#------------------------------------------------------------------------------
#$Date: 2016-02-17 16:13:21 +0200 (Wed, 17 Feb 2016) $
#$Revision: 176652 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/14/2241447.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2241447
loop_
_publ_author_name
'An, Zhe'
'Gao, Jing'
'Harrison, William T. A.'
_publ_section_title
;
 Crystal structures of [Mn(bdc)(Hspar)₂(H₂O)~0.25~]·2H₂O
 containing MnO₆₊₁ capped trigonal prisms and
 [Cu(Hspar)₂](bdc)·2H₂O containing CuO₄ squares (Hspar =
 sparfloxacin and bdc = benzene-1,4-dicarboxylate)
;
_journal_coeditor_code           SJ5492
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              96
_journal_page_last               101
_journal_paper_doi               10.1107/S205698901502424X
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          '[Cu (C19 H22 F2 N4 O3)2] (C8 H4 O4), 2H2 O'
_chemical_formula_moiety         'C38 H44 Cu F4 N8 O6 +, C8 H4 O4 -, 2(H2 O)'
_chemical_formula_sum            'C46 H52 Cu F4 N8 O12'
_chemical_formula_weight         1048.50
_chemical_name_systematic
;Bis(sparfloxacin-κ²O,O')copper(II) benzene-1,4-dicarboxylate
dihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.7640(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.6039(2)
_cell_length_b                   7.80190(10)
_cell_length_c                   22.0870(3)
_cell_measurement_reflns_used    3693
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.52
_cell_measurement_theta_min      2.72
_cell_volume                     2276.91(5)
_computing_cell_refinement
;
SAINT (Bruker, 2004)
;
_computing_data_collection
;
SMART (Bruker, 2004)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20662
_diffrn_reflns_theta_full        27.40
_diffrn_reflns_theta_max         27.40
_diffrn_reflns_theta_min         2.72
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_T_max  0.9295
_exptl_absorpt_correction_T_min  0.8945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1090
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.568
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0611P)²+1.3659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1423
_reflns_number_gt                3641
_reflns_number_total             5168
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5492sup1.cif
_cod_data_source_block           II
_cod_depositor_comments
;Adding full bibliography for 2241446--2241447.cif.

 Adding full bibliography for 2241446--2241447.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2241447
_cod_database_fobs_code          2241447
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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.5000 0.0000 0.5000 0.03589(15) Uani d S 1 2 . .
C C1 0.4364(3) 0.1538(4) 0.60336(15) 0.0509(8) Uani d . 1 1 . .
C C2 0.3912(2) 0.3007(4) 0.56214(13) 0.0406(7) Uani d . 1 1 . .
C C3 0.4015(2) 0.3268(3) 0.50090(13) 0.0344(6) Uani d . 1 1 . .
C C4 0.3610(2) 0.4832(3) 0.46921(13) 0.0344(6) Uani d . 1 1 . .
C C5 0.3720(2) 0.5207(3) 0.40786(13) 0.0378(6) Uani d . 1 1 . .
C C6 0.3248(2) 0.6682(4) 0.37975(14) 0.0436(7) Uani d . 1 1 . .
C C7 0.2699(2) 0.7814(4) 0.40656(14) 0.0439(7) Uani d . 1 1 . .
C C8 0.2666(3) 0.7474(4) 0.46785(14) 0.0521(8) Uani d . 1 1 . .
C C9 0.3090(2) 0.6018(4) 0.49971(13) 0.0428(7) Uani d . 1 1 A .
C C10 0.3449(3) 0.4244(4) 0.58938(15) 0.0527(8) Uani d . 1 1 A .
H H10 0.3410 0.4065 0.6304 0.063 Uiso calc R 1 1 . .
C C11A 0.3034(7) 0.7255(11) 0.5989(4) 0.034(2) Uiso d P 0.330(8) 1 A 1
H H11A 0.3558 0.8116 0.5986 0.041 Uiso calc PR 0.330(8) 1 A 1
C C11B 0.2443(4) 0.6775(6) 0.5977(2) 0.0414(13) Uiso d P 0.670(8) 1 A 2
H H11B 0.1714 0.6862 0.5796 0.050 Uiso calc PR 0.670(8) 1 A 2
C C12 0.2750(4) 0.6913(5) 0.6618(2) 0.0779(13) Uani d . 1 1 . .
H H12A 0.3388 0.6498 0.6871 0.093 Uiso d R 1 1 A .
H H12B 0.2167 0.6809 0.6797 0.093 Uiso d R 1 1 . .
C C13A 0.1996(8) 0.7884(13) 0.5963(5) 0.050(3) Uiso d P 0.330(8) 1 A 1
H H13A 0.1294 0.7534 0.5824 0.060 Uiso d PR 0.330(8) 1 A 1
H H13B 0.2141 0.9063 0.5875 0.060 Uiso d PR 0.330(8) 1 A 1
C C13B 0.2951(4) 0.8341(7) 0.6235(2) 0.0548(16) Uiso d P 0.670(8) 1 A 2
H H13C 0.2498 0.9319 0.6178 0.066 Uiso d PR 0.670(8) 1 A 2
H H13D 0.3652 0.8611 0.6250 0.066 Uiso d PR 0.670(8) 1 A 2
C C14 0.2694(2) 1.0478(4) 0.34509(16) 0.0477(8) Uani d . 1 1 . .
H H14A 0.3360 1.0072 0.3431 0.057 Uiso calc R 1 1 . .
H H14B 0.2780 1.1508 0.3704 0.057 Uiso calc R 1 1 . .
C C15 0.2084(2) 1.0892(4) 0.28020(14) 0.0399(6) Uani d . 1 1 . .
H H15 0.2049 0.9859 0.2545 0.048 Uiso calc R 1 1 . .
C C16 0.0536(2) 1.0046(4) 0.31469(13) 0.0388(6) Uani d . 1 1 . .
H H16 0.0481 0.8983 0.2905 0.047 Uiso calc R 1 1 . .
C C17 0.1190(2) 0.9702(4) 0.37892(14) 0.0453(7) Uani d . 1 1 . .
H H17A 0.1240 1.0729 0.4042 0.054 Uiso calc R 1 1 . .
H H17B 0.0890 0.8802 0.3990 0.054 Uiso calc R 1 1 . .
C C18 0.2539(3) 1.2321(5) 0.24928(16) 0.0561(9) Uani d . 1 1 . .
H H18A 0.2150 1.2467 0.2072 0.084 Uiso calc R 1 1 . .
H H18B 0.3224 1.2035 0.2490 0.084 Uiso calc R 1 1 . .
H H18C 0.2532 1.3367 0.2720 0.084 Uiso calc R 1 1 . .
C C19 -0.0522(2) 1.0637(5) 0.31529(17) 0.0557(8) Uani d . 1 1 . .
H H19A -0.0484 1.1682 0.3387 0.084 Uiso calc R 1 1 . .
H H19B -0.0852 0.9771 0.3342 0.084 Uiso calc R 1 1 . .
H H19C -0.0902 1.0833 0.2733 0.084 Uiso calc R 1 1 . .
N N1 0.4226(2) 0.4198(3) 0.37568(12) 0.0482(6) Uani d . 1 1 . .
H H1A 0.4252 0.4473 0.3384 0.058 Uiso calc R 1 1 . .
H H1B 0.4521 0.3281 0.3925 0.058 Uiso calc R 1 1 . .
N N2 0.3048(2) 0.5684(3) 0.56173(11) 0.0517(7) Uani d . 1 1 . .
N N3 0.2191(2) 0.9183(3) 0.37340(13) 0.0519(7) Uani d . 1 1 . .
N N4 0.10343(17) 1.1367(3) 0.28308(10) 0.0355(5) Uani d . 1 1 . .
H H4A 0.0659 1.1525 0.2440 0.043 Uiso calc R 1 1 . .
H H4B 0.1053 1.2368 0.3036 0.043 Uiso calc R 1 1 . .
O O1 0.4311(3) 0.1573(4) 0.65800(12) 0.0909(11) Uani d . 1 1 . .
O O2 0.47895(16) 0.0304(2) 0.58081(9) 0.0447(5) Uani d . 1 1 . .
O O3 0.44457(16) 0.2185(2) 0.47204(9) 0.0438(5) Uani d . 1 1 . .
F F1 0.32798(15) 0.6955(2) 0.31954(9) 0.0609(5) Uani d . 1 1 . .
F F2A 0.2432(5) 0.8883(6) 0.49417(18) 0.0451(16) Uiso d P 0.456(11) 1 . .
F F2B 0.1995(4) 0.8500(5) 0.49550(15) 0.0436(13) Uiso d P 0.544(11) 1 . .
C C20 -0.0172(2) 0.0098(3) 0.06024(12) 0.0350(6) Uani d . 1 1 . .
C C21 0.0523(2) 0.1177(4) 0.04203(13) 0.0416(7) Uani d . 1 1 . .
H H21 0.0877 0.1977 0.0701 0.050 Uiso calc R 1 1 . .
C C22 0.0694(2) 0.1077(4) -0.01728(13) 0.0420(7) Uani d . 1 1 . .
H H22 0.1163 0.1805 -0.0284 0.050 Uiso calc R 1 1 . .
C C23 -0.0320(2) 0.0165(4) 0.12619(13) 0.0415(7) Uani d . 1 1 . .
O O4 -0.0936(2) -0.0847(3) 0.14030(11) 0.0607(6) Uani d . 1 1 . .
O O5 0.02068(19) 0.1251(3) 0.16135(10) 0.0598(6) Uani d . 1 1 . .
O O6 0.4982(2) 0.0203(4) 0.23468(11) 0.0704(7) Uani d . 1 1 . .
H H1W 0.5212 0.0005 0.2729 0.084 Uiso d R 1 1 . .
H H2W 0.5047 0.1270 0.2369 0.084 Uiso d R 1 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 Cu1 O2 . 3_656 180.0 ?
O2 Cu1 O3 . 3_656 86.76(8) ?
O2 Cu1 O3 3_656 3_656 93.24(8) ?
O2 Cu1 O3 . . 93.24(8) y
O2 Cu1 O3 3_656 . 86.76(8) ?
O3 Cu1 O3 3_656 . 180.0 ?
O1 C1 O2 . . 122.4(3) ?
O1 C1 C2 . . 117.9(3) ?
O2 C1 C2 . . 119.6(3) ?
C10 C2 C3 . . 118.8(3) ?
C10 C2 C1 . . 115.9(3) ?
C3 C2 C1 . . 125.0(3) ?
O3 C3 C2 . . 123.0(2) ?
O3 C3 C4 . . 118.8(2) ?
C2 C3 C4 . . 118.3(2) ?
C9 C4 C5 . . 119.4(2) ?
C9 C4 C3 . . 119.5(2) ?
C5 C4 C3 . . 121.2(2) ?
N1 C5 C6 . . 119.0(3) ?
N1 C5 C4 . . 124.1(2) ?
C6 C5 C4 . . 116.9(3) ?
F1 C6 C7 . . 117.9(2) ?
F1 C6 C5 . . 116.6(3) ?
C7 C6 C5 . . 125.3(3) ?
C6 C7 N3 . . 121.4(3) ?
C6 C7 C8 . . 116.3(3) ?
N3 C7 C8 . . 122.3(3) ?
F2A C8 C9 . . 125.0(3) ?
F2A C8 C7 . . 109.7(3) ?
C9 C8 C7 . . 123.0(3) ?
F2A C8 F2B . . 27.5(2) ?
C9 C8 F2B . . 117.7(3) ?
C7 C8 F2B . . 118.2(3) ?
C8 C9 N2 . . 122.5(3) ?
C8 C9 C4 . . 119.0(3) ?
N2 C9 C4 . . 118.6(2) ?
N2 C10 C2 . . 125.1(3) ?
N2 C10 H10 . . 117.5 ?
C2 C10 H10 . . 117.5 ?
N2 C11A C13A . . 113.0(7) ?
N2 C11A C12 . . 113.2(6) ?
C13A C11A C12 . . 69.7(6) ?
N2 C11A H11A . . 117.4 ?
C13A C11A H11A . . 117.4 ?
C12 C11A H11A . . 117.4 ?
C13A C11A H13D . . 104.0 ?
C12 C11B C13B . . 62.2(3) ?
C12 C11B N2 . . 120.4(4) ?
C13B C11B N2 . . 114.0(4) ?
C12 C11B H11B . . 116.3 ?
C13B C11B H11B . . 116.3 ?
N2 C11B H11B . . 116.3 ?
C11B C12 C13B . . 61.3(3) ?
C13B C12 H12A . . 108.8 ?
C11A C12 H12A . . 101.2 ?
C11B C12 H12B . . 109.5 ?
H12A C12 H12B . . 116.3 ?
C11A C13A C12 . . 57.0(5) ?
C11A C13A H13A . . 140.9 ?
C12 C13A H13A . . 118.8 ?
C12 C13A H13B . . 118.2 ?
H13A C13A H13B . . 115.8 ?
C11B C13B C12 . . 56.5(3) ?
C12 C13B H13B . . 115.4 ?
C11B C13B H13C . . 112.6 ?
C12 C13B H13C . . 118.2 ?
C12 C13B H13D . . 117.6 ?
H13C C13B H13D . . 115.0 ?
N3 C14 C15 . . 110.5(3) ?
N3 C14 H14A . . 109.5 ?
C15 C14 H14A . . 109.5 ?
N3 C14 H14B . . 109.5 ?
C15 C14 H14B . . 109.5 ?
H14A C14 H14B . . 108.1 ?
N4 C15 C14 . . 109.1(2) ?
N4 C15 C18 . . 109.5(2) ?
C14 C15 C18 . . 113.2(3) ?
N4 C15 H15 . . 108.3 ?
C14 C15 H15 . . 108.3 ?
C18 C15 H15 . . 108.3 ?
N4 C16 C17 . . 109.3(2) ?
N4 C16 C19 . . 109.4(2) ?
C17 C16 C19 . . 113.3(3) ?
N4 C16 H16 . . 108.3 ?
C17 C16 H16 . . 108.3 ?
C19 C16 H16 . . 108.3 ?
N3 C17 C16 . . 109.0(3) ?
N3 C17 H17A . . 109.9 ?
C16 C17 H17A . . 109.9 ?
N3 C17 H17B . . 109.9 ?
C16 C17 H17B . . 109.9 ?
H17A C17 H17B . . 108.3 ?
C15 C18 H18A . . 109.5 ?
C15 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C15 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C16 C19 H19A . . 109.5 ?
C16 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C16 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C5 N1 H1A . . 120.0 ?
C5 N1 H1B . . 120.0 ?
H1A N1 H1B . . 120.0 ?
C10 N2 C9 . . 119.7(3) ?
C10 N2 C11A . . 120.2(4) ?
C9 N2 C11A . . 113.3(4) ?
C10 N2 C11B . . 116.3(3) ?
C9 N2 C11B . . 123.6(3) ?
C11A N2 C11B . . 34.0(3) ?
C7 N3 C14 . . 122.8(3) ?
C7 N3 C17 . . 122.1(3) ?
C14 N3 C17 . . 113.0(2) ?
C15 N4 C16 . . 113.2(2) ?
C15 N4 H4A . . 108.9 ?
C16 N4 H4A . . 108.9 ?
C15 N4 H4B . . 108.9 ?
C16 N4 H4B . . 108.9 ?
H4A N4 H4B . . 107.8 ?
C1 O2 Cu1 . . 130.16(19) ?
C3 O3 Cu1 . . 128.39(18) ?
F2B F2A C8 . . 87.6(6) ?
F2A F2B C8 . . 64.9(5) ?
C22 C20 C21 3 . 118.3(3) ?
C22 C20 C23 3 . 121.1(3) ?
C21 C20 C23 . . 120.6(3) ?
C22 C21 C20 . . 121.1(3) ?
C22 C21 H21 . . 119.5 ?
C20 C21 H21 . . 119.5 ?
C21 C22 C20 . 3 120.7(3) ?
C21 C22 H22 . . 119.7 ?
C20 C22 H22 3 . 119.7 ?
O4 C23 O5 . . 126.4(3) ?
O4 C23 C20 . . 118.0(3) ?
O5 C23 C20 . . 115.6(3) ?
H1W O6 H2W . . 96.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O2 . 1.889(2) y
Cu1 O2 3_656 1.889(2) ?
Cu1 O3 3_656 1.9064(18) ?
Cu1 O3 . 1.9064(18) y
C1 O1 . 1.226(4) y
C1 O2 . 1.283(4) y
C1 C2 . 1.501(4) ?
C2 C10 . 1.368(4) ?
C2 C3 . 1.407(4) ?
C3 O3 . 1.281(3) ?
C3 C4 . 1.449(4) ?
C4 C9 . 1.428(4) ?
C4 C5 . 1.428(4) ?
C5 N1 . 1.353(4) ?
C5 C6 . 1.390(4) ?
C6 F1 . 1.358(3) ?
C6 C7 . 1.377(4) ?
C7 N3 . 1.384(4) ?
C7 C8 . 1.391(4) ?
C8 F2A . 1.317(5) ?
C8 C9 . 1.387(4) ?
C8 F2B . 1.453(5) ?
C9 N2 . 1.409(4) ?
C10 N2 . 1.332(4) ?
C10 H10 . 0.9300 ?
C11A N2 . 1.478(9) ?
C11A C13A . 1.483(14) ?
C11A C12 . 1.551(9) ?
C11A H11A . 0.9800 ?
C11B C12 . 1.380(6) ?
C11B C13B . 1.451(7) ?
C11B N2 . 1.532(5) ?
C11B H11B . 0.9800 ?
C12 C13B . 1.463(6) ?
C12 C13A . 1.736(11) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13A H13A . 0.9700 ?
C13A H13B . 0.9700 ?
C13B H13C . 0.9700 ?
C13B H13D . 0.9700 ?
C14 N3 . 1.444(4) ?
C14 C15 . 1.510(4) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 N4 . 1.492(3) ?
C15 C18 . 1.515(4) ?
C15 H15 . 0.9800 ?
C16 N4 . 1.494(4) ?
C16 C17 . 1.508(4) ?
C16 C19 . 1.515(4) ?
C16 H16 . 0.9800 ?
C17 N3 . 1.454(4) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
N1 H1A . 0.8600 ?
N1 H1B . 0.8600 ?
N4 H4A . 0.9000 ?
N4 H4B . 0.9000 ?
C20 C22 3 1.387(4) ?
C20 C21 . 1.395(4) ?
C20 C23 . 1.518(4) ?
C21 C22 . 1.386(4) ?
C21 H21 . 0.9300 ?
C22 C20 3 1.387(4) ?
C22 H22 . 0.9300 ?
C23 O4 . 1.244(4) y
C23 O5 . 1.253(4) y
O6 H1W . 0.8412 ?
O6 H2W . 0.8376 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A F1 . 0.86 2.33 2.657(3) 103
N1 H1A O6 2_655 0.86 2.19 2.995(4) 155
N1 H1B O3 . 0.86 1.98 2.604(3) 129
N4 H4A O5 1_565 0.90 1.80 2.658(3) 160
N4 H4B O4 2_565 0.90 1.90 2.777(3) 166
O6 H1W O1 3_656 0.84 1.95 2.716(3) 151
O6 H2W O1 4_565 0.84 2.46 3.048(4) 128
C12 H12A O6 4_566 0.97 2.55 3.494(5) 166
C13B H13D O1 1_565 0.97 2.52 3.113(6) 119
C13B H13D O2 1_565 0.97 2.41 3.258(6) 146
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
O1 C1 C2 C10 . . -2.0(5)
O2 C1 C2 C10 . . 178.2(3)
O1 C1 C2 C3 . . 171.9(3)
O2 C1 C2 C3 . . -7.9(5)
C10 C2 C3 O3 . . 179.4(3)
C1 C2 C3 O3 . . 5.7(5)
C10 C2 C3 C4 . . -0.8(4)
C1 C2 C3 C4 . . -174.5(3)
O3 C3 C4 C9 . . 177.4(3)
C2 C3 C4 C9 . . -2.5(4)
O3 C3 C4 C5 . . -2.4(4)
C2 C3 C4 C5 . . 177.8(3)
C9 C4 C5 N1 . . 177.9(3)
C3 C4 C5 N1 . . -2.4(4)
C9 C4 C5 C6 . . -3.9(4)
C3 C4 C5 C6 . . 175.8(3)
N1 C5 C6 F1 . . 3.8(4)
C4 C5 C6 F1 . . -174.5(2)
N1 C5 C6 C7 . . 179.2(3)
C4 C5 C6 C7 . . 0.9(4)
F1 C6 C7 N3 . . 0.3(4)
C5 C6 C7 N3 . . -175.0(3)
F1 C6 C7 C8 . . 178.7(3)
C5 C6 C7 C8 . . 3.4(5)
C6 C7 C8 F2A . . 158.9(4)
N3 C7 C8 F2A . . -22.7(5)
C6 C7 C8 C9 . . -4.7(5)
N3 C7 C8 C9 . . 173.6(3)
C6 C7 C8 F2B . . -172.4(4)
N3 C7 C8 F2B . . 6.0(5)
F2A C8 C9 N2 . . 19.1(7)
C7 C8 C9 N2 . . -179.8(3)
F2B C8 C9 N2 . . -12.1(5)
F2A C8 C9 C4 . . -159.2(5)
C7 C8 C9 C4 . . 1.8(5)
F2B C8 C9 C4 . . 169.5(3)
C5 C4 C9 C8 . . 2.7(4)
C3 C4 C9 C8 . . -177.1(3)
C5 C4 C9 N2 . . -175.8(3)
C3 C4 C9 N2 . . 4.5(4)
C3 C2 C10 N2 . . 2.2(5)
C1 C2 C10 N2 . . 176.5(3)
N2 C11B C12 C13B . . 102.9(5)
C13B C11B C12 C11A . . -41.2(6)
N2 C11B C12 C11A . . 61.7(7)
C13B C11B C12 C13A . . 58.5(7)
N2 C11B C12 C13A . . 161.5(9)
N2 C11A C12 C11B . . -58.9(6)
C13A C11A C12 C11B . . 48.2(6)
N2 C11A C12 C13B . . -174.2(10)
C13A C11A C12 C13B . . -67.1(7)
N2 C11A C12 C13A . . -107.1(8)
N2 C11A C13A C12 . . 107.4(7)
C11B C12 C13A C11A . . -44.0(6)
C13B C12 C13A C11A . . 51.5(5)
N2 C11B C13B C12 . . -113.1(4)
C11A C12 C13B C11B . . 35.6(6)
C13A C12 C13B C11B . . -43.5(5)
N3 C14 C15 N4 . . 54.3(3)
N3 C14 C15 C18 . . 176.5(3)
N4 C16 C17 N3 . . -56.5(3)
C19 C16 C17 N3 . . -178.7(3)
C2 C10 N2 C9 . . -0.2(6)
C2 C10 N2 C11A . . -149.3(5)
C2 C10 N2 C11B . . 172.1(4)
C8 C9 N2 C10 . . 178.4(3)
C4 C9 N2 C10 . . -3.2(5)
C8 C9 N2 C11A . . -30.4(6)
C4 C9 N2 C11A . . 148.0(4)
C8 C9 N2 C11B . . 6.7(5)
C4 C9 N2 C11B . . -174.9(3)
C13A C11A N2 C10 . . -118.7(6)
C12 C11A N2 C10 . . -41.9(8)
C13A C11A N2 C9 . . 90.3(7)
C12 C11A N2 C9 . . 167.2(4)
C13A C11A N2 C11B . . -25.7(6)
C12 C11A N2 C11B . . 51.2(6)
C12 C11B N2 C10 . . 36.8(6)
C13B C11B N2 C10 . . 107.5(4)
C12 C11B N2 C9 . . -151.2(4)
C13B C11B N2 C9 . . -80.5(5)
C12 C11B N2 C11A . . -69.0(7)
C13B C11B N2 C11A . . 1.7(6)
C6 C7 N3 C14 . . -58.0(4)
C8 C7 N3 C14 . . 123.7(4)
C6 C7 N3 C17 . . 139.8(3)
C8 C7 N3 C17 . . -38.5(4)
C15 C14 N3 C7 . . 136.4(3)
C15 C14 N3 C17 . . -60.0(4)
C16 C17 N3 C7 . . -135.5(3)
C16 C17 N3 C14 . . 60.8(3)
C14 C15 N4 C16 . . -53.9(3)
C18 C15 N4 C16 . . -178.3(2)
C17 C16 N4 C15 . . 55.5(3)
C19 C16 N4 C15 . . -179.9(2)
O1 C1 O2 Cu1 . . -177.8(3)
C2 C1 O2 Cu1 . . 2.0(5)
O3 Cu1 O2 C1 3_656 . -176.4(3)
O3 Cu1 O2 C1 . . 3.6(3)
C2 C3 O3 Cu1 . . 2.4(4)
C4 C3 O3 Cu1 . . -177.49(18)
O2 Cu1 O3 C3 . . -6.0(2)
O2 Cu1 O3 C3 3_656 . 174.0(2)
C9 C8 F2A F2B . . -83.2(6)
C7 C8 F2A F2B . . 113.6(5)
C9 C8 F2B F2A . . 113.3(6)
C7 C8 F2B F2A . . -78.4(6)
C22 C20 C21 C22 3 . -0.3(5)
C23 C20 C21 C22 . . 177.2(3)
C20 C21 C22 C20 . 3 0.3(5)
C22 C20 C23 O4 3 . -1.2(4)
C21 C20 C23 O4 . . -178.8(3)
C22 C20 C23 O5 3 . 178.5(3)
C21 C20 C23 O5 . . 1.0(4)
