cl2 0.89 2.80 3.611(15) 152.9 1_554
N1 H1A Cl1 0.89 2.64 3.313(12) 133.5 6_564
N1 H1A Cl1 0.89 2.76 3.330(12) 123.3 4_655
N1 H1B Cl1 0.89 2.51 3.394(15) 172.7 5_666
N1 H1B Cl1 0.89 2.53 3.407(16) 168.7 3_554
N1 H1C Cl2 0.89 2.84 3.69(2) 159.5 3_544
N1 H1C Cl1 0.89 2.77 3.414(14) 129.8 8_554
C8 H8A Cl2 0.97 2.87 3.631(5) 135.6 3_554
C8 H8B Cl2 0.97 2.88 3.687(15) 141.5 .

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
F1 C1 C6 C5 179.1(17) . . . . ?
N1 C8 C7 C4 -172.3(10) . . . . ?
C8 C7 C4 C3 -6.8(17) . . . . ?
C8 C7 C4 C5 -169.3(9) . . . . ?
C7 C4 C3 C2 -160.7(13) . . . . ?
C7 C4 C5 C6 164.6(10) . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C3 C2 C1 F1 -179.1(19) . . . . ?
C3 C2 C1 C6 0.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C5 C4 C3 C2 0.0 . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.498(7)
2 0.502(7)

