# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_78-240s
_database_code_depnum_ccdc_archive 'CCDC 1476194'
_audit_update_record             
;
2016-04-24 deposited with the CCDC.
2016-10-31 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 H25 Cu F12 N4 O6'
_chemical_formula_weight         781.04

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   P2(1)/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                   13.0582(5)
_cell_length_b                   15.5436(5)
_cell_length_c                   16.7528(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.039(2)
_cell_angle_gamma                90.00
_cell_volume                     3173.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    7964
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      24.55

_exptl_crystal_description       bulk
_exptl_crystal_colour            'dark green-blue'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1576
_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3014
_exptl_absorpt_correction_T_max  0.4095
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      240(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27859
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         28.17
_reflns_number_total             7716
_reflns_number_gt                4955
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0620P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7716
_refine_ls_number_parameters     523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.948
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.82066(2) 0.564023(17) 0.694921(17) 0.03886(10) Uani 1 1 d . . .
N4R N 0.73909(16) 0.44397(11) 0.72988(12) 0.0415(5) Uani 1 1 d . A .
N3R N 0.71948(15) 0.36405(12) 0.69483(11) 0.0390(4) Uani 1 1 d . A .
C1 C 0.6399(2) 0.54986(19) 0.42769(17) 0.0547(7) Uani 1 1 d . . .
F1 F 0.6702(9) 0.6111(6) 0.3878(6) 0.121(4) Uani 0.50 1 d P A 1
F2 F 0.5353(6) 0.5415(6) 0.3856(7) 0.085(3) Uani 0.50 1 d P A 1
F3 F 0.6808(9) 0.4779(7) 0.4152(6) 0.141(5) Uani 0.50 1 d P A 1
F1A F 0.7171(8) 0.5711(6) 0.4010(6) 0.090(2) Uani 0.50 1 d P A 2
F2A F 0.6400(8) 0.4665(4) 0.4221(6) 0.099(3) Uani 0.50 1 d P A 2
F3A F 0.5482(8) 0.5796(9) 0.3779(7) 0.153(6) Uani 0.50 1 d P A 2
C2 C 0.66781(19) 0.57353(14) 0.52172(15) 0.0400(5) Uani 1 1 d . A .
C3 C 0.59190(19) 0.62076(15) 0.54326(16) 0.0478(6) Uani 1 1 d . . .
H3A H 0.5246 0.6347 0.5002 0.057 Uiso 1 1 calc R A .
C4 C 0.61150(18) 0.64820(14) 0.62599(15) 0.0409(5) Uani 1 1 d . A .
C5 C 0.5253(2) 0.7032(2) 0.64431(19) 0.0525(6) Uani 1 1 d . . .
F4 F 0.5078(15) 0.6689(10) 0.7133(12) 0.090(5) Uani 0.50 1 d P A 1
F5 F 0.5636(19) 0.7913(15) 0.6623(11) 0.060(2) Uani 0.50 1 d P A 1
F6 F 0.4323(15) 0.7032(15) 0.5825(15) 0.080(5) Uani 0.50 1 d P A 1
F5A F 0.5599(19) 0.7744(15) 0.6655(13) 0.078(5) Uani 0.50 1 d P A 2
F6A F 0.4306(15) 0.7145(14) 0.5744(14) 0.059(3) Uani 0.50 1 d P A 2
F4A F 0.4959(13) 0.6744(7) 0.7056(11) 0.060(2) Uani 0.50 1 d P A 2
O1 O 0.76048(12) 0.54744(10) 0.57061(10) 0.0433(4) Uani 1 1 d . . .
O2 O 0.69501(12) 0.63495(10) 0.69152(10) 0.0439(4) Uani 1 1 d . . .
O3 O 0.94850(12) 0.49514(9) 0.70042(10) 0.0422(4) Uani 1 1 d . . .
O4 O 0.88648(13) 0.59623(10) 0.81557(10) 0.0422(4) Uani 1 1 d . . .
C6 C 1.1171(3) 0.4245(2) 0.7547(2) 0.0655(8) Uani 1 1 d . . .
F8A F 1.1656(9) 0.4546(5) 0.7122(9) 0.111(3) Uani 0.50 1 d P A 1
F7A F 1.0671(5) 0.3536(4) 0.7178(7) 0.0890(19) Uani 0.50 1 d P A 1
F9A F 1.1875(10) 0.3986(10) 0.8269(5) 0.140(5) Uani 0.50 1 d P A 1
F7 F 1.1413(12) 0.3606(6) 0.8075(10) 0.149(7) Uani 0.50 1 d P A 2
F8 F 1.0949(8) 0.3968(11) 0.6769(5) 0.161(4) Uani 0.50 1 d P A 2
F9 F 1.2125(6) 0.4643(6) 0.7695(10) 0.127(4) Uani 0.50 1 d P A 2
C7 C 1.03086(19) 0.48398(15) 0.76642(16) 0.0447(6) Uani 1 1 d . A .
C8 C 1.0535(2) 0.52010(17) 0.84721(16) 0.0547(7) Uani 1 1 d . . .
H8A H 1.1204 0.5073 0.8911 0.066 Uiso 1 1 calc R A .
C9 C 0.9804(2) 0.57382(14) 0.86410(15) 0.0436(6) Uani 1 1 d . A .
C10 C 1.0137(3) 0.6156(2) 0.95226(19) 0.0655(8) Uani 1 1 d . . .
F10 F 1.02903(17) 0.69876(12) 0.94631(12) 0.0973(6) Uani 1 1 d . A .
F11 F 1.10467(18) 0.58423(15) 1.00867(12) 0.1135(8) Uani 1 1 d . A .
F12 F 0.93578(18) 0.60703(14) 0.98536(12) 0.0974(6) Uani 1 1 d . A .
N1R N 0.58067(15) 0.25168(13) 0.86946(13) 0.0450(5) Uani 1 1 d . A .
O1R O 0.57448(14) 0.19034(10) 0.81593(12) 0.0531(4) Uani 1 1 d . . .
N2R N 0.60866(16) 0.37885(13) 0.92956(13) 0.0513(5) Uani 1 1 d . A .
O2R O 0.63845(18) 0.45676(12) 0.94500(13) 0.0713(6) Uani 1 1 d . . .
C5R C 0.70559(19) 0.44102(14) 0.79527(15) 0.0428(5) Uani 1 1 d . . .
H5RA H 0.7098 0.4876 0.8321 0.051 Uiso 1 1 calc R A .
C6R C 0.67331(18) 0.31260(15) 0.73661(15) 0.0407(5) Uani 1 1 d . . .
H6RA H 0.6520 0.2550 0.7232 0.049 Uiso 1 1 calc R A .
C7R C 0.66292(17) 0.36012(14) 0.80321(14) 0.0383(5) Uani 1 1 d . A .
C8R C 0.61904(18) 0.33090(15) 0.86529(15) 0.0409(5) Uani 1 1 d . . .
C16R C 0.5206(2) 0.24879(16) 0.93078(18) 0.0516(6) Uani 1 1 d . . .
C15R C 0.5756(2) 0.32387(17) 0.98966(18) 0.0568(7) Uani 1 1 d . A .
C13R C 0.5270(3) 0.16005(18) 0.9720(2) 0.0710(9) Uani 1 1 d . A .
H13A H 0.5813 0.1241 0.9599 0.085 Uiso 1 1 calc R . .
H13B H 0.5489 0.1658 1.0342 0.085 Uiso 1 1 calc R . .
C14R C 0.5047(3) 0.3745(2) 1.0295(2) 0.0887(12) Uani 1 1 d . . .
H14A H 0.4716 0.4247 0.9942 0.106 Uiso 1 1 calc R A .
H14B H 0.4458 0.3380 1.0341 0.106 Uiso 1 1 calc R . .
C11R C 0.3396(3) 0.1853(3) 0.8920(3) 0.1199(16) Uani 1 1 d . . .
H11A H 0.2962 0.2019 0.9266 0.144 Uiso 1 1 calc R A .
H11B H 0.2895 0.1622 0.8375 0.144 Uiso 1 1 calc R . .
C12R C 0.4183(4) 0.1209(3) 0.9361(4) 0.1362(19) Uani 1 1 d . A .
H12A H 0.4190 0.0749 0.8962 0.163 Uiso 1 1 calc R . .
H12B H 0.3981 0.0956 0.9820 0.163 Uiso 1 1 calc R . .
C10R C 0.3969(2) 0.2605(2) 0.8763(2) 0.0745(9) Uani 1 1 d . A .
H10A H 0.3687 0.3132 0.8931 0.089 Uiso 1 1 calc R . .
H10B H 0.3863 0.2645 0.8154 0.089 Uiso 1 1 calc R . .
C19R C 0.5803(5) 0.4025(4) 1.1169(3) 0.148(2) Uani 1 1 d . A .
H19A H 0.6137 0.4584 1.1140 0.178 Uiso 1 1 calc R . .
H19B H 0.5407 0.4069 1.1565 0.178 Uiso 1 1 calc R . .
C18R C 0.6639(6) 0.3349(3) 1.1439(3) 0.160(2) Uani 1 1 d . . .
H18A H 0.6392 0.2879 1.1716 0.192 Uiso 1 1 calc R A .
H18B H 0.7326 0.3579 1.1846 0.192 Uiso 1 1 calc R . .
C17R C 0.6807(3) 0.3029(2) 1.0653(2) 0.0875(10) Uani 1 1 d . A .
H17A H 0.6939 0.2407 1.0691 0.105 Uiso 1 1 calc R . .
H17B H 0.7439 0.3315 1.0585 0.105 Uiso 1 1 calc R . .
C1R C 0.7470(2) 0.34333(17) 0.61966(16) 0.0593(7) Uani 1 1 d . . .
H1RA H 0.6837 0.3571 0.5682 0.071 Uiso 1 1 calc R A .
H1RB H 0.8079 0.3803 0.6198 0.071 Uiso 1 1 calc R . .
C2R C 0.7776(3) 0.2545(2) 0.6143(2) 0.0957(12) Uani 1 1 d . A .
H2RA H 0.7935 0.2463 0.5626 0.144 Uiso 1 1 calc R . .
H2RB H 0.7175 0.2171 0.6130 0.144 Uiso 1 1 calc R . .
H2RC H 0.8421 0.2406 0.6637 0.144 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 O4 1.9563(16) . ?
Cu1 O3 1.9574(14) . ?
Cu1 O2 1.9605(15) . ?
Cu1 O1 1.9611(15) . ?
Cu1 N4R 2.3254(18) . ?
Cu1 O1R 2.4377(16) 2_656 ?
N4R C5R 1.318(3) . ?
N4R N3R 1.359(2) . ?
N3R C6R 1.340(3) . ?
N3R C1R 1.464(3) . ?
C1 F3A 1.275(9) . ?
C1 F1A 1.284(9) . ?
C1 F3 1.289(8) . ?
C1 F2A 1.299(7) . ?
C1 F2 1.299(7) . ?
C1 F1 1.303(9) . ?
C1 C2 1.529(3) . ?
C2 O1 1.260(3) . ?
C2 C3 1.382(3) . ?
C3 C4 1.383(3) . ?
C4 O2 1.256(3) . ?
C4 C5 1.530(3) . ?
C5 F5A 1.20(2) . ?
C5 F6 1.28(2) . ?
C5 F4A 1.298(15) . ?
C5 F4 1.364(17) . ?
C5 F6A 1.38(2) . ?
C5 F5 1.45(2) . ?
O3 C7 1.247(3) . ?
O4 C9 1.254(3) . ?
C6 F8A 1.206(7) . ?
C6 F7 1.291(9) . ?
C6 F9A 1.292(7) . ?
C6 F8 1.303(6) . ?
C6 F7A 1.316(6) . ?
C6 F9 1.332(8) . ?
C6 C7 1.523(4) . ?
C7 C8 1.395(3) . ?
C8 C9 1.371(3) . ?
C9 C10 1.527(4) . ?
C10 F11 1.317(3) . ?
C10 F10 1.318(3) . ?
C10 F12 1.328(3) . ?
N1R O1R 1.291(2) . ?
N1R C8R 1.341(3) . ?
N1R C16R 1.500(3) . ?
O1R Cu1 2.4377(16) 2_646 ?
N2R O2R 1.270(2) . ?
N2R C8R 1.356(3) . ?
N2R C15R 1.497(3) . ?
C5R C7R 1.401(3) . ?
C6R C7R 1.385(3) . ?
C7R C8R 1.430(3) . ?
C16R C15R 1.530(4) . ?
C16R C13R 1.532(4) . ?
C16R C10R 1.555(4) . ?
C15R C17R 1.532(4) . ?
C15R C14R 1.538(4) . ?
C13R C12R 1.461(5) . ?
C14R C19R 1.507(6) . ?
C11R C12R 1.435(5) . ?
C11R C10R 1.462(4) . ?
C19R C18R 1.465(7) . ?
C18R C17R 1.495(5) . ?
C1R C2R 1.449(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Cu1 O3 92.31(6) . . ?
O4 Cu1 O2 86.49(6) . . ?
O3 Cu1 O2 178.58(7) . . ?
O4 Cu1 O1 172.18(6) . . ?
O3 Cu1 O1 89.31(6) . . ?
O2 Cu1 O1 91.78(6) . . ?
O4 Cu1 N4R 90.93(7) . . ?
O3 Cu1 N4R 90.53(6) . . ?
O2 Cu1 N4R 90.25(7) . . ?
O1 Cu1 N4R 96.71(7) . . ?
O4 Cu1 O1R 79.67(6) . 2_656 ?
O3 Cu1 O1R 87.23(6) . 2_656 ?
O2 Cu1 O1R 91.81(6) . 2_656 ?
O1 Cu1 O1R 92.77(6) . 2_656 ?
N4R Cu1 O1R 170.23(7) . 2_656 ?
C5R N4R N3R 105.07(18) . . ?
C5R N4R Cu1 123.77(15) . . ?
N3R N4R Cu1 131.09(14) . . ?
C6R N3R N4R 111.73(18) . . ?
C6R N3R C1R 127.8(2) . . ?
N4R N3R C1R 120.43(18) . . ?
F3A C1 F1A 110.4(7) . . ?
F3A C1 F3 123.7(7) . . ?
F1A C1 F3 75.1(6) . . ?
F3A C1 F2A 109.8(7) . . ?
F1A C1 F2A 102.1(6) . . ?
F3 C1 F2A 27.3(7) . . ?
F3A C1 F2 28.9(8) . . ?
F1A C1 F2 129.9(6) . . ?
F3 C1 F2 103.9(7) . . ?
F2A C1 F2 83.6(6) . . ?
F3A C1 F1 77.7(7) . . ?
F1A C1 F1 38.1(4) . . ?
F3 C1 F1 109.3(7) . . ?
F2A C1 F1 133.1(6) . . ?
F2 C1 F1 104.4(6) . . ?
F3A C1 C2 114.0(6) . . ?
F1A C1 C2 111.7(5) . . ?
F3 C1 C2 114.7(4) . . ?
F2A C1 C2 108.0(5) . . ?
F2 C1 C2 113.5(5) . . ?
F1 C1 C2 110.4(5) . . ?
O1 C2 C3 127.8(2) . . ?
O1 C2 C1 114.2(2) . . ?
C3 C2 C1 118.0(2) . . ?
O1 C2 Cu1 33.99(10) . . ?
C3 C2 Cu1 93.84(15) . . ?
C1 C2 Cu1 148.18(17) . . ?
C2 C3 C4 122.2(2) . . ?
O2 C4 C3 128.0(2) . . ?
O2 C4 C5 112.7(2) . . ?
C3 C4 C5 119.2(2) . . ?
O2 C4 Cu1 34.05(10) . . ?
C3 C4 Cu1 94.00(14) . . ?
C5 C4 Cu1 146.76(17) . . ?
F5A C5 F6 112.7(15) . . ?
F5A C5 F4A 105.8(13) . . ?
F6 C5 F4A 100.1(14) . . ?
F5A C5 F4 105.7(13) . . ?
F6 C5 F4 106.6(14) . . ?
F4A C5 F4 7.4(16) . . ?
F5A C5 F6A 105.2(14) . . ?
F6 C5 F6A 8(2) . . ?
F4A C5 F6A 106.6(13) . . ?
F4 C5 F6A 113.5(13) . . ?
F5A C5 F5 4.8(17) . . ?
F6 C5 F5 108.8(13) . . ?
F4A C5 F5 109.8(11) . . ?
F4 C5 F5 110.0(10) . . ?
F6A C5 F5 101.2(12) . . ?
F5A C5 C4 110.4(12) . . ?
F6 C5 C4 113.0(9) . . ?
F4A C5 C4 114.4(7) . . ?
F4 C5 C4 108.1(8) . . ?
F6A C5 C4 113.7(9) . . ?
F5 C5 C4 110.3(10) . . ?
C2 O1 Cu1 124.96(15) . . ?
C4 O2 Cu1 124.92(15) . . ?
C7 O3 Cu1 124.56(15) . . ?
C9 O4 Cu1 124.31(15) . . ?
F8A C6 F7 130.7(6) . . ?
F8A C6 F9A 109.0(7) . . ?
F7 C6 F9A 37.2(6) . . ?
F8A C6 F8 60.8(6) . . ?
F7 C6 F8 110.1(7) . . ?
F9A C6 F8 131.4(6) . . ?
F8A C6 F7A 108.9(6) . . ?
F7 C6 F7A 68.7(6) . . ?
F9A C6 F7A 104.2(6) . . ?
F8 C6 F7A 50.1(6) . . ?
F8A C6 F9 43.5(5) . . ?
F7 C6 F9 104.3(7) . . ?
F9A C6 F9 70.5(6) . . ?
F8 C6 F9 101.3(7) . . ?
F7A C6 F9 138.5(4) . . ?
F8A C6 C7 114.2(4) . . ?
F7 C6 C7 112.9(5) . . ?
F9A C6 C7 112.3(5) . . ?
F8 C6 C7 114.9(3) . . ?
F7A C6 C7 107.7(3) . . ?
F9 C6 C7 112.3(4) . . ?
O3 C7 C8 128.2(2) . . ?
O3 C7 C6 114.4(2) . . ?
C8 C7 C6 117.4(2) . . ?
O3 C7 Cu1 34.36(10) . . ?
C8 C7 Cu1 93.92(15) . . ?
C6 C7 Cu1 148.66(19) . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 Cu1 60.81(13) . . ?
C7 C8 Cu1 60.83(13) . . ?
O4 C9 C8 128.8(2) . . ?
O4 C9 C10 112.4(2) . . ?
C8 C9 C10 118.8(2) . . ?
O4 C9 Cu1 34.44(10) . . ?
C8 C9 Cu1 94.42(15) . . ?
C10 C9 Cu1 146.63(18) . . ?
F11 C10 F10 107.1(3) . . ?
F11 C10 F12 107.0(3) . . ?
F10 C10 F12 106.8(3) . . ?
F11 C10 C9 114.0(2) . . ?
F10 C10 C9 110.0(2) . . ?
F12 C10 C9 111.5(2) . . ?
O1R N1R C8R 125.0(2) . . ?
O1R N1R C16R 122.39(19) . . ?
C8R N1R C16R 111.11(19) . . ?
N1R O1R Cu1 138.56(14) . 2_646 ?
O2R N2R C8R 125.1(2) . . ?
O2R N2R C15R 123.3(2) . . ?
C8R N2R C15R 110.8(2) . . ?
N4R C5R C7R 111.8(2) . . ?
N4R C5R Cu1 36.52(10) . . ?
C7R C5R Cu1 148.32(16) . . ?
N3R C6R C7R 107.2(2) . . ?
C6R C7R C5R 104.18(19) . . ?
C6R C7R C8R 126.7(2) . . ?
C5R C7R C8R 129.1(2) . . ?
N1R C8R N2R 108.5(2) . . ?
N1R C8R C7R 125.8(2) . . ?
N2R C8R C7R 125.7(2) . . ?
N1R C16R C15R 100.32(18) . . ?
N1R C16R C13R 112.3(2) . . ?
C15R C16R C13R 117.3(2) . . ?
N1R C16R C10R 106.4(2) . . ?
C15R C16R C10R 115.9(2) . . ?
C13R C16R C10R 104.3(2) . . ?
N2R C15R C16R 100.6(2) . . ?
N2R C15R C17R 106.8(2) . . ?
C16R C15R C17R 116.4(2) . . ?
N2R C15R C14R 111.3(2) . . ?
C16R C15R C14R 117.0(2) . . ?
C17R C15R C14R 104.5(3) . . ?
C12R C13R C16R 107.5(3) . . ?
C19R C14R C15R 106.4(3) . . ?
C12R C11R C10R 109.4(3) . . ?
C11R C12R C13R 109.4(3) . . ?
C11R C10R C16R 107.0(3) . . ?
C18R C19R C14R 104.4(4) . . ?
C19R C18R C17R 107.1(4) . . ?
C18R C17R C15R 106.7(4) . . ?
C2R C1R N3R 114.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.17
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.052
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_134
_database_code_depnum_ccdc_archive 'CCDC 1476195'
_audit_update_record             
;
2016-04-24 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H23 N4 O2'
_chemical_formula_weight         303.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   18.0709(5)
_cell_length_b                   11.8731(4)
_cell_length_c                   16.6240(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.7250(10)
_cell_angle_gamma                90
_cell_volume                     3213.29(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      63.94

_exptl_crystal_description       bulk
_exptl_crystal_colour            dark
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             1304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.686
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22304
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.714
_diffrn_reflns_theta_max         66.987
_diffrn_reflns_theta_full        66.987
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measured_fraction_theta_full 0.903
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_Laue_measured_fraction_full 0.903
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.903
_reflns_number_total             5165
_reflns_number_gt                4232
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0931P)²+1.0624P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5165
_refine_ls_number_parameters     471
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1710
_refine_ls_wR_factor_gt          0.1617
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.08459(10) -0.15423(14) -0.24509(12) 0.0748(5) Uani 1 1 d . . . . .
N2 N 0.11592(10) -0.06787(15) -0.19532(12) 0.0540(5) Uani 1 1 d . . . . .
C3 C 0.07691(12) 0.04634(18) -0.21553(14) 0.0522(5) Uani 1 1 d D . . . .
C4 C 0.0950(9) 0.0923(16) -0.2935(10) 0.081(7) Uani 0.5 1 d D . P A 1
H4A H 0.1384 0.1483 -0.2721 0.097 Uiso 0.5 1 calc R U P A 1
H4B H 0.1107 0.0319 -0.3222 0.097 Uiso 0.5 1 calc R U P A 1
C5 C 0.0134(4) 0.1446(6) -0.3574(4) 0.0805(16) Uani 0.5 1 d D . P A 1
H5A H 0.0091 0.1483 -0.4175 0.097 Uiso 0.5 1 calc R U P A 1
H5B H 0.0076 0.2199 -0.3382 0.097 Uiso 0.5 1 calc R U P A 1
C6 C -0.0504(8) 0.0669(12) -0.3531(9) 0.112(7) Uani 0.5 1 d D . P A 1
H6A H -0.1037 0.1032 -0.3744 0.134 Uiso 0.5 1 calc R U P A 1
H6B H -0.0555 -0.0017 -0.3868 0.134 Uiso 0.5 1 calc R U P A 1
C7 C -0.0138(13) 0.045(2) -0.2539(8) 0.062(5) Uani 0.5 1 d D . P A 1
H72A H -0.0321 -0.0281 -0.2431 0.074 Uiso 0.5 1 calc R U P A 1
H72B H -0.0324 0.1017 -0.2251 0.074 Uiso 0.5 1 calc R U P A 1
C42 C 0.0944(7) 0.1007(14) -0.2897(9) 0.056(5) Uani 0.5 1 d D . P A 2
H42A H 0.1456 0.0730 -0.2878 0.067 Uiso 0.5 1 calc R U P A 2
H42B H 0.0974 0.1820 -0.2837 0.067 Uiso 0.5 1 calc R U P A 2
C52 C 0.0209(4) 0.0649(7) -0.3770(4) 0.0873(18) Uani 0.5 1 d D . P A 2
H52A H 0.0118 0.1183 -0.4246 0.105 Uiso 0.5 1 calc R U P A 2
H52B H 0.0294 -0.0094 -0.3957 0.105 Uiso 0.5 1 calc R U P A 2
C62 C -0.0476(5) 0.0648(12) -0.3532(6) 0.084(5) Uani 0.5 1 d D . P A 2
H62A H -0.0880 0.0098 -0.3896 0.101 Uiso 0.5 1 calc R U P A 2
H62B H -0.0736 0.1383 -0.3658 0.101 Uiso 0.5 1 calc R U P A 2
C72 C -0.0201(14) 0.037(2) -0.2545(10) 0.073(6) Uani 0.5 1 d D . P A 2
H7A H -0.0419 0.0904 -0.2264 0.087 Uiso 0.5 1 calc R U P A 2
H7B H -0.0368 -0.0386 -0.2470 0.087 Uiso 0.5 1 calc R U P A 2
C8 C 0.12236(13) 0.10229(19) -0.12342(15) 0.0561(5) Uani 1 1 d . . . . .
C9 C 0.13584(18) 0.2294(2) -0.1207(2) 0.0796(8) Uani 1 1 d . . . . .
H9A H 0.1872 0.2469 -0.1233 0.095 Uiso 1 1 calc R U . . .
H9B H 0.0913 0.2659 -0.1705 0.095 Uiso 1 1 calc R U . . .
C10 C 0.1381(2) 0.2678(3) -0.0334(3) 0.1121(13) Uani 1 1 d . . . . .
H10A H 0.1921 0.2567 0.0153 0.135 Uiso 1 1 calc R U . . .
H10B H 0.1232 0.3466 -0.0359 0.135 Uiso 1 1 calc R U . . .
C11 C 0.0754(3) 0.1938(4) -0.0228(3) 0.1183(13) Uani 1 1 d . . . . .
H11A H 0.0857 0.1892 0.0395 0.142 Uiso 1 1 calc R U . . .
H11B H 0.0204 0.2230 -0.0571 0.142 Uiso 1 1 calc R U . . .
C12 C 0.08474(17) 0.0806(2) -0.05688(18) 0.0749(7) Uani 1 1 d . . . . .
H12A H 0.0318 0.0437 -0.0867 0.090 Uiso 1 1 calc R U . . .
H12B H 0.1207 0.0331 -0.0081 0.090 Uiso 1 1 calc R U . . .
N13 N 0.20202(10) 0.03916(15) -0.08929(12) 0.0551(5) Uani 1 1 d . . . . .
O14 O 0.26691(10) 0.07379(15) -0.02344(12) 0.0745(5) Uani 1 1 d . . . . .
C15 C 0.19162(12) -0.06302(18) -0.12725(14) 0.0511(5) Uani 1 1 d . . . . .
C16 C 0.25089(13) -0.15268(18) -0.09821(14) 0.0527(5) Uani 1 1 d . . . . .
C17 C 0.33042(14) -0.1513(2) -0.02701(16) 0.0621(6) Uani 1 1 d . . . . .
H17A H 0.3540 -0.0886 0.0085 0.075 Uiso 1 1 calc R U . . .
N18 N 0.36739(12) -0.25018(18) -0.01685(14) 0.0679(6) Uani 1 1 d . . . . .
N19 N 0.31213(12) -0.31567(17) -0.08239(13) 0.0642(5) Uani 1 1 d . . . . .
C20 C 0.3329(2) -0.4327(2) -0.08958(19) 0.0807(8) Uani 1 1 d . . . . .
H20A H 0.3086 -0.4541 -0.1521 0.097 Uiso 1 1 calc R U . . .
H20B H 0.3920 -0.4394 -0.0668 0.097 Uiso 1 1 calc R U . . .
C21 C 0.3054(4) -0.5075(3) -0.0425(5) 0.192(3) Uani 1 1 d . . . . .
H21A H 0.3207 -0.5830 -0.0495 0.288 Uiso 1 1 calc R U . . .
H21B H 0.3302 -0.4878 0.0197 0.288 Uiso 1 1 calc R U . . .
H21C H 0.2468 -0.5026 -0.0656 0.288 Uiso 1 1 calc R U . . .
C22 C 0.24221(15) -0.2601(2) -0.13204(15) 0.0597(6) Uani 1 1 d . . . . .
H22A H 0.1966 -0.2889 -0.1802 0.072 Uiso 1 1 calc R U . . .
O1A O 0.42512(10) 0.00518(13) 0.18195(13) 0.0704(5) Uani 1 1 d . . . . .
N2A N 0.39132(10) 0.08960(14) 0.20077(11) 0.0488(4) Uani 1 1 d . . . . .
C3A C 0.42522(12) 0.20667(17) 0.21170(13) 0.0472(5) Uani 1 1 d . . . . .
C4A C 0.4064(10) 0.2548(16) 0.1202(13) 0.061(5) Uani 0.5 1 d . . P B 1
H4AA H 0.3886 0.1949 0.0762 0.074 Uiso 0.5 1 calc R U P B 1
H4AB H 0.3622 0.3093 0.1035 0.074 Uiso 0.5 1 calc R U P B 1
C5A C 0.4804(6) 0.3101(5) 0.1211(6) 0.0512(18) Uani 0.5 1 d . . P B 1
H5AA H 0.4884 0.3856 0.1458 0.061 Uiso 0.5 1 calc R U P B 1
H5AB H 0.4798 0.3118 0.0625 0.061 Uiso 0.5 1 calc R U P B 1
C6A C 0.5476(10) 0.221(2) 0.1884(17) 0.075(5) Uani 0.5 1 d . . P B 1
H6AA H 0.5445 0.1479 0.1607 0.090 Uiso 0.5 1 calc R U P B 1
H6AB H 0.6034 0.2494 0.2119 0.090 Uiso 0.5 1 calc R U P B 1
C7A C 0.5148(12) 0.218(2) 0.2590(13) 0.069(5) Uani 0.5 1 d . . P B 1
H7AA H 0.5380 0.1543 0.2989 0.083 Uiso 0.5 1 calc R U P B 1
H7AB H 0.5294 0.2864 0.2941 0.083 Uiso 0.5 1 calc R U P B 1
C41 C 0.4021(11) 0.2492(15) 0.1134(12) 0.059(5) Uani 0.5 1 d . . P B 2
H41A H 0.3805 0.1889 0.0700 0.070 Uiso 0.5 1 calc R U P B 2
H41B H 0.3630 0.3109 0.0965 0.070 Uiso 0.5 1 calc R U P B 2
C51 C 0.4867(10) 0.2880(17) 0.1245(11) 0.193(9) Uani 0.5 1 d . . P B 2
H51A H 0.4913 0.2704 0.0699 0.231 Uiso 0.5 1 calc R U P B 2
H51B H 0.4892 0.3693 0.1308 0.231 Uiso 0.5 1 calc R U P B 2
C61 C 0.5479(12) 0.247(2) 0.1888(16) 0.078(5) Uani 0.5 1 d . . P B 2
H61A H 0.5901 0.3040 0.2143 0.093 Uiso 0.5 1 calc R U P B 2
H61B H 0.5703 0.1855 0.1677 0.093 Uiso 0.5 1 calc R U P B 2
C71 C 0.5227(10) 0.2031(17) 0.2611(11) 0.052(3) Uani 0.5 1 d . . P B 2
H71A H 0.5436 0.2517 0.3132 0.062 Uiso 0.5 1 calc R U P B 2
H71B H 0.5424 0.1270 0.2793 0.062 Uiso 0.5 1 calc R U P B 2
C8A C 0.37803(12) 0.26342(17) 0.25911(14) 0.0491(5) Uani 1 1 d . . . . .
C9A C 0.35519(17) 0.3870(2) 0.23735(19) 0.0704(7) Uani 1 1 d . . . . .
H9AA H 0.3943 0.4242 0.2208 0.084 Uiso 1 1 calc R U . . .
H9AB H 0.3009 0.3938 0.1882 0.084 Uiso 1 1 calc R U . . .
C10A C 0.3569(2) 0.4387(3) 0.3207(2) 0.0891(9) Uani 1 1 d . . . . .
H10C H 0.3654 0.5195 0.3220 0.107 Uiso 1 1 calc R U . . .
H10D H 0.3065 0.4235 0.3260 0.107 Uiso 1 1 calc R U . . .
C11A C 0.4280(2) 0.3812(3) 0.3919(2) 0.0959(10) Uani 1 1 d . . . . .
H11C H 0.4262 0.3883 0.4491 0.115 Uiso 1 1 calc R U . . .
H11D H 0.4793 0.4126 0.3967 0.115 Uiso 1 1 calc R U . . .
C12A C 0.41928(16) 0.2582(2) 0.36242(15) 0.0677(7) Uani 1 1 d . . . . .
H12C H 0.3853 0.2171 0.3842 0.081 Uiso 1 1 calc R U . . .
H12D H 0.4726 0.2221 0.3843 0.081 Uiso 1 1 calc R U . . .
N13A N 0.30335(10) 0.19088(15) 0.22645(12) 0.0548(5) Uani 1 1 d . . . . .
O14A O 0.23856(11) 0.21925(17) 0.23452(16) 0.0901(6) Uani 1 1 d . . . . .
C15A C 0.31656(12) 0.08914(17) 0.20013(13) 0.0467(5) Uani 1 1 d . . . . .
C16A C 0.25996(12) -0.00287(18) 0.17570(14) 0.0515(5) Uani 1 1 d . . . . .
C17A C 0.18292(14) -0.0082(2) 0.17808(16) 0.0642(6) Uani 1 1 d . . . . .
H17B H 0.1611 0.0502 0.1984 0.077 Uiso 1 1 calc R U . . .
N18A N 0.14554(14) -0.1047(2) 0.14845(18) 0.0823(7) Uani 1 1 d . . . . .
N19A N 0.19751(15) -0.16293(19) 0.12546(18) 0.0851(7) Uani 1 1 d . . . . .
C20A C 0.1722(3) -0.2733(3) 0.0806(3) 0.1353(17) Uani 1 1 d D . . . .
H20C H 0.1172 -0.2895 0.0737 0.162 Uiso 1 1 calc R U . . .
H20D H 0.1695 -0.2669 0.0212 0.162 Uiso 1 1 calc R U . . .
C21A C 0.2193(4) -0.3593(4) 0.1205(5) 0.197(3) Uani 1 1 d D . . . .
H21D H 0.1974 -0.4262 0.0859 0.295 Uiso 1 1 calc R U . . .
H21E H 0.2737 -0.3460 0.1261 0.295 Uiso 1 1 calc R U . . .
H21F H 0.2213 -0.3687 0.1788 0.295 Uiso 1 1 calc R U . . .
C22A C 0.26671(15) -0.1051(2) 0.14131(18) 0.0686(7) Uani 1 1 d . . . . .
H22B H 0.3106 -0.1299 0.1309 0.082 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.284(2) . ?
N2 C15 1.346(3) . ?
N2 C3 1.498(3) . ?
C3 C42 1.541(14) . ?
C3 C7 1.48(2) . ?
C3 C8 1.539(3) . ?
C3 C72 1.59(2) . ?
C3 C4 1.567(14) . ?
C4 C5 1.525(13) . ?
C5 C6 1.503(13) . ?
C6 C7 1.510(14) . ?
C42 C52 1.542(13) . ?
C52 C62 1.454(11) . ?
C62 C72 1.529(14) . ?
C8 N13 1.499(3) . ?
C8 C9 1.527(3) . ?
C8 C12 1.551(3) . ?
C9 C10 1.504(5) . ?
C10 C11 1.503(6) . ?
C11 C12 1.497(4) . ?
N13 O14 1.276(2) . ?
N13 C15 1.343(3) . ?
C15 C16 1.437(3) . ?
C16 C22 1.376(3) . ?
C16 C17 1.411(3) . ?
C17 N18 1.325(3) . ?
N18 N19 1.358(3) . ?
N19 C22 1.344(3) . ?
N19 C20 1.458(3) . ?
C20 C21 1.408(5) . ?
O1A N2A 1.281(2) . ?
N2A C15A 1.346(3) . ?
N2A C3A 1.498(3) . ?
C3A C7A 1.466(19) . ?
C3A C4A 1.520(17) . ?
C3A C8A 1.545(3) . ?
C3A C41 1.584(14) . ?
C3A C71 1.588(17) . ?
C4A C5A 1.484(19) . ?
C5A C6A 1.63(3) . ?
C6A C7A 1.53(3) . ?
C41 C51 1.53(2) . ?
C51 C61 1.26(3) . ?
C61 C71 1.55(3) . ?
C8A N13A 1.490(3) . ?
C8A C9A 1.525(3) . ?
C8A C12A 1.549(3) . ?
C9A C10A 1.503(4) . ?
C10A C11A 1.483(5) . ?
C11A C12A 1.526(4) . ?
N13A O14A 1.280(2) . ?
N13A C15A 1.341(3) . ?
C15A C16A 1.430(3) . ?
C16A C22A 1.370(3) . ?
C16A C17A 1.411(3) . ?
C17A N18A 1.313(3) . ?
N18A N19A 1.348(3) . ?
N19A C22A 1.349(3) . ?
N19A C20A 1.479(4) . ?
C20A C21A 1.310(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
O1 N2 C15 125.36(19) . . ?
O1 N2 C3 123.04(17) . . ?
C15 N2 C3 110.96(17) . . ?
N2 C3 C42 108.6(6) . . ?
N2 C3 C7 114.2(9) . . ?
N2 C3 C8 99.88(16) . . ?
C42 C3 C8 114.1(6) . . ?
C7 C3 C8 116.6(7) . . ?
N2 C3 C72 110.9(9) . . ?
C42 C3 C72 106.1(7) . . ?
C8 C3 C72 117.1(7) . . ?
N2 C3 C4 104.7(7) . . ?
C7 C3 C4 103.8(7) . . ?
C8 C3 C4 117.4(7) . . ?
C5 C4 C3 103.4(9) . . ?
C4 C5 C6 104.3(9) . . ?
C7 C6 C5 100.2(11) . . ?
C6 C7 C3 110.3(12) . . ?
C3 C42 C52 104.2(9) . . ?
C62 C52 C42 103.4(7) . . ?
C52 C62 C72 111.9(10) . . ?
C3 C72 C62 102.2(12) . . ?
N13 C8 C9 111.63(19) . . ?
N13 C8 C3 99.83(17) . . ?
C9 C8 C3 117.8(2) . . ?
N13 C8 C12 107.04(18) . . ?
C9 C8 C12 104.9(2) . . ?
C3 C8 C12 115.34(19) . . ?
C10 C9 C8 105.4(3) . . ?
C11 C10 C9 103.3(3) . . ?
C12 C11 C10 105.4(3) . . ?
C11 C12 C8 106.1(3) . . ?
O14 N13 C15 125.69(18) . . ?
O14 N13 C8 122.52(18) . . ?
C15 N13 C8 111.01(17) . . ?
N13 C15 N2 108.52(19) . . ?
N13 C15 C16 125.43(19) . . ?
N2 C15 C16 126.0(2) . . ?
C22 C16 C17 104.3(2) . . ?
C22 C16 C15 127.9(2) . . ?
C17 C16 C15 127.8(2) . . ?
N18 C17 C16 111.7(2) . . ?
C17 N18 N19 104.51(19) . . ?
C22 N19 N18 112.31(19) . . ?
C22 N19 C20 128.6(2) . . ?
N18 N19 C20 119.1(2) . . ?
C21 C20 N19 113.0(3) . . ?
N19 C22 C16 107.1(2) . . ?
O1A N2A C15A 125.30(17) . . ?
O1A N2A C3A 122.84(15) . . ?
C15A N2A C3A 111.16(16) . . ?
C7A C3A N2A 116.5(10) . . ?
C7A C3A C4A 102.6(10) . . ?
N2A C3A C4A 109.0(8) . . ?
C7A C3A C8A 114.4(9) . . ?
N2A C3A C8A 100.33(15) . . ?
C4A C3A C8A 114.4(6) . . ?
N2A C3A C41 105.1(7) . . ?
C8A C3A C41 115.5(7) . . ?
N2A C3A C71 110.0(7) . . ?
C8A C3A C71 118.8(7) . . ?
C41 C3A C71 106.2(9) . . ?
C5A C4A C3A 110.3(12) . . ?
C4A C5A C6A 96.8(10) . . ?
C7A C6A C5A 96.9(14) . . ?
C3A C7A C6A 107.3(13) . . ?
C51 C41 C3A 99.8(12) . . ?
C61 C51 C41 116.8(17) . . ?
C51 C61 C71 110.1(17) . . ?
C61 C71 C3A 102.9(13) . . ?
N13A C8A C9A 111.14(18) . . ?
N13A C8A C3A 100.09(15) . . ?
C9A C8A C3A 116.83(18) . . ?
N13A C8A C12A 107.76(17) . . ?
C9A C8A C12A 104.58(19) . . ?
C3A C8A C12A 116.23(18) . . ?
C10A C9A C8A 106.2(2) . . ?
C11A C10A C9A 102.2(2) . . ?
C10A C11A C12A 104.6(2) . . ?
C11A C12A C8A 104.5(2) . . ?
O14A N13A C15A 124.86(18) . . ?
O14A N13A C8A 122.31(17) . . ?
C15A N13A C8A 112.22(16) . . ?
N13A C15A N2A 108.29(17) . . ?
N13A C15A C16A 125.06(18) . . ?
N2A C15A C16A 126.66(19) . . ?
C22A C16A C17A 103.9(2) . . ?
C22A C16A C15A 127.8(2) . . ?
C17A C16A C15A 128.2(2) . . ?
N18A C17A C16A 112.4(2) . . ?
C17A N18A N19A 104.2(2) . . ?
N18A N19A C22A 112.6(2) . . ?
N18A N19A C20A 119.8(3) . . ?
C22A N19A C20A 127.4(3) . . ?
C21A C20A N19A 116.4(4) . . ?
N19A C22A C16A 106.8(2) . . ?

_refine_diff_density_max         0.430
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.042



####################################################################### 
# 
# 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_78
_database_code_depnum_ccdc_archive 'CCDC 1476196'
_audit_update_record             
;
2016-04-24 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 Cu F12 N4 O6'
_chemical_formula_weight         781.04

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'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   13.113(6)
_cell_length_b                   15.597(7)
_cell_length_c                   16.766(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.173(19)
_cell_angle_gamma                90
_cell_volume                     3198(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3605
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      22.70

_exptl_crystal_description       bulk
_exptl_crystal_colour            'dark green-blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_F_000             1576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.799
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20570
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.116
_diffrn_reflns_theta_max         28.334
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7920
_reflns_number_gt                4391
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0639P)²+0.1810P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7920
_refine_ls_number_parameters     523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1391
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.82084(3) 0.56369(2) 0.69580(2) 0.04671(14) Uani 1 1 d . . . . .
N4R N 0.7388(2) 0.44348(15) 0.72987(16) 0.0504(6) Uani 1 1 d . . . . .
N3R N 0.7191(2) 0.36414(14) 0.69443(15) 0.0476(6) Uani 1 1 d . . . . .
C1 C 0.6417(4) 0.5522(3) 0.4289(2) 0.0661(9) Uani 1 1 d . . . . .
F1 F 0.6613(15) 0.6172(8) 0.3878(6) 0.136(4) Uani 0.5 1 d . . P A 1
F2 F 0.5398(9) 0.5371(9) 0.3904(8) 0.114(5) Uani 0.5 1 d . . P A 1
F3 F 0.6924(14) 0.4873(12) 0.4152(7) 0.183(8) Uani 0.5 1 d . . P A 1
F1A F 0.7196(9) 0.5725(9) 0.4028(6) 0.100(3) Uani 0.5 1 d . . P A 2
F2A F 0.6390(11) 0.4693(5) 0.4223(7) 0.108(4) Uani 0.5 1 d . . P A 2
F3A F 0.5523(12) 0.5815(13) 0.3780(7) 0.167(8) Uani 0.5 1 d . . P A 2
C2 C 0.6697(3) 0.57504(18) 0.52362(19) 0.0472(7) Uani 1 1 d . . . . .
C3 C 0.5948(3) 0.6213(2) 0.5451(2) 0.0578(8) Uani 1 1 d . . . . .
H3A H 0.5287 0.6355 0.5024 0.069 Uiso 1 1 calc R U . . .
C4 C 0.6136(3) 0.64761(18) 0.6278(2) 0.0481(7) Uani 1 1 d . . . . .
C5 C 0.5272(4) 0.7020(3) 0.6455(3) 0.0651(9) Uani 1 1 d . . . . .
F4 F 0.5173(19) 0.6684(14) 0.7163(15) 0.111(7) Uani 0.5 1 d . . P B 1
F5 F 0.5658(17) 0.7880(14) 0.6614(12) 0.076(3) Uani 0.5 1 d . . P B 1
F6 F 0.438(2) 0.7002(17) 0.5863(18) 0.110(7) Uani 0.5 1 d . . P B 1
F5A F 0.5579(18) 0.7737(15) 0.6681(14) 0.106(7) Uani 0.5 1 d . . P B 2
F6A F 0.4296(16) 0.7124(14) 0.5763(16) 0.070(3) Uani 0.5 1 d . . P B 2
F4A F 0.4940(18) 0.6733(10) 0.7060(12) 0.071(3) Uani 0.5 1 d . . P B 2
O1 O 0.76135(18) 0.54851(12) 0.57171(13) 0.0514(5) Uani 1 1 d . . . . .
O2 O 0.69574(18) 0.63405(12) 0.69276(13) 0.0523(5) Uani 1 1 d . . . . .
O3 O 0.94766(18) 0.49546(12) 0.70023(13) 0.0509(5) Uani 1 1 d . . . . .
O4 O 0.88663(18) 0.59533(12) 0.81617(13) 0.0495(5) Uani 1 1 d . . . . .
C6 C 1.1157(4) 0.4256(3) 0.7545(3) 0.0754(11) Uani 1 1 d . . . . .
F8A F 1.1714(13) 0.4607(8) 0.7209(13) 0.124(4) Uani 0.5 1 d . . P C 1
F7A F 1.0678(7) 0.3595(7) 0.7111(9) 0.104(2) Uani 0.5 1 d . . P C 1
F9A F 1.1792(13) 0.3932(13) 0.8254(6) 0.138(5) Uani 0.5 1 d . . P C 1
F7 F 1.123(2) 0.3549(8) 0.791(2) 0.214(12) Uani 0.5 1 d . . P C 2
F8 F 1.1035(13) 0.4136(14) 0.6720(5) 0.150(5) Uani 0.5 1 d . . P C 2
F9 F 1.2153(8) 0.4589(11) 0.7805(16) 0.158(7) Uani 0.5 1 d . . P C 2
C7 C 1.0295(3) 0.48517(18) 0.7656(2) 0.0510(8) Uani 1 1 d . . . . .
C8 C 1.0527(3) 0.5204(2) 0.8466(2) 0.0642(9) Uani 1 1 d . . . . .
H8A H 1.1188 0.5075 0.8899 0.077 Uiso 1 1 calc R U . . .
C9 C 0.9802(3) 0.57395(19) 0.8640(2) 0.0522(8) Uani 1 1 d . . . . .
C10 C 1.0147(4) 0.6150(3) 0.9520(3) 0.0768(11) Uani 1 1 d . . . . .
F10 F 1.0302(3) 0.69772(16) 0.94565(17) 0.1220(10) Uani 1 1 d . . . . .
F11 F 1.1034(3) 0.5842(2) 1.00772(17) 0.1371(12) Uani 1 1 d . . . . .
F12 F 0.9371(3) 0.60807(18) 0.98500(15) 0.1156(9) Uani 1 1 d . . . . .
N1R N 0.5802(2) 0.25199(15) 0.86798(17) 0.0530(7) Uani 1 1 d . . . . .
O1R O 0.5747(2) 0.19069(13) 0.81472(15) 0.0645(6) Uani 1 1 d . . . . .
N2R N 0.6076(2) 0.37799(16) 0.92827(17) 0.0607(7) Uani 1 1 d . . . . .
O2R O 0.6374(2) 0.45549(15) 0.94420(17) 0.0863(9) Uani 1 1 d . . . . .
C5R C 0.7054(3) 0.44034(18) 0.79522(19) 0.0519(8) Uani 1 1 d . . . . .
H5RA H 0.7098 0.4861 0.8319 0.062 Uiso 1 1 calc R U . . .
C6R C 0.6728(2) 0.31316(18) 0.73583(19) 0.0490(7) Uani 1 1 d . . . . .
H6RA H 0.6515 0.2565 0.7222 0.059 Uiso 1 1 calc R U . . .
C7R C 0.6626(2) 0.35982(17) 0.80250(18) 0.0461(7) Uani 1 1 d . . . . .
C8R C 0.6183(2) 0.33031(18) 0.8645(2) 0.0496(7) Uani 1 1 d . . . . .
C16R C 0.5184(3) 0.2490(2) 0.9280(2) 0.0615(9) Uani 1 1 d . . . . .
C15R C 0.5743(3) 0.3230(2) 0.9878(2) 0.0668(10) Uani 1 1 d . . . . .
C13R C 0.5243(3) 0.1601(2) 0.9686(3) 0.0837(13) Uani 1 1 d . . . . .
H13A H 0.5751 0.1238 0.9542 0.100 Uiso 1 1 calc R U . . .
H13B H 0.5490 0.1650 1.0304 0.100 Uiso 1 1 calc R U . . .
C14R C 0.5026(4) 0.3743(3) 1.0268(3) 0.1000(16) Uani 1 1 d . . . . .
H14A H 0.4720 0.4247 0.9926 0.120 Uiso 1 1 calc R U . . .
H14B H 0.4432 0.3390 1.0300 0.120 Uiso 1 1 calc R U . . .
C11R C 0.3378(5) 0.1870(5) 0.8897(4) 0.142(2) Uani 1 1 d . . . . .
H11A H 0.2944 0.2046 0.9230 0.170 Uiso 1 1 calc R U . . .
H11B H 0.2890 0.1632 0.8360 0.170 Uiso 1 1 calc R U . . .
C12R C 0.4167(6) 0.1242(4) 0.9356(6) 0.170(3) Uani 1 1 d . . . . .
H12A H 0.4154 0.0768 0.8979 0.205 Uiso 1 1 calc R U . . .
H12B H 0.3977 0.1021 0.9825 0.205 Uiso 1 1 calc R U . . .
C10R C 0.3968(3) 0.2608(3) 0.8734(3) 0.0902(13) Uani 1 1 d . . . . .
H10A H 0.3696 0.3136 0.8890 0.108 Uiso 1 1 calc R U . . .
H10B H 0.3869 0.2636 0.8133 0.108 Uiso 1 1 calc R U . . .
C19R C 0.5785(8) 0.3995(5) 1.1150(4) 0.175(3) Uani 1 1 d . . . . .
H19A H 0.6109 0.4552 1.1136 0.209 Uiso 1 1 calc R U . . .
H19B H 0.5393 0.4022 1.1541 0.209 Uiso 1 1 calc R U . . .
C18R C 0.6618(9) 0.3342(5) 1.1414(4) 0.196(4) Uani 1 1 d . . . . .
H18A H 0.6391 0.2879 1.1700 0.235 Uiso 1 1 calc R U . . .
H18B H 0.7296 0.3580 1.1808 0.235 Uiso 1 1 calc R U . . .
C17R C 0.6777(4) 0.3016(3) 1.0635(3) 0.1026(15) Uani 1 1 d . . . . .
H17A H 0.6895 0.2401 1.0676 0.123 Uiso 1 1 calc R U . . .
H17B H 0.7407 0.3288 1.0569 0.123 Uiso 1 1 calc R U . . .
C1R C 0.7466(4) 0.3438(2) 0.6192(2) 0.0735(11) Uani 1 1 d . . . . .
H1RA H 0.6845 0.3585 0.5683 0.088 Uiso 1 1 calc R U . . .
H1RB H 0.8073 0.3799 0.6201 0.088 Uiso 1 1 calc R U . . .
C2R C 0.7754(5) 0.2565(3) 0.6122(3) 0.1118(18) Uani 1 1 d . . . . .
H2RA H 0.7920 0.2495 0.5612 0.168 Uiso 1 1 calc R U . . .
H2RB H 0.8383 0.2414 0.6612 0.168 Uiso 1 1 calc R U . . .
H2RC H 0.7153 0.2199 0.6093 0.168 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O4 1.950(2) . ?
Cu1 O3 1.953(2) . ?
Cu1 O1 1.955(2) . ?
Cu1 O2 1.959(2) . ?
Cu1 N4R 2.333(2) . ?
Cu1 O1R 2.451(2) 2_656 ?
N4R C5R 1.320(3) . ?
N4R N3R 1.357(3) . ?
N3R C6R 1.336(3) . ?
N3R C1R 1.467(3) . ?
C1 F3A 1.260(11) . ?
C1 F2 1.278(11) . ?
C1 F3 1.277(11) . ?
C1 F1A 1.288(8) . ?
C1 F2A 1.297(9) . ?
C1 F1 1.303(9) . ?
C1 C2 1.537(4) . ?
C2 O1 1.252(4) . ?
C2 C3 1.367(4) . ?
C3 C4 1.379(4) . ?
C4 O2 1.243(3) . ?
C4 C5 1.528(4) . ?
C5 F5A 1.20(2) . ?
C5 F6 1.23(3) . ?
C5 F4A 1.319(16) . ?
C5 F4 1.35(2) . ?
C5 F6A 1.39(2) . ?
C5 F5 1.42(2) . ?
O3 C7 1.236(4) . ?
O4 C9 1.244(4) . ?
C6 F8A 1.203(8) . ?
C6 F7 1.247(11) . ?
C6 F9A 1.283(9) . ?
C6 F7A 1.287(8) . ?
C6 F9 1.324(10) . ?
C6 F8 1.346(8) . ?
C6 C7 1.525(5) . ?
C7 C8 1.394(4) . ?
C8 C9 1.373(4) . ?
C9 C10 1.520(5) . ?
C10 F10 1.317(4) . ?
C10 F11 1.293(5) . ?
C10 F12 1.327(4) . ?
N1R O1R 1.292(3) . ?
N1R C8R 1.329(4) . ?
N1R C16R 1.504(3) . ?
O1R Cu1 2.451(2) 2_646 ?
N2R O2R 1.269(3) . ?
N2R C8R 1.351(4) . ?
N2R C15R 1.494(4) . ?
C5R C7R 1.399(4) . ?
C6R C7R 1.380(4) . ?
C7R C8R 1.437(4) . ?
C16R C15R 1.531(5) . ?
C16R C13R 1.534(5) . ?
C16R C10R 1.536(5) . ?
C15R C17R 1.523(6) . ?
C15R C14R 1.548(4) . ?
C13R C12R 1.431(7) . ?
C14R C19R 1.506(8) . ?
C11R C12R 1.430(8) . ?
C11R C10R 1.468(6) . ?
C19R C18R 1.441(10) . ?
C18R C17R 1.484(7) . ?
C1R C2R 1.429(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Cu1 O3 92.65(9) . . ?
O4 Cu1 O1 171.68(8) . . ?
O3 Cu1 O1 88.94(9) . . ?
O4 Cu1 O2 86.47(9) . . ?
O3 Cu1 O2 178.78(10) . . ?
O1 Cu1 O2 91.81(9) . . ?
O4 Cu1 N4R 91.19(9) . . ?
O3 Cu1 N4R 90.82(9) . . ?
O1 Cu1 N4R 96.96(9) . . ?
O2 Cu1 N4R 90.05(9) . . ?
O4 Cu1 O1R 79.64(8) . 2_656 ?
O3 Cu1 O1R 87.30(8) . 2_656 ?
O1 Cu1 O1R 92.29(8) . 2_656 ?
O2 Cu1 O1R 91.71(8) . 2_656 ?
N4R Cu1 O1R 170.53(9) . 2_656 ?
C5R N4R N3R 105.2(2) . . ?
C5R N4R Cu1 123.62(19) . . ?
N3R N4R Cu1 131.15(16) . . ?
C6R N3R N4R 111.5(2) . . ?
C6R N3R C1R 128.1(3) . . ?
N4R N3R C1R 120.4(2) . . ?
F2 C1 F3 106.3(10) . . ?
F3A C1 F1A 109.8(8) . . ?
F3A C1 F2A 108.3(10) . . ?
F1A C1 F2A 102.5(6) . . ?
F2 C1 F1 104.2(8) . . ?
F3 C1 F1 107.8(8) . . ?
F3A C1 C2 115.6(6) . . ?
F2 C1 C2 112.4(6) . . ?
F3 C1 C2 115.1(6) . . ?
F1A C1 C2 111.8(5) . . ?
F2A C1 C2 108.0(6) . . ?
F1 C1 C2 110.3(5) . . ?
O1 C2 C3 128.2(3) . . ?
O1 C2 C1 113.8(3) . . ?
C3 C2 C1 117.9(3) . . ?
O1 C2 Cu1 34.31(13) . . ?
C3 C2 Cu1 93.9(2) . . ?
C1 C2 Cu1 148.1(2) . . ?
C2 C3 C4 122.5(3) . . ?
C2 C3 Cu1 61.27(19) . . ?
C4 C3 Cu1 61.30(18) . . ?
O2 C4 C3 127.9(3) . . ?
O2 C4 C5 113.1(3) . . ?
C3 C4 C5 119.0(3) . . ?
O2 C4 Cu1 34.28(12) . . ?
C3 C4 Cu1 93.65(19) . . ?
C5 C4 Cu1 147.3(3) . . ?
F5A C5 F4A 103.9(13) . . ?
F6 C5 F4 109.7(16) . . ?
F5A C5 F6A 104.8(15) . . ?
F4A C5 F6A 102.7(13) . . ?
F6 C5 F5 110.0(15) . . ?
F4 C5 F5 110.1(12) . . ?
F5A C5 C4 113.0(10) . . ?
F6 C5 C4 112.6(13) . . ?
F4A C5 C4 115.8(9) . . ?
F4 C5 C4 105.7(10) . . ?
F6A C5 C4 115.2(10) . . ?
F5 C5 C4 108.8(9) . . ?
C2 O1 Cu1 124.54(18) . . ?
C4 O2 Cu1 124.79(18) . . ?
C7 O3 Cu1 123.99(18) . . ?
C9 O4 Cu1 124.29(19) . . ?
F8A C6 F9A 108.1(8) . . ?
F8A C6 F7A 110.8(8) . . ?
F9A C6 F7A 103.2(8) . . ?
F7 C6 F9 107.1(11) . . ?
F7 C6 F8 109.8(11) . . ?
F9 C6 F8 97.5(8) . . ?
F8A C6 C7 112.5(5) . . ?
F7 C6 C7 114.1(6) . . ?
F9A C6 C7 112.9(6) . . ?
F7A C6 C7 109.0(5) . . ?
F9 C6 C7 114.0(6) . . ?
F8 C6 C7 113.1(5) . . ?
O3 C7 C8 128.8(3) . . ?
O3 C7 C6 114.5(3) . . ?
C8 C7 C6 116.7(3) . . ?
O3 C7 Cu1 34.82(13) . . ?
C8 C7 Cu1 94.0(2) . . ?
C6 C7 Cu1 149.3(3) . . ?
C9 C8 C7 121.5(3) . . ?
C9 C8 Cu1 60.9(2) . . ?
C7 C8 Cu1 60.63(19) . . ?
O4 C9 C8 128.6(3) . . ?
O4 C9 C10 113.0(3) . . ?
C8 C9 C10 118.4(3) . . ?
O4 C9 Cu1 34.51(13) . . ?
C8 C9 Cu1 94.2(2) . . ?
C10 C9 Cu1 147.2(3) . . ?
F10 C10 F11 107.4(4) . . ?
F10 C10 F12 106.1(3) . . ?
F11 C10 F12 107.1(4) . . ?
F10 C10 C9 109.6(3) . . ?
F11 C10 C9 114.8(3) . . ?
F12 C10 C9 111.5(3) . . ?
O1R N1R C8R 125.3(2) . . ?
O1R N1R C16R 122.1(2) . . ?
C8R N1R C16R 111.1(2) . . ?
N1R O1R Cu1 139.0(2) . 2_646 ?
O2R N2R C8R 125.4(2) . . ?
O2R N2R C15R 123.2(2) . . ?
C8R N2R C15R 110.6(3) . . ?
N4R C5R C7R 111.7(2) . . ?
N4R C5R Cu1 36.65(14) . . ?
C7R C5R Cu1 148.32(19) . . ?
N3R C6R C7R 107.6(2) . . ?
C6R C7R C5R 104.1(2) . . ?
C6R C7R C8R 126.8(3) . . ?
C5R C7R C8R 129.1(3) . . ?
N1R C8R N2R 108.8(2) . . ?
N1R C8R C7R 125.7(3) . . ?
N2R C8R C7R 125.5(3) . . ?
N1R C16R C15R 99.7(2) . . ?
N1R C16R C13R 111.8(2) . . ?
C15R C16R C13R 117.2(3) . . ?
N1R C16R C10R 106.9(3) . . ?
C15R C16R C10R 116.6(3) . . ?
C13R C16R C10R 104.3(3) . . ?
N2R C15R C17R 107.3(3) . . ?
N2R C15R C16R 100.5(3) . . ?
C17R C15R C16R 116.9(3) . . ?
N2R C15R C14R 110.8(3) . . ?
C17R C15R C14R 104.7(3) . . ?
C16R C15R C14R 116.4(3) . . ?
C12R C13R C16R 107.4(4) . . ?
C19R C14R C15R 105.2(5) . . ?
C12R C11R C10R 108.0(5) . . ?
C11R C12R C13R 111.1(5) . . ?
C11R C10R C16R 107.4(4) . . ?
C18R C19R C14R 106.0(5) . . ?
C19R C18R C17R 107.6(6) . . ?
C18R C17R C15R 107.1(5) . . ?
C2R C1R N3R 115.6(3) . . ?

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.053

_shelxl_version_number           2014/6



_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_87b-150s
_database_code_depnum_ccdc_archive 'CCDC 1476197'
_audit_update_record             
;
2016-04-24 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 Cu F12 N4 O6'
_chemical_formula_weight         781.04

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'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   12.9049(6)
_cell_length_b                   15.4562(7)
_cell_length_c                   16.6873(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.803(2)
_cell_angle_gamma                90
_cell_volume                     3111.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9897
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      27.83

_exptl_crystal_description       bulk
_exptl_crystal_colour            dark
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_F_000             1576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.821
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3347
_exptl_absorpt_correction_T_max  0.4071
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27313
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.729
_diffrn_reflns_theta_max         28.155
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7556
_reflns_number_gt                5419
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0618P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7556
_refine_ls_number_parameters     532
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1130
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.82039(2) 0.56697(2) 0.69289(2) 0.02608(9) Uani 1 1 d . . . . .
O1 O 0.75891(12) 0.54761(9) 0.56856(9) 0.0286(3) Uani 1 1 d . . . . .
C1 C 0.6370(2) 0.54619(16) 0.42589(14) 0.0361(5) Uani 1 1 d . . . . .
F1 F 0.6803(13) 0.6034(9) 0.3856(10) 0.088(4) Uani 0.5 1 d . . P A 1
F2 F 0.5287(7) 0.5475(8) 0.3831(7) 0.058(2) Uani 0.5 1 d . . P A 1
F3 F 0.6733(10) 0.4688(7) 0.4153(7) 0.090(4) Uani 0.5 1 d . . P A 1
F1A F 0.7063(11) 0.5766(8) 0.3957(8) 0.061(2) Uani 0.5 1 d . . P A 2
F2A F 0.5366(8) 0.5652(8) 0.3751(8) 0.083(4) Uani 0.5 1 d . . P A 2
F3A F 0.6460(9) 0.4613(5) 0.4233(6) 0.0472(18) Uani 0.5 1 d . . P A 2
C2 C 0.66464(18) 0.57254(13) 0.52009(13) 0.0263(5) Uani 1 1 d . . . . .
C3 C 0.58731(18) 0.61990(14) 0.54117(13) 0.0307(5) Uani 1 1 d . . . . .
H3A H 0.5179 0.6324 0.4979 0.037 Uiso 1 1 calc R U . . .
C4 C 0.60820(17) 0.64990(13) 0.62411(14) 0.0276(5) Uani 1 1 d . . . . .
C5 C 0.52075(19) 0.70612(16) 0.64166(14) 0.0343(5) Uani 1 1 d . . . . .
F4 F 0.49572(11) 0.67402(9) 0.70677(8) 0.0460(4) Uani 1 1 d . . . . .
F5 F 0.55944(11) 0.78642(9) 0.66294(9) 0.0471(4) Uani 1 1 d . . . . .
F6 F 0.42656(11) 0.71355(9) 0.57492(9) 0.0448(4) Uani 1 1 d . . . . .
O2 O 0.69319(12) 0.63835(9) 0.68922(9) 0.0298(3) Uani 1 1 d . . . . .
O3 O 0.94982(12) 0.49731(9) 0.69878(9) 0.0289(3) Uani 1 1 d . . . . .
C6 C 1.1163(2) 0.4218(2) 0.75518(18) 0.0538(8) Uani 1 1 d . . . . .
F7 F 1.0585(4) 0.3507(2) 0.7128(3) 0.0464(10) Uani 0.5 1 d . . P B 1
F8 F 1.1779(6) 0.3891(6) 0.8301(3) 0.085(3) Uani 0.5 1 d . . P B 1
F9 F 1.1678(4) 0.4499(3) 0.7170(4) 0.0594(14) Uani 0.5 1 d . . P B 1
F7A F 1.1556(8) 0.3649(6) 0.8117(6) 0.126(4) Uani 0.5 1 d . . P B 2
F8A F 1.2129(5) 0.4695(5) 0.7556(5) 0.108(3) Uani 0.5 1 d . . P B 2
F9A F 1.0937(6) 0.3891(6) 0.6793(4) 0.189(4) Uani 0.5 1 d . . P B 2
C7 C 1.03083(19) 0.48431(15) 0.76638(14) 0.0347(5) Uani 1 1 d . . . . .
C8 C 1.0515(2) 0.51929(16) 0.84755(15) 0.0448(6) Uani 1 1 d . . . . .
H8A H 1.1178 0.5041 0.8930 0.054 Uiso 1 1 calc R U . . .
C9 C 0.9784(2) 0.57507(14) 0.86337(14) 0.0345(5) Uani 1 1 d . . . . .
C10 C 1.0096(2) 0.61573(19) 0.95343(17) 0.0540(7) Uani 1 1 d . . . . .
F10 F 1.02508(14) 0.70075(10) 0.94763(10) 0.0687(5) Uani 1 1 d . . . . .
F11 F 1.10081(16) 0.58373(12) 1.00976(10) 0.0843(6) Uani 1 1 d . . . . .
F12 F 0.92835(16) 0.60599(12) 0.98410(10) 0.0748(5) Uani 1 1 d . . . . .
O4 O 0.88565(13) 0.59970(9) 0.81361(9) 0.0296(3) Uani 1 1 d . . . . .
O1R O 0.57510(12) 0.19185(9) 0.82018(10) 0.0353(4) Uani 1 1 d . . . . .
N2R N 0.58334(14) 0.25383(11) 0.87408(11) 0.0310(4) Uani 1 1 d . . . . .
C3R C 0.5252(2) 0.25121(15) 0.93783(17) 0.0413(6) Uani 1 1 d . . . . .
C4R C 0.4003(2) 0.26360(18) 0.8851(2) 0.0648(9) Uani 1 1 d . . . . .
H4RA H 0.3757 0.3198 0.9006 0.078 Uiso 1 1 calc R U . C 1
H4RB H 0.3897 0.2656 0.8234 0.078 Uiso 1 1 calc R U . C 1
C5R C 0.3281(7) 0.1915(6) 0.9001(6) 0.051(2) Uani 0.5 1 d . . P D 1
H5RA H 0.3030 0.2050 0.9483 0.062 Uiso 0.5 1 calc R U P D 1
H5RB H 0.2630 0.1790 0.8480 0.062 Uiso 0.5 1 calc R U P D 1
C6R C 0.4106(10) 0.1193(8) 0.9215(5) 0.047(2) Uani 0.5 1 d . . P D 1
H6RA H 0.4139 0.0930 0.8684 0.056 Uiso 0.5 1 calc R U P D 1
H6RB H 0.3893 0.0739 0.9546 0.056 Uiso 0.5 1 calc R U P D 1
C5RA C 0.3612(6) 0.1757(7) 0.8845(5) 0.057(2) Uani 0.5 1 d . . P D 2
H5RC H 0.3586 0.1476 0.8305 0.068 Uiso 0.5 1 calc R U P D 2
H5RD H 0.2845 0.1777 0.8844 0.068 Uiso 0.5 1 calc R U P D 2
C6RA C 0.4307(10) 0.1200(9) 0.9591(5) 0.060(3) Uani 0.5 1 d . . P D 2
H6RC H 0.4030 0.1219 1.0073 0.072 Uiso 0.5 1 calc R U P D 2
H6RD H 0.4340 0.0592 0.9416 0.072 Uiso 0.5 1 calc R U P D 2
C7R C 0.5332(2) 0.16151(16) 0.97959(18) 0.0514(7) Uani 1 1 d . . . . .
H7RA H 0.5421 0.1661 1.0409 0.062 Uiso 1 1 calc R U . D 1
H7RB H 0.5951 0.1272 0.9742 0.062 Uiso 1 1 calc R U . D 1
C8R C 0.5827(2) 0.32684(15) 0.99596(17) 0.0483(7) Uani 1 1 d . . . . .
C9R C 0.5130(3) 0.3777(2) 1.0376(3) 0.0897(14) Uani 1 1 d . . . . .
H9RA H 0.4544 0.3409 1.0452 0.108 Uiso 1 1 calc R U . E 1
H9RB H 0.4783 0.4290 1.0029 0.108 Uiso 1 1 calc R U . E 1
C10R C 0.6381(8) 0.3329(7) 1.1437(5) 0.072(2) Uani 0.5 1 d . . P F 1
H10A H 0.5761 0.2937 1.1406 0.086 Uiso 0.5 1 calc R U P F 1
H10B H 0.6957 0.3277 1.2015 0.086 Uiso 0.5 1 calc R U P F 1
C11R C 0.605(2) 0.4067(8) 1.1313(12) 0.119(8) Uani 0.5 1 d . . P F 1
H11A H 0.6613 0.4482 1.1267 0.142 Uiso 0.5 1 calc R U P F 1
H11B H 0.5716 0.4275 1.1727 0.142 Uiso 0.5 1 calc R U P F 1
C10A C 0.578(2) 0.4118(12) 1.1134(13) 0.145(8) Uani 0.5 1 d . . P F 2
H10C H 0.5372 0.4159 1.1532 0.174 Uiso 0.5 1 calc R U P F 2
H10D H 0.6032 0.4705 1.1047 0.174 Uiso 0.5 1 calc R U P F 2
C11A C 0.7051(6) 0.3356(6) 1.1602(5) 0.068(3) Uani 0.5 1 d . . P F 2
H11C H 0.7757 0.3666 1.1891 0.082 Uiso 0.5 1 calc R U P F 2
H11D H 0.6939 0.2894 1.1974 0.082 Uiso 0.5 1 calc R U P F 2
C12R C 0.6904(3) 0.3052(2) 1.07027(18) 0.0722(10) Uani 1 1 d . . . . .
H12A H 0.7537 0.3418 1.0712 0.087 Uiso 1 1 calc R U . F 1
H12B H 0.7105 0.2432 1.0726 0.087 Uiso 1 1 calc R U . F 1
N13R N 0.61396(16) 0.38180(12) 0.93411(12) 0.0359(5) Uani 1 1 d . . . . .
O14R O 0.64508(15) 0.46035(11) 0.94935(11) 0.0482(5) Uani 1 1 d . . . . .
C15R C 0.62160(17) 0.33352(14) 0.86901(13) 0.0273(5) Uani 1 1 d . . . . .
C16R C 0.66460(16) 0.36282(13) 0.80523(12) 0.0243(4) Uani 1 1 d . . . . .
C17R C 0.70707(17) 0.44434(13) 0.79694(13) 0.0265(5) Uani 1 1 d . . . . .
H17A H 0.7117 0.4918 0.8342 0.032 Uiso 1 1 calc R U . . .
N18R N 0.74006(15) 0.44651(11) 0.72997(10) 0.0265(4) Uani 1 1 d . . . . .
N19R N 0.71976(14) 0.36588(11) 0.69562(10) 0.0258(4) Uani 1 1 d . . . . .
C20R C 0.7471(2) 0.34426(15) 0.61929(13) 0.0382(6) Uani 1 1 d . . . . .
H20A H 0.6811 0.3551 0.5674 0.046 Uiso 1 1 calc R U . . .
H20B H 0.8067 0.3834 0.6171 0.046 Uiso 1 1 calc R U . . .
C21R C 0.7828(3) 0.25520(19) 0.61725(19) 0.0738(10) Uani 1 1 d . . . . .
H21A H 0.7994 0.2457 0.5650 0.111 Uiso 1 1 calc R U . . .
H21B H 0.8495 0.2442 0.6676 0.111 Uiso 1 1 calc R U . . .
H21C H 0.7236 0.2158 0.6178 0.111 Uiso 1 1 calc R U . . .
C22R C 0.67396(16) 0.31431(13) 0.73822(12) 0.0254(4) Uani 1 1 d . . . . .
H22A H 0.6521 0.2558 0.7251 0.030 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O4 1.9540(14) . ?
Cu1 O3 1.9600(14) . ?
Cu1 O2 1.9606(14) . ?
Cu1 O1 1.9634(14) . ?
Cu1 N18R 2.3194(17) . ?
Cu1 O1R 2.4085(14) 2_656 ?
O1 C2 1.258(2) . ?
C1 F1A 1.263(12) . ?
C1 F2A 1.305(10) . ?
C1 F3A 1.320(9) . ?
C1 F3 1.320(11) . ?
C1 F2 1.325(9) . ?
C1 F1 1.346(14) . ?
C1 C2 1.538(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.392(3) . ?
C4 O2 1.252(2) . ?
C4 C5 1.533(3) . ?
C5 F6 1.330(2) . ?
C5 F4 1.334(2) . ?
C5 F5 1.338(3) . ?
O3 C7 1.252(3) . ?
C6 F9 1.156(5) . ?
C6 F7A 1.258(8) . ?
C6 F9A 1.296(6) . ?
C6 F8 1.321(7) . ?
C6 F7 1.375(5) . ?
C6 F8A 1.447(7) . ?
C6 C7 1.526(3) . ?
C7 C8 1.393(3) . ?
C8 C9 1.371(3) . ?
C9 O4 1.249(3) . ?
C9 C10 1.544(3) . ?
C10 F11 1.314(3) . ?
C10 F12 1.329(3) . ?
C10 F10 1.338(3) . ?
O1R N2R 1.292(2) . ?
O1R Cu1 2.4086(14) 2_646 ?
N2R C15R 1.341(3) . ?
N2R C3R 1.504(2) . ?
C3R C8R 1.532(4) . ?
C3R C7R 1.539(3) . ?
C3R C4R 1.550(4) . ?
C4R C5RA 1.448(10) . ?
C4R C5R 1.530(9) . ?
C5R C6R 1.495(16) . ?
C6R C7R 1.667(11) . ?
C5RA C6RA 1.518(14) . ?
C6RA C7R 1.399(12) . ?
C8R N13R 1.498(3) . ?
C8R C9R 1.535(3) . ?
C8R C12R 1.535(4) . ?
C9R C10A 1.35(2) . ?
C9R C11R 1.66(2) . ?
C10R C11R 1.210(19) . ?
C10R C12R 1.651(8) . ?
C10A C11A 1.94(2) . ?
C11A C12R 1.519(9) . ?
N13R O14R 1.276(2) . ?
N13R C15R 1.350(3) . ?
C15R C16R 1.437(3) . ?
C16R C22R 1.387(3) . ?
C16R C17R 1.400(3) . ?
C17R N18R 1.330(2) . ?
N18R N19R 1.358(2) . ?
N19R C22R 1.337(2) . ?
N19R C20R 1.476(2) . ?
C20R C21R 1.456(3) . ?

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
O4 Cu1 O3 92.46(6) . . ?
O4 Cu1 O2 86.34(6) . . ?
O3 Cu1 O2 178.65(6) . . ?
O4 Cu1 O1 173.41(6) . . ?
O3 Cu1 O1 89.23(6) . . ?
O2 Cu1 O1 91.89(6) . . ?
O4 Cu1 N18R 90.15(6) . . ?
O3 Cu1 N18R 89.96(6) . . ?
O2 Cu1 N18R 90.66(6) . . ?
O1 Cu1 N18R 96.22(6) . . ?
O4 Cu1 O1R 80.55(6) . 2_656 ?
O3 Cu1 O1R 87.14(5) . 2_656 ?
O2 Cu1 O1R 92.05(5) . 2_656 ?
O1 Cu1 O1R 93.18(6) . 2_656 ?
N18R Cu1 O1R 170.12(6) . 2_656 ?
C2 O1 Cu1 124.61(13) . . ?
F1A C1 F2A 109.7(9) . . ?
F1A C1 F3A 105.8(7) . . ?
F2A C1 F3A 106.4(8) . . ?
F3 C1 F2 107.4(8) . . ?
F3 C1 F1 107.3(8) . . ?
F2 C1 F1 105.5(9) . . ?
F1A C1 C2 111.6(7) . . ?
F2A C1 C2 114.9(5) . . ?
F3A C1 C2 107.8(5) . . ?
F3 C1 C2 114.4(5) . . ?
F2 C1 C2 111.4(5) . . ?
F1 C1 C2 110.5(7) . . ?
O1 C2 C3 128.33(19) . . ?
O1 C2 C1 113.35(18) . . ?
C3 C2 C1 118.3(2) . . ?
O1 C2 Cu1 34.24(9) . . ?
C3 C2 Cu1 94.11(13) . . ?
C1 C2 Cu1 147.57(15) . . ?
C2 C3 C4 121.9(2) . . ?
O2 C4 C3 128.00(19) . . ?
O2 C4 C5 113.10(18) . . ?
C3 C4 C5 118.88(19) . . ?
O2 C4 Cu1 34.08(9) . . ?
C3 C4 Cu1 93.98(13) . . ?
C5 C4 Cu1 147.14(15) . . ?
F6 C5 F4 107.48(18) . . ?
F6 C5 F5 106.62(19) . . ?
F4 C5 F5 107.71(18) . . ?
F6 C5 C4 113.89(18) . . ?
F4 C5 C4 110.63(18) . . ?
F5 C5 C4 110.24(17) . . ?
C4 O2 Cu1 124.95(13) . . ?
C7 O3 Cu1 123.87(13) . . ?
F7A C6 F9A 110.5(6) . . ?
F9 C6 F8 113.2(5) . . ?
F9 C6 F7 109.3(4) . . ?
F8 C6 F7 102.4(5) . . ?
F7A C6 F8A 103.6(6) . . ?
F9A C6 F8A 95.6(6) . . ?
F9 C6 C7 114.3(4) . . ?
F7A C6 C7 117.9(4) . . ?
F9A C6 C7 116.4(3) . . ?
F8 C6 C7 110.1(4) . . ?
F7 C6 C7 106.6(3) . . ?
F8A C6 C7 109.6(3) . . ?
O3 C7 C8 128.6(2) . . ?
O3 C7 C6 113.54(19) . . ?
C8 C7 C6 117.9(2) . . ?
O3 C7 Cu1 34.77(9) . . ?
C8 C7 Cu1 93.92(15) . . ?
C6 C7 Cu1 148.11(16) . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 Cu1 60.78(13) . . ?
C7 C8 Cu1 60.84(13) . . ?
O4 C9 C8 128.7(2) . . ?
O4 C9 C10 112.4(2) . . ?
C8 C9 C10 118.9(2) . . ?
O4 C9 Cu1 34.34(9) . . ?
C8 C9 Cu1 94.43(14) . . ?
C10 C9 Cu1 146.62(17) . . ?
F11 C10 F12 108.1(2) . . ?
F11 C10 F10 107.6(2) . . ?
F12 C10 F10 107.3(2) . . ?
F11 C10 C9 113.6(2) . . ?
F12 C10 C9 111.1(2) . . ?
F10 C10 C9 108.9(2) . . ?
C9 O4 Cu1 124.53(14) . . ?
N2R O1R Cu1 138.31(13) . 2_646 ?
O1R N2R C15R 125.33(17) . . ?
O1R N2R C3R 122.26(17) . . ?
C15R N2R C3R 110.89(17) . . ?
N2R C3R C8R 100.15(17) . . ?
N2R C3R C7R 112.02(18) . . ?
C8R C3R C7R 117.5(2) . . ?
N2R C3R C4R 105.9(2) . . ?
C8R C3R C4R 115.9(2) . . ?
C7R C3R C4R 104.9(2) . . ?
C5RA C4R C3R 100.3(4) . . ?
C5R C4R C3R 112.9(4) . . ?
C6R C5R C4R 99.2(6) . . ?
C5R C6R C7R 107.1(8) . . ?
C4R C5RA C6RA 115.0(7) . . ?
C7R C6RA C5RA 99.9(8) . . ?
C6RA C7R C3R 113.4(6) . . ?
C3R C7R C6R 101.1(5) . . ?
N13R C8R C3R 100.65(18) . . ?
N13R C8R C9R 111.5(2) . . ?
C3R C8R C9R 116.6(2) . . ?
N13R C8R C12R 107.0(2) . . ?
C3R C8R C12R 116.2(2) . . ?
C9R C8R C12R 104.7(3) . . ?
C10A C9R C8R 110.6(9) . . ?
C8R C9R C11R 103.1(7) . . ?
C11R C10R C12R 109.3(9) . . ?
C10R C11R C9R 89.8(9) . . ?
C9R C10A C11A 107.3(10) . . ?
C12R C11A C10A 89.9(7) . . ?
C11A C12R C8R 119.4(4) . . ?
C8R C12R C10R 93.0(4) . . ?
O14R N13R C15R 125.36(17) . . ?
O14R N13R C8R 123.01(18) . . ?
C15R N13R C8R 110.81(18) . . ?
N2R C15R N13R 108.86(17) . . ?
N2R C15R C16R 125.72(18) . . ?
N13R C15R C16R 125.42(19) . . ?
C22R C16R C17R 104.92(17) . . ?
C22R C16R C15R 126.44(19) . . ?
C17R C16R C15R 128.63(18) . . ?
N18R C17R C16R 111.04(18) . . ?
N18R C17R Cu1 36.57(9) . . ?
C16R C17R Cu1 147.59(14) . . ?
C17R N18R N19R 105.08(16) . . ?
C17R N18R Cu1 123.44(13) . . ?
N19R N18R Cu1 131.43(12) . . ?
C22R N19R N18R 112.22(15) . . ?
C22R N19R C20R 127.60(18) . . ?
N18R N19R C20R 120.18(16) . . ?
C21R C20R N19R 114.15(19) . . ?
N19R C22R C16R 106.73(18) . . ?

_refine_diff_density_max         0.441
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.062

_shelxl_version_number           2014/6



_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_83
_database_code_depnum_ccdc_archive 'CCDC 1476198'
_audit_update_record             
;
2016-04-24 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 Cu F12 N4 O6'
_chemical_formula_weight         781.04

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'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   11.4229(9)
_cell_length_b                   11.4410(9)
_cell_length_c                   14.0936(11)
_cell_angle_alpha                105.066(5)
_cell_angle_beta                 95.834(5)
_cell_angle_gamma                109.950(6)
_cell_volume                     1634.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3494
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      19.30

_exptl_crystal_description       bulk
_exptl_crystal_colour            dark
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_F_000             788
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.781
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26753
_diffrn_reflns_av_unetI/netI     0.1110
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.940
_diffrn_reflns_theta_max         28.008
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7807
_reflns_number_gt                2827
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0868P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0035(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7807
_refine_ls_number_parameters     546
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1822
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1855
_refine_ls_wR_factor_gt          0.1385
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_restrained_S_all      0.920
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.0000 0.0000 0.0705(3) Uani 1 2 d S . P . .
O1 O 0.4492(3) 0.3526(3) 0.3766(2) 0.0673(8) Uani 1 1 d . . . . .
C1 C 0.4119(9) 0.1440(7) 0.2680(5) 0.0963(18) Uani 1 1 d . . . . .
F1 F 0.5146(16) 0.1974(18) 0.2209(12) 0.180(7) Uani 0.5 1 d . . P A 1
F2 F 0.312(2) 0.128(2) 0.2152(12) 0.198(12) Uani 0.5 1 d . . P A 1
F3 F 0.425(2) 0.0373(15) 0.2655(13) 0.121(7) Uani 0.5 1 d . . P A 1
F1A F 0.468(3) 0.068(2) 0.2592(18) 0.196(12) Uani 0.5 1 d . . P A 2
F2A F 0.4262(17) 0.1937(11) 0.2013(9) 0.113(4) Uani 0.5 1 d . . P A 2
F3A F 0.2856(16) 0.0663(16) 0.2472(12) 0.165(9) Uani 0.5 1 d . . P A 2
C2 C 0.4411(4) 0.2397(5) 0.3744(3) 0.0703(12) Uani 1 1 d . . . . .
C3 C 0.4533(5) 0.1937(5) 0.4538(4) 0.0857(14) Uani 1 1 d . . . . .
H3A H 0.4455 0.1071 0.4408 0.103 Uiso 1 1 calc R U . . .
C4 C 0.4764(4) 0.2698(5) 0.5515(4) 0.0727(12) Uani 1 1 d . . . . .
C5 C 0.4872(11) 0.2106(7) 0.6365(6) 0.113(2) Uani 1 1 d . . . . .
F6 F 0.4612(10) 0.0881(5) 0.6053(3) 0.221(3) Uani 1 1 d . . . . .
F4 F 0.607(2) 0.229(3) 0.662(2) 0.208(12) Uani 0.5 1 d . . P B 1
F5 F 0.4572(19) 0.2604(12) 0.7129(8) 0.123(5) Uani 0.5 1 d . . P B 1
F4A F 0.595(3) 0.280(2) 0.7006(13) 0.188(13) Uani 0.5 1 d . . P B 2
F5A F 0.385(2) 0.198(2) 0.675(2) 0.262(12) Uani 0.5 1 d . . P B 2
O2 O 0.4919(3) 0.3879(3) 0.5834(2) 0.0693(8) Uani 1 1 d . . . . .
Cu2 Cu 0.5000 0.5000 0.5000 0.0633(3) Uani 1 2 d S . P . .
O3 O 0.1538(3) 0.0623(3) -0.0495(2) 0.0741(8) Uani 1 1 d . . . . .
C6 C 0.3466(9) 0.0773(10) -0.0990(9) 0.112(3) Uani 1 1 d . . . . .
F7 F 0.412(3) 0.191(2) -0.044(2) 0.202(10) Uani 0.5 1 d . . P C 1
F8 F 0.418(3) 0.020(3) -0.116(3) 0.229(14) Uani 0.5 1 d . . P C 1
F9 F 0.302(2) 0.085(4) -0.178(2) 0.223(13) Uani 0.5 1 d . . P C 1
F7A F 0.359(2) 0.202(2) -0.100(2) 0.156(8) Uani 0.5 1 d . . P C 2
F8A F 0.4502(12) 0.068(3) -0.068(2) 0.193(13) Uani 0.5 1 d . . P C 2
F9A F 0.3136(18) 0.0144(18) -0.2015(10) 0.129(6) Uani 0.5 1 d . . P C 2
C7 C 0.2372(4) 0.0134(5) -0.0525(3) 0.0730(13) Uani 1 1 d . . . . .
C8 C 0.2419(5) -0.0851(5) -0.0178(4) 0.0801(14) Uani 1 1 d . . . . .
H8A H 0.3083 -0.1134 -0.0272 0.096 Uiso 1 1 calc R U . . .
C9 C 0.1519(5) -0.1452(4) 0.0311(3) 0.0735(13) Uani 1 1 d . . . . .
C10 C 0.1639(8) -0.2582(7) 0.0651(6) 0.0994(18) Uani 1 1 d . . . . .
F10 F 0.118(4) -0.272(3) 0.1382(15) 0.195(12) Uani 0.56(3) 1 d . . P D 1
F11 F 0.2814(11) -0.2589(18) 0.073(3) 0.176(10) Uani 0.56(3) 1 d . . P D 1
F12 F 0.102(2) -0.3636(12) -0.0090(15) 0.134(7) Uani 0.56(3) 1 d . . P D 1
F10A F 0.062(2) -0.326(3) 0.088(4) 0.25(2) Uani 0.44(3) 1 d . . P D 2
F11A F 0.247(3) -0.2210(14) 0.1414(17) 0.162(12) Uani 0.44(3) 1 d . . P D 2
F12A F 0.185(6) -0.344(4) -0.001(2) 0.200(17) Uani 0.44(3) 1 d . . P D 2
O4 O 0.0577(3) -0.1185(3) 0.0526(2) 0.0727(8) Uani 1 1 d . . . . .
O1R O 0.2905(3) 0.5023(3) 0.5030(2) 0.0765(9) Uani 1 1 d . . . . .
N2R N 0.1901(4) 0.4108(4) 0.5104(2) 0.0632(9) Uani 1 1 d . . . . .
C3R C 0.1440(4) 0.4187(4) 0.6065(3) 0.0677(12) Uani 1 1 d . . . . .
C4R C 0.2515(5) 0.4602(6) 0.6957(3) 0.0964(17) Uani 1 1 d . . . . .
H4RA H 0.2471 0.3859 0.7184 0.116 Uiso 1 1 calc R U . . .
H4RB H 0.3330 0.4933 0.6771 0.116 Uiso 1 1 calc R U . . .
C5R C 0.2387(10) 0.5585(13) 0.7727(6) 0.343(10) Uani 1 1 d . . . . .
H5RA H 0.3191 0.6334 0.7956 0.411 Uiso 1 1 calc R U . . .
H5RB H 0.2207 0.5261 0.8289 0.411 Uiso 1 1 calc R U . . .
C6R C 0.1403(7) 0.6008(7) 0.7429(5) 0.150(3) Uani 1 1 d . . . . .
H6RA H 0.1725 0.6954 0.7597 0.180 Uiso 1 1 calc R U . . .
H6RB H 0.0694 0.5726 0.7752 0.180 Uiso 1 1 calc R U . . .
C7R C 0.1003(6) 0.5358(5) 0.6301(4) 0.0959(16) Uani 1 1 d . . . . .
H7RA H 0.1404 0.5971 0.5957 0.115 Uiso 1 1 calc R U . . .
H7RB H 0.0086 0.5051 0.6087 0.115 Uiso 1 1 calc R U . . .
C8R C 0.0371(5) 0.2826(5) 0.5795(3) 0.0848(15) Uani 1 1 d . . . . .
C9R C -0.0937(6) 0.2763(7) 0.6105(4) 0.143(3) Uani 1 1 d . . . . .
H9RA H -0.0798 0.3412 0.6749 0.172 Uiso 1 1 calc R U . . .
H9RB H -0.1476 0.2901 0.5603 0.172 Uiso 1 1 calc R U . . .
C10R C -0.1518(13) 0.1388(10) 0.6165(8) 0.290(9) Uani 1 1 d . . . . .
H10A H -0.1957 0.0759 0.5507 0.348 Uiso 1 1 calc R U . . .
H10B H -0.2109 0.1333 0.6615 0.348 Uiso 1 1 calc R U . . .
C11R C -0.0258(19) 0.1149(14) 0.6611(11) 0.326(12) Uani 1 1 d . . . . .
H11A H -0.0016 0.1528 0.7337 0.391 Uiso 1 1 calc R U . . .
H11B H -0.0421 0.0222 0.6432 0.391 Uiso 1 1 calc R U . . .
C12R C 0.0723(10) 0.1806(6) 0.6142(6) 0.190(4) Uani 1 1 d . . . . .
H12A H 0.0805 0.1172 0.5571 0.228 Uiso 1 1 calc R U . . .
H12B H 0.1534 0.2231 0.6618 0.228 Uiso 1 1 calc R U . . .
N13R N 0.0151(4) 0.2388(4) 0.4679(3) 0.0828(12) Uani 1 1 d . . . . .
C14R C 0.1086(4) 0.3109(4) 0.4331(3) 0.0612(11) Uani 1 1 d . . . . .
O14R O -0.0803(4) 0.1369(4) 0.4136(3) 0.1276(16) Uani 1 1 d . . . . .
C16R C 0.1180(4) 0.2868(4) 0.3292(3) 0.0617(11) Uani 1 1 d . . . . .
C17R C 0.0477(4) 0.1753(4) 0.2470(3) 0.0698(12) Uani 1 1 d . . . . .
H17A H -0.0149 0.1008 0.2517 0.084 Uiso 1 1 calc R U . . .
N18R N 0.0805(4) 0.1884(4) 0.1619(3) 0.0728(10) Uani 1 1 d . . . . .
N19R N 0.1734(4) 0.3092(4) 0.1898(3) 0.0770(11) Uani 1 1 d . . . . .
C20R C 0.2277(7) 0.3622(7) 0.1112(4) 0.143(3) Uani 1 1 d D . . . .
H20A H 0.2142 0.2884 0.0526 0.172 Uiso 1 1 calc R U . . .
H20B H 0.1788 0.4100 0.0920 0.172 Uiso 1 1 calc R U . . .
C21R C 0.3424(12) 0.4352(12) 0.1316(8) 0.371(12) Uani 1 1 d D . . . .
H21A H 0.3645 0.4620 0.0746 0.445 Uiso 1 1 calc R U . . .
H21B H 0.3578 0.5111 0.1878 0.445 Uiso 1 1 calc R U . . .
H21G H 0.3933 0.3889 0.1483 0.445 Uiso 1 1 calc R U . . .
C22R C 0.1983(4) 0.3705(4) 0.2885(3) 0.0699(12) Uani 1 1 d . . . . .
H22A H 0.2585 0.4541 0.3230 0.084 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O3 1.933(3) 2 ?
Cu1 O3 1.933(3) . ?
Cu1 O4 1.963(3) . ?
Cu1 O4 1.963(3) 2 ?
Cu1 N18R 2.523(4) 2 ?
Cu1 N18R 2.523(4) . ?
O1 C2 1.255(5) . ?
O1 Cu2 1.951(3) . ?
C1 F2A 1.217(12) . ?
C1 F2 1.224(14) . ?
C1 F1A 1.23(2) . ?
C1 F3 1.27(2) . ?
C1 F3A 1.365(17) . ?
C1 F1 1.439(16) . ?
C1 C2 1.534(7) . ?
C2 C3 1.369(6) . ?
C2 Cu2 2.847(4) . ?
C3 C4 1.367(6) . ?
C3 Cu2 3.234(5) . ?
C4 O2 1.250(5) . ?
C4 C5 1.536(7) . ?
C4 Cu2 2.843(5) . ?
C5 F5 1.221(16) . ?
C5 F6 1.271(7) . ?
C5 F4 1.30(3) . ?
C5 F4A 1.31(3) . ?
C5 F5A 1.32(2) . ?
O2 Cu2 1.939(3) . ?
Cu2 O2 1.939(3) 2_666 ?
Cu2 O1 1.951(3) 2_666 ?
Cu2 O1R 2.406(3) 2_666 ?
Cu2 O1R 2.406(3) . ?
O3 C7 1.258(5) . ?
C6 F8 1.212(19) . ?
C6 F9 1.22(2) . ?
C6 F7 1.24(2) . ?
C6 F8A 1.264(18) . ?
C6 F9A 1.38(2) . ?
C6 F7A 1.39(2) . ?
C6 C7 1.522(8) . ?
C7 C8 1.355(7) . ?
C8 C9 1.382(7) . ?
C9 O4 1.259(5) . ?
C9 C10 1.533(7) . ?
C10 F10 1.227(14) . ?
C10 F11A 1.231(14) . ?
C10 F12A 1.275(19) . ?
C10 F10A 1.28(2) . ?
C10 F12 1.288(16) . ?
C10 F11 1.339(13) . ?
O1R N2R 1.298(4) . ?
N2R C14R 1.334(5) . ?
N2R C3R 1.495(5) . ?
C3R C4R 1.514(6) . ?
C3R C8R 1.536(6) . ?
C3R C7R 1.554(6) . ?
C4R C5R 1.405(8) . ?
C5R C6R 1.433(10) . ?
C6R C7R 1.514(7) . ?
C8R N13R 1.487(5) . ?
C8R C12R 1.530(8) . ?
C8R C9R 1.583(7) . ?
C9R C10R 1.514(11) . ?
C10R C11R 1.648(19) . ?
C11R C12R 1.446(14) . ?
N13R O14R 1.277(4) . ?
N13R C14R 1.333(5) . ?
C14R C16R 1.441(5) . ?
C16R C22R 1.371(6) . ?
C16R C17R 1.399(5) . ?
C17R N18R 1.321(5) . ?
N18R N19R 1.350(5) . ?
N19R C22R 1.335(5) . ?
N19R C20R 1.488(6) . ?
C20R C21R 1.244(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Cu1 O3 180.0 2 . ?
O3 Cu1 O4 87.83(13) 2 . ?
O3 Cu1 O4 92.17(13) . . ?
O3 Cu1 O4 92.17(13) 2 2 ?
O3 Cu1 O4 87.84(13) . 2 ?
O4 Cu1 O4 180.0 . 2 ?
O3 Cu1 N18R 93.88(12) 2 2 ?
O3 Cu1 N18R 86.12(12) . 2 ?
O4 Cu1 N18R 84.01(12) . 2 ?
O4 Cu1 N18R 95.99(12) 2 2 ?
O3 Cu1 N18R 86.12(12) 2 . ?
O3 Cu1 N18R 93.88(12) . . ?
O4 Cu1 N18R 95.99(12) . . ?
O4 Cu1 N18R 84.01(12) 2 . ?
N18R Cu1 N18R 180.0 2 . ?
C2 O1 Cu2 123.8(3) . . ?
F2A C1 F1A 108.6(16) . . ?
F2 C1 F3 113.5(15) . . ?
F2A C1 F3A 105.4(12) . . ?
F1A C1 F3A 105.3(16) . . ?
F2 C1 F1 107.9(16) . . ?
F3 C1 F1 98.7(15) . . ?
F2A C1 C2 115.6(7) . . ?
F2 C1 C2 114.1(8) . . ?
F1A C1 C2 114.6(12) . . ?
F3 C1 C2 114.0(9) . . ?
F3A C1 C2 106.5(9) . . ?
F1 C1 C2 107.1(8) . . ?
O1 C2 C3 128.1(4) . . ?
O1 C2 C1 114.1(5) . . ?
C3 C2 C1 117.9(5) . . ?
O1 C2 Cu2 34.71(18) . . ?
C3 C2 Cu2 93.5(3) . . ?
C1 C2 Cu2 148.5(4) . . ?
C4 C3 C2 122.7(4) . . ?
C4 C3 Cu2 61.3(3) . . ?
C2 C3 Cu2 61.5(3) . . ?
O2 C4 C3 127.7(4) . . ?
O2 C4 C5 112.7(5) . . ?
C3 C4 C5 119.6(5) . . ?
O2 C4 Cu2 34.09(19) . . ?
C3 C4 Cu2 93.7(3) . . ?
C5 C4 Cu2 146.5(4) . . ?
F5 C5 F6 121.1(10) . . ?
F5 C5 F4 106.5(15) . . ?
F6 C5 F4 88.6(14) . . ?
F6 C5 F4A 115.0(12) . . ?
F6 C5 F5A 94.0(13) . . ?
F4A C5 F5A 114.9(17) . . ?
F5 C5 C4 115.2(9) . . ?
F6 C5 C4 113.5(6) . . ?
F4 C5 C4 106.9(13) . . ?
F4A C5 C4 110.5(14) . . ?
F5A C5 C4 107.9(11) . . ?
C4 O2 Cu2 124.7(3) . . ?
O2 Cu2 O2 180.00(19) 2_666 . ?
O2 Cu2 O1 87.80(12) 2_666 . ?
O2 Cu2 O1 92.20(12) . . ?
O2 Cu2 O1 92.20(12) 2_666 2_666 ?
O2 Cu2 O1 87.80(12) . 2_666 ?
O1 Cu2 O1 180.0 . 2_666 ?
O2 Cu2 O1R 96.36(12) 2_666 2_666 ?
O2 Cu2 O1R 83.64(12) . 2_666 ?
O1 Cu2 O1R 84.00(11) . 2_666 ?
O1 Cu2 O1R 96.00(11) 2_666 2_666 ?
O2 Cu2 O1R 83.64(12) 2_666 . ?
O2 Cu2 O1R 96.36(12) . . ?
O1 Cu2 O1R 96.00(11) . . ?
O1 Cu2 O1R 84.00(11) 2_666 . ?
O1R Cu2 O1R 180.0 2_666 . ?
C7 O3 Cu1 124.8(3) . . ?
F8 C6 F9 107.6(19) . . ?
F8 C6 F7 108(2) . . ?
F9 C6 F7 106.8(19) . . ?
F8A C6 F9A 106.1(14) . . ?
F8A C6 F7A 114.3(17) . . ?
F9A C6 F7A 98.5(18) . . ?
F8 C6 C7 115.7(14) . . ?
F9 C6 C7 108.2(13) . . ?
F7 C6 C7 110.5(11) . . ?
F8A C6 C7 114.4(13) . . ?
F9A C6 C7 108.3(10) . . ?
F7A C6 C7 113.5(10) . . ?
O3 C7 C8 128.0(5) . . ?
O3 C7 C6 114.4(6) . . ?
C8 C7 C6 117.6(6) . . ?
O3 C7 Cu1 33.9(2) . . ?
C8 C7 Cu1 94.2(3) . . ?
C6 C7 Cu1 148.3(5) . . ?
C7 C8 C9 122.7(5) . . ?
C7 C8 Cu1 61.2(3) . . ?
C9 C8 Cu1 61.7(3) . . ?
O4 C9 C8 127.7(5) . . ?
O4 C9 C10 113.7(5) . . ?
C8 C9 C10 118.6(5) . . ?
O4 C9 Cu1 35.1(2) . . ?
C8 C9 Cu1 93.1(3) . . ?
C10 C9 Cu1 147.8(5) . . ?
F11A C10 F12A 107.2(15) . . ?
F11A C10 F10A 104.0(18) . . ?
F12A C10 F10A 102.9(19) . . ?
F10 C10 F12 107.2(16) . . ?
F10 C10 F11 113.4(14) . . ?
F12 C10 F11 100.6(12) . . ?
F10 C10 C9 114.5(8) . . ?
F11A C10 C9 113.1(9) . . ?
F12A C10 C9 115.1(11) . . ?
F10A C10 C9 113.4(12) . . ?
F12 C10 C9 106.4(9) . . ?
F11 C10 C9 113.3(8) . . ?
C9 O4 Cu1 123.3(3) . . ?
N2R O1R Cu2 127.9(2) . . ?
O1R N2R C14R 124.8(3) . . ?
O1R N2R C3R 122.0(3) . . ?
C14R N2R C3R 112.6(4) . . ?
N2R C3R C4R 112.0(4) . . ?
N2R C3R C8R 101.3(3) . . ?
C4R C3R C8R 118.5(4) . . ?
N2R C3R C7R 107.5(4) . . ?
C4R C3R C7R 102.2(4) . . ?
C8R C3R C7R 115.3(4) . . ?
C5R C4R C3R 107.9(5) . . ?
C4R C5R C6R 113.8(6) . . ?
C5R C6R C7R 104.1(5) . . ?
C6R C7R C3R 106.4(5) . . ?
N13R C8R C12R 106.7(4) . . ?
N13R C8R C3R 101.5(4) . . ?
C12R C8R C3R 115.9(5) . . ?
N13R C8R C9R 108.2(4) . . ?
C12R C8R C9R 106.5(6) . . ?
C3R C8R C9R 117.2(4) . . ?
C10R C9R C8R 103.2(8) . . ?
C9R C10R C11R 102.3(9) . . ?
C12R C11R C10R 104.2(9) . . ?
C11R C12R C8R 109.3(9) . . ?
O14R N13R C14R 124.9(4) . . ?
O14R N13R C8R 122.0(4) . . ?
C14R N13R C8R 113.0(4) . . ?
N2R C14R N13R 108.5(4) . . ?
N2R C14R C16R 125.8(4) . . ?
N13R C14R C16R 125.6(4) . . ?
C22R C16R C17R 104.3(4) . . ?
C22R C16R C14R 127.1(4) . . ?
C17R C16R C14R 128.6(4) . . ?
N18R C17R C16R 112.0(4) . . ?
C17R N18R N19R 104.0(3) . . ?
C17R N18R Cu1 122.3(3) . . ?
N19R N18R Cu1 132.8(3) . . ?
C22R N19R N18R 112.8(4) . . ?
C22R N19R C20R 127.9(4) . . ?
N18R N19R C20R 119.2(4) . . ?
C21R C20R N19R 118.3(8) . . ?
N19R C22R C16R 106.9(4) . . ?

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.055

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_87b-110
_database_code_depnum_ccdc_archive 'CCDC 1476199'
_audit_update_record             
;
2016-04-24 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 Cu F12 N4 O6'
_chemical_formula_weight         781.04

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'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   13.481(2)
_cell_length_b                   14.380(2)
_cell_length_c                   16.521(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.680(7)
_cell_angle_gamma                90
_cell_volume                     2976.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    2338
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      22.71

_exptl_crystal_description       bulk
_exptl_crystal_colour            dark
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_F_000             1576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.858
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15246
_diffrn_reflns_av_unetI/netI     0.1339
_diffrn_reflns_av_R_equivalents  0.0910
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.676
_diffrn_reflns_theta_max         27.194
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             5608
_reflns_number_gt                3007
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0892P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5608
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.0680
_refine_ls_wR_factor_ref         0.1989
_refine_ls_wR_factor_gt          0.1558
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.82819(6) 0.54458(5) 0.69781(5) 0.0232(2) Uani 1 1 d . . . . .
O1 O 0.7590(3) 0.5523(3) 0.5539(3) 0.0298(10) Uani 1 1 d . . . . .
C1 C 0.6243(5) 0.5619(5) 0.4135(4) 0.0331(17) Uani 1 1 d . . . . .
F1 F 0.649(3) 0.638(2) 0.3769(13) 0.053(7) Uani 0.5 1 d . . P A 1
F2 F 0.518(2) 0.5454(17) 0.3759(18) 0.034(5) Uani 0.5 1 d . . P A 1
F3 F 0.667(2) 0.487(2) 0.3925(13) 0.071(9) Uani 0.5 1 d . . P A 1
F1A F 0.672(3) 0.618(2) 0.3775(19) 0.079(12) Uani 0.5 1 d . . P A 2
F2A F 0.525(3) 0.5738(17) 0.374(2) 0.045(7) Uani 0.5 1 d . . P A 2
F3A F 0.655(3) 0.4803(18) 0.3959(19) 0.076(10) Uani 0.5 1 d . . P A 2
C2 C 0.6644(5) 0.5756(4) 0.5132(4) 0.0281(15) Uani 1 1 d . . . . .
C3 C 0.5920(5) 0.6161(4) 0.5456(4) 0.0285(15) Uani 1 1 d . . . . .
H3A H 0.5213 0.6282 0.5064 0.034 Uiso 1 1 calc R U . . .
C4 C 0.6200(5) 0.6393(4) 0.6335(4) 0.0278(15) Uani 1 1 d . . . . .
C5 C 0.5389(5) 0.6898(4) 0.6612(4) 0.0321(16) Uani 1 1 d . . . . .
F4 F 0.5233(3) 0.6468(3) 0.7266(2) 0.0454(10) Uani 1 1 d . . . . .
F5 F 0.5730(3) 0.7765(3) 0.6885(3) 0.0467(11) Uani 1 1 d . . . . .
F6 F 0.4429(3) 0.6998(3) 0.5975(2) 0.0422(10) Uani 1 1 d . . . . .
O2 O 0.7073(3) 0.6249(3) 0.6958(3) 0.0297(11) Uani 1 1 d . . . . .
O3 O 0.9511(3) 0.4641(3) 0.7057(3) 0.0278(10) Uani 1 1 d . . . . .
C6 C 1.1262(5) 0.4089(5) 0.7458(4) 0.0323(16) Uani 1 1 d . . . . .
F8 F 1.2226(3) 0.4122(3) 0.8052(3) 0.0688(15) Uani 1 1 d . . . . .
F7 F 1.0997(4) 0.3189(3) 0.7336(3) 0.0627(13) Uani 1 1 d . . . . .
F9 F 1.1329(3) 0.4373(3) 0.6723(3) 0.0597(13) Uani 1 1 d . . . . .
C7 C 1.0417(5) 0.4637(4) 0.7676(4) 0.0262(15) Uani 1 1 d . . . . .
C8 C 1.0734(5) 0.5057(4) 0.8485(4) 0.0283(15) Uani 1 1 d . . . . .
H8A H 1.1462 0.5008 0.8861 0.034 Uiso 1 1 calc R U . . .
C9 C 1.0029(5) 0.5555(4) 0.8779(4) 0.0241(14) Uani 1 1 d . . . . .
C10 C 1.0555(6) 0.6109(5) 0.9630(5) 0.0404(18) Uani 1 1 d . . . . .
F10 F 1.0631(4) 0.6999(3) 0.9433(3) 0.0583(12) Uani 1 1 d . . . . .
F11 F 1.1525(3) 0.5818(3) 1.0124(2) 0.0520(12) Uani 1 1 d . . . . .
F12 F 0.9959(3) 0.6077(3) 1.0123(2) 0.0471(11) Uani 1 1 d . . . . .
O4 O 0.9053(3) 0.5628(3) 0.8439(3) 0.0264(10) Uani 1 1 d . . . . .
O1R O 0.5763(3) 0.1550(3) 0.7879(3) 0.0266(10) Uani 1 1 d . . . . .
N2R N 0.5808(4) 0.2199(3) 0.8446(3) 0.0237(12) Uani 1 1 d . . . . .
C3R C 0.5113(5) 0.2158(4) 0.8982(4) 0.0232(14) Uani 1 1 d . . . . .
C4R C 0.3943(5) 0.2243(4) 0.8351(4) 0.0286(15) Uani 1 1 d . . . . .
H4RA H 0.3846 0.1969 0.7777 0.034 Uiso 1 1 calc R U . . .
H4RB H 0.3716 0.2902 0.8268 0.034 Uiso 1 1 calc R U . . .
C5R C 0.3300(5) 0.1692(5) 0.8800(4) 0.0341(16) Uani 1 1 d . . . . .
H5RA H 0.2819 0.2114 0.8957 0.041 Uiso 1 1 calc R U . . .
H5RB H 0.2865 0.1203 0.8406 0.041 Uiso 1 1 calc R U . . .
C6R C 0.4122(5) 0.1256(4) 0.9619(4) 0.0285(15) Uani 1 1 d . . . . .
H6RA H 0.3898 0.0625 0.9720 0.034 Uiso 1 1 calc R U . . .
H6RB H 0.4224 0.1645 1.0138 0.034 Uiso 1 1 calc R U . . .
C7R C 0.5153(5) 0.1219(4) 0.9416(4) 0.0268(15) Uani 1 1 d . . . . .
H7RA H 0.5796 0.1160 0.9955 0.032 Uiso 1 1 calc R U . . .
H7RB H 0.5136 0.0700 0.9017 0.032 Uiso 1 1 calc R U . . .
C8R C 0.5555(5) 0.3011(4) 0.9590(4) 0.0238(14) Uani 1 1 d . . . . .
C9R C 0.4759(5) 0.3585(4) 0.9863(4) 0.0273(15) Uani 1 1 d . . . . .
H9RA H 0.4652 0.4208 0.9589 0.033 Uiso 1 1 calc R U . . .
H9RB H 0.4060 0.3266 0.9681 0.033 Uiso 1 1 calc R U . . .
C10A C 0.5247(5) 0.3670(5) 1.0849(4) 0.0364(17) Uani 1 1 d . . . . .
H10C H 0.5054 0.4271 1.1044 0.044 Uiso 1 1 calc R U . . .
H10D H 0.5005 0.3157 1.1132 0.044 Uiso 1 1 calc R U . . .
C11A C 0.6434(5) 0.3612(5) 1.1058(4) 0.0361(17) Uani 1 1 d . . . . .
H11C H 0.6824 0.3452 1.1678 0.043 Uiso 1 1 calc R U . . .
H11D H 0.6716 0.4205 1.0926 0.043 Uiso 1 1 calc R U . . .
C12R C 0.6515(5) 0.2837(4) 1.0462(4) 0.0283(15) Uani 1 1 d . . . . .
H12A H 0.6457 0.2221 1.0708 0.034 Uiso 1 1 calc R U . . .
H12B H 0.7201 0.2871 1.0373 0.034 Uiso 1 1 calc R U . . .
N13R N 0.5978(4) 0.3581(3) 0.9026(3) 0.0256(12) Uani 1 1 d . . . . .
O14R O 0.6205(3) 0.4446(3) 0.9158(3) 0.0304(11) Uani 1 1 d . . . . .
C15R C 0.6178(5) 0.3061(4) 0.8419(4) 0.0220(14) Uani 1 1 d . . . . .
C16R C 0.6649(4) 0.3402(4) 0.7829(4) 0.0243(14) Uani 1 1 d . . . . .
C17R C 0.7097(4) 0.4275(4) 0.7803(4) 0.0251(15) Uani 1 1 d . . . . .
H17A H 0.7146 0.4763 0.8204 0.030 Uiso 1 1 calc R U . . .
N18R N 0.7444(4) 0.4336(3) 0.7149(3) 0.0267(12) Uani 1 1 d . . . . .
N19R N 0.7235(4) 0.3480(3) 0.6750(3) 0.0241(12) Uani 1 1 d . . . . .
C20R C 0.7562(5) 0.3280(4) 0.6004(4) 0.0312(16) Uani 1 1 d . . . . .
H20A H 0.8303 0.3500 0.6144 0.037 Uiso 1 1 calc R U . . .
H20B H 0.7093 0.3628 0.5487 0.037 Uiso 1 1 calc R U . . .
C21R C 0.7501(5) 0.2260(4) 0.5792(4) 0.0321(16) Uani 1 1 d . . . . .
H21A H 0.7723 0.2159 0.5297 0.048 Uiso 1 1 calc R U . . .
H21B H 0.7974 0.1915 0.6298 0.048 Uiso 1 1 calc R U . . .
H21C H 0.6765 0.2043 0.5642 0.048 Uiso 1 1 calc R U . . .
C22R C 0.6751(4) 0.2912(4) 0.7125(4) 0.0231(14) Uani 1 1 d . . . . .
H22A H 0.6520 0.2294 0.6952 0.028 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O3 1.985(4) . ?
Cu1 O2 1.988(4) . ?
Cu1 O1R 2.002(4) 2_656 ?
Cu1 N18R 2.034(5) . ?
Cu1 O1 2.213(4) . ?
Cu1 O4 2.263(4) . ?
O1 C2 1.248(7) . ?
C1 F2A 1.27(3) . ?
C1 F1A 1.30(3) . ?
C1 F3 1.32(3) . ?
C1 F3A 1.31(3) . ?
C1 F1 1.35(3) . ?
C1 F2 1.35(3) . ?
C1 C2 1.545(9) . ?
C2 C3 1.402(8) . ?
C3 C4 1.398(8) . ?
C4 O2 1.261(7) . ?
C4 C5 1.518(9) . ?
C5 F4 1.327(7) . ?
C5 F6 1.341(7) . ?
C5 F5 1.347(7) . ?
O3 C7 1.271(7) . ?
C6 F9 1.316(7) . ?
C6 F7 1.338(7) . ?
C6 F8 1.307(7) . ?
C6 C7 1.533(9) . ?
C7 C8 1.383(8) . ?
C8 C9 1.412(8) . ?
C9 O4 1.229(7) . ?
C9 C10 1.542(9) . ?
C10 F11 1.328(8) . ?
C10 F10 1.334(8) . ?
C10 F12 1.340(7) . ?
O1R N2R 1.308(6) . ?
O1R Cu1 2.002(4) 2_646 ?
N2R C15R 1.343(7) . ?
N2R C3R 1.509(7) . ?
N2R Cu1 2.997(5) 2_646 ?
C3R C7R 1.520(8) . ?
C3R C4R 1.542(8) . ?
C3R C8R 1.558(8) . ?
C4R C5R 1.550(8) . ?
C5R C6R 1.531(8) . ?
C6R C7R 1.547(8) . ?
C8R N13R 1.503(7) . ?
C8R C9R 1.547(8) . ?
C8R C12R 1.561(8) . ?
C9R C10A 1.521(8) . ?
C10A C11A 1.509(9) . ?
C11A C12R 1.517(8) . ?
N13R O14R 1.280(6) . ?
N13R C15R 1.355(7) . ?
C15R C16R 1.433(8) . ?
C16R C17R 1.401(8) . ?
C16R C22R 1.408(8) . ?
C17R N18R 1.331(7) . ?
N18R N19R 1.375(6) . ?
N19R C22R 1.333(7) . ?
N19R C20R 1.482(7) . ?
C20R C21R 1.503(8) . ?

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
O3 Cu1 O2 177.40(17) . . ?
O3 Cu1 O1R 88.26(17) . 2_656 ?
O2 Cu1 O1R 91.67(17) . 2_656 ?
O3 Cu1 N18R 91.48(18) . . ?
O2 Cu1 N18R 87.96(18) . . ?
O1R Cu1 N18R 166.28(18) 2_656 . ?
O3 Cu1 O1 96.30(15) . . ?
O2 Cu1 O1 86.29(16) . . ?
O1R Cu1 O1 94.85(15) 2_656 . ?
N18R Cu1 O1 98.81(18) . . ?
O3 Cu1 O4 87.37(15) . . ?
O2 Cu1 O4 90.09(15) . . ?
O1R Cu1 O4 76.12(15) 2_656 . ?
N18R Cu1 O4 90.16(18) . . ?
O1 Cu1 O4 170.18(15) . . ?
C2 O1 Cu1 122.2(4) . . ?
F2A C1 F1A 107(2) . . ?
F2A C1 F3A 111.9(19) . . ?
F1A C1 F3A 102(2) . . ?
F3 C1 F1 110(2) . . ?
F3 C1 F2 102.9(19) . . ?
F1 C1 F2 109.1(19) . . ?
F2A C1 C2 114.4(16) . . ?
F1A C1 C2 111.7(13) . . ?
F3 C1 C2 111.6(10) . . ?
F3A C1 C2 109.6(14) . . ?
F1 C1 C2 109.1(11) . . ?
F2 C1 C2 114.0(15) . . ?
O1 C2 C3 128.5(6) . . ?
O1 C2 C1 115.2(6) . . ?
C3 C2 C1 116.2(6) . . ?
O1 C2 Cu1 37.6(3) . . ?
C3 C2 Cu1 91.6(4) . . ?
C1 C2 Cu1 151.9(4) . . ?
C4 C3 C2 122.4(6) . . ?
O2 C4 C3 128.4(6) . . ?
O2 C4 C5 113.0(6) . . ?
C3 C4 C5 118.6(6) . . ?
O2 C4 Cu1 32.0(3) . . ?
C3 C4 Cu1 96.9(4) . . ?
C5 C4 Cu1 144.1(4) . . ?
F4 C5 F6 107.0(5) . . ?
F4 C5 F5 107.3(5) . . ?
F6 C5 F5 106.0(5) . . ?
F4 C5 C4 111.7(5) . . ?
F6 C5 C4 114.0(5) . . ?
F5 C5 C4 110.4(5) . . ?
C4 O2 Cu1 128.4(4) . . ?
C7 O3 Cu1 125.9(4) . . ?
F9 C6 F7 105.4(6) . . ?
F9 C6 F8 107.1(6) . . ?
F7 C6 F8 106.5(5) . . ?
F9 C6 C7 111.6(5) . . ?
F7 C6 C7 110.6(5) . . ?
F8 C6 C7 115.1(5) . . ?
O3 C7 C8 129.7(6) . . ?
O3 C7 C6 113.0(5) . . ?
C8 C7 C6 117.3(5) . . ?
O3 C7 Cu1 33.5(3) . . ?
C8 C7 Cu1 96.7(4) . . ?
C6 C7 Cu1 145.3(4) . . ?
C7 C8 C9 123.1(6) . . ?
O4 C9 C8 129.0(6) . . ?
O4 C9 C10 115.3(6) . . ?
C8 C9 C10 115.7(5) . . ?
O4 C9 Cu1 41.1(3) . . ?
C8 C9 Cu1 90.8(4) . . ?
C10 C9 Cu1 148.0(4) . . ?
F11 C10 F10 107.8(6) . . ?
F11 C10 F12 106.9(6) . . ?
F10 C10 F12 107.4(6) . . ?
F11 C10 C9 114.5(6) . . ?
F10 C10 C9 108.9(6) . . ?
F12 C10 C9 111.1(6) . . ?
C9 O4 Cu1 118.0(4) . . ?
N2R O1R Cu1 128.6(3) . 2_646 ?
O1R N2R C15R 123.7(5) . . ?
O1R N2R C3R 121.2(5) . . ?
C15R N2R C3R 111.9(5) . . ?
O1R N2R Cu1 31.5(2) . 2_646 ?
C15R N2R Cu1 125.5(4) . 2_646 ?
C3R N2R Cu1 120.0(3) . 2_646 ?
N2R C3R C7R 113.0(5) . . ?
N2R C3R C4R 107.5(5) . . ?
C7R C3R C4R 103.8(5) . . ?
N2R C3R C8R 100.1(4) . . ?
C7R C3R C8R 117.1(5) . . ?
C4R C3R C8R 115.2(5) . . ?
C3R C4R C5R 104.4(5) . . ?
C6R C5R C4R 106.4(5) . . ?
C5R C6R C7R 103.8(5) . . ?
C3R C7R C6R 101.2(5) . . ?
N13R C8R C9R 110.6(5) . . ?
N13R C8R C3R 99.9(4) . . ?
C9R C8R C3R 117.9(5) . . ?
N13R C8R C12R 106.5(5) . . ?
C9R C8R C12R 104.2(5) . . ?
C3R C8R C12R 117.3(5) . . ?
C10A C9R C8R 106.4(5) . . ?
C11A C10A C9R 104.1(5) . . ?
C10A C11A C12R 102.5(5) . . ?
C11A C12R C8R 104.3(5) . . ?
O14R N13R C15R 124.2(5) . . ?
O14R N13R C8R 123.1(5) . . ?
C15R N13R C8R 112.5(5) . . ?
N2R C15R N13R 107.9(5) . . ?
N2R C15R C16R 126.9(5) . . ?
N13R C15R C16R 125.1(5) . . ?
C17R C16R C22R 104.4(5) . . ?
C17R C16R C15R 129.1(6) . . ?
C22R C16R C15R 126.5(6) . . ?
N18R C17R C16R 111.6(6) . . ?
N18R C17R Cu1 35.0(3) . . ?
C16R C17R Cu1 146.2(5) . . ?
C17R N18R N19R 105.0(5) . . ?
C17R N18R Cu1 123.0(4) . . ?
N19R N18R Cu1 131.4(4) . . ?
C22R N19R N18R 112.0(5) . . ?
C22R N19R C20R 127.9(5) . . ?
N18R N19R C20R 120.1(5) . . ?
C22R N19R Cu1 140.9(4) . . ?
N18R N19R Cu1 29.3(2) . . ?
C20R N19R Cu1 90.9(3) . . ?
N19R C20R C21R 112.1(5) . . ?
N19R C22R C16R 106.9(5) . . ?

_refine_diff_density_max         1.016
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.123

_shelxl_version_number           2014/6



_exptl_crystal_preparation       'Magnetic properties'
