# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_cubis_93K
_database_code_depnum_ccdc_archive 'CCDC 1884411'
_audit_update_record             
;
2019-01-14 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C27 H8 Cl7 Cu F12 N2 O4'
_chemical_formula_moiety         'C27 H8 Cl7 Cu F12 N2 O4'
_chemical_formula_weight         964.07
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_symmetry_equiv_pos_as_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                   15.3530(17)
_cell_length_b                   11.0280(10)
_cell_length_c                   20.812(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.899(6)
_cell_angle_gamma                90.0000
_cell_volume                     3434.8(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4663
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.864
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888.00
_exptl_absorpt_coefficient_mu    1.283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.671
_exptl_absorpt_correction_T_max  0.774

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            13470
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         3.001
_diffrn_reflns_theta_full        27.480
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3927
_reflns_number_gt                3269
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0959
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3927
_refine_ls_number_parameters     243
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0439P)²+13.4451P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.2500 0.2500 0.5000 0.01906(13) Uani 1 2 d S . .
Cl1 Cl 0.12879(5) 0.20040(7) 0.22693(4) 0.02585(18) Uani 1 1 d . . .
Cl2 Cl -0.02861(5) -0.07138(7) 0.38950(4) 0.02757(18) Uani 1 1 d . . .
Cl3 Cl 0.0000 -0.54426(10) 0.2500 0.0490(4) Uani 1 2 d S . .
Cl4 Cl 0.18145(5) -0.12741(7) 0.28137(4) 0.0332(2) Uani 1 1 d . . .
F1 F 0.48023(14) 0.0920(2) 0.39776(11) 0.0434(5) Uani 1 1 d . . .
F2 F 0.45918(19) -0.0914(2) 0.42311(14) 0.0633(8) Uani 1 1 d . . .
F3 F 0.36323(15) -0.0002(2) 0.34643(11) 0.0542(7) Uani 1 1 d . . .
F4 F 0.15915(15) -0.13850(18) 0.54025(11) 0.0447(5) Uani 1 1 d . . .
F5 F 0.24146(16) -0.07684(19) 0.63188(10) 0.0431(5) Uani 1 1 d . . .
F6 F 0.29262(15) -0.20843(18) 0.57279(11) 0.0435(5) Uani 1 1 d . . .
O1 O 0.35286(16) 0.17064(19) 0.45382(11) 0.0313(5) Uani 1 1 d . . .
O2 O 0.24356(15) 0.09751(18) 0.54643(10) 0.0242(5) Uani 1 1 d . . .
N1 N 0.15448(18) 0.1842(2) 0.41864(12) 0.0251(6) Uani 1 1 d . . .
C1 C 0.0000 -0.0004(3) 0.2500 0.0170(8) Uani 1 2 d S . .
C2 C 0.1607(2) 0.2149(3) 0.35761(15) 0.0232(6) Uani 1 1 d . . .
H2 H 0.2014 0.2769 0.3520 0.028 Uiso 1 1 calc R . .
C3 C 0.1097(2) 0.1590(2) 0.30258(14) 0.0202(6) Uani 1 1 d . . .
C4 C 0.04986(19) 0.0646(2) 0.30755(14) 0.0179(6) Uani 1 1 d . . .
C5 C 0.04444(19) 0.0367(2) 0.37257(15) 0.0196(6) Uani 1 1 d . . .
C6 C 0.0958(2) 0.0979(3) 0.42592(15) 0.0230(6) Uani 1 1 d . . .
H6 H 0.0893 0.0781 0.4690 0.028 Uiso 1 1 calc R . .
C7 C 0.0000 -0.3875(4) 0.2500 0.0303(10) Uani 1 2 d S . .
C8 C 0.0801(2) -0.3265(3) 0.26521(15) 0.0283(7) Uani 1 1 d . . .
H8 H 0.1349 -0.3697 0.2751 0.034 Uiso 1 1 calc R . .
C9 C 0.0794(2) -0.2009(3) 0.26586(15) 0.0216(6) Uani 1 1 d . . .
C10 C 0.0000 -0.1341(3) 0.2500 0.0180(8) Uani 1 2 d S . .
C11 C 0.4181(2) 0.0139(3) 0.40559(17) 0.0350(8) Uani 1 1 d . . .
C12 C 0.3642(2) 0.0596(3) 0.45448(15) 0.0263(7) Uani 1 1 d . . .
C13 C 0.3309(2) -0.0298(3) 0.49176(15) 0.0280(7) Uani 1 1 d . . .
H13 H 0.3473 -0.1121 0.4876 0.034 Uiso 1 1 calc R . .
C14 C 0.2757(2) -0.0026(3) 0.53371(14) 0.0245(6) Uani 1 1 d . . .
C15 C 0.2430(2) -0.1080(3) 0.57014(17) 0.0328(8) Uani 1 1 d . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O2 1.953(2) . ?
Cu1 O2 1.953(2) 7_556 ?
Cu1 N1 2.106(3) 7_556 ?
Cu1 N1 2.106(3) . ?
Cu1 O1 2.205(2) 7_556 ?
Cu1 O1 2.205(2) . ?
Cl1 C3 1.726(3) . ?
Cl2 C5 1.726(3) . ?
Cl3 C7 1.729(4) . ?
Cl4 C9 1.729(3) . ?
F1 C11 1.322(4) . ?
F2 C11 1.333(4) . ?
F3 C11 1.337(4) . ?
F4 C15 1.342(4) . ?
F5 C15 1.335(4) . ?
F6 C15 1.338(4) . ?
O1 C12 1.237(4) . ?
O2 C14 1.261(4) . ?
N1 C2 1.339(4) . ?
N1 C6 1.342(4) . ?
C1 C4 1.458(3) . ?
C1 C4 1.458(3) 2 ?
C1 C10 1.474(5) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.407(4) . ?
C4 C5 1.408(4) . ?
C5 C6 1.385(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.375(4) . ?
C7 C8 1.375(4) 2 ?
C8 C9 1.384(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.400(3) . ?
C10 C9 1.400(3) 2 ?
C11 C12 1.532(5) . ?
C12 C13 1.419(4) . ?
C13 C14 1.379(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.532(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 180.00(10) . 7_556 ?
O2 Cu1 N1 90.12(9) . 7_556 ?
O2 Cu1 N1 89.88(9) 7_556 7_556 ?
O2 Cu1 N1 89.88(9) . . ?
O2 Cu1 N1 90.12(9) 7_556 . ?
N1 Cu1 N1 180.0 7_556 . ?
O2 Cu1 O1 90.33(9) . 7_556 ?
O2 Cu1 O1 89.67(9) 7_556 7_556 ?
N1 Cu1 O1 87.18(9) 7_556 7_556 ?
N1 Cu1 O1 92.82(9) . 7_556 ?
O2 Cu1 O1 89.67(9) . . ?
O2 Cu1 O1 90.33(9) 7_556 . ?
N1 Cu1 O1 92.82(9) 7_556 . ?
N1 Cu1 O1 87.18(9) . . ?
O1 Cu1 O1 180.00(9) 7_556 . ?
C12 O1 Cu1 120.1(2) . . ?
C14 O2 Cu1 125.8(2) . . ?
C2 N1 C6 118.6(3) . . ?
C2 N1 Cu1 119.4(2) . . ?
C6 N1 Cu1 121.2(2) . . ?
C4 C1 C4 121.1(3) . 2 ?
C4 C1 C10 119.47(17) . . ?
C4 C1 C10 119.47(17) 2 . ?
N1 C2 C3 121.8(3) . . ?
N1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 Cl1 117.3(2) . . ?
C4 C3 Cl1 120.6(2) . . ?
C3 C4 C5 114.3(3) . . ?
C3 C4 C1 122.4(2) . . ?
C5 C4 C1 123.3(2) . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 Cl2 116.9(2) . . ?
C4 C5 Cl2 121.8(2) . . ?
N1 C6 C5 122.1(3) . . ?
N1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C8 C7 C8 121.4(4) . 2 ?
C8 C7 Cl3 119.3(2) . . ?
C8 C7 Cl3 119.3(2) 2 . ?
C7 C8 C9 118.9(3) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C8 C9 C10 122.1(3) . . ?
C8 C9 Cl4 117.6(2) . . ?
C10 C9 Cl4 120.1(2) . . ?
C9 C10 C9 116.4(4) 2 . ?
C9 C10 C1 121.79(18) 2 . ?
C9 C10 C1 121.79(18) . . ?
F1 C11 F2 106.9(3) . . ?
F1 C11 F3 106.6(3) . . ?
F2 C11 F3 108.2(3) . . ?
F1 C11 C12 112.3(3) . . ?
F2 C11 C12 113.4(3) . . ?
F3 C11 C12 109.1(3) . . ?
O1 C12 C13 128.8(3) . . ?
O1 C12 C11 114.4(3) . . ?
C13 C12 C11 116.7(3) . . ?
C14 C13 C12 122.8(3) . . ?
C14 C13 H13 118.6 . . ?
C12 C13 H13 118.6 . . ?
O2 C14 C13 130.4(3) . . ?
O2 C14 C15 112.0(3) . . ?
C13 C14 C15 117.6(3) . . ?
F5 C15 F6 107.8(3) . . ?
F5 C15 F4 106.8(3) . . ?
F6 C15 F4 106.9(3) . . ?
F5 C15 C14 111.0(3) . . ?
F6 C15 C14 113.7(3) . . ?
F4 C15 C14 110.3(3) . . ?

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
O2 Cu1 O1 C12 15.8(2) . . . . ?
O2 Cu1 O1 C12 -164.2(2) 7_556 . . . ?
N1 Cu1 O1 C12 105.9(2) 7_556 . . . ?
N1 Cu1 O1 C12 -74.1(2) . . . . ?
O1 Cu1 O1 C12 -98(55) 7_556 . . . ?
O2 Cu1 O2 C14 75(100) 7_556 . . . ?
N1 Cu1 O2 C14 -106.8(2) 7_556 . . . ?
N1 Cu1 O2 C14 73.2(2) . . . . ?
O1 Cu1 O2 C14 166.0(2) 7_556 . . . ?
O1 Cu1 O2 C14 -14.0(2) . . . . ?
O2 Cu1 N1 C2 -144.7(2) . . . . ?
O2 Cu1 N1 C2 35.3(2) 7_556 . . . ?
N1 Cu1 N1 C2 -10(100) 7_556 . . . ?
O1 Cu1 N1 C2 125.0(2) 7_556 . . . ?
O1 Cu1 N1 C2 -55.0(2) . . . . ?
O2 Cu1 N1 C6 25.1(2) . . . . ?
O2 Cu1 N1 C6 -154.9(2) 7_556 . . . ?
N1 Cu1 N1 C6 160(100) 7_556 . . . ?
O1 Cu1 N1 C6 -65.3(2) 7_556 . . . ?
O1 Cu1 N1 C6 114.7(2) . . . . ?
C6 N1 C2 C3 -1.1(5) . . . . ?
Cu1 N1 C2 C3 169.0(2) . . . . ?
N1 C2 C3 C4 -1.6(5) . . . . ?
N1 C2 C3 Cl1 -176.2(2) . . . . ?
C2 C3 C4 C5 2.5(4) . . . . ?
Cl1 C3 C4 C5 176.9(2) . . . . ?
C2 C3 C4 C1 -175.9(3) . . . . ?
Cl1 C3 C4 C1 -1.5(4) . . . . ?
C4 C1 C4 C3 -49.6(2) 2 . . . ?
C10 C1 C4 C3 130.4(2) . . . . ?
C4 C1 C4 C5 132.2(3) 2 . . . ?
C10 C1 C4 C5 -47.8(3) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C1 C4 C5 C6 177.4(3) . . . . ?
C3 C4 C5 Cl2 177.0(2) . . . . ?
C1 C4 C5 Cl2 -4.7(4) . . . . ?
C2 N1 C6 C5 2.6(5) . . . . ?
Cu1 N1 C6 C5 -167.2(2) . . . . ?
C4 C5 C6 N1 -1.6(5) . . . . ?
Cl2 C5 C6 N1 -179.6(2) . . . . ?
C8 C7 C8 C9 0.8(2) 2 . . . ?
Cl3 C7 C8 C9 -179.2(2) . . . . ?
C7 C8 C9 C10 -1.5(4) . . . . ?
C7 C8 C9 Cl4 -177.00(19) . . . . ?
C8 C9 C10 C9 0.8(2) . . . 2 ?
Cl4 C9 C10 C9 176.1(3) . . . 2 ?
C8 C9 C10 C1 -179.2(2) . . . . ?
Cl4 C9 C10 C1 -3.9(3) . . . . ?
C4 C1 C10 C9 128.79(19) . . . 2 ?
C4 C1 C10 C9 -51.21(19) 2 . . 2 ?
C4 C1 C10 C9 -51.21(19) . . . . ?
C4 C1 C10 C9 128.79(19) 2 . . . ?
Cu1 O1 C12 C13 -12.6(4) . . . . ?
Cu1 O1 C12 C11 164.1(2) . . . . ?
F1 C11 C12 O1 33.9(4) . . . . ?
F2 C11 C12 O1 155.2(3) . . . . ?
F3 C11 C12 O1 -84.1(4) . . . . ?
F1 C11 C12 C13 -148.9(3) . . . . ?
F2 C11 C12 C13 -27.6(4) . . . . ?
F3 C11 C12 C13 93.1(4) . . . . ?
O1 C12 C13 C14 1.9(5) . . . . ?
C11 C12 C13 C14 -174.8(3) . . . . ?
Cu1 O2 C14 C13 8.8(5) . . . . ?
Cu1 O2 C14 C15 -168.7(2) . . . . ?
C12 C13 C14 O2 1.6(5) . . . . ?
C12 C13 C14 C15 178.9(3) . . . . ?
O2 C14 C15 F5 -41.0(4) . . . . ?
C13 C14 C15 F5 141.2(3) . . . . ?
O2 C14 C15 F6 -162.8(3) . . . . ?
C13 C14 C15 F6 19.4(4) . . . . ?
O2 C14 C15 F4 77.2(3) . . . . ?
C13 C14 C15 F4 -100.6(3) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_cubis_110K
_database_code_depnum_ccdc_archive 'CCDC 1884445'
_audit_update_record             
;
2019-01-14 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C27 H8 Cl7 Cu F12 N2 O4'
_chemical_formula_moiety         'C27 H8 Cl7 Cu F12 N2 O4'
_chemical_formula_weight         964.07
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_symmetry_equiv_pos_as_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                   15.3431(18)
_cell_length_b                   11.0404(10)
_cell_length_c                   20.877(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.735(6)
_cell_angle_gamma                90.0000
_cell_volume                     3449.4(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4663
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    110
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.856
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888.00
_exptl_absorpt_coefficient_mu    1.278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_T_max  0.962

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      110
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            13585
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         3.235
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3957
_reflns_number_gt                3240
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.0967
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3957
_refine_ls_number_parameters     243
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0480P)²+8.7271P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.40
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.7500 0.2500 0.5000 0.02191(14) Uani 1 2 d S . .
Cl1 Cl 0.62883(5) 0.20047(7) 0.22725(4) 0.03077(19) Uani 1 1 d . . .
Cl2 Cl 0.47089(5) -0.07194(7) 0.38896(4) 0.03273(19) Uani 1 1 d . . .
Cl3 Cl 0.5000 -0.54357(10) 0.2500 0.0568(4) Uani 1 2 d S . .
Cl4 Cl 0.68137(5) -0.12734(7) 0.28183(5) 0.0385(2) Uani 1 1 d . . .
F1 F 0.97972(14) 0.0938(2) 0.39864(11) 0.0499(6) Uani 1 1 d . . .
F2 F 0.9583(2) -0.0895(2) 0.42253(14) 0.0745(8) Uani 1 1 d . . .
F3 F 0.86281(16) 0.0025(2) 0.34672(10) 0.0625(7) Uani 1 1 d . . .
F4 F 0.65912(15) -0.13829(18) 0.54099(11) 0.0523(6) Uani 1 1 d . . .
F5 F 0.74153(16) -0.07632(19) 0.63161(10) 0.0506(6) Uani 1 1 d . . .
F6 F 0.79261(16) -0.20763(18) 0.57279(11) 0.0505(6) Uani 1 1 d . . .
O1 O 0.85081(17) 0.17108(19) 0.45395(10) 0.0367(6) Uani 1 1 d . . .
O2 O 0.74259(15) 0.09775(17) 0.54619(9) 0.0273(5) Uani 1 1 d . . .
N1 N 0.65329(19) 0.1849(2) 0.41826(12) 0.0304(6) Uani 1 1 d . . .
C1 C 0.5000 -0.0007(3) 0.2500 0.0199(8) Uani 1 2 d S . .
C2 C 0.6591(2) 0.2156(3) 0.35741(15) 0.0290(7) Uani 1 1 d . . .
H2 H 0.6991 0.2785 0.3517 0.035 Uiso 1 1 calc R . .
C3 C 0.6091(2) 0.1590(2) 0.30256(14) 0.0236(6) Uani 1 1 d . . .
C4 C 0.54926(18) 0.0643(2) 0.30747(14) 0.0215(6) Uani 1 1 d . . .
C5 C 0.54360(19) 0.0368(2) 0.37228(15) 0.0238(6) Uani 1 1 d . . .
C6 C 0.5947(2) 0.0982(3) 0.42524(16) 0.0294(7) Uani 1 1 d . . .
H6 H 0.5882 0.0783 0.4682 0.035 Uiso 1 1 calc R . .
C7 C 0.5000 -0.3866(4) 0.2500 0.0329(10) Uani 1 2 d S . .
C8 C 0.5804(2) -0.3263(3) 0.26543(15) 0.0317(7) Uani 1 1 d . . .
H8 H 0.6352 -0.3696 0.2756 0.038 Uiso 1 1 calc R . .
C9 C 0.5794(2) -0.2008(3) 0.26575(14) 0.0248(6) Uani 1 1 d . . .
C10 C 0.5000 -0.1331(3) 0.2500 0.0229(8) Uani 1 2 d S . .
C11 C 0.9171(3) 0.0155(3) 0.40572(18) 0.0416(8) Uani 1 1 d . . .
C12 C 0.8633(2) 0.0603(3) 0.45476(15) 0.0311(7) Uani 1 1 d . . .
C13 C 0.8302(2) -0.0289(3) 0.49172(16) 0.0324(7) Uani 1 1 d . . .
H13 H 0.8467 -0.1109 0.4874 0.039 Uiso 1 1 calc R . .
C14 C 0.7750(2) -0.0022(3) 0.53367(14) 0.0289(7) Uani 1 1 d . . .
C15 C 0.7429(2) -0.1081(3) 0.57010(17) 0.0367(8) Uani 1 1 d . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O2 1.9536(19) 7_656 ?
Cu1 O2 1.9536(19) . ?
Cu1 N1 2.125(3) . ?
Cu1 N1 2.125(3) 7_656 ?
Cu1 O1 2.175(2) . ?
Cu1 O1 2.175(2) 7_656 ?
Cl1 C3 1.727(3) . ?
Cl2 C5 1.726(3) . ?
Cl3 C7 1.733(4) . ?
Cl4 C9 1.728(3) . ?
F1 C11 1.324(4) . ?
F2 C11 1.330(4) . ?
F3 C11 1.334(4) . ?
F4 C15 1.338(4) . ?
F5 C15 1.336(4) . ?
F6 C15 1.332(4) . ?
O1 C12 1.238(4) . ?
O2 C14 1.262(4) . ?
N1 C2 1.337(4) . ?
N1 C6 1.342(4) . ?
C1 C4 1.458(3) 2_655 ?
C1 C4 1.458(3) . ?
C1 C10 1.462(5) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.409(4) . ?
C4 C5 1.408(4) . ?
C5 C6 1.384(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.376(4) 2_655 ?
C7 C8 1.376(4) . ?
C8 C9 1.386(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.405(3) . ?
C10 C9 1.405(3) 2_655 ?
C11 C12 1.532(5) . ?
C12 C13 1.413(4) . ?
C13 C14 1.377(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.533(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 180.000(1) 7_656 . ?
O2 Cu1 N1 90.06(9) 7_656 . ?
O2 Cu1 N1 89.94(9) . . ?
O2 Cu1 N1 89.94(9) 7_656 7_656 ?
O2 Cu1 N1 90.06(9) . 7_656 ?
N1 Cu1 N1 180.00(10) . 7_656 ?
O2 Cu1 O1 90.12(8) 7_656 . ?
O2 Cu1 O1 89.88(8) . . ?
N1 Cu1 O1 87.03(9) . . ?
N1 Cu1 O1 92.97(9) 7_656 . ?
O2 Cu1 O1 89.88(8) 7_656 7_656 ?
O2 Cu1 O1 90.12(8) . 7_656 ?
N1 Cu1 O1 92.97(9) . 7_656 ?
N1 Cu1 O1 87.03(9) 7_656 7_656 ?
O1 Cu1 O1 180.0 . 7_656 ?
C12 O1 Cu1 120.9(2) . . ?
C14 O2 Cu1 125.6(2) . . ?
C2 N1 C6 118.1(3) . . ?
C2 N1 Cu1 119.7(2) . . ?
C6 N1 Cu1 121.3(2) . . ?
C4 C1 C4 121.0(3) 2_655 . ?
C4 C1 C10 119.49(17) 2_655 . ?
C4 C1 C10 119.49(17) . . ?
N1 C2 C3 122.1(3) . . ?
N1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 Cl1 117.2(2) . . ?
C4 C3 Cl1 120.7(2) . . ?
C3 C4 C5 114.1(3) . . ?
C3 C4 C1 122.2(2) . . ?
C5 C4 C1 123.6(2) . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 Cl2 117.2(2) . . ?
C4 C5 Cl2 121.6(2) . . ?
N1 C6 C5 122.5(3) . . ?
N1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C8 C7 C8 122.1(4) 2_655 . ?
C8 C7 Cl3 118.96(19) 2_655 . ?
C8 C7 Cl3 118.96(19) . . ?
C7 C8 C9 118.4(3) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C8 C9 C10 122.7(3) . . ?
C8 C9 Cl4 117.4(2) . . ?
C10 C9 Cl4 119.8(2) . . ?
C9 C10 C9 115.7(4) 2_655 . ?
C9 C10 C1 122.15(18) 2_655 . ?
C9 C10 C1 122.15(18) . . ?
F1 C11 F2 106.5(3) . . ?
F1 C11 F3 106.7(3) . . ?
F2 C11 F3 108.3(3) . . ?
F1 C11 C12 112.0(3) . . ?
F2 C11 C12 113.6(3) . . ?
F3 C11 C12 109.4(3) . . ?
O1 C12 C13 128.5(3) . . ?
O1 C12 C11 114.5(3) . . ?
C13 C12 C11 116.9(3) . . ?
C14 C13 C12 122.9(3) . . ?
C14 C13 H13 118.5 . . ?
C12 C13 H13 118.5 . . ?
O2 C14 C13 130.1(3) . . ?
O2 C14 C15 112.3(3) . . ?
C13 C14 C15 117.5(3) . . ?
F6 C15 F5 107.8(3) . . ?
F6 C15 F4 107.3(3) . . ?
F5 C15 F4 106.5(3) . . ?
F6 C15 C14 114.0(3) . . ?
F5 C15 C14 110.6(3) . . ?
F4 C15 C14 110.3(3) . . ?

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
O2 Cu1 O1 C12 -165.3(2) 7_656 . . . ?
O2 Cu1 O1 C12 14.7(2) . . . . ?
N1 Cu1 O1 C12 -75.3(2) . . . . ?
N1 Cu1 O1 C12 104.7(2) 7_656 . . . ?
O1 Cu1 O1 C12 63(100) 7_656 . . . ?
O2 Cu1 O2 C14 -131(100) 7_656 . . . ?
N1 Cu1 O2 C14 74.0(2) . . . . ?
N1 Cu1 O2 C14 -106.0(2) 7_656 . . . ?
O1 Cu1 O2 C14 -13.0(2) . . . . ?
O1 Cu1 O2 C14 167.0(2) 7_656 . . . ?
O2 Cu1 N1 C2 35.0(2) 7_656 . . . ?
O2 Cu1 N1 C2 -145.0(2) . . . . ?
N1 Cu1 N1 C2 -173(100) 7_656 . . . ?
O1 Cu1 N1 C2 -55.1(2) . . . . ?
O1 Cu1 N1 C2 124.9(2) 7_656 . . . ?
O2 Cu1 N1 C6 -155.9(2) 7_656 . . . ?
O2 Cu1 N1 C6 24.1(2) . . . . ?
N1 Cu1 N1 C6 -4(100) 7_656 . . . ?
O1 Cu1 N1 C6 114.0(2) . . . . ?
O1 Cu1 N1 C6 -66.0(2) 7_656 . . . ?
C6 N1 C2 C3 -1.8(5) . . . . ?
Cu1 N1 C2 C3 167.7(2) . . . . ?
N1 C2 C3 C4 -0.6(5) . . . . ?
N1 C2 C3 Cl1 -175.7(2) . . . . ?
C2 C3 C4 C5 2.0(4) . . . . ?
Cl1 C3 C4 C5 176.9(2) . . . . ?
C2 C3 C4 C1 -176.4(3) . . . . ?
Cl1 C3 C4 C1 -1.5(4) . . . . ?
C4 C1 C4 C3 -49.4(2) 2_655 . . . ?
C10 C1 C4 C3 130.6(2) . . . . ?
C4 C1 C4 C5 132.4(3) 2_655 . . . ?
C10 C1 C4 C5 -47.6(3) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C1 C4 C5 C6 177.3(3) . . . . ?
C3 C4 C5 Cl2 177.3(2) . . . . ?
C1 C4 C5 Cl2 -4.3(4) . . . . ?
C2 N1 C6 C5 2.8(5) . . . . ?
Cu1 N1 C6 C5 -166.6(2) . . . . ?
C4 C5 C6 N1 -1.3(5) . . . . ?
Cl2 C5 C6 N1 -179.8(2) . . . . ?
C8 C7 C8 C9 0.49(19) 2_655 . . . ?
Cl3 C7 C8 C9 -179.51(19) . . . . ?
C7 C8 C9 C10 -1.0(4) . . . . ?
C7 C8 C9 Cl4 -177.28(18) . . . . ?
C8 C9 C10 C9 0.5(2) . . . 2_655 ?
Cl4 C9 C10 C9 176.7(2) . . . 2_655 ?
C8 C9 C10 C1 -179.5(2) . . . . ?
Cl4 C9 C10 C1 -3.3(2) . . . . ?
C4 C1 C10 C9 -51.59(18) 2_655 . . 2_655 ?
C4 C1 C10 C9 128.41(18) . . . 2_655 ?
C4 C1 C10 C9 128.41(18) 2_655 . . . ?
C4 C1 C10 C9 -51.59(18) . . . . ?
Cu1 O1 C12 C13 -11.4(5) . . . . ?
Cu1 O1 C12 C11 164.4(2) . . . . ?
F1 C11 C12 O1 35.4(4) . . . . ?
F2 C11 C12 O1 156.1(3) . . . . ?
F3 C11 C12 O1 -82.8(4) . . . . ?
F1 C11 C12 C13 -148.3(3) . . . . ?
F2 C11 C12 C13 -27.6(4) . . . . ?
F3 C11 C12 C13 93.6(4) . . . . ?
O1 C12 C13 C14 1.0(6) . . . . ?
C11 C12 C13 C14 -174.8(3) . . . . ?
Cu1 O2 C14 C13 7.9(5) . . . . ?
Cu1 O2 C14 C15 -169.4(2) . . . . ?
C12 C13 C14 O2 2.0(6) . . . . ?
C12 C13 C14 C15 179.2(3) . . . . ?
O2 C14 C15 F6 -162.8(3) . . . . ?
C13 C14 C15 F6 19.5(4) . . . . ?
O2 C14 C15 F5 -41.1(4) . . . . ?
C13 C14 C15 F5 141.2(3) . . . . ?
O2 C14 C15 F4 76.5(3) . . . . ?
C13 C14 C15 F4 -101.2(3) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_cubis_130K
_database_code_depnum_ccdc_archive 'CCDC 1884447'
_audit_update_record             
;
2019-01-14 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C27 H8 Cl7 Cu F12 N2 O4'
_chemical_formula_moiety         'C27 H8 Cl7 Cu F12 N2 O4'
_chemical_formula_weight         964.07
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_symmetry_equiv_pos_as_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                   15.3404(18)
_cell_length_b                   11.0521(10)
_cell_length_c                   20.930(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.584(6)
_cell_angle_gamma                90.0000
_cell_volume                     3463.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4544
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    130
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888.00
_exptl_absorpt_coefficient_mu    1.273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_T_max  0.963

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      130
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            13575
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         3.003
_diffrn_reflns_theta_full        27.490
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3956
_reflns_number_gt                3190
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_gt          0.1029
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3956
_refine_ls_number_parameters     243
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0512P)²+9.3724P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.7500 0.2500 0.5000 0.02424(14) Uani 1 2 d S . .
Cl1 Cl 0.87125(6) 0.20069(7) 0.77255(4) 0.0349(2) Uani 1 1 d . . .
Cl2 Cl 1.02936(6) -0.07231(8) 0.61151(4) 0.0371(2) Uani 1 1 d . . .
Cl3 Cl 1.0000 -0.54269(11) 0.7500 0.0650(5) Uani 1 2 d S . .
Cl4 Cl 1.18122(5) -0.12713(8) 0.78203(5) 0.0443(2) Uani 1 1 d . . .
F1 F 0.52099(16) 0.0946(2) 0.60073(12) 0.0586(6) Uani 1 1 d . . .
F2 F 0.5430(2) -0.0881(2) 0.57776(16) 0.0850(10) Uani 1 1 d . . .
F3 F 0.63748(18) 0.0052(3) 0.65297(11) 0.0730(8) Uani 1 1 d . . .
F4 F 0.84086(17) -0.1378(2) 0.45847(13) 0.0595(7) Uani 1 1 d . . .
F5 F 0.75849(18) -0.0754(2) 0.36831(11) 0.0578(6) Uani 1 1 d . . .
F6 F 0.70738(18) -0.2065(2) 0.42721(12) 0.0579(7) Uani 1 1 d . . .
O1 O 0.65108(18) 0.1715(2) 0.54614(11) 0.0410(6) Uani 1 1 d . . .
O2 O 0.75814(16) 0.09791(19) 0.45393(10) 0.0314(5) Uani 1 1 d . . .
N1 N 0.8486(2) 0.1851(2) 0.58213(13) 0.0348(7) Uani 1 1 d . . .
C1 C 1.0000 -0.0001(4) 0.7500 0.0235(8) Uani 1 2 d S . .
C2 C 0.8418(2) 0.2156(3) 0.64294(16) 0.0339(8) Uani 1 1 d . . .
H2 H 0.8014 0.2779 0.6485 0.041 Uiso 1 1 calc R . .
C3 C 0.8917(2) 0.1592(3) 0.69751(15) 0.0272(7) Uani 1 1 d . . .
C4 C 0.9508(2) 0.0648(2) 0.69273(15) 0.0235(6) Uani 1 1 d . . .
C5 C 0.9567(2) 0.0363(3) 0.62828(16) 0.0280(7) Uani 1 1 d . . .
C6 C 0.9062(2) 0.0981(3) 0.57545(17) 0.0321(7) Uani 1 1 d . . .
H6 H 0.9129 0.0777 0.5327 0.039 Uiso 1 1 calc R . .
C7 C 1.0000 -0.3858(4) 0.7500 0.0392(12) Uani 1 2 d S . .
C8 C 1.0800(3) -0.3254(3) 0.76553(16) 0.0370(8) Uani 1 1 d . . .
H8 H 1.1348 -0.3686 0.7759 0.044 Uiso 1 1 calc R . .
C9 C 1.0791(2) -0.2003(3) 0.76578(15) 0.0275(6) Uani 1 1 d . . .
C10 C 1.0000 -0.1328(4) 0.7500 0.0247(9) Uani 1 2 d S . .
C11 C 0.5835(3) 0.0168(4) 0.5941(2) 0.0490(10) Uani 1 1 d . . .
C12 C 0.6380(2) 0.0606(3) 0.54546(16) 0.0352(8) Uani 1 1 d . . .
C13 C 0.6708(2) -0.0283(3) 0.50816(16) 0.0361(8) Uani 1 1 d . . .
H13 H 0.6542 -0.1102 0.5123 0.043 Uiso 1 1 calc R . .
C14 C 0.7256(2) -0.0017(3) 0.46622(15) 0.0314(7) Uani 1 1 d . . .
C15 C 0.7580(3) -0.1075(3) 0.42979(19) 0.0437(9) Uani 1 1 d . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O2 1.955(2) . ?
Cu1 O2 1.955(2) 7_656 ?
Cu1 O1 2.151(3) 7_656 ?
Cu1 O1 2.151(3) . ?
Cu1 N1 2.151(3) 7_656 ?
Cu1 N1 2.151(3) . ?
Cl1 C3 1.729(3) . ?
Cl2 C5 1.726(3) . ?
Cl3 C7 1.734(4) . ?
Cl4 C9 1.730(3) . ?
F1 C11 1.318(4) . ?
F2 C11 1.325(5) . ?
F3 C11 1.333(5) . ?
F4 C15 1.325(5) . ?
F5 C15 1.336(4) . ?
F6 C15 1.336(4) . ?
O1 C12 1.241(4) . ?
O2 C14 1.258(4) . ?
N1 C6 1.334(4) . ?
N1 C2 1.343(4) . ?
C1 C4 1.458(4) . ?
C1 C4 1.458(4) 2_756 ?
C1 C10 1.467(5) . ?
C2 C3 1.378(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(4) . ?
C4 C5 1.407(4) . ?
C5 C6 1.384(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.372(4) . ?
C7 C8 1.372(4) 2_756 ?
C8 C9 1.383(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.400(4) . ?
C10 C9 1.400(4) 2_756 ?
C11 C12 1.529(5) . ?
C12 C13 1.414(5) . ?
C13 C14 1.373(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.537(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 180.00(11) . 7_656 ?
O2 Cu1 O1 89.89(9) . 7_656 ?
O2 Cu1 O1 90.11(9) 7_656 7_656 ?
O2 Cu1 O1 90.11(9) . . ?
O2 Cu1 O1 89.89(9) 7_656 . ?
O1 Cu1 O1 180.00(9) 7_656 . ?
O2 Cu1 N1 90.12(9) . 7_656 ?
O2 Cu1 N1 89.88(9) 7_656 7_656 ?
O1 Cu1 N1 87.07(10) 7_656 7_656 ?
O1 Cu1 N1 92.93(10) . 7_656 ?
O2 Cu1 N1 89.88(9) . . ?
O2 Cu1 N1 90.12(9) 7_656 . ?
O1 Cu1 N1 92.93(10) 7_656 . ?
O1 Cu1 N1 87.07(10) . . ?
N1 Cu1 N1 180.00(11) 7_656 . ?
C12 O1 Cu1 121.4(2) . . ?
C14 O2 Cu1 125.5(2) . . ?
C6 N1 C2 118.1(3) . . ?
C6 N1 Cu1 121.6(2) . . ?
C2 N1 Cu1 119.1(2) . . ?
C4 C1 C4 121.1(4) . 2_756 ?
C4 C1 C10 119.45(18) . . ?
C4 C1 C10 119.45(18) 2_756 . ?
N1 C2 C3 121.8(3) . . ?
N1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C2 C3 C4 122.0(3) . . ?
C2 C3 Cl1 117.0(2) . . ?
C4 C3 Cl1 120.7(2) . . ?
C3 C4 C5 114.4(3) . . ?
C3 C4 C1 122.3(3) . . ?
C5 C4 C1 123.3(3) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 Cl2 117.0(2) . . ?
C4 C5 Cl2 122.0(2) . . ?
N1 C6 C5 122.7(3) . . ?
N1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C8 C7 C8 121.8(4) . 2_756 ?
C8 C7 Cl3 119.1(2) . . ?
C8 C7 Cl3 119.1(2) 2_756 . ?
C7 C8 C9 118.6(3) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C8 C9 C10 122.7(3) . . ?
C8 C9 Cl4 117.3(3) . . ?
C10 C9 Cl4 119.9(2) . . ?
C9 C10 C9 115.7(4) 2_756 . ?
C9 C10 C1 122.14(19) 2_756 . ?
C9 C10 C1 122.14(19) . . ?
F1 C11 F2 106.6(4) . . ?
F1 C11 F3 106.5(3) . . ?
F2 C11 F3 108.4(4) . . ?
F1 C11 C12 112.3(3) . . ?
F2 C11 C12 113.5(3) . . ?
F3 C11 C12 109.1(3) . . ?
O1 C12 C13 128.0(3) . . ?
O1 C12 C11 114.6(3) . . ?
C13 C12 C11 117.4(3) . . ?
C14 C13 C12 123.1(3) . . ?
C14 C13 H13 118.5 . . ?
C12 C13 H13 118.5 . . ?
O2 C14 C13 130.1(3) . . ?
O2 C14 C15 112.3(3) . . ?
C13 C14 C15 117.6(3) . . ?
F4 C15 F6 107.6(3) . . ?
F4 C15 F5 107.3(3) . . ?
F6 C15 F5 107.7(3) . . ?
F4 C15 C14 110.5(3) . . ?
F6 C15 C14 113.3(3) . . ?
F5 C15 C14 110.3(3) . . ?

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
O2 Cu1 O1 C12 14.1(3) . . . . ?
O2 Cu1 O1 C12 -165.9(3) 7_656 . . . ?
O1 Cu1 O1 C12 -144(100) 7_656 . . . ?
N1 Cu1 O1 C12 104.2(3) 7_656 . . . ?
N1 Cu1 O1 C12 -75.8(3) . . . . ?
O2 Cu1 O2 C14 64(100) 7_656 . . . ?
O1 Cu1 O2 C14 167.8(3) 7_656 . . . ?
O1 Cu1 O2 C14 -12.2(3) . . . . ?
N1 Cu1 O2 C14 -105.1(3) 7_656 . . . ?
N1 Cu1 O2 C14 74.9(3) . . . . ?
O2 Cu1 N1 C6 22.8(3) . . . . ?
O2 Cu1 N1 C6 -157.2(3) 7_656 . . . ?
O1 Cu1 N1 C6 -67.1(3) 7_656 . . . ?
O1 Cu1 N1 C6 112.9(3) . . . . ?
N1 Cu1 N1 C6 176(100) 7_656 . . . ?
O2 Cu1 N1 C2 -144.5(3) . . . . ?
O2 Cu1 N1 C2 35.5(3) 7_656 . . . ?
O1 Cu1 N1 C2 125.6(3) 7_656 . . . ?
O1 Cu1 N1 C2 -54.4(3) . . . . ?
N1 Cu1 N1 C2 8(100) 7_656 . . . ?
C6 N1 C2 C3 -0.5(5) . . . . ?
Cu1 N1 C2 C3 167.3(3) . . . . ?
N1 C2 C3 C4 -1.6(5) . . . . ?
N1 C2 C3 Cl1 -176.1(3) . . . . ?
C2 C3 C4 C5 2.1(4) . . . . ?
Cl1 C3 C4 C5 176.3(2) . . . . ?
C2 C3 C4 C1 -176.3(3) . . . . ?
Cl1 C3 C4 C1 -2.1(4) . . . . ?
C4 C1 C4 C3 -49.1(2) 2_756 . . . ?
C10 C1 C4 C3 130.9(2) . . . . ?
C4 C1 C4 C5 132.6(3) 2_756 . . . ?
C10 C1 C4 C5 -47.4(3) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C1 C4 C5 C6 177.8(3) . . . . ?
C3 C4 C5 Cl2 177.0(2) . . . . ?
C1 C4 C5 Cl2 -4.6(4) . . . . ?
C2 N1 C6 C5 2.0(5) . . . . ?
Cu1 N1 C6 C5 -165.5(2) . . . . ?
C4 C5 C6 N1 -1.4(5) . . . . ?
Cl2 C5 C6 N1 -179.1(3) . . . . ?
C8 C7 C8 C9 0.4(2) 2_756 . . . ?
Cl3 C7 C8 C9 -179.6(2) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C7 C8 C9 Cl4 -177.2(2) . . . . ?
C8 C9 C10 C9 0.4(2) . . . 2_756 ?
Cl4 C9 C10 C9 176.7(3) . . . 2_756 ?
C8 C9 C10 C1 -179.6(2) . . . . ?
Cl4 C9 C10 C1 -3.3(3) . . . . ?
C4 C1 C10 C9 -51.37(19) . . . 2_756 ?
C4 C1 C10 C9 128.63(19) 2_756 . . 2_756 ?
C4 C1 C10 C9 128.63(19) . . . . ?
C4 C1 C10 C9 -51.37(19) 2_756 . . . ?
Cu1 O1 C12 C13 -11.1(5) . . . . ?
Cu1 O1 C12 C11 165.4(2) . . . . ?
F1 C11 C12 O1 35.8(5) . . . . ?
F2 C11 C12 O1 156.8(3) . . . . ?
F3 C11 C12 O1 -82.1(4) . . . . ?
F1 C11 C12 C13 -147.4(3) . . . . ?
F2 C11 C12 C13 -26.3(5) . . . . ?
F3 C11 C12 C13 94.8(4) . . . . ?
O1 C12 C13 C14 1.0(6) . . . . ?
C11 C12 C13 C14 -175.4(3) . . . . ?
Cu1 O2 C14 C13 7.1(5) . . . . ?
Cu1 O2 C14 C15 -169.7(2) . . . . ?
C12 C13 C14 O2 2.1(6) . . . . ?
C12 C13 C14 C15 178.7(3) . . . . ?
O2 C14 C15 F4 76.5(4) . . . . ?
C13 C14 C15 F4 -100.8(4) . . . . ?
O2 C14 C15 F6 -162.7(3) . . . . ?
C13 C14 C15 F6 20.1(5) . . . . ?
O2 C14 C15 F5 -41.9(4) . . . . ?
C13 C14 C15 F5 140.8(3) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_cubis_150K
_database_code_depnum_ccdc_archive 'CCDC 1884449'
_audit_update_record             
;
2019-01-14 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C27 H8 Cl7 Cu F12 N2 O4'
_chemical_formula_moiety         'C27 H8 Cl7 Cu F12 N2 O4'
_chemical_formula_weight         964.07
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_symmetry_equiv_pos_as_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                   15.3536(19)
_cell_length_b                   11.0690(11)
_cell_length_c                   20.979(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.497(6)
_cell_angle_gamma                90.0000
_cell_volume                     3480.9(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4477
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    150
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888.00
_exptl_absorpt_coefficient_mu    1.266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_T_max  0.963

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      150
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            13656
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         3.001
_diffrn_reflns_theta_full        27.480
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3971
_reflns_number_gt                3173
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1123
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3971
_refine_ls_number_parameters     243
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0548P)²+8.9967P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.40
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.2500 0.2500 0.5000 0.02674(16) Uani 1 2 d S . .
Cl1 Cl 0.12864(6) 0.20104(8) 0.22767(4) 0.0391(2) Uani 1 1 d . . .
Cl2 Cl -0.02955(6) -0.07253(8) 0.38812(5) 0.0414(2) Uani 1 1 d . . .
Cl3 Cl 0.0000 -0.54173(12) 0.2500 0.0728(6) Uani 1 2 d S . .
Cl4 Cl 0.18101(6) -0.12699(9) 0.28211(6) 0.0496(3) Uani 1 1 d . . .
F1 F 0.47809(18) 0.0957(3) 0.39978(13) 0.0677(8) Uani 1 1 d . . .
F2 F 0.4556(3) -0.0867(3) 0.42180(18) 0.0981(12) Uani 1 1 d . . .
F3 F 0.3622(2) 0.0079(3) 0.34728(13) 0.0829(10) Uani 1 1 d . . .
F4 F 0.15896(19) -0.1380(2) 0.54205(14) 0.0681(8) Uani 1 1 d . . .
F5 F 0.2414(2) -0.0754(2) 0.63163(12) 0.0652(8) Uani 1 1 d . . .
F6 F 0.2926(2) -0.2055(2) 0.57273(13) 0.0672(8) Uani 1 1 d . . .
O1 O 0.3474(2) 0.1723(2) 0.45395(12) 0.0440(7) Uani 1 1 d . . .
O2 O 0.24111(17) 0.0979(2) 0.54602(11) 0.0339(5) Uani 1 1 d . . .
N1 N 0.1508(2) 0.1854(3) 0.41749(14) 0.0388(7) Uani 1 1 d . . .
C1 C 0.0000 -0.0002(4) 0.2500 0.0249(9) Uani 1 2 d S . .
C2 C 0.1570(3) 0.2157(3) 0.35715(17) 0.0369(8) Uani 1 1 d . . .
H2 H 0.1967 0.2788 0.3517 0.044 Uiso 1 1 calc R . .
C3 C 0.1082(2) 0.1594(3) 0.30241(17) 0.0304(7) Uani 1 1 d . . .
C4 C 0.0491(2) 0.0649(3) 0.30724(16) 0.0263(7) Uani 1 1 d . . .
C5 C 0.0432(2) 0.0368(3) 0.37156(17) 0.0308(7) Uani 1 1 d . . .
C6 C 0.0929(3) 0.0985(3) 0.42412(18) 0.0364(8) Uani 1 1 d . . .
H6 H 0.0857 0.0785 0.4667 0.044 Uiso 1 1 calc R . .
C7 C 0.0000 -0.3851(4) 0.2500 0.0423(13) Uani 1 2 d S . .
C8 C 0.0796(3) -0.3249(3) 0.26549(18) 0.0409(9) Uani 1 1 d . . .
H8 H 0.1344 -0.3682 0.2757 0.049 Uiso 1 1 calc R . .
C9 C 0.0790(2) -0.1999(3) 0.26596(17) 0.0317(7) Uani 1 1 d . . .
C10 C 0.0000 -0.1331(4) 0.2500 0.0258(9) Uani 1 2 d S . .
C11 C 0.4155(3) 0.0183(4) 0.4062(2) 0.0526(10) Uani 1 1 d . . .
C12 C 0.3608(3) 0.0613(3) 0.45465(17) 0.0390(8) Uani 1 1 d . . .
C13 C 0.3285(3) -0.0275(3) 0.49177(18) 0.0411(9) Uani 1 1 d . . .
H13 H 0.3457 -0.1091 0.4877 0.049 Uiso 1 1 calc R . .
C14 C 0.2734(2) -0.0019(3) 0.53362(16) 0.0346(8) Uani 1 1 d . . .
C15 C 0.2418(3) -0.1072(3) 0.5703(2) 0.0488(10) Uani 1 1 d . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O2 1.960(2) . ?
Cu1 O2 1.960(2) 7_556 ?
Cu1 O1 2.129(3) . ?
Cu1 O1 2.129(3) 7_556 ?
Cu1 N1 2.165(3) 7_556 ?
Cu1 N1 2.165(3) . ?
Cl1 C3 1.727(3) . ?
Cl2 C5 1.732(3) . ?
Cl3 C7 1.733(5) . ?
Cl4 C9 1.729(4) . ?
F1 C11 1.316(5) . ?
F2 C11 1.322(5) . ?
F3 C11 1.332(5) . ?
F4 C15 1.327(5) . ?
F5 C15 1.335(5) . ?
F6 C15 1.333(5) . ?
O1 C12 1.245(4) . ?
O2 C14 1.262(4) . ?
N1 C2 1.333(4) . ?
N1 C6 1.338(4) . ?
C1 C4 1.462(4) . ?
C1 C4 1.462(4) 2 ?
C1 C10 1.471(6) . ?
C2 C3 1.377(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.402(4) . ?
C4 C5 1.407(5) . ?
C5 C6 1.378(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.369(5) . ?
C7 C8 1.369(5) 2 ?
C8 C9 1.384(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.398(4) . ?
C10 C9 1.398(4) 2 ?
C11 C12 1.528(6) . ?
C12 C13 1.409(5) . ?
C13 C14 1.374(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.533(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 180.0 . 7_556 ?
O2 Cu1 O1 90.42(10) . . ?
O2 Cu1 O1 89.58(10) 7_556 . ?
O2 Cu1 O1 89.58(10) . 7_556 ?
O2 Cu1 O1 90.42(10) 7_556 7_556 ?
O1 Cu1 O1 180.000(1) . 7_556 ?
O2 Cu1 N1 90.10(10) . 7_556 ?
O2 Cu1 N1 89.90(10) 7_556 7_556 ?
O1 Cu1 N1 93.14(11) . 7_556 ?
O1 Cu1 N1 86.86(11) 7_556 7_556 ?
O2 Cu1 N1 89.90(10) . . ?
O2 Cu1 N1 90.10(10) 7_556 . ?
O1 Cu1 N1 86.86(11) . . ?
O1 Cu1 N1 93.14(11) 7_556 . ?
N1 Cu1 N1 180.0 7_556 . ?
C12 O1 Cu1 121.6(2) . . ?
C14 O2 Cu1 125.3(2) . . ?
C2 N1 C6 117.8(3) . . ?
C2 N1 Cu1 119.6(2) . . ?
C6 N1 Cu1 121.5(2) . . ?
C4 C1 C4 120.9(4) . 2 ?
C4 C1 C10 119.53(18) . . ?
C4 C1 C10 119.53(18) 2 . ?
N1 C2 C3 122.7(3) . . ?
N1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 Cl1 117.6(2) . . ?
C4 C3 Cl1 120.8(3) . . ?
C3 C4 C5 114.3(3) . . ?
C3 C4 C1 122.4(3) . . ?
C5 C4 C1 123.3(3) . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 Cl2 117.1(3) . . ?
C4 C5 Cl2 121.7(3) . . ?
N1 C6 C5 122.6(3) . . ?
N1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C8 C7 C8 121.7(4) . 2 ?
C8 C7 Cl3 119.1(2) . . ?
C8 C7 Cl3 119.1(2) 2 . ?
C7 C8 C9 118.8(4) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C8 C9 C10 122.3(3) . . ?
C8 C9 Cl4 117.4(3) . . ?
C10 C9 Cl4 120.1(3) . . ?
C9 C10 C9 116.1(4) 2 . ?
C9 C10 C1 121.9(2) 2 . ?
C9 C10 C1 121.9(2) . . ?
F2 C11 F3 108.3(4) . . ?
F2 C11 F1 106.7(4) . . ?
F3 C11 F1 106.0(4) . . ?
F2 C11 C12 113.8(4) . . ?
F3 C11 C12 109.2(4) . . ?
F1 C11 C12 112.6(4) . . ?
O1 C12 C13 128.2(4) . . ?
O1 C12 C11 114.4(3) . . ?
C13 C12 C11 117.3(3) . . ?
C14 C13 C12 123.2(3) . . ?
C14 C13 H13 118.4 . . ?
C12 C13 H13 118.4 . . ?
O2 C14 C13 129.5(3) . . ?
O2 C14 C15 112.4(3) . . ?
C13 C14 C15 118.0(3) . . ?
F4 C15 F6 107.7(3) . . ?
F4 C15 F5 107.1(4) . . ?
F6 C15 F5 107.7(3) . . ?
F4 C15 C14 110.3(3) . . ?
F6 C15 C14 113.2(4) . . ?
F5 C15 C14 110.6(3) . . ?

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
O2 Cu1 O1 C12 13.6(3) . . . . ?
O2 Cu1 O1 C12 -166.4(3) 7_556 . . . ?
O1 Cu1 O1 C12 -108(100) 7_556 . . . ?
N1 Cu1 O1 C12 103.7(3) 7_556 . . . ?
N1 Cu1 O1 C12 -76.3(3) . . . . ?
O2 Cu1 O2 C14 162(100) 7_556 . . . ?
O1 Cu1 O2 C14 -12.0(3) . . . . ?
O1 Cu1 O2 C14 168.0(3) 7_556 . . . ?
N1 Cu1 O2 C14 -105.2(3) 7_556 . . . ?
N1 Cu1 O2 C14 74.8(3) . . . . ?
O2 Cu1 N1 C2 -145.0(3) . . . . ?
O2 Cu1 N1 C2 35.0(3) 7_556 . . . ?
O1 Cu1 N1 C2 -54.6(3) . . . . ?
O1 Cu1 N1 C2 125.4(3) 7_556 . . . ?
N1 Cu1 N1 C2 118(100) 7_556 . . . ?
O2 Cu1 N1 C6 22.7(3) . . . . ?
O2 Cu1 N1 C6 -157.3(3) 7_556 . . . ?
O1 Cu1 N1 C6 113.1(3) . . . . ?
O1 Cu1 N1 C6 -66.9(3) 7_556 . . . ?
N1 Cu1 N1 C6 -74(100) 7_556 . . . ?
C6 N1 C2 C3 -1.7(6) . . . . ?
Cu1 N1 C2 C3 166.4(3) . . . . ?
N1 C2 C3 C4 -0.6(6) . . . . ?
N1 C2 C3 Cl1 -175.7(3) . . . . ?
C2 C3 C4 C5 1.6(5) . . . . ?
Cl1 C3 C4 C5 176.6(2) . . . . ?
C2 C3 C4 C1 -176.9(3) . . . . ?
Cl1 C3 C4 C1 -2.0(4) . . . . ?
C4 C1 C4 C3 -49.0(3) 2 . . . ?
C10 C1 C4 C3 131.0(3) . . . . ?
C4 C1 C4 C5 132.6(3) 2 . . . ?
C10 C1 C4 C5 -47.4(3) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C1 C4 C5 C6 178.0(3) . . . . ?
C3 C4 C5 Cl2 177.2(2) . . . . ?
C1 C4 C5 Cl2 -4.3(4) . . . . ?
C2 N1 C6 C5 2.9(6) . . . . ?
Cu1 N1 C6 C5 -165.0(3) . . . . ?
C4 C5 C6 N1 -1.8(6) . . . . ?
Cl2 C5 C6 N1 -179.6(3) . . . . ?
C8 C7 C8 C9 0.6(2) 2 . . . ?
Cl3 C7 C8 C9 -179.4(2) . . . . ?
C7 C8 C9 C10 -1.2(5) . . . . ?
C7 C8 C9 Cl4 -177.1(2) . . . . ?
C8 C9 C10 C9 0.6(2) . . . 2 ?
Cl4 C9 C10 C9 176.4(3) . . . 2 ?
C8 C9 C10 C1 -179.4(2) . . . . ?
Cl4 C9 C10 C1 -3.6(3) . . . . ?
C4 C1 C10 C9 128.9(2) . . . 2 ?
C4 C1 C10 C9 -51.1(2) 2 . . 2 ?
C4 C1 C10 C9 -51.1(2) . . . . ?
C4 C1 C10 C9 128.9(2) 2 . . . ?
Cu1 O1 C12 C13 -10.8(5) . . . . ?
Cu1 O1 C12 C11 165.9(3) . . . . ?
F2 C11 C12 O1 157.5(4) . . . . ?
F3 C11 C12 O1 -81.4(4) . . . . ?
F1 C11 C12 O1 36.0(5) . . . . ?
F2 C11 C12 C13 -25.4(6) . . . . ?
F3 C11 C12 C13 95.7(4) . . . . ?
F1 C11 C12 C13 -146.9(4) . . . . ?
O1 C12 C13 C14 1.3(7) . . . . ?
C11 C12 C13 C14 -175.3(4) . . . . ?
Cu1 O2 C14 C13 7.4(5) . . . . ?
Cu1 O2 C14 C15 -170.4(2) . . . . ?
C12 C13 C14 O2 1.4(7) . . . . ?
C12 C13 C14 C15 179.0(4) . . . . ?
O2 C14 C15 F4 76.8(4) . . . . ?
C13 C14 C15 F4 -101.3(4) . . . . ?
O2 C14 C15 F6 -162.4(3) . . . . ?
C13 C14 C15 F6 19.5(5) . . . . ?
O2 C14 C15 F5 -41.5(5) . . . . ?
C13 C14 C15 F5 140.4(4) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_cubis_298K
_database_code_depnum_ccdc_archive 'CCDC 1884450'
_audit_update_record             
;
2019-01-14 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C27 H8 Cl7 Cu F12 N2 O4'
_chemical_formula_moiety         'C27 H8 Cl7 Cu F12 N2 O4'
_chemical_formula_weight         964.07
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_symmetry_equiv_pos_as_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                   15.566(14)
_cell_length_b                   11.161(9)
_cell_length_c                   21.302(16)
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.022(14)
_cell_angle_gamma                90.0000
_cell_volume                     3620(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4259
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    298
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888.00
_exptl_absorpt_coefficient_mu    1.218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_T_max  0.964

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      298
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            14086
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_av_R_equivalents  0.0929
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         3.168
_diffrn_reflns_theta_full        27.470
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4092
_reflns_number_gt                2775
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1377
_refine_ls_R_factor_gt           0.0943
_refine_ls_wR_factor_ref         0.2281
_refine_ls_wR_factor_gt          0.2029
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4092
_refine_ls_number_parameters     243
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0847P)²+11.3251P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.2500 0.2500 0.5000 0.0477(3) Uani 1 2 d S . .
Cl1 Cl 0.12740(13) 0.20265(16) 0.22869(8) 0.0651(5) Uani 1 1 d . . .
Cl2 Cl -0.02935(13) -0.07282(17) 0.38614(9) 0.0725(6) Uani 1 1 d . . .
Cl3 Cl 0.0000 -0.5351(3) 0.2500 0.144(2) Uani 1 2 d S . .
Cl4 Cl 0.17876(12) -0.12552(19) 0.28170(12) 0.0889(7) Uani 1 1 d . . .
F1 F 0.4724(4) 0.0990(7) 0.4034(3) 0.137(2) Uani 1 1 d . . .
F2 F 0.4447(7) -0.0779(7) 0.4179(5) 0.204(5) Uani 1 1 d . . .
F3 F 0.3608(5) 0.0225(9) 0.3492(3) 0.167(3) Uani 1 1 d . . .
F4 F 0.1608(5) -0.1364(5) 0.5454(4) 0.136(2) Uani 1 1 d . . .
F5 F 0.2421(5) -0.0718(5) 0.6310(3) 0.125(2) Uani 1 1 d . . .
F6 F 0.2932(5) -0.1985(5) 0.5738(3) 0.130(2) Uani 1 1 d . . .
O1 O 0.3384(3) 0.1745(4) 0.4542(2) 0.0677(13) Uani 1 1 d . . .
O2 O 0.2380(3) 0.0986(4) 0.5453(2) 0.0572(11) Uani 1 1 d . . .
N1 N 0.1444(4) 0.1866(5) 0.4150(2) 0.0603(15) Uani 1 1 d . . .
C1 C 0.0000 0.0010(7) 0.2500 0.0373(16) Uani 1 2 d S . .
C2 C 0.1516(5) 0.2164(5) 0.3558(3) 0.0588(18) Uani 1 1 d . . .
H2 H 0.1894 0.2785 0.3507 0.071 Uiso 1 1 calc R . .
C3 C 0.1057(4) 0.1597(5) 0.3015(3) 0.0465(14) Uani 1 1 d . . .
C4 C 0.0478(4) 0.0647(5) 0.3062(3) 0.0392(12) Uani 1 1 d . . .
C5 C 0.0402(4) 0.0371(5) 0.3690(3) 0.0467(14) Uani 1 1 d . . .
C6 C 0.0881(5) 0.1000(6) 0.4209(3) 0.0572(16) Uani 1 1 d . . .
H6 H 0.0803 0.0806 0.4618 0.069 Uiso 1 1 calc R . .
C7 C 0.0000 -0.3801(8) 0.2500 0.080(4) Uani 1 2 d S . .
C8 C 0.0791(6) -0.3208(6) 0.2655(4) 0.074(2) Uani 1 1 d . . .
H8 H 0.1318 -0.3627 0.2756 0.089 Uiso 1 1 calc R . .
C9 C 0.0778(5) -0.1979(6) 0.2658(3) 0.0558(16) Uani 1 1 d . . .
C10 C 0.0000 -0.1307(7) 0.2500 0.0456(19) Uani 1 2 d S . .
C11 C 0.4099(8) 0.0265(9) 0.4073(5) 0.099(3) Uani 1 1 d . . .
C12 C 0.3545(5) 0.0646(7) 0.4554(3) 0.0648(18) Uani 1 1 d . . .
C13 C 0.3247(5) -0.0232(7) 0.4914(4) 0.072(2) Uani 1 1 d . . .
H13 H 0.3417 -0.1021 0.4868 0.086 Uiso 1 1 calc R . .
C14 C 0.2708(4) 0.0009(6) 0.5337(3) 0.0561(16) Uani 1 1 d . . .
C15 C 0.2417(7) -0.1028(7) 0.5712(4) 0.083(3) Uani 1 1 d . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O2 1.974(4) 7_556 ?
Cu1 O2 1.974(4) . ?
Cu1 O1 2.029(5) . ?
Cu1 O1 2.029(5) 7_556 ?
Cu1 N1 2.289(6) 7_556 ?
Cu1 N1 2.289(6) . ?
Cl1 C3 1.723(6) . ?
Cl2 C5 1.725(6) . ?
Cl3 C7 1.730(10) . ?
Cl4 C9 1.737(8) . ?
F1 C11 1.281(11) . ?
F2 C11 1.285(11) . ?
F3 C11 1.312(12) . ?
F4 C15 1.319(11) . ?
F5 C15 1.319(10) . ?
F6 C15 1.330(10) . ?
O1 C12 1.251(8) . ?
O2 C14 1.251(8) . ?
N1 C6 1.328(8) . ?
N1 C2 1.332(8) . ?
C1 C4 1.456(7) . ?
C1 C4 1.456(7) 2 ?
C1 C10 1.470(11) . ?
C2 C3 1.380(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.408(8) . ?
C4 C5 1.401(8) . ?
C5 C6 1.389(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(10) . ?
C7 C8 1.376(10) 2 ?
C8 C9 1.372(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.404(8) . ?
C10 C9 1.404(8) 2 ?
C11 C12 1.531(12) . ?
C12 C13 1.382(10) . ?
C13 C14 1.379(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.528(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 180.000(1) 7_556 . ?
O2 Cu1 O1 88.72(19) 7_556 . ?
O2 Cu1 O1 91.28(19) . . ?
O2 Cu1 O1 91.28(19) 7_556 7_556 ?
O2 Cu1 O1 88.72(19) . 7_556 ?
O1 Cu1 O1 180.0(2) . 7_556 ?
O2 Cu1 N1 89.83(19) 7_556 7_556 ?
O2 Cu1 N1 90.17(19) . 7_556 ?
O1 Cu1 N1 93.5(2) . 7_556 ?
O1 Cu1 N1 86.5(2) 7_556 7_556 ?
O2 Cu1 N1 90.17(19) 7_556 . ?
O2 Cu1 N1 89.83(19) . . ?
O1 Cu1 N1 86.5(2) . . ?
O1 Cu1 N1 93.5(2) 7_556 . ?
N1 Cu1 N1 180.000(1) 7_556 . ?
C12 O1 Cu1 123.4(5) . . ?
C14 O2 Cu1 124.4(4) . . ?
C6 N1 C2 117.3(6) . . ?
C6 N1 Cu1 122.0(4) . . ?
C2 N1 Cu1 118.9(5) . . ?
C4 C1 C4 121.6(6) . 2 ?
C4 C1 C10 119.2(3) . . ?
C4 C1 C10 119.2(3) 2 . ?
N1 C2 C3 123.2(6) . . ?
N1 C2 H2 118.4 . . ?
C3 C2 H2 118.4 . . ?
C2 C3 C4 120.9(5) . . ?
C2 C3 Cl1 117.5(5) . . ?
C4 C3 Cl1 121.5(5) . . ?
C5 C4 C3 114.6(5) . . ?
C5 C4 C1 123.2(5) . . ?
C3 C4 C1 122.3(5) . . ?
C4 C5 C6 120.7(5) . . ?
C4 C5 Cl2 122.7(5) . . ?
C6 C5 Cl2 116.6(4) . . ?
N1 C6 C5 123.2(6) . . ?
N1 C6 H6 118.4 . . ?
C5 C6 H6 118.4 . . ?
C8 C7 C8 122.4(9) . 2 ?
C8 C7 Cl3 118.8(5) . . ?
C8 C7 Cl3 118.8(5) 2 . ?
C9 C8 C7 118.0(8) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C8 C9 C10 123.1(7) . . ?
C8 C9 Cl4 116.9(6) . . ?
C10 C9 Cl4 119.9(5) . . ?
C9 C10 C9 115.4(8) . 2 ?
C9 C10 C1 122.3(4) . . ?
C9 C10 C1 122.3(4) 2 . ?
F2 C11 F3 106.1(10) . . ?
F2 C11 F1 106.7(11) . . ?
F3 C11 F1 105.2(9) . . ?
F2 C11 C12 114.2(8) . . ?
F3 C11 C12 110.0(9) . . ?
F1 C11 C12 114.1(8) . . ?
O1 C12 C13 128.1(7) . . ?
O1 C12 C11 113.4(7) . . ?
C13 C12 C11 118.4(7) . . ?
C12 C13 C14 123.0(7) . . ?
C12 C13 H13 118.5 . . ?
C14 C13 H13 118.5 . . ?
O2 C14 C13 129.0(6) . . ?
O2 C14 C15 112.2(6) . . ?
C13 C14 C15 118.8(7) . . ?
F5 C15 F6 106.7(7) . . ?
F5 C15 F4 106.9(9) . . ?
F6 C15 F4 107.7(8) . . ?
F5 C15 C14 111.4(7) . . ?
F6 C15 C14 112.8(8) . . ?
F4 C15 C14 111.0(7) . . ?

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
O2 Cu1 O1 C12 -170.2(5) 7_556 . . . ?
O2 Cu1 O1 C12 9.8(5) . . . . ?
O1 Cu1 O1 C12 -52(100) 7_556 . . . ?
N1 Cu1 O1 C12 100.1(5) 7_556 . . . ?
N1 Cu1 O1 C12 -79.9(5) . . . . ?
O2 Cu1 O2 C14 40(100) 7_556 . . . ?
O1 Cu1 O2 C14 -8.3(5) . . . . ?
O1 Cu1 O2 C14 171.7(5) 7_556 . . . ?
N1 Cu1 O2 C14 -101.8(5) 7_556 . . . ?
N1 Cu1 O2 C14 78.2(5) . . . . ?
O2 Cu1 N1 C6 -160.3(5) 7_556 . . . ?
O2 Cu1 N1 C6 19.7(5) . . . . ?
O1 Cu1 N1 C6 111.0(5) . . . . ?
O1 Cu1 N1 C6 -69.0(5) 7_556 . . . ?
N1 Cu1 N1 C6 20(100) 7_556 . . . ?
O2 Cu1 N1 C2 35.4(5) 7_556 . . . ?
O2 Cu1 N1 C2 -144.6(5) . . . . ?
O1 Cu1 N1 C2 -53.3(5) . . . . ?
O1 Cu1 N1 C2 126.7(5) 7_556 . . . ?
N1 Cu1 N1 C2 -144(100) 7_556 . . . ?
C6 N1 C2 C3 -1.9(11) . . . . ?
Cu1 N1 C2 C3 163.1(5) . . . . ?
N1 C2 C3 C4 -0.3(10) . . . . ?
N1 C2 C3 Cl1 -176.1(6) . . . . ?
C2 C3 C4 C5 1.6(8) . . . . ?
Cl1 C3 C4 C5 177.2(4) . . . . ?
C2 C3 C4 C1 -178.5(6) . . . . ?
Cl1 C3 C4 C1 -2.9(8) . . . . ?
C4 C1 C4 C5 131.8(6) 2 . . . ?
C10 C1 C4 C5 -48.2(6) . . . . ?
C4 C1 C4 C3 -48.1(4) 2 . . . ?
C10 C1 C4 C3 131.9(4) . . . . ?
C3 C4 C5 C6 -0.7(8) . . . . ?
C1 C4 C5 C6 179.4(5) . . . . ?
C3 C4 C5 Cl2 177.9(4) . . . . ?
C1 C4 C5 Cl2 -2.0(8) . . . . ?
C2 N1 C6 C5 2.8(10) . . . . ?
Cu1 N1 C6 C5 -161.7(5) . . . . ?
C4 C5 C6 N1 -1.6(10) . . . . ?
Cl2 C5 C6 N1 179.7(5) . . . . ?
C8 C7 C8 C9 0.5(4) 2 . . . ?
Cl3 C7 C8 C9 -179.5(4) . . . . ?
C7 C8 C9 C10 -1.0(9) . . . . ?
C7 C8 C9 Cl4 -176.9(4) . . . . ?
C8 C9 C10 C9 0.5(5) . . . 2 ?
Cl4 C9 C10 C9 176.3(6) . . . 2 ?
C8 C9 C10 C1 -179.5(5) . . . . ?
Cl4 C9 C10 C1 -3.7(6) . . . . ?
C4 C1 C10 C9 -51.0(4) . . . . ?
C4 C1 C10 C9 129.0(4) 2 . . . ?
C4 C1 C10 C9 129.0(4) . . . 2 ?
C4 C1 C10 C9 -51.0(4) 2 . . 2 ?
Cu1 O1 C12 C13 -7.2(11) . . . . ?
Cu1 O1 C12 C11 168.9(6) . . . . ?
F2 C11 C12 O1 164.1(10) . . . . ?
F3 C11 C12 O1 -76.8(10) . . . . ?
F1 C11 C12 O1 41.1(12) . . . . ?
F2 C11 C12 C13 -19.4(14) . . . . ?
F3 C11 C12 C13 99.7(10) . . . . ?
F1 C11 C12 C13 -142.4(9) . . . . ?
O1 C12 C13 C14 -0.8(13) . . . . ?
C11 C12 C13 C14 -176.7(8) . . . . ?
Cu1 O2 C14 C13 4.0(10) . . . . ?
Cu1 O2 C14 C15 -173.5(5) . . . . ?
C12 C13 C14 O2 2.7(13) . . . . ?
C12 C13 C14 C15 -179.9(8) . . . . ?
O2 C14 C15 F5 -42.3(10) . . . . ?
C13 C14 C15 F5 140.0(8) . . . . ?
O2 C14 C15 F6 -162.3(7) . . . . ?
C13 C14 C15 F6 20.0(12) . . . . ?
O2 C14 C15 F4 76.7(9) . . . . ?
C13 C14 C15 F4 -101.0(9) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_cubis_140K
_database_code_depnum_ccdc_archive 'CCDC 1884448'
_audit_update_record             
;
2019-01-14 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C27 H8 Cl7 Cu F12 N2 O4'
_chemical_formula_moiety         'C27 H8 Cl7 Cu F12 N2 O4'
_chemical_formula_weight         964.07
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_symmetry_equiv_pos_as_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                   15.3428(18)
_cell_length_b                   11.0604(10)
_cell_length_c                   20.949(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.478(7)
_cell_angle_gamma                90.0000
_cell_volume                     3471.0(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4457
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    140
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888.00
_exptl_absorpt_coefficient_mu    1.270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_T_max  0.963

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      140
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            13594
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_min         3.004
_diffrn_reflns_theta_full        27.460
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       27
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3948
_reflns_number_gt                3172
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1138
_refine_ls_wR_factor_gt          0.1042
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3948
_refine_ls_number_parameters     243
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0488P)²+10.1367P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.43
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.7500 0.2500 0.5000 0.02584(15) Uani 1 2 d S . .
Cl1 Cl 0.62874(6) 0.20088(8) 0.22760(4) 0.0371(2) Uani 1 1 d . . .
Cl2 Cl 0.47054(6) -0.07238(8) 0.38829(4) 0.0396(2) Uani 1 1 d . . .
Cl3 Cl 0.5000 -0.54211(11) 0.2500 0.0691(5) Uani 1 2 d S . .
Cl4 Cl 0.68118(6) -0.12708(8) 0.28207(5) 0.0471(3) Uani 1 1 d . . .
F1 F 0.97850(17) 0.0952(2) 0.39951(13) 0.0636(7) Uani 1 1 d . . .
F2 F 0.9566(2) -0.0874(3) 0.42214(17) 0.0930(11) Uani 1 1 d . . .
F3 F 0.86229(19) 0.0067(3) 0.34709(12) 0.0796(9) Uani 1 1 d . . .
F4 F 0.65890(18) -0.1380(2) 0.54163(13) 0.0647(7) Uani 1 1 d . . .
F5 F 0.74146(19) -0.0754(2) 0.63162(11) 0.0622(7) Uani 1 1 d . . .
F6 F 0.79231(19) -0.2061(2) 0.57272(12) 0.0618(7) Uani 1 1 d . . .
O1 O 0.84850(19) 0.1718(2) 0.45394(12) 0.0438(6) Uani 1 1 d . . .
O2 O 0.74146(16) 0.09767(19) 0.54605(10) 0.0325(5) Uani 1 1 d . . .
N1 N 0.6516(2) 0.1851(2) 0.41757(14) 0.0369(7) Uani 1 1 d . . .
C1 C 0.5000 -0.0002(4) 0.2500 0.0238(9) Uani 1 2 d S . .
C2 C 0.6578(3) 0.2156(3) 0.35718(17) 0.0354(8) Uani 1 1 d . . .
H2 H 0.6976 0.2786 0.3517 0.043 Uiso 1 1 calc R . .
C3 C 0.6087(2) 0.1591(3) 0.30236(16) 0.0285(7) Uani 1 1 d . . .
C4 C 0.5492(2) 0.0649(3) 0.30736(15) 0.0256(6) Uani 1 1 d . . .
C5 C 0.5429(2) 0.0367(3) 0.37174(16) 0.0287(7) Uani 1 1 d . . .
C6 C 0.5932(2) 0.0980(3) 0.42431(17) 0.0340(7) Uani 1 1 d . . .
H6 H 0.5864 0.0778 0.4670 0.041 Uiso 1 1 calc R . .
C7 C 0.5000 -0.3850(4) 0.2500 0.0409(13) Uani 1 2 d S . .
C8 C 0.5802(3) -0.3251(3) 0.26552(17) 0.0383(8) Uani 1 1 d . . .
H8 H 0.6349 -0.3684 0.2758 0.046 Uiso 1 1 calc R . .
C9 C 0.5791(2) -0.2002(3) 0.26573(16) 0.0305(7) Uani 1 1 d . . .
C10 C 0.5000 -0.1326(4) 0.2500 0.0258(9) Uani 1 2 d S . .
C11 C 0.9155(3) 0.0176(4) 0.4060(2) 0.0503(10) Uani 1 1 d . . .
C12 C 0.8615(3) 0.0611(3) 0.45483(17) 0.0375(8) Uani 1 1 d . . .
C13 C 0.8290(3) -0.0276(3) 0.49168(17) 0.0397(8) Uani 1 1 d . . .
H13 H 0.8462 -0.1093 0.4875 0.048 Uiso 1 1 calc R . .
C14 C 0.7737(2) -0.0022(3) 0.53352(15) 0.0324(7) Uani 1 1 d . . .
C15 C 0.7420(3) -0.1068(3) 0.57026(19) 0.0457(9) Uani 1 1 d . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O2 1.960(2) 7_656 ?
Cu1 O2 1.960(2) . ?
Cu1 O1 2.143(3) . ?
Cu1 O1 2.143(3) 7_656 ?
Cu1 N1 2.157(3) . ?
Cu1 N1 2.157(3) 7_656 ?
Cl1 C3 1.723(3) . ?
Cl2 C5 1.724(3) . ?
Cl3 C7 1.738(5) . ?
Cl4 C9 1.730(3) . ?
F1 C11 1.321(5) . ?
F2 C11 1.329(5) . ?
F3 C11 1.331(5) . ?
F4 C15 1.332(5) . ?
F5 C15 1.333(4) . ?
F6 C15 1.337(4) . ?
O1 C12 1.240(4) . ?
O2 C14 1.261(4) . ?
N1 C2 1.333(4) . ?
N1 C6 1.343(4) . ?
C1 C4 1.463(4) 2_655 ?
C1 C4 1.463(4) . ?
C1 C10 1.465(6) . ?
C2 C3 1.379(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(4) . ?
C4 C5 1.408(4) . ?
C5 C6 1.379(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(4) . ?
C7 C8 1.373(4) 2_655 ?
C8 C9 1.381(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.403(4) . ?
C10 C9 1.403(4) 2_655 ?
C11 C12 1.527(5) . ?
C12 C13 1.405(5) . ?
C13 C14 1.375(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.526(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 180.000(1) 7_656 . ?
O2 Cu1 O1 89.81(9) 7_656 . ?
O2 Cu1 O1 90.19(9) . . ?
O2 Cu1 O1 90.19(9) 7_656 7_656 ?
O2 Cu1 O1 89.81(9) . 7_656 ?
O1 Cu1 O1 180.000(1) . 7_656 ?
O2 Cu1 N1 90.11(10) 7_656 . ?
O2 Cu1 N1 89.89(10) . . ?
O1 Cu1 N1 86.85(10) . . ?
O1 Cu1 N1 93.15(11) 7_656 . ?
O2 Cu1 N1 89.89(10) 7_656 7_656 ?
O2 Cu1 N1 90.11(10) . 7_656 ?
O1 Cu1 N1 93.15(11) . 7_656 ?
O1 Cu1 N1 86.85(10) 7_656 7_656 ?
N1 Cu1 N1 180.000(1) . 7_656 ?
C12 O1 Cu1 121.2(2) . . ?
C14 O2 Cu1 125.4(2) . . ?
C2 N1 C6 117.9(3) . . ?
C2 N1 Cu1 119.6(2) . . ?
C6 N1 Cu1 121.5(2) . . ?
C4 C1 C4 121.0(4) 2_655 . ?
C4 C1 C10 119.50(18) 2_655 . ?
C4 C1 C10 119.50(18) . . ?
N1 C2 C3 122.5(3) . . ?
N1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 Cl1 117.6(2) . . ?
C4 C3 Cl1 120.9(2) . . ?
C3 C4 C5 114.6(3) . . ?
C3 C4 C1 122.2(3) . . ?
C5 C4 C1 123.2(3) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 Cl2 117.2(2) . . ?
C4 C5 Cl2 121.9(2) . . ?
N1 C6 C5 122.7(3) . . ?
N1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C8 C7 C8 122.3(4) . 2_655 ?
C8 C7 Cl3 118.9(2) . . ?
C8 C7 Cl3 118.9(2) 2_655 . ?
C7 C8 C9 118.2(3) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C8 C9 C10 122.9(3) . . ?
C8 C9 Cl4 117.2(3) . . ?
C10 C9 Cl4 119.8(2) . . ?
C9 C10 C9 115.6(4) 2_655 . ?
C9 C10 C1 122.2(2) 2_655 . ?
C9 C10 C1 122.2(2) . . ?
F1 C11 F2 106.1(4) . . ?
F1 C11 F3 106.2(3) . . ?
F2 C11 F3 108.6(4) . . ?
F1 C11 C12 112.3(3) . . ?
F2 C11 C12 113.7(3) . . ?
F3 C11 C12 109.7(4) . . ?
O1 C12 C13 128.6(4) . . ?
O1 C12 C11 114.2(3) . . ?
C13 C12 C11 117.1(3) . . ?
C14 C13 C12 123.3(3) . . ?
C14 C13 H13 118.4 . . ?
C12 C13 H13 118.4 . . ?
O2 C14 C13 129.5(3) . . ?
O2 C14 C15 112.2(3) . . ?
C13 C14 C15 118.3(3) . . ?
F5 C15 F6 107.5(3) . . ?
F5 C15 F4 107.2(3) . . ?
F6 C15 F4 107.1(3) . . ?
F5 C15 C14 111.0(3) . . ?
F6 C15 C14 113.5(3) . . ?
F4 C15 C14 110.3(3) . . ?

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
O2 Cu1 O1 C12 -166.2(3) 7_656 . . . ?
O2 Cu1 O1 C12 13.8(3) . . . . ?
O1 Cu1 O1 C12 85(100) 7_656 . . . ?
N1 Cu1 O1 C12 -76.0(3) . . . . ?
N1 Cu1 O1 C12 104.0(3) 7_656 . . . ?
O2 Cu1 O2 C14 -134(100) 7_656 . . . ?
O1 Cu1 O2 C14 -12.5(3) . . . . ?
O1 Cu1 O2 C14 167.5(3) 7_656 . . . ?
N1 Cu1 O2 C14 74.4(3) . . . . ?
N1 Cu1 O2 C14 -105.6(3) 7_656 . . . ?
O2 Cu1 N1 C2 35.0(3) 7_656 . . . ?
O2 Cu1 N1 C2 -145.0(3) . . . . ?
O1 Cu1 N1 C2 -54.8(3) . . . . ?
O1 Cu1 N1 C2 125.2(3) 7_656 . . . ?
N1 Cu1 N1 C2 176(100) 7_656 . . . ?
O2 Cu1 N1 C6 -156.9(3) 7_656 . . . ?
O2 Cu1 N1 C6 23.1(3) . . . . ?
O1 Cu1 N1 C6 113.3(3) . . . . ?
O1 Cu1 N1 C6 -66.7(3) 7_656 . . . ?
N1 Cu1 N1 C6 -16(100) 7_656 . . . ?
C6 N1 C2 C3 -1.7(5) . . . . ?
Cu1 N1 C2 C3 166.8(3) . . . . ?
N1 C2 C3 C4 -0.4(5) . . . . ?
N1 C2 C3 Cl1 -175.8(3) . . . . ?
C2 C3 C4 C5 1.6(5) . . . . ?
Cl1 C3 C4 C5 176.9(2) . . . . ?
C2 C3 C4 C1 -176.7(3) . . . . ?
Cl1 C3 C4 C1 -1.4(4) . . . . ?
C4 C1 C4 C3 -49.4(2) 2_655 . . . ?
C10 C1 C4 C3 130.6(2) . . . . ?
C4 C1 C4 C5 132.5(3) 2_655 . . . ?
C10 C1 C4 C5 -47.5(3) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C1 C4 C5 C6 177.5(3) . . . . ?
C3 C4 C5 Cl2 177.6(2) . . . . ?
C1 C4 C5 Cl2 -4.1(4) . . . . ?
C2 N1 C6 C5 2.6(5) . . . . ?
Cu1 N1 C6 C5 -165.8(3) . . . . ?
C4 C5 C6 N1 -1.3(5) . . . . ?
Cl2 C5 C6 N1 -179.8(3) . . . . ?
C8 C7 C8 C9 0.4(2) 2_655 . . . ?
Cl3 C7 C8 C9 -179.6(2) . . . . ?
C7 C8 C9 C10 -0.9(5) . . . . ?
C7 C8 C9 Cl4 -177.3(2) . . . . ?
C8 C9 C10 C9 0.4(2) . . . 2_655 ?
Cl4 C9 C10 C9 176.8(3) . . . 2_655 ?
C8 C9 C10 C1 -179.6(2) . . . . ?
Cl4 C9 C10 C1 -3.2(3) . . . . ?
C4 C1 C10 C9 -51.4(2) 2_655 . . 2_655 ?
C4 C1 C10 C9 128.6(2) . . . 2_655 ?
C4 C1 C10 C9 128.6(2) 2_655 . . . ?
C4 C1 C10 C9 -51.4(2) . . . . ?
Cu1 O1 C12 C13 -10.9(5) . . . . ?
Cu1 O1 C12 C11 165.2(2) . . . . ?
F1 C11 C12 O1 36.3(5) . . . . ?
F2 C11 C12 O1 156.8(4) . . . . ?
F3 C11 C12 O1 -81.5(4) . . . . ?
F1 C11 C12 C13 -147.1(4) . . . . ?
F2 C11 C12 C13 -26.7(5) . . . . ?
F3 C11 C12 C13 95.1(4) . . . . ?
O1 C12 C13 C14 1.3(6) . . . . ?
C11 C12 C13 C14 -174.7(3) . . . . ?
Cu1 O2 C14 C13 7.9(5) . . . . ?
Cu1 O2 C14 C15 -170.3(2) . . . . ?
C12 C13 C14 O2 1.2(6) . . . . ?
C12 C13 C14 C15 179.3(3) . . . . ?
O2 C14 C15 F5 -41.4(4) . . . . ?
C13 C14 C15 F5 140.2(3) . . . . ?
O2 C14 C15 F6 -162.6(3) . . . . ?
C13 C14 C15 F6 19.0(5) . . . . ?
O2 C14 C15 F4 77.3(4) . . . . ?
C13 C14 C15 F4 -101.1(4) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_cubis_120K
_database_code_depnum_ccdc_archive 'CCDC 1884446'
_audit_update_record             
;
2019-01-14 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C27 H8 Cl7 Cu F12 N2 O4'
_chemical_formula_moiety         'C27 H8 Cl7 Cu F12 N2 O4'
_chemical_formula_weight         964.07
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_symmetry_equiv_pos_as_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                   15.3379(18)
_cell_length_b                   11.0460(10)
_cell_length_c                   20.900(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.657(6)
_cell_angle_gamma                90.0000
_cell_volume                     3454.9(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4546
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    120
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.853
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888.00
_exptl_absorpt_coefficient_mu    1.276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_T_max  0.962

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      120
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            13574
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         3.231
_diffrn_reflns_theta_full        27.480
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3949
_reflns_number_gt                3177
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1123
_refine_ls_wR_factor_gt          0.1016
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3949
_refine_ls_number_parameters     243
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0520P)²+9.8753P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.2500 0.2500 0.5000 0.02296(14) Uani 1 2 d S . .
Cl1 Cl 0.37128(6) 0.20066(7) 0.77267(4) 0.0332(2) Uani 1 1 d . . .
Cl2 Cl 0.52919(6) -0.07216(7) 0.61125(4) 0.0348(2) Uani 1 1 d . . .
Cl3 Cl 0.5000 -0.54310(11) 0.7500 0.0603(5) Uani 1 2 d S . .
Cl4 Cl 0.68116(5) -0.12732(8) 0.78192(5) 0.0416(2) Uani 1 1 d . . .
F1 F 0.02059(16) 0.0944(2) 0.60108(11) 0.0548(6) Uani 1 1 d . . .
F2 F 0.0425(2) -0.0888(2) 0.57756(16) 0.0805(9) Uani 1 1 d . . .
F3 F 0.13735(17) 0.0041(3) 0.65312(11) 0.0676(8) Uani 1 1 d . . .
F4 F 0.34099(16) -0.1382(2) 0.45869(12) 0.0562(6) Uani 1 1 d . . .
F5 F 0.25846(17) -0.0762(2) 0.36848(11) 0.0534(6) Uani 1 1 d . . .
F6 F 0.20754(17) -0.20697(19) 0.42737(11) 0.0545(6) Uani 1 1 d . . .
O1 O 0.15004(18) 0.1712(2) 0.54614(11) 0.0394(6) Uani 1 1 d . . .
O2 O 0.25787(15) 0.09783(18) 0.45389(10) 0.0290(5) Uani 1 1 d . . .
N1 N 0.3477(2) 0.1848(2) 0.58199(13) 0.0332(6) Uani 1 1 d . . .
C1 C 0.5000 -0.0008(4) 0.7500 0.0229(8) Uani 1 2 d S . .
C2 C 0.3413(2) 0.2159(3) 0.64274(16) 0.0312(7) Uani 1 1 d . . .
H2 H 0.3016 0.2790 0.6483 0.037 Uiso 1 1 calc R . .
C3 C 0.3910(2) 0.1587(3) 0.69740(15) 0.0256(6) Uani 1 1 d . . .
C4 C 0.45067(19) 0.0648(2) 0.69264(15) 0.0228(6) Uani 1 1 d . . .
C5 C 0.4563(2) 0.0364(3) 0.62795(16) 0.0265(6) Uani 1 1 d . . .
C6 C 0.4056(2) 0.0979(3) 0.57495(16) 0.0304(7) Uani 1 1 d . . .
H6 H 0.4121 0.0777 0.5321 0.036 Uiso 1 1 calc R . .
C7 C 0.5000 -0.3861(4) 0.7500 0.0372(12) Uani 1 2 d S . .
C8 C 0.5803(2) -0.3260(3) 0.76527(16) 0.0343(8) Uani 1 1 d . . .
H8 H 0.6351 -0.3695 0.7752 0.041 Uiso 1 1 calc R . .
C9 C 0.5795(2) -0.2003(3) 0.76588(15) 0.0271(7) Uani 1 1 d . . .
C10 C 0.5000 -0.1330(4) 0.7500 0.0237(9) Uani 1 2 d S . .
C11 C 0.0832(3) 0.0164(3) 0.59421(19) 0.0435(9) Uani 1 1 d . . .
C12 C 0.1373(2) 0.0606(3) 0.54535(16) 0.0332(7) Uani 1 1 d . . .
C13 C 0.1701(2) -0.0282(3) 0.50829(16) 0.0340(7) Uani 1 1 d . . .
H13 H 0.1531 -0.1101 0.5124 0.041 Uiso 1 1 calc R . .
C14 C 0.2256(2) -0.0024(3) 0.46632(15) 0.0293(7) Uani 1 1 d . . .
C15 C 0.2574(3) -0.1073(3) 0.42975(17) 0.0394(8) Uani 1 1 d . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O2 1.954(2) . ?
Cu1 O2 1.954(2) 7_556 ?
Cu1 N1 2.139(3) 7_556 ?
Cu1 N1 2.139(3) . ?
Cu1 O1 2.165(3) . ?
Cu1 O1 2.165(3) 7_556 ?
Cl1 C3 1.729(3) . ?
Cl2 C5 1.726(3) . ?
Cl3 C7 1.734(4) . ?
Cl4 C9 1.721(3) . ?
F1 C11 1.322(4) . ?
F2 C11 1.329(5) . ?
F3 C11 1.332(4) . ?
F4 C15 1.337(4) . ?
F5 C15 1.329(4) . ?
F6 C15 1.335(4) . ?
O1 C12 1.237(4) . ?
O2 C14 1.263(4) . ?
N1 C6 1.336(4) . ?
N1 C2 1.340(4) . ?
C1 C10 1.460(5) . ?
C1 C4 1.462(4) . ?
C1 C4 1.462(4) 2_656 ?
C2 C3 1.380(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.401(4) . ?
C4 C5 1.409(4) . ?
C5 C6 1.385(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(4) 2_656 ?
C7 C8 1.373(4) . ?
C8 C9 1.389(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.404(4) . ?
C10 C9 1.404(4) 2_656 ?
C11 C12 1.530(5) . ?
C12 C13 1.409(5) . ?
C13 C14 1.379(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.526(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 180.0 . 7_556 ?
O2 Cu1 N1 90.16(9) . 7_556 ?
O2 Cu1 N1 89.84(9) 7_556 7_556 ?
O2 Cu1 N1 89.84(9) . . ?
O2 Cu1 N1 90.16(9) 7_556 . ?
N1 Cu1 N1 180.00(11) 7_556 . ?
O2 Cu1 O1 90.01(9) . . ?
O2 Cu1 O1 89.99(9) 7_556 . ?
N1 Cu1 O1 92.97(10) 7_556 . ?
N1 Cu1 O1 87.03(10) . . ?
O2 Cu1 O1 89.99(9) . 7_556 ?
O2 Cu1 O1 90.01(9) 7_556 7_556 ?
N1 Cu1 O1 87.03(10) 7_556 7_556 ?
N1 Cu1 O1 92.97(10) . 7_556 ?
O1 Cu1 O1 180.0 . 7_556 ?
C12 O1 Cu1 121.1(2) . . ?
C14 O2 Cu1 125.7(2) . . ?
C6 N1 C2 118.5(3) . . ?
C6 N1 Cu1 121.3(2) . . ?
C2 N1 Cu1 119.3(2) . . ?
C10 C1 C4 119.71(17) . . ?
C10 C1 C4 119.71(17) . 2_656 ?
C4 C1 C4 120.6(3) . 2_656 ?
N1 C2 C3 121.7(3) . . ?
N1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C4 122.1(3) . . ?
C2 C3 Cl1 117.1(2) . . ?
C4 C3 Cl1 120.7(2) . . ?
C3 C4 C5 114.3(3) . . ?
C3 C4 C1 122.5(3) . . ?
C5 C4 C1 123.2(2) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 Cl2 117.0(2) . . ?
C4 C5 Cl2 121.8(2) . . ?
N1 C6 C5 122.3(3) . . ?
N1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C8 C7 C8 122.3(4) 2_656 . ?
C8 C7 Cl3 118.9(2) 2_656 . ?
C8 C7 Cl3 118.9(2) . . ?
C7 C8 C9 118.4(3) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C8 C9 C10 122.4(3) . . ?
C8 C9 Cl4 117.4(2) . . ?
C10 C9 Cl4 120.1(2) . . ?
C9 C10 C9 116.1(4) 2_656 . ?
C9 C10 C1 121.93(19) 2_656 . ?
C9 C10 C1 121.93(19) . . ?
F1 C11 F3 106.7(3) . . ?
F1 C11 F2 106.7(3) . . ?
F3 C11 F2 108.3(3) . . ?
F1 C11 C12 112.2(3) . . ?
F3 C11 C12 109.3(3) . . ?
F2 C11 C12 113.4(3) . . ?
O1 C12 C13 128.4(3) . . ?
O1 C12 C11 114.4(3) . . ?
C13 C12 C11 117.1(3) . . ?
C14 C13 C12 123.3(3) . . ?
C14 C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?
O2 C14 C13 129.5(3) . . ?
O2 C14 C15 112.3(3) . . ?
C13 C14 C15 118.1(3) . . ?
F5 C15 F6 107.8(3) . . ?
F5 C15 F4 106.8(3) . . ?
F6 C15 F4 106.9(3) . . ?
F5 C15 C14 111.1(3) . . ?
F6 C15 C14 113.7(3) . . ?
F4 C15 C14 110.4(3) . . ?

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
O2 Cu1 O1 C12 14.4(2) . . . . ?
O2 Cu1 O1 C12 -165.6(2) 7_556 . . . ?
N1 Cu1 O1 C12 104.5(3) 7_556 . . . ?
N1 Cu1 O1 C12 -75.5(3) . . . . ?
O1 Cu1 O1 C12 -131(100) 7_556 . . . ?
O2 Cu1 O2 C14 153(53) 7_556 . . . ?
N1 Cu1 O2 C14 -105.8(2) 7_556 . . . ?
N1 Cu1 O2 C14 74.2(2) . . . . ?
O1 Cu1 O2 C14 -12.8(2) . . . . ?
O1 Cu1 O2 C14 167.2(2) 7_556 . . . ?
O2 Cu1 N1 C6 23.4(3) . . . . ?
O2 Cu1 N1 C6 -156.6(3) 7_556 . . . ?
N1 Cu1 N1 C6 -111(14) 7_556 . . . ?
O1 Cu1 N1 C6 113.4(3) . . . . ?
O1 Cu1 N1 C6 -66.6(3) 7_556 . . . ?
O2 Cu1 N1 C2 -145.0(3) . . . . ?
O2 Cu1 N1 C2 35.0(3) 7_556 . . . ?
N1 Cu1 N1 C2 81(14) 7_556 . . . ?
O1 Cu1 N1 C2 -55.0(2) . . . . ?
O1 Cu1 N1 C2 125.0(2) 7_556 . . . ?
C6 N1 C2 C3 -1.6(5) . . . . ?
Cu1 N1 C2 C3 167.1(2) . . . . ?
N1 C2 C3 C4 -0.2(5) . . . . ?
N1 C2 C3 Cl1 -175.9(3) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
Cl1 C3 C4 C5 176.7(2) . . . . ?
C2 C3 C4 C1 -176.6(3) . . . . ?
Cl1 C3 C4 C1 -1.0(4) . . . . ?
C10 C1 C4 C3 130.4(2) . . . . ?
C4 C1 C4 C3 -49.6(2) 2_656 . . . ?
C10 C1 C4 C5 -47.2(3) . . . . ?
C4 C1 C4 C5 132.8(3) 2_656 . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C1 C4 C5 C6 177.4(3) . . . . ?
C3 C4 C5 Cl2 177.2(2) . . . . ?
C1 C4 C5 Cl2 -5.0(4) . . . . ?
C2 N1 C6 C5 2.5(5) . . . . ?
Cu1 N1 C6 C5 -166.0(2) . . . . ?
C4 C5 C6 N1 -1.5(5) . . . . ?
Cl2 C5 C6 N1 -179.2(3) . . . . ?
C8 C7 C8 C9 0.7(2) 2_656 . . . ?
Cl3 C7 C8 C9 -179.3(2) . . . . ?
C7 C8 C9 C10 -1.5(4) . . . . ?
C7 C8 C9 Cl4 -177.4(2) . . . . ?
C8 C9 C10 C9 0.8(2) . . . 2_656 ?
Cl4 C9 C10 C9 176.6(3) . . . 2_656 ?
C8 C9 C10 C1 -179.2(2) . . . . ?
Cl4 C9 C10 C1 -3.4(3) . . . . ?
C4 C1 C10 C9 -51.34(19) . . . 2_656 ?
C4 C1 C10 C9 128.66(19) 2_656 . . 2_656 ?
C4 C1 C10 C9 128.66(19) . . . . ?
C4 C1 C10 C9 -51.34(19) 2_656 . . . ?
Cu1 O1 C12 C13 -11.3(5) . . . . ?
Cu1 O1 C12 C11 164.9(2) . . . . ?
F1 C11 C12 O1 35.6(5) . . . . ?
F3 C11 C12 O1 -82.5(4) . . . . ?
F2 C11 C12 O1 156.6(3) . . . . ?
F1 C11 C12 C13 -147.7(3) . . . . ?
F3 C11 C12 C13 94.2(4) . . . . ?
F2 C11 C12 C13 -26.7(5) . . . . ?
O1 C12 C13 C14 1.4(6) . . . . ?
C11 C12 C13 C14 -174.8(3) . . . . ?
Cu1 O2 C14 C13 8.0(5) . . . . ?
Cu1 O2 C14 C15 -169.8(2) . . . . ?
C12 C13 C14 O2 1.5(6) . . . . ?
C12 C13 C14 C15 179.2(3) . . . . ?
O2 C14 C15 F5 -41.2(4) . . . . ?
C13 C14 C15 F5 140.7(3) . . . . ?
O2 C14 C15 F6 -163.0(3) . . . . ?
C13 C14 C15 F6 18.9(5) . . . . ?
O2 C14 C15 F4 77.0(4) . . . . ?
C13 C14 C15 F4 -101.1(4) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
