# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ww
_database_code_depnum_ccdc_archive 'CCDC 1842067'
_audit_update_record             
;
2018-05-08 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        H2L
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H19 F N4 O3'
_chemical_formula_weight         430.43

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.634(2)
_cell_length_b                   10.978(2)
_cell_length_c                   11.159(2)
_cell_angle_alpha                61.590(2)
_cell_angle_beta                 71.105(2)
_cell_angle_gamma                73.667(2)
_cell_volume                     1071.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3766
_cell_measurement_theta_min      2.4763
_cell_measurement_theta_max      27.5708

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9801
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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-CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7518
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3766
_reflns_number_gt                3275
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0579P)²+0.1496P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.037(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3766
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.1034
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.003
_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
F1 F -0.63343(8) 0.62330(9) 0.86647(8) 0.0367(2) Uani 1 1 d . . .
O1 O -0.06316(10) 0.58603(9) 0.22122(9) 0.0240(2) Uani 1 1 d . . .
H1 H -0.0938 0.5296 0.3030 0.036 Uiso 1 1 calc R . .
O2 O 0.20906(9) 0.57071(9) 0.54399(9) 0.0226(2) Uani 1 1 d . . .
O3 O 0.18350(9) 0.79527(10) 0.12267(9) 0.0230(2) Uani 1 1 d . . .
H3 H 0.1834 0.8733 0.0529 0.035 Uiso 1 1 calc R . .
N1 N -0.12086(11) 0.82251(11) 0.07939(10) 0.0186(3) Uani 1 1 d . . .
N2 N -0.17441(11) 0.94805(11) 0.09061(11) 0.0207(3) Uani 1 1 d . . .
N3 N -0.04279(11) 0.65293(11) 0.49591(11) 0.0182(3) Uani 1 1 d . . .
N4 N 0.07192(11) 0.67940(11) 0.39084(11) 0.0183(3) Uani 1 1 d . . .
H4 H 0.0657 0.7231 0.3029 0.022 Uiso 1 1 calc R . .
C1 C 0.02150(15) 0.72102(16) -0.08226(15) 0.0281(3) Uani 1 1 d . . .
H1A H 0.0718 0.6573 -0.0140 0.034 Uiso 1 1 calc R . .
C2 C 0.05375(17) 0.71880(17) -0.21225(16) 0.0367(4) Uani 1 1 d . . .
H2 H 0.1250 0.6513 -0.2318 0.044 Uiso 1 1 calc R . .
C3 C -0.01654(19) 0.81360(18) -0.31331(16) 0.0418(4) Uani 1 1 d . . .
H3A H 0.0075 0.8125 -0.4026 0.050 Uiso 1 1 calc R . .
C4 C -0.12214(19) 0.91018(18) -0.28404(16) 0.0405(4) Uani 1 1 d . . .
H4A H -0.1702 0.9756 -0.3538 0.049 Uiso 1 1 calc R . .
C5 C -0.15851(16) 0.91232(15) -0.15357(14) 0.0291(3) Uani 1 1 d . . .
H5 H -0.2322 0.9774 -0.1331 0.035 Uiso 1 1 calc R . .
C6 C -0.08539(14) 0.81774(14) -0.05347(13) 0.0218(3) Uani 1 1 d . . .
C7 C -0.11106(12) 0.71641(13) 0.20744(13) 0.0174(3) Uani 1 1 d . . .
C8 C -0.15898(12) 0.77294(13) 0.30421(12) 0.0166(3) Uani 1 1 d . . .
C9 C -0.19744(13) 0.91708(13) 0.22565(13) 0.0190(3) Uani 1 1 d . . .
C10 C -0.25418(16) 1.02780(14) 0.27837(15) 0.0295(3) Uani 1 1 d . . .
H10A H -0.2537 1.1204 0.1990 0.044 Uiso 1 1 calc R . .
H10B H -0.1994 1.0195 0.3384 0.044 Uiso 1 1 calc R . .
H10C H -0.3467 1.0163 0.3323 0.044 Uiso 1 1 calc R . .
C11 C -0.15474(13) 0.70057(13) 0.45451(13) 0.0166(3) Uani 1 1 d . . .
C12 C -0.28116(13) 0.68349(13) 0.56349(13) 0.0183(3) Uani 1 1 d . . .
C13 C -0.40453(13) 0.71956(14) 0.52708(14) 0.0211(3) Uani 1 1 d . . .
H13 H -0.4070 0.7580 0.4314 0.025 Uiso 1 1 calc R . .
C14 C -0.52404(14) 0.70017(15) 0.62854(15) 0.0260(3) Uani 1 1 d . . .
H14 H -0.6080 0.7245 0.6036 0.031 Uiso 1 1 calc R . .
C15 C -0.51694(14) 0.64460(14) 0.76611(14) 0.0253(3) Uani 1 1 d . . .
C16 C -0.39759(15) 0.60927(15) 0.80693(14) 0.0271(3) Uani 1 1 d . . .
H16 H -0.3967 0.5724 0.9029 0.033 Uiso 1 1 calc R . .
C17 C -0.27886(14) 0.62856(14) 0.70515(14) 0.0237(3) Uani 1 1 d . . .
H17 H -0.1956 0.6045 0.7313 0.028 Uiso 1 1 calc R . .
C18 C 0.19364(13) 0.63868(13) 0.42216(13) 0.0175(3) Uani 1 1 d . . .
C19 C 0.31122(13) 0.67937(13) 0.30114(13) 0.0177(3) Uani 1 1 d . . .
C20 C 0.43723(14) 0.63766(14) 0.33368(15) 0.0236(3) Uani 1 1 d . . .
H20 H 0.4428 0.5873 0.4290 0.028 Uiso 1 1 calc R . .
C21 C 0.55435(14) 0.66756(16) 0.23115(16) 0.0290(3) Uani 1 1 d . . .
H21 H 0.6391 0.6373 0.2557 0.035 Uiso 1 1 calc R . .
C22 C 0.54627(15) 0.74222(16) 0.09214(16) 0.0308(4) Uani 1 1 d . . .
H22 H 0.6259 0.7635 0.0209 0.037 Uiso 1 1 calc R . .
C23 C 0.42270(15) 0.78585(15) 0.05675(15) 0.0274(3) Uani 1 1 d . . .
H23 H 0.4183 0.8377 -0.0388 0.033 Uiso 1 1 calc R . .
C24 C 0.30462(13) 0.75485(13) 0.15922(14) 0.0199(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C15 1.3634(15) . ?
O1 C7 1.3278(16) . ?
O1 H1 0.8400 . ?
O2 C18 1.2419(15) . ?
O3 C24 1.3671(16) . ?
O3 H3 0.8400 . ?
N1 C7 1.3615(16) . ?
N1 N2 1.3842(15) . ?
N1 C6 1.4296(16) . ?
N2 C9 1.3292(17) . ?
N3 C11 1.2963(17) . ?
N3 N4 1.3769(15) . ?
N4 C18 1.3478(17) . ?
N4 H4 0.8800 . ?
C1 C2 1.389(2) . ?
C1 C6 1.390(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.380(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.391(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.3836(18) . ?
C8 C9 1.4099(18) . ?
C8 C11 1.4857(17) . ?
C9 C10 1.4918(19) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.4790(18) . ?
C12 C13 1.3939(19) . ?
C12 C17 1.4045(18) . ?
C13 C14 1.3905(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(2) . ?
C16 C17 1.386(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.4943(18) . ?
C19 C20 1.3961(19) . ?
C19 C24 1.4107(18) . ?
C20 C21 1.385(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.387(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.3929(19) . ?
C23 H23 0.9500 . ?

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
C7 O1 H1 109.5 . . ?
C24 O3 H3 109.5 . . ?
C7 N1 N2 110.20(10) . . ?
C7 N1 C6 129.30(11) . . ?
N2 N1 C6 120.50(10) . . ?
C9 N2 N1 105.74(10) . . ?
C11 N3 N4 115.29(10) . . ?
C18 N4 N3 120.29(10) . . ?
C18 N4 H4 119.9 . . ?
N3 N4 H4 119.9 . . ?
C2 C1 C6 119.08(15) . . ?
C2 C1 H1A 120.5 . . ?
C6 C1 H1A 120.5 . . ?
C3 C2 C1 120.75(15) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.72(14) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C3 C4 C5 120.63(15) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 C6 119.05(15) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C5 120.73(13) . . ?
C1 C6 N1 120.32(12) . . ?
C5 C6 N1 118.94(12) . . ?
O1 C7 N1 120.37(11) . . ?
O1 C7 C8 131.82(11) . . ?
N1 C7 C8 107.81(11) . . ?
C7 C8 C9 104.90(11) . . ?
C7 C8 C11 127.20(11) . . ?
C9 C8 C11 127.50(11) . . ?
N2 C9 C8 111.35(11) . . ?
N2 C9 C10 121.30(11) . . ?
C8 C9 C10 127.33(11) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 C12 117.39(11) . . ?
N3 C11 C8 122.43(11) . . ?
C12 C11 C8 120.17(11) . . ?
C13 C12 C17 118.98(12) . . ?
C13 C12 C11 120.31(11) . . ?
C17 C12 C11 120.70(12) . . ?
C14 C13 C12 121.09(12) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 117.97(13) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
F1 C15 C14 118.38(13) . . ?
F1 C15 C16 118.62(12) . . ?
C14 C15 C16 123.00(13) . . ?
C15 C16 C17 118.65(13) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C16 C17 C12 120.30(13) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
O2 C18 N4 122.69(12) . . ?
O2 C18 C19 121.11(12) . . ?
N4 C18 C19 116.20(11) . . ?
C20 C19 C24 118.32(12) . . ?
C20 C19 C18 116.18(11) . . ?
C24 C19 C18 125.50(12) . . ?
C21 C20 C19 121.93(13) . . ?
C21 C20 H20 119.0 . . ?
C19 C20 H20 119.0 . . ?
C20 C21 C22 119.10(13) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C23 C22 C21 120.27(13) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.94(13) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
O3 C24 C23 120.38(12) . . ?
O3 C24 C19 120.19(11) . . ?
C23 C24 C19 119.43(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C9 -0.33(14) . . . . ?
C6 N1 N2 C9 179.32(11) . . . . ?
C11 N3 N4 C18 177.78(11) . . . . ?
C6 C1 C2 C3 1.8(2) . . . . ?
C1 C2 C3 C4 -1.3(2) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C1 C6 N1 -179.97(12) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C4 C5 C6 N1 178.44(12) . . . . ?
C7 N1 C6 C1 -32.2(2) . . . . ?
N2 N1 C6 C1 148.18(12) . . . . ?
C7 N1 C6 C5 148.48(14) . . . . ?
N2 N1 C6 C5 -31.10(17) . . . . ?
N2 N1 C7 O1 179.39(11) . . . . ?
C6 N1 C7 O1 -0.2(2) . . . . ?
N2 N1 C7 C8 0.08(14) . . . . ?
C6 N1 C7 C8 -179.54(12) . . . . ?
O1 C7 C8 C9 -179.01(13) . . . . ?
N1 C7 C8 C9 0.20(14) . . . . ?
O1 C7 C8 C11 7.8(2) . . . . ?
N1 C7 C8 C11 -172.97(12) . . . . ?
N1 N2 C9 C8 0.47(14) . . . . ?
N1 N2 C9 C10 179.17(12) . . . . ?
C7 C8 C9 N2 -0.42(14) . . . . ?
C11 C8 C9 N2 172.72(12) . . . . ?
C7 C8 C9 C10 -179.03(13) . . . . ?
C11 C8 C9 C10 -5.9(2) . . . . ?
N4 N3 C11 C12 -175.88(10) . . . . ?
N4 N3 C11 C8 2.69(17) . . . . ?
C7 C8 C11 N3 64.26(18) . . . . ?
C9 C8 C11 N3 -107.41(16) . . . . ?
C7 C8 C11 C12 -117.21(14) . . . . ?
C9 C8 C11 C12 71.12(17) . . . . ?
N3 C11 C12 C13 -173.59(11) . . . . ?
C8 C11 C12 C13 7.81(18) . . . . ?
N3 C11 C12 C17 5.29(18) . . . . ?
C8 C11 C12 C17 -173.32(12) . . . . ?
C17 C12 C13 C14 -0.89(19) . . . . ?
C11 C12 C13 C14 178.00(12) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C13 C14 C15 F1 -179.05(12) . . . . ?
C13 C14 C15 C16 0.8(2) . . . . ?
F1 C15 C16 C17 178.86(12) . . . . ?
C14 C15 C16 C17 -1.0(2) . . . . ?
C15 C16 C17 C12 0.2(2) . . . . ?
C13 C12 C17 C16 0.7(2) . . . . ?
C11 C12 C17 C16 -178.19(12) . . . . ?
N3 N4 C18 O2 3.63(18) . . . . ?
N3 N4 C18 C19 -176.66(10) . . . . ?
O2 C18 C19 C20 -0.53(18) . . . . ?
N4 C18 C19 C20 179.75(11) . . . . ?
O2 C18 C19 C24 179.24(12) . . . . ?
N4 C18 C19 C24 -0.48(18) . . . . ?
C24 C19 C20 C21 -0.4(2) . . . . ?
C18 C19 C20 C21 179.39(12) . . . . ?
C19 C20 C21 C22 0.6(2) . . . . ?
C20 C21 C22 C23 -0.1(2) . . . . ?
C21 C22 C23 C24 -0.6(2) . . . . ?
C22 C23 C24 O3 -178.23(12) . . . . ?
C22 C23 C24 C19 0.8(2) . . . . ?
C20 C19 C24 O3 178.71(11) . . . . ?
C18 C19 C24 O3 -1.05(19) . . . . ?
C20 C19 C24 C23 -0.29(19) . . . . ?
C18 C19 C24 C23 179.94(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_ww_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1842069'
_audit_update_record             
;
2018-05-08 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H25 Cu F N6 O3'
_chemical_formula_weight         672.16

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   5.7668(8)
_cell_length_b                   21.831(3)
_cell_length_c                   11.7987(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.694(2)
_cell_angle_gamma                90.00
_cell_volume                     1472.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2338
_cell_measurement_theta_min      2.5527
_cell_measurement_theta_max      23.7361

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             690
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8696
_exptl_absorpt_correction_T_max  0.8896
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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-CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7506
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0700
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4254
_reflns_number_gt                3757
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0284P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.002(12)
_refine_ls_number_reflns         4254
_refine_ls_number_parameters     424
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0783
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.83048(7) 0.73362(2) 0.16146(4) 0.01679(12) Uani 1 1 d . . .
N1 N 1.0238(5) 0.77393(14) 0.3785(3) 0.0200(8) Uani 1 1 d . . .
N2 N 1.0419(5) 0.72601(19) 0.3019(2) 0.0178(7) Uani 1 1 d . . .
N3 N 1.3797(5) 0.55387(15) 0.1677(3) 0.0248(8) Uani 1 1 d . . .
N4 N 1.1726(6) 0.57447(14) 0.1030(3) 0.0220(8) Uani 1 1 d . . .
N5 N 0.9981(6) 0.80885(14) 0.0697(3) 0.0217(8) Uani 1 1 d . . .
N6 N 0.6010(5) 0.74403(17) 0.0213(3) 0.0210(9) Uani 1 1 d . . .
O1 O 1.1832(5) 0.84622(15) 0.5386(3) 0.0428(10) Uani 1 1 d . . .
H1 H 1.1795 0.8145 0.4980 0.064 Uiso 1 1 calc R . .
O2 O 0.7014(4) 0.80052(12) 0.2501(2) 0.0209(6) Uani 1 1 d . . .
O3 O 0.8987(5) 0.65307(12) 0.1059(2) 0.0218(7) Uani 1 1 d . . .
F1 F 1.7172(4) 0.67902(12) 0.7692(2) 0.0396(7) Uani 1 1 d . . .
C1 C 0.9922(8) 0.8814(2) 0.5035(4) 0.0293(11) Uani 1 1 d . . .
C2 C 0.9710(8) 0.9359(2) 0.5633(4) 0.0336(12) Uani 1 1 d . . .
H2A H 1.0909 0.9479 0.6223 0.040 Uiso 1 1 calc R . .
C3 C 0.7763(8) 0.97233(19) 0.5366(4) 0.0311(11) Uani 1 1 d . . .
H3A H 0.7614 1.0092 0.5778 0.037 Uiso 1 1 calc R . .
C4 C 0.6023(8) 0.95545(19) 0.4499(4) 0.0313(11) Uani 1 1 d . . .
H4A H 0.4664 0.9801 0.4329 0.038 Uiso 1 1 calc R . .
C5 C 0.6264(8) 0.9027(2) 0.3881(4) 0.0268(11) Uani 1 1 d . . .
H5A H 0.5074 0.8918 0.3278 0.032 Uiso 1 1 calc R . .
C6 C 0.8219(7) 0.86500(18) 0.4125(3) 0.0190(9) Uani 1 1 d . . .
C7 C 0.8475(7) 0.81019(18) 0.3414(4) 0.0197(9) Uani 1 1 d . . .
C8 C 1.1937(6) 0.68253(17) 0.3356(3) 0.0194(9) Uani 1 1 d . . .
C9 C 1.3292(6) 0.68280(17) 0.4517(3) 0.0185(9) Uani 1 1 d . . .
C10 C 1.5211(7) 0.7215(2) 0.4775(4) 0.0407(15) Uani 1 1 d . . .
H10A H 1.5622 0.7491 0.4213 0.049 Uiso 1 1 calc R . .
C11 C 1.6526(7) 0.7198(2) 0.5850(4) 0.0359(13) Uani 1 1 d . . .
H11A H 1.7850 0.7456 0.6027 0.043 Uiso 1 1 calc R . .
C12 C 1.5886(7) 0.6806(2) 0.6639(4) 0.0268(10) Uani 1 1 d . . .
C13 C 1.3984(7) 0.6419(2) 0.6421(4) 0.0281(10) Uani 1 1 d . . .
H13A H 1.3573 0.6150 0.6995 0.034 Uiso 1 1 calc R . .
C14 C 1.2703(7) 0.64335(18) 0.5352(4) 0.0224(10) Uani 1 1 d . . .
H14A H 1.1394 0.6169 0.5184 0.027 Uiso 1 1 calc R . .
C15 C 1.0809(7) 0.62380(17) 0.1530(4) 0.0196(9) Uani 1 1 d . . .
C16 C 1.2271(6) 0.63408(17) 0.2567(3) 0.0184(9) Uani 1 1 d . . .
C17 C 1.4069(7) 0.58937(18) 0.2589(4) 0.0215(10) Uani 1 1 d . . .
C18 C 1.6251(8) 0.5810(2) 0.3423(4) 0.0297(12) Uani 1 1 d . . .
H18A H 1.7136 0.5459 0.3189 0.045 Uiso 1 1 calc R . .
H18B H 1.5827 0.5735 0.4188 0.045 Uiso 1 1 calc R . .
H18C H 1.7215 0.6180 0.3436 0.045 Uiso 1 1 calc R . .
C19 C 1.1116(8) 0.54939(18) -0.0085(4) 0.0242(11) Uani 1 1 d . . .
C20 C 1.2657(8) 0.5144(3) -0.0546(5) 0.0587(18) Uani 1 1 d . . .
H20A H 1.4145 0.5063 -0.0123 0.070 Uiso 1 1 calc R . .
C21 C 1.2112(10) 0.4906(4) -0.1610(5) 0.079(2) Uani 1 1 d . . .
H21A H 1.3246 0.4663 -0.1916 0.095 Uiso 1 1 calc R . .
C22 C 1.0013(8) 0.5001(2) -0.2255(4) 0.0376(12) Uani 1 1 d . . .
H22A H 0.9660 0.4826 -0.2995 0.045 Uiso 1 1 calc R . .
C23 C 0.8437(10) 0.5354(2) -0.1799(5) 0.0501(16) Uani 1 1 d . . .
H23A H 0.6960 0.5434 -0.2234 0.060 Uiso 1 1 calc R . .
C24 C 0.8942(9) 0.5603(2) -0.0705(5) 0.0493(17) Uani 1 1 d . . .
H24A H 0.7813 0.5844 -0.0390 0.059 Uiso 1 1 calc R . .
C25 C 1.1904(8) 0.84197(19) 0.0976(4) 0.0292(11) Uani 1 1 d . . .
H25A H 1.2972 0.8305 0.1625 0.035 Uiso 1 1 calc R . .
C26 C 1.2399(11) 0.8927(2) 0.0347(5) 0.0485(15) Uani 1 1 d . . .
H26A H 1.3794 0.9153 0.0567 0.058 Uiso 1 1 calc R . .
C27 C 1.0908(13) 0.9104(2) -0.0581(5) 0.058(2) Uani 1 1 d . . .
H27A H 1.1245 0.9454 -0.1008 0.070 Uiso 1 1 calc R . .
C28 C 0.8885(11) 0.8768(2) -0.0899(4) 0.0432(15) Uani 1 1 d . . .
C29 C 0.7208(14) 0.8898(3) -0.1891(5) 0.068(2) Uani 1 1 d U . .
H29A H 0.7437 0.9244 -0.2350 0.082 Uiso 1 1 calc R . .
C30 C 0.5357(13) 0.8544(3) -0.2174(5) 0.0644(19) Uani 1 1 d U . .
H30A H 0.4342 0.8632 -0.2857 0.077 Uiso 1 1 calc R . .
C31 C 0.4831(9) 0.8039(2) -0.1495(4) 0.0457(14) Uani 1 1 d U . .
C32 C 0.2875(10) 0.7659(3) -0.1747(5) 0.0587(18) Uani 1 1 d U . .
H32A H 0.1783 0.7734 -0.2410 0.070 Uiso 1 1 calc R . .
C33 C 0.2538(8) 0.7185(3) -0.1044(5) 0.0541(19) Uani 1 1 d . . .
H33A H 0.1220 0.6924 -0.1214 0.065 Uiso 1 1 calc R . .
C34 C 0.4149(7) 0.7085(2) -0.0066(4) 0.0377(13) Uani 1 1 d . . .
H34A H 0.3903 0.6750 0.0418 0.045 Uiso 1 1 calc R . .
C35 C 0.6387(7) 0.7905(2) -0.0497(4) 0.0278(11) Uani 1 1 d . . .
C36 C 0.8477(8) 0.82667(18) -0.0214(4) 0.0241(10) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.929(3) . ?
Cu1 O3 1.935(3) . ?
Cu1 N6 1.988(3) . ?
Cu1 O2 1.997(3) . ?
Cu1 N5 2.255(3) . ?
N1 C7 1.316(5) . ?
N1 N2 1.395(5) . ?
N2 C8 1.316(5) . ?
N3 C17 1.319(5) . ?
N3 N4 1.402(4) . ?
N4 C15 1.368(5) . ?
N4 C19 1.425(6) . ?
N5 C25 1.328(5) . ?
N5 C36 1.346(5) . ?
N6 C34 1.329(5) . ?
N6 C35 1.352(5) . ?
O1 C1 1.360(5) . ?
O1 H1 0.8400 . ?
O2 C7 1.293(4) . ?
O3 C15 1.290(5) . ?
F1 C12 1.359(4) . ?
C1 C2 1.399(6) . ?
C1 C6 1.401(6) . ?
C2 C3 1.377(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.383(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.380(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.394(6) . ?
C5 H5A 0.9500 . ?
C6 C7 1.480(5) . ?
C8 C16 1.438(5) . ?
C8 C9 1.484(5) . ?
C9 C14 1.385(6) . ?
C9 C10 1.393(5) . ?
C10 C11 1.388(6) . ?
C10 H10A 0.9500 . ?
C11 C12 1.350(6) . ?
C11 H11A 0.9500 . ?
C12 C13 1.382(6) . ?
C13 C14 1.374(5) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 C16 1.408(5) . ?
C16 C17 1.422(5) . ?
C17 C18 1.501(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.340(6) . ?
C19 C24 1.385(6) . ?
C20 C21 1.356(7) . ?
C20 H20A 0.9500 . ?
C21 C22 1.356(6) . ?
C21 H21A 0.9500 . ?
C22 C23 1.357(7) . ?
C22 H22A 0.9500 . ?
C23 C24 1.395(7) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?
C25 C26 1.384(7) . ?
C25 H25A 0.9500 . ?
C26 C27 1.354(8) . ?
C26 H26A 0.9500 . ?
C27 C28 1.386(8) . ?
C27 H27A 0.9500 . ?
C28 C36 1.400(6) . ?
C28 C29 1.442(8) . ?
C29 C30 1.324(9) . ?
C29 H29A 0.9500 . ?
C30 C31 1.419(8) . ?
C30 H30A 0.9500 . ?
C31 C32 1.399(8) . ?
C31 C35 1.413(6) . ?
C32 C33 1.357(8) . ?
C32 H32A 0.9500 . ?
C33 C34 1.398(6) . ?
C33 H33A 0.9500 . ?
C34 H34A 0.9500 . ?
C35 C36 1.441(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
N2 Cu1 O3 94.54(14) . . ?
N2 Cu1 N6 176.91(15) . . ?
O3 Cu1 N6 87.98(13) . . ?
N2 Cu1 O2 81.37(14) . . ?
O3 Cu1 O2 161.56(12) . . ?
N6 Cu1 O2 95.68(12) . . ?
N2 Cu1 N5 102.29(14) . . ?
O3 Cu1 N5 112.30(13) . . ?
N6 Cu1 N5 78.33(14) . . ?
O2 Cu1 N5 86.13(12) . . ?
C7 N1 N2 110.9(3) . . ?
C8 N2 N1 116.8(3) . . ?
C8 N2 Cu1 129.8(3) . . ?
N1 N2 Cu1 113.5(2) . . ?
C17 N3 N4 104.8(3) . . ?
C15 N4 N3 111.6(3) . . ?
C15 N4 C19 129.7(3) . . ?
N3 N4 C19 117.8(4) . . ?
C25 N5 C36 117.9(4) . . ?
C25 N5 Cu1 132.5(3) . . ?
C36 N5 Cu1 108.8(3) . . ?
C34 N6 C35 118.5(4) . . ?
C34 N6 Cu1 124.4(3) . . ?
C35 N6 Cu1 117.2(3) . . ?
C1 O1 H1 109.5 . . ?
C7 O2 Cu1 108.0(2) . . ?
C15 O3 Cu1 119.7(3) . . ?
O1 C1 C2 116.7(4) . . ?
O1 C1 C6 123.1(4) . . ?
C2 C1 C6 120.3(4) . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C5 C6 C1 118.2(4) . . ?
C5 C6 C7 120.0(4) . . ?
C1 C6 C7 121.8(4) . . ?
O2 C7 N1 124.5(4) . . ?
O2 C7 C6 120.0(3) . . ?
N1 C7 C6 115.5(3) . . ?
N2 C8 C16 118.5(4) . . ?
N2 C8 C9 121.5(3) . . ?
C16 C8 C9 120.0(3) . . ?
C14 C9 C10 119.0(4) . . ?
C14 C9 C8 120.4(3) . . ?
C10 C9 C8 120.6(4) . . ?
C11 C10 C9 120.2(4) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C12 C11 C10 118.7(4) . . ?
C12 C11 H11A 120.6 . . ?
C10 C11 H11A 120.6 . . ?
C11 C12 F1 118.7(4) . . ?
C11 C12 C13 122.8(4) . . ?
F1 C12 C13 118.5(4) . . ?
C14 C13 C12 118.2(4) . . ?
C14 C13 H13A 120.9 . . ?
C12 C13 H13A 120.9 . . ?
C13 C14 C9 120.9(4) . . ?
C13 C14 H14A 119.5 . . ?
C9 C14 H14A 119.5 . . ?
O3 C15 N4 122.9(4) . . ?
O3 C15 C16 130.8(4) . . ?
N4 C15 C16 106.2(3) . . ?
C15 C16 C17 104.9(3) . . ?
C15 C16 C8 124.3(3) . . ?
C17 C16 C8 130.8(4) . . ?
N3 C17 C16 112.4(4) . . ?
N3 C17 C18 117.5(4) . . ?
C16 C17 C18 129.9(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 119.1(5) . . ?
C20 C19 N4 119.9(4) . . ?
C24 C19 N4 121.0(4) . . ?
C19 C20 C21 120.6(5) . . ?
C19 C20 H20A 119.7 . . ?
C21 C20 H20A 119.7 . . ?
C20 C21 C22 122.6(5) . . ?
C20 C21 H21A 118.7 . . ?
C22 C21 H21A 118.7 . . ?
C21 C22 C23 117.3(5) . . ?
C21 C22 H22A 121.3 . . ?
C23 C22 H22A 121.3 . . ?
C22 C23 C24 121.4(5) . . ?
C22 C23 H23A 119.3 . . ?
C24 C23 H23A 119.3 . . ?
C19 C24 C23 118.9(5) . . ?
C19 C24 H24A 120.6 . . ?
C23 C24 H24A 120.6 . . ?
N5 C25 C26 121.9(5) . . ?
N5 C25 H25A 119.1 . . ?
C26 C25 H25A 119.1 . . ?
C27 C26 C25 120.5(5) . . ?
C27 C26 H26A 119.8 . . ?
C25 C26 H26A 119.8 . . ?
C26 C27 C28 119.3(5) . . ?
C26 C27 H27A 120.4 . . ?
C28 C27 H27A 120.4 . . ?
C27 C28 C36 117.2(5) . . ?
C27 C28 C29 124.4(6) . . ?
C36 C28 C29 118.4(6) . . ?
C30 C29 C28 121.4(6) . . ?
C30 C29 H29A 119.3 . . ?
C28 C29 H29A 119.3 . . ?
C29 C30 C31 122.5(5) . . ?
C29 C30 H30A 118.8 . . ?
C31 C30 H30A 118.8 . . ?
C32 C31 C35 117.3(5) . . ?
C32 C31 C30 124.6(5) . . ?
C35 C31 C30 118.1(5) . . ?
C33 C32 C31 119.9(5) . . ?
C33 C32 H32A 120.0 . . ?
C31 C32 H32A 120.0 . . ?
C32 C33 C34 119.4(5) . . ?
C32 C33 H33A 120.3 . . ?
C34 C33 H33A 120.3 . . ?
N6 C34 C33 122.5(5) . . ?
N6 C34 H34A 118.7 . . ?
C33 C34 H34A 118.7 . . ?
N6 C35 C31 122.3(4) . . ?
N6 C35 C36 117.8(4) . . ?
C31 C35 C36 119.9(4) . . ?
N5 C36 C28 123.2(4) . . ?
N5 C36 C35 117.2(4) . . ?
C28 C36 C35 119.6(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C8 -172.1(3) . . . . ?
C7 N1 N2 Cu1 6.7(4) . . . . ?
O3 Cu1 N2 C8 6.7(4) . . . . ?
N6 Cu1 N2 C8 151(3) . . . . ?
O2 Cu1 N2 C8 168.6(4) . . . . ?
N5 Cu1 N2 C8 -107.3(3) . . . . ?
O3 Cu1 N2 N1 -171.9(2) . . . . ?
N6 Cu1 N2 N1 -27(3) . . . . ?
O2 Cu1 N2 N1 -10.0(2) . . . . ?
N5 Cu1 N2 N1 74.1(3) . . . . ?
C17 N3 N4 C15 2.5(4) . . . . ?
C17 N3 N4 C19 172.6(3) . . . . ?
N2 Cu1 N5 C25 0.0(4) . . . . ?
O3 Cu1 N5 C25 -100.2(4) . . . . ?
N6 Cu1 N5 C25 176.9(4) . . . . ?
O2 Cu1 N5 C25 80.2(4) . . . . ?
N2 Cu1 N5 C36 -169.3(3) . . . . ?
O3 Cu1 N5 C36 90.5(3) . . . . ?
N6 Cu1 N5 C36 7.6(3) . . . . ?
O2 Cu1 N5 C36 -89.0(3) . . . . ?
N2 Cu1 N6 C34 -84(3) . . . . ?
O3 Cu1 N6 C34 61.0(3) . . . . ?
O2 Cu1 N6 C34 -100.9(3) . . . . ?
N5 Cu1 N6 C34 174.3(3) . . . . ?
N2 Cu1 N6 C35 96(3) . . . . ?
O3 Cu1 N6 C35 -119.0(3) . . . . ?
O2 Cu1 N6 C35 79.1(3) . . . . ?
N5 Cu1 N6 C35 -5.8(3) . . . . ?
N2 Cu1 O2 C7 11.3(2) . . . . ?
O3 Cu1 O2 C7 89.7(4) . . . . ?
N6 Cu1 O2 C7 -169.6(2) . . . . ?
N5 Cu1 O2 C7 -91.7(2) . . . . ?
N2 Cu1 O3 C15 -15.1(3) . . . . ?
N6 Cu1 O3 C15 166.7(3) . . . . ?
O2 Cu1 O3 C15 -91.3(4) . . . . ?
N5 Cu1 O3 C15 90.2(3) . . . . ?
O1 C1 C2 C3 -176.6(4) . . . . ?
C6 C1 C2 C3 3.2(7) . . . . ?
C1 C2 C3 C4 -0.7(7) . . . . ?
C2 C3 C4 C5 -1.5(7) . . . . ?
C3 C4 C5 C6 1.1(7) . . . . ?
C4 C5 C6 C1 1.4(6) . . . . ?
C4 C5 C6 C7 -177.3(4) . . . . ?
O1 C1 C6 C5 176.3(4) . . . . ?
C2 C1 C6 C5 -3.6(6) . . . . ?
O1 C1 C6 C7 -5.0(6) . . . . ?
C2 C1 C6 C7 175.1(4) . . . . ?
Cu1 O2 C7 N1 -12.1(4) . . . . ?
Cu1 O2 C7 C6 168.2(3) . . . . ?
N2 N1 C7 O2 4.2(5) . . . . ?
N2 N1 C7 C6 -176.1(3) . . . . ?
C5 C6 C7 O2 6.9(6) . . . . ?
C1 C6 C7 O2 -171.7(4) . . . . ?
C5 C6 C7 N1 -172.8(4) . . . . ?
C1 C6 C7 N1 8.5(6) . . . . ?
N1 N2 C8 C16 -176.6(3) . . . . ?
Cu1 N2 C8 C16 4.8(5) . . . . ?
N1 N2 C8 C9 3.3(5) . . . . ?
Cu1 N2 C8 C9 -175.3(3) . . . . ?
N2 C8 C9 C14 104.4(4) . . . . ?
C16 C8 C9 C14 -75.8(5) . . . . ?
N2 C8 C9 C10 -77.4(5) . . . . ?
C16 C8 C9 C10 102.5(5) . . . . ?
C14 C9 C10 C11 0.8(6) . . . . ?
C8 C9 C10 C11 -177.5(4) . . . . ?
C9 C10 C11 C12 -0.9(7) . . . . ?
C10 C11 C12 F1 -179.9(4) . . . . ?
C10 C11 C12 C13 0.3(7) . . . . ?
C11 C12 C13 C14 0.3(7) . . . . ?
F1 C12 C13 C14 -179.4(4) . . . . ?
C12 C13 C14 C9 -0.4(6) . . . . ?
C10 C9 C14 C13 -0.1(6) . . . . ?
C8 C9 C14 C13 178.1(4) . . . . ?
Cu1 O3 C15 N4 -163.8(3) . . . . ?
Cu1 O3 C15 C16 14.2(6) . . . . ?
N3 N4 C15 O3 175.7(4) . . . . ?
C19 N4 C15 O3 7.0(7) . . . . ?
N3 N4 C15 C16 -2.8(4) . . . . ?
C19 N4 C15 C16 -171.4(4) . . . . ?
O3 C15 C16 C17 -176.3(4) . . . . ?
N4 C15 C16 C17 1.9(4) . . . . ?
O3 C15 C16 C8 1.0(7) . . . . ?
N4 C15 C16 C8 179.3(4) . . . . ?
N2 C8 C16 C15 -11.5(6) . . . . ?
C9 C8 C16 C15 168.6(4) . . . . ?
N2 C8 C16 C17 165.2(4) . . . . ?
C9 C8 C16 C17 -14.7(6) . . . . ?
N4 N3 C17 C16 -1.2(4) . . . . ?
N4 N3 C17 C18 -176.2(3) . . . . ?
C15 C16 C17 N3 -0.5(5) . . . . ?
C8 C16 C17 N3 -177.6(4) . . . . ?
C15 C16 C17 C18 173.8(4) . . . . ?
C8 C16 C17 C18 -3.3(7) . . . . ?
C15 N4 C19 C20 158.5(5) . . . . ?
N3 N4 C19 C20 -9.6(6) . . . . ?
C15 N4 C19 C24 -21.8(7) . . . . ?
N3 N4 C19 C24 170.2(4) . . . . ?
C24 C19 C20 C21 0.8(9) . . . . ?
N4 C19 C20 C21 -179.5(6) . . . . ?
C19 C20 C21 C22 -0.6(11) . . . . ?
C20 C21 C22 C23 0.6(10) . . . . ?
C21 C22 C23 C24 -0.9(9) . . . . ?
C20 C19 C24 C23 -1.1(8) . . . . ?
N4 C19 C24 C23 179.2(5) . . . . ?
C22 C23 C24 C19 1.1(9) . . . . ?
C36 N5 C25 C26 -1.2(6) . . . . ?
Cu1 N5 C25 C26 -169.6(3) . . . . ?
N5 C25 C26 C27 0.3(7) . . . . ?
C25 C26 C27 C28 -0.4(8) . . . . ?
C26 C27 C28 C36 1.4(7) . . . . ?
C26 C27 C28 C29 -177.7(5) . . . . ?
C27 C28 C29 C30 177.2(5) . . . . ?
C36 C28 C29 C30 -1.9(8) . . . . ?
C28 C29 C30 C31 3.5(9) . . . . ?
C29 C30 C31 C32 178.7(5) . . . . ?
C29 C30 C31 C35 -1.5(8) . . . . ?
C35 C31 C32 C33 -0.1(7) . . . . ?
C30 C31 C32 C33 179.7(5) . . . . ?
C31 C32 C33 C34 0.6(7) . . . . ?
C35 N6 C34 C33 -1.9(6) . . . . ?
Cu1 N6 C34 C33 178.0(3) . . . . ?
C32 C33 C34 N6 0.4(7) . . . . ?
C34 N6 C35 C31 2.4(6) . . . . ?
Cu1 N6 C35 C31 -177.5(3) . . . . ?
C34 N6 C35 C36 -176.9(4) . . . . ?
Cu1 N6 C35 C36 3.2(4) . . . . ?
C32 C31 C35 N6 -1.4(6) . . . . ?
C30 C31 C35 N6 178.8(4) . . . . ?
C32 C31 C35 C36 177.8(4) . . . . ?
C30 C31 C35 C36 -1.9(6) . . . . ?
C25 N5 C36 C28 2.3(6) . . . . ?
Cu1 N5 C36 C28 173.3(3) . . . . ?
C25 N5 C36 C35 -179.4(4) . . . . ?
Cu1 N5 C36 C35 -8.4(4) . . . . ?
C27 C28 C36 N5 -2.4(7) . . . . ?
C29 C28 C36 N5 176.8(4) . . . . ?
C27 C28 C36 C35 179.3(4) . . . . ?
C29 C28 C36 C35 -1.5(6) . . . . ?
N6 C35 C36 N5 4.3(5) . . . . ?
C31 C35 C36 N5 -175.0(4) . . . . ?
N6 C35 C36 C28 -177.3(4) . . . . ?
C31 C35 C36 C28 3.4(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_ww_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1842068'
_audit_update_record             
;
2018-05-08 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H25 Cu F N6 O3'
_chemical_formula_weight         648.14

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21

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

_cell_length_a                   22.358(7)
_cell_length_b                   5.9648(18)
_cell_length_c                   21.456(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2861.4(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2779
_cell_measurement_theta_min      2.6314
_cell_measurement_theta_max      22.4488

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1332
_exptl_absorpt_coefficient_mu    0.818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8734
_exptl_absorpt_correction_T_max  0.8871
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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-ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13406
_diffrn_reflns_av_R_equivalents  0.0925
_diffrn_reflns_av_sigmaI/netI    0.1032
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4915
_reflns_number_gt                4043
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1029P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_number_reflns         4915
_refine_ls_number_parameters     406
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_ref         0.1737
_refine_ls_wR_factor_gt          0.1627
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.41799(3) 0.66284(11) 0.07429(4) 0.0183(2) Uani 1 1 d . . .
F1 F 0.11869(17) -0.1455(7) 0.1441(2) 0.0340(10) Uani 1 1 d . . .
N1 N 0.3048(2) 0.5209(9) 0.0342(2) 0.0180(12) Uani 1 1 d . . .
N2 N 0.3456(2) 0.4814(8) 0.0818(3) 0.0194(11) Uani 1 1 d . . .
N3 N 0.4205(2) 0.1560(8) 0.2609(3) 0.0215(13) Uani 1 1 d . . .
N4 N 0.4503(3) 0.3495(8) 0.2402(3) 0.0217(12) Uani 1 1 d . . .
N5 N 0.4912(2) 0.8522(8) 0.0651(3) 0.0180(12) Uani 1 1 d . . .
N6 N 0.4716(2) 0.4741(9) 0.0052(2) 0.0196(12) Uani 1 1 d . . .
O1 O 0.2151(2) 0.4314(8) -0.0367(2) 0.0276(11) Uani 1 1 d . . .
H1 H 0.2396 0.4104 -0.0075 0.041 Uiso 1 1 calc R . .
O2 O 0.37039(18) 0.8007(7) 0.0064(2) 0.0211(10) Uani 1 1 d . . .
O3 O 0.4447(2) 0.6089(7) 0.1592(2) 0.0220(10) Uani 1 1 d . . .
C1 C 0.2311(3) 0.6196(11) -0.0693(3) 0.0235(15) Uani 1 1 d . . .
C2 C 0.1950(3) 0.6779(12) -0.1190(3) 0.0290(17) Uani 1 1 d . . .
H2A H 0.1621 0.5861 -0.1305 0.035 Uiso 1 1 calc R . .
C3 C 0.2079(3) 0.8767(13) -0.1528(3) 0.0291(17) Uani 1 1 d . . .
H3A H 0.1829 0.9198 -0.1865 0.035 Uiso 1 1 calc R . .
C4 C 0.2558(3) 1.0061(12) -0.1372(3) 0.0279(16) Uani 1 1 d . . .
H4A H 0.2640 1.1386 -0.1602 0.033 Uiso 1 1 calc R . .
C5 C 0.2926(3) 0.9467(12) -0.0883(3) 0.0245(15) Uani 1 1 d . . .
H5A H 0.3256 1.0396 -0.0779 0.029 Uiso 1 1 calc R . .
C6 C 0.2818(3) 0.7487(11) -0.0532(3) 0.0195(14) Uani 1 1 d . . .
C7 C 0.3225(3) 0.6894(10) -0.0018(3) 0.0189(14) Uani 1 1 d . . .
C8 C 0.3306(3) 0.3453(10) 0.1273(3) 0.0164(13) Uani 1 1 d . . .
C9 C 0.2722(3) 0.2307(11) 0.1288(3) 0.0173(14) Uani 1 1 d . . .
C10 C 0.2583(3) 0.0617(11) 0.0846(3) 0.0270(17) Uani 1 1 d . . .
H10A H 0.2846 0.0355 0.0506 0.032 Uiso 1 1 calc R . .
C11 C 0.2072(3) -0.0642(12) 0.0905(3) 0.0307(18) Uani 1 1 d . . .
H11A H 0.1988 -0.1798 0.0613 0.037 Uiso 1 1 calc R . .
C12 C 0.1690(3) -0.0227(11) 0.1380(3) 0.0261(16) Uani 1 1 d . . .
C13 C 0.1800(3) 0.1459(12) 0.1816(3) 0.0278(16) Uani 1 1 d . . .
H13A H 0.1520 0.1757 0.2140 0.033 Uiso 1 1 calc R . .
C14 C 0.2321(3) 0.2687(11) 0.1769(3) 0.0208(14) Uani 1 1 d . . .
H14A H 0.2407 0.3808 0.2071 0.025 Uiso 1 1 calc R . .
C15 C 0.4222(3) 0.4381(12) 0.1886(3) 0.0204(14) Uani 1 1 d . . .
C16 C 0.3714(3) 0.3057(10) 0.1770(3) 0.0195(14) Uani 1 1 d . . .
C17 C 0.3743(3) 0.1333(11) 0.2235(3) 0.0210(15) Uani 1 1 d . . .
C18 C 0.3348(3) -0.0692(11) 0.2319(3) 0.0272(16) Uani 1 1 d . . .
H18A H 0.3481 -0.1546 0.2684 0.041 Uiso 1 1 calc R . .
H18B H 0.3372 -0.1642 0.1948 0.041 Uiso 1 1 calc R . .
H18C H 0.2933 -0.0206 0.2381 0.041 Uiso 1 1 calc R . .
C19 C 0.5042(3) 0.4145(11) 0.2697(3) 0.0189(14) Uani 1 1 d . . .
C20 C 0.5296(3) 0.6264(11) 0.2600(3) 0.0234(15) Uani 1 1 d . . .
H20A H 0.5108 0.7320 0.2333 0.028 Uiso 1 1 calc R . .
C21 C 0.5825(3) 0.6790(11) 0.2902(3) 0.0263(16) Uani 1 1 d . . .
H21A H 0.6004 0.8213 0.2830 0.032 Uiso 1 1 calc R . .
C22 C 0.6104(3) 0.5290(12) 0.3306(3) 0.0281(16) Uani 1 1 d . . .
H22A H 0.6464 0.5682 0.3514 0.034 Uiso 1 1 calc R . .
C23 C 0.5839(3) 0.3191(13) 0.3398(4) 0.036(2) Uani 1 1 d . . .
H23A H 0.6017 0.2152 0.3677 0.043 Uiso 1 1 calc R . .
C24 C 0.5327(3) 0.2619(12) 0.3090(4) 0.0275(16) Uani 1 1 d . . .
H24A H 0.5162 0.1164 0.3145 0.033 Uiso 1 1 calc R . .
C25 C 0.5014(3) 1.0301(11) 0.1022(3) 0.0214(15) Uani 1 1 d . . .
H25A H 0.4718 1.0693 0.1321 0.026 Uiso 1 1 calc R . .
C26 C 0.5520(3) 1.1570(11) 0.0990(3) 0.0259(16) Uani 1 1 d . . .
H26A H 0.5576 1.2815 0.1260 0.031 Uiso 1 1 calc R . .
C27 C 0.5945(3) 1.1001(12) 0.0559(3) 0.0288(19) Uani 1 1 d . . .
H27A H 0.6303 1.1851 0.0521 0.035 Uiso 1 1 calc R . .
C28 C 0.5845(3) 0.9163(12) 0.0177(3) 0.0264(16) Uani 1 1 d . . .
H28A H 0.6135 0.8741 -0.0124 0.032 Uiso 1 1 calc R . .
C29 C 0.5325(3) 0.7956(11) 0.0236(3) 0.0186(14) Uani 1 1 d . . .
C30 C 0.5201(3) 0.5870(11) -0.0135(3) 0.0172(14) Uani 1 1 d . . .
C31 C 0.5546(3) 0.5172(12) -0.0632(3) 0.0296(17) Uani 1 1 d . . .
H31A H 0.5879 0.6032 -0.0766 0.036 Uiso 1 1 calc R . .
C32 C 0.5394(3) 0.3171(12) -0.0933(3) 0.0319(18) Uani 1 1 d . . .
H32A H 0.5631 0.2619 -0.1266 0.038 Uiso 1 1 calc R . .
C33 C 0.4897(3) 0.2024(13) -0.0738(3) 0.0312(17) Uani 1 1 d . . .
H33A H 0.4784 0.0678 -0.0943 0.037 Uiso 1 1 calc R . .
C34 C 0.4564(3) 0.2800(12) -0.0252(3) 0.0239(16) Uani 1 1 d . . .
H34A H 0.4222 0.1983 -0.0121 0.029 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 O3 1.945(4) . ?
Cu1 N2 1.953(5) . ?
Cu1 O2 1.983(4) . ?
Cu1 N5 1.998(5) . ?
Cu1 N6 2.215(5) . ?
F1 C12 1.349(7) . ?
N1 C7 1.328(8) . ?
N1 N2 1.391(7) . ?
N2 C8 1.312(8) . ?
N3 C17 1.315(9) . ?
N3 N4 1.405(7) . ?
N4 C15 1.378(9) . ?
N4 C19 1.416(8) . ?
N5 C29 1.327(8) . ?
N5 C25 1.346(8) . ?
N6 C30 1.337(8) . ?
N6 C34 1.371(9) . ?
O1 C1 1.371(8) . ?
O1 H1 0.8400 . ?
O2 C7 1.272(8) . ?
O3 C15 1.299(8) . ?
C1 C2 1.381(10) . ?
C1 C6 1.414(9) . ?
C2 C3 1.419(10) . ?
C2 H2A 0.9500 . ?
C3 C4 1.363(10) . ?
C3 H3A 0.9500 . ?
C4 C5 1.379(10) . ?
C4 H4A 0.9500 . ?
C5 C6 1.422(10) . ?
C5 H5A 0.9500 . ?
C6 C7 1.473(9) . ?
C8 C16 1.423(9) . ?
C8 C9 1.475(9) . ?
C9 C14 1.385(9) . ?
C9 C10 1.418(9) . ?
C10 C11 1.372(9) . ?
C10 H10A 0.9500 . ?
C11 C12 1.353(9) . ?
C11 H11A 0.9500 . ?
C12 C13 1.396(10) . ?
C13 C14 1.381(10) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 C16 1.406(9) . ?
C16 C17 1.435(9) . ?
C17 C18 1.508(9) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C24 1.395(9) . ?
C19 C20 1.400(10) . ?
C20 C21 1.385(10) . ?
C20 H20A 0.9500 . ?
C21 C22 1.393(10) . ?
C21 H21A 0.9500 . ?
C22 C23 1.399(10) . ?
C22 H22A 0.9500 . ?
C23 C24 1.364(10) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?
C25 C26 1.363(9) . ?
C25 H25A 0.9500 . ?
C26 C27 1.369(10) . ?
C26 H26A 0.9500 . ?
C27 C28 1.386(10) . ?
C27 H27A 0.9500 . ?
C28 C29 1.372(9) . ?
C28 H28A 0.9500 . ?
C29 C30 1.503(9) . ?
C30 C31 1.379(9) . ?
C31 C32 1.399(10) . ?
C31 H31A 0.9500 . ?
C32 C33 1.369(11) . ?
C32 H32A 0.9500 . ?
C33 C34 1.363(10) . ?
C33 H33A 0.9500 . ?
C34 H34A 0.9500 . ?

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 N2 94.9(2) . . ?
O3 Cu1 O2 157.23(19) . . ?
N2 Cu1 O2 81.2(2) . . ?
O3 Cu1 N5 86.3(2) . . ?
N2 Cu1 N5 178.8(2) . . ?
O2 Cu1 N5 97.6(2) . . ?
O3 Cu1 N6 112.2(2) . . ?
N2 Cu1 N6 102.8(2) . . ?
O2 Cu1 N6 90.54(19) . . ?
N5 Cu1 N6 77.1(2) . . ?
C7 N1 N2 111.1(5) . . ?
C8 N2 N1 118.9(5) . . ?
C8 N2 Cu1 128.1(4) . . ?
N1 N2 Cu1 112.9(4) . . ?
C17 N3 N4 105.3(5) . . ?
C15 N4 N3 110.7(5) . . ?
C15 N4 C19 129.9(6) . . ?
N3 N4 C19 119.2(5) . . ?
C29 N5 C25 118.6(5) . . ?
C29 N5 Cu1 119.6(4) . . ?
C25 N5 Cu1 121.8(4) . . ?
C30 N6 C34 118.9(6) . . ?
C30 N6 Cu1 112.6(4) . . ?
C34 N6 Cu1 127.8(4) . . ?
C1 O1 H1 109.5 . . ?
C7 O2 Cu1 109.7(4) . . ?
C15 O3 Cu1 117.8(4) . . ?
O1 C1 C2 116.7(6) . . ?
O1 C1 C6 122.0(6) . . ?
C2 C1 C6 121.3(6) . . ?
C1 C2 C3 119.1(6) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 H2A 120.4 . . ?
C4 C3 C2 120.5(6) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 120.7(7) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 C6 121.0(6) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C1 C6 C5 117.3(6) . . ?
C1 C6 C7 123.3(6) . . ?
C5 C6 C7 119.4(6) . . ?
O2 C7 N1 124.5(6) . . ?
O2 C7 C6 119.9(6) . . ?
N1 C7 C6 115.6(6) . . ?
N2 C8 C16 119.7(6) . . ?
N2 C8 C9 122.0(6) . . ?
C16 C8 C9 118.3(6) . . ?
C14 C9 C10 118.3(6) . . ?
C14 C9 C8 120.9(6) . . ?
C10 C9 C8 120.5(6) . . ?
C11 C10 C9 120.7(6) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C12 C11 C10 119.6(7) . . ?
C12 C11 H11A 120.2 . . ?
C10 C11 H11A 120.2 . . ?
F1 C12 C11 120.0(6) . . ?
F1 C12 C13 118.2(6) . . ?
C11 C12 C13 121.8(6) . . ?
C14 C13 C12 118.7(6) . . ?
C14 C13 H13A 120.6 . . ?
C12 C13 H13A 120.6 . . ?
C13 C14 C9 120.9(6) . . ?
C13 C14 H14A 119.5 . . ?
C9 C14 H14A 119.5 . . ?
O3 C15 N4 121.0(6) . . ?
O3 C15 C16 131.8(6) . . ?
N4 C15 C16 107.2(6) . . ?
C15 C16 C8 123.9(6) . . ?
C15 C16 C17 104.1(6) . . ?
C8 C16 C17 132.0(6) . . ?
N3 C17 C16 112.7(6) . . ?
N3 C17 C18 118.0(6) . . ?
C16 C17 C18 129.2(6) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 119.6(6) . . ?
C24 C19 N4 118.7(6) . . ?
C20 C19 N4 121.7(6) . . ?
C21 C20 C19 118.8(6) . . ?
C21 C20 H20A 120.6 . . ?
C19 C20 H20A 120.6 . . ?
C20 C21 C22 121.8(6) . . ?
C20 C21 H21A 119.1 . . ?
C22 C21 H21A 119.1 . . ?
C21 C22 C23 118.2(6) . . ?
C21 C22 H22A 120.9 . . ?
C23 C22 H22A 120.9 . . ?
C24 C23 C22 120.7(7) . . ?
C24 C23 H23A 119.6 . . ?
C22 C23 H23A 119.6 . . ?
C23 C24 C19 120.8(7) . . ?
C23 C24 H24A 119.6 . . ?
C19 C24 H24A 119.6 . . ?
N5 C25 C26 123.3(6) . . ?
N5 C25 H25A 118.3 . . ?
C26 C25 H25A 118.3 . . ?
C25 C26 C27 118.2(6) . . ?
C25 C26 H26A 120.9 . . ?
C27 C26 H26A 120.9 . . ?
C26 C27 C28 118.9(6) . . ?
C26 C27 H27A 120.6 . . ?
C28 C27 H27A 120.6 . . ?
C29 C28 C27 119.9(7) . . ?
C29 C28 H28A 120.1 . . ?
C27 C28 H28A 120.1 . . ?
N5 C29 C28 121.2(6) . . ?
N5 C29 C30 115.9(5) . . ?
C28 C29 C30 122.8(6) . . ?
N6 C30 C31 122.2(6) . . ?
N6 C30 C29 114.1(5) . . ?
C31 C30 C29 123.8(6) . . ?
C30 C31 C32 118.6(7) . . ?
C30 C31 H31A 120.7 . . ?
C32 C31 H31A 120.7 . . ?
C33 C32 C31 118.8(7) . . ?
C33 C32 H32A 120.6 . . ?
C31 C32 H32A 120.6 . . ?
C34 C33 C32 120.4(7) . . ?
C34 C33 H33A 119.8 . . ?
C32 C33 H33A 119.8 . . ?
C33 C34 N6 121.0(7) . . ?
C33 C34 H34A 119.5 . . ?
N6 C34 H34A 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C8 169.3(5) . . . . ?
C7 N1 N2 Cu1 -6.1(6) . . . . ?
O3 Cu1 N2 C8 -10.2(5) . . . . ?
O2 Cu1 N2 C8 -167.6(6) . . . . ?
N5 Cu1 N2 C8 -166(11) . . . . ?
N6 Cu1 N2 C8 103.9(5) . . . . ?
O3 Cu1 N2 N1 164.7(4) . . . . ?
O2 Cu1 N2 N1 7.3(4) . . . . ?
N5 Cu1 N2 N1 8(11) . . . . ?
N6 Cu1 N2 N1 -81.2(4) . . . . ?
C17 N3 N4 C15 -1.9(7) . . . . ?
C17 N3 N4 C19 -177.2(5) . . . . ?
O3 Cu1 N5 C29 117.8(5) . . . . ?
N2 Cu1 N5 C29 -86(11) . . . . ?
O2 Cu1 N5 C29 -84.7(5) . . . . ?
N6 Cu1 N5 C29 4.1(4) . . . . ?
O3 Cu1 N5 C25 -58.6(5) . . . . ?
N2 Cu1 N5 C25 98(11) . . . . ?
O2 Cu1 N5 C25 98.8(5) . . . . ?
N6 Cu1 N5 C25 -172.4(5) . . . . ?
O3 Cu1 N6 C30 -88.1(4) . . . . ?
N2 Cu1 N6 C30 171.2(4) . . . . ?
O2 Cu1 N6 C30 90.1(4) . . . . ?
N5 Cu1 N6 C30 -7.6(4) . . . . ?
O3 Cu1 N6 C34 101.9(5) . . . . ?
N2 Cu1 N6 C34 1.1(6) . . . . ?
O2 Cu1 N6 C34 -80.0(5) . . . . ?
N5 Cu1 N6 C34 -177.6(6) . . . . ?
O3 Cu1 O2 C7 -88.6(6) . . . . ?
N2 Cu1 O2 C7 -7.1(4) . . . . ?
N5 Cu1 O2 C7 172.9(4) . . . . ?
N6 Cu1 O2 C7 95.8(4) . . . . ?
N2 Cu1 O3 C15 18.8(5) . . . . ?
O2 Cu1 O3 C15 97.5(6) . . . . ?
N5 Cu1 O3 C15 -161.7(5) . . . . ?
N6 Cu1 O3 C15 -87.2(5) . . . . ?
O1 C1 C2 C3 177.3(6) . . . . ?
C6 C1 C2 C3 -2.7(10) . . . . ?
C1 C2 C3 C4 1.3(11) . . . . ?
C2 C3 C4 C5 -0.1(11) . . . . ?
C3 C4 C5 C6 0.4(10) . . . . ?
O1 C1 C6 C5 -177.1(6) . . . . ?
C2 C1 C6 C5 2.9(9) . . . . ?
O1 C1 C6 C7 1.9(10) . . . . ?
C2 C1 C6 C7 -178.1(6) . . . . ?
C4 C5 C6 C1 -1.7(9) . . . . ?
C4 C5 C6 C7 179.2(6) . . . . ?
Cu1 O2 C7 N1 6.3(7) . . . . ?
Cu1 O2 C7 C6 -175.3(4) . . . . ?
N2 N1 C7 O2 -0.3(8) . . . . ?
N2 N1 C7 C6 -178.8(5) . . . . ?
C1 C6 C7 O2 173.2(6) . . . . ?
C5 C6 C7 O2 -7.8(9) . . . . ?
C1 C6 C7 N1 -8.2(9) . . . . ?
C5 C6 C7 N1 170.8(6) . . . . ?
N1 N2 C8 C16 -178.9(5) . . . . ?
Cu1 N2 C8 C16 -4.3(8) . . . . ?
N1 N2 C8 C9 0.9(9) . . . . ?
Cu1 N2 C8 C9 175.5(4) . . . . ?
N2 C8 C9 C14 -118.4(7) . . . . ?
C16 C8 C9 C14 61.5(8) . . . . ?
N2 C8 C9 C10 68.3(8) . . . . ?
C16 C8 C9 C10 -111.9(7) . . . . ?
C14 C9 C10 C11 -1.6(10) . . . . ?
C8 C9 C10 C11 171.9(6) . . . . ?
C9 C10 C11 C12 1.7(11) . . . . ?
C10 C11 C12 F1 179.9(6) . . . . ?
C10 C11 C12 C13 0.1(11) . . . . ?
F1 C12 C13 C14 178.3(6) . . . . ?
C11 C12 C13 C14 -1.9(10) . . . . ?
C12 C13 C14 C9 1.9(10) . . . . ?
C10 C9 C14 C13 -0.2(10) . . . . ?
C8 C9 C14 C13 -173.7(6) . . . . ?
Cu1 O3 C15 N4 160.8(5) . . . . ?
Cu1 O3 C15 C16 -16.5(10) . . . . ?
N3 N4 C15 O3 -175.3(6) . . . . ?
C19 N4 C15 O3 -0.5(10) . . . . ?
N3 N4 C15 C16 2.6(7) . . . . ?
C19 N4 C15 C16 177.4(6) . . . . ?
O3 C15 C16 C8 -2.6(12) . . . . ?
N4 C15 C16 C8 179.8(6) . . . . ?
O3 C15 C16 C17 175.3(7) . . . . ?
N4 C15 C16 C17 -2.2(7) . . . . ?
N2 C8 C16 C15 14.3(10) . . . . ?
C9 C8 C16 C15 -165.5(6) . . . . ?
N2 C8 C16 C17 -163.1(7) . . . . ?
C9 C8 C16 C17 17.1(10) . . . . ?
N4 N3 C17 C16 0.4(7) . . . . ?
N4 N3 C17 C18 176.9(6) . . . . ?
C15 C16 C17 N3 1.2(7) . . . . ?
C8 C16 C17 N3 178.9(7) . . . . ?
C15 C16 C17 C18 -174.8(7) . . . . ?
C8 C16 C17 C18 2.9(12) . . . . ?
C15 N4 C19 C24 -161.0(7) . . . . ?
N3 N4 C19 C24 13.4(9) . . . . ?
C15 N4 C19 C20 18.6(10) . . . . ?
N3 N4 C19 C20 -167.1(6) . . . . ?
C24 C19 C20 C21 -0.2(10) . . . . ?
N4 C19 C20 C21 -179.7(6) . . . . ?
C19 C20 C21 C22 -1.4(10) . . . . ?
C20 C21 C22 C23 0.9(11) . . . . ?
C21 C22 C23 C24 1.1(12) . . . . ?
C22 C23 C24 C19 -2.6(12) . . . . ?
C20 C19 C24 C23 2.2(11) . . . . ?
N4 C19 C24 C23 -178.3(7) . . . . ?
C29 N5 C25 C26 0.6(10) . . . . ?
Cu1 N5 C25 C26 177.0(5) . . . . ?
N5 C25 C26 C27 0.0(10) . . . . ?
C25 C26 C27 C28 -0.3(10) . . . . ?
C26 C27 C28 C29 0.2(10) . . . . ?
C25 N5 C29 C28 -0.7(9) . . . . ?
Cu1 N5 C29 C28 -177.3(5) . . . . ?
C25 N5 C29 C30 176.3(6) . . . . ?
Cu1 N5 C29 C30 -0.3(7) . . . . ?
C27 C28 C29 N5 0.4(10) . . . . ?
C27 C28 C29 C30 -176.4(6) . . . . ?
C34 N6 C30 C31 1.4(9) . . . . ?
Cu1 N6 C30 C31 -169.7(5) . . . . ?
C34 N6 C30 C29 -179.5(5) . . . . ?
Cu1 N6 C30 C29 9.4(6) . . . . ?
N5 C29 C30 N6 -6.6(8) . . . . ?
C28 C29 C30 N6 170.3(6) . . . . ?
N5 C29 C30 C31 172.5(6) . . . . ?
C28 C29 C30 C31 -10.6(10) . . . . ?
N6 C30 C31 C32 -2.4(10) . . . . ?
C29 C30 C31 C32 178.6(6) . . . . ?
C30 C31 C32 C33 2.3(10) . . . . ?
C31 C32 C33 C34 -1.2(11) . . . . ?
C32 C33 C34 N6 0.2(10) . . . . ?
C30 N6 C34 C33 -0.3(9) . . . . ?
Cu1 N6 C34 C33 169.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.940
_refine_diff_density_min         -1.228
_refine_diff_density_rms         0.122
####################################################################### 
# 
# 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_qq
_database_code_depnum_ccdc_archive 'CCDC 1842070'
_audit_update_record             
;
2018-05-08 deposited with the CCDC.
2019-01-07 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            'C39 H26 Cl3 Cu F N8 O3'
_chemical_formula_weight         843.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3640 0.7020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9650 0.5890 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0730 0.0530 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 '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                   9.6433(6)
_cell_length_b                   13.9637(10)
_cell_length_c                   14.9574(10)
_cell_angle_alpha                66.063(7)
_cell_angle_beta                 82.774(5)
_cell_angle_gamma                86.174(6)
_cell_volume                     1826.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6268
_cell_measurement_theta_min      4.6120
_cell_measurement_theta_max      73.2910

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             858
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    3.341
_shelx_estimated_absorpt_T_min   0.527
_shelx_estimated_absorpt_T_max   0.555
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  bruker-CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9793
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.252
_diffrn_reflns_theta_max         66.097
_diffrn_reflns_theta_full        66.097
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             6300
_reflns_number_gt                5806
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1290P)²+1.0551P] 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         6300
_refine_ls_number_parameters     498
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1724
_refine_ls_wR_factor_gt          0.1671
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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 0.00189(4) 0.10534(3) 0.66537(3) 0.01728(16) Uani 1 1 d . . . . .
F1 F -0.1342(2) -0.42604(16) 1.19177(14) 0.0413(5) Uani 1 1 d . . . . .
O1 O 0.1041(2) 0.02384(15) 0.59983(14) 0.0212(4) Uani 1 1 d . . . . .
O2 O -0.1373(2) 0.17309(15) 0.72821(14) 0.0210(4) Uani 1 1 d . . . . .
O3 O -0.3031(2) -0.02557(18) 1.01217(16) 0.0326(5) Uani 1 1 d . . . . .
H3 H -0.2393 -0.0383 0.9746 0.049 Uiso 1 1 calc R U . . .
N1 N 0.2446(2) -0.12337(19) 0.61667(18) 0.0208(5) Uani 1 1 d . . . . .
N2 N 0.2744(3) -0.2213(2) 0.6885(2) 0.0261(5) Uani 1 1 d . . . . .
N3 N -0.0453(2) -0.01515(19) 0.78922(17) 0.0193(5) Uani 1 1 d . . . . .
N4 N -0.1435(2) 0.00844(18) 0.85378(17) 0.0201(5) Uani 1 1 d . . . . .
N5 N 0.1773(2) 0.18024(18) 0.69645(17) 0.0185(5) Uani 1 1 d . . . . .
N6 N 0.0265(2) 0.24104(18) 0.54163(17) 0.0176(5) Uani 1 1 d . . . . .
N7 N 0.3770(2) 0.52298(19) 0.57223(18) 0.0221(5) Uani 1 1 d . . . . .
N8 N 0.2262(2) 0.58469(19) 0.40848(18) 0.0219(5) Uani 1 1 d . . . . .
C0AA C 0.2582(3) -0.0285(2) 0.4385(2) 0.0260(6) Uani 1 1 d . . . . .
H0AA H 0.1634 -0.0064 0.4442 0.031 Uiso 1 1 calc R U . . .
C2 C 0.3351(4) 0.0012(3) 0.3463(2) 0.0335(7) Uani 1 1 d . . . . .
H2 H 0.2924 0.0434 0.2888 0.040 Uiso 1 1 calc R U . . .
C3 C 0.4745(4) -0.0309(3) 0.3383(2) 0.0349(7) Uani 1 1 d . . . . .
H3A H 0.5268 -0.0104 0.2755 0.042 Uiso 1 1 calc R U . . .
C4 C 0.5363(3) -0.0928(3) 0.4222(3) 0.0318(7) Uani 1 1 d . . . . .
H4A H 0.6313 -0.1147 0.4168 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4601(3) -0.1231(2) 0.5141(2) 0.0250(6) Uani 1 1 d . . . . .
H5 H 0.5026 -0.1660 0.5715 0.030 Uiso 1 1 calc R U . . .
C6 C 0.3215(3) -0.0906(2) 0.5219(2) 0.0209(6) Uani 1 1 d . . . . .
C7 C 0.1448(3) -0.0703(2) 0.6525(2) 0.0184(5) Uani 1 1 d . . . . .
C8 C 0.1062(3) -0.1376(2) 0.7519(2) 0.0215(6) Uani 1 1 d . . . . .
C9 C 0.1914(3) -0.2296(2) 0.7678(2) 0.0259(6) Uani 1 1 d . . . . .
C10 C 0.1986(4) -0.3288(3) 0.8587(3) 0.0407(9) Uani 1 1 d . . . . .
H10A H 0.2131 -0.3117 0.9142 0.061 Uiso 1 1 calc R U . . .
H10B H 0.2765 -0.3730 0.8478 0.061 Uiso 1 1 calc R U . . .
H10C H 0.1108 -0.3666 0.8735 0.061 Uiso 1 1 calc R U . . .
C11 C 0.0059(3) -0.1114(2) 0.8183(2) 0.0189(5) Uani 1 1 d . . . . .
C12 C -0.0374(3) -0.1916(2) 0.9186(2) 0.0202(6) Uani 1 1 d . . . . .
C13 C -0.1253(4) -0.2704(3) 0.9305(2) 0.0318(7) Uani 1 1 d . . . . .
H13 H -0.1628 -0.2709 0.8750 0.038 Uiso 1 1 calc R U . . .
C14 C -0.1602(4) -0.3498(3) 1.0232(3) 0.0371(8) Uani 1 1 d . . . . .
H14 H -0.2211 -0.4042 1.0317 0.045 Uiso 1 1 calc R U . . .
C15 C -0.1041(3) -0.3468(2) 1.1014(2) 0.0281(7) Uani 1 1 d . . . . .
C16 C -0.0189(3) -0.2690(3) 1.0929(2) 0.0333(7) Uani 1 1 d . . . . .
H16 H 0.0172 -0.2688 1.1491 0.040 Uiso 1 1 calc R U . . .
C17 C 0.0141(3) -0.1900(3) 1.0007(2) 0.0294(7) Uani 1 1 d . . . . .
H17 H 0.0722 -0.1345 0.9936 0.035 Uiso 1 1 calc R U . . .
C18 C -0.1825(3) 0.1079(2) 0.8156(2) 0.0186(6) Uani 1 1 d . . . . .
C19 C -0.2811(3) 0.1459(2) 0.8791(2) 0.0205(6) Uani 1 1 d . . . . .
C20 C -0.3169(3) 0.2530(2) 0.8462(2) 0.0246(6) Uani 1 1 d . . . . .
H20 H -0.2802 0.3000 0.7825 0.029 Uiso 1 1 calc R U . . .
C21 C -0.4046(3) 0.2905(3) 0.9049(3) 0.0321(7) Uani 1 1 d . . . . .
H21 H -0.4267 0.3633 0.8822 0.038 Uiso 1 1 calc R U . . .
C22 C -0.4608(4) 0.2223(3) 0.9975(3) 0.0368(8) Uani 1 1 d . . . . .
H22 H -0.5223 0.2483 1.0376 0.044 Uiso 1 1 calc R U . . .
C23 C -0.4273(4) 0.1168(3) 1.0313(2) 0.0352(8) Uani 1 1 d . . . . .
H23 H -0.4665 0.0704 1.0946 0.042 Uiso 1 1 calc R U . . .
C24 C -0.3369(3) 0.0778(2) 0.9736(2) 0.0253(6) Uani 1 1 d . . . . .
C25 C 0.2511(3) 0.1489(2) 0.7729(2) 0.0203(6) Uani 1 1 d . . . . .
H25 H 0.2389 0.0794 0.8213 0.024 Uiso 1 1 calc R U . . .
C26 C 0.3458(3) 0.2124(2) 0.7862(2) 0.0238(6) Uani 1 1 d . . . . .
H26 H 0.3973 0.1862 0.8418 0.029 Uiso 1 1 calc R U . . .
C27 C 0.3628(3) 0.3128(2) 0.7177(2) 0.0220(6) Uani 1 1 d . . . . .
H27 H 0.4264 0.3575 0.7249 0.026 Uiso 1 1 calc R U . . .
C28 C 0.2848(3) 0.3495(2) 0.63590(19) 0.0171(5) Uani 1 1 d . . . . .
C29 C 0.1946(3) 0.2798(2) 0.62852(19) 0.0159(5) Uani 1 1 d . . . . .
C30 C 0.1128(3) 0.3120(2) 0.54444(19) 0.0168(5) Uani 1 1 d . . . . .
C31 C 0.1262(3) 0.4130(2) 0.47057(19) 0.0174(5) Uani 1 1 d . . . . .
C32 C 0.0458(3) 0.4404(2) 0.3908(2) 0.0211(6) Uani 1 1 d . . . . .
H32 H 0.0507 0.5088 0.3398 0.025 Uiso 1 1 calc R U . . .
C33 C -0.0395(3) 0.3674(2) 0.3879(2) 0.0233(6) Uani 1 1 d . . . . .
H33 H -0.0931 0.3840 0.3342 0.028 Uiso 1 1 calc R U . . .
C34 C -0.0462(3) 0.2685(2) 0.4647(2) 0.0221(6) Uani 1 1 d . . . . .
H34 H -0.1055 0.2182 0.4620 0.027 Uiso 1 1 calc R U . . .
C35 C 0.3814(3) 0.6189(2) 0.5035(2) 0.0244(6) Uani 1 1 d . . . . .
H35 H 0.4374 0.6689 0.5095 0.029 Uiso 1 1 calc R U . . .
C36 C 0.3059(3) 0.6496(2) 0.4215(2) 0.0241(6) Uani 1 1 d . . . . .
H36 H 0.3126 0.7198 0.3739 0.029 Uiso 1 1 calc R U . . .
C37 C 0.4205(4) 0.3433(3) 0.2409(3) 0.0363(8) Uani 1 1 d . . . . .
H37 H 0.5011 0.2929 0.2467 0.044 Uiso 1 1 calc R U . . .
C47 C 0.2183(3) 0.4869(2) 0.47900(19) 0.0170(5) Uani 1 1 d . . . . .
C74 C 0.2947(3) 0.4553(2) 0.5614(2) 0.0179(5) Uani 1 1 d . . . . .
Cl1 Cl 0.45626(12) 0.42589(8) 0.29641(7) 0.0498(3) Uani 1 1 d . . . . .
Cl2 Cl 0.40563(12) 0.41667(8) 0.11430(7) 0.0530(3) Uani 1 1 d . . . . .
Cl3 Cl 0.26959(10) 0.27067(8) 0.30037(8) 0.0497(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9340(19) . ?
Cu1 O2 1.9529(19) . ?
Cu1 N3 1.957(2) . ?
Cu1 N6 2.044(2) . ?
Cu1 N5 2.236(2) . ?
Cu1 C18 2.695(3) . ?
F1 C15 1.366(4) . ?
O1 C7 1.293(3) . ?
O2 C18 1.293(3) . ?
O3 C24 1.354(4) . ?
O3 H3 0.8400 . ?
N1 C7 1.363(4) . ?
N1 N2 1.393(3) . ?
N1 C6 1.422(4) . ?
N2 C9 1.312(4) . ?
N3 C11 1.316(4) . ?
N3 N4 1.387(3) . ?
N4 C18 1.318(4) . ?
N5 C25 1.328(4) . ?
N5 C29 1.355(4) . ?
N6 C34 1.332(4) . ?
N6 C30 1.352(4) . ?
N7 C35 1.316(4) . ?
N7 C74 1.344(4) . ?
N8 C36 1.313(4) . ?
N8 C47 1.344(4) . ?
C0AA C6 1.387(4) . ?
C0AA C2 1.394(5) . ?
C0AA H0AA 0.9500 . ?
C2 C3 1.395(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.387(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.388(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.416(4) . ?
C8 C9 1.429(4) . ?
C8 C11 1.436(4) . ?
C9 C10 1.502(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.491(4) . ?
C12 C13 1.374(4) . ?
C12 C17 1.390(4) . ?
C13 C14 1.396(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.364(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.361(5) . ?
C16 C17 1.386(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.482(4) . ?
C19 C20 1.406(4) . ?
C19 C24 1.407(4) . ?
C20 C21 1.374(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.389(5) . ?
C23 H23 0.9500 . ?
C25 C26 1.399(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.366(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.413(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.393(4) . ?
C28 C74 1.446(4) . ?
C29 C30 1.466(3) . ?
C30 C31 1.397(4) . ?
C31 C32 1.412(4) . ?
C31 C47 1.459(4) . ?
C32 C33 1.369(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.392(4) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C36 1.405(4) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 Cl1 1.744(3) . ?
C37 Cl3 1.754(4) . ?
C37 Cl2 1.770(4) . ?
C37 H37 1.0000 . ?
C47 C74 1.414(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
O1 Cu1 O2 167.32(9) . . ?
O1 Cu1 N3 94.95(9) . . ?
O2 Cu1 N3 81.19(9) . . ?
O1 Cu1 N6 92.31(9) . . ?
O2 Cu1 N6 90.97(9) . . ?
N3 Cu1 N6 171.93(9) . . ?
O1 Cu1 N5 100.94(8) . . ?
O2 Cu1 N5 91.73(8) . . ?
N3 Cu1 N5 103.94(9) . . ?
N6 Cu1 N5 78.07(9) . . ?
O1 Cu1 C18 147.85(9) . . ?
O2 Cu1 C18 26.67(8) . . ?
N3 Cu1 C18 54.54(9) . . ?
N6 Cu1 C18 117.64(9) . . ?
N5 Cu1 C18 96.78(8) . . ?
C7 O1 Cu1 118.78(17) . . ?
C18 O2 Cu1 110.64(16) . . ?
C24 O3 H3 109.5 . . ?
C7 N1 N2 111.5(2) . . ?
C7 N1 C6 129.4(2) . . ?
N2 N1 C6 119.0(2) . . ?
C9 N2 N1 105.9(2) . . ?
C11 N3 N4 118.0(2) . . ?
C11 N3 Cu1 128.7(2) . . ?
N4 N3 Cu1 113.32(17) . . ?
C18 N4 N3 111.0(2) . . ?
C25 N5 C29 117.6(2) . . ?
C25 N5 Cu1 131.5(2) . . ?
C29 N5 Cu1 110.42(17) . . ?
C34 N6 C30 118.5(2) . . ?
C34 N6 Cu1 125.09(19) . . ?
C30 N6 Cu1 116.04(17) . . ?
C35 N7 C74 116.9(2) . . ?
C36 N8 C47 116.4(2) . . ?
C6 C0AA C2 119.4(3) . . ?
C6 C0AA H0AA 120.3 . . ?
C2 C0AA H0AA 120.3 . . ?
C0AA C2 C3 120.2(3) . . ?
C0AA C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C0AA C6 C5 120.5(3) . . ?
C0AA C6 N1 120.4(2) . . ?
C5 C6 N1 119.0(3) . . ?
O1 C7 N1 122.4(2) . . ?
O1 C7 C8 131.4(3) . . ?
N1 C7 C8 106.2(2) . . ?
C7 C8 C9 104.7(2) . . ?
C7 C8 C11 124.7(2) . . ?
C9 C8 C11 130.5(3) . . ?
N2 C9 C8 111.7(3) . . ?
N2 C9 C10 118.3(3) . . ?
C8 C9 C10 130.0(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 C8 118.7(3) . . ?
N3 C11 C12 120.9(3) . . ?
C8 C11 C12 120.4(2) . . ?
C13 C12 C17 119.2(3) . . ?
C13 C12 C11 120.1(3) . . ?
C17 C12 C11 120.7(3) . . ?
C12 C13 C14 120.9(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 118.0(3) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C16 C15 C14 122.9(3) . . ?
C16 C15 F1 118.8(3) . . ?
C14 C15 F1 118.3(3) . . ?
C15 C16 C17 118.7(3) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C16 C17 C12 120.3(3) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
O2 C18 N4 123.7(2) . . ?
O2 C18 C19 119.3(2) . . ?
N4 C18 C19 116.9(2) . . ?
O2 C18 Cu1 42.69(12) . . ?
N4 C18 Cu1 81.10(16) . . ?
C19 C18 Cu1 161.6(2) . . ?
C20 C19 C24 118.4(3) . . ?
C20 C19 C18 119.8(3) . . ?
C24 C19 C18 121.7(3) . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 120.5(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
O3 C24 C23 118.0(3) . . ?
O3 C24 C19 122.0(3) . . ?
C23 C24 C19 119.9(3) . . ?
N5 C25 C26 123.7(3) . . ?
N5 C25 H25 118.2 . . ?
C26 C25 H25 118.2 . . ?
C27 C26 C25 118.6(3) . . ?
C27 C26 H26 120.7 . . ?
C25 C26 H26 120.7 . . ?
C26 C27 C28 119.4(3) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C29 C28 C27 117.7(3) . . ?
C29 C28 C74 119.6(2) . . ?
C27 C28 C74 122.7(2) . . ?
N5 C29 C28 123.1(2) . . ?
N5 C29 C30 116.4(2) . . ?
C28 C29 C30 120.5(2) . . ?
N6 C30 C31 122.3(2) . . ?
N6 C30 C29 117.8(2) . . ?
C31 C30 C29 119.8(2) . . ?
C30 C31 C32 117.9(3) . . ?
C30 C31 C47 119.8(2) . . ?
C32 C31 C47 122.3(2) . . ?
C33 C32 C31 119.3(3) . . ?
C33 C32 H32 120.4 . . ?
C31 C32 H32 120.4 . . ?
C32 C33 C34 119.0(3) . . ?
C32 C33 H33 120.5 . . ?
C34 C33 H33 120.5 . . ?
N6 C34 C33 123.1(3) . . ?
N6 C34 H34 118.5 . . ?
C33 C34 H34 118.5 . . ?
N7 C35 C36 122.1(3) . . ?
N7 C35 H35 118.9 . . ?
C36 C35 H35 118.9 . . ?
N8 C36 C35 122.2(3) . . ?
N8 C36 H36 118.9 . . ?
C35 C36 H36 118.9 . . ?
Cl1 C37 Cl3 111.2(2) . . ?
Cl1 C37 Cl2 110.2(2) . . ?
Cl3 C37 Cl2 111.23(18) . . ?
Cl1 C37 H37 108.0 . . ?
Cl3 C37 H37 108.0 . . ?
Cl2 C37 H37 108.0 . . ?
N8 C47 C74 121.6(3) . . ?
N8 C47 C31 118.7(2) . . ?
C74 C47 C31 119.7(2) . . ?
N7 C74 C47 120.7(3) . . ?
N7 C74 C28 118.8(2) . . ?
C47 C74 C28 120.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C9 1.1(3) . . . . ?
C6 N1 N2 C9 178.5(2) . . . . ?
C11 N3 N4 C18 178.4(2) . . . . ?
Cu1 N3 N4 C18 0.2(3) . . . . ?
C6 C0AA C2 C3 -0.3(5) . . . . ?
C0AA C2 C3 C4 0.3(5) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C2 C0AA C6 C5 0.0(4) . . . . ?
C2 C0AA C6 N1 -179.0(3) . . . . ?
C4 C5 C6 C0AA 0.4(4) . . . . ?
C4 C5 C6 N1 179.3(3) . . . . ?
C7 N1 C6 C0AA -36.9(4) . . . . ?
N2 N1 C6 C0AA 146.3(3) . . . . ?
C7 N1 C6 C5 144.2(3) . . . . ?
N2 N1 C6 C5 -32.7(4) . . . . ?
Cu1 O1 C7 N1 -163.5(2) . . . . ?
Cu1 O1 C7 C8 14.5(4) . . . . ?
N2 N1 C7 O1 177.5(2) . . . . ?
C6 N1 C7 O1 0.4(4) . . . . ?
N2 N1 C7 C8 -0.9(3) . . . . ?
C6 N1 C7 C8 -178.0(3) . . . . ?
O1 C7 C8 C9 -177.9(3) . . . . ?
N1 C7 C8 C9 0.4(3) . . . . ?
O1 C7 C8 C11 0.0(5) . . . . ?
N1 C7 C8 C11 178.2(3) . . . . ?
N1 N2 C9 C8 -0.9(3) . . . . ?
N1 N2 C9 C10 179.4(3) . . . . ?
C7 C8 C9 N2 0.3(3) . . . . ?
C11 C8 C9 N2 -177.4(3) . . . . ?
C7 C8 C9 C10 180.0(3) . . . . ?
C11 C8 C9 C10 2.3(6) . . . . ?
N4 N3 C11 C8 179.1(2) . . . . ?
Cu1 N3 C11 C8 -2.9(4) . . . . ?
N4 N3 C11 C12 -1.7(4) . . . . ?
Cu1 N3 C11 C12 176.27(18) . . . . ?
C7 C8 C11 N3 -6.7(4) . . . . ?
C9 C8 C11 N3 170.6(3) . . . . ?
C7 C8 C11 C12 174.1(3) . . . . ?
C9 C8 C11 C12 -8.6(5) . . . . ?
N3 C11 C12 C13 106.7(3) . . . . ?
C8 C11 C12 C13 -74.1(3) . . . . ?
N3 C11 C12 C17 -75.6(4) . . . . ?
C8 C11 C12 C17 103.6(3) . . . . ?
C17 C12 C13 C14 -1.7(5) . . . . ?
C11 C12 C13 C14 176.1(3) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
C13 C14 C15 C16 1.6(5) . . . . ?
C13 C14 C15 F1 -178.0(3) . . . . ?
C14 C15 C16 C17 -1.0(5) . . . . ?
F1 C15 C16 C17 178.5(3) . . . . ?
C15 C16 C17 C12 -1.0(5) . . . . ?
C13 C12 C17 C16 2.3(5) . . . . ?
C11 C12 C17 C16 -175.5(3) . . . . ?
Cu1 O2 C18 N4 -2.9(3) . . . . ?
Cu1 O2 C18 C19 175.32(18) . . . . ?
N3 N4 C18 O2 1.9(4) . . . . ?
N3 N4 C18 C19 -176.4(2) . . . . ?
N3 N4 C18 Cu1 -0.12(18) . . . . ?
O2 C18 C19 C20 -4.1(4) . . . . ?
N4 C18 C19 C20 174.3(2) . . . . ?
Cu1 C18 C19 C20 6.0(7) . . . . ?
O2 C18 C19 C24 178.1(2) . . . . ?
N4 C18 C19 C24 -3.5(4) . . . . ?
Cu1 C18 C19 C24 -171.8(4) . . . . ?
C24 C19 C20 C21 0.0(4) . . . . ?
C18 C19 C20 C21 -177.9(3) . . . . ?
C19 C20 C21 C22 -1.0(5) . . . . ?
C20 C21 C22 C23 0.9(5) . . . . ?
C21 C22 C23 C24 0.4(5) . . . . ?
C22 C23 C24 O3 177.3(3) . . . . ?
C22 C23 C24 C19 -1.4(5) . . . . ?
C20 C19 C24 O3 -177.4(3) . . . . ?
C18 C19 C24 O3 0.5(4) . . . . ?
C20 C19 C24 C23 1.2(4) . . . . ?
C18 C19 C24 C23 179.1(3) . . . . ?
C29 N5 C25 C26 -0.7(4) . . . . ?
Cu1 N5 C25 C26 -171.2(2) . . . . ?
N5 C25 C26 C27 0.8(4) . . . . ?
C25 C26 C27 C28 0.0(4) . . . . ?
C26 C27 C28 C29 -0.9(4) . . . . ?
C26 C27 C28 C74 178.6(3) . . . . ?
C25 N5 C29 C28 -0.3(4) . . . . ?
Cu1 N5 C29 C28 172.12(19) . . . . ?
C25 N5 C29 C30 179.4(2) . . . . ?
Cu1 N5 C29 C30 -8.2(3) . . . . ?
C27 C28 C29 N5 1.0(4) . . . . ?
C74 C28 C29 N5 -178.5(2) . . . . ?
C27 C28 C29 C30 -178.7(2) . . . . ?
C74 C28 C29 C30 1.8(4) . . . . ?
C34 N6 C30 C31 1.2(4) . . . . ?
Cu1 N6 C30 C31 -171.88(19) . . . . ?
C34 N6 C30 C29 -178.6(2) . . . . ?
Cu1 N6 C30 C29 8.3(3) . . . . ?
N5 C29 C30 N6 0.6(3) . . . . ?
C28 C29 C30 N6 -179.7(2) . . . . ?
N5 C29 C30 C31 -179.1(2) . . . . ?
C28 C29 C30 C31 0.6(4) . . . . ?
N6 C30 C31 C32 0.0(4) . . . . ?
C29 C30 C31 C32 179.8(2) . . . . ?
N6 C30 C31 C47 178.4(2) . . . . ?
C29 C30 C31 C47 -1.9(4) . . . . ?
C30 C31 C32 C33 -1.2(4) . . . . ?
C47 C31 C32 C33 -179.5(2) . . . . ?
C31 C32 C33 C34 1.1(4) . . . . ?
C30 N6 C34 C33 -1.2(4) . . . . ?
Cu1 N6 C34 C33 171.1(2) . . . . ?
C32 C33 C34 N6 0.1(4) . . . . ?
C74 N7 C35 C36 -1.0(4) . . . . ?
C47 N8 C36 C35 1.2(4) . . . . ?
N7 C35 C36 N8 0.1(5) . . . . ?
C36 N8 C47 C74 -1.6(4) . . . . ?
C36 N8 C47 C31 177.2(2) . . . . ?
C30 C31 C47 N8 -178.0(2) . . . . ?
C32 C31 C47 N8 0.2(4) . . . . ?
C30 C31 C47 C74 0.8(4) . . . . ?
C32 C31 C47 C74 179.0(2) . . . . ?
C35 N7 C74 C47 0.6(4) . . . . ?
C35 N7 C74 C28 -179.1(2) . . . . ?
N8 C47 C74 N7 0.7(4) . . . . ?
C31 C47 C74 N7 -178.0(2) . . . . ?
N8 C47 C74 C28 -179.6(2) . . . . ?
C31 C47 C74 C28 1.6(4) . . . . ?
C29 C28 C74 N7 176.7(2) . . . . ?
C27 C28 C74 N7 -2.7(4) . . . . ?
C29 C28 C74 C47 -2.9(4) . . . . ?
C27 C28 C74 C47 177.6(2) . . . . ?

_refine_diff_density_max         0.802
_refine_diff_density_min         -1.086
_refine_diff_density_rms         0.107



