#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/09/2230919.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_2230919
loop_
_publ_author_name
'Necefoğlu, Hacali'
'Özbek, Füreya Elif'
'Öztürk, Vijdan'
'Tercan, Barış'
'Hökelek, Tuncer'
_publ_section_title
;
 Bis(4-fluorobenzoato)-κ²O,O';κO-(4-fluorobenzoic
 acid-κO)bis(nicotinamide-κN¹)copper(II)
;
_journal_coeditor_code           XU5224
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m887
_journal_page_last               m888
_journal_paper_doi               10.1107/S1600536811020897
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac
'[Cu (C7 H4 F O2)2 (C7 H5 F O2) (C6 H6 N2 O)2]'
_chemical_formula_moiety         'C33 H25 Cu F3 N4 O8'
_chemical_formula_sum            'C33 H25 Cu F3 N4 O8'
_chemical_formula_weight         726.12
_chemical_name_systematic
;
Bis(4-fluorobenzoato)-κ²O,O';κO-(4-fluorobenzoic
acid-κO)bis(nicotinamide-κN¹)copper(II)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                110.824(4)
_cell_angle_beta                 101.333(3)
_cell_angle_gamma                95.761(2)
_cell_formula_units_Z            2
_cell_length_a                   10.3370(2)
_cell_length_b                   11.6707(3)
_cell_length_c                   14.1121(4)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.52
_cell_volume                     1533.09(8)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII Kappa CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27657
_diffrn_reflns_theta_full        28.47
_diffrn_reflns_theta_max         28.47
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  0.8268
_exptl_absorpt_correction_T_min  0.7451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             742
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.530
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         7686
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0359
_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)+(0.0247P)²+1.9077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0869
_reflns_number_gt                6584
_reflns_number_total             7686
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5224.cif
_cod_data_source_block           I
_cod_database_code               2230919
_cod_database_fobs_code          2230919
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.13629(2) 0.00940(2) 0.301857(18) 0.01112(7) Uani d . 1 1 . .
O O1 0.21519(13) -0.08538(12) 0.17898(10) 0.0128(3) Uani d . 1 1 . .
O O2 0.37085(14) 0.06815(12) 0.30046(11) 0.0147(3) Uani d . 1 1 . .
O O3 -0.06751(14) -0.11248(13) 0.23335(11) 0.0162(3) Uani d . 1 1 . .
O O4 -0.19206(16) -0.02059(14) 0.34144(13) 0.0243(3) Uani d D 1 1 . .
H H41 -0.136(3) 0.048(2) 0.367(3) 0.056 Uiso d D 1 1 . .
O O5 0.15186(15) 0.14357(13) 0.43863(11) 0.0181(3) Uani d . 1 1 . .
O O6 -0.05429(16) 0.19004(14) 0.42197(13) 0.0258(4) Uani d . 1 1 . .
O O7 0.36816(15) -0.47531(13) 0.40855(12) 0.0205(3) Uani d . 1 1 . .
O O8 0.08320(16) 0.47994(13) 0.11418(12) 0.0240(3) Uani d . 1 1 . .
N N1 0.19980(16) -0.10554(14) 0.37023(12) 0.0121(3) Uani d . 1 1 . .
N N2 0.49317(18) -0.32379(16) 0.55914(14) 0.0166(4) Uani d . 1 1 . .
H H2A 0.532(3) -0.377(3) 0.572(2) 0.036(8) Uiso d . 1 1 . .
H H2B 0.517(3) -0.243(3) 0.602(2) 0.037(8) Uiso d . 1 1 . .
N N3 0.09164(16) 0.12271(14) 0.22622(13) 0.0121(3) Uani d . 1 1 . .
N N4 -0.05759(19) 0.33049(17) -0.02899(14) 0.0180(4) Uani d . 1 1 . .
H H4A -0.094(3) 0.260(3) -0.061(2) 0.019(6) Uiso d . 1 1 . .
H H4B -0.070(2) 0.380(2) -0.056(2) 0.022(6) Uiso d . 1 1 . .
F F1 0.71007(14) -0.12837(14) -0.02727(11) 0.0314(3) Uani d . 1 1 . .
F F2 -0.56952(14) -0.53850(12) 0.11468(12) 0.0331(3) Uani d . 1 1 . .
F F3 0.28179(16) 0.69704(12) 0.76409(12) 0.0398(4) Uani d . 1 1 . .
C C1 0.33457(19) -0.02071(17) 0.21304(15) 0.0123(4) Uani d . 1 1 . .
C C2 0.4321(2) -0.05193(17) 0.14653(15) 0.0137(4) Uani d . 1 1 . .
C C3 0.4058(2) -0.16158(18) 0.05765(16) 0.0168(4) Uani d . 1 1 . .
H H3 0.3252 -0.2172 0.0377 0.020 Uiso calc R 1 1 . .
C C4 0.4999(2) -0.1880(2) -0.00125(17) 0.0218(4) Uani d . 1 1 . .
H H4 0.4835 -0.2610 -0.0607 0.026 Uiso calc R 1 1 . .
C C5 0.6176(2) -0.1036(2) 0.03036(18) 0.0214(4) Uani d . 1 1 . .
C C6 0.6464(2) 0.0058(2) 0.11703(18) 0.0219(4) Uani d . 1 1 . .
H H6 0.7266 0.0616 0.1357 0.026 Uiso calc R 1 1 . .
C C7 0.5526(2) 0.03054(18) 0.17561(17) 0.0175(4) Uani d . 1 1 . .
H H7 0.5705 0.1034 0.2353 0.021 Uiso calc R 1 1 . .
C C8 -0.1680(2) -0.11385(18) 0.26792(15) 0.0155(4) Uani d . 1 1 . .
C C9 -0.2758(2) -0.22678(18) 0.22622(16) 0.0160(4) Uani d . 1 1 . .
C C10 -0.2572(2) -0.33826(19) 0.15506(17) 0.0202(4) Uani d . 1 1 . .
H H10 -0.1778 -0.3417 0.1333 0.024 Uiso calc R 1 1 . .
C C11 -0.3561(2) -0.4443(2) 0.11633(18) 0.0243(5) Uani d . 1 1 . .
H H11 -0.3441 -0.5194 0.0693 0.029 Uiso calc R 1 1 . .
C C12 -0.4729(2) -0.4351(2) 0.14966(18) 0.0222(4) Uani d . 1 1 . .
C C13 -0.4959(2) -0.3259(2) 0.21821(17) 0.0210(4) Uani d . 1 1 . .
H H13 -0.5767 -0.3224 0.2377 0.025 Uiso calc R 1 1 . .
C C14 -0.3952(2) -0.22134(19) 0.25738(16) 0.0178(4) Uani d . 1 1 . .
H H14 -0.4077 -0.1468 0.3050 0.021 Uiso calc R 1 1 . .
C C15 0.0698(2) 0.21594(18) 0.46296(16) 0.0168(4) Uani d . 1 1 . .
C C16 0.1269(2) 0.34387(18) 0.54508(16) 0.0161(4) Uani d . 1 1 . .
C C17 0.0416(2) 0.42600(19) 0.57831(17) 0.0202(4) Uani d . 1 1 . .
H H17 -0.0507 0.4006 0.5507 0.024 Uiso calc R 1 1 . .
C C18 0.0935(2) 0.5457(2) 0.65259(18) 0.0255(5) Uani d . 1 1 . .
H H18 0.0372 0.6013 0.6757 0.031 Uiso calc R 1 1 . .
C C19 0.2303(2) 0.57979(19) 0.69091(17) 0.0249(5) Uani d . 1 1 . .
C C20 0.3180(2) 0.5021(2) 0.65898(17) 0.0226(4) Uani d . 1 1 . .
H H20 0.4103 0.5289 0.6858 0.027 Uiso calc R 1 1 . .
C C21 0.2647(2) 0.38235(19) 0.58543(16) 0.0187(4) Uani d . 1 1 . .
H H21 0.3218 0.3274 0.5630 0.022 Uiso calc R 1 1 . .
C C22 0.2985(2) -0.06282(17) 0.45817(15) 0.0139(4) Uani d . 1 1 . .
H H22 0.3234 0.0229 0.4955 0.017 Uiso calc R 1 1 . .
C C23 0.3654(2) -0.14142(17) 0.49619(15) 0.0147(4) Uani d . 1 1 . .
H H23 0.4332 -0.1088 0.5579 0.018 Uiso calc R 1 1 . .
C C24 0.32900(19) -0.26950(17) 0.44009(15) 0.0123(4) Uani d . 1 1 . .
C C25 0.2243(2) -0.31342(17) 0.35045(15) 0.0147(4) Uani d . 1 1 . .
H H25 0.1963 -0.3987 0.3123 0.018 Uiso calc R 1 1 . .
C C26 0.1621(2) -0.22944(17) 0.31836(15) 0.0144(4) Uani d . 1 1 . .
H H26 0.0913 -0.2599 0.2586 0.017 Uiso calc R 1 1 . .
C C27 0.3992(2) -0.36452(17) 0.46928(15) 0.0139(4) Uani d . 1 1 . .
C C28 -0.00464(19) 0.08500(17) 0.13710(15) 0.0127(4) Uani d . 1 1 . .
H H28 -0.0564 0.0055 0.1121 0.015 Uiso calc R 1 1 . .
C C29 -0.03050(19) 0.15950(17) 0.08046(15) 0.0133(4) Uani d . 1 1 . .
H H29 -0.0996 0.1312 0.0197 0.016 Uiso calc R 1 1 . .
C C30 0.04892(19) 0.27753(17) 0.11612(15) 0.0126(4) Uani d . 1 1 . .
C C31 0.1513(2) 0.31490(17) 0.20657(16) 0.0147(4) Uani d . 1 1 . .
H H31 0.2075 0.3922 0.2313 0.018 Uiso calc R 1 1 . .
C C32 0.1690(2) 0.23614(17) 0.25979(15) 0.0141(4) Uani d . 1 1 . .
H H32 0.2369 0.2626 0.3211 0.017 Uiso calc R 1 1 . .
C C33 0.0257(2) 0.37055(17) 0.06562(16) 0.0154(4) Uani d . 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 0.0030 0.0020 '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 0.3200 1.2650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O3 . . 95.03(5) ?
O1 Cu1 O2 . . 57.75(5) ?
O5 Cu1 O1 . . 151.82(6) ?
O5 Cu1 O3 . . 113.15(6) ?
O5 Cu1 N1 . . 91.60(6) ?
O5 Cu1 N3 . . 91.70(6) ?
N1 Cu1 O1 . . 87.92(6) ?
N1 Cu1 O3 . . 90.60(6) ?
N1 Cu1 N3 . . 173.23(7) ?
N3 Cu1 O1 . . 86.39(6) ?
N3 Cu1 O3 . . 93.54(6) ?
C1 O1 Cu1 . . 98.92(11) ?
C8 O3 Cu1 . . 131.63(13) ?
C8 O4 H41 . . 118(2) ?
C15 O5 Cu1 . . 127.21(13) ?
C22 N1 Cu1 . . 120.76(13) ?
C22 N1 C26 . . 118.27(16) ?
C26 N1 Cu1 . . 119.79(13) ?
C27 N2 H2A . . 116(2) ?
C27 N2 H2B . . 123.0(18) ?
H2A N2 H2B . . 121(3) ?
C28 N3 Cu1 . . 122.20(12) ?
C28 N3 C32 . . 118.18(16) ?
C32 N3 Cu1 . . 119.29(13) ?
C33 N4 H4A . . 123.1(18) ?
C33 N4 H4B . . 118.4(18) ?
H4A N4 H4B . . 118(3) ?
O1 C1 C2 . . 119.12(17) ?
O2 C1 O1 . . 121.48(18) ?
O2 C1 C2 . . 119.40(17) ?
C3 C2 C1 . . 121.88(18) ?
C7 C2 C1 . . 118.57(18) ?
C7 C2 C3 . . 119.54(19) ?
C2 C3 H3 . . 119.9 ?
C4 C3 C2 . . 120.1(2) ?
C4 C3 H3 . . 119.9 ?
C3 C4 H4 . . 120.8 ?
C5 C4 C3 . . 118.3(2) ?
C5 C4 H4 . . 120.8 ?
F1 C5 C4 . . 118.8(2) ?
F1 C5 C6 . . 118.1(2) ?
C4 C5 C6 . . 123.2(2) ?
C5 C6 C7 . . 118.0(2) ?
C5 C6 H6 . . 121.0 ?
C7 C6 H6 . . 121.0 ?
C2 C7 H7 . . 119.6 ?
C6 C7 C2 . . 120.9(2) ?
C6 C7 H7 . . 119.6 ?
O3 C8 O4 . . 124.89(19) ?
O3 C8 C9 . . 121.66(18) ?
O4 C8 C9 . . 113.45(18) ?
C10 C9 C8 . . 119.82(19) ?
C14 C9 C8 . . 120.45(18) ?
C14 C9 C10 . . 119.73(19) ?
C9 C10 H10 . . 119.8 ?
C11 C10 C9 . . 120.4(2) ?
C11 C10 H10 . . 119.8 ?
C10 C11 H11 . . 121.0 ?
C12 C11 C10 . . 118.0(2) ?
C12 C11 H11 . . 121.0 ?
F2 C12 C11 . . 118.9(2) ?
F2 C12 C13 . . 118.0(2) ?
C13 C12 C11 . . 123.1(2) ?
C12 C13 C14 . . 118.1(2) ?
C12 C13 H13 . . 120.9 ?
C14 C13 H13 . . 120.9 ?
C9 C14 H14 . . 119.7 ?
C13 C14 C9 . . 120.56(19) ?
C13 C14 H14 . . 119.7 ?
O5 C15 C16 . . 116.89(19) ?
O6 C15 O5 . . 125.26(19) ?
O6 C15 C16 . . 117.83(18) ?
C17 C16 C15 . . 119.70(19) ?
C21 C16 C15 . . 120.46(18) ?
C21 C16 C17 . . 119.79(19) ?
C16 C17 H17 . . 119.9 ?
C18 C17 C16 . . 120.3(2) ?
C18 C17 H17 . . 119.9 ?
C17 C18 H18 . . 121.0 ?
C19 C18 C17 . . 118.1(2) ?
C19 C18 H18 . . 121.0 ?
F3 C19 C18 . . 118.3(2) ?
F3 C19 C20 . . 118.2(2) ?
C18 C19 C20 . . 123.4(2) ?
C19 C20 C21 . . 117.9(2) ?
C19 C20 H20 . . 121.1 ?
C21 C20 H20 . . 121.1 ?
C16 C21 H21 . . 119.7 ?
C20 C21 C16 . . 120.6(2) ?
C20 C21 H21 . . 119.7 ?
N1 C22 C23 . . 122.71(17) ?
N1 C22 H22 . . 118.6 ?
C23 C22 H22 . . 118.6 ?
C22 C23 H23 . . 120.7 ?
C24 C23 C22 . . 118.69(18) ?
C24 C23 H23 . . 120.7 ?
C23 C24 C27 . . 123.94(17) ?
C25 C24 C23 . . 118.34(17) ?
C25 C24 C27 . . 117.70(17) ?
C24 C25 H25 . . 120.3 ?
C26 C25 C24 . . 119.47(18) ?
C26 C25 H25 . . 120.3 ?
N1 C26 C25 . . 122.45(18) ?
N1 C26 H26 . . 118.8 ?
C25 C26 H26 . . 118.8 ?
O7 C27 N2 . . 123.15(17) ?
O7 C27 C24 . . 118.91(17) ?
N2 C27 C24 . . 117.93(17) ?
N3 C28 C29 . . 122.77(17) ?
N3 C28 H28 . . 118.6 ?
C29 C28 H28 . . 118.6 ?
C28 C29 C30 . . 118.84(18) ?
C28 C29 H29 . . 120.6 ?
C30 C29 H29 . . 120.6 ?
C29 C30 C33 . . 124.01(17) ?
C31 C30 C29 . . 118.32(17) ?
C31 C30 C33 . . 117.58(17) ?
C30 C31 H31 . . 120.3 ?
C32 C31 C30 . . 119.37(18) ?
C32 C31 H31 . . 120.3 ?
N3 C32 C31 . . 122.47(18) ?
N3 C32 H32 . . 118.8 ?
C31 C32 H32 . . 118.8 ?
O8 C33 N4 . . 123.07(18) ?
O8 C33 C30 . . 118.78(17) ?
N4 C33 C30 . . 118.15(17) ?
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 O1 . 2.0661(13) y
Cu1 O2 . 2.4581(14) y
Cu1 O3 . 2.2397(14) y
Cu1 O5 . 1.9701(14) y
Cu1 N1 . 2.0024(15) y
Cu1 N3 . 2.0084(15) y
O1 C1 . 1.283(2) ?
O2 C1 . 1.252(2) ?
O3 C8 . 1.233(2) ?
O4 C8 . 1.294(2) ?
O4 H41 . 0.855(18) ?
O5 C15 . 1.266(2) ?
O6 C15 . 1.256(3) ?
O7 C27 . 1.237(2) ?
O8 C33 . 1.232(2) ?
N1 C22 . 1.338(3) ?
N1 C26 . 1.342(2) ?
N2 C27 . 1.331(3) ?
N2 H2A . 0.83(3) ?
N2 H2B . 0.89(3) ?
N3 C28 . 1.339(2) ?
N3 C32 . 1.345(2) ?
N4 C33 . 1.329(3) ?
N4 H4A . 0.79(3) ?
N4 H4B . 0.81(3) ?
F1 C5 . 1.361(2) ?
F2 C12 . 1.356(2) ?
F3 C19 . 1.362(2) ?
C1 C2 . 1.494(3) ?
C2 C3 . 1.393(3) ?
C2 C7 . 1.388(3) ?
C3 H3 . 0.9300 ?
C4 C3 . 1.388(3) ?
C4 C5 . 1.372(3) ?
C4 H4 . 0.9300 ?
C6 C5 . 1.373(3) ?
C6 C7 . 1.381(3) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C9 C8 . 1.490(3) ?
C9 C10 . 1.391(3) ?
C9 C14 . 1.389(3) ?
C10 C11 . 1.386(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.380(3) ?
C11 H11 . 0.9300 ?
C13 C12 . 1.375(3) ?
C13 C14 . 1.384(3) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C16 C15 . 1.498(3) ?
C16 C17 . 1.389(3) ?
C16 C21 . 1.387(3) ?
C17 H17 . 0.9300 ?
C18 C17 . 1.388(3) ?
C18 H18 . 0.9300 ?
C19 C18 . 1.372(3) ?
C20 C19 . 1.372(3) ?
C20 C21 . 1.387(3) ?
C20 H20 . 0.9300 ?
C21 H21 . 0.9300 ?
C22 H22 . 0.9300 ?
C23 C22 . 1.393(3) ?
C23 C24 . 1.390(3) ?
C23 H23 . 0.9300 ?
C24 C27 . 1.515(2) ?
C25 C24 . 1.387(3) ?
C25 C26 . 1.381(3) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
C28 C29 . 1.387(2) ?
C28 H28 . 0.9300 ?
C29 H29 . 0.9300 ?
C30 C31 . 1.385(3) ?
C30 C29 . 1.394(3) ?
C31 C32 . 1.383(3) ?
C31 H31 . 0.9300 ?
C32 H32 . 0.9300 ?
C33 C30 . 1.510(2) ?
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
_geom_hbond_publ_flag
N2 H2A O7 2_646 0.83(3) 2.17(4) 2.990(3) 175(3) yes
N2 H2B O2 2_656 0.90(3) 2.07(3) 2.943(2) 163(3) yes
N4 H4A O1 2_555 0.79(3) 2.18(3) 2.953(2) 165(3) yes
N4 H4B O8 2_565 0.80(3) 2.08(3) 2.880(3) 174(2) yes
O4 H41 O6 . 0.85(3) 1.62(3) 2.457(2) 169(3) yes
C4 H4 F2 2_545 0.93 2.50 3.248(3) 137 yes
C23 H23 O2 2_656 0.93 2.42 3.333(2) 167 yes
C25 H25 O8 1_545 0.93 2.60 3.275(2) 130 yes
C31 H31 O7 1_565 0.93 2.55 3.251(3) 132 yes
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O3 Cu1 O1 C1 . . . . -179.56(10) ?
O5 Cu1 O1 C1 . . . . 0.34(17) ?
N1 Cu1 O1 C1 . . . . -89.15(11) ?
N3 Cu1 O1 C1 . . . . 87.19(11) ?
O1 Cu1 O3 C8 . . . . 176.08(16) ?
O5 Cu1 O3 C8 . . . . -3.87(18) ?
N1 Cu1 O3 C8 . . . . 88.12(17) ?
N3 Cu1 O3 C8 . . . . -97.24(17) ?
O1 Cu1 O5 C15 . . . . 133.63(16) ?
O3 Cu1 O5 C15 . . . . -46.47(17) ?
N1 Cu1 O5 C15 . . . . -137.80(17) ?
N3 Cu1 O5 C15 . . . . 48.11(17) ?
O1 Cu1 N1 C22 . . . . 112.45(15) ?
O1 Cu1 N1 C26 . . . . -54.95(15) ?
O3 Cu1 N1 C22 . . . . -152.53(15) ?
O3 Cu1 N1 C26 . . . . 40.06(15) ?
O5 Cu1 N1 C22 . . . . -39.36(15) ?
O5 Cu1 N1 C26 . . . . 153.23(15) ?
O1 Cu1 N3 C28 . . . . 70.36(15) ?
O1 Cu1 N3 C32 . . . . -102.90(15) ?
O3 Cu1 N3 C28 . . . . -24.46(15) ?
O3 Cu1 N3 C32 . . . . 162.27(14) ?
O5 Cu1 N3 C28 . . . . -137.78(15) ?
O5 Cu1 N3 C32 . . . . 48.95(15) ?
Cu1 O1 C1 O2 . . . . 2.02(18) ?
Cu1 O1 C1 C2 . . . . -177.69(13) ?
Cu1 O3 C8 O4 . . . . 21.5(3) ?
Cu1 O3 C8 C9 . . . . -159.07(13) ?
Cu1 O5 C15 O6 . . . . 28.1(3) ?
Cu1 O5 C15 C16 . . . . -149.96(14) ?
Cu1 N1 C22 C23 . . . . -165.88(15) ?
C26 N1 C22 C23 . . . . 1.7(3) ?
Cu1 N1 C26 C25 . . . . 165.40(15) ?
C22 N1 C26 C25 . . . . -2.3(3) ?
Cu1 N3 C28 C29 . . . . -175.61(14) ?
C32 N3 C28 C29 . . . . -2.3(3) ?
Cu1 N3 C32 C31 . . . . 174.44(15) ?
C28 N3 C32 C31 . . . . 0.9(3) ?
O1 C1 C2 C3 . . . . -11.5(3) ?
O1 C1 C2 C7 . . . . 169.33(17) ?
O2 C1 C2 C3 . . . . 168.76(17) ?
O2 C1 C2 C7 . . . . -10.4(3) ?
C1 C2 C3 C4 . . . . -179.11(18) ?
C7 C2 C3 C4 . . . . 0.0(3) ?
C1 C2 C7 C6 . . . . 179.76(18) ?
C3 C2 C7 C6 . . . . 0.6(3) ?
C5 C4 C3 C2 . . . . -0.1(3) ?
C3 C4 C5 F1 . . . . -179.61(18) ?
C3 C4 C5 C6 . . . . -0.4(3) ?
C7 C6 C5 F1 . . . . -179.78(18) ?
C7 C6 C5 C4 . . . . 1.0(3) ?
C5 C6 C7 C2 . . . . -1.1(3) ?
C10 C9 C8 O3 . . . . 7.4(3) ?
C10 C9 C8 O4 . . . . -173.04(18) ?
C14 C9 C8 O3 . . . . -172.14(18) ?
C14 C9 C8 O4 . . . . 7.4(3) ?
C8 C9 C10 C11 . . . . 179.4(2) ?
C14 C9 C10 C11 . . . . -1.0(3) ?
C8 C9 C14 C13 . . . . 179.55(19) ?
C10 C9 C14 C13 . . . . 0.0(3) ?
C9 C10 C11 C12 . . . . 0.7(3) ?
C10 C11 C12 F2 . . . . -178.4(2) ?
C10 C11 C12 C13 . . . . 0.7(3) ?
C14 C13 C12 F2 . . . . 177.43(19) ?
C14 C13 C12 C11 . . . . -1.7(3) ?
C12 C13 C14 C9 . . . . 1.3(3) ?
C17 C16 C15 O5 . . . . -177.41(19) ?
C17 C16 C15 O6 . . . . 4.4(3) ?
C21 C16 C15 O5 . . . . 4.9(3) ?
C21 C16 C15 O6 . . . . -173.34(19) ?
C15 C16 C17 C18 . . . . -178.52(19) ?
C21 C16 C17 C18 . . . . -0.8(3) ?
C15 C16 C21 C20 . . . . 177.92(19) ?
C17 C16 C21 C20 . . . . 0.2(3) ?
C19 C18 C17 C16 . . . . 0.4(3) ?
F3 C19 C18 C17 . . . . -179.8(2) ?
C20 C19 C18 C17 . . . . 0.6(4) ?
C21 C20 C19 F3 . . . . 179.21(19) ?
C21 C20 C19 C18 . . . . -1.1(3) ?
C19 C20 C21 C16 . . . . 0.7(3) ?
C24 C23 C22 N1 . . . . 0.5(3) ?
C22 C23 C24 C25 . . . . -2.1(3) ?
C22 C23 C24 C27 . . . . 176.20(18) ?
C23 C24 C27 O7 . . . . -172.7(2) ?
C23 C24 C27 N2 . . . . 6.4(3) ?
C25 C24 C27 O7 . . . . 5.6(3) ?
C25 C24 C27 N2 . . . . -175.24(18) ?
C26 C25 C24 C23 . . . . 1.6(3) ?
C26 C25 C24 C27 . . . . -176.86(18) ?
C24 C25 C26 N1 . . . . 0.7(3) ?
N3 C28 C29 C30 . . . . 1.6(3) ?
C31 C30 C29 C28 . . . . 0.5(3) ?
C33 C30 C29 C28 . . . . -175.99(18) ?
C29 C30 C31 C32 . . . . -1.8(3) ?
C33 C30 C31 C32 . . . . 174.95(18) ?
C30 C31 C32 N3 . . . . 1.1(3) ?
O8 C33 C30 C29 . . . . 165.5(2) ?
O8 C33 C30 C31 . . . . -10.9(3) ?
N4 C33 C30 C29 . . . . -13.6(3) ?
N4 C33 C30 C31 . . . . 169.95(19) ?
