#------------------------------------------------------------------------------
#$Date: 2021-01-07 08:43:45 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260800 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/96/1559689.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1559689
loop_
_publ_author_name
'Guo, Rui-Feng'
'Yan, Hou-Tian'
'Liu, Rui-Xue'
'Li, Hong-Chang'
'Liu, Yan-Cheng'
'Chen, Zhen-Feng'
'Liang, Hong'
_publ_section_title
;
 Structural characterization and pharmacological assessment in
 vitro/in vivo of a new copper(II)-based derivative of
 enrofloxacin.
;
_journal_issue                   12
_journal_name_full               'Metallomics : integrated biometal science'
_journal_page_first              2145
_journal_page_last               2160
_journal_paper_doi               10.1039/d0mt00155d
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         'C38 H44 Cu F2 N6 O7, 6.33(H2 O)'
_chemical_formula_sum            'C38 H56.67 Cu F2 N6 O13.34'
_chemical_formula_weight         912.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-29 deposited with the CCDC.	2020-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                111.747(10)
_cell_angle_beta                 92.860(10)
_cell_angle_gamma                113.294(9)
_cell_formula_units_Z            2
_cell_length_a                   12.151(7)
_cell_length_b                   13.362(8)
_cell_length_c                   16.110(10)
_cell_measurement_reflns_used    3477
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.28
_cell_measurement_theta_min      2.58
_cell_volume                     2172(2)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26583
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.398
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       block
_exptl_crystal_F_000             961
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.765
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         8847
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1082P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1573
_refine_ls_wR_factor_ref         0.1893
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5521
_reflns_number_total             8847
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0mt00155d2.cif
_cod_data_source_block           bbbbbb
_cod_depositor_comments          'Adding full bibliography for 1559689.cif.'
_cod_database_code               1559689
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.827
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 H7B-H9A = H7B-H9B
 2.2 with sigma of 0.02
 O5-H10A
 2 with sigma of 0.02
 H10B-O11
 2.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O14) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: O14(0.33333) H14C(0.33333) H14D(0.33333)
 Fixed X: H10A(0.42179) H10B(0.41348) H14C(0.801081) H14D(0.86165)
 Fixed Y: H10A(0.334539) H10B(0.385321) H14C(0.46972) H14D(0.453489)
 Fixed Z: H10A(0.50086) H10B(0.44422) H14C(0.55428) H14D(0.486659)
5.a Free rotating group:
 O8(H8A,H8B), O9(H9A,H9B), O11(H11A,H11B), O12(H12A,H12B), O13(H13A,H13B)
5.b Rotating group:
 O7(H7A,H7B)
5.c Ternary CH refined with riding coordinates:
 C3(H3), C22(H22)
5.d Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B),
 C17(H17A,H17B), C18(H18A,H18B), C20(H20A,H20B), C21(H21A,H21B), C33(H33A,H33B),
  C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B)
5.e Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C13(H13), C25(H25), C29(H29), C32(H32)
5.f Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C38(H38A,H38B,H38C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.38915(4) 0.25993(5) 0.69120(3) 0.03610(18) Uani 1 1 d . . . . .
F1 F 0.0266(2) 0.2318(3) 0.34374(17) 0.0582(7) Uani 1 1 d . . . . .
F2 F 0.7375(2) 0.2408(2) 1.02135(15) 0.0504(6) Uani 1 1 d . . . . .
O1 O 0.1209(3) 0.1028(3) 0.80702(19) 0.0555(9) Uani 1 1 d . . . . .
O2 O 0.2887(2) 0.1947(3) 0.76476(17) 0.0426(7) Uani 1 1 d . . . . .
O3 O 0.2465(2) 0.2266(2) 0.60581(17) 0.0361(6) Uani 1 1 d . . . . .
O4 O 0.6373(3) 0.3122(4) 0.5327(2) 0.0762(12) Uani 1 1 d . . . . .
O5 O 0.4798(2) 0.2758(3) 0.59736(18) 0.0485(8) Uani 1 1 d D . . . .
O6 O 0.5253(2) 0.2664(3) 0.76608(17) 0.0384(6) Uani 1 1 d . . . . .
O7 O 0.4400(3) 0.4534(3) 0.7685(2) 0.0725(10) Uani 1 1 d . . . . .
H7A H 0.413171 0.467708 0.819849 0.109 Uiso 1 1 d GR . . . .
H7B H 0.401135 0.477264 0.737708 0.109 Uiso 1 1 d DGR . . . .
N1 N -0.1206(3) 0.0556(3) 0.59853(19) 0.0295(7) Uani 1 1 d . . . . .
N2 N -0.2244(3) 0.1241(3) 0.3344(2) 0.0365(8) Uani 1 1 d . . . . .
N3 N -0.4145(3) 0.1248(3) 0.2214(2) 0.0382(8) Uani 1 1 d . . . . .
N4 N 0.8814(3) 0.3614(3) 0.7399(2) 0.0307(7) Uani 1 1 d . . . . .
N5 N 0.9767(3) 0.2932(3) 1.0072(2) 0.0359(8) Uani 1 1 d . . . . .
N6 N 1.1468(3) 0.2561(3) 1.1088(2) 0.0379(8) Uani 1 1 d . . . . .
C1 C -0.3424(4) 0.0225(4) 0.6037(3) 0.0429(10) Uani 1 1 d . . . . .
H1A H -0.315715 0.107368 0.620011 0.052 Uiso 1 1 calc R . . . .
H1B H -0.424964 -0.030374 0.565308 0.052 Uiso 1 1 calc R . . . .
C2 C -0.2984(4) -0.0113(4) 0.6728(3) 0.0457(10) Uani 1 1 d . . . . .
H2A H -0.245128 0.053258 0.731027 0.055 Uiso 1 1 calc R . . . .
H2B H -0.354339 -0.084437 0.676343 0.055 Uiso 1 1 calc R . . . .
C3 C -0.2478(3) -0.0236(3) 0.5893(3) 0.0316(8) Uani 1 1 d . . . . .
H3 H -0.277911 -0.106365 0.542518 0.038 Uiso 1 1 calc R . . . .
C4 C 0.1713(3) 0.1436(4) 0.7544(2) 0.0343(9) Uani 1 1 d . . . . .
C5 C 0.0913(3) 0.1317(3) 0.6741(2) 0.0298(8) Uani 1 1 d . . . . .
C6 C -0.0332(3) 0.0718(3) 0.6644(2) 0.0312(8) Uani 1 1 d . . . . .
H6 H -0.059741 0.040013 0.706208 0.037 Uiso 1 1 calc R . . . .
C7 C -0.0851(3) 0.1019(3) 0.5343(2) 0.0276(8) Uani 1 1 d . . . . .
C8 C 0.0413(3) 0.1619(3) 0.5391(2) 0.0271(8) Uani 1 1 d . . . . .
C9 C 0.1347(3) 0.1765(3) 0.6085(2) 0.0281(8) Uani 1 1 d . . . . .
C10 C -0.1734(3) 0.0897(3) 0.4667(2) 0.0315(8) Uani 1 1 d . . . . .
H10 H -0.256604 0.049053 0.464345 0.038 Uiso 1 1 calc R . . . .
C11 C -0.1391(3) 0.1371(3) 0.4034(2) 0.0320(8) Uani 1 1 d . . . . .
C12 C -0.0119(3) 0.1935(4) 0.4083(3) 0.0370(9) Uani 1 1 d . . . . .
C13 C 0.0760(3) 0.2070(3) 0.4734(2) 0.0335(9) Uani 1 1 d . . . . .
H13 H 0.158903 0.246030 0.474218 0.040 Uiso 1 1 calc R . . . .
C14 C -0.3542(3) 0.0494(4) 0.3254(3) 0.0375(9) Uani 1 1 d . . . . .
H14A H -0.383898 0.092756 0.374328 0.045 Uiso 1 1 calc R . . . .
H14B H -0.363988 -0.023462 0.330715 0.045 Uiso 1 1 calc R . . . .
C15 C -0.4282(4) 0.0173(4) 0.2337(3) 0.0413(10) Uani 1 1 d . . . . .
H15A H -0.401629 -0.030407 0.185236 0.050 Uiso 1 1 calc R . . . .
H15B H -0.514443 -0.031270 0.228776 0.050 Uiso 1 1 calc R . . . .
C16 C -0.2854(4) 0.1931(5) 0.2268(3) 0.0552(13) Uani 1 1 d . . . . .
H16A H -0.273401 0.264617 0.218306 0.066 Uiso 1 1 calc R . . . .
H16B H -0.259416 0.144885 0.178131 0.066 Uiso 1 1 calc R . . . .
C17 C -0.2078(4) 0.2295(4) 0.3190(3) 0.0480(11) Uani 1 1 d . . . . .
H17A H -0.121709 0.274667 0.321191 0.058 Uiso 1 1 calc R . . . .
H17B H -0.230905 0.281266 0.367377 0.058 Uiso 1 1 calc R . . . .
C18 C -0.4932(5) 0.0909(5) 0.1336(3) 0.0647(14) Uani 1 1 d . . . . .
H18A H -0.575715 0.032852 0.128278 0.078 Uiso 1 1 calc R . . . .
H18B H -0.461841 0.052055 0.083572 0.078 Uiso 1 1 calc R . . . .
C19 C -0.4998(5) 0.1950(6) 0.1238(4) 0.0816(19) Uani 1 1 d . . . . .
H19A H -0.563567 0.166148 0.071259 0.122 Uiso 1 1 calc GR . . . .
H19B H -0.422304 0.244470 0.115961 0.122 Uiso 1 1 calc GR . . . .
H19C H -0.517906 0.241662 0.177961 0.122 Uiso 1 1 calc GR . . . .
C20 C 1.1068(4) 0.5136(4) 0.7952(3) 0.0513(11) Uani 1 1 d . . . . .
H20A H 1.083440 0.566360 0.842478 0.062 Uiso 1 1 calc R . . . .
H20B H 1.186705 0.518366 0.813447 0.062 Uiso 1 1 calc R . . . .
C21 C 1.0660(4) 0.4897(5) 0.6989(3) 0.0589(13) Uani 1 1 d . . . . .
H21A H 1.017963 0.528437 0.687394 0.071 Uiso 1 1 calc R . . . .
H21B H 1.121133 0.480487 0.658389 0.071 Uiso 1 1 calc R . . . .
C22 C 1.0082(3) 0.3951(4) 0.7296(3) 0.0354(9) Uani 1 1 d . . . . .
H22 H 1.031628 0.329095 0.707958 0.042 Uiso 1 1 calc R . . . .
C23 C 0.5929(4) 0.3026(4) 0.5979(3) 0.0397(10) Uani 1 1 d . . . . .
C24 C 0.6755(3) 0.3197(3) 0.6797(2) 0.0319(8) Uani 1 1 d . . . . .
C25 C 0.7972(3) 0.3521(3) 0.6770(2) 0.0319(8) Uani 1 1 d . . . . .
H25 H 0.822837 0.368640 0.628089 0.038 Uiso 1 1 calc R . . . .
C26 C 0.8474(3) 0.3326(3) 0.8130(2) 0.0279(8) Uani 1 1 d . . . . .
C27 C 0.7249(3) 0.3018(3) 0.8216(2) 0.0292(8) Uani 1 1 d . . . . .
C28 C 0.6341(3) 0.2960(3) 0.7550(2) 0.0288(8) Uani 1 1 d . . . . .
C29 C 0.9312(3) 0.3285(3) 0.8732(2) 0.0330(8) Uani 1 1 d . . . . .
H29 H 1.011538 0.348583 0.866008 0.040 Uiso 1 1 calc R . . . .
C30 C 0.8969(3) 0.2952(3) 0.9431(2) 0.0319(8) Uani 1 1 d . . . . .
C31 C 0.7740(3) 0.2683(4) 0.9513(2) 0.0340(9) Uani 1 1 d . . . . .
C32 C 0.6906(3) 0.2716(3) 0.8936(2) 0.0317(8) Uani 1 1 d . . . . .
H32 H 0.611177 0.253673 0.902355 0.038 Uiso 1 1 calc R . . . .
C33 C 1.1083(3) 0.3484(4) 1.0098(3) 0.0381(9) Uani 1 1 d . . . . .
H33A H 1.131905 0.424839 1.006223 0.046 Uiso 1 1 calc R . . . .
H33B H 1.126319 0.296292 0.957801 0.046 Uiso 1 1 calc R . . . .
C34 C 1.1804(4) 0.3681(4) 1.0989(3) 0.0406(10) Uani 1 1 d . . . . .
H34A H 1.267699 0.404139 1.100697 0.049 Uiso 1 1 calc R . . . .
H34B H 1.165288 0.423932 1.150266 0.049 Uiso 1 1 calc R . . . .
C35 C 1.0144(4) 0.2016(4) 1.1046(3) 0.0445(10) Uani 1 1 d . . . . .
H35A H 0.996485 0.254689 1.156076 0.053 Uiso 1 1 calc R . . . .
H35B H 0.990368 0.125952 1.109460 0.053 Uiso 1 1 calc R . . . .
C36 C 0.9412(4) 0.1796(4) 1.0163(3) 0.0442(10) Uani 1 1 d . . . . .
H36A H 0.955774 0.123345 0.964844 0.053 Uiso 1 1 calc R . . . .
H36B H 0.854105 0.144276 1.015164 0.053 Uiso 1 1 calc R . . . .
C37 C 1.2193(4) 0.2798(4) 1.1960(3) 0.0509(12) Uani 1 1 d . . . . .
H37A H 1.194677 0.326685 1.246596 0.061 Uiso 1 1 calc R . . . .
H37B H 1.305639 0.327843 1.200805 0.061 Uiso 1 1 calc R . . . .
C38 C 1.2046(5) 0.1671(5) 1.2053(4) 0.0675(15) Uani 1 1 d . . . . .
H38A H 1.217770 0.114812 1.151320 0.101 Uiso 1 1 calc GR . . . .
H38B H 1.122957 0.126477 1.212281 0.101 Uiso 1 1 calc GR . . . .
H38C H 1.263684 0.188215 1.258193 0.101 Uiso 1 1 calc GR . . . .
O8 O 0.3627(4) 0.4954(4) 0.9346(3) 0.0806(11) Uani 1 1 d . . . . .
H8A H 0.425604 0.560958 0.968051 0.121 Uiso 1 1 d G . . . .
H8B H 0.368154 0.444208 0.951722 0.121 Uiso 1 1 d G . . . .
O9 O 0.3344(5) 0.5005(5) 0.6419(4) 0.1133(16) Uani 1 1 d . . . . .
H9A H 0.353998 0.456688 0.597828 0.170 Uiso 1 1 d DG . . . .
H9B H 0.388530 0.571915 0.656080 0.170 Uiso 1 1 d DG . . . .
O10 O 0.3728(4) 0.3516(5) 0.4753(4) 0.1200(17) Uani 1 1 d . . . . .
H10A H 0.421790 0.334539 0.500860 0.180 Uiso 1 1 d DR . . . .
H10B H 0.413480 0.385321 0.444220 0.180 Uiso 1 1 d DR . . . .
O11 O 0.5290(4) 0.2838(4) 0.3663(2) 0.0694(10) Uani 1 1 d D . . . .
H11A H 0.564895 0.284648 0.413362 0.104 Uiso 1 1 d G . . . .
H11B H 0.538191 0.231511 0.321112 0.104 Uiso 1 1 d G . . . .
O12 O 0.4229(3) 0.2994(3) 0.9488(2) 0.0699(10) Uani 1 1 d . . . . .
H12A H 0.374134 0.242627 0.960281 0.105 Uiso 1 1 d G . . . .
H12B H 0.400702 0.274175 0.890981 0.105 Uiso 1 1 d G . . . .
O13 O 0.2277(3) 0.1092(4) 0.9669(2) 0.0632(9) Uani 1 1 d . . . . .
H13A H 0.191162 0.100090 0.916352 0.095 Uiso 1 1 d G . . . .
H13B H 0.200737 0.149382 1.007491 0.095 Uiso 1 1 d G . . . .
O14 O 0.869(2) 0.5047(17) 0.5375(13) 0.173(8) Uani 0.3333 1 d . U P . .
H14C H 0.801081 0.469720 0.554280 0.259 Uiso 0.3333 1 d R . P . .
H14D H 0.861650 0.453489 0.486659 0.259 Uiso 0.3333 1 d R . P . .
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'
Cu Cu 0.3201 1.2651 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O3 92.59(11) . . ?
O2 Cu1 O5 162.92(13) . . ?
O2 Cu1 O6 85.81(11) . . ?
O2 Cu1 O7 100.34(14) . . ?
O3 Cu1 O6 170.92(12) . . ?
O3 Cu1 O7 95.08(13) . . ?
O5 Cu1 O3 86.67(11) . . ?
O5 Cu1 O6 92.24(11) . . ?
O5 Cu1 O7 96.72(14) . . ?
O6 Cu1 O7 94.00(13) . . ?
C4 O2 Cu1 131.4(2) . . ?
C9 O3 Cu1 126.6(2) . . ?
C23 O5 Cu1 130.6(2) . . ?
C28 O6 Cu1 126.4(2) . . ?
Cu1 O7 H7A 111.6 . . ?
Cu1 O7 H7B 110.7 . . ?
H7A O7 H7B 102.5 . . ?
C6 N1 C3 118.4(3) . . ?
C6 N1 C7 119.5(3) . . ?
C7 N1 C3 121.5(3) . . ?
C11 N2 C14 117.4(3) . . ?
C11 N2 C17 118.8(3) . . ?
C17 N2 C14 111.0(3) . . ?
C15 N3 C18 110.8(3) . . ?
C16 N3 C15 107.6(3) . . ?
C16 N3 C18 112.1(3) . . ?
C25 N4 C22 119.9(3) . . ?
C25 N4 C26 120.4(3) . . ?
C26 N4 C22 119.6(3) . . ?
C30 N5 C33 117.5(3) . . ?
C30 N5 C36 117.5(3) . . ?
C33 N5 C36 110.2(3) . . ?
C34 N6 C35 108.6(3) . . ?
C34 N6 C37 110.2(3) . . ?
C35 N6 C37 111.3(3) . . ?
H1A C1 H1B 114.9 . . ?
C2 C1 H1A 117.8 . . ?
C2 C1 H1B 117.8 . . ?
C2 C1 C3 59.7(3) . . ?
C3 C1 H1A 117.8 . . ?
C3 C1 H1B 117.8 . . ?
C1 C2 H2A 117.8 . . ?
C1 C2 H2B 117.8 . . ?
H2A C2 H2B 114.9 . . ?
C3 C2 C1 60.2(3) . . ?
C3 C2 H2A 117.8 . . ?
C3 C2 H2B 117.8 . . ?
N1 C3 C1 121.2(3) . . ?
N1 C3 C2 119.3(3) . . ?
N1 C3 H3 115.1 . . ?
C1 C3 H3 115.1 . . ?
C2 C3 C1 60.1(3) . . ?
C2 C3 H3 115.1 . . ?
O1 C4 O2 123.2(3) . . ?
O1 C4 C5 118.2(3) . . ?
O2 C4 C5 118.6(3) . . ?
C6 C5 C4 116.0(3) . . ?
C6 C5 C9 118.8(3) . . ?
C9 C5 C4 125.2(3) . . ?
N1 C6 C5 125.0(3) . . ?
N1 C6 H6 117.5 . . ?
C5 C6 H6 117.5 . . ?
N1 C7 C8 118.4(3) . . ?
N1 C7 C10 120.9(3) . . ?
C8 C7 C10 120.6(3) . . ?
C7 C8 C9 121.8(3) . . ?
C7 C8 C13 118.0(3) . . ?
C13 C8 C9 120.2(3) . . ?
O3 C9 C5 125.5(3) . . ?
O3 C9 C8 118.2(3) . . ?
C5 C9 C8 116.3(3) . . ?
C7 C10 H10 119.3 . . ?
C11 C10 C7 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
N2 C11 C12 120.6(3) . . ?
C10 C11 N2 122.7(3) . . ?
C10 C11 C12 116.5(3) . . ?
F1 C12 C11 119.3(3) . . ?
F1 C12 C13 117.3(3) . . ?
C13 C12 C11 123.3(3) . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.1(3) . . ?
C12 C13 H13 119.9 . . ?
N2 C14 H14A 109.7 . . ?
N2 C14 H14B 109.7 . . ?
N2 C14 C15 109.8(3) . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
N3 C15 C14 111.9(3) . . ?
N3 C15 H15A 109.2 . . ?
N3 C15 H15B 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
N3 C16 C17 110.6(3) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
N2 C17 C16 111.0(4) . . ?
N2 C17 H17A 109.4 . . ?
N2 C17 H17B 109.4 . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
N3 C18 H18A 108.9 . . ?
N3 C18 H18B 108.9 . . ?
N3 C18 C19 113.4(4) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H20A C20 H20B 115.0 . . ?
C21 C20 H20A 117.9 . . ?
C21 C20 H20B 117.9 . . ?
C21 C20 C22 59.2(3) . . ?
C22 C20 H20A 117.9 . . ?
C22 C20 H20B 117.9 . . ?
C20 C21 H21A 117.7 . . ?
C20 C21 H21B 117.7 . . ?
H21A C21 H21B 114.8 . . ?
C22 C21 C20 60.5(3) . . ?
C22 C21 H21A 117.7 . . ?
C22 C21 H21B 117.7 . . ?
N4 C22 C20 119.2(3) . . ?
N4 C22 H22 115.6 . . ?
C20 C22 H22 115.6 . . ?
C21 C22 N4 119.2(3) . . ?
C21 C22 C20 60.3(3) . . ?
C21 C22 H22 115.6 . . ?
O4 C23 O5 122.6(3) . . ?
O4 C23 C24 118.0(3) . . ?
O5 C23 C24 119.3(3) . . ?
C25 C24 C23 116.4(3) . . ?
C25 C24 C28 119.0(3) . . ?
C28 C24 C23 124.5(3) . . ?
N4 C25 C24 124.4(3) . . ?
N4 C25 H25 117.8 . . ?
C24 C25 H25 117.8 . . ?
N4 C26 C27 118.2(3) . . ?
N4 C26 C29 120.9(3) . . ?
C29 C26 C27 120.8(3) . . ?
C26 C27 C28 121.4(3) . . ?
C32 C27 C26 118.2(3) . . ?
C32 C27 C28 120.4(3) . . ?
O6 C28 C24 125.3(3) . . ?
O6 C28 C27 118.2(3) . . ?
C24 C28 C27 116.4(3) . . ?
C26 C29 H29 119.4 . . ?
C30 C29 C26 121.3(3) . . ?
C30 C29 H29 119.4 . . ?
N5 C30 C31 119.5(3) . . ?
C29 C30 N5 124.1(3) . . ?
C29 C30 C31 116.3(3) . . ?
F2 C31 C30 118.6(3) . . ?
F2 C31 C32 117.8(3) . . ?
C32 C31 C30 123.6(3) . . ?
C27 C32 H32 120.1 . . ?
C31 C32 C27 119.8(3) . . ?
C31 C32 H32 120.1 . . ?
N5 C33 H33A 109.9 . . ?
N5 C33 H33B 109.9 . . ?
N5 C33 C34 108.9(3) . . ?
H33A C33 H33B 108.3 . . ?
C34 C33 H33A 109.9 . . ?
C34 C33 H33B 109.9 . . ?
N6 C34 C33 112.3(3) . . ?
N6 C34 H34A 109.1 . . ?
N6 C34 H34B 109.1 . . ?
C33 C34 H34A 109.1 . . ?
C33 C34 H34B 109.1 . . ?
H34A C34 H34B 107.9 . . ?
N6 C35 H35A 109.4 . . ?
N6 C35 H35B 109.4 . . ?
N6 C35 C36 111.0(3) . . ?
H35A C35 H35B 108.0 . . ?
C36 C35 H35A 109.4 . . ?
C36 C35 H35B 109.4 . . ?
N5 C36 C35 110.4(3) . . ?
N5 C36 H36A 109.6 . . ?
N5 C36 H36B 109.6 . . ?
C35 C36 H36A 109.6 . . ?
C35 C36 H36B 109.6 . . ?
H36A C36 H36B 108.1 . . ?
N6 C37 H37A 108.8 . . ?
N6 C37 H37B 108.8 . . ?
N6 C37 C38 113.7(4) . . ?
H37A C37 H37B 107.7 . . ?
C38 C37 H37A 108.8 . . ?
C38 C37 H37B 108.8 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
H8A O8 H8B 104.5 . . ?
H9A O9 H9B 104.5 . . ?
H10A O10 H10B 104.6(5) . . ?
H11A O11 H11B 104.5 . . ?
H12A O12 H12B 104.5 . . ?
H13A O13 H13B 104.6 . . ?
H14C O14 H14D 103.6(19) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.929(3) . ?
Cu1 O3 1.947(3) . ?
Cu1 O5 1.940(3) . ?
Cu1 O6 1.952(3) . ?
Cu1 O7 2.212(4) . ?
F1 C12 1.348(4) . ?
F2 C31 1.354(4) . ?
O1 C4 1.232(5) . ?
O2 C4 1.286(4) . ?
O3 C9 1.267(4) . ?
O4 C23 1.229(5) . ?
O5 C23 1.274(5) . ?
O6 C28 1.265(4) . ?
O7 H7A 0.8869 . ?
O7 H7B 0.8849 . ?
N1 C3 1.448(4) . ?
N1 C6 1.354(4) . ?
N1 C7 1.395(4) . ?
N2 C11 1.393(4) . ?
N2 C14 1.460(5) . ?
N2 C17 1.457(5) . ?
N3 C15 1.468(5) . ?
N3 C16 1.448(5) . ?
N3 C18 1.473(5) . ?
N4 C22 1.461(4) . ?
N4 C25 1.339(4) . ?
N4 C26 1.402(5) . ?
N5 C30 1.395(4) . ?
N5 C33 1.463(5) . ?
N5 C36 1.471(5) . ?
N6 C34 1.460(5) . ?
N6 C35 1.466(5) . ?
N6 C37 1.475(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.494(6) . ?
C1 C3 1.495(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.487(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.498(5) . ?
C5 C6 1.371(5) . ?
C5 C9 1.423(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.406(5) . ?
C7 C10 1.407(5) . ?
C8 C9 1.454(5) . ?
C8 C13 1.406(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(5) . ?
C11 C12 1.409(5) . ?
C12 C13 1.367(5) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.506(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.514(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.489(8) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.478(6) . ?
C20 C22 1.481(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.460(6) . ?
C22 H22 0.9800 . ?
C23 C24 1.504(5) . ?
C24 C25 1.375(5) . ?
C24 C28 1.430(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.407(5) . ?
C26 C29 1.403(5) . ?
C27 C28 1.458(5) . ?
C27 C32 1.395(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.382(5) . ?
C30 C31 1.416(5) . ?
C31 C32 1.364(5) . ?
C32 H32 0.9300 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.520(5) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.504(5) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 C38 1.510(7) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
O8 H8A 0.8498 . ?
O8 H8B 0.8499 . ?
O9 H9A 0.8494 . ?
O9 H9B 0.8503 . ?
O10 H10A 0.854(5) . ?
O10 H10B 0.844(5) . ?
O11 H11A 0.8498 . ?
O11 H11B 0.8498 . ?
O12 H12A 0.8490 . ?
O12 H12B 0.8508 . ?
O13 H13A 0.8496 . ?
O13 H13B 0.8506 . ?
O14 H14C 0.89(2) . ?
O14 H14D 0.82(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
Cu1 O2 C4 O1 177.6(3) . . . . ?
Cu1 O2 C4 C5 -1.8(6) . . . . ?
Cu1 O3 C9 C5 -1.7(5) . . . . ?
Cu1 O3 C9 C8 178.7(2) . . . . ?
Cu1 O5 C23 O4 -178.0(4) . . . . ?
Cu1 O5 C23 C24 4.0(6) . . . . ?
Cu1 O6 C28 C24 -6.2(5) . . . . ?
Cu1 O6 C28 C27 176.6(2) . . . . ?
F1 C12 C13 C8 -175.9(4) . . . . ?
F2 C31 C32 C27 178.8(3) . . . . ?
O1 C4 C5 C6 -2.1(5) . . . . ?
O1 C4 C5 C9 178.3(4) . . . . ?
O2 C4 C5 C6 177.3(4) . . . . ?
O2 C4 C5 C9 -2.3(6) . . . . ?
O4 C23 C24 C25 3.8(6) . . . . ?
O4 C23 C24 C28 -171.3(4) . . . . ?
O5 C23 C24 C25 -178.1(4) . . . . ?
O5 C23 C24 C28 6.8(6) . . . . ?
N1 C7 C8 C9 0.1(5) . . . . ?
N1 C7 C8 C13 179.2(3) . . . . ?
N1 C7 C10 C11 179.0(3) . . . . ?
N2 C11 C12 F1 -2.0(6) . . . . ?
N2 C11 C12 C13 -178.8(4) . . . . ?
N2 C14 C15 N3 -58.1(4) . . . . ?
N3 C16 C17 N2 58.7(5) . . . . ?
N4 C26 C27 C28 1.9(5) . . . . ?
N4 C26 C27 C32 179.2(3) . . . . ?
N4 C26 C29 C30 -177.2(3) . . . . ?
N5 C30 C31 F2 -0.3(5) . . . . ?
N5 C30 C31 C32 178.0(4) . . . . ?
N5 C33 C34 N6 58.4(4) . . . . ?
N6 C35 C36 N5 -58.8(5) . . . . ?
C1 C2 C3 N1 111.3(4) . . . . ?
C2 C1 C3 N1 -108.2(4) . . . . ?
C3 N1 C6 C5 171.6(4) . . . . ?
C3 N1 C7 C8 -169.9(3) . . . . ?
C3 N1 C7 C10 10.5(5) . . . . ?
C4 C5 C6 N1 177.4(3) . . . . ?
C4 C5 C9 O3 4.2(6) . . . . ?
C4 C5 C9 C8 -176.2(3) . . . . ?
C6 N1 C3 C1 117.9(4) . . . . ?
C6 N1 C3 C2 47.0(5) . . . . ?
C6 N1 C7 C8 1.5(5) . . . . ?
C6 N1 C7 C10 -178.1(3) . . . . ?
C6 C5 C9 O3 -175.4(4) . . . . ?
C6 C5 C9 C8 4.2(5) . . . . ?
C7 N1 C3 C1 -70.6(5) . . . . ?
C7 N1 C3 C2 -141.5(4) . . . . ?
C7 N1 C6 C5 -0.1(6) . . . . ?
C7 C8 C9 O3 176.7(3) . . . . ?
C7 C8 C9 C5 -2.9(5) . . . . ?
C7 C8 C13 C12 1.0(6) . . . . ?
C7 C10 C11 N2 178.5(3) . . . . ?
C7 C10 C11 C12 2.4(5) . . . . ?
C8 C7 C10 C11 -0.6(5) . . . . ?
C9 C5 C6 N1 -2.9(6) . . . . ?
C9 C8 C13 C12 -179.8(4) . . . . ?
C10 C7 C8 C9 179.7(3) . . . . ?
C10 C7 C8 C13 -1.2(5) . . . . ?
C10 C11 C12 F1 174.2(4) . . . . ?
C10 C11 C12 C13 -2.7(6) . . . . ?
C11 N2 C14 C15 -164.2(3) . . . . ?
C11 N2 C17 C16 164.1(4) . . . . ?
C11 C12 C13 C8 1.0(6) . . . . ?
C13 C8 C9 O3 -2.4(5) . . . . ?
C13 C8 C9 C5 177.9(3) . . . . ?
C14 N2 C11 C10 -4.8(6) . . . . ?
C14 N2 C11 C12 171.1(4) . . . . ?
C14 N2 C17 C16 -55.3(5) . . . . ?
C15 N3 C16 C17 -59.7(5) . . . . ?
C15 N3 C18 C19 170.3(4) . . . . ?
C16 N3 C15 C14 60.4(4) . . . . ?
C16 N3 C18 C19 -69.5(6) . . . . ?
C17 N2 C11 C10 133.4(4) . . . . ?
C17 N2 C11 C12 -50.7(5) . . . . ?
C17 N2 C14 C15 54.5(4) . . . . ?
C18 N3 C15 C14 -176.7(4) . . . . ?
C18 N3 C16 C17 178.3(4) . . . . ?
C20 C21 C22 N4 108.9(4) . . . . ?
C21 C20 C22 N4 -108.9(4) . . . . ?
C22 N4 C25 C24 179.2(3) . . . . ?
C22 N4 C26 C27 179.4(3) . . . . ?
C22 N4 C26 C29 -3.9(5) . . . . ?
C23 C24 C25 N4 -174.2(3) . . . . ?
C23 C24 C28 O6 -5.6(6) . . . . ?
C23 C24 C28 C27 171.7(3) . . . . ?
C25 N4 C22 C20 111.7(4) . . . . ?
C25 N4 C22 C21 41.4(5) . . . . ?
C25 N4 C26 C27 -4.2(5) . . . . ?
C25 N4 C26 C29 172.6(3) . . . . ?
C25 C24 C28 O6 179.5(3) . . . . ?
C25 C24 C28 C27 -3.3(5) . . . . ?
C26 N4 C22 C20 -71.8(5) . . . . ?
C26 N4 C22 C21 -142.1(4) . . . . ?
C26 N4 C25 C24 2.8(6) . . . . ?
C26 C27 C28 O6 179.2(3) . . . . ?
C26 C27 C28 C24 1.8(5) . . . . ?
C26 C27 C32 C31 -2.4(5) . . . . ?
C26 C29 C30 N5 -177.7(3) . . . . ?
C26 C29 C30 C31 -1.3(5) . . . . ?
C27 C26 C29 C30 -0.6(5) . . . . ?
C28 C24 C25 N4 1.2(6) . . . . ?
C28 C27 C32 C31 174.9(3) . . . . ?
C29 C26 C27 C28 -174.9(3) . . . . ?
C29 C26 C27 C32 2.4(5) . . . . ?
C29 C30 C31 F2 -176.9(3) . . . . ?
C29 C30 C31 C32 1.3(6) . . . . ?
C30 N5 C33 C34 164.4(3) . . . . ?
C30 N5 C36 C35 -163.1(3) . . . . ?
C30 C31 C32 C27 0.5(6) . . . . ?
C32 C27 C28 O6 2.0(5) . . . . ?
C32 C27 C28 C24 -175.4(3) . . . . ?
C33 N5 C30 C29 10.5(5) . . . . ?
C33 N5 C30 C31 -165.8(4) . . . . ?
C33 N5 C36 C35 58.6(4) . . . . ?
C34 N6 C35 C36 57.5(4) . . . . ?
C34 N6 C37 C38 -171.2(4) . . . . ?
C35 N6 C34 C33 -58.0(4) . . . . ?
C35 N6 C37 C38 68.2(5) . . . . ?
C36 N5 C30 C29 -124.8(4) . . . . ?
C36 N5 C30 C31 58.9(5) . . . . ?
C36 N5 C33 C34 -57.3(4) . . . . ?
C37 N6 C34 C33 179.8(3) . . . . ?
C37 N6 C35 C36 179.1(3) . . . . ?
