# 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 2018

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1844910'
_audit_update_record             
;
2018-05-23 deposited with the CCDC.
2018-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
chlorido-(1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylato-O,O')-(di(2-pyridyl)amine-N,N')-copper(II)-dihydrate
_chemical_name_common            
;
chlorido-(pefloxacinato-O,O')-(di(2-pyridyl)amine-N,N')-copper(II)-dihydrate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H28 Cl Cu F N6 O3, 2(H2 O)'
_chemical_formula_sum            'C27 H32 Cl Cu F N6 O5'
_chemical_formula_weight         638.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.0898(3)
_cell_length_b                   11.8193(4)
_cell_length_c                   15.4407(5)
_cell_angle_alpha                99.797(3)
_cell_angle_beta                 91.722(2)
_cell_angle_gamma                92.749(3)
_cell_volume                     1452.07(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6053
_cell_measurement_theta_min      3.2610
_cell_measurement_theta_max      29.2450

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             662
_exptl_absorpt_coefficient_mu    0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6148
_exptl_absorpt_correction_T_max  0.8408
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'

_exptl_special_details           
;
386 frames in 7 runs of ω scans. Crystal-detector distance = 55.0 mm. 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14012
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6654
_reflns_number_gt                5217
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0452P)²+0.5067P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6654
_refine_ls_number_parameters     387
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.74696(3) 0.86314(2) 0.294467(17) 0.04178(10) Uani 1 1 d . . .
Cl1 Cl 1.03666(7) 0.96309(5) 0.30598(4) 0.04827(15) Uani 1 1 d . . .
F1 F 0.5523(2) 1.28440(12) 0.07543(10) 0.0615(4) Uani 1 1 d . . .
N1 N 0.6592(2) 0.99012(17) 0.38228(12) 0.0432(4) Uani 1 1 d . . .
N2 N 0.7877(3) 0.77496(18) 0.39319(13) 0.0498(5) Uani 1 1 d . . .
N3 N 0.8202(3) 0.94334(18) 0.49944(12) 0.0454(5) Uani 1 1 d D . .
H3A H 0.861(3) 0.971(2) 0.5514(12) 0.055 Uiso 1 1 d D . .
N4 N 0.8427(2) 0.88121(15) -0.05071(11) 0.0354(4) Uani 1 1 d . . .
N5 N 0.6852(2) 1.26201(15) -0.09126(13) 0.0433(4) Uani 1 1 d . . .
N6 N 0.6956(3) 1.43807(18) -0.19858(16) 0.0607(6) Uani 1 1 d . . .
O1 O 0.7774(2) 0.72534(14) 0.21201(10) 0.0520(4) Uani 1 1 d . . .
O2 O 0.8255(2) 0.61559(14) 0.08566(11) 0.0548(4) Uani 1 1 d . . .
O3 O 0.6679(2) 0.93806(14) 0.19874(10) 0.0468(4) Uani 1 1 d . . .
C1 C 0.7978(3) 0.7097(2) 0.12889(15) 0.0413(5) Uani 1 1 d . . .
C2 C 0.7883(3) 0.81108(19) 0.08330(14) 0.0376(5) Uani 1 1 d . . .
C3 C 0.8442(3) 0.79916(19) -0.00077(14) 0.0377(5) Uani 1 1 d . . .
H3 H 0.8861 0.7292 -0.0246 0.045 Uiso 1 1 calc R . .
C4 C 0.7207(3) 0.91582(19) 0.12076(13) 0.0363(5) Uani 1 1 d . . .
C5 C 0.7122(2) 1.00222(19) 0.06557(14) 0.0355(5) Uani 1 1 d . . .
C6 C 0.7743(2) 0.98629(18) -0.01973(13) 0.0338(4) Uani 1 1 d . . .
C7 C 0.6413(3) 1.1078(2) 0.09540(15) 0.0408(5) Uani 1 1 d . . .
H7 H 0.5992 1.1215 0.1514 0.049 Uiso 1 1 calc R . .
C8 C 0.6335(3) 1.1887(2) 0.04482(15) 0.0420(5) Uani 1 1 d . . .
C9 C 0.7002(3) 1.17815(18) -0.04043(14) 0.0375(5) Uani 1 1 d . . .
C10 C 0.7710(3) 1.07328(18) -0.07017(14) 0.0360(5) Uani 1 1 d . . .
H10 H 0.8172 1.0615 -0.1252 0.043 Uiso 1 1 calc R . .
C11 C 0.9042(3) 0.85450(19) -0.14071(14) 0.0409(5) Uani 1 1 d . . .
H11A H 0.9774 0.7914 -0.1440 0.049 Uiso 1 1 calc R . .
H11B H 0.9677 0.9209 -0.1536 0.049 Uiso 1 1 calc R . .
C12 C 0.7642(3) 0.8223(2) -0.20860(16) 0.0580(7) Uani 1 1 d . . .
H12A H 0.6908 0.7650 -0.1908 0.087 Uiso 1 1 calc R . .
H12B H 0.8084 0.7923 -0.2644 0.087 Uiso 1 1 calc R . .
H12C H 0.7044 0.8892 -0.2138 0.087 Uiso 1 1 calc R . .
C13 C 0.7231(3) 1.38429(19) -0.05328(17) 0.0511(6) Uani 1 1 d . . .
H13A H 0.8419 1.4010 -0.0514 0.061 Uiso 1 1 calc R . .
H13B H 0.6853 1.3999 0.0064 0.061 Uiso 1 1 calc R . .
C14 C 0.6387(4) 1.4592(2) -0.1082(2) 0.0624(7) Uani 1 1 d . . .
H14A H 0.5198 1.4435 -0.1088 0.075 Uiso 1 1 calc R . .
H14B H 0.6623 1.5393 -0.0826 0.075 Uiso 1 1 calc R . .
C15 C 0.7380(3) 1.2378(2) -0.18178(16) 0.0469(6) Uani 1 1 d . . .
H15A H 0.7062 1.1587 -0.2071 0.056 Uiso 1 1 calc R . .
H15B H 0.8577 1.2476 -0.1824 0.056 Uiso 1 1 calc R . .
C16 C 0.6606(4) 1.3170(2) -0.23614(18) 0.0572(7) Uani 1 1 d . . .
H16A H 0.7022 1.3021 -0.2950 0.069 Uiso 1 1 calc R . .
H16B H 0.5417 1.3008 -0.2407 0.069 Uiso 1 1 calc R . .
C17 C 0.6087(6) 1.5091(3) -0.2526(3) 0.1135(16) Uani 1 1 d . . .
H17A H 0.6434 1.4919 -0.3121 0.170 Uiso 1 1 calc R . .
H17B H 0.6343 1.5889 -0.2296 0.170 Uiso 1 1 calc R . .
H17C H 0.4914 1.4929 -0.2514 0.170 Uiso 1 1 calc R . .
C18 C 0.5577(3) 1.0657(3) 0.35435(17) 0.0559(7) Uani 1 1 d . . .
H18 H 0.5071 1.0459 0.2986 0.067 Uiso 1 1 calc R . .
C19 C 0.5257(4) 1.1688(3) 0.40299(19) 0.0668(8) Uani 1 1 d . . .
H19 H 0.4561 1.2182 0.3808 0.080 Uiso 1 1 calc R . .
C20 C 0.5989(4) 1.1983(3) 0.4861(2) 0.0681(8) Uani 1 1 d . . .
H20 H 0.5810 1.2690 0.5204 0.082 Uiso 1 1 calc R . .
C21 C 0.6974(3) 1.1231(2) 0.51744(17) 0.0549(6) Uani 1 1 d . . .
H21 H 0.7465 1.1413 0.5736 0.066 Uiso 1 1 calc R . .
C22 C 0.7238(3) 1.0182(2) 0.46405(14) 0.0412(5) Uani 1 1 d . . .
C23 C 0.8333(3) 0.8275(2) 0.47476(15) 0.0462(6) Uani 1 1 d . . .
C24 C 0.8954(4) 0.7685(3) 0.53823(18) 0.0670(8) Uani 1 1 d . . .
H24 H 0.9354 0.8080 0.5927 0.080 Uiso 1 1 calc R . .
C25 C 0.8964(6) 0.6510(3) 0.5190(2) 0.0949(13) Uani 1 1 d . . .
H25 H 0.9339 0.6096 0.5611 0.114 Uiso 1 1 calc R . .
C26 C 0.8412(6) 0.5943(3) 0.4365(2) 0.1025(15) Uani 1 1 d . . .
H26 H 0.8380 0.5145 0.4227 0.123 Uiso 1 1 calc R . .
C27 C 0.7917(5) 0.6588(3) 0.3762(2) 0.0746(9) Uani 1 1 d . . .
H27 H 0.7586 0.6209 0.3202 0.090 Uiso 1 1 calc R . .
O4 O 0.9743(3) 0.4475(2) 0.1684(2) 0.0855(7) Uani 1 1 d D . .
H4A H 0.908(5) 0.491(3) 0.155(3) 0.128 Uiso 1 1 d D . .
H4B H 1.051(4) 0.491(3) 0.192(3) 0.128 Uiso 1 1 d D . .
O5 O 0.8464(7) 0.3360(3) 0.2959(2) 0.1422(13) Uani 1 1 d D . .
H5A H 0.867(9) 0.373(5) 0.255(3) 0.213 Uiso 1 1 d D . .
H5B H 0.798(8) 0.272(3) 0.281(5) 0.213 Uiso 1 1 d D . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.9200(17) . ?
Cu1 O3 1.9548(15) . ?
Cu1 N2 2.015(2) . ?
Cu1 N1 2.0156(19) . ?
Cu1 Cl1 2.5608(7) . ?
F1 C8 1.357(2) . ?
N1 C22 1.334(3) . ?
N1 C18 1.356(3) . ?
N2 C23 1.339(3) . ?
N2 C27 1.355(3) . ?
N3 C23 1.367(3) . ?
N3 C22 1.377(3) . ?
N3 H3A 0.862(17) . ?
N4 C3 1.338(3) . ?
N4 C6 1.399(3) . ?
N4 C11 1.478(3) . ?
N5 C9 1.372(3) . ?
N5 C15 1.459(3) . ?
N5 C13 1.478(3) . ?
N6 C16 1.460(3) . ?
N6 C14 1.467(4) . ?
N6 C17 1.467(4) . ?
O1 C1 1.282(3) . ?
O2 C1 1.230(3) . ?
O3 C4 1.279(2) . ?
C1 C2 1.494(3) . ?
C2 C3 1.374(3) . ?
C2 C4 1.417(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.440(3) . ?
C5 C7 1.410(3) . ?
C5 C6 1.410(3) . ?
C6 C10 1.392(3) . ?
C7 C8 1.336(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.425(3) . ?
C9 C10 1.402(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.509(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.499(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.505(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.358(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.360(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.397(3) . ?
C21 H21 0.9300 . ?
C23 C24 1.391(3) . ?
C24 C25 1.370(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.385(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.362(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
O4 H4A 0.805(19) . ?
O4 H4B 0.818(19) . ?
O5 H5A 0.84(2) . ?
O5 H5B 0.83(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O3 90.15(7) . . ?
O1 Cu1 N2 88.90(8) . . ?
O3 Cu1 N2 170.08(8) . . ?
O1 Cu1 N1 166.03(8) . . ?
O3 Cu1 N1 89.67(7) . . ?
N2 Cu1 N1 88.88(8) . . ?
O1 Cu1 Cl1 101.85(6) . . ?
O3 Cu1 Cl1 94.60(5) . . ?
N2 Cu1 Cl1 95.26(7) . . ?
N1 Cu1 Cl1 92.09(6) . . ?
C22 N1 C18 116.8(2) . . ?
C22 N1 Cu1 121.87(15) . . ?
C18 N1 Cu1 119.77(16) . . ?
C23 N2 C27 117.0(2) . . ?
C23 N2 Cu1 122.16(17) . . ?
C27 N2 Cu1 120.27(18) . . ?
C23 N3 C22 130.3(2) . . ?
C23 N3 H3A 114.6(18) . . ?
C22 N3 H3A 113.4(18) . . ?
C3 N4 C6 120.17(18) . . ?
C3 N4 C11 118.19(17) . . ?
C6 N4 C11 121.51(17) . . ?
C9 N5 C15 118.07(17) . . ?
C9 N5 C13 120.6(2) . . ?
C15 N5 C13 110.34(19) . . ?
C16 N6 C14 109.0(2) . . ?
C16 N6 C17 108.9(2) . . ?
C14 N6 C17 110.4(3) . . ?
C1 O1 Cu1 130.90(15) . . ?
C4 O3 Cu1 122.93(14) . . ?
O2 C1 O1 123.0(2) . . ?
O2 C1 C2 119.0(2) . . ?
O1 C1 C2 118.0(2) . . ?
C3 C2 C4 119.0(2) . . ?
C3 C2 C1 117.2(2) . . ?
C4 C2 C1 123.7(2) . . ?
N4 C3 C2 124.6(2) . . ?
N4 C3 H3 117.7 . . ?
C2 C3 H3 117.7 . . ?
O3 C4 C2 124.9(2) . . ?
O3 C4 C5 118.76(19) . . ?
C2 C4 C5 116.38(19) . . ?
C7 C5 C6 116.9(2) . . ?
C7 C5 C4 120.86(19) . . ?
C6 C5 C4 122.21(19) . . ?
C10 C6 N4 121.45(18) . . ?
C10 C6 C5 120.98(19) . . ?
N4 C6 C5 117.56(19) . . ?
C8 C7 C5 121.3(2) . . ?
C8 C7 H7 119.4 . . ?
C5 C7 H7 119.4 . . ?
C7 C8 F1 117.8(2) . . ?
C7 C8 C9 123.7(2) . . ?
F1 C8 C9 118.4(2) . . ?
N5 C9 C10 123.00(19) . . ?
N5 C9 C8 121.80(19) . . ?
C10 C9 C8 115.1(2) . . ?
C6 C10 C9 121.93(19) . . ?
C6 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
N4 C11 C12 111.77(19) . . ?
N4 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N4 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N5 C13 C14 109.7(2) . . ?
N5 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
N5 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
N6 C14 C13 110.7(2) . . ?
N6 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
N6 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N5 C15 C16 110.7(2) . . ?
N5 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N6 C16 C15 112.3(2) . . ?
N6 C16 H16A 109.1 . . ?
C15 C16 H16A 109.1 . . ?
N6 C16 H16B 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
N6 C17 H17A 109.5 . . ?
N6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 C19 123.9(3) . . ?
N1 C18 H18 118.1 . . ?
C19 C18 H18 118.1 . . ?
C18 C19 C20 118.4(3) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C21 C20 C19 119.4(3) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C22 119.1(3) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
N1 C22 N3 120.6(2) . . ?
N1 C22 C21 122.3(2) . . ?
N3 C22 C21 117.1(2) . . ?
N2 C23 N3 120.8(2) . . ?
N2 C23 C24 122.5(2) . . ?
N3 C23 C24 116.8(2) . . ?
C25 C24 C23 118.7(3) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
C24 C25 C26 119.6(3) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C27 C26 C25 118.1(3) . . ?
C27 C26 H26 121.0 . . ?
C25 C26 H26 121.0 . . ?
N2 C27 C26 123.9(3) . . ?
N2 C27 H27 118.1 . . ?
C26 C27 H27 118.1 . . ?
H4A O4 H4B 103(4) . . ?
H5A O5 H5B 117(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Cu1 N1 C22 116.9(3) . . . . ?
O3 Cu1 N1 C22 -153.78(18) . . . . ?
N2 Cu1 N1 C22 36.03(19) . . . . ?
Cl1 Cu1 N1 C22 -59.19(18) . . . . ?
O1 Cu1 N1 C18 -77.6(4) . . . . ?
O3 Cu1 N1 C18 11.6(2) . . . . ?
N2 Cu1 N1 C18 -158.5(2) . . . . ?
Cl1 Cu1 N1 C18 106.22(19) . . . . ?
O1 Cu1 N2 C23 159.7(2) . . . . ?
N1 Cu1 N2 C23 -34.1(2) . . . . ?
Cl1 Cu1 N2 C23 57.9(2) . . . . ?
O1 Cu1 N2 C27 -11.2(2) . . . . ?
N1 Cu1 N2 C27 155.0(2) . . . . ?
Cl1 Cu1 N2 C27 -113.0(2) . . . . ?
O3 Cu1 O1 C1 22.6(2) . . . . ?
N2 Cu1 O1 C1 -167.3(2) . . . . ?
N1 Cu1 O1 C1 111.8(3) . . . . ?
Cl1 Cu1 O1 C1 -72.2(2) . . . . ?
O1 Cu1 O3 C4 -32.35(19) . . . . ?
N1 Cu1 O3 C4 161.63(18) . . . . ?
Cl1 Cu1 O3 C4 69.56(18) . . . . ?
Cu1 O1 C1 O2 175.65(17) . . . . ?
Cu1 O1 C1 C2 -3.9(3) . . . . ?
O2 C1 C2 C3 -13.0(3) . . . . ?
O1 C1 C2 C3 166.6(2) . . . . ?
O2 C1 C2 C4 164.9(2) . . . . ?
O1 C1 C2 C4 -15.5(3) . . . . ?
C6 N4 C3 C2 -2.9(3) . . . . ?
C11 N4 C3 C2 -178.8(2) . . . . ?
C4 C2 C3 N4 1.3(3) . . . . ?
C1 C2 C3 N4 179.3(2) . . . . ?
Cu1 O3 C4 C2 25.3(3) . . . . ?
Cu1 O3 C4 C5 -154.67(15) . . . . ?
C3 C2 C4 O3 -178.5(2) . . . . ?
C1 C2 C4 O3 3.7(3) . . . . ?
C3 C2 C4 C5 1.5(3) . . . . ?
C1 C2 C4 C5 -176.3(2) . . . . ?
O3 C4 C5 C7 -2.4(3) . . . . ?
C2 C4 C5 C7 177.64(19) . . . . ?
O3 C4 C5 C6 177.2(2) . . . . ?
C2 C4 C5 C6 -2.8(3) . . . . ?
C3 N4 C6 C10 179.9(2) . . . . ?
C11 N4 C6 C10 -4.3(3) . . . . ?
C3 N4 C6 C5 1.5(3) . . . . ?
C11 N4 C6 C5 177.25(19) . . . . ?
C7 C5 C6 C10 2.5(3) . . . . ?
C4 C5 C6 C10 -177.1(2) . . . . ?
C7 C5 C6 N4 -179.06(18) . . . . ?
C4 C5 C6 N4 1.4(3) . . . . ?
C6 C5 C7 C8 0.1(3) . . . . ?
C4 C5 C7 C8 179.7(2) . . . . ?
C5 C7 C8 F1 175.0(2) . . . . ?
C5 C7 C8 C9 -2.5(4) . . . . ?
C15 N5 C9 C10 3.2(3) . . . . ?
C13 N5 C9 C10 -137.4(2) . . . . ?
C15 N5 C9 C8 -172.3(2) . . . . ?
C13 N5 C9 C8 47.1(3) . . . . ?
C7 C8 C9 N5 178.1(2) . . . . ?
F1 C8 C9 N5 0.5(3) . . . . ?
C7 C8 C9 C10 2.2(3) . . . . ?
F1 C8 C9 C10 -175.30(19) . . . . ?
N4 C6 C10 C9 178.84(19) . . . . ?
C5 C6 C10 C9 -2.7(3) . . . . ?
N5 C9 C10 C6 -175.4(2) . . . . ?
C8 C9 C10 C6 0.4(3) . . . . ?
C3 N4 C11 C12 98.7(2) . . . . ?
C6 N4 C11 C12 -77.2(3) . . . . ?
C9 N5 C13 C14 -158.6(2) . . . . ?
C15 N5 C13 C14 58.1(3) . . . . ?
C16 N6 C14 C13 58.7(3) . . . . ?
C17 N6 C14 C13 178.3(3) . . . . ?
N5 C13 C14 N6 -60.1(3) . . . . ?
C9 N5 C15 C16 160.1(2) . . . . ?
C13 N5 C15 C16 -55.6(3) . . . . ?
C14 N6 C16 C15 -56.5(3) . . . . ?
C17 N6 C16 C15 -177.0(3) . . . . ?
N5 C15 C16 N6 55.7(3) . . . . ?
C22 N1 C18 C19 3.2(4) . . . . ?
Cu1 N1 C18 C19 -162.9(2) . . . . ?
N1 C18 C19 C20 -0.7(5) . . . . ?
C18 C19 C20 C21 -1.3(5) . . . . ?
C19 C20 C21 C22 0.8(4) . . . . ?
C18 N1 C22 N3 176.2(2) . . . . ?
Cu1 N1 C22 N3 -18.0(3) . . . . ?
C18 N1 C22 C21 -3.7(3) . . . . ?
Cu1 N1 C22 C21 162.13(19) . . . . ?
C23 N3 C22 N1 -19.0(4) . . . . ?
C23 N3 C22 C21 160.8(2) . . . . ?
C20 C21 C22 N1 1.8(4) . . . . ?
C20 C21 C22 N3 -178.1(3) . . . . ?
C27 N2 C23 N3 -174.7(3) . . . . ?
Cu1 N2 C23 N3 14.1(3) . . . . ?
C27 N2 C23 C24 5.2(4) . . . . ?
Cu1 N2 C23 C24 -166.0(2) . . . . ?
C22 N3 C23 N2 21.2(4) . . . . ?
C22 N3 C23 C24 -158.7(3) . . . . ?
N2 C23 C24 C25 -5.9(5) . . . . ?
N3 C23 C24 C25 174.1(3) . . . . ?
C23 C24 C25 C26 2.1(6) . . . . ?
C24 C25 C26 C27 1.8(7) . . . . ?
C23 N2 C27 C26 -1.0(5) . . . . ?
Cu1 N2 C27 C26 170.4(3) . . . . ?
C25 C26 C27 N2 -2.4(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A Cl1 0.862(17) 2.321(17) 3.182(2) 177(2) 2_776
O4 H4A O2 0.805(19) 2.09(3) 2.834(3) 154(5) .
O4 H4B N6 0.818(19) 2.17(3) 2.923(3) 153(5) 2_775
O5 H5A O4 0.84(2) 1.93(3) 2.749(4) 164(7) .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.051
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1844911'
_audit_update_record             
;
2018-05-23 deposited with the CCDC.
2018-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
chlorido-(1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-quinoline-3-
carboxylato-O,O')-(1,10-phenanthroline-N,N')-copper(II)--methanol-water(1/1/2)
;
_chemical_name_common            
;
chlorido-(pefloxacinato-O,O')-(1,10-phenanthroline-N,N')-copper(II)--
methanol-water(1/1/2)
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H27 Cl Cu F N5 O3, C H4 O, 2(H2 O)'
_chemical_formula_sum            'C30 H35 Cl Cu F N5 O6'
_chemical_formula_weight         679.62

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   10.8217(2)
_cell_length_b                   24.4873(7)
_cell_length_c                   11.4809(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.870(2)
_cell_angle_gamma                90.00
_cell_volume                     3005.99(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7672
_cell_measurement_theta_min      2.9210
_cell_measurement_theta_max      30.0400

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1412
_exptl_absorpt_coefficient_mu    0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6944
_exptl_absorpt_correction_T_max  0.7794
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'

_exptl_special_details           
;
230 frames in 3 runs of ω scans. Crystal-detector distance = 55.0 mm. 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16879
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6872
_reflns_number_gt                5514
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0550P)²+3.9438P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6872
_refine_ls_number_parameters     407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.34147(3) 0.072498(15) 0.40529(3) 0.03103(11) Uani 1 1 d . . .
Cl1 Cl 0.18221(6) 0.06304(3) 0.22251(5) 0.03267(16) Uani 1 1 d . . .
F1 F 0.55419(16) -0.17407(7) 0.26325(15) 0.0421(4) Uani 1 1 d . . .
N1 N 0.25162(19) 0.02159(10) 0.50290(18) 0.0288(5) Uani 1 1 d . . .
N2 N 0.2587(2) 0.12931(10) 0.49519(19) 0.0320(5) Uani 1 1 d . . .
N3 N 0.64490(19) 0.02678(10) 0.08118(17) 0.0288(5) Uani 1 1 d . . .
N4 N 0.6891(2) -0.17144(10) 0.07832(19) 0.0334(5) Uani 1 1 d . . .
N5 N 0.7583(2) -0.26281(10) -0.0535(2) 0.0358(5) Uani 1 1 d . . .
O1 O 0.44647(19) 0.12826(9) 0.35699(18) 0.0413(5) Uani 1 1 d . . .
O2 O 0.5560(2) 0.16761(9) 0.23381(18) 0.0425(5) Uani 1 1 d . . .
O3 O 0.44581(17) 0.01445(9) 0.35745(16) 0.0344(4) Uani 1 1 d . . .
C1 C 0.5127(2) 0.12615(13) 0.2734(2) 0.0329(6) Uani 1 1 d . . .
C2 C 0.5409(2) 0.07140(12) 0.2259(2) 0.0299(6) Uani 1 1 d . . .
C3 C 0.6067(2) 0.07151(12) 0.1320(2) 0.0289(6) Uani 1 1 d . . .
H3 H 0.6264 0.1059 0.1012 0.035 Uiso 1 1 calc R . .
C4 C 0.5094(2) 0.02070(12) 0.2724(2) 0.0295(6) Uani 1 1 d . . .
C5 C 0.5538(2) -0.02759(12) 0.2203(2) 0.0274(5) Uani 1 1 d . . .
C6 C 0.6223(2) -0.02477(12) 0.1250(2) 0.0280(5) Uani 1 1 d . . .
C7 C 0.5298(2) -0.07985(12) 0.2628(2) 0.0323(6) Uani 1 1 d . . .
H7 H 0.4835 -0.0834 0.3263 0.039 Uiso 1 1 calc R . .
C8 C 0.5721(2) -0.12497(12) 0.2143(2) 0.0325(6) Uani 1 1 d . . .
C9 C 0.6414(2) -0.12349(12) 0.1184(2) 0.0308(6) Uani 1 1 d . . .
C10 C 0.6641(2) -0.07209(12) 0.0753(2) 0.0295(6) Uani 1 1 d . . .
H10 H 0.7090 -0.0690 0.0107 0.035 Uiso 1 1 calc R . .
C11 C 0.7172(2) 0.03376(12) -0.0181(2) 0.0289(6) Uani 1 1 d . . .
H11A H 0.6981 0.0700 -0.0550 0.035 Uiso 1 1 calc R . .
H11B H 0.6912 0.0055 -0.0786 0.035 Uiso 1 1 calc R . .
C12 C 0.8564(2) 0.02929(12) 0.0230(2) 0.0322(6) Uani 1 1 d . . .
H12A H 0.8818 0.0561 0.0854 0.048 Uiso 1 1 calc R . .
H12B H 0.9012 0.0364 -0.0434 0.048 Uiso 1 1 calc R . .
H12C H 0.8764 -0.0075 0.0536 0.048 Uiso 1 1 calc R . .
C13 C 0.6005(3) -0.21572(12) 0.0398(2) 0.0349(6) Uani 1 1 d . . .
H13A H 0.5515 -0.2065 -0.0377 0.042 Uiso 1 1 calc R . .
H13B H 0.5416 -0.2200 0.0971 0.042 Uiso 1 1 calc R . .
C14 C 0.6702(3) -0.26867(13) 0.0303(3) 0.0371(6) Uani 1 1 d . . .
H14A H 0.7161 -0.2788 0.1087 0.045 Uiso 1 1 calc R . .
H14B H 0.6099 -0.2982 0.0039 0.045 Uiso 1 1 calc R . .
C15 C 0.7823(3) -0.16590(13) -0.0015(3) 0.0366(6) Uani 1 1 d . . .
H15A H 0.8440 -0.1374 0.0285 0.044 Uiso 1 1 calc R . .
H15B H 0.7406 -0.1548 -0.0808 0.044 Uiso 1 1 calc R . .
C16 C 0.8482(3) -0.22007(13) -0.0092(3) 0.0409(7) Uani 1 1 d . . .
H16A H 0.9114 -0.2164 -0.0626 0.049 Uiso 1 1 calc R . .
H16B H 0.8920 -0.2304 0.0698 0.049 Uiso 1 1 calc R . .
C17 C 0.8217(3) -0.31422(14) -0.0691(3) 0.0465(8) Uani 1 1 d . . .
H17A H 0.8656 -0.3268 0.0073 0.070 Uiso 1 1 calc R . .
H17B H 0.8822 -0.3088 -0.1234 0.070 Uiso 1 1 calc R . .
H17C H 0.7600 -0.3417 -0.1015 0.070 Uiso 1 1 calc R . .
C18 C 0.2518(2) -0.03239(13) 0.5055(2) 0.0339(6) Uani 1 1 d . . .
H18 H 0.3038 -0.0517 0.4601 0.041 Uiso 1 1 calc R . .
C19 C 0.1780(3) -0.06205(13) 0.5730(2) 0.0364(6) Uani 1 1 d . . .
H19 H 0.1808 -0.1008 0.5734 0.044 Uiso 1 1 calc R . .
C20 C 0.1013(3) -0.03500(14) 0.6388(2) 0.0363(7) Uani 1 1 d . . .
H20 H 0.0499 -0.0549 0.6838 0.044 Uiso 1 1 calc R . .
C21 C 0.0997(2) 0.02240(13) 0.6388(2) 0.0319(6) Uani 1 1 d . . .
C22 C 0.1773(2) 0.04894(12) 0.5690(2) 0.0285(6) Uani 1 1 d . . .
C23 C 0.0256(3) 0.05523(14) 0.7055(2) 0.0369(7) Uani 1 1 d . . .
H23 H -0.0295 0.0379 0.7507 0.044 Uiso 1 1 calc R . .
C24 C 0.0327(3) 0.11006(14) 0.7050(2) 0.0375(7) Uani 1 1 d . . .
H24 H -0.0162 0.1307 0.7512 0.045 Uiso 1 1 calc R . .
C25 C 0.1133(2) 0.13816(13) 0.6356(2) 0.0343(6) Uani 1 1 d . . .
C26 C 0.1825(2) 0.10682(12) 0.5662(2) 0.0295(6) Uani 1 1 d . . .
C27 C 0.1274(3) 0.19520(14) 0.6317(2) 0.0393(7) Uani 1 1 d . . .
H27 H 0.0847 0.2181 0.6791 0.047 Uiso 1 1 calc R . .
C28 C 0.2034(3) 0.21756(14) 0.5588(3) 0.0408(7) Uani 1 1 d . . .
H28 H 0.2122 0.2561 0.5540 0.049 Uiso 1 1 calc R . .
C29 C 0.2678(3) 0.18308(13) 0.4917(2) 0.0373(6) Uani 1 1 d . . .
H29 H 0.3201 0.1989 0.4416 0.045 Uiso 1 1 calc R . .
O4 O 0.6078(3) -0.25562(11) -0.2771(2) 0.0490(6) Uani 1 1 d . . .
H4A H 0.658(4) -0.2509(18) -0.213(4) 0.073 Uiso 1 1 d . . .
H4B H 0.562(4) -0.2269(19) -0.275(4) 0.073 Uiso 1 1 d . . .
O5 O 0.6887(3) -0.33607(13) -0.4313(3) 0.0915(11) Uani 1 1 d . . .
H5A H 0.6482 -0.3103 -0.3965 0.137 Uiso 1 1 d R . .
H5B H 0.6547 -0.3442 -0.5096 0.137 Uiso 1 1 d R . .
O6 O -0.0264(3) 0.14621(11) 0.1589(3) 0.0639(7) Uani 1 1 d . . .
H6 H 0.0286 0.1217 0.1683 0.096 Uiso 1 1 calc R . .
C30 C -0.0112(7) 0.1806(2) 0.2575(5) 0.117(2) Uani 1 1 d . . .
H30A H 0.0617 0.2042 0.2559 0.176 Uiso 1 1 calc R . .
H30B H 0.0014 0.1585 0.3295 0.176 Uiso 1 1 calc R . .
H30C H -0.0862 0.2033 0.2561 0.176 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.912(2) . ?
Cu1 O3 1.946(2) . ?
Cu1 N2 2.022(2) . ?
Cu1 N1 2.023(2) . ?
Cu1 Cl1 2.5124(7) . ?
F1 C8 1.354(3) . ?
N1 C18 1.322(4) . ?
N1 C22 1.364(3) . ?
N2 C29 1.321(4) . ?
N2 C26 1.363(3) . ?
N3 C3 1.336(4) . ?
N3 C6 1.394(4) . ?
N3 C11 1.489(3) . ?
N4 C9 1.389(4) . ?
N4 C13 1.469(4) . ?
N4 C15 1.470(3) . ?
N5 C17 1.458(4) . ?
N5 C14 1.463(3) . ?
N5 C16 1.465(4) . ?
O1 C1 1.285(3) . ?
O2 C1 1.234(4) . ?
O3 C4 1.287(3) . ?
C1 C2 1.496(4) . ?
C2 C3 1.381(4) . ?
C2 C4 1.414(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.441(4) . ?
C5 C7 1.408(4) . ?
C5 C6 1.416(3) . ?
C6 C10 1.397(4) . ?
C7 C8 1.349(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.424(3) . ?
C9 C10 1.389(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.511(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.512(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.515(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.399(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.375(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.406(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.405(4) . ?
C21 C23 1.437(4) . ?
C22 C26 1.419(4) . ?
C23 C24 1.345(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.444(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.402(4) . ?
C25 C27 1.407(5) . ?
C27 C28 1.375(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.399(4) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
O4 H4A 0.85(5) . ?
O4 H4B 0.86(5) . ?
O5 H5A 0.8975 . ?
O5 H5B 0.9381 . ?
O6 C30 1.401(5) . ?
O6 H6 0.8400 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O3 92.47(9) . . ?
O1 Cu1 N2 89.22(9) . . ?
O3 Cu1 N2 165.57(9) . . ?
O1 Cu1 N1 163.44(9) . . ?
O3 Cu1 N1 93.18(9) . . ?
N2 Cu1 N1 81.53(9) . . ?
O1 Cu1 Cl1 100.68(7) . . ?
O3 Cu1 Cl1 92.87(6) . . ?
N2 Cu1 Cl1 100.90(7) . . ?
N1 Cu1 Cl1 94.56(6) . . ?
C18 N1 C22 118.5(2) . . ?
C18 N1 Cu1 129.02(18) . . ?
C22 N1 Cu1 112.39(19) . . ?
C29 N2 C26 118.4(2) . . ?
C29 N2 Cu1 129.00(19) . . ?
C26 N2 Cu1 112.59(19) . . ?
C3 N3 C6 120.1(2) . . ?
C3 N3 C11 118.3(2) . . ?
C6 N3 C11 121.5(2) . . ?
C9 N4 C13 117.7(2) . . ?
C9 N4 C15 117.0(2) . . ?
C13 N4 C15 111.0(2) . . ?
C17 N5 C14 111.3(2) . . ?
C17 N5 C16 111.1(2) . . ?
C14 N5 C16 107.9(2) . . ?
C1 O1 Cu1 127.81(19) . . ?
C4 O3 Cu1 121.88(19) . . ?
O2 C1 O1 122.0(3) . . ?
O2 C1 C2 119.5(2) . . ?
O1 C1 C2 118.5(3) . . ?
C3 C2 C4 118.7(3) . . ?
C3 C2 C1 116.2(3) . . ?
C4 C2 C1 125.1(2) . . ?
N3 C3 C2 124.8(3) . . ?
N3 C3 H3 117.6 . . ?
C2 C3 H3 117.6 . . ?
O3 C4 C2 125.4(3) . . ?
O3 C4 C5 118.0(3) . . ?
C2 C4 C5 116.6(2) . . ?
C7 C5 C6 117.3(2) . . ?
C7 C5 C4 120.7(2) . . ?
C6 C5 C4 122.0(3) . . ?
N3 C6 C10 121.2(2) . . ?
N3 C6 C5 117.7(2) . . ?
C10 C6 C5 121.1(3) . . ?
C8 C7 C5 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C5 C7 H7 119.7 . . ?
C7 C8 F1 118.5(2) . . ?
C7 C8 C9 123.4(3) . . ?
F1 C8 C9 118.0(3) . . ?
C10 C9 N4 123.5(2) . . ?
C10 C9 C8 116.2(3) . . ?
N4 C9 C8 120.1(3) . . ?
C9 C10 C6 121.3(2) . . ?
C9 C10 H10 119.3 . . ?
C6 C10 H10 119.3 . . ?
N3 C11 C12 111.6(2) . . ?
N3 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N3 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 C14 110.2(2) . . ?
N4 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
N4 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
N5 C14 C13 110.3(2) . . ?
N5 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
N5 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
N4 C15 C16 109.3(2) . . ?
N4 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
N4 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
N5 C16 C15 110.7(2) . . ?
N5 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
N5 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
N5 C17 H17A 109.5 . . ?
N5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 C19 122.2(3) . . ?
N1 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C20 C19 C18 119.9(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 119.3(3) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C22 C21 C20 117.0(2) . . ?
C22 C21 C23 118.5(3) . . ?
C20 C21 C23 124.5(3) . . ?
N1 C22 C21 123.1(3) . . ?
N1 C22 C26 116.7(2) . . ?
C21 C22 C26 120.3(2) . . ?
C24 C23 C21 121.3(3) . . ?
C24 C23 H23 119.4 . . ?
C21 C23 H23 119.4 . . ?
C23 C24 C25 121.2(3) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C26 C25 C27 117.1(3) . . ?
C26 C25 C24 118.3(3) . . ?
C27 C25 C24 124.6(3) . . ?
N2 C26 C25 123.0(3) . . ?
N2 C26 C22 116.6(2) . . ?
C25 C26 C22 120.5(2) . . ?
C28 C27 C25 119.5(3) . . ?
C28 C27 H27 120.2 . . ?
C25 C27 H27 120.2 . . ?
C27 C28 C29 119.4(3) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
N2 C29 C28 122.6(3) . . ?
N2 C29 H29 118.7 . . ?
C28 C29 H29 118.7 . . ?
H4A O4 H4B 99(4) . . ?
H5A O5 H5B 115.4 . . ?
C30 O6 H6 109.5 . . ?
O6 C30 H30A 109.5 . . ?
O6 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O6 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

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
O1 Cu1 N1 C18 -122.2(3) . . . . ?
O3 Cu1 N1 C18 -12.4(2) . . . . ?
N2 Cu1 N1 C18 -178.9(2) . . . . ?
Cl1 Cu1 N1 C18 80.7(2) . . . . ?
O1 Cu1 N1 C22 61.3(4) . . . . ?
O3 Cu1 N1 C22 171.13(17) . . . . ?
N2 Cu1 N1 C22 4.63(16) . . . . ?
Cl1 Cu1 N1 C22 -95.74(16) . . . . ?
O1 Cu1 N2 C29 11.3(2) . . . . ?
O3 Cu1 N2 C29 108.3(4) . . . . ?
N1 Cu1 N2 C29 177.6(3) . . . . ?
Cl1 Cu1 N2 C29 -89.4(2) . . . . ?
O1 Cu1 N2 C26 -169.97(18) . . . . ?
O3 Cu1 N2 C26 -73.0(4) . . . . ?
N1 Cu1 N2 C26 -3.75(17) . . . . ?
Cl1 Cu1 N2 C26 89.30(17) . . . . ?
O3 Cu1 O1 C1 30.3(3) . . . . ?
N2 Cu1 O1 C1 -164.0(3) . . . . ?
N1 Cu1 O1 C1 140.2(3) . . . . ?
Cl1 Cu1 O1 C1 -63.1(2) . . . . ?
O1 Cu1 O3 C4 -29.5(2) . . . . ?
N2 Cu1 O3 C4 -126.0(3) . . . . ?
N1 Cu1 O3 C4 166.1(2) . . . . ?
Cl1 Cu1 O3 C4 71.37(19) . . . . ?
Cu1 O1 C1 O2 164.6(2) . . . . ?
Cu1 O1 C1 C2 -17.4(4) . . . . ?
O2 C1 C2 C3 -5.2(4) . . . . ?
O1 C1 C2 C3 176.7(2) . . . . ?
O2 C1 C2 C4 172.4(3) . . . . ?
O1 C1 C2 C4 -5.8(4) . . . . ?
C6 N3 C3 C2 -2.1(4) . . . . ?
C11 N3 C3 C2 -178.9(2) . . . . ?
C4 C2 C3 N3 -0.7(4) . . . . ?
C1 C2 C3 N3 177.0(2) . . . . ?
Cu1 O3 C4 C2 18.5(3) . . . . ?
Cu1 O3 C4 C5 -162.19(17) . . . . ?
C3 C2 C4 O3 -178.2(2) . . . . ?
C1 C2 C4 O3 4.4(4) . . . . ?
C3 C2 C4 C5 2.5(3) . . . . ?
C1 C2 C4 C5 -175.0(2) . . . . ?
O3 C4 C5 C7 -1.0(3) . . . . ?
C2 C4 C5 C7 178.3(2) . . . . ?
O3 C4 C5 C6 178.8(2) . . . . ?
C2 C4 C5 C6 -1.8(3) . . . . ?
C3 N3 C6 C10 -178.4(2) . . . . ?
C11 N3 C6 C10 -1.6(3) . . . . ?
C3 N3 C6 C5 2.7(3) . . . . ?
C11 N3 C6 C5 179.4(2) . . . . ?
C7 C5 C6 N3 179.1(2) . . . . ?
C4 C5 C6 N3 -0.8(3) . . . . ?
C7 C5 C6 C10 0.1(3) . . . . ?
C4 C5 C6 C10 -179.7(2) . . . . ?
C6 C5 C7 C8 0.5(4) . . . . ?
C4 C5 C7 C8 -179.6(2) . . . . ?
C5 C7 C8 F1 175.5(2) . . . . ?
C5 C7 C8 C9 -0.5(4) . . . . ?
C13 N4 C9 C10 -127.4(3) . . . . ?
C15 N4 C9 C10 8.9(4) . . . . ?
C13 N4 C9 C8 57.1(3) . . . . ?
C15 N4 C9 C8 -166.6(2) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
F1 C8 C9 C10 -176.3(2) . . . . ?
C7 C8 C9 N4 175.6(3) . . . . ?
F1 C8 C9 N4 -0.4(4) . . . . ?
N4 C9 C10 C6 -174.8(2) . . . . ?
C8 C9 C10 C6 0.9(4) . . . . ?
N3 C6 C10 C9 -179.8(2) . . . . ?
C5 C6 C10 C9 -0.8(4) . . . . ?
C3 N3 C11 C12 97.6(3) . . . . ?
C6 N3 C11 C12 -79.2(3) . . . . ?
C9 N4 C13 C14 -165.0(2) . . . . ?
C15 N4 C13 C14 56.2(3) . . . . ?
C17 N5 C14 C13 -176.9(2) . . . . ?
C16 N5 C14 C13 61.1(3) . . . . ?
N4 C13 C14 N5 -58.9(3) . . . . ?
C9 N4 C15 C16 164.8(2) . . . . ?
C13 N4 C15 C16 -56.1(3) . . . . ?
C17 N5 C16 C15 176.0(2) . . . . ?
C14 N5 C16 C15 -61.8(3) . . . . ?
N4 C15 C16 N5 59.5(3) . . . . ?
C22 N1 C18 C19 0.4(4) . . . . ?
Cu1 N1 C18 C19 -175.90(19) . . . . ?
N1 C18 C19 C20 0.5(4) . . . . ?
C18 C19 C20 C21 -1.0(4) . . . . ?
C19 C20 C21 C22 0.7(4) . . . . ?
C19 C20 C21 C23 -178.8(3) . . . . ?
C18 N1 C22 C21 -0.7(4) . . . . ?
Cu1 N1 C22 C21 176.15(19) . . . . ?
C18 N1 C22 C26 178.3(2) . . . . ?
Cu1 N1 C22 C26 -4.8(3) . . . . ?
C20 C21 C22 N1 0.2(4) . . . . ?
C23 C21 C22 N1 179.7(2) . . . . ?
C20 C21 C22 C26 -178.8(2) . . . . ?
C23 C21 C22 C26 0.7(4) . . . . ?
C22 C21 C23 C24 -2.3(4) . . . . ?
C20 C21 C23 C24 177.2(3) . . . . ?
C21 C23 C24 C25 1.3(4) . . . . ?
C23 C24 C25 C26 1.4(4) . . . . ?
C23 C24 C25 C27 -179.0(3) . . . . ?
C29 N2 C26 C25 0.0(4) . . . . ?
Cu1 N2 C26 C25 -178.9(2) . . . . ?
C29 N2 C26 C22 -178.9(2) . . . . ?
Cu1 N2 C26 C22 2.3(3) . . . . ?
C27 C25 C26 N2 -1.4(4) . . . . ?
C24 C25 C26 N2 178.3(2) . . . . ?
C27 C25 C26 C22 177.4(2) . . . . ?
C24 C25 C26 C22 -2.9(4) . . . . ?
N1 C22 C26 N2 1.7(3) . . . . ?
C21 C22 C26 N2 -179.2(2) . . . . ?
N1 C22 C26 C25 -177.2(2) . . . . ?
C21 C22 C26 C25 1.9(4) . . . . ?
C26 C25 C27 C28 2.1(4) . . . . ?
C24 C25 C27 C28 -177.5(3) . . . . ?
C25 C27 C28 C29 -1.5(4) . . . . ?
C26 N2 C29 C28 0.7(4) . . . . ?
Cu1 N2 C29 C28 179.4(2) . . . . ?
C27 C28 C29 N2 0.0(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4A N5 0.85(5) 2.00(5) 2.825(3) 162(4) .
O4 H4B O2 0.86(5) 2.04(5) 2.882(3) 166(4) 3_655
O4 H4B O1 0.86(5) 2.59(5) 3.278(4) 138(4) 3_655
O5 H5A O4 0.90 2.01 2.874(4) 160.8 .
O5 H5B O6 0.94 2.05 2.947(4) 160.3 2_544
O6 H6 Cl1 0.84 2.21 3.044(3) 170.6 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.061
_refine_diff_density_min         -0.821
_refine_diff_density_rms         0.071
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1844912'
_audit_update_record             
;
2018-05-23 deposited with the CCDC.
2018-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
chlorido-(1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-quinoline-
3-carboxylato-O,O')-(2,2'-bipyridine-N,N')-copper(II)--methanol-water(2/1/8)
;
_chemical_name_common            
;
chlorido-(pefloxacinato-O,O')-(2,2'-bipyridine-N,N')-copper(II)
--methanol-water(2/1/8)
;
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C27 H27 Cl Cu F N5 O3), C H4 O, 8(H2 O)'
_chemical_formula_sum            'C55 H74 Cl2 Cu2 F2 N10 O15'
_chemical_formula_weight         1351.22

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   17.0082(2)
_cell_length_b                   24.7830(5)
_cell_length_c                   14.5284(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.631(2)
_cell_angle_gamma                90.00
_cell_volume                     6069.69(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12803
_cell_measurement_theta_min      3.2670
_cell_measurement_theta_max      29.8530

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2816
_exptl_absorpt_coefficient_mu    0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6238
_exptl_absorpt_correction_T_max  0.8121
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'

_exptl_special_details           
;
221 frames in 3 runs of ω scans. Crystal-detector distance = 55.0 mm. 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33231
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         27.48
_reflns_number_total             13894
_reflns_number_gt                10660
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0610P)²+5.1477P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         13894
_refine_ls_number_parameters     823
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1386
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.032
_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 0.034451(18) 0.419805(15) 0.63223(2) 0.03663(10) Uani 1 1 d . . .
Cl1 Cl 0.02142(4) 0.43067(3) 0.80350(5) 0.04534(18) Uani 1 1 d . . .
F1 F -0.14892(10) 0.66330(7) 0.59147(14) 0.0524(5) Uani 1 1 d . . .
N1 N 0.12673(12) 0.46955(10) 0.62693(15) 0.0366(5) Uani 1 1 d . . .
N2 N 0.12164(13) 0.36462(11) 0.63208(17) 0.0420(6) Uani 1 1 d . . .
N3 N -0.27989(12) 0.46331(9) 0.63014(14) 0.0304(5) Uani 1 1 d . . .
N4 N -0.30947(13) 0.65805(10) 0.60326(17) 0.0375(5) Uani 1 1 d . . .
N5 N -0.41438(14) 0.74601(10) 0.62296(18) 0.0445(6) Uani 1 1 d . . .
O1 O -0.04304(11) 0.36391(9) 0.60393(16) 0.0468(5) Uani 1 1 d . . .
O2 O -0.16050(12) 0.32557(9) 0.59365(16) 0.0473(5) Uani 1 1 d . . .
O3 O -0.04376(10) 0.47668(8) 0.59974(14) 0.0399(4) Uani 1 1 d . . .
C1 C -0.11808(16) 0.36605(12) 0.60416(18) 0.0351(6) Uani 1 1 d . . .
C2 C -0.15555(15) 0.41980(11) 0.61502(17) 0.0313(5) Uani 1 1 d . . .
C3 C -0.23478(15) 0.41948(11) 0.62649(17) 0.0312(5) Uani 1 1 d . . .
H3 H -0.2586 0.3861 0.6321 0.037 Uiso 1 1 calc R . .
C4 C -0.11713(14) 0.47059(11) 0.60884(16) 0.0307(5) Uani 1 1 d . . .
C5 C -0.16613(14) 0.51787(11) 0.61132(16) 0.0295(5) Uani 1 1 d . . .
C6 C -0.24758(14) 0.51398(11) 0.62009(16) 0.0292(5) Uani 1 1 d . . .
C7 C -0.13393(15) 0.57012(12) 0.60460(19) 0.0361(6) Uani 1 1 d . . .
H7 H -0.0802 0.5742 0.6004 0.043 Uiso 1 1 calc R . .
C8 C -0.18094(15) 0.61440(11) 0.60424(19) 0.0356(6) Uani 1 1 d . . .
C9 C -0.26339(15) 0.61152(11) 0.61122(18) 0.0331(6) Uani 1 1 d . . .
C10 C -0.29438(15) 0.56049(11) 0.62050(18) 0.0332(6) Uani 1 1 d . . .
H10 H -0.3478 0.5570 0.6272 0.040 Uiso 1 1 calc R . .
C11 C -0.36554(14) 0.45558(11) 0.63704(19) 0.0345(6) Uani 1 1 d . . .
H11A H -0.3839 0.4844 0.6740 0.041 Uiso 1 1 calc R . .
H11B H -0.3730 0.4217 0.6681 0.041 Uiso 1 1 calc R . .
C12 C -0.41396(16) 0.45529(14) 0.5420(2) 0.0469(7) Uani 1 1 d . . .
H12A H -0.4054 0.4884 0.5105 0.070 Uiso 1 1 calc R . .
H12B H -0.4692 0.4519 0.5485 0.070 Uiso 1 1 calc R . .
H12C H -0.3981 0.4254 0.5068 0.070 Uiso 1 1 calc R . .
C13 C -0.28690(17) 0.70173(12) 0.6701(2) 0.0425(7) Uani 1 1 d . . .
H13A H -0.2299 0.7070 0.6769 0.051 Uiso 1 1 calc R . .
H13B H -0.3015 0.6921 0.7302 0.051 Uiso 1 1 calc R . .
C14 C -0.32850(17) 0.75325(12) 0.6362(2) 0.0446(7) Uani 1 1 d . . .
H14A H -0.3143 0.7818 0.6811 0.054 Uiso 1 1 calc R . .
H14B H -0.3112 0.7640 0.5779 0.054 Uiso 1 1 calc R . .
C15 C -0.39603(16) 0.65063(12) 0.5876(2) 0.0433(7) Uani 1 1 d . . .
H15A H -0.4147 0.6390 0.6446 0.052 Uiso 1 1 calc R . .
H15B H -0.4097 0.6230 0.5409 0.052 Uiso 1 1 calc R . .
C16 C -0.43506(17) 0.70325(13) 0.5555(2) 0.0470(7) Uani 1 1 d . . .
H16A H -0.4185 0.7135 0.4966 0.056 Uiso 1 1 calc R . .
H16B H -0.4922 0.6985 0.5460 0.056 Uiso 1 1 calc R . .
C17 C -0.4549(2) 0.79681(15) 0.5926(3) 0.0650(10) Uani 1 1 d . . .
H17A H -0.4458 0.8230 0.6415 0.098 Uiso 1 1 calc R . .
H17B H -0.5108 0.7903 0.5781 0.098 Uiso 1 1 calc R . .
H17C H -0.4345 0.8101 0.5384 0.098 Uiso 1 1 calc R . .
C18 C 0.12317(17) 0.52317(14) 0.6255(2) 0.0447(7) Uani 1 1 d . . .
H18 H 0.0740 0.5399 0.6232 0.054 Uiso 1 1 calc R . .
C19 C 0.19039(19) 0.55478(14) 0.6272(2) 0.0500(8) Uani 1 1 d . . .
H19 H 0.1867 0.5922 0.6263 0.060 Uiso 1 1 calc R . .
C20 C 0.26322(18) 0.52957(16) 0.6305(2) 0.0527(8) Uani 1 1 d . . .
H20 H 0.3093 0.5500 0.6318 0.063 Uiso 1 1 calc R . .
C21 C 0.26710(17) 0.47465(15) 0.6317(2) 0.0466(7) Uani 1 1 d . . .
H21 H 0.3158 0.4573 0.6337 0.056 Uiso 1 1 calc R . .
C22 C 0.19807(16) 0.44491(13) 0.62973(18) 0.0394(7) Uani 1 1 d . . .
C23 C 0.19487(16) 0.38537(13) 0.63069(18) 0.0400(6) Uani 1 1 d . . .
C24 C 0.26050(19) 0.35190(16) 0.6298(2) 0.0530(8) Uani 1 1 d . . .
H24 H 0.3108 0.3666 0.6295 0.064 Uiso 1 1 calc R . .
C25 C 0.2501(2) 0.29679(16) 0.6292(2) 0.0583(9) Uani 1 1 d . . .
H25 H 0.2932 0.2739 0.6273 0.070 Uiso 1 1 calc R . .
C26 C 0.1756(2) 0.27587(15) 0.6315(3) 0.0594(9) Uani 1 1 d . . .
H26 H 0.1677 0.2388 0.6326 0.071 Uiso 1 1 calc R . .
Cu2 Cu 0.459490(17) 0.551747(14) 0.87991(2) 0.03271(9) Uani 1 1 d . . .
Cl2 Cl 0.47321(4) 0.54350(4) 0.70516(5) 0.04749(19) Uani 1 1 d . . .
F2 F 0.64250(10) 0.31098(7) 0.88665(13) 0.0491(4) Uani 1 1 d . . .
N6 N 0.37040(12) 0.60468(9) 0.88400(15) 0.0324(5) Uani 1 1 d . . .
N7 N 0.36950(12) 0.50001(9) 0.87933(14) 0.0305(5) Uani 1 1 d . . .
N8 N 0.77156(12) 0.51280(9) 0.86078(14) 0.0316(5) Uani 1 1 d . . .
N9 N 0.80132(13) 0.31680(10) 0.86849(17) 0.0398(5) Uani 1 1 d . . .
N10 N 0.90200(15) 0.22709(10) 0.84261(18) 0.0444(6) Uani 1 1 d . . .
O4 O 0.53528(11) 0.60861(8) 0.90606(15) 0.0436(5) Uani 1 1 d . . .
O5 O 0.64502(13) 0.64988(9) 0.88059(18) 0.0571(6) Uani 1 1 d . . .
O6 O 0.53971(10) 0.49570(8) 0.90597(13) 0.0350(4) Uani 1 1 d . . .
C27 C 0.11234(19) 0.31127(14) 0.6323(2) 0.0518(8) Uani 1 1 d . . .
H27 H 0.0617 0.2972 0.6331 0.062 Uiso 1 1 calc R . .
C28 C 0.60729(15) 0.60816(12) 0.88892(19) 0.0369(6) Uani 1 1 d . . .
C29 C 0.64726(14) 0.55435(11) 0.88083(17) 0.0318(5) Uani 1 1 d . . .
C30 C 0.72536(15) 0.55587(11) 0.86675(18) 0.0329(6) Uani 1 1 d . . .
H30 H 0.7480 0.5896 0.8609 0.039 Uiso 1 1 calc R . .
C31 C 0.61125(14) 0.50324(11) 0.89023(16) 0.0287(5) Uani 1 1 d . . .
C32 C 0.66013(14) 0.45638(11) 0.88127(16) 0.0290(5) Uani 1 1 d . . .
C33 C 0.74066(14) 0.46132(11) 0.86840(16) 0.0290(5) Uani 1 1 d . . .
C34 C 0.62838(14) 0.40420(11) 0.88518(18) 0.0327(6) Uani 1 1 d . . .
H34 H 0.5754 0.3998 0.8930 0.039 Uiso 1 1 calc R . .
C35 C 0.67440(15) 0.36033(11) 0.87768(19) 0.0352(6) Uani 1 1 d . . .
C36 C 0.75603(15) 0.36340(11) 0.86683(18) 0.0335(6) Uani 1 1 d . . .
C37 C 0.78738(15) 0.41472(11) 0.86185(18) 0.0332(6) Uani 1 1 d . . .
H37 H 0.8405 0.4186 0.8540 0.040 Uiso 1 1 calc R . .
C38 C 0.85696(14) 0.52168(12) 0.85464(19) 0.0358(6) Uani 1 1 d . . .
H38A H 0.8639 0.5566 0.8267 0.043 Uiso 1 1 calc R . .
H38B H 0.8756 0.4943 0.8151 0.043 Uiso 1 1 calc R . .
C39 C 0.90509(17) 0.51946(16) 0.9487(2) 0.0516(8) Uani 1 1 d . . .
H39A H 0.8868 0.5467 0.9878 0.077 Uiso 1 1 calc R . .
H39B H 0.9599 0.5257 0.9429 0.077 Uiso 1 1 calc R . .
H39C H 0.8994 0.4845 0.9757 0.077 Uiso 1 1 calc R . .
C40 C 0.77484(17) 0.27243(12) 0.8045(2) 0.0425(7) Uani 1 1 d . . .
H40A H 0.7865 0.2811 0.7426 0.051 Uiso 1 1 calc R . .
H40B H 0.7179 0.2678 0.8015 0.051 Uiso 1 1 calc R . .
C41 C 0.81654(17) 0.22055(13) 0.8374(2) 0.0446(7) Uani 1 1 d . . .
H41A H 0.8030 0.2110 0.8981 0.053 Uiso 1 1 calc R . .
H41B H 0.7990 0.1916 0.7947 0.053 Uiso 1 1 calc R . .
C42 C 0.88801(16) 0.32293(13) 0.8793(3) 0.0490(8) Uani 1 1 d . . .
H42A H 0.9044 0.3505 0.9252 0.059 Uiso 1 1 calc R . .
H42B H 0.9045 0.3340 0.8207 0.059 Uiso 1 1 calc R . .
C43 C 0.92636(18) 0.26984(14) 0.9096(3) 0.0543(8) Uani 1 1 d . . .
H43A H 0.9836 0.2738 0.9163 0.065 Uiso 1 1 calc R . .
H43B H 0.9117 0.2599 0.9696 0.065 Uiso 1 1 calc R . .
C44 C 0.9445(2) 0.17654(14) 0.8681(3) 0.0600(9) Uani 1 1 d . . .
H44A H 0.9305 0.1637 0.9261 0.090 Uiso 1 1 calc R . .
H44B H 1.0007 0.1829 0.8743 0.090 Uiso 1 1 calc R . .
H44C H 0.9302 0.1500 0.8207 0.090 Uiso 1 1 calc R . .
C45 C 0.37777(17) 0.65807(12) 0.8911(2) 0.0423(7) Uani 1 1 d . . .
H45 H 0.4278 0.6734 0.8925 0.051 Uiso 1 1 calc R . .
C46 C 0.31330(19) 0.69145(13) 0.8966(2) 0.0484(7) Uani 1 1 d . . .
H46 H 0.3201 0.7286 0.9022 0.058 Uiso 1 1 calc R . .
C47 C 0.23919(19) 0.66897(14) 0.8936(2) 0.0502(8) Uani 1 1 d . . .
H47 H 0.1952 0.6907 0.8975 0.060 Uiso 1 1 calc R . .
C48 C 0.23063(17) 0.61376(13) 0.8846(2) 0.0424(7) Uani 1 1 d . . .
H48 H 0.1808 0.5978 0.8814 0.051 Uiso 1 1 calc R . .
C49 C 0.29787(15) 0.58243(11) 0.88057(17) 0.0331(6) Uani 1 1 d . . .
C50 C 0.29701(14) 0.52293(11) 0.87602(16) 0.0300(5) Uani 1 1 d . . .
C51 C 0.22885(16) 0.49226(13) 0.8689(2) 0.0403(6) Uani 1 1 d . . .
H51 H 0.1794 0.5087 0.8647 0.048 Uiso 1 1 calc R . .
C52 C 0.23509(18) 0.43693(13) 0.8680(2) 0.0473(7) Uani 1 1 d . . .
H52 H 0.1898 0.4156 0.8637 0.057 Uiso 1 1 calc R . .
C53 C 0.30906(18) 0.41336(13) 0.8733(2) 0.0481(7) Uani 1 1 d . . .
H53 H 0.3144 0.3760 0.8736 0.058 Uiso 1 1 calc R . .
C54 C 0.37504(16) 0.44622(11) 0.8783(2) 0.0382(6) Uani 1 1 d . . .
H54 H 0.4249 0.4304 0.8811 0.046 Uiso 1 1 calc R . .
O7 O 0.94614(17) 0.23726(11) 0.66401(19) 0.0689(7) Uani 1 1 d D . .
H7A H 0.9407 0.2374 0.7195 0.103 Uiso 1 1 d RD . .
H7B H 0.926(3) 0.2644(12) 0.640(3) 0.103 Uiso 1 1 d D . .
O8 O 1.0429(3) 0.15010(15) 0.6326(3) 0.1201(15) Uani 1 1 d D . .
H8A H 1.0052 0.1701 0.6365 0.180 Uiso 1 1 d RD . .
H8B H 1.081(3) 0.152(3) 0.605(5) 0.180 Uiso 1 1 d D . .
O9 O 0.95036(19) 0.06465(14) 0.6964(3) 0.0857(9) Uani 1 1 d D . .
H9A H 0.983(3) 0.085(2) 0.676(4) 0.129 Uiso 1 1 d D . .
H9B H 0.971(3) 0.0348(11) 0.701(4) 0.129 Uiso 1 1 d D . .
O10 O 0.3956(2) 0.66127(15) 0.6653(2) 0.0824(8) Uani 1 1 d D . .
H10A H 0.418(3) 0.6320(12) 0.669(4) 0.124 Uiso 1 1 d D . .
H10B H 0.423(3) 0.679(2) 0.704(3) 0.124 Uiso 1 1 d D . .
O11 O -0.33324(16) 0.31842(12) 0.5198(2) 0.0639(7) Uani 1 1 d D . .
H11C H -0.2848(7) 0.316(2) 0.522(3) 0.096 Uiso 1 1 d D . .
H11D H -0.356(2) 0.321(2) 0.4667(14) 0.096 Uiso 1 1 d D . .
O12 O -0.47636(19) 0.72767(12) 0.7918(2) 0.0785(9) Uani 1 1 d D . .
H12D H -0.455(3) 0.730(2) 0.745(2) 0.118 Uiso 1 1 d D . .
H12E H -0.451(3) 0.7030(16) 0.820(3) 0.118 Uiso 1 1 d D . .
O13 O -0.4401(2) 0.32432(12) 0.6619(2) 0.0766(8) Uani 1 1 d D . .
H13C H -0.470(3) 0.2985(14) 0.666(4) 0.115 Uiso 1 1 d D . .
H13D H -0.412(3) 0.322(2) 0.620(3) 0.115 Uiso 1 1 d D . .
O14 O 0.44404(17) 0.40688(16) 0.6866(3) 0.0961(11) Uani 1 1 d D . .
H14C H 0.468(4) 0.4354(14) 0.694(5) 0.144 Uiso 1 1 d D . .
H14D H 0.478(3) 0.384(2) 0.678(5) 0.144 Uiso 1 1 d D . .
C55 C 0.1348(4) 0.3101(2) 0.8983(7) 0.213(5) Uani 1 1 d . . .
H55A H 0.1894 0.3078 0.9253 0.319 Uiso 1 1 calc R . .
H55B H 0.1319 0.3229 0.8356 0.319 Uiso 1 1 calc R . .
H55C H 0.1109 0.2750 0.8985 0.319 Uiso 1 1 calc R . .
O15 O 0.0943(2) 0.34605(16) 0.9505(3) 0.1058(11) Uani 1 1 d . . .
H15 H 0.0755 0.3707 0.9170 0.159 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.919(2) . ?
Cu1 O3 1.9525(19) . ?
Cu1 N1 2.005(2) . ?
Cu1 N2 2.017(2) . ?
Cu1 Cl1 2.5415(8) . ?
F1 C8 1.351(3) . ?
N1 C18 1.330(4) . ?
N1 C22 1.354(3) . ?
N2 C27 1.332(4) . ?
N2 C23 1.350(4) . ?
N3 C3 1.335(3) . ?
N3 C6 1.386(3) . ?
N3 C11 1.486(3) . ?
N4 C9 1.390(3) . ?
N4 C13 1.471(4) . ?
N4 C15 1.471(3) . ?
N5 C16 1.455(4) . ?
N5 C14 1.459(4) . ?
N5 C17 1.474(4) . ?
O1 C1 1.278(3) . ?
O2 C1 1.233(3) . ?
O3 C4 1.281(3) . ?
C1 C2 1.494(4) . ?
C2 C3 1.380(3) . ?
C2 C4 1.427(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.441(4) . ?
C5 C6 1.411(3) . ?
C5 C7 1.414(4) . ?
C6 C10 1.401(4) . ?
C7 C8 1.357(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.421(3) . ?
C9 C10 1.384(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.511(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.510(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.509(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.383(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.363(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.383(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.477(4) . ?
C23 C24 1.392(4) . ?
C24 C25 1.377(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.373(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.390(4) . ?
C26 H26 0.9300 . ?
Cu2 O4 1.914(2) . ?
Cu2 O6 1.9487(18) . ?
Cu2 N7 1.996(2) . ?
Cu2 N6 2.011(2) . ?
Cu2 Cl2 2.5883(8) . ?
F2 C35 1.351(3) . ?
N6 C45 1.332(4) . ?
N6 C49 1.346(3) . ?
N7 C54 1.337(3) . ?
N7 C50 1.353(3) . ?
N8 C30 1.335(3) . ?
N8 C33 1.390(3) . ?
N8 C38 1.483(3) . ?
N9 C36 1.387(3) . ?
N9 C42 1.470(3) . ?
N9 C40 1.472(4) . ?
N10 C41 1.454(4) . ?
N10 C43 1.461(4) . ?
N10 C44 1.469(4) . ?
O4 C28 1.282(3) . ?
O5 C28 1.231(3) . ?
O6 C31 1.281(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.508(4) . ?
C29 C30 1.371(3) . ?
C29 C31 1.421(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.444(3) . ?
C32 C34 1.405(4) . ?
C32 C33 1.412(3) . ?
C33 C37 1.412(4) . ?
C34 C35 1.353(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.420(3) . ?
C36 C37 1.385(4) . ?
C37 H37 0.9300 . ?
C38 C39 1.498(4) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 C41 1.515(4) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.508(4) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 C46 1.384(4) . ?
C45 H45 0.9300 . ?
C46 C47 1.373(5) . ?
C46 H46 0.9300 . ?
C47 C48 1.380(5) . ?
C47 H47 0.9300 . ?
C48 C49 1.390(4) . ?
C48 H48 0.9300 . ?
C49 C50 1.476(4) . ?
C50 C51 1.379(4) . ?
C51 C52 1.376(4) . ?
C51 H51 0.9300 . ?
C52 C53 1.380(4) . ?
C52 H52 0.9300 . ?
C53 C54 1.381(4) . ?
C53 H53 0.9300 . ?
C54 H54 0.9300 . ?
O7 H7A 0.8239 . ?
O7 H7B 0.817(10) . ?
O8 H8A 0.8191 . ?
O8 H8B 0.815(10) . ?
O9 H9A 0.823(10) . ?
O9 H9B 0.819(10) . ?
O10 H10A 0.821(10) . ?
O10 H10B 0.818(10) . ?
O11 H11C 0.821(10) . ?
O11 H11D 0.819(10) . ?
O12 H12D 0.818(10) . ?
O12 H12E 0.823(10) . ?
O13 H13C 0.818(10) . ?
O13 H13D 0.818(10) . ?
O14 H14C 0.815(10) . ?
O14 H14D 0.822(10) . ?
C55 O15 1.409(6) . ?
C55 H55A 0.9600 . ?
C55 H55B 0.9600 . ?
C55 H55C 0.9600 . ?
O15 H15 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O3 92.46(8) . . ?
O1 Cu1 N1 162.65(9) . . ?
O3 Cu1 N1 93.35(9) . . ?
O1 Cu1 N2 89.68(10) . . ?
O3 Cu1 N2 165.10(9) . . ?
N1 Cu1 N2 80.66(10) . . ?
O1 Cu1 Cl1 98.02(7) . . ?
O3 Cu1 Cl1 90.86(6) . . ?
N1 Cu1 Cl1 98.22(7) . . ?
N2 Cu1 Cl1 103.45(7) . . ?
C18 N1 C22 119.3(3) . . ?
C18 N1 Cu1 125.49(19) . . ?
C22 N1 Cu1 115.1(2) . . ?
C27 N2 C23 119.2(3) . . ?
C27 N2 Cu1 125.8(2) . . ?
C23 N2 Cu1 114.9(2) . . ?
C3 N3 C6 119.7(2) . . ?
C3 N3 C11 118.2(2) . . ?
C6 N3 C11 122.0(2) . . ?
C9 N4 C13 117.4(2) . . ?
C9 N4 C15 116.8(2) . . ?
C13 N4 C15 111.3(2) . . ?
C16 N5 C14 109.1(2) . . ?
C16 N5 C17 111.0(3) . . ?
C14 N5 C17 110.8(2) . . ?
C1 O1 Cu1 128.86(19) . . ?
C4 O3 Cu1 122.12(18) . . ?
O2 C1 O1 122.3(3) . . ?
O2 C1 C2 119.2(2) . . ?
O1 C1 C2 118.5(2) . . ?
C3 C2 C4 118.4(2) . . ?
C3 C2 C1 116.4(2) . . ?
C4 C2 C1 125.1(2) . . ?
N3 C3 C2 125.2(2) . . ?
N3 C3 H3 117.4 . . ?
C2 C3 H3 117.4 . . ?
O3 C4 C2 124.8(2) . . ?
O3 C4 C5 118.8(2) . . ?
C2 C4 C5 116.4(2) . . ?
C6 C5 C7 117.6(2) . . ?
C6 C5 C4 121.6(2) . . ?
C7 C5 C4 120.8(2) . . ?
N3 C6 C10 120.8(2) . . ?
N3 C6 C5 118.6(2) . . ?
C10 C6 C5 120.6(2) . . ?
C8 C7 C5 120.5(2) . . ?
C8 C7 H7 119.8 . . ?
C5 C7 H7 119.8 . . ?
F1 C8 C7 118.5(2) . . ?
F1 C8 C9 118.3(2) . . ?
C7 C8 C9 123.1(3) . . ?
C10 C9 N4 123.3(2) . . ?
C10 C9 C8 116.4(2) . . ?
N4 C9 C8 120.2(2) . . ?
C9 C10 C6 121.8(2) . . ?
C9 C10 H10 119.1 . . ?
C6 C10 H10 119.1 . . ?
N3 C11 C12 111.1(2) . . ?
N3 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N3 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 C14 109.7(2) . . ?
N4 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
N4 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
N5 C14 C13 110.9(2) . . ?
N5 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
N5 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N4 C15 C16 109.3(2) . . ?
N4 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
N4 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
N5 C16 C15 111.4(3) . . ?
N5 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
N5 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N5 C17 H17A 109.5 . . ?
N5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 C19 122.0(3) . . ?
N1 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C20 C19 C18 118.6(3) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C21 C20 C19 119.6(3) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 119.5(3) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
N1 C22 C21 121.0(3) . . ?
N1 C22 C23 114.6(2) . . ?
C21 C22 C23 124.4(3) . . ?
N2 C23 C24 121.0(3) . . ?
N2 C23 C22 114.6(2) . . ?
C24 C23 C22 124.4(3) . . ?
C25 C24 C23 119.2(3) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C26 C25 C24 119.5(3) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C27 118.7(4) . . ?
C25 C26 H26 120.7 . . ?
C27 C26 H26 120.7 . . ?
O4 Cu2 O6 92.90(8) . . ?
O4 Cu2 N7 165.92(8) . . ?
O6 Cu2 N7 93.42(8) . . ?
O4 Cu2 N6 90.23(8) . . ?
O6 Cu2 N6 165.96(8) . . ?
N7 Cu2 N6 80.73(9) . . ?
O4 Cu2 Cl2 96.13(7) . . ?
O6 Cu2 Cl2 88.99(6) . . ?
N7 Cu2 Cl2 96.55(6) . . ?
N6 Cu2 Cl2 104.29(6) . . ?
C45 N6 C49 119.1(2) . . ?
C45 N6 Cu2 125.94(19) . . ?
C49 N6 Cu2 114.95(18) . . ?
C54 N7 C50 118.9(2) . . ?
C54 N7 Cu2 125.85(18) . . ?
C50 N7 Cu2 115.17(18) . . ?
C30 N8 C33 119.8(2) . . ?
C30 N8 C38 118.3(2) . . ?
C33 N8 C38 121.6(2) . . ?
C36 N9 C42 117.6(2) . . ?
C36 N9 C40 119.2(2) . . ?
C42 N9 C40 111.3(2) . . ?
C41 N10 C43 108.0(2) . . ?
C41 N10 C44 111.9(3) . . ?
C43 N10 C44 111.3(3) . . ?
C28 O4 Cu2 126.22(18) . . ?
C31 O6 Cu2 121.22(17) . . ?
N2 C27 C26 122.3(3) . . ?
N2 C27 H27 118.9 . . ?
C26 C27 H27 118.9 . . ?
O5 C28 O4 122.4(3) . . ?
O5 C28 C29 119.2(2) . . ?
O4 C28 C29 118.4(2) . . ?
C30 C29 C31 118.5(2) . . ?
C30 C29 C28 116.3(2) . . ?
C31 C29 C28 125.2(2) . . ?
N8 C30 C29 125.3(3) . . ?
N8 C30 H30 117.3 . . ?
C29 C30 H30 117.3 . . ?
O6 C31 C29 125.4(2) . . ?
O6 C31 C32 118.1(2) . . ?
C29 C31 C32 116.6(2) . . ?
C34 C32 C33 118.0(2) . . ?
C34 C32 C31 120.5(2) . . ?
C33 C32 C31 121.5(2) . . ?
N8 C33 C37 121.6(2) . . ?
N8 C33 C32 118.3(2) . . ?
C37 C33 C32 120.1(2) . . ?
C35 C34 C32 120.4(2) . . ?
C35 C34 H34 119.8 . . ?
C32 C34 H34 119.8 . . ?
F2 C35 C34 118.4(2) . . ?
F2 C35 C36 118.1(2) . . ?
C34 C35 C36 123.4(3) . . ?
C37 C36 N9 123.3(2) . . ?
C37 C36 C35 116.4(2) . . ?
N9 C36 C35 120.2(3) . . ?
C36 C37 C33 121.6(2) . . ?
C36 C37 H37 119.2 . . ?
C33 C37 H37 119.2 . . ?
N8 C38 C39 111.1(2) . . ?
N8 C38 H38A 109.4 . . ?
C39 C38 H38A 109.4 . . ?
N8 C38 H38B 109.4 . . ?
C39 C38 H38B 109.4 . . ?
H38A C38 H38B 108.0 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
N9 C40 C41 110.1(2) . . ?
N9 C40 H40A 109.6 . . ?
C41 C40 H40A 109.6 . . ?
N9 C40 H40B 109.6 . . ?
C41 C40 H40B 109.6 . . ?
H40A C40 H40B 108.2 . . ?
N10 C41 C40 110.2(2) . . ?
N10 C41 H41A 109.6 . . ?
C40 C41 H41A 109.6 . . ?
N10 C41 H41B 109.6 . . ?
C40 C41 H41B 109.6 . . ?
H41A C41 H41B 108.1 . . ?
N9 C42 C43 109.3(3) . . ?
N9 C42 H42A 109.8 . . ?
C43 C42 H42A 109.8 . . ?
N9 C42 H42B 109.8 . . ?
C43 C42 H42B 109.8 . . ?
H42A C42 H42B 108.3 . . ?
N10 C43 C42 111.4(3) . . ?
N10 C43 H43A 109.3 . . ?
C42 C43 H43A 109.3 . . ?
N10 C43 H43B 109.3 . . ?
C42 C43 H43B 109.3 . . ?
H43A C43 H43B 108.0 . . ?
N10 C44 H44A 109.5 . . ?
N10 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
N10 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N6 C45 C46 122.1(3) . . ?
N6 C45 H45 119.0 . . ?
C46 C45 H45 119.0 . . ?
C47 C46 C45 119.1(3) . . ?
C47 C46 H46 120.4 . . ?
C45 C46 H46 120.4 . . ?
C46 C47 C48 119.3(3) . . ?
C46 C47 H47 120.3 . . ?
C48 C47 H47 120.3 . . ?
C47 C48 C49 118.7(3) . . ?
C47 C48 H48 120.6 . . ?
C49 C48 H48 120.6 . . ?
N6 C49 C48 121.6(3) . . ?
N6 C49 C50 114.5(2) . . ?
C48 C49 C50 123.8(2) . . ?
N7 C50 C51 121.7(3) . . ?
N7 C50 C49 114.5(2) . . ?
C51 C50 C49 123.9(2) . . ?
C52 C51 C50 119.0(3) . . ?
C52 C51 H51 120.5 . . ?
C50 C51 H51 120.5 . . ?
C51 C52 C53 119.5(3) . . ?
C51 C52 H52 120.3 . . ?
C53 C52 H52 120.3 . . ?
C52 C53 C54 118.8(3) . . ?
C52 C53 H53 120.6 . . ?
C54 C53 H53 120.6 . . ?
N7 C54 C53 122.1(3) . . ?
N7 C54 H54 119.0 . . ?
C53 C54 H54 119.0 . . ?
H7A O7 H7B 109.0 . . ?
H8A O8 H8B 132.9 . . ?
H9A O9 H9B 106(5) . . ?
H10A O10 H10B 102(6) . . ?
H11C O11 H11D 113(5) . . ?
H12D O12 H12E 101(5) . . ?
H13C O13 H13D 114(5) . . ?
H14C O14 H14D 105(6) . . ?
O15 C55 H55A 109.5 . . ?
O15 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
O15 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C55 O15 H15 109.5 . . ?

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
O1 Cu1 N1 C18 123.8(3) . . . . ?
O3 Cu1 N1 C18 14.5(2) . . . . ?
N2 Cu1 N1 C18 -179.2(2) . . . . ?
Cl1 Cu1 N1 C18 -76.9(2) . . . . ?
O1 Cu1 N1 C22 -59.5(4) . . . . ?
O3 Cu1 N1 C22 -168.88(19) . . . . ?
N2 Cu1 N1 C22 -2.62(18) . . . . ?
Cl1 Cu1 N1 C22 99.76(18) . . . . ?
O1 Cu1 N2 C27 -12.5(3) . . . . ?
O3 Cu1 N2 C27 -110.9(4) . . . . ?
N1 Cu1 N2 C27 -178.0(3) . . . . ?
Cl1 Cu1 N2 C27 85.7(3) . . . . ?
O1 Cu1 N2 C23 166.8(2) . . . . ?
O3 Cu1 N2 C23 68.5(4) . . . . ?
N1 Cu1 N2 C23 1.30(19) . . . . ?
Cl1 Cu1 N2 C23 -95.00(19) . . . . ?
O3 Cu1 O1 C1 -25.0(3) . . . . ?
N1 Cu1 O1 C1 -134.5(3) . . . . ?
N2 Cu1 O1 C1 169.7(3) . . . . ?
Cl1 Cu1 O1 C1 66.2(2) . . . . ?
O1 Cu1 O3 C4 29.5(2) . . . . ?
N1 Cu1 O3 C4 -166.9(2) . . . . ?
N2 Cu1 O3 C4 127.5(4) . . . . ?
Cl1 Cu1 O3 C4 -68.6(2) . . . . ?
Cu1 O1 C1 O2 -172.5(2) . . . . ?
Cu1 O1 C1 C2 9.2(4) . . . . ?
O2 C1 C2 C3 9.4(4) . . . . ?
O1 C1 C2 C3 -172.2(2) . . . . ?
O2 C1 C2 C4 -166.6(3) . . . . ?
O1 C1 C2 C4 11.8(4) . . . . ?
C6 N3 C3 C2 1.4(4) . . . . ?
C11 N3 C3 C2 176.3(2) . . . . ?
C4 C2 C3 N3 1.7(4) . . . . ?
C1 C2 C3 N3 -174.6(2) . . . . ?
Cu1 O3 C4 C2 -20.1(3) . . . . ?
Cu1 O3 C4 C5 161.18(17) . . . . ?
C3 C2 C4 O3 178.8(2) . . . . ?
C1 C2 C4 O3 -5.2(4) . . . . ?
C3 C2 C4 C5 -2.5(3) . . . . ?
C1 C2 C4 C5 173.5(2) . . . . ?
O3 C4 C5 C6 179.2(2) . . . . ?
C2 C4 C5 C6 0.4(3) . . . . ?
O3 C4 C5 C7 -0.5(4) . . . . ?
C2 C4 C5 C7 -179.3(2) . . . . ?
C3 N3 C6 C10 177.8(2) . . . . ?
C11 N3 C6 C10 3.1(4) . . . . ?
C3 N3 C6 C5 -3.5(3) . . . . ?
C11 N3 C6 C5 -178.2(2) . . . . ?
C7 C5 C6 N3 -177.7(2) . . . . ?
C4 C5 C6 N3 2.5(4) . . . . ?
C7 C5 C6 C10 1.0(4) . . . . ?
C4 C5 C6 C10 -178.7(2) . . . . ?
C6 C5 C7 C8 -1.7(4) . . . . ?
C4 C5 C7 C8 178.0(2) . . . . ?
C5 C7 C8 F1 -175.6(2) . . . . ?
C5 C7 C8 C9 0.6(4) . . . . ?
C13 N4 C9 C10 125.0(3) . . . . ?
C15 N4 C9 C10 -11.1(4) . . . . ?
C13 N4 C9 C8 -59.0(3) . . . . ?
C15 N4 C9 C8 165.0(3) . . . . ?
F1 C8 C9 C10 177.5(2) . . . . ?
C7 C8 C9 C10 1.3(4) . . . . ?
F1 C8 C9 N4 1.2(4) . . . . ?
C7 C8 C9 N4 -175.0(3) . . . . ?
N4 C9 C10 C6 174.2(2) . . . . ?
C8 C9 C10 C6 -2.0(4) . . . . ?
N3 C6 C10 C9 179.6(2) . . . . ?
C5 C6 C10 C9 0.9(4) . . . . ?
C3 N3 C11 C12 -92.6(3) . . . . ?
C6 N3 C11 C12 82.3(3) . . . . ?
C9 N4 C13 C14 165.1(2) . . . . ?
C15 N4 C13 C14 -56.6(3) . . . . ?
C16 N5 C14 C13 -59.2(3) . . . . ?
C17 N5 C14 C13 178.3(3) . . . . ?
N4 C13 C14 N5 57.9(3) . . . . ?
C9 N4 C15 C16 -165.0(2) . . . . ?
C13 N4 C15 C16 56.4(3) . . . . ?
C14 N5 C16 C15 59.6(3) . . . . ?
C17 N5 C16 C15 -178.1(2) . . . . ?
N4 C15 C16 N5 -58.2(3) . . . . ?
C22 N1 C18 C19 -0.3(4) . . . . ?
Cu1 N1 C18 C19 176.2(2) . . . . ?
N1 C18 C19 C20 0.1(5) . . . . ?
C18 C19 C20 C21 0.1(5) . . . . ?
C19 C20 C21 C22 -0.1(5) . . . . ?
C18 N1 C22 C21 0.4(4) . . . . ?
Cu1 N1 C22 C21 -176.5(2) . . . . ?
C18 N1 C22 C23 -179.7(2) . . . . ?
Cu1 N1 C22 C23 3.4(3) . . . . ?
C20 C21 C22 N1 -0.2(4) . . . . ?
C20 C21 C22 C23 180.0(3) . . . . ?
C27 N2 C23 C24 -0.2(4) . . . . ?
Cu1 N2 C23 C24 -179.5(2) . . . . ?
C27 N2 C23 C22 179.5(3) . . . . ?
Cu1 N2 C23 C22 0.1(3) . . . . ?
N1 C22 C23 N2 -2.3(3) . . . . ?
C21 C22 C23 N2 177.6(3) . . . . ?
N1 C22 C23 C24 177.3(3) . . . . ?
C21 C22 C23 C24 -2.8(4) . . . . ?
N2 C23 C24 C25 0.7(5) . . . . ?
C22 C23 C24 C25 -178.9(3) . . . . ?
C23 C24 C25 C26 -1.4(5) . . . . ?
C24 C25 C26 C27 1.4(5) . . . . ?
O4 Cu2 N6 C45 7.1(2) . . . . ?
O6 Cu2 N6 C45 110.1(4) . . . . ?
N7 Cu2 N6 C45 176.3(2) . . . . ?
Cl2 Cu2 N6 C45 -89.3(2) . . . . ?
O4 Cu2 N6 C49 -171.74(18) . . . . ?
O6 Cu2 N6 C49 -68.8(4) . . . . ?
N7 Cu2 N6 C49 -2.59(18) . . . . ?
Cl2 Cu2 N6 C49 91.87(18) . . . . ?
O4 Cu2 N7 C54 -128.2(4) . . . . ?
O6 Cu2 N7 C54 -11.7(2) . . . . ?
N6 Cu2 N7 C54 -178.8(2) . . . . ?
Cl2 Cu2 N7 C54 77.7(2) . . . . ?
O4 Cu2 N7 C50 54.5(4) . . . . ?
O6 Cu2 N7 C50 171.01(17) . . . . ?
N6 Cu2 N7 C50 3.86(17) . . . . ?
Cl2 Cu2 N7 C50 -99.62(17) . . . . ?
O6 Cu2 O4 C28 34.9(2) . . . . ?
N7 Cu2 O4 C28 151.5(3) . . . . ?
N6 Cu2 O4 C28 -158.8(2) . . . . ?
Cl2 Cu2 O4 C28 -54.4(2) . . . . ?
O4 Cu2 O6 C31 -31.41(19) . . . . ?
N7 Cu2 O6 C31 161.17(19) . . . . ?
N6 Cu2 O6 C31 -134.1(3) . . . . ?
Cl2 Cu2 O6 C31 64.67(18) . . . . ?
C23 N2 C27 C26 0.2(5) . . . . ?
Cu1 N2 C27 C26 179.5(3) . . . . ?
C25 C26 C27 N2 -0.8(5) . . . . ?
Cu2 O4 C28 O5 157.3(2) . . . . ?
Cu2 O4 C28 C29 -24.0(4) . . . . ?
O5 C28 C29 C30 1.6(4) . . . . ?
O4 C28 C29 C30 -177.1(2) . . . . ?
O5 C28 C29 C31 179.1(3) . . . . ?
O4 C28 C29 C31 0.4(4) . . . . ?
C33 N8 C30 C29 0.4(4) . . . . ?
C38 N8 C30 C29 -174.1(2) . . . . ?
C31 C29 C30 N8 0.1(4) . . . . ?
C28 C29 C30 N8 177.7(2) . . . . ?
Cu2 O6 C31 C29 20.2(3) . . . . ?
Cu2 O6 C31 C32 -159.86(17) . . . . ?
C30 C29 C31 O6 178.1(2) . . . . ?
C28 C29 C31 O6 0.7(4) . . . . ?
C30 C29 C31 C32 -1.8(3) . . . . ?
C28 C29 C31 C32 -179.2(2) . . . . ?
O6 C31 C32 C34 3.1(3) . . . . ?
C29 C31 C32 C34 -177.0(2) . . . . ?
O6 C31 C32 C33 -176.9(2) . . . . ?
C29 C31 C32 C33 3.0(3) . . . . ?
C30 N8 C33 C37 179.6(2) . . . . ?
C38 N8 C33 C37 -6.1(4) . . . . ?
C30 N8 C33 C32 0.7(3) . . . . ?
C38 N8 C33 C32 175.1(2) . . . . ?
C34 C32 C33 N8 177.5(2) . . . . ?
C31 C32 C33 N8 -2.5(3) . . . . ?
C34 C32 C33 C37 -1.4(4) . . . . ?
C31 C32 C33 C37 178.6(2) . . . . ?
C33 C32 C34 C35 0.7(4) . . . . ?
C31 C32 C34 C35 -179.4(2) . . . . ?
C32 C34 C35 F2 176.6(2) . . . . ?
C32 C34 C35 C36 0.8(4) . . . . ?
C42 N9 C36 C37 9.2(4) . . . . ?
C40 N9 C36 C37 -130.4(3) . . . . ?
C42 N9 C36 C35 -165.8(3) . . . . ?
C40 N9 C36 C35 54.6(4) . . . . ?
F2 C35 C36 C37 -177.3(2) . . . . ?
C34 C35 C36 C37 -1.5(4) . . . . ?
F2 C35 C36 N9 -2.0(4) . . . . ?
C34 C35 C36 N9 173.8(3) . . . . ?
N9 C36 C37 C33 -174.4(2) . . . . ?
C35 C36 C37 C33 0.8(4) . . . . ?
N8 C33 C37 C36 -178.2(2) . . . . ?
C32 C33 C37 C36 0.6(4) . . . . ?
C30 N8 C38 C39 93.8(3) . . . . ?
C33 N8 C38 C39 -80.7(3) . . . . ?
C36 N9 C40 C41 -162.2(2) . . . . ?
C42 N9 C40 C41 55.8(3) . . . . ?
C43 N10 C41 C40 61.0(3) . . . . ?
C44 N10 C41 C40 -176.1(3) . . . . ?
N9 C40 C41 N10 -59.0(3) . . . . ?
C36 N9 C42 C43 162.2(3) . . . . ?
C40 N9 C42 C43 -55.2(3) . . . . ?
C41 N10 C43 C42 -61.6(3) . . . . ?
C44 N10 C43 C42 175.2(3) . . . . ?
N9 C42 C43 N10 58.6(4) . . . . ?
C49 N6 C45 C46 1.0(4) . . . . ?
Cu2 N6 C45 C46 -177.8(2) . . . . ?
N6 C45 C46 C47 -0.7(5) . . . . ?
C45 C46 C47 C48 -0.4(5) . . . . ?
C46 C47 C48 C49 1.1(5) . . . . ?
C45 N6 C49 C48 -0.2(4) . . . . ?
Cu2 N6 C49 C48 178.7(2) . . . . ?
C45 N6 C49 C50 -178.0(2) . . . . ?
Cu2 N6 C49 C50 1.0(3) . . . . ?
C47 C48 C49 N6 -0.8(4) . . . . ?
C47 C48 C49 C50 176.7(3) . . . . ?
C54 N7 C50 C51 -2.0(4) . . . . ?
Cu2 N7 C50 C51 175.5(2) . . . . ?
C54 N7 C50 C49 178.1(2) . . . . ?
Cu2 N7 C50 C49 -4.4(3) . . . . ?
N6 C49 C50 N7 2.2(3) . . . . ?
C48 C49 C50 N7 -175.4(2) . . . . ?
N6 C49 C50 C51 -177.7(2) . . . . ?
C48 C49 C50 C51 4.6(4) . . . . ?
N7 C50 C51 C52 2.0(4) . . . . ?
C49 C50 C51 C52 -178.1(3) . . . . ?
C50 C51 C52 C53 -0.6(5) . . . . ?
C51 C52 C53 C54 -0.8(5) . . . . ?
C50 N7 C54 C53 0.5(4) . . . . ?
Cu2 N7 C54 C53 -176.7(2) . . . . ?
C52 C53 C54 N7 0.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7A N10 0.82 2.00 2.807(3) 165.1 .
O7 H7B O2 0.817(10) 2.153(19) 2.938(3) 161(5) 1_655
O8 H8A O7 0.82 2.01 2.789(4) 158.8 .
O8 H8B O15 0.815(10) 2.28(6) 2.896(5) 133(7) 4_665
O9 H9A O8 0.823(10) 2.063(19) 2.865(5) 165(6) .
O9 H9B Cl1 0.819(10) 2.59(3) 3.355(3) 157(6) 2_646
O10 H10A Cl2 0.821(10) 2.414(15) 3.224(4) 169(6) .
O10 H10B O12 0.818(10) 2.323(17) 3.125(5) 167(6) 1_655
O11 H11C O2 0.821(10) 2.24(2) 2.996(3) 153(4) .
O11 H11D O10 0.819(10) 1.996(15) 2.803(4) 168(5) 3_566
O12 H12D N5 0.818(10) 2.024(14) 2.833(4) 170(6) .
O12 H12E O5 0.823(10) 2.191(19) 2.989(4) 163(5) 1_455
O13 H13C O12 0.818(10) 2.114(18) 2.909(4) 164(5) 2_446
O13 H13D O11 0.818(10) 2.114(12) 2.929(4) 175(6) .
O14 H14C Cl2 0.815(10) 2.69(3) 3.427(4) 152(6) .
O14 H14D O13 0.822(10) 2.075(12) 2.896(5) 177(7) 1_655
O15 H15 Cl1 0.82 2.32 3.129(4) 171.0 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.527
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.064
