# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1529094'
_audit_update_record             
;
2017-01-22 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 Cl Cu F6 N2 O3'
_chemical_formula_weight         586.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.7047(13)
_cell_length_b                   10.1712(6)
_cell_length_c                   23.1159(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4868.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2045
_cell_measurement_theta_min      4.3830
_cell_measurement_theta_max      62.5590

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2376
_exptl_absorpt_coefficient_mu    2.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55366
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11232
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.82
_diffrn_reflns_theta_max         72.29
_reflns_number_total             4704
_reflns_number_gt                2415
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1517P)²+0.5270P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4704
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.2866
_refine_ls_wR_factor_gt          0.2153
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.057
_refine_ls_shift/su_mean         0.003

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 0.54781(4) 0.12219(8) 0.32011(4) 0.0716(4) Uani 1 1 d . . .
Cl1 Cl 0.62328(8) 0.2724(2) 0.29292(10) 0.1150(7) Uani 1 1 d . . .
O1 O 0.48565(19) 0.2578(4) 0.32245(17) 0.0776(11) Uani 1 1 d . . .
F1 F 0.4716(2) 0.4902(4) 0.3988(2) 0.1256(15) Uani 1 1 d . . .
F3 F 0.3896(3) 0.5968(4) 0.3707(3) 0.1459(19) Uani 1 1 d . . .
F6 F 0.7344(3) -0.0240(8) 0.5209(3) 0.207(3) Uani 1 1 d . . .
N1 N 0.4813(2) -0.0195(4) 0.3396(2) 0.0693(11) Uani 1 1 d . . .
F5 F 0.7167(2) 0.0824(7) 0.4423(3) 0.172(2) Uani 1 1 d . . .
F2 F 0.4595(2) 0.5295(4) 0.3094(2) 0.1144(14) Uani 1 1 d . . .
C12 C 0.3905(3) 0.3680(6) 0.3512(3) 0.0785(16) Uani 1 1 d . . .
F4 F 0.6728(3) 0.1464(8) 0.5206(3) 0.179(3) Uani 1 1 d . . .
C13 C 0.4241(3) 0.2529(5) 0.3350(2) 0.0680(13) Uani 1 1 d . . .
C16 C 0.5271(3) -0.0816(6) 0.4375(3) 0.0782(15) Uani 1 1 d . . .
N2 N 0.6064(2) -0.0337(6) 0.3113(2) 0.0868(15) Uani 1 1 d . . .
C8 C 0.3875(3) 0.1362(6) 0.3316(3) 0.0742(15) Uani 1 1 d . . .
C1 C 0.5051(3) -0.1467(6) 0.3159(3) 0.0778(17) Uani 1 1 d . . .
H1A H 0.4899 -0.1573 0.2765 0.093 Uiso 1 1 calc R . .
H1B H 0.4883 -0.2188 0.3388 0.093 Uiso 1 1 calc R . .
C2 C 0.5773(4) -0.1499(7) 0.3168(3) 0.0843(18) Uani 1 1 d . . .
C7 C 0.4194(3) 0.0131(6) 0.3103(3) 0.0760(15) Uani 1 1 d . . .
H7A H 0.3897 -0.0598 0.3154 0.091 Uiso 1 1 calc R . .
H7B H 0.4275 0.0221 0.2691 0.091 Uiso 1 1 calc R . .
C21 C 0.5790(3) -0.0016(6) 0.4468(3) 0.0800(16) Uani 1 1 d . . .
C17 C 0.5268(4) -0.2077(7) 0.4608(3) 0.098(2) Uani 1 1 d . . .
H17 H 0.4912 -0.2619 0.4548 0.117 Uiso 1 1 calc R . .
C14 C 0.4268(4) 0.4957(6) 0.3576(4) 0.096(2) Uani 1 1 d . . .
C10 C 0.2904(3) 0.2542(8) 0.3585(3) 0.104(2) Uani 1 1 d . . .
H10 H 0.2461 0.2542 0.3655 0.124 Uiso 1 1 calc R . .
C6 C 0.6713(4) -0.0294(10) 0.3070(4) 0.115(3) Uani 1 1 d . . .
H6 H 0.6924 0.0506 0.3027 0.138 Uiso 1 1 calc R . .
C15 C 0.4697(3) -0.0318(6) 0.4035(2) 0.0776(16) Uani 1 1 d . . .
H15A H 0.4336 -0.0911 0.4096 0.093 Uiso 1 1 calc R . .
H15B H 0.4574 0.0536 0.4185 0.093 Uiso 1 1 calc R . .
C9 C 0.3221(3) 0.1379(7) 0.3433(3) 0.0856(18) Uani 1 1 d . . .
H9 H 0.2987 0.0601 0.3411 0.103 Uiso 1 1 calc R . .
C11 C 0.3249(4) 0.3667(7) 0.3627(3) 0.095(2) Uani 1 1 d . . .
H11 H 0.3043 0.4442 0.3736 0.114 Uiso 1 1 calc R . .
C18 C 0.5780(6) -0.2531(9) 0.4922(3) 0.125(3) Uani 1 1 d . . .
H18 H 0.5770 -0.3374 0.5077 0.150 Uiso 1 1 calc R . .
C20 C 0.6316(4) -0.0489(10) 0.4788(3) 0.105(2) Uani 1 1 d . . .
C22 C 0.6881(5) 0.0376(15) 0.4903(4) 0.156(5) Uani 1 1 d . . .
C19 C 0.6307(5) -0.1740(11) 0.5008(3) 0.126(3) Uani 1 1 d . . .
H19 H 0.6659 -0.2052 0.5216 0.151 Uiso 1 1 calc R . .
C3 C 0.6111(5) -0.2668(9) 0.3193(3) 0.119(3) Uani 1 1 d . . .
H3 H 0.5893 -0.3463 0.3237 0.143 Uiso 1 1 calc R . .
C5 C 0.7065(5) -0.1467(15) 0.3091(5) 0.161(5) Uani 1 1 d . . .
H5 H 0.7513 -0.1443 0.3061 0.193 Uiso 1 1 calc R . .
C4 C 0.6760(6) -0.2639(13) 0.3155(5) 0.155(5) Uani 1 1 d . . .
H4 H 0.6996 -0.3415 0.3172 0.186 Uiso 1 1 calc R . .
O2 O 0.5754(2) 0.1201(4) 0.4229(2) 0.0932(13) Uani 1 1 d . . .
H2 H 0.5829 0.1966 0.4440 0.112 Uiso 1 1 calc R . .
O3 O 0.6451(6) 0.3303(10) 0.4213(4) 0.227(5) Uani 1 1 d . . .
H3A H 0.6740 0.3006 0.4417 0.341 Uiso 1 1 calc R . .
C23 C 0.6218(9) 0.4267(13) 0.4444(7) 0.243(9) Uani 1 1 d . . .
H23A H 0.6380 0.4339 0.4831 0.365 Uiso 1 1 calc R . .
H23B H 0.5757 0.4184 0.4453 0.365 Uiso 1 1 calc R . .
H23C H 0.6334 0.5039 0.4229 0.365 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.887(4) . ?
Cu1 N2 2.006(6) . ?
Cu1 N1 2.044(5) . ?
Cu1 Cl1 2.2740(18) . ?
Cu1 O2 2.445(5) . ?
O1 C13 1.309(7) . ?
F1 C14 1.330(8) . ?
F3 C14 1.319(7) . ?
F6 C22 1.346(11) . ?
N1 C7 1.488(7) . ?
N1 C1 1.489(7) . ?
N1 C15 1.500(7) . ?
F5 C22 1.338(10) . ?
F2 C14 1.348(8) . ?
C12 C11 1.384(9) . ?
C12 C13 1.413(8) . ?
C12 C14 1.509(9) . ?
F4 C22 1.348(14) . ?
C13 C8 1.409(8) . ?
C16 C21 1.366(8) . ?
C16 C17 1.391(9) . ?
C16 C15 1.512(8) . ?
N2 C2 1.333(9) . ?
N2 C6 1.348(8) . ?
C8 C9 1.382(8) . ?
C8 C7 1.499(8) . ?
C1 C2 1.495(10) . ?
C2 C3 1.380(10) . ?
C21 O2 1.358(7) . ?
C21 C20 1.400(9) . ?
C17 C18 1.365(11) . ?
C10 C11 1.353(9) . ?
C10 C9 1.397(9) . ?
C6 C5 1.399(13) . ?
C18 C19 1.371(12) . ?
C20 C19 1.370(12) . ?
C20 C22 1.488(13) . ?
C3 C4 1.347(14) . ?
C5 C4 1.358(15) . ?
O3 C23 1.216(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N2 173.0(2) . . ?
O1 Cu1 N1 92.86(17) . . ?
N2 Cu1 N1 82.7(2) . . ?
O1 Cu1 Cl1 89.16(13) . . ?
N2 Cu1 Cl1 95.01(18) . . ?
N1 Cu1 Cl1 176.21(15) . . ?
O1 Cu1 O2 97.93(17) . . ?
N2 Cu1 O2 87.16(17) . . ?
N1 Cu1 O2 86.38(17) . . ?
Cl1 Cu1 O2 96.52(12) . . ?
C13 O1 Cu1 130.0(3) . . ?
C7 N1 C1 108.1(4) . . ?
C7 N1 C15 109.2(4) . . ?
C1 N1 C15 110.1(4) . . ?
C7 N1 Cu1 108.8(3) . . ?
C1 N1 Cu1 107.9(4) . . ?
C15 N1 Cu1 112.6(3) . . ?
C11 C12 C13 121.8(6) . . ?
C11 C12 C14 118.6(6) . . ?
C13 C12 C14 119.6(6) . . ?
O1 C13 C8 122.9(5) . . ?
O1 C13 C12 120.4(5) . . ?
C8 C13 C12 116.6(5) . . ?
C21 C16 C17 119.4(6) . . ?
C21 C16 C15 120.1(6) . . ?
C17 C16 C15 120.4(6) . . ?
C2 N2 C6 119.0(7) . . ?
C2 N2 Cu1 114.7(4) . . ?
C6 N2 Cu1 125.8(6) . . ?
C9 C8 C13 120.3(6) . . ?
C9 C8 C7 120.4(6) . . ?
C13 C8 C7 119.0(5) . . ?
N1 C1 C2 110.2(5) . . ?
N2 C2 C3 122.7(8) . . ?
N2 C2 C1 115.5(5) . . ?
C3 C2 C1 121.7(7) . . ?
N1 C7 C8 114.5(5) . . ?
O2 C21 C16 115.8(6) . . ?
O2 C21 C20 124.8(7) . . ?
C16 C21 C20 119.4(7) . . ?
C18 C17 C16 121.0(8) . . ?
F3 C14 F1 106.0(6) . . ?
F3 C14 F2 106.5(6) . . ?
F1 C14 F2 104.6(7) . . ?
F3 C14 C12 113.7(6) . . ?
F1 C14 C12 112.4(6) . . ?
F2 C14 C12 112.9(6) . . ?
C11 C10 C9 119.0(6) . . ?
N2 C6 C5 119.4(9) . . ?
N1 C15 C16 114.4(5) . . ?
C8 C9 C10 121.4(6) . . ?
C10 C11 C12 120.8(6) . . ?
C17 C18 C19 119.8(8) . . ?
C19 C20 C21 120.3(8) . . ?
C19 C20 C22 119.5(9) . . ?
C21 C20 C22 120.2(9) . . ?
F5 C22 F6 106.2(8) . . ?
F5 C22 F4 104.8(11) . . ?
F6 C22 F4 106.1(9) . . ?
F5 C22 C20 113.6(9) . . ?
F6 C22 C20 112.3(11) . . ?
F4 C22 C20 113.2(9) . . ?
C18 C19 C20 120.1(8) . . ?
C4 C3 C2 118.9(10) . . ?
C4 C5 C6 120.6(10) . . ?
C3 C4 C5 119.4(10) . . ?
C21 O2 Cu1 114.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        72.29
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.690
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.075
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1529087'
_audit_update_record             
;
2017-01-22 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H43 Cl2 Cu N2 O6'
_chemical_formula_weight         698.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8818(6)
_cell_length_b                   13.1134(12)
_cell_length_c                   15.0612(11)
_cell_angle_alpha                86.369(7)
_cell_angle_beta                 84.135(6)
_cell_angle_gamma                87.885(6)
_cell_volume                     1740.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2549
_cell_measurement_theta_min      3.1230
_cell_measurement_theta_max      24.4380

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             732
_exptl_absorpt_coefficient_mu    0.825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.743
_exptl_absorpt_correction_T_max  0.855
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11580
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6127
_reflns_number_gt                4711
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0468P)²+0.4134P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6127
_refine_ls_number_parameters     405
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.047
_refine_ls_shift/su_mean         0.001

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 0.86063(4) 0.23698(3) 0.84633(2) 0.03444(14) Uani 1 1 d . . .
O1 O 0.7896(2) 0.37752(16) 0.84343(13) 0.0357(5) Uani 1 1 d . . .
O2 O 0.7495(2) 0.15846(16) 0.70998(14) 0.0403(5) Uani 1 1 d . . .
H2 H 0.6979 0.1310 0.7524 0.060 Uiso 1 1 calc R . .
O3 O 0.6927(2) 0.20368(17) 0.93502(14) 0.0435(6) Uani 1 1 d . . .
O4 O 0.5448(3) 0.1357(2) 0.84537(16) 0.0571(7) Uani 1 1 d . . .
O5 O 1.0164(3) 0.2919(2) 0.97423(16) 0.0563(7) Uani 1 1 d . . .
O6 O 0.8485(3) 0.4170(2) 1.00152(16) 0.0614(8) Uani 1 1 d . . .
N1 N 1.0443(3) 0.26405(19) 0.75734(16) 0.0327(6) Uani 1 1 d . . .
N2 N 0.9657(3) 0.1014(2) 0.86212(16) 0.0339(6) Uani 1 1 d . . .
C1 C 1.1702(3) 0.2028(2) 0.7943(2) 0.0379(8) Uani 1 1 d . . .
H1A H 1.2109 0.2397 0.8398 0.046 Uiso 1 1 calc R . .
H1B H 1.2508 0.1915 0.7471 0.046 Uiso 1 1 calc R . .
C2 C 1.1132(4) 0.1021(2) 0.8340(2) 0.0363(8) Uani 1 1 d . . .
C3 C 1.2061(4) 0.0166(3) 0.8449(2) 0.0495(9) Uani 1 1 d . . .
H3 H 1.3094 0.0191 0.8273 0.059 Uiso 1 1 calc R . .
C4 C 1.1427(5) -0.0729(3) 0.8825(2) 0.0559(10) Uani 1 1 d . . .
H4 H 1.2031 -0.1316 0.8905 0.067 Uiso 1 1 calc R . .
C5 C 0.9901(4) -0.0743(3) 0.9078(2) 0.0496(9) Uani 1 1 d . . .
H5 H 0.9449 -0.1342 0.9316 0.060 Uiso 1 1 calc R . .
C6 C 0.9057(4) 0.0140(3) 0.8975(2) 0.0401(8) Uani 1 1 d . . .
H6 H 0.8025 0.0135 0.9159 0.048 Uiso 1 1 calc R . .
C7 C 1.0786(3) 0.3745(2) 0.7541(2) 0.0404(8) Uani 1 1 d . . .
H7A H 1.1708 0.3864 0.7150 0.048 Uiso 1 1 calc R . .
H7B H 1.0960 0.3929 0.8135 0.048 Uiso 1 1 calc R . .
C8 C 0.9528(4) 0.4415(2) 0.7211(2) 0.0399(8) Uani 1 1 d . . .
C9 C 0.9792(4) 0.5054(3) 0.6450(2) 0.0535(10) Uani 1 1 d . . .
H9 H 1.0743 0.5050 0.6128 0.064 Uiso 1 1 calc R . .
C10 C 0.8662(5) 0.5691(3) 0.6167(3) 0.0638(11) Uani 1 1 d . . .
H10 H 0.8833 0.6111 0.5649 0.077 Uiso 1 1 calc R . .
C11 C 0.7268(5) 0.5703(3) 0.6659(3) 0.0558(10) Uani 1 1 d . . .
H11 H 0.6513 0.6147 0.6464 0.067 Uiso 1 1 calc R . .
C12 C 0.6931(4) 0.5085(2) 0.7436(2) 0.0403(8) Uani 1 1 d . . .
C13 C 0.8110(3) 0.4417(2) 0.7701(2) 0.0352(7) Uani 1 1 d . . .
C14 C 0.5397(4) 0.5182(3) 0.7987(2) 0.0489(9) Uani 1 1 d . . .
C15 C 0.4229(5) 0.5826(4) 0.7496(3) 0.0867(16) Uani 1 1 d . . .
H15A H 0.4590 0.6505 0.7361 0.130 Uiso 1 1 calc R . .
H15B H 0.3287 0.5857 0.7869 0.130 Uiso 1 1 calc R . .
H15C H 0.4078 0.5521 0.6950 0.130 Uiso 1 1 calc R . .
C16 C 0.5616(5) 0.5707(4) 0.8833(3) 0.0742(13) Uani 1 1 d . . .
H16A H 0.6289 0.5296 0.9178 0.111 Uiso 1 1 calc R . .
H16B H 0.4656 0.5793 0.9179 0.111 Uiso 1 1 calc R . .
H16C H 0.6042 0.6364 0.8676 0.111 Uiso 1 1 calc R . .
C17 C 0.4690(4) 0.4142(3) 0.8238(3) 0.0712(12) Uani 1 1 d . . .
H17A H 0.4579 0.3800 0.7705 0.107 Uiso 1 1 calc R . .
H17B H 0.3713 0.4241 0.8564 0.107 Uiso 1 1 calc R . .
H17C H 0.5333 0.3734 0.8605 0.107 Uiso 1 1 calc R . .
C18 C 1.0268(4) 0.2361(3) 0.6638(2) 0.0392(8) Uani 1 1 d . . .
H18A H 0.9436 0.2772 0.6421 0.047 Uiso 1 1 calc R . .
H18B H 1.1180 0.2546 0.6262 0.047 Uiso 1 1 calc R . .
C19 C 0.9982(4) 0.1260(3) 0.65231(19) 0.0372(8) Uani 1 1 d . . .
C20 C 1.1136(4) 0.0628(3) 0.6173(2) 0.0505(10) Uani 1 1 d . . .
H20 H 1.2099 0.0881 0.6024 0.061 Uiso 1 1 calc R . .
C21 C 1.0870(5) -0.0367(3) 0.6044(3) 0.0640(12) Uani 1 1 d . . .
H21 H 1.1662 -0.0805 0.5843 0.077 Uiso 1 1 calc R . .
C22 C 0.9437(4) -0.0715(3) 0.6214(2) 0.0566(10) Uani 1 1 d . . .
H22 H 0.9276 -0.1391 0.6105 0.068 Uiso 1 1 calc R . .
C23 C 0.8190(4) -0.0115(3) 0.6542(2) 0.0402(8) Uani 1 1 d . . .
C24 C 0.8528(3) 0.0878(2) 0.67311(19) 0.0342(7) Uani 1 1 d . . .
C25 C 0.6600(4) -0.0555(3) 0.6665(2) 0.0480(9) Uani 1 1 d . . .
C26 C 0.5382(4) 0.0228(3) 0.6375(3) 0.0699(12) Uani 1 1 d . . .
H26A H 0.4438 -0.0106 0.6375 0.105 Uiso 1 1 calc R . .
H26B H 0.5688 0.0515 0.5785 0.105 Uiso 1 1 calc R . .
H26C H 0.5261 0.0763 0.6785 0.105 Uiso 1 1 calc R . .
C27 C 0.6211(4) -0.0918(3) 0.7634(2) 0.0613(11) Uani 1 1 d . . .
H27A H 0.6944 -0.1430 0.7804 0.092 Uiso 1 1 calc R . .
H27B H 0.5222 -0.1204 0.7705 0.092 Uiso 1 1 calc R . .
H27C H 0.6218 -0.0351 0.8006 0.092 Uiso 1 1 calc R . .
C28 C 0.6511(5) -0.1480(3) 0.6101(3) 0.0803(14) Uani 1 1 d . . .
H28A H 0.7215 -0.2006 0.6282 0.120 Uiso 1 1 calc R . .
H28B H 0.6757 -0.1278 0.5481 0.120 Uiso 1 1 calc R . .
H28C H 0.5503 -0.1734 0.6187 0.120 Uiso 1 1 calc R . .
C29 C 0.5699(4) 0.1673(3) 0.9177(2) 0.0417(8) Uani 1 1 d . . .
C30 C 0.4454(4) 0.1639(3) 0.9929(2) 0.0652(11) Uani 1 1 d . . .
H30A H 0.3929 0.2291 0.9948 0.098 Uiso 1 1 calc R . .
H30B H 0.4878 0.1481 1.0484 0.098 Uiso 1 1 calc R . .
H30C H 0.3758 0.1122 0.9836 0.098 Uiso 1 1 calc R . .
C31 C 0.9570(4) 0.3541(3) 1.0238(2) 0.0481(9) Uani 1 1 d . . .
C32 C 1.0015(5) 0.3635(3) 1.1154(3) 0.0710(13) Uani 1 1 d . . .
H32A H 0.9401 0.3202 1.1572 0.106 Uiso 1 1 calc R . .
H32B H 0.9868 0.4332 1.1312 0.106 Uiso 1 1 calc R . .
H32C H 1.1061 0.3431 1.1170 0.106 Uiso 1 1 calc R . .
Cl1 Cl 0.56265(17) 0.65522(17) 0.44528(11) 0.1400(7) Uani 1 1 d . . .
Cl2 Cl 0.26197(19) 0.70190(15) 0.52269(11) 0.1258(6) Uani 1 1 d . . .
C33 C 0.3743(5) 0.6615(4) 0.4316(3) 0.0898(16) Uani 1 1 d . . .
H33A H 0.3432 0.5943 0.4186 0.108 Uiso 1 1 calc R . .
H33B H 0.3582 0.7078 0.3803 0.108 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.925(2) . ?
Cu1 O3 1.941(2) . ?
Cu1 N2 1.990(2) . ?
Cu1 N1 2.029(3) . ?
O1 C13 1.347(4) . ?
O2 C24 1.381(3) . ?
O2 H2 0.8200 . ?
O3 C29 1.264(4) . ?
O4 C29 1.234(4) . ?
O5 C31 1.210(4) . ?
O6 C31 1.302(4) . ?
N1 C1 1.487(3) . ?
N1 C7 1.487(4) . ?
N1 C18 1.502(4) . ?
N2 C2 1.335(4) . ?
N2 C6 1.338(4) . ?
C1 C2 1.499(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.378(4) . ?
C3 C4 1.384(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.501(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.382(5) . ?
C8 C13 1.393(4) . ?
C9 C10 1.366(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.393(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.413(4) . ?
C12 C14 1.527(5) . ?
C14 C16 1.519(5) . ?
C14 C17 1.531(5) . ?
C14 C15 1.533(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.498(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.377(4) . ?
C19 C24 1.401(4) . ?
C20 C21 1.364(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.362(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.401(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.400(5) . ?
C23 C25 1.535(5) . ?
C25 C27 1.516(5) . ?
C25 C28 1.533(5) . ?
C25 C26 1.540(5) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.499(4) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C32 1.487(5) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
Cl1 C33 1.705(5) . ?
Cl2 C33 1.713(5) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O3 89.01(9) . . ?
O1 Cu1 N2 168.87(9) . . ?
O3 Cu1 N2 94.17(10) . . ?
O1 Cu1 N1 94.29(9) . . ?
O3 Cu1 N1 176.19(9) . . ?
N2 Cu1 N1 82.24(10) . . ?
C13 O1 Cu1 122.98(18) . . ?
C24 O2 H2 109.5 . . ?
C29 O3 Cu1 124.5(2) . . ?
C1 N1 C7 109.4(2) . . ?
C1 N1 C18 110.6(2) . . ?
C7 N1 C18 108.1(2) . . ?
C1 N1 Cu1 104.98(18) . . ?
C7 N1 Cu1 109.22(19) . . ?
C18 N1 Cu1 114.52(19) . . ?
C2 N2 C6 118.9(3) . . ?
C2 N2 Cu1 113.5(2) . . ?
C6 N2 Cu1 127.5(2) . . ?
N1 C1 C2 109.7(3) . . ?
N1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
N2 C2 C3 121.6(3) . . ?
N2 C2 C1 115.3(3) . . ?
C3 C2 C1 123.0(3) . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 118.8(4) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
N2 C6 C5 122.5(3) . . ?
N2 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
N1 C7 C8 112.4(3) . . ?
N1 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C13 120.4(3) . . ?
C9 C8 C7 120.3(3) . . ?
C13 C8 C7 119.3(3) . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 119.3(3) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C12 123.3(3) . . ?
C10 C11 H11 118.3 . . ?
C12 C11 H11 118.3 . . ?
C11 C12 C13 116.2(3) . . ?
C11 C12 C14 120.9(3) . . ?
C13 C12 C14 122.7(3) . . ?
O1 C13 C8 118.5(3) . . ?
O1 C13 C12 121.0(3) . . ?
C8 C13 C12 120.5(3) . . ?
C16 C14 C12 108.4(3) . . ?
C16 C14 C17 109.4(4) . . ?
C12 C14 C17 112.3(3) . . ?
C16 C14 C15 107.4(3) . . ?
C12 C14 C15 113.0(3) . . ?
C17 C14 C15 106.2(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 N1 116.3(3) . . ?
C19 C18 H18A 108.2 . . ?
N1 C18 H18A 108.2 . . ?
C19 C18 H18B 108.2 . . ?
N1 C18 H18B 108.2 . . ?
H18A C18 H18B 107.4 . . ?
C20 C19 C24 119.5(3) . . ?
C20 C19 C18 120.1(3) . . ?
C24 C19 C18 120.4(3) . . ?
C21 C20 C19 120.3(4) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 119.5(3) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 123.9(4) . . ?
C21 C22 H22 118.1 . . ?
C23 C22 H22 118.1 . . ?
C24 C23 C22 114.9(3) . . ?
C24 C23 C25 124.8(3) . . ?
C22 C23 C25 120.2(3) . . ?
O2 C24 C23 125.0(3) . . ?
O2 C24 C19 113.3(3) . . ?
C23 C24 C19 121.7(3) . . ?
C27 C25 C28 107.1(3) . . ?
C27 C25 C23 109.9(3) . . ?
C28 C25 C23 111.4(3) . . ?
C27 C25 C26 109.6(3) . . ?
C28 C25 C26 106.4(3) . . ?
C23 C25 C26 112.2(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O4 C29 O3 125.8(3) . . ?
O4 C29 C30 118.4(3) . . ?
O3 C29 C30 115.8(3) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O5 C31 O6 122.7(3) . . ?
O5 C31 C32 122.4(3) . . ?
O6 C31 C32 114.8(3) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
Cl1 C33 Cl2 113.8(3) . . ?
Cl1 C33 H33A 108.8 . . ?
Cl2 C33 H33A 108.8 . . ?
Cl1 C33 H33B 108.8 . . ?
Cl2 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?

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
O3 Cu1 O1 C13 -150.3(2) . . . . ?
N2 Cu1 O1 C13 102.9(5) . . . . ?
N1 Cu1 O1 C13 31.6(2) . . . . ?
O1 Cu1 O3 C29 97.8(3) . . . . ?
N2 Cu1 O3 C29 -92.9(3) . . . . ?
N1 Cu1 O3 C29 -112.0(14) . . . . ?
O1 Cu1 N1 C1 137.55(19) . . . . ?
O3 Cu1 N1 C1 -12.5(16) . . . . ?
N2 Cu1 N1 C1 -31.82(19) . . . . ?
O1 Cu1 N1 C7 20.34(19) . . . . ?
O3 Cu1 N1 C7 -129.7(14) . . . . ?
N2 Cu1 N1 C7 -149.03(19) . . . . ?
O1 Cu1 N1 C18 -101.01(19) . . . . ?
O3 Cu1 N1 C18 108.9(15) . . . . ?
N2 Cu1 N1 C18 89.6(2) . . . . ?
O1 Cu1 N2 C2 -52.8(6) . . . . ?
O3 Cu1 N2 C2 -159.1(2) . . . . ?
N1 Cu1 N2 C2 19.6(2) . . . . ?
O1 Cu1 N2 C6 126.4(5) . . . . ?
O3 Cu1 N2 C6 20.1(3) . . . . ?
N1 Cu1 N2 C6 -161.2(3) . . . . ?
C7 N1 C1 C2 156.0(3) . . . . ?
C18 N1 C1 C2 -85.1(3) . . . . ?
Cu1 N1 C1 C2 38.9(3) . . . . ?
C6 N2 C2 C3 -3.4(4) . . . . ?
Cu1 N2 C2 C3 175.8(2) . . . . ?
C6 N2 C2 C1 179.3(3) . . . . ?
Cu1 N2 C2 C1 -1.5(3) . . . . ?
N1 C1 C2 N2 -26.1(4) . . . . ?
N1 C1 C2 C3 156.7(3) . . . . ?
N2 C2 C3 C4 2.7(5) . . . . ?
C1 C2 C3 C4 179.8(3) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 C6 -1.9(5) . . . . ?
C2 N2 C6 C5 1.4(4) . . . . ?
Cu1 N2 C6 C5 -177.7(2) . . . . ?
C4 C5 C6 N2 1.3(5) . . . . ?
C1 N1 C7 C8 -177.5(2) . . . . ?
C18 N1 C7 C8 62.1(3) . . . . ?
Cu1 N1 C7 C8 -63.1(3) . . . . ?
N1 C7 C8 C9 -120.1(3) . . . . ?
N1 C7 C8 C13 62.5(4) . . . . ?
C13 C8 C9 C10 -0.3(5) . . . . ?
C7 C8 C9 C10 -177.6(4) . . . . ?
C8 C9 C10 C11 1.3(6) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C10 C11 C12 C14 176.0(4) . . . . ?
Cu1 O1 C13 C8 -44.0(4) . . . . ?
Cu1 O1 C13 C12 136.5(3) . . . . ?
C9 C8 C13 O1 179.4(3) . . . . ?
C7 C8 C13 O1 -3.3(4) . . . . ?
C9 C8 C13 C12 -1.1(5) . . . . ?
C7 C8 C13 C12 176.3(3) . . . . ?
C11 C12 C13 O1 -179.0(3) . . . . ?
C14 C12 C13 O1 4.6(5) . . . . ?
C11 C12 C13 C8 1.5(5) . . . . ?
C14 C12 C13 C8 -174.9(3) . . . . ?
C11 C12 C14 C16 -106.4(4) . . . . ?
C13 C12 C14 C16 69.9(4) . . . . ?
C11 C12 C14 C17 132.7(4) . . . . ?
C13 C12 C14 C17 -51.1(4) . . . . ?
C11 C12 C14 C15 12.5(5) . . . . ?
C13 C12 C14 C15 -171.2(3) . . . . ?
C1 N1 C18 C19 57.8(3) . . . . ?
C7 N1 C18 C19 177.5(3) . . . . ?
Cu1 N1 C18 C19 -60.6(3) . . . . ?
N1 C18 C19 C20 -103.2(3) . . . . ?
N1 C18 C19 C24 79.8(4) . . . . ?
C24 C19 C20 C21 -1.1(5) . . . . ?
C18 C19 C20 C21 -178.2(3) . . . . ?
C19 C20 C21 C22 3.9(6) . . . . ?
C20 C21 C22 C23 -1.8(6) . . . . ?
C21 C22 C23 C24 -3.0(5) . . . . ?
C21 C22 C23 C25 176.7(3) . . . . ?
C22 C23 C24 O2 -176.7(3) . . . . ?
C25 C23 C24 O2 3.6(5) . . . . ?
C22 C23 C24 C19 5.9(4) . . . . ?
C25 C23 C24 C19 -173.8(3) . . . . ?
C20 C19 C24 O2 178.2(3) . . . . ?
C18 C19 C24 O2 -4.7(4) . . . . ?
C20 C19 C24 C23 -4.0(4) . . . . ?
C18 C19 C24 C23 173.1(3) . . . . ?
C24 C23 C25 C27 -82.0(4) . . . . ?
C22 C23 C25 C27 98.3(4) . . . . ?
C24 C23 C25 C28 159.5(3) . . . . ?
C22 C23 C25 C28 -20.2(4) . . . . ?
C24 C23 C25 C26 40.3(4) . . . . ?
C22 C23 C25 C26 -139.5(3) . . . . ?
Cu1 O3 C29 O4 9.7(5) . . . . ?
Cu1 O3 C29 C30 -169.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1529090'
_audit_update_record             
;
2017-01-22 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H29 Cu N3 O4'
_chemical_formula_weight         499.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9760(6)
_cell_length_b                   13.6021(10)
_cell_length_c                   18.6777(10)
_cell_angle_alpha                93.225(5)
_cell_angle_beta                 102.814(5)
_cell_angle_gamma                94.021(5)
_cell_volume                     2458.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5247
_cell_measurement_theta_min      6.7030
_cell_measurement_theta_max      72.3870

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1044
_exptl_absorpt_coefficient_mu    1.541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73497
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16407
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0492
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         72.31
_reflns_number_total             9331
_reflns_number_gt                6566
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1848P)²+3.3017P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9331
_refine_ls_number_parameters     603
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.3003
_refine_ls_wR_factor_gt          0.2095
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001

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 0.80685(7) 0.17821(5) 0.26499(4) 0.0467(3) Uani 1 1 d . . .
Cu2 Cu 0.58989(7) 0.30326(6) 0.64425(4) 0.0504(3) Uani 1 1 d . . .
O2 O 0.8736(4) 0.0476(3) 0.2759(2) 0.0586(10) Uani 1 1 d . . .
O4 O 0.4496(3) 0.3497(3) 0.6923(2) 0.0522(9) Uani 1 1 d . . .
O1 O 0.9710(4) 0.2259(3) 0.2340(2) 0.0558(9) Uani 1 1 d . . .
O5 O 0.4694(4) 0.1860(3) 0.6013(2) 0.0635(11) Uani 1 1 d . . .
N2 N 0.6569(5) 0.1557(4) 0.3192(2) 0.0526(11) Uani 1 1 d . . .
N1 N 0.7241(4) 0.3140(3) 0.2563(3) 0.0506(10) Uani 1 1 d . . .
N6 N 0.7181(5) 0.2363(3) 0.7438(3) 0.0552(11) Uani 1 1 d . . .
N5 N 0.7220(5) 0.2892(4) 0.5785(3) 0.0606(12) Uani 1 1 d . . .
N4 N 0.7275(5) 0.4241(4) 0.6872(3) 0.0594(12) Uani 1 1 d . . .
C42 C 0.4845(5) 0.3906(4) 0.7606(3) 0.0502(12) Uani 1 1 d . . .
C24 C 0.9774(6) 0.0501(4) 0.3282(3) 0.0535(13) Uani 1 1 d . . .
C17 C 0.9658(5) 0.2890(4) 0.1826(3) 0.0530(13) Uani 1 1 d . . .
C19 C 0.6229(5) 0.2384(5) 0.1303(3) 0.0556(13) Uani 1 1 d . . .
N3 N 0.6688(5) 0.1524(4) 0.1497(3) 0.0557(11) Uani 1 1 d . . .
C49 C 0.3623(6) 0.1953(5) 0.5541(3) 0.0574(14) Uani 1 1 d . . .
O3 O 1.0170(6) 0.1167(4) 0.3765(3) 0.0872(16) Uani 1 1 d . . .
C44 C 0.8023(5) 0.3081(5) 0.7855(3) 0.0579(15) Uani 1 1 d . . .
C6 C 0.6011(6) 0.0669(5) 0.3334(3) 0.0622(15) Uani 1 1 d . . .
H6 H 0.6405 0.0100 0.3215 0.075 Uiso 1 1 calc R . .
C8 C 0.8919(6) 0.3748(4) 0.1856(3) 0.0543(13) Uani 1 1 d . . .
C38 C 0.2957(6) 0.2782(5) 0.7963(4) 0.0606(15) Uani 1 1 d . . .
C2 C 0.5995(6) 0.2370(4) 0.3390(3) 0.0566(13) Uani 1 1 d . . .
O6 O 0.3425(6) 0.2708(4) 0.5195(3) 0.0835(14) Uani 1 1 d . . .
C12 C 1.0337(5) 0.2748(5) 0.1237(3) 0.0563(14) Uani 1 1 d . . .
C18 C 0.6094(6) 0.3096(5) 0.1910(4) 0.0607(14) Uani 1 1 d . . .
H18A H 0.6033 0.3749 0.1728 0.073 Uiso 1 1 calc R . .
H18B H 0.5239 0.2915 0.2055 0.073 Uiso 1 1 calc R . .
C37 C 0.4165(5) 0.3586(4) 0.8151(3) 0.0537(13) Uani 1 1 d . . .
C41 C 0.3462(7) 0.1808(5) 0.7733(4) 0.0660(16) Uani 1 1 d . . .
H41A H 0.3843 0.1888 0.7308 0.099 Uiso 1 1 calc R . .
H41B H 0.2704 0.1307 0.7615 0.099 Uiso 1 1 calc R . .
H41C H 0.4160 0.1614 0.8129 0.099 Uiso 1 1 calc R . .
C33 C 0.5920(5) 0.4671(4) 0.7788(4) 0.0580(14) Uani 1 1 d . . .
C43 C 0.8423(6) 0.3946(5) 0.7447(4) 0.0670(17) Uani 1 1 d . . .
H43A H 0.8767 0.4508 0.7800 0.080 Uiso 1 1 calc R . .
H43B H 0.9168 0.3775 0.7220 0.080 Uiso 1 1 calc R . .
C13 C 1.1225(6) 0.1875(5) 0.1210(4) 0.0657(16) Uani 1 1 d . . .
C32 C 0.6556(6) 0.5028(4) 0.7179(4) 0.0690(18) Uani 1 1 d . . .
H32A H 0.5841 0.5237 0.6789 0.083 Uiso 1 1 calc R . .
H32B H 0.7210 0.5594 0.7368 0.083 Uiso 1 1 calc R . .
C47 C 0.7429(8) 0.1404(6) 0.8481(4) 0.079(2) Uani 1 1 d . . .
H47 H 0.7235 0.0810 0.8677 0.095 Uiso 1 1 calc R . .
C9 C 0.8760(7) 0.4377(5) 0.1301(4) 0.0671(16) Uani 1 1 d . . .
H9 H 0.8246 0.4918 0.1325 0.080 Uiso 1 1 calc R . .
C23 C 0.6732(7) 0.0824(6) 0.0984(4) 0.0740(18) Uani 1 1 d . . .
H23 H 0.7042 0.0221 0.1131 0.089 Uiso 1 1 calc R . .
C3 C 0.4851(7) 0.2316(5) 0.3692(4) 0.0666(16) Uani 1 1 d . . .
H3 H 0.4466 0.2888 0.3813 0.080 Uiso 1 1 calc R . .
C10 C 0.9343(7) 0.4224(5) 0.0716(4) 0.0698(17) Uani 1 1 d . . .
H10 H 0.9211 0.4645 0.0335 0.084 Uiso 1 1 calc R . .
C4 C 0.4290(7) 0.1410(6) 0.3811(4) 0.0729(19) Uani 1 1 d . . .
H4 H 0.3504 0.1363 0.4001 0.087 Uiso 1 1 calc R . .
C11 C 1.0145(6) 0.3424(6) 0.0697(4) 0.0688(17) Uani 1 1 d . . .
H11 H 1.0571 0.3338 0.0305 0.083 Uiso 1 1 calc R . .
C48 C 0.6887(6) 0.1557(5) 0.7742(4) 0.0650(16) Uani 1 1 d . . .
H48 H 0.6287 0.1060 0.7453 0.078 Uiso 1 1 calc R . .
C36 C 0.4636(7) 0.4036(5) 0.8861(4) 0.0687(17) Uani 1 1 d . . .
H36 H 0.4198 0.3846 0.9228 0.082 Uiso 1 1 calc R . .
C7 C 0.8343(6) 0.3909(4) 0.2524(4) 0.0599(14) Uani 1 1 d . . .
H7A H 0.9082 0.3914 0.2961 0.072 Uiso 1 1 calc R . .
H7B H 0.7974 0.4550 0.2521 0.072 Uiso 1 1 calc R . .
C31 C 0.7391(7) 0.2084(6) 0.5375(3) 0.0706(18) Uani 1 1 d . . .
H31 H 0.6760 0.1537 0.5339 0.085 Uiso 1 1 calc R . .
C1 C 0.6727(7) 0.3303(5) 0.3245(4) 0.0626(15) Uani 1 1 d . . .
H1A H 0.7495 0.3505 0.3657 0.075 Uiso 1 1 calc R . .
H1B H 0.6103 0.3823 0.3188 0.075 Uiso 1 1 calc R . .
C34 C 0.6377(6) 0.5088(5) 0.8502(4) 0.0668(17) Uani 1 1 d . . .
H34 H 0.7101 0.5581 0.8618 0.080 Uiso 1 1 calc R . .
C45 C 0.8546(7) 0.3013(6) 0.8593(4) 0.076(2) Uani 1 1 d . . .
H45 H 0.9093 0.3540 0.8876 0.092 Uiso 1 1 calc R . .
C35 C 0.5741(7) 0.4759(6) 0.9039(4) 0.079(2) Uani 1 1 d . . .
H35 H 0.6050 0.5022 0.9523 0.095 Uiso 1 1 calc R . .
C5 C 0.4878(7) 0.0576(6) 0.3651(4) 0.0706(18) Uani 1 1 d . . .
H5 H 0.4529 -0.0040 0.3751 0.085 Uiso 1 1 calc R . .
C27 C 0.8114(7) 0.3688(5) 0.5801(4) 0.0720(18) Uani 1 1 d . . .
C26 C 0.7835(7) 0.4572(5) 0.6245(5) 0.078(2) Uani 1 1 d . . .
H26A H 0.8682 0.4993 0.6428 0.093 Uiso 1 1 calc R . .
H26B H 0.7176 0.4951 0.5938 0.093 Uiso 1 1 calc R . .
C22 C 0.6340(8) 0.0948(7) 0.0248(4) 0.088(2) Uani 1 1 d . . .
H22 H 0.6375 0.0442 -0.0102 0.106 Uiso 1 1 calc R . .
C40 C 0.1820(6) 0.3075(5) 0.7338(5) 0.077(2) Uani 1 1 d . . .
H40A H 0.2188 0.3176 0.6912 0.115 Uiso 1 1 calc R . .
H40B H 0.1474 0.3675 0.7489 0.115 Uiso 1 1 calc R . .
H40C H 0.1082 0.2559 0.7220 0.115 Uiso 1 1 calc R . .
C15 C 1.2326(6) 0.1884(7) 0.1925(4) 0.083(2) Uani 1 1 d . . .
H15A H 1.2820 0.2527 0.2031 0.125 Uiso 1 1 calc R . .
H15B H 1.2957 0.1399 0.1872 0.125 Uiso 1 1 calc R . .
H15C H 1.1893 0.1734 0.2321 0.125 Uiso 1 1 calc R . .
C16 C 1.0308(7) 0.0898(5) 0.1103(5) 0.081(2) Uani 1 1 d . . .
H16A H 0.9960 0.0805 0.1537 0.121 Uiso 1 1 calc R . .
H16B H 1.0841 0.0360 0.1020 0.121 Uiso 1 1 calc R . .
H16C H 0.9550 0.0918 0.0687 0.121 Uiso 1 1 calc R . .
C21 C 0.5885(8) 0.1862(8) 0.0040(4) 0.097(3) Uani 1 1 d . . .
H21 H 0.5610 0.1973 -0.0456 0.117 Uiso 1 1 calc R . .
C30 C 0.8412(9) 0.2015(7) 0.5016(4) 0.085(2) Uani 1 1 d . . .
H30 H 0.8492 0.1432 0.4749 0.102 Uiso 1 1 calc R . .
C20 C 0.5847(7) 0.2586(7) 0.0562(4) 0.080(2) Uani 1 1 d . . .
H20 H 0.5573 0.3203 0.0431 0.096 Uiso 1 1 calc R . .
C28 C 0.9193(9) 0.3664(8) 0.5447(5) 0.094(3) Uani 1 1 d . . .
H28 H 0.9815 0.4216 0.5479 0.112 Uiso 1 1 calc R . .
C29 C 0.9332(10) 0.2825(9) 0.5052(5) 0.098(3) Uani 1 1 d . . .
H29 H 1.0048 0.2798 0.4808 0.118 Uiso 1 1 calc R . .
C46 C 0.8255(8) 0.2163(8) 0.8905(5) 0.095(3) Uani 1 1 d . . .
H46 H 0.8616 0.2101 0.9403 0.114 Uiso 1 1 calc R . .
C39 C 0.2308(9) 0.2597(6) 0.8624(5) 0.092(2) Uani 1 1 d . . .
H39A H 0.1558 0.2092 0.8481 0.138 Uiso 1 1 calc R . .
H39B H 0.1971 0.3196 0.8783 0.138 Uiso 1 1 calc R . .
H39C H 0.2992 0.2387 0.9020 0.138 Uiso 1 1 calc R . .
C50 C 0.2523(8) 0.1117(7) 0.5387(4) 0.087(2) Uani 1 1 d . . .
H50A H 0.2062 0.1100 0.5787 0.131 Uiso 1 1 calc R . .
H50B H 0.2931 0.0506 0.5337 0.131 Uiso 1 1 calc R . .
H50C H 0.1869 0.1207 0.4939 0.131 Uiso 1 1 calc R . .
C14 C 1.1967(9) 0.1913(7) 0.0577(5) 0.096(3) Uani 1 1 d . . .
H14A H 1.1299 0.1903 0.0118 0.143 Uiso 1 1 calc R . .
H14B H 1.2496 0.1351 0.0572 0.143 Uiso 1 1 calc R . .
H14C H 1.2571 0.2508 0.0643 0.143 Uiso 1 1 calc R . .
C25 C 1.0580(8) -0.0419(6) 0.3292(6) 0.105(3) Uani 1 1 d . . .
H25A H 1.1535 -0.0223 0.3322 0.157 Uiso 1 1 calc R . .
H25B H 1.0213 -0.0835 0.2850 0.157 Uiso 1 1 calc R . .
H25C H 1.0495 -0.0775 0.3712 0.157 Uiso 1 1 calc R . .
O2W O 0.1615(6) 0.3147(4) 0.3808(4) 0.0940(17) Uani 1 1 d . . .
O1W O 0.2958(14) 0.4620(6) 0.5773(6) 0.199(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.936(4) . ?
Cu1 O2 1.946(4) . ?
Cu1 N2 2.000(4) . ?
Cu1 N1 2.075(4) . ?
Cu1 N3 2.278(5) . ?
Cu2 O4 1.944(4) . ?
Cu2 O5 1.947(4) . ?
Cu2 N5 2.002(5) . ?
Cu2 N4 2.067(5) . ?
Cu2 N6 2.285(5) . ?
O2 C24 1.253(7) . ?
O4 C42 1.325(6) . ?
O1 C17 1.319(7) . ?
O5 C49 1.245(7) . ?
N2 C2 1.352(7) . ?
N2 C6 1.359(8) . ?
N1 C18 1.471(7) . ?
N1 C7 1.479(7) . ?
N1 C1 1.487(7) . ?
N6 C48 1.309(9) . ?
N6 C44 1.332(7) . ?
N5 C31 1.345(8) . ?
N5 C27 1.348(9) . ?
N4 C43 1.482(8) . ?
N4 C26 1.483(9) . ?
N4 C32 1.486(8) . ?
C42 C33 1.410(8) . ?
C42 C37 1.414(8) . ?
C24 O3 1.220(7) . ?
C24 C25 1.533(9) . ?
C17 C12 1.425(8) . ?
C17 C8 1.428(8) . ?
C19 N3 1.326(8) . ?
C19 C20 1.401(9) . ?
C19 C18 1.485(9) . ?
N3 C23 1.322(8) . ?
C49 O6 1.248(8) . ?
C49 C50 1.492(9) . ?
C44 C45 1.372(10) . ?
C44 C43 1.514(10) . ?
C6 C5 1.389(9) . ?
C8 C9 1.370(9) . ?
C8 C7 1.498(9) . ?
C38 C41 1.524(8) . ?
C38 C40 1.529(9) . ?
C38 C37 1.535(8) . ?
C38 C39 1.541(10) . ?
C2 C3 1.380(8) . ?
C2 C1 1.487(9) . ?
C12 C11 1.393(9) . ?
C12 C13 1.536(9) . ?
C37 C36 1.394(9) . ?
C33 C34 1.384(9) . ?
C33 C32 1.509(10) . ?
C13 C15 1.528(10) . ?
C13 C14 1.529(9) . ?
C13 C16 1.537(10) . ?
C47 C46 1.368(12) . ?
C47 C48 1.400(10) . ?
C9 C10 1.359(10) . ?
C23 C22 1.367(11) . ?
C3 C4 1.368(10) . ?
C10 C11 1.399(10) . ?
C4 C5 1.361(10) . ?
C36 C35 1.394(10) . ?
C31 C30 1.344(10) . ?
C34 C35 1.379(11) . ?
C45 C46 1.366(12) . ?
C27 C28 1.385(10) . ?
C27 C26 1.500(11) . ?
C22 C21 1.400(13) . ?
C21 C20 1.354(12) . ?
C30 C29 1.373(13) . ?
C28 C29 1.355(13) . ?

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
O1 Cu1 O2 90.89(17) . . ?
O1 Cu1 N2 164.80(18) . . ?
O2 Cu1 N2 95.81(19) . . ?
O1 Cu1 N1 93.08(18) . . ?
O2 Cu1 N1 176.02(17) . . ?
N2 Cu1 N1 80.26(19) . . ?
O1 Cu1 N3 96.01(17) . . ?
O2 Cu1 N3 99.33(17) . . ?
N2 Cu1 N3 96.34(18) . . ?
N1 Cu1 N3 80.59(18) . . ?
O4 Cu2 O5 90.73(17) . . ?
O4 Cu2 N5 163.6(2) . . ?
O5 Cu2 N5 95.5(2) . . ?
O4 Cu2 N4 92.84(18) . . ?
O5 Cu2 N4 176.41(18) . . ?
N5 Cu2 N4 81.1(2) . . ?
O4 Cu2 N6 97.00(17) . . ?
O5 Cu2 N6 98.53(18) . . ?
N5 Cu2 N6 97.03(19) . . ?
N4 Cu2 N6 80.67(19) . . ?
C24 O2 Cu1 110.7(3) . . ?
C42 O4 Cu2 120.4(3) . . ?
C17 O1 Cu1 121.5(3) . . ?
C49 O5 Cu2 119.2(4) . . ?
C2 N2 C6 117.1(5) . . ?
C2 N2 Cu1 116.1(4) . . ?
C6 N2 Cu1 126.6(4) . . ?
C18 N1 C7 111.4(5) . . ?
C18 N1 C1 110.3(4) . . ?
C7 N1 C1 111.2(5) . . ?
C18 N1 Cu1 109.9(3) . . ?
C7 N1 Cu1 109.0(3) . . ?
C1 N1 Cu1 104.8(4) . . ?
C48 N6 C44 118.4(6) . . ?
C48 N6 Cu2 128.5(4) . . ?
C44 N6 Cu2 108.6(4) . . ?
C31 N5 C27 116.4(6) . . ?
C31 N5 Cu2 128.1(5) . . ?
C27 N5 Cu2 115.3(5) . . ?
C43 N4 C26 108.8(5) . . ?
C43 N4 C32 110.4(5) . . ?
C26 N4 C32 111.5(5) . . ?
C43 N4 Cu2 110.4(4) . . ?
C26 N4 Cu2 105.3(4) . . ?
C32 N4 Cu2 110.3(3) . . ?
O4 C42 C33 119.0(5) . . ?
O4 C42 C37 121.2(5) . . ?
C33 C42 C37 119.9(5) . . ?
O3 C24 O2 126.6(5) . . ?
O3 C24 C25 119.3(6) . . ?
O2 C24 C25 114.2(6) . . ?
O1 C17 C12 121.7(5) . . ?
O1 C17 C8 120.0(5) . . ?
C12 C17 C8 118.4(6) . . ?
N3 C19 C20 121.3(6) . . ?
N3 C19 C18 116.4(5) . . ?
C20 C19 C18 122.3(6) . . ?
C23 N3 C19 119.8(6) . . ?
C23 N3 Cu1 127.7(5) . . ?
C19 N3 Cu1 107.4(4) . . ?
O5 C49 O6 123.3(6) . . ?
O5 C49 C50 117.9(6) . . ?
O6 C49 C50 118.8(6) . . ?
N6 C44 C45 122.2(7) . . ?
N6 C44 C43 115.1(6) . . ?
C45 C44 C43 122.6(6) . . ?
N2 C6 C5 122.7(6) . . ?
C9 C8 C17 121.2(6) . . ?
C9 C8 C7 122.9(6) . . ?
C17 C8 C7 115.9(5) . . ?
C41 C38 C40 109.4(6) . . ?
C41 C38 C37 109.8(5) . . ?
C40 C38 C37 110.5(5) . . ?
C41 C38 C39 107.1(6) . . ?
C40 C38 C39 107.6(6) . . ?
C37 C38 C39 112.4(6) . . ?
N2 C2 C3 122.3(6) . . ?
N2 C2 C1 112.7(5) . . ?
C3 C2 C1 125.0(6) . . ?
C11 C12 C17 117.1(6) . . ?
C11 C12 C13 122.5(6) . . ?
C17 C12 C13 120.3(6) . . ?
N1 C18 C19 113.9(5) . . ?
C36 C37 C42 117.1(6) . . ?
C36 C37 C38 121.8(6) . . ?
C42 C37 C38 121.1(5) . . ?
C34 C33 C42 121.4(6) . . ?
C34 C33 C32 120.7(6) . . ?
C42 C33 C32 117.9(5) . . ?
N4 C43 C44 113.8(4) . . ?
C15 C13 C14 107.5(6) . . ?
C15 C13 C16 109.0(7) . . ?
C14 C13 C16 108.2(6) . . ?
C15 C13 C12 110.4(6) . . ?
C14 C13 C12 111.9(6) . . ?
C16 C13 C12 109.7(5) . . ?
N4 C32 C33 111.5(5) . . ?
C46 C47 C48 117.3(8) . . ?
C10 C9 C8 121.0(7) . . ?
N3 C23 C22 122.8(8) . . ?
C4 C3 C2 119.1(6) . . ?
C9 C10 C11 118.9(6) . . ?
C5 C4 C3 120.2(6) . . ?
C12 C11 C10 123.2(6) . . ?
N6 C48 C47 123.3(6) . . ?
C37 C36 C35 122.3(7) . . ?
N1 C7 C8 112.6(5) . . ?
N5 C31 C30 124.5(8) . . ?
C2 C1 N1 109.2(5) . . ?
C35 C34 C33 118.8(6) . . ?
C46 C45 C44 119.2(7) . . ?
C34 C35 C36 120.4(6) . . ?
C4 C5 C6 118.4(7) . . ?
N5 C27 C28 122.0(8) . . ?
N5 C27 C26 113.6(6) . . ?
C28 C27 C26 124.4(7) . . ?
N4 C26 C27 109.4(5) . . ?
C23 C22 C21 117.7(8) . . ?
C20 C21 C22 120.0(8) . . ?
C31 C30 C29 118.3(8) . . ?
C21 C20 C19 118.4(8) . . ?
C29 C28 C27 119.1(9) . . ?
C28 C29 C30 119.6(7) . . ?
C47 C46 C45 119.5(8) . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        72.31
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         1.718
_refine_diff_density_min         -1.237
_refine_diff_density_rms         0.112
####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1529093'
_audit_update_record             
;
2017-01-22 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H30 Cl Cu F3 N2 O3'
_chemical_formula_weight         574.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   21.3336(5)
_cell_length_b                   10.4005(3)
_cell_length_c                   23.4451(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5202.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3341
_cell_measurement_theta_min      6.0400
_cell_measurement_theta_max      72.1420

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2376
_exptl_absorpt_coefficient_mu    2.587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73412
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12144
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.77
_diffrn_reflns_theta_max         72.28
_reflns_number_total             5017
_reflns_number_gt                3714
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1134P)²+2.5587P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5017
_refine_ls_number_parameters     321
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.2003
_refine_ls_wR_factor_gt          0.1792
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.05239(2) 0.63458(5) 0.68146(2) 0.0564(2) Uani 1 1 d . . .
Cl1 Cl 0.12165(5) 0.78665(13) 0.71002(6) 0.0945(4) Uani 1 1 d . . .
F1 F -0.0474(2) 0.9951(4) 0.59964(16) 0.1519(17) Uani 1 1 d . . .
F2 F -0.1203(2) 1.0848(4) 0.6441(2) 0.1570(17) Uani 1 1 d . . .
F3 F -0.03890(18) 1.0249(3) 0.68814(15) 0.1058(10) Uani 1 1 d . . .
O1 O -0.01092(13) 0.7645(3) 0.67473(13) 0.0720(7) Uani 1 1 d . . .
O2 O 0.07938(15) 0.6381(3) 0.58251(12) 0.0659(7) Uani 1 1 d D . .
N1 N -0.00891(14) 0.4910(3) 0.66282(13) 0.0583(7) Uani 1 1 d . . .
N2 N 0.11240(16) 0.4869(4) 0.69178(13) 0.0682(9) Uani 1 1 d . . .
C1 C 0.0165(2) 0.3684(4) 0.68496(18) 0.0718(11) Uani 1 1 d . . .
H1A H 0.0021 0.2980 0.6613 0.086 Uiso 1 1 calc R . .
H1B H 0.0012 0.3542 0.7234 0.086 Uiso 1 1 calc R . .
C2 C 0.0870(2) 0.3707(4) 0.68538(15) 0.0724(12) Uani 1 1 d . . .
C3 C 0.1224(3) 0.2585(6) 0.6830(2) 0.105(2) Uani 1 1 d . . .
H3A H 0.1036 0.1787 0.6777 0.126 Uiso 1 1 calc R . .
C4 C 0.1867(4) 0.2708(9) 0.6890(3) 0.129(3) Uani 1 1 d . . .
H4A H 0.2122 0.1982 0.6879 0.154 Uiso 1 1 calc R . .
C5 C 0.2125(3) 0.3894(9) 0.6963(3) 0.123(3) Uani 1 1 d . . .
H5A H 0.2557 0.3979 0.7005 0.148 Uiso 1 1 calc R . .
C6 C 0.1749(2) 0.4969(6) 0.6976(2) 0.0887(15) Uani 1 1 d . . .
H6A H 0.1929 0.5775 0.7026 0.106 Uiso 1 1 calc R . .
C7 C -0.06943(19) 0.5160(4) 0.69353(18) 0.0708(10) Uani 1 1 d . . .
H7A H -0.0968 0.4426 0.6880 0.085 Uiso 1 1 calc R . .
H7B H -0.0607 0.5224 0.7340 0.085 Uiso 1 1 calc R . .
C8 C -0.10358(19) 0.6346(4) 0.67523(15) 0.0666(10) Uani 1 1 d . . .
C9 C -0.1679(2) 0.6298(6) 0.6697(2) 0.0833(14) Uani 1 1 d . . .
H9A H -0.1880 0.5511 0.6742 0.100 Uiso 1 1 calc R . .
C10 C -0.2030(2) 0.7363(7) 0.6578(2) 0.1045(19) Uani 1 1 d . . .
H10A H -0.2463 0.7300 0.6539 0.125 Uiso 1 1 calc R . .
C11 C -0.1738(3) 0.8514(7) 0.6519(2) 0.0977(18) Uani 1 1 d . . .
H11A H -0.1976 0.9244 0.6445 0.117 Uiso 1 1 calc R . .
C12 C -0.1087(2) 0.8628(5) 0.65659(16) 0.0730(11) Uani 1 1 d . . .
C13 C -0.07240(18) 0.7528(4) 0.66883(15) 0.0627(9) Uani 1 1 d . . .
C14 C -0.0793(3) 0.9893(5) 0.6479(2) 0.0908(15) Uani 1 1 d . . .
C15 C -0.02094(18) 0.4806(4) 0.60007(16) 0.0625(9) Uani 1 1 d . . .
H15A H -0.0547 0.4195 0.5941 0.075 Uiso 1 1 calc R . .
H15B H -0.0352 0.5635 0.5863 0.075 Uiso 1 1 calc R . .
C16 C 0.03405(18) 0.4396(4) 0.56495(15) 0.0594(8) Uani 1 1 d . . .
C17 C 0.0354(2) 0.3183(4) 0.53935(17) 0.0710(11) Uani 1 1 d . . .
H17A H 0.0029 0.2606 0.5458 0.085 Uiso 1 1 calc R . .
C18 C 0.0846(3) 0.2837(4) 0.50478(17) 0.0782(12) Uani 1 1 d . . .
H18A H 0.0846 0.2035 0.4872 0.094 Uiso 1 1 calc R . .
C19 C 0.1340(2) 0.3669(4) 0.49597(16) 0.0718(11) Uani 1 1 d . . .
H19A H 0.1672 0.3408 0.4731 0.086 Uiso 1 1 calc R . .
C20 C 0.13548(19) 0.4885(4) 0.52029(14) 0.0615(9) Uani 1 1 d . . .
C21 C 0.08384(17) 0.5230(3) 0.55476(14) 0.0541(8) Uani 1 1 d . . .
C22 C 0.1904(2) 0.5806(4) 0.50805(16) 0.0701(10) Uani 1 1 d . . .
C23 C 0.2214(2) 0.6297(5) 0.5633(2) 0.0858(14) Uani 1 1 d . . .
H23A H 0.2362 0.5578 0.5852 0.129 Uiso 1 1 calc R . .
H23B H 0.1913 0.6772 0.5853 0.129 Uiso 1 1 calc R . .
H23C H 0.2561 0.6845 0.5539 0.129 Uiso 1 1 calc R . .
C24 C 0.1666(2) 0.6927(5) 0.4718(2) 0.0877(14) Uani 1 1 d . . .
H24A H 0.1475 0.6599 0.4377 0.132 Uiso 1 1 calc R . .
H24B H 0.2011 0.7475 0.4619 0.132 Uiso 1 1 calc R . .
H24C H 0.1363 0.7409 0.4932 0.132 Uiso 1 1 calc R . .
C25 C 0.2427(3) 0.5170(6) 0.4743(2) 0.1018(17) Uani 1 1 d . . .
H25A H 0.2590 0.4456 0.4955 0.153 Uiso 1 1 calc R . .
H25B H 0.2755 0.5782 0.4675 0.153 Uiso 1 1 calc R . .
H25C H 0.2264 0.4870 0.4385 0.153 Uiso 1 1 calc R . .
O3 O 0.1316(5) 0.8795(8) 0.5855(4) 0.224(3) Uiso 1 1 d D . .
H3 H 0.1475 0.9102 0.6143 0.337 Uiso 1 1 calc R . .
C26 C 0.0885(5) 0.9620(11) 0.5646(5) 0.210(5) Uiso 1 1 d D . .
H26A H 0.0819 1.0306 0.5913 0.315 Uiso 1 1 calc R . .
H26B H 0.0497 0.9173 0.5584 0.315 Uiso 1 1 calc R . .
H26C H 0.1032 0.9969 0.5291 0.315 Uiso 1 1 calc R . .
H2 H 0.077(2) 0.698(4) 0.566(2) 0.082(17) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.917(3) . ?
Cu1 N2 2.014(3) . ?
Cu1 N1 2.032(3) . ?
Cu1 Cl1 2.2657(12) . ?
Cu1 O2 2.391(3) . ?
F1 C14 1.323(6) . ?
F2 C14 1.327(6) . ?
F3 C14 1.330(6) . ?
O1 C13 1.324(5) . ?
O2 C21 1.366(4) . ?
O2 H2 0.73(4) . ?
N1 C1 1.479(5) . ?
N1 C15 1.497(5) . ?
N1 C7 1.501(5) . ?
N2 C2 1.333(6) . ?
N2 C6 1.344(6) . ?
C1 C2 1.503(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.392(7) . ?
C3 C4 1.386(11) . ?
C3 H3A 0.9300 . ?
C4 C5 1.362(11) . ?
C4 H4A 0.9300 . ?
C5 C6 1.377(8) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.496(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.379(6) . ?
C8 C13 1.406(6) . ?
C9 C10 1.367(8) . ?
C9 H9A 0.9300 . ?
C10 C11 1.357(8) . ?
C10 H10A 0.9300 . ?
C11 C12 1.399(7) . ?
C11 H11A 0.9300 . ?
C12 C13 1.411(6) . ?
C12 C14 1.471(7) . ?
C15 C16 1.495(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C21 1.392(5) . ?
C16 C17 1.398(5) . ?
C17 C18 1.374(6) . ?
C17 H17A 0.9300 . ?
C18 C19 1.379(6) . ?
C18 H18A 0.9300 . ?
C19 C20 1.388(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.413(5) . ?
C20 C22 1.541(6) . ?
C22 C25 1.518(6) . ?
C22 C24 1.529(6) . ?
C22 C23 1.542(6) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
O3 C26 1.351(11) . ?
O3 H3 0.8200 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N2 174.41(14) . . ?
O1 Cu1 N1 92.68(13) . . ?
N2 Cu1 N1 82.80(15) . . ?
O1 Cu1 Cl1 89.53(10) . . ?
N2 Cu1 Cl1 94.72(12) . . ?
N1 Cu1 Cl1 174.91(10) . . ?
O1 Cu1 O2 94.53(12) . . ?
N2 Cu1 O2 88.57(12) . . ?
N1 Cu1 O2 87.57(11) . . ?
Cl1 Cu1 O2 96.83(8) . . ?
C13 O1 Cu1 129.9(3) . . ?
C21 O2 Cu1 117.7(2) . . ?
C21 O2 H2 120(4) . . ?
Cu1 O2 H2 120(4) . . ?
C1 N1 C15 110.2(3) . . ?
C1 N1 C7 107.2(3) . . ?
C15 N1 C7 109.7(3) . . ?
C1 N1 Cu1 108.8(2) . . ?
C15 N1 Cu1 112.0(2) . . ?
C7 N1 Cu1 108.9(2) . . ?
C2 N2 C6 119.0(4) . . ?
C2 N2 Cu1 114.8(3) . . ?
C6 N2 Cu1 125.7(4) . . ?
N1 C1 C2 110.8(3) . . ?
N1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
N2 C2 C3 122.9(5) . . ?
N2 C2 C1 115.0(3) . . ?
C3 C2 C1 122.0(5) . . ?
C4 C3 C2 117.2(7) . . ?
C4 C3 H3A 121.4 . . ?
C2 C3 H3A 121.4 . . ?
C5 C4 C3 119.8(6) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
C4 C5 C6 120.1(6) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
N2 C6 C5 120.9(6) . . ?
N2 C6 H6A 119.5 . . ?
C5 C6 H6A 119.5 . . ?
C8 C7 N1 115.1(3) . . ?
C8 C7 H7A 108.5 . . ?
N1 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
N1 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C13 119.5(4) . . ?
C9 C8 C7 118.8(4) . . ?
C13 C8 C7 121.4(4) . . ?
C10 C9 C8 122.4(5) . . ?
C10 C9 H9A 118.8 . . ?
C8 C9 H9A 118.8 . . ?
C11 C10 C9 119.0(5) . . ?
C11 C10 H10A 120.5 . . ?
C9 C10 H10A 120.5 . . ?
C10 C11 C12 121.5(5) . . ?
C10 C11 H11A 119.2 . . ?
C12 C11 H11A 119.2 . . ?
C11 C12 C13 119.5(5) . . ?
C11 C12 C14 119.2(5) . . ?
C13 C12 C14 121.3(4) . . ?
O1 C13 C8 122.5(4) . . ?
O1 C13 C12 119.4(4) . . ?
C8 C13 C12 118.1(4) . . ?
F1 C14 F2 104.3(5) . . ?
F1 C14 F3 105.1(5) . . ?
F2 C14 F3 105.5(5) . . ?
F1 C14 C12 112.2(4) . . ?
F2 C14 C12 113.4(5) . . ?
F3 C14 C12 115.3(4) . . ?
C16 C15 N1 115.3(3) . . ?
C16 C15 H15A 108.5 . . ?
N1 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
N1 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C21 C16 C17 118.2(4) . . ?
C21 C16 C15 121.0(3) . . ?
C17 C16 C15 120.7(4) . . ?
C18 C17 C16 120.4(4) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C17 C18 C19 120.5(4) . . ?
C17 C18 H18A 119.8 . . ?
C19 C18 H18A 119.8 . . ?
C18 C19 C20 121.9(4) . . ?
C18 C19 H19A 119.1 . . ?
C20 C19 H19A 119.1 . . ?
C19 C20 C21 116.6(4) . . ?
C19 C20 C22 120.5(4) . . ?
C21 C20 C22 122.8(3) . . ?
O2 C21 C16 114.3(3) . . ?
O2 C21 C20 123.3(3) . . ?
C16 C21 C20 122.4(3) . . ?
C25 C22 C24 106.6(4) . . ?
C25 C22 C23 105.5(4) . . ?
C24 C22 C23 111.0(4) . . ?
C25 C22 C20 112.6(4) . . ?
C24 C22 C20 108.9(4) . . ?
C23 C22 C20 112.0(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C26 O3 H3 109.5 . . ?
O3 C26 H26A 109.5 . . ?
O3 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O3 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        72.28
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         1.439
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1529088'
_audit_update_record             
;
2017-01-22 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H29 Cu F3 N2 O4'
_chemical_formula_weight         566.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.8961(13)
_cell_length_b                   12.6494(11)
_cell_length_c                   17.4128(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.542(9)
_cell_angle_gamma                90.00
_cell_volume                     2597.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1084
_cell_measurement_theta_min      6.8910
_cell_measurement_theta_max      43.0320

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1172
_exptl_absorpt_coefficient_mu    1.690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84043
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9488
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0978
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.25
_diffrn_reflns_theta_max         71.99
_reflns_number_total             4976
_reflns_number_gt                2013
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0383P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4976
_refine_ls_number_parameters     342
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1607
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1541
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.51759(7) 0.35688(6) 0.55104(4) 0.0717(3) Uani 1 1 d . . .
O2 O 0.4950(3) 0.1912(3) 0.6056(2) 0.0737(12) Uani 1 1 d . . .
O1 O 0.6764(3) 0.3683(3) 0.5749(2) 0.0756(11) Uani 1 1 d . . .
O3 O 0.5050(3) 0.4331(3) 0.6470(2) 0.0832(12) Uani 1 1 d . . .
N1 N 0.5228(4) 0.2818(3) 0.4484(2) 0.0709(13) Uani 1 1 d . . .
O4 O 0.5376(4) 0.2976(4) 0.7297(2) 0.1007(16) Uani 1 1 d . . .
F3 F 0.9788(4) 0.2805(3) 0.7054(2) 0.1452(17) Uani 1 1 d . . .
N2 N 0.3549(4) 0.3767(3) 0.5108(3) 0.0749(14) Uani 1 1 d . . .
F1 F 0.8003(4) 0.2671(4) 0.7107(2) 0.1347(16) Uani 1 1 d . . .
C13 C 0.4084(5) 0.1333(4) 0.5668(3) 0.0640(14) Uani 1 1 d . . .
C12 C 0.3173(5) 0.0904(4) 0.5999(3) 0.0660(15) Uani 1 1 d . . .
C8 C 0.4196(5) 0.1205(4) 0.4884(3) 0.0658(15) Uani 1 1 d . . .
F2 F 0.8702(4) 0.4161(4) 0.6853(2) 0.1416(18) Uani 1 1 d . . .
C24 C 0.7514(6) 0.3165(5) 0.5433(4) 0.0745(18) Uani 1 1 d . . .
C1 C 0.4240(6) 0.3176(5) 0.3949(3) 0.092(2) Uani 1 1 d . . .
H1A H 0.4014 0.2620 0.3576 0.111 Uiso 1 1 calc R . .
H1B H 0.4451 0.3789 0.3666 0.111 Uiso 1 1 calc R . .
C7 C 0.5225(5) 0.1636(4) 0.4575(3) 0.0751(17) Uani 1 1 d . . .
H7A H 0.5895 0.1429 0.4921 0.090 Uiso 1 1 calc R . .
H7B H 0.5276 0.1316 0.4074 0.090 Uiso 1 1 calc R . .
C23 C 0.8552(6) 0.2880(5) 0.5859(4) 0.0824(18) Uani 1 1 d . . .
C2 C 0.3270(6) 0.3450(5) 0.4359(4) 0.085(2) Uani 1 1 d . . .
C11 C 0.2380(5) 0.0364(5) 0.5482(4) 0.0853(19) Uani 1 1 d . . .
H11 H 0.1742 0.0093 0.5669 0.102 Uiso 1 1 calc R . .
C22 C 0.9391(6) 0.2353(6) 0.5536(5) 0.103(2) Uani 1 1 d . . .
H22 H 1.0070 0.2186 0.5839 0.123 Uiso 1 1 calc R . .
C26 C 0.5409(6) 0.3924(6) 0.7132(4) 0.085(2) Uani 1 1 d . . .
C6 C 0.2744(6) 0.4112(4) 0.5498(4) 0.0821(18) Uani 1 1 d . . .
H6 H 0.2954 0.4335 0.6006 0.099 Uiso 1 1 calc R . .
C9 C 0.3398(5) 0.0625(5) 0.4414(3) 0.0857(19) Uani 1 1 d . . .
H9 H 0.3482 0.0516 0.3897 0.103 Uiso 1 1 calc R . .
C19 C 0.7357(6) 0.2844(5) 0.4644(4) 0.0823(18) Uani 1 1 d . . .
C25 C 0.8739(7) 0.3121(6) 0.6689(5) 0.099(2) Uani 1 1 d . . .
C20 C 0.8217(7) 0.2317(5) 0.4326(4) 0.098(2) Uani 1 1 d . . .
H20 H 0.8108 0.2126 0.3806 0.118 Uiso 1 1 calc R . .
C18 C 0.6278(6) 0.3148(5) 0.4148(3) 0.090(2) Uani 1 1 d . . .
H18A H 0.6267 0.2825 0.3641 0.108 Uiso 1 1 calc R . .
H18B H 0.6266 0.3908 0.4078 0.108 Uiso 1 1 calc R . .
C10 C 0.2485(5) 0.0208(5) 0.4711(4) 0.091(2) Uani 1 1 d . . .
H10 H 0.1939 -0.0176 0.4395 0.109 Uiso 1 1 calc R . .
C14 C 0.3022(6) 0.1023(5) 0.6857(4) 0.0847(19) Uani 1 1 d . . .
C16 C 0.4066(5) 0.0637(5) 0.7371(3) 0.102(2) Uani 1 1 d . . .
H16A H 0.4139 -0.0114 0.7311 0.154 Uiso 1 1 calc R . .
H16B H 0.3996 0.0797 0.7902 0.154 Uiso 1 1 calc R . .
H16C H 0.4726 0.0982 0.7227 0.154 Uiso 1 1 calc R . .
C5 C 0.1609(6) 0.4164(5) 0.5202(5) 0.106(2) Uani 1 1 d . . .
H5 H 0.1063 0.4414 0.5493 0.127 Uiso 1 1 calc R . .
C27 C 0.5963(5) 0.4680(5) 0.7738(3) 0.116(3) Uani 1 1 d . . .
H27A H 0.6692 0.4886 0.7609 0.174 Uiso 1 1 calc R . .
H27B H 0.6055 0.4340 0.8235 0.174 Uiso 1 1 calc R . .
H27C H 0.5495 0.5296 0.7755 0.174 Uiso 1 1 calc R . .
C17 C 0.2772(5) 0.2189(5) 0.7016(3) 0.098(2) Uani 1 1 d . . .
H17A H 0.2610 0.2264 0.7539 0.148 Uiso 1 1 calc R . .
H17B H 0.2129 0.2419 0.6664 0.148 Uiso 1 1 calc R . .
H17C H 0.3420 0.2612 0.6944 0.148 Uiso 1 1 calc R . .
C3 C 0.2152(7) 0.3464(5) 0.4024(4) 0.107(2) Uani 1 1 d . . .
H3 H 0.1958 0.3231 0.3518 0.128 Uiso 1 1 calc R . .
C21 C 0.9224(7) 0.2076(6) 0.4772(5) 0.115(3) Uani 1 1 d . . .
H21 H 0.9792 0.1725 0.4553 0.138 Uiso 1 1 calc R . .
C4 C 0.1331(7) 0.3819(6) 0.4441(5) 0.113(3) Uani 1 1 d . . .
H4 H 0.0579 0.3831 0.4214 0.135 Uiso 1 1 calc R . .
C15 C 0.2028(5) 0.0389(5) 0.7060(3) 0.118(3) Uani 1 1 d . . .
H15A H 0.1353 0.0597 0.6731 0.178 Uiso 1 1 calc R . .
H15B H 0.1932 0.0515 0.7591 0.178 Uiso 1 1 calc R . .
H15C H 0.2167 -0.0350 0.6987 0.178 Uiso 1 1 calc R . .
H2 H 0.508(5) 0.216(4) 0.651(3) 0.09(2) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.886(4) . ?
Cu1 O3 1.952(4) . ?
Cu1 N2 1.986(5) . ?
Cu1 N1 2.031(4) . ?
Cu1 O2 2.331(4) . ?
O2 C13 1.368(6) . ?
O1 C24 1.287(7) . ?
O3 C26 1.284(6) . ?
N1 C1 1.473(6) . ?
N1 C7 1.503(6) . ?
N1 C18 1.506(6) . ?
O4 C26 1.236(7) . ?
F3 C25 1.383(7) . ?
N2 C6 1.320(7) . ?
N2 C2 1.363(7) . ?
F1 C25 1.337(8) . ?
C13 C8 1.398(7) . ?
C13 C12 1.402(7) . ?
C12 C11 1.395(6) . ?
C12 C14 1.534(7) . ?
C8 C9 1.380(6) . ?
C8 C7 1.503(7) . ?
F2 C25 1.348(8) . ?
C24 C23 1.402(8) . ?
C24 C19 1.422(7) . ?
C1 C2 1.475(8) . ?
C23 C22 1.380(8) . ?
C23 C25 1.464(9) . ?
C2 C3 1.381(8) . ?
C11 C10 1.379(7) . ?
C22 C21 1.366(8) . ?
C26 C27 1.510(7) . ?
C6 C5 1.382(7) . ?
C9 C10 1.368(7) . ?
C19 C20 1.396(8) . ?
C19 C18 1.500(7) . ?
C20 C21 1.373(8) . ?
C14 C15 1.509(7) . ?
C14 C16 1.514(7) . ?
C14 C17 1.537(7) . ?
C5 C4 1.393(9) . ?
C3 C4 1.366(9) . ?

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
O1 Cu1 O3 87.77(16) . . ?
O1 Cu1 N2 165.86(17) . . ?
O3 Cu1 N2 93.39(19) . . ?
O1 Cu1 N1 94.82(18) . . ?
O3 Cu1 N1 176.82(17) . . ?
N2 Cu1 N1 83.7(2) . . ?
O1 Cu1 O2 98.32(15) . . ?
O3 Cu1 O2 93.97(16) . . ?
N2 Cu1 O2 95.66(16) . . ?
N1 Cu1 O2 87.50(16) . . ?
C13 O2 Cu1 113.6(3) . . ?
C24 O1 Cu1 126.7(4) . . ?
C26 O3 Cu1 121.1(4) . . ?
C1 N1 C7 111.0(4) . . ?
C1 N1 C18 107.6(5) . . ?
C7 N1 C18 109.3(5) . . ?
C1 N1 Cu1 107.4(4) . . ?
C7 N1 Cu1 111.9(3) . . ?
C18 N1 Cu1 109.6(3) . . ?
C6 N2 C2 119.3(6) . . ?
C6 N2 Cu1 126.8(5) . . ?
C2 N2 Cu1 113.8(5) . . ?
O2 C13 C8 112.5(5) . . ?
O2 C13 C12 125.2(5) . . ?
C8 C13 C12 122.3(5) . . ?
C11 C12 C13 114.7(5) . . ?
C11 C12 C14 121.4(6) . . ?
C13 C12 C14 123.9(5) . . ?
C9 C8 C13 119.6(6) . . ?
C9 C8 C7 120.6(5) . . ?
C13 C8 C7 119.6(5) . . ?
O1 C24 C23 121.1(6) . . ?
O1 C24 C19 123.2(6) . . ?
C23 C24 C19 115.7(7) . . ?
N1 C1 C2 112.1(5) . . ?
N1 C7 C8 114.3(5) . . ?
C22 C23 C24 122.8(7) . . ?
C22 C23 C25 118.6(7) . . ?
C24 C23 C25 118.5(7) . . ?
N2 C2 C3 120.0(7) . . ?
N2 C2 C1 115.1(6) . . ?
C3 C2 C1 124.8(7) . . ?
C10 C11 C12 124.0(6) . . ?
C21 C22 C23 120.1(7) . . ?
O4 C26 O3 125.5(6) . . ?
O4 C26 C27 118.5(6) . . ?
O3 C26 C27 115.9(6) . . ?
N2 C6 C5 124.3(6) . . ?
C10 C9 C8 119.9(6) . . ?
C20 C19 C24 120.6(7) . . ?
C20 C19 C18 120.7(7) . . ?
C24 C19 C18 118.5(6) . . ?
F1 C25 F2 104.9(7) . . ?
F1 C25 F3 104.0(6) . . ?
F2 C25 F3 103.7(6) . . ?
F1 C25 C23 115.1(6) . . ?
F2 C25 C23 114.0(6) . . ?
F3 C25 C23 113.9(7) . . ?
C21 C20 C19 120.8(7) . . ?
C19 C18 N1 113.3(5) . . ?
C9 C10 C11 119.3(6) . . ?
C15 C14 C16 107.2(5) . . ?
C15 C14 C12 111.8(5) . . ?
C16 C14 C12 110.6(5) . . ?
C15 C14 C17 107.0(6) . . ?
C16 C14 C17 111.5(5) . . ?
C12 C14 C17 108.7(5) . . ?
C6 C5 C4 115.9(7) . . ?
C4 C3 C2 119.8(8) . . ?
C22 C21 C20 119.9(8) . . ?
C3 C4 C5 120.8(7) . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        71.99
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1529089'
_audit_update_record             
;
2017-01-22 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 Cu F6 N2 O4'
_chemical_formula_weight         577.96

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   20.8318(6)
_cell_length_b                   11.7725(3)
_cell_length_c                   21.1703(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.074(3)
_cell_angle_gamma                90.00
_cell_volume                     4844.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5669
_cell_measurement_theta_min      3.1480
_cell_measurement_theta_max      27.8000

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2344
_exptl_absorpt_coefficient_mu    0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84903
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24174
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         26.50
_reflns_number_total             10019
_reflns_number_gt                7161
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0531P)²+1.0474P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10019
_refine_ls_number_parameters     669
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.42197(9) 0.74459(15) 0.96212(9) 0.0479(4) Uani 1 1 d . . .
O7 O 0.45970(9) 0.76437(16) 0.42731(9) 0.0521(5) Uani 1 1 d . . .
O5 O 0.39004(10) 0.95492(17) 0.42001(9) 0.0562(5) Uani 1 1 d . . .
O2 O 0.48884(9) 0.77422(14) 0.85607(9) 0.0440(4) Uani 1 1 d . . .
H2 H 0.4682 0.8333 0.8565 0.066 Uiso 1 1 calc R . .
N2 N 0.56853(10) 0.70795(17) 1.00631(10) 0.0374(5) Uani 1 1 d . . .
F9 F 0.33782(13) 0.9888(2) 0.27789(11) 0.1113(9) Uani 1 1 d . . .
O1 O 0.40860(10) 0.55468(16) 0.89263(10) 0.0549(5) Uani 1 1 d . . .
N4 N 0.51282(10) 0.79664(17) 0.57173(10) 0.0384(5) Uani 1 1 d . . .
F4 F 0.47912(13) 1.01298(17) 0.81225(13) 0.1023(7) Uani 1 1 d . . .
F5 F 0.56961(13) 1.10630(16) 0.86880(16) 0.1229(10) Uani 1 1 d . . .
O6 O 0.35792(9) 0.73100(15) 0.50148(9) 0.0501(5) Uani 1 1 d . . .
H6A H 0.3568 0.6727 0.4799 0.075 Uiso 1 1 calc R . .
F1 F 0.28260(12) 0.62882(18) 0.78881(14) 0.1027(8) Uani 1 1 d . . .
F10 F 0.31540(14) 0.49170(17) 0.49209(12) 0.1017(7) Uani 1 1 d . . .
N3 N 0.41985(10) 0.95952(16) 0.56494(10) 0.0370(5) Uani 1 1 d . . .
N1 N 0.55427(11) 0.54446(16) 0.91285(10) 0.0391(5) Uani 1 1 d . . .
O4 O 0.39078(12) 0.86392(18) 0.87489(12) 0.0704(6) Uani 1 1 d . . .
F12 F 0.37207(16) 0.39522(16) 0.57971(13) 0.1154(9) Uani 1 1 d . . .
O8 O 0.37552(12) 0.63728(18) 0.40518(11) 0.0712(6) Uani 1 1 d . . .
C26 C 0.52283(12) 0.8486(2) 0.63086(12) 0.0375(5) Uani 1 1 d . . .
F11 F 0.42435(14) 0.49018(18) 0.52690(13) 0.1045(8) Uani 1 1 d . . .
C13 C 0.40220(15) 0.4745(2) 0.84777(14) 0.0490(7) Uani 1 1 d . . .
C15 C 0.56629(14) 0.5887(2) 0.85156(13) 0.0433(6) Uani 1 1 d . . .
H15A H 0.5976 0.5380 0.8408 0.052 Uiso 1 1 calc R . .
H15B H 0.5230 0.5884 0.8134 0.052 Uiso 1 1 calc R . .
C18 C 0.68991(16) 0.8334(3) 0.87338(16) 0.0589(8) Uani 1 1 d . . .
H18 H 0.7356 0.8447 0.8780 0.071 Uiso 1 1 calc R . .
C2 C 0.62709(13) 0.6566(2) 1.01080(13) 0.0416(6) Uani 1 1 d . . .
C21 C 0.55264(13) 0.7983(2) 0.86077(12) 0.0383(5) Uani 1 1 d . . .
C31 C 0.40294(13) 1.0787(2) 0.53978(15) 0.0486(7) Uani 1 1 d . . .
H31A H 0.3945 1.1233 0.5745 0.058 Uiso 1 1 calc R . .
H31B H 0.4425 1.1112 0.5325 0.058 Uiso 1 1 calc R . .
C7 C 0.52779(15) 0.4248(2) 0.89978(14) 0.0513(7) Uani 1 1 d . . .
H7A H 0.5607 0.3797 0.8879 0.062 Uiso 1 1 calc R . .
H7B H 0.5258 0.3941 0.9415 0.062 Uiso 1 1 calc R . .
C16 C 0.59547(13) 0.7064(2) 0.86066(12) 0.0386(6) Uani 1 1 d . . .
C37 C 0.34057(14) 1.0263(2) 0.41860(16) 0.0533(7) Uani 1 1 d . . .
C42 C 0.38877(15) 0.6666(3) 0.70251(15) 0.0547(7) Uani 1 1 d . . .
H42 H 0.3961 0.6543 0.7480 0.066 Uiso 1 1 calc R . .
F3 F 0.26495(12) 0.5171(2) 0.85812(14) 0.1071(8) Uani 1 1 d . . .
C45 C 0.36744(12) 0.7042(2) 0.56577(13) 0.0392(6) Uani 1 1 d . . .
C36 C 0.28535(17) 1.0442(3) 0.35709(18) 0.0678(9) Uani 1 1 d U . .
C11 C 0.3275(2) 0.3612(3) 0.75449(18) 0.0787(11) Uani 1 1 d . . .
H11 H 0.2836 0.3436 0.7246 0.094 Uiso 1 1 calc R . .
F6 F 0.51664(14) 1.00904(18) 0.91916(14) 0.1131(9) Uani 1 1 d . . .
C39 C 0.36025(12) 0.9137(2) 0.58133(14) 0.0427(6) Uani 1 1 d . . .
H39A H 0.3519 0.9637 0.6140 0.051 Uiso 1 1 calc R . .
H39B H 0.3195 0.9149 0.5405 0.051 Uiso 1 1 calc R . .
C27 C 0.56932(15) 0.8070(3) 0.69036(14) 0.0532(7) Uani 1 1 d . . .
H27 H 0.5749 0.8423 0.7313 0.064 Uiso 1 1 calc R . .
C10 C 0.3822(3) 0.2999(3) 0.75257(19) 0.0852(12) Uani 1 1 d . . .
H10 H 0.3756 0.2416 0.7212 0.102 Uiso 1 1 calc R . .
C32 C 0.34206(14) 1.0880(2) 0.47587(17) 0.0536(7) Uani 1 1 d . . .
C1 C 0.61950(13) 0.5468(2) 0.97317(13) 0.0448(6) Uani 1 1 d . . .
H1A H 0.6583 0.5369 0.9586 0.054 Uiso 1 1 calc R . .
H1B H 0.6196 0.4843 1.0031 0.054 Uiso 1 1 calc R . .
C25 C 0.48398(12) 0.9580(2) 0.62565(13) 0.0398(6) Uani 1 1 d . . .
H25A H 0.4726 0.9677 0.6659 0.048 Uiso 1 1 calc R . .
H25B H 0.5130 1.0211 0.6233 0.048 Uiso 1 1 calc R . .
C40 C 0.37062(12) 0.7951(2) 0.60925(13) 0.0379(6) Uani 1 1 d . . .
C41 C 0.38133(13) 0.7755(2) 0.67668(14) 0.0452(6) Uani 1 1 d . . .
H41 H 0.3836 0.8368 0.7051 0.054 Uiso 1 1 calc R . .
C5 C 0.63133(16) 0.8445(2) 1.08791(16) 0.0560(7) Uani 1 1 d . . .
H5 H 0.6314 0.9071 1.1147 0.067 Uiso 1 1 calc R . .
C20 C 0.58052(14) 0.9086(2) 0.86615(14) 0.0472(6) Uani 1 1 d . . .
C29 C 0.59833(16) 0.6609(3) 0.62826(16) 0.0588(8) Uani 1 1 d . . .
H29 H 0.6244 0.5978 0.6262 0.071 Uiso 1 1 calc R . .
C30 C 0.54976(14) 0.7042(2) 0.57079(14) 0.0484(6) Uani 1 1 d . . .
H30 H 0.5422 0.6681 0.5297 0.058 Uiso 1 1 calc R . .
C12 C 0.33619(17) 0.4492(3) 0.80021(16) 0.0595(8) Uani 1 1 d . . .
C17 C 0.66333(14) 0.7257(2) 0.86759(13) 0.0502(7) Uani 1 1 d . . .
H17 H 0.6915 0.6641 0.8683 0.060 Uiso 1 1 calc R . .
C47 C 0.42268(15) 0.6870(3) 0.39245(14) 0.0540(7) Uani 1 1 d . . .
C4 C 0.69177(16) 0.7932(3) 1.09100(18) 0.0670(9) Uani 1 1 d . . .
H4 H 0.7338 0.8222 1.1193 0.080 Uiso 1 1 calc R . .
C44 C 0.37418(13) 0.5931(2) 0.59194(14) 0.0448(6) Uani 1 1 d . . .
C48 C 0.4360(2) 0.6508(3) 0.32983(17) 0.0866(12) Uani 1 1 d . . .
H48A H 0.4829 0.6671 0.3355 0.130 Uiso 1 1 calc R . .
H48B H 0.4058 0.6915 0.2913 0.130 Uiso 1 1 calc R . .
H48C H 0.4278 0.5707 0.3228 0.130 Uiso 1 1 calc R . .
C43 C 0.38510(15) 0.5771(2) 0.66000(16) 0.0548(7) Uani 1 1 d . . .
H43 H 0.3901 0.5036 0.6772 0.066 Uiso 1 1 calc R . .
C14 C 0.27672(19) 0.5183(3) 0.7992(2) 0.0783(10) Uani 1 1 d . . .
C6 C 0.57092(14) 0.7999(2) 1.04382(14) 0.0465(6) Uani 1 1 d . . .
H6 H 0.5298 0.8354 1.0400 0.056 Uiso 1 1 calc R . .
C8 C 0.45871(16) 0.4108(2) 0.84546(14) 0.0504(7) Uani 1 1 d . . .
C9 C 0.4479(2) 0.3248(2) 0.79763(17) 0.0691(9) Uani 1 1 d . . .
H9 H 0.4852 0.2834 0.7958 0.083 Uiso 1 1 calc R . .
C23 C 0.38299(14) 0.8173(2) 0.92547(16) 0.0501(7) Uani 1 1 d . . .
C46 C 0.3712(2) 0.4940(3) 0.54827(19) 0.0708(9) Uani 1 1 d . . .
C24 C 0.32120(17) 0.8540(3) 0.9421(2) 0.0806(11) Uani 1 1 d . . .
H24A H 0.3306 0.8430 0.9895 0.121 Uiso 1 1 calc R . .
H24B H 0.2820 0.8093 0.9163 0.121 Uiso 1 1 calc R . .
H24C H 0.3118 0.9328 0.9309 0.121 Uiso 1 1 calc R . .
C33 C 0.28900(17) 1.1641(3) 0.4704(2) 0.0739(10) Uani 1 1 d . . .
H33 H 0.2901 1.2046 0.5085 0.089 Uiso 1 1 calc R . .
C28 C 0.60757(17) 0.7125(3) 0.68871(16) 0.0649(9) Uani 1 1 d . . .
H28 H 0.6396 0.6839 0.7286 0.078 Uiso 1 1 calc R . .
C19 C 0.64861(16) 0.9235(3) 0.87228(16) 0.0591(8) Uani 1 1 d . . .
H19 H 0.6664 0.9967 0.8757 0.071 Uiso 1 1 calc R . .
C22 C 0.5370(2) 1.0081(3) 0.8660(2) 0.0717(10) Uani 1 1 d . . .
C3 C 0.68945(14) 0.6990(3) 1.05193(17) 0.0641(8) Uani 1 1 d . . .
H3 H 0.7300 0.6640 1.0534 0.077 Uiso 1 1 calc R . .
F2 F 0.21752(13) 0.4867(3) 0.75288(17) 0.1472(11) Uani 1 1 d . . .
C38 C 0.28310(18) 0.9772(3) 0.29699(19) 0.0807(11) Uani 1 1 d U . .
F7 F 0.22814(14) 1.0004(2) 0.24163(13) 0.1374(11) Uani 1 1 d . . .
C35 C 0.23397(19) 1.1222(3) 0.3542(3) 0.0907(13) Uani 1 1 d . . .
H35 H 0.1981 1.1347 0.3133 0.109 Uiso 1 1 calc R . .
Cu1 Cu 0.486044(15) 0.64610(2) 0.934843(15) 0.03756(9) Uani 1 1 d . . .
Cu2 Cu 0.437423(15) 0.85994(3) 0.493774(15) 0.03900(10) Uani 1 1 d . . .
F8 F 0.27952(11) 0.86426(18) 0.30481(11) 0.0909(6) Uani 1 1 d . . .
C34 C 0.2356(2) 1.1807(4) 0.4108(3) 0.0999(14) Uani 1 1 d . . .
H34 H 0.2005 1.2313 0.4086 0.120 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C23 1.241(3) . ?
O3 Cu1 2.0035(17) . ?
O7 C47 1.249(3) . ?
O7 Cu2 1.9826(18) . ?
O5 C37 1.321(3) . ?
O5 Cu2 1.8854(18) . ?
O2 C21 1.327(3) . ?
O2 Cu1 2.2648(17) . ?
N2 C6 1.333(3) . ?
N2 C2 1.334(3) . ?
N2 Cu1 1.975(2) . ?
F9 C38 1.347(4) . ?
O1 C13 1.311(3) . ?
O1 Cu1 1.8769(19) . ?
N4 C30 1.337(3) . ?
N4 C26 1.340(3) . ?
N4 Cu2 1.970(2) . ?
F4 C22 1.329(4) . ?
F5 C22 1.331(4) . ?
O6 C45 1.340(3) . ?
O6 Cu2 2.2953(17) . ?
F1 C14 1.333(4) . ?
F10 C46 1.331(4) . ?
N3 C25 1.484(3) . ?
N3 C31 1.497(3) . ?
N3 C39 1.504(3) . ?
N3 Cu2 2.043(2) . ?
N1 C1 1.493(3) . ?
N1 C15 1.501(3) . ?
N1 C7 1.502(3) . ?
N1 Cu1 2.0357(19) . ?
O4 C23 1.265(3) . ?
F12 C46 1.337(4) . ?
O8 C47 1.253(3) . ?
C26 C27 1.374(4) . ?
C26 C25 1.505(3) . ?
F11 C46 1.340(4) . ?
C13 C8 1.412(4) . ?
C13 C12 1.413(4) . ?
C15 C16 1.497(3) . ?
C18 C19 1.361(4) . ?
C18 C17 1.371(4) . ?
C2 C3 1.372(4) . ?
C2 C1 1.496(4) . ?
C21 C16 1.402(3) . ?
C21 C20 1.410(4) . ?
C31 C32 1.489(4) . ?
C7 C8 1.493(4) . ?
C16 C17 1.387(4) . ?
C37 C32 1.404(4) . ?
C37 C36 1.409(4) . ?
C42 C43 1.370(4) . ?
C42 C41 1.380(4) . ?
F3 C14 1.354(4) . ?
C45 C40 1.397(3) . ?
C45 C44 1.408(3) . ?
C36 C35 1.394(5) . ?
C36 C38 1.484(5) . ?
C11 C10 1.360(6) . ?
C11 C12 1.385(5) . ?
F6 C22 1.339(4) . ?
C39 C40 1.501(3) . ?
C27 C28 1.376(4) . ?
C10 C9 1.390(5) . ?
C32 C33 1.394(4) . ?
C40 C41 1.383(3) . ?
C5 C6 1.373(4) . ?
C5 C4 1.376(4) . ?
C20 C19 1.388(4) . ?
C20 C22 1.480(4) . ?
C29 C28 1.366(4) . ?
C29 C30 1.371(4) . ?
C12 C14 1.476(5) . ?
C47 C48 1.510(4) . ?
C4 C3 1.375(4) . ?
C44 C43 1.388(4) . ?
C44 C46 1.476(4) . ?
C14 F2 1.324(4) . ?
C8 C9 1.392(4) . ?
C23 C24 1.514(4) . ?
C33 C34 1.363(5) . ?
C38 F7 1.339(4) . ?
C38 F8 1.345(4) . ?
C35 C34 1.373(6) . ?

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
C23 O3 Cu1 124.94(18) . . ?
C47 O7 Cu2 125.52(18) . . ?
C37 O5 Cu2 124.57(18) . . ?
C21 O2 Cu1 112.15(14) . . ?
C6 N2 C2 119.2(2) . . ?
C6 N2 Cu1 126.27(17) . . ?
C2 N2 Cu1 114.12(17) . . ?
C13 O1 Cu1 127.13(18) . . ?
C30 N4 C26 119.2(2) . . ?
C30 N4 Cu2 125.82(18) . . ?
C26 N4 Cu2 114.78(16) . . ?
C45 O6 Cu2 112.36(14) . . ?
C25 N3 C31 110.03(19) . . ?
C25 N3 C39 110.90(19) . . ?
C31 N3 C39 108.07(18) . . ?
C25 N3 Cu2 106.72(14) . . ?
C31 N3 Cu2 110.92(16) . . ?
C39 N3 Cu2 110.23(15) . . ?
C1 N1 C15 110.5(2) . . ?
C1 N1 C7 109.63(19) . . ?
C15 N1 C7 109.32(19) . . ?
C1 N1 Cu1 106.80(14) . . ?
C15 N1 Cu1 109.93(14) . . ?
C7 N1 Cu1 110.68(16) . . ?
N4 C26 C27 121.0(2) . . ?
N4 C26 C25 115.0(2) . . ?
C27 C26 C25 123.8(2) . . ?
O1 C13 C8 122.6(3) . . ?
O1 C13 C12 119.2(3) . . ?
C8 C13 C12 118.2(3) . . ?
C16 C15 N1 113.4(2) . . ?
C19 C18 C17 119.1(3) . . ?
N2 C2 C3 120.9(2) . . ?
N2 C2 C1 115.8(2) . . ?
C3 C2 C1 123.2(2) . . ?
O2 C21 C16 117.1(2) . . ?
O2 C21 C20 125.1(2) . . ?
C16 C21 C20 117.8(2) . . ?
C32 C31 N3 114.0(2) . . ?
C8 C7 N1 115.7(2) . . ?
C17 C16 C21 119.9(2) . . ?
C17 C16 C15 121.1(2) . . ?
C21 C16 C15 119.0(2) . . ?
O5 C37 C32 122.3(3) . . ?
O5 C37 C36 119.2(3) . . ?
C32 C37 C36 118.5(3) . . ?
C43 C42 C41 118.8(3) . . ?
O6 C45 C40 116.3(2) . . ?
O6 C45 C44 125.1(2) . . ?
C40 C45 C44 118.5(2) . . ?
C35 C36 C37 119.9(4) . . ?
C35 C36 C38 121.7(3) . . ?
C37 C36 C38 118.4(3) . . ?
C10 C11 C12 121.1(4) . . ?
C40 C39 N3 114.24(19) . . ?
C26 C27 C28 119.3(3) . . ?
C11 C10 C9 119.8(3) . . ?
C33 C32 C37 119.3(3) . . ?
C33 C32 C31 120.9(3) . . ?
C37 C32 C31 119.6(3) . . ?
N1 C1 C2 111.14(19) . . ?
N3 C25 C26 111.51(19) . . ?
C41 C40 C45 120.3(2) . . ?
C41 C40 C39 120.6(2) . . ?
C45 C40 C39 119.1(2) . . ?
C42 C41 C40 121.2(3) . . ?
C6 C5 C4 117.6(3) . . ?
C19 C20 C21 120.1(2) . . ?
C19 C20 C22 120.2(3) . . ?
C21 C20 C22 119.7(3) . . ?
C28 C29 C30 118.4(3) . . ?
N4 C30 C29 122.3(3) . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 C14 120.3(3) . . ?
C13 C12 C14 119.4(3) . . ?
C18 C17 C16 121.6(3) . . ?
O7 C47 O8 125.4(3) . . ?
O7 C47 C48 117.1(3) . . ?
O8 C47 C48 117.6(3) . . ?
C3 C4 C5 119.5(3) . . ?
C43 C44 C45 119.4(3) . . ?
C43 C44 C46 119.8(3) . . ?
C45 C44 C46 120.8(3) . . ?
C42 C43 C44 121.8(3) . . ?
F2 C14 F1 105.6(3) . . ?
F2 C14 F3 104.5(3) . . ?
F1 C14 F3 102.7(3) . . ?
F2 C14 C12 114.1(4) . . ?
F1 C14 C12 114.4(3) . . ?
F3 C14 C12 114.2(3) . . ?
N2 C6 C5 123.0(2) . . ?
C9 C8 C13 119.5(3) . . ?
C9 C8 C7 120.0(3) . . ?
C13 C8 C7 120.0(2) . . ?
C10 C9 C8 120.9(4) . . ?
O3 C23 O4 125.1(2) . . ?
O3 C23 C24 118.1(3) . . ?
O4 C23 C24 116.8(3) . . ?
F10 C46 F12 106.2(3) . . ?
F10 C46 F11 105.0(3) . . ?
F12 C46 F11 105.9(3) . . ?
F10 C46 C44 113.7(3) . . ?
F12 C46 C44 112.7(3) . . ?
F11 C46 C44 112.6(3) . . ?
C34 C33 C32 121.9(4) . . ?
C29 C28 C27 119.7(3) . . ?
C18 C19 C20 121.4(3) . . ?
F4 C22 F5 107.0(3) . . ?
F4 C22 F6 104.7(3) . . ?
F5 C22 F6 105.4(3) . . ?
F4 C22 C20 113.8(3) . . ?
F5 C22 C20 112.7(3) . . ?
F6 C22 C20 112.5(3) . . ?
C2 C3 C4 119.7(3) . . ?
F7 C38 F8 104.0(3) . . ?
F7 C38 F9 105.4(3) . . ?
F8 C38 F9 103.2(3) . . ?
F7 C38 C36 113.3(4) . . ?
F8 C38 C36 114.0(3) . . ?
F9 C38 C36 115.7(3) . . ?
C34 C35 C36 121.0(4) . . ?
O1 Cu1 N2 159.73(9) . . ?
O1 Cu1 O3 85.49(8) . . ?
N2 Cu1 O3 92.99(8) . . ?
O1 Cu1 N1 96.05(8) . . ?
N2 Cu1 N1 84.56(8) . . ?
O3 Cu1 N1 176.72(8) . . ?
O1 Cu1 O2 106.05(8) . . ?
N2 Cu1 O2 94.18(7) . . ?
O3 Cu1 O2 91.32(7) . . ?
N1 Cu1 O2 91.04(7) . . ?
O5 Cu2 N4 160.11(8) . . ?
O5 Cu2 O7 86.28(8) . . ?
N4 Cu2 O7 93.45(8) . . ?
O5 Cu2 N3 95.24(8) . . ?
N4 Cu2 N3 84.24(8) . . ?
O7 Cu2 N3 177.01(8) . . ?
O5 Cu2 O6 105.95(7) . . ?
N4 Cu2 O6 93.93(7) . . ?
O7 Cu2 O6 91.96(7) . . ?
N3 Cu2 O6 90.10(7) . . ?
C33 C34 C35 119.4(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.053
