#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/45/2224511.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_2224511
loop_
_publ_author_name
'Hökelek, Tuncer'
'Yılmaz, Filiz'
'Tercan, Barış'
'Özbek, F. Elif'
'Necefoğlu, Hacali'
_publ_section_title
;Bis(μ-2-fluorobenzoato-1:2κ²O:O')(2-fluorobenzoato-1κ²O,O')(2-fluorobenzoato-2κO)dinicotinamide-1κN¹,2κN¹-dizinc(II)--2-fluorobenzoic
 acid (1/1)
;
_journal_coeditor_code           XU2668
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1608
_journal_page_last               m1609
_journal_paper_doi               10.1107/S1600536809048089
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac
'[Zn2 (C7 H4 F O2)4 (C6 H6 N2 O)2], C7 H5 F O2'
_chemical_formula_moiety         'C40 H28 F4 N4 O10 Zn2, C7 H5 F O2'
_chemical_formula_sum            'C47 H33 F5 N4 O12 Zn2'
_chemical_formula_weight         1071.55
_chemical_name_systematic
;
Bis(μ-2-fluorobenzoato-1:2κ²O:O')(2-fluorobenzoato-
1κ²O,O')(2-fluorobenzoato-2κO)dinicotinamide-
1κN¹,2κN¹-dizinc(II)--2-fluorobenzoic acid (1/1)
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.929(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5143(2)
_cell_length_b                   16.7106(3)
_cell_length_c                   20.6673(4)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      2.30
_cell_volume                     4316.33(13)
_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)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Kappa APEXII 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  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            37814
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    1.205
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.386
_refine_diff_density_min         -0.588
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     659
_refine_ls_number_reflns         10696
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.771
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0383P)²+3.8099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0965
_reflns_number_gt                7459
_reflns_number_total             10696
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2668.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224511
_cod_database_fobs_code          2224511
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_disorder_assembly
_atom_site_disorder_group
Zn Zn1 0.17153(4) 0.67257(3) 0.24483(2) 0.01406(14) Uani d . 1 . .
Zn Zn2 0.31257(4) 0.51261(3) 0.29078(3) 0.01641(14) Uani d . 1 . .
F F1 -0.0139(2) 0.6414(2) 0.02860(15) 0.0383(8) Uani d . 1 . .
F F2 0.1234(3) 0.4736(2) 0.09432(18) 0.0236(9) Uani d P 0.70 . .
F F2' 0.4720(5) 0.5834(7) 0.0809(5) 0.054(3) Uiso d PD 0.30 . .
F F3 -0.0844(2) 0.64099(18) 0.36234(15) 0.0362(8) Uani d . 1 . .
F F4 0.6020(3) 0.6154(2) 0.3631(2) 0.0291(10) Uani d P 0.70 . .
F F4' 0.3673(4) 0.8400(4) 0.3434(4) 0.0138(17) Uiso d PD 0.30 . .
F F5 0.4883(2) 0.73739(19) 0.00733(15) 0.0377(8) Uani d . 1 . .
O O1 0.0703(3) 0.6540(2) 0.15019(15) 0.0240(8) Uani d . 1 . .
O O2 0.2346(2) 0.6999(2) 0.16036(14) 0.0199(7) Uani d . 1 . .
O O3 0.2399(2) 0.5160(2) 0.20262(16) 0.0270(8) Uani d . 1 . .
O O4 0.4067(2) 0.5492(2) 0.19029(16) 0.0242(8) Uani d . 1 . .
O O5 0.0874(2) 0.60130(18) 0.29767(14) 0.0163(7) Uani d . 1 . .
O O6 0.1828(2) 0.49874(19) 0.34017(15) 0.0199(7) Uani d . 1 . .
O O7 0.3061(2) 0.6981(2) 0.29769(14) 0.0182(7) Uani d . 1 . .
O O8 0.4007(2) 0.59306(19) 0.33526(16) 0.0211(7) Uani d . 1 . .
O O9 0.2568(3) 0.9875(2) 0.26713(19) 0.0319(9) Uani d . 1 . .
O O10 0.2451(2) 0.2018(2) 0.27913(16) 0.0228(8) Uani d . 1 . .
O O11 0.6174(3) 0.9659(2) 0.0211(2) 0.0380(10) Uani d . 1 . .
O O12 0.4706(3) 0.8936(2) 0.00208(19) 0.0331(9) Uani d . 1 . .
H H121 0.443(5) 0.943(5) -0.008(3) 0.07(2) Uiso d . 1 . .
N N1 0.0910(3) 0.7776(2) 0.26319(17) 0.0148(8) Uani d . 1 . .
N N2 0.1202(4) 1.0617(3) 0.3008(2) 0.0235(10) Uani d . 1 . .
H H2A 0.058(4) 1.063(3) 0.310(2) 0.022(14) Uiso d . 1 . .
H H2B 0.158(4) 1.102(3) 0.296(3) 0.030(16) Uiso d . 1 . .
N N3 0.4006(3) 0.4123(2) 0.30545(17) 0.0142(8) Uani d . 1 . .
N N4 0.3912(4) 0.1241(3) 0.2944(2) 0.0209(9) Uani d . 1 . .
H H4A 0.454(4) 0.120(3) 0.304(2) 0.024(15) Uiso d . 1 . .
H H4B 0.347(5) 0.082(4) 0.284(3) 0.06(2) Uiso d . 1 . .
C C1 0.1502(4) 0.6839(3) 0.1255(2) 0.0172(10) Uani d . 1 . .
C C2 0.1499(3) 0.7054(3) 0.0554(2) 0.0163(10) Uani d . 1 . .
C C3 0.0668(4) 0.6878(3) 0.0113(2) 0.0203(10) Uani d . 1 . .
C C4 0.0640(4) 0.7140(3) -0.0521(2) 0.0273(12) Uani d . 1 . .
H H4 0.0060 0.7019 -0.0803 0.033 Uiso calc R 1 . .
C C5 0.1486(4) 0.7584(3) -0.0729(2) 0.0290(12) Uani d . 1 . .
H H5 0.1472 0.7774 -0.1152 0.035 Uiso calc R 1 . .
C C6 0.2351(4) 0.7745(3) -0.0310(2) 0.0255(12) Uani d . 1 . .
H H6 0.2931 0.8030 -0.0455 0.031 Uiso calc R 1 . .
C C7 0.2356(4) 0.7483(3) 0.0323(2) 0.0196(10) Uani d . 1 . .
H H7 0.2944 0.7595 0.0602 0.023 Uiso calc R 1 . .
C C8 0.3164(3) 0.5334(3) 0.1666(2) 0.0179(10) Uani d . 1 . .
C C9 0.2958(3) 0.5326(3) 0.0950(2) 0.0169(10) Uani d D 1 . .
C C10 0.2015(4) 0.5058(3) 0.0629(2) 0.0230(11) Uani d D 1 . .
H H14' 0.1473 0.4853 0.0872 0.028 Uiso calc PR 0.30 . .
C C11 0.1859(4) 0.5086(3) -0.0046(3) 0.0282(12) Uani d D 1 . .
H H11 0.1222 0.4903 -0.0246 0.034 Uiso calc R 1 . .
C C12 0.2649(4) 0.5383(3) -0.0407(3) 0.0312(13) Uani d . 1 . .
H H12 0.2543 0.5405 -0.0855 0.037 Uiso calc R 1 . .
C C13 0.3598(4) 0.5651(3) -0.0124(2) 0.0306(13) Uani d D 1 . .
H H13 0.4132 0.5850 -0.0377 0.037 Uiso calc R 1 . .
C C14 0.3749(4) 0.5620(3) 0.0552(2) 0.0234(11) Uani d D 1 . .
H H14 0.4394 0.5799 0.0744 0.028 Uiso calc PR 0.70 . .
C C15 0.0994(3) 0.5414(3) 0.3341(2) 0.0145(9) Uani d . 1 . .
C C16 0.0079(3) 0.5168(3) 0.3735(2) 0.0164(10) Uani d . 1 . .
C C17 -0.0787(4) 0.5654(3) 0.3857(2) 0.0218(11) Uani d . 1 . .
C C18 -0.1606(4) 0.5413(3) 0.4231(2) 0.0286(12) Uani d . 1 . .
H H18 -0.2176 0.5754 0.4301 0.034 Uiso calc R 1 . .
C C19 -0.1571(4) 0.4659(4) 0.4501(3) 0.0362(14) Uani d . 1 . .
H H19 -0.2119 0.4489 0.4756 0.043 Uiso calc R 1 . .
C C20 -0.0727(4) 0.4155(3) 0.4393(3) 0.0367(14) Uani d . 1 . .
H H20 -0.0700 0.3647 0.4576 0.044 Uiso calc R 1 . .
C C21 0.0082(4) 0.4410(3) 0.4010(2) 0.0258(12) Uani d . 1 . .
H H21 0.0644 0.4064 0.3934 0.031 Uiso calc R 1 . .
C C22 0.3881(3) 0.6668(3) 0.3252(2) 0.0158(10) Uani d . 1 . .
C C23 0.4772(3) 0.7209(3) 0.3453(2) 0.0141(9) Uani d D 1 . .
C C24 0.5816(3) 0.6927(3) 0.3596(2) 0.0174(10) Uani d D 1 . .
H H28' 0.5940 0.6378 0.3605 0.021 Uiso calc PR 0.30 . .
C C25 0.6675(4) 0.7452(3) 0.3726(2) 0.0216(11) Uani d D 1 . .
H H25 0.7362 0.7253 0.3811 0.026 Uiso calc R 1 . .
C C26 0.6492(4) 0.8258(3) 0.3728(2) 0.0216(11) Uani d . 1 . .
H H26 0.7064 0.8605 0.3812 0.026 Uiso calc R 1 . .
C C27 0.5482(4) 0.8570(3) 0.3608(2) 0.0214(11) Uani d D 1 . .
H H27 0.5364 0.9119 0.3621 0.026 Uiso calc R 1 . .
C C28 0.4637(3) 0.8040(3) 0.3467(2) 0.0186(10) Uani d D 1 . .
H H28 0.3957 0.8248 0.3378 0.022 Uiso calc PR 0.70 . .
C C29 0.1429(3) 0.8473(3) 0.2675(2) 0.0146(9) Uani d . 1 . .
H H29 0.2162 0.8472 0.2620 0.018 Uiso calc R 1 . .
C C30 0.0941(3) 0.9198(3) 0.2797(2) 0.0150(10) Uani d . 1 . .
C C31 -0.0155(3) 0.9193(3) 0.2884(2) 0.0168(10) Uani d . 1 . .
H H31 -0.0515 0.9665 0.2972 0.020 Uiso calc R 1 . .
C C32 -0.0698(3) 0.8475(3) 0.2837(2) 0.0181(10) Uani d . 1 . .
H H32 -0.1430 0.8459 0.2895 0.022 Uiso calc R 1 . .
C C33 -0.0157(3) 0.7782(3) 0.2707(2) 0.0168(10) Uani d . 1 . .
H H33 -0.0536 0.7304 0.2668 0.020 Uiso calc R 1 . .
C C34 0.1630(3) 0.9929(3) 0.2819(2) 0.0187(10) Uani d . 1 . .
C C35 0.3537(3) 0.3409(3) 0.2987(2) 0.0142(9) Uani d . 1 . .
H H35 0.2799 0.3393 0.2906 0.017 Uiso calc R 1 . .
C C36 0.4082(3) 0.2690(3) 0.3032(2) 0.0133(9) Uani d . 1 . .
C C37 0.5183(3) 0.2716(3) 0.3166(2) 0.0170(10) Uani d . 1 . .
H H37 0.5579 0.2246 0.3204 0.020 Uiso calc R 1 . .
C C38 0.5676(3) 0.3453(3) 0.3241(2) 0.0184(10) Uani d . 1 . .
H H38 0.6409 0.3483 0.3336 0.022 Uiso calc R 1 . .
C C39 0.5075(3) 0.4143(3) 0.3175(2) 0.0174(10) Uani d . 1 . .
H H39 0.5418 0.4636 0.3214 0.021 Uiso calc R 1 . .
C C40 0.3426(3) 0.1945(3) 0.2915(2) 0.0169(10) Uani d . 1 . .
C C41 0.7570(4) 0.6917(3) 0.0614(3) 0.0303(12) Uani d . 1 . .
H H41 0.7990 0.6469 0.0709 0.036 Uiso calc R 1 . .
C C42 0.6512(4) 0.6824(3) 0.0410(2) 0.0269(12) Uani d . 1 . .
H H42 0.6215 0.6316 0.0367 0.032 Uiso calc R 1 . .
C C43 0.5899(4) 0.7494(3) 0.0272(2) 0.0225(11) Uani d . 1 . .
C C44 0.6319(4) 0.8263(3) 0.0324(2) 0.0195(10) Uani d . 1 . .
C C45 0.7393(4) 0.8332(3) 0.0534(2) 0.0268(12) Uani d . 1 . .
H H45 0.7699 0.8838 0.0578 0.032 Uiso calc R 1 . .
C C46 0.8006(4) 0.7669(3) 0.0677(3) 0.0329(13) Uani d . 1 . .
H H46 0.8719 0.7729 0.0817 0.039 Uiso calc R 1 . .
C C47 0.5720(4) 0.9010(3) 0.0178(2) 0.0214(11) Uani d . 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'
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'
Zn Zn 0.2839 1.4301 '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 Zn1 O1 . . 60.92(12) ?
O2 Zn1 N1 . . 100.57(14) ?
O5 Zn1 O1 . . 95.98(12) ?
O5 Zn1 O2 . . 150.56(13) ?
O5 Zn1 O7 . . 106.60(12) ?
O5 Zn1 N1 . . 97.64(13) ?
O7 Zn1 O1 . . 154.68(12) ?
O7 Zn1 O2 . . 93.94(12) ?
O7 Zn1 N1 . . 97.05(13) ?
N1 Zn1 O1 . . 91.04(13) ?
O3 Zn2 N3 . . 112.33(15) ?
O6 Zn2 O3 . . 97.28(12) ?
O6 Zn2 N3 . . 106.36(14) ?
O8 Zn2 O3 . . 129.40(14) ?
O8 Zn2 O6 . . 107.39(13) ?
O8 Zn2 N3 . . 102.19(14) ?
C1 O1 Zn1 . . 82.8(3) ?
C1 O2 Zn1 . . 95.3(3) ?
C8 O3 Zn2 . . 102.6(3) ?
C15 O5 Zn1 . . 140.1(3) ?
C15 O6 Zn2 . . 125.3(3) ?
C22 O7 Zn1 . . 143.0(3) ?
C22 O8 Zn2 . . 122.4(3) ?
C47 O12 H121 . . 109(4) ?
C29 N1 Zn1 . . 120.9(3) ?
C29 N1 C33 . . 117.7(4) ?
C33 N1 Zn1 . . 121.4(3) ?
C34 N2 H2A . . 120(4) ?
C34 N2 H2B . . 115(4) ?
H2A N2 H2B . . 124(5) ?
C35 N3 Zn2 . . 119.5(3) ?
C35 N3 C39 . . 118.0(4) ?
C39 N3 Zn2 . . 122.4(3) ?
C40 N4 H4A . . 122(4) ?
C40 N4 H4B . . 114(4) ?
H4A N4 H4B . . 124(5) ?
O1 C1 O2 . . 120.7(4) ?
O1 C1 C2 . . 122.0(4) ?
O2 C1 C2 . . 117.3(4) ?
C3 C2 C1 . . 123.7(4) ?
C3 C2 C7 . . 116.8(4) ?
C7 C2 C1 . . 119.5(4) ?
F1 C3 C2 . . 120.1(4) ?
F1 C3 C4 . . 117.1(4) ?
C4 C3 C2 . . 122.8(4) ?
C3 C4 H4 . . 120.5 ?
C5 C4 C3 . . 118.9(5) ?
C5 C4 H4 . . 120.5 ?
C4 C5 H5 . . 120.0 ?
C6 C5 C4 . . 120.1(5) ?
C6 C5 H5 . . 120.0 ?
C5 C6 C7 . . 119.9(5) ?
C5 C6 H6 . . 120.1 ?
C7 C6 H6 . . 120.1 ?
C2 C7 H7 . . 119.3 ?
C6 C7 C2 . . 121.4(4) ?
C6 C7 H7 . . 119.3 ?
O3 C8 C9 . . 118.7(4) ?
O4 C8 O3 . . 121.1(4) ?
O4 C8 C9 . . 120.2(4) ?
C10 C9 C8 . . 125.0(4) ?
C14 C9 C10 . . 115.9(4) ?
C14 C9 C8 . . 119.1(4) ?
C9 C10 H14' . . 118.9 ?
C11 C10 C9 . . 122.3(4) ?
C11 C10 H14' . . 118.9 ?
C10 C11 H11 . . 120.3 ?
C12 C11 C10 . . 119.4(5) ?
C12 C11 H11 . . 120.3 ?
C11 C12 C13 . . 121.5(5) ?
C11 C12 H12 . . 119.3 ?
C13 C12 H12 . . 119.3 ?
C12 C13 C14 . . 118.9(5) ?
C12 C13 H13 . . 120.6 ?
C14 C13 H13 . . 120.6 ?
C9 C14 C13 . . 122.2(4) ?
C9 C14 H14 . . 118.9 ?
C13 C14 H14 . . 118.9 ?
O5 C15 O6 . . 125.5(4) ?
O5 C15 C16 . . 118.4(4) ?
O6 C15 C16 . . 116.1(4) ?
C17 C16 C15 . . 124.3(4) ?
C21 C16 C15 . . 119.2(4) ?
C21 C16 C17 . . 116.4(4) ?
F3 C17 C16 . . 120.6(4) ?
F3 C17 C18 . . 116.6(4) ?
C18 C17 C16 . . 122.8(5) ?
C17 C18 C19 . . 119.1(5) ?
C17 C18 H18 . . 120.4 ?
C19 C18 H18 . . 120.4 ?
C18 C19 C20 . . 120.1(5) ?
C18 C19 H19 . . 120.0 ?
C20 C19 H19 . . 120.0 ?
C19 C20 C21 . . 119.6(5) ?
C19 C20 H20 . . 120.2 ?
C21 C20 H20 . . 120.2 ?
C16 C21 H21 . . 119.0 ?
C20 C21 C16 . . 121.9(5) ?
C20 C21 H21 . . 119.0 ?
O7 C22 C23 . . 117.3(4) ?
O8 C22 O7 . . 124.9(4) ?
O8 C22 C23 . . 117.7(4) ?
C24 C23 C22 . . 122.2(4) ?
C28 C23 C22 . . 121.5(4) ?
C28 C23 C24 . . 116.2(4) ?
C23 C24 H28' . . 119.2 ?
C25 C24 C23 . . 121.6(4) ?
C25 C24 H28' . . 119.2 ?
C24 C25 H25 . . 120.3 ?
C26 C25 C24 . . 119.4(4) ?
C26 C25 H25 . . 120.3 ?
C25 C26 C27 . . 121.6(4) ?
C25 C26 H26 . . 119.2 ?
C27 C26 H26 . . 119.2 ?
C26 C27 C28 . . 118.4(4) ?
C26 C27 H27 . . 120.8 ?
C28 C27 H27 . . 120.8 ?
C23 C28 C27 . . 122.8(4) ?
C23 C28 H28 . . 118.6 ?
C27 C28 H28 . . 118.6 ?
N1 C29 C30 . . 123.9(4) ?
N1 C29 H29 . . 118.0 ?
C30 C29 H29 . . 118.0 ?
C29 C30 C31 . . 117.7(4) ?
C29 C30 C34 . . 117.4(4) ?
C31 C30 C34 . . 124.9(4) ?
C30 C31 H31 . . 120.6 ?
C32 C31 C30 . . 118.7(4) ?
C32 C31 H31 . . 120.6 ?
C31 C32 H32 . . 120.0 ?
C33 C32 C31 . . 120.1(4) ?
C33 C32 H32 . . 120.0 ?
N1 C33 C32 . . 121.9(4) ?
N1 C33 H33 . . 119.1 ?
C32 C33 H33 . . 119.1 ?
O9 C34 N2 . . 122.5(4) ?
O9 C34 C30 . . 119.3(4) ?
N2 C34 C30 . . 118.3(4) ?
N3 C35 C36 . . 123.8(4) ?
N3 C35 H35 . . 118.1 ?
C36 C35 H35 . . 118.1 ?
C35 C36 C37 . . 117.9(4) ?
C35 C36 C40 . . 116.4(4) ?
C37 C36 C40 . . 125.7(4) ?
C36 C37 H37 . . 120.6 ?
C38 C37 C36 . . 118.8(4) ?
C38 C37 H37 . . 120.6 ?
C37 C38 H38 . . 120.1 ?
C39 C38 C37 . . 119.8(4) ?
C39 C38 H38 . . 120.1 ?
N3 C39 C38 . . 121.8(4) ?
N3 C39 H39 . . 119.1 ?
C38 C39 H39 . . 119.1 ?
O10 C40 N4 . . 122.8(4) ?
O10 C40 C36 . . 118.3(4) ?
N4 C40 C36 . . 118.9(4) ?
C42 C41 H41 . . 119.9 ?
C46 C41 C42 . . 120.2(5) ?
C46 C41 H41 . . 119.9 ?
C41 C42 C43 . . 119.2(5) ?
C41 C42 H42 . . 120.4 ?
C43 C42 H42 . . 120.4 ?
F5 C43 C42 . . 117.0(5) ?
F5 C43 C44 . . 121.0(4) ?
C42 C43 C44 . . 122.0(4) ?
C43 C44 C45 . . 117.1(5) ?
C43 C44 C47 . . 125.3(4) ?
C45 C44 C47 . . 117.6(4) ?
C44 C45 H45 . . 119.4 ?
C46 C45 C44 . . 121.3(5) ?
C46 C45 H45 . . 119.4 ?
C41 C46 H46 . . 119.9 ?
C45 C46 C41 . . 120.3(5) ?
C45 C46 H46 . . 119.9 ?
O11 C47 O12 . . 122.8(5) ?
O11 C47 C44 . . 120.5(4) ?
O12 C47 C44 . . 116.7(5) ?
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
Zn1 O1 . 2.296(3) yes
Zn1 O2 . 2.006(3) yes
Zn1 O5 . 1.958(3) yes
Zn1 O7 . 2.005(3) yes
Zn1 N1 . 2.068(4) yes
Zn2 O3 . 1.995(3) yes
Zn2 O6 . 1.975(3) yes
Zn2 O8 . 1.940(3) yes
Zn2 N3 . 2.021(4) yes
F1 C3 . 1.338(5) ?
F3 C17 . 1.353(6) ?
F5 C43 . 1.331(5) ?
O1 C1 . 1.250(5) ?
O2 C1 . 1.276(5) ?
O3 C8 . 1.276(5) ?
O4 C8 . 1.237(5) ?
O5 C15 . 1.256(5) ?
O6 C15 . 1.266(5) ?
O7 C22 . 1.261(5) ?
O8 C22 . 1.259(5) ?
O9 C34 . 1.231(5) ?
O10 C40 . 1.240(5) ?
O11 C47 . 1.225(6) ?
O12 C47 . 1.301(6) ?
O12 H121 . 0.92(8) ?
N1 C29 . 1.335(6) ?
N1 C33 . 1.353(5) ?
N2 C34 . 1.335(6) ?
N2 H2A . 0.82(5) ?
N2 H2B . 0.84(6) ?
N3 C35 . 1.335(6) ?
N3 C39 . 1.349(5) ?
N4 C40 . 1.324(6) ?
N4 H4A . 0.81(5) ?
N4 H4B . 0.92(7) ?
C2 C1 . 1.494(6) ?
C2 C3 . 1.379(6) ?
C2 C7 . 1.394(6) ?
C3 C4 . 1.379(7) ?
C4 H4 . 0.9300 ?
C5 C4 . 1.379(7) ?
C5 H5 . 0.9300 ?
C6 C5 . 1.378(7) ?
C6 H6 . 0.9300 ?
C7 C6 . 1.380(6) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.490(6) ?
C9 C14 . 1.407(6) ?
C10 C9 . 1.398(6) ?
C10 C11 . 1.398(7) ?
C10 H14' . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C11 . 1.363(7) ?
C12 H12 . 0.9300 ?
C13 C12 . 1.372(7) ?
C13 H13 . 0.9300 ?
C14 C13 . 1.402(7) ?
C14 H14 . 0.9300 ?
C16 C15 . 1.496(6) ?
C16 C17 . 1.389(6) ?
C16 C21 . 1.387(7) ?
C18 C17 . 1.375(6) ?
C18 C19 . 1.378(7) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.378(7) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
C21 C20 . 1.384(7) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.479(6) ?
C24 C23 . 1.406(6) ?
C24 H28' . 0.9300 ?
C25 C24 . 1.403(6) ?
C25 H25 . 0.9300 ?
C26 C25 . 1.367(7) ?
C26 C27 . 1.378(7) ?
C26 H26 . 0.9300 ?
C27 C28 . 1.398(6) ?
C27 H27 . 0.9300 ?
C28 C23 . 1.398(6) ?
C28 H28 . 0.9300 ?
C29 C30 . 1.387(6) ?
C29 H29 . 0.9300 ?
C31 C30 . 1.392(6) ?
C31 C32 . 1.380(7) ?
C31 H31 . 0.9300 ?
C32 H32 . 0.9300 ?
C33 C32 . 1.374(6) ?
C33 H33 . 0.9300 ?
C34 C30 . 1.494(6) ?
C35 H35 . 0.9300 ?
C36 C35 . 1.382(6) ?
C36 C37 . 1.391(6) ?
C36 C40 . 1.504(6) ?
C37 C38 . 1.382(6) ?
C37 H37 . 0.9300 ?
C38 H38 . 0.9300 ?
C39 C38 . 1.380(6) ?
C39 H39 . 0.9300 ?
C41 C46 . 1.374(8) ?
C41 H41 . 0.9300 ?
C42 C41 . 1.377(7) ?
C42 H42 . 0.9300 ?
C43 C42 . 1.379(7) ?
C44 C43 . 1.391(7) ?
C44 C47 . 1.479(7) ?
C45 C44 . 1.395(6) ?
C45 C46 . 1.371(7) ?
C45 H45 . 0.9300 ?
C46 H46 . 0.9300 ?
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 O1 2_555 0.82(5) 2.39(5) 3.056(6) 140(5) yes
N2 H2B O10 1_565 0.84(6) 2.03(5) 2.863(6) 176.4(5) yes
N4 H4A O4 2_645 0.81(5) 2.11(5) 2.825(5) 149(5) yes
N4 H4B O9 1_545 0.92(7) 1.96(7) 2.874(6) 176(7) yes
O12 H121 O11 3_675 0.92(8) 1.71(8) 2.626(5) 174(6) 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
O2 Zn1 O1 C1 . . . . -3.1(3) ?
O5 Zn1 O1 C1 . . . . -163.8(3) ?
O7 Zn1 O1 C1 . . . . -10.6(4) ?
N1 Zn1 O1 C1 . . . . 98.4(3) ?
O1 Zn1 O2 C1 . . . . 3.0(2) ?
O5 Zn1 O2 C1 . . . . 45.1(4) ?
O7 Zn1 O2 C1 . . . . 179.9(3) ?
N1 Zn1 O2 C1 . . . . -82.2(3) ?
O1 Zn1 O5 C15 . . . . 125.1(5) ?
O2 Zn1 O5 C15 . . . . 89.0(5) ?
O7 Zn1 O5 C15 . . . . -43.3(5) ?
N1 Zn1 O5 C15 . . . . -143.1(5) ?
O1 Zn1 O7 C22 . . . . -91.5(5) ?
O2 Zn1 O7 C22 . . . . -98.0(5) ?
O5 Zn1 O7 C22 . . . . 60.6(5) ?
N1 Zn1 O7 C22 . . . . 160.8(5) ?
O1 Zn1 N1 C29 . . . . -118.6(3) ?
O1 Zn1 N1 C33 . . . . 60.8(3) ?
O2 Zn1 N1 C29 . . . . -58.0(3) ?
O2 Zn1 N1 C33 . . . . 121.4(3) ?
O5 Zn1 N1 C29 . . . . 145.2(3) ?
O5 Zn1 N1 C33 . . . . -35.4(3) ?
O7 Zn1 N1 C29 . . . . 37.3(3) ?
O7 Zn1 N1 C33 . . . . -143.2(3) ?
O8 Zn2 O3 C8 . . . . 53.8(3) ?
O6 Zn2 O3 C8 . . . . 173.4(3) ?
N3 Zn2 O3 C8 . . . . -75.5(3) ?
O3 Zn2 O6 C15 . . . . -50.5(4) ?
O8 Zn2 O6 C15 . . . . 84.8(4) ?
N3 Zn2 O6 C15 . . . . -166.4(3) ?
O3 Zn2 O8 C22 . . . . 29.6(4) ?
O6 Zn2 O8 C22 . . . . -85.8(3) ?
N3 Zn2 O8 C22 . . . . 162.5(3) ?
O3 Zn2 N3 C35 . . . . -57.3(3) ?
O3 Zn2 N3 C39 . . . . 117.9(3) ?
O6 Zn2 N3 C35 . . . . 48.0(3) ?
O6 Zn2 N3 C39 . . . . -136.8(3) ?
O8 Zn2 N3 C35 . . . . 160.4(3) ?
O8 Zn2 N3 C39 . . . . -24.3(4) ?
Zn1 O1 C1 O2 . . . . 5.0(4) ?
Zn1 O1 C1 C2 . . . . -172.5(4) ?
Zn1 O2 C1 O1 . . . . -5.7(5) ?
Zn1 O2 C1 C2 . . . . 171.9(3) ?
Zn2 O3 C8 O4 . . . . -5.4(5) ?
Zn2 O3 C8 C9 . . . . 173.4(3) ?
Zn1 O5 C15 O6 . . . . -11.4(8) ?
Zn1 O5 C15 C16 . . . . 169.4(3) ?
Zn2 O6 C15 O5 . . . . -3.1(6) ?
Zn2 O6 C15 C16 . . . . 176.2(3) ?
Zn1 O7 C22 O8 . . . . -12.9(7) ?
Zn1 O7 C22 C23 . . . . 165.3(3) ?
Zn2 O8 C22 O7 . . . . 16.4(6) ?
Zn2 O8 C22 C23 . . . . -161.8(3) ?
Zn1 N1 C29 C30 . . . . -180.0(3) ?
C33 N1 C29 C30 . . . . 0.6(6) ?
Zn1 N1 C33 C32 . . . . 179.1(3) ?
C29 N1 C33 C32 . . . . -1.5(6) ?
Zn2 N3 C35 C36 . . . . 175.3(3) ?
C39 N3 C35 C36 . . . . -0.2(6) ?
Zn2 N3 C39 C38 . . . . -176.6(3) ?
C35 N3 C39 C38 . . . . -1.3(6) ?
C3 C2 C1 O1 . . . . -6.1(7) ?
C3 C2 C1 O2 . . . . 176.3(4) ?
C7 C2 C1 O1 . . . . 171.4(4) ?
C7 C2 C1 O2 . . . . -6.2(6) ?
C1 C2 C3 F1 . . . . -7.9(7) ?
C1 C2 C3 C4 . . . . 174.4(5) ?
C7 C2 C3 F1 . . . . 174.6(4) ?
C7 C2 C3 C4 . . . . -3.2(7) ?
C1 C2 C7 C6 . . . . -175.2(4) ?
C3 C2 C7 C6 . . . . 2.5(7) ?
F1 C3 C4 C5 . . . . -176.5(4) ?
C2 C3 C4 C5 . . . . 1.3(8) ?
C6 C5 C4 C3 . . . . 1.4(8) ?
C7 C6 C5 C4 . . . . -2.0(8) ?
C2 C7 C6 C5 . . . . 0.0(7) ?
O3 C8 C9 C10 . . . . -7.4(7) ?
O3 C8 C9 C14 . . . . 171.5(4) ?
O4 C8 C9 C10 . . . . 171.3(4) ?
O4 C8 C9 C14 . . . . -9.7(7) ?
C10 C9 C14 C13 . . . . 0.8(7) ?
C8 C9 C14 C13 . . . . -178.3(5) ?
C11 C10 C9 C14 . . . . -0.7(7) ?
C11 C10 C9 C8 . . . . 178.3(5) ?
C9 C10 C11 C12 . . . . 0.1(8) ?
C13 C12 C11 C10 . . . . 0.4(8) ?
C14 C13 C12 C11 . . . . -0.4(8) ?
C9 C14 C13 C12 . . . . -0.3(8) ?
C17 C16 C15 O5 . . . . -17.1(7) ?
C17 C16 C15 O6 . . . . 163.6(4) ?
C21 C16 C15 O5 . . . . 163.9(4) ?
C21 C16 C15 O6 . . . . -15.4(6) ?
C15 C16 C17 F3 . . . . -0.8(7) ?
C15 C16 C17 C18 . . . . -178.8(5) ?
C21 C16 C17 F3 . . . . 178.2(4) ?
C21 C16 C17 C18 . . . . 0.2(7) ?
C17 C16 C21 C20 . . . . -0.8(7) ?
C15 C16 C21 C20 . . . . 178.3(5) ?
C19 C18 C17 F3 . . . . -177.8(5) ?
C19 C18 C17 C16 . . . . 0.3(8) ?
C17 C18 C19 C20 . . . . -0.3(9) ?
C18 C19 C20 C21 . . . . -0.3(9) ?
C16 C21 C20 C19 . . . . 0.9(9) ?
O7 C22 C23 C24 . . . . -162.1(4) ?
O7 C22 C23 C28 . . . . 13.1(6) ?
O8 C22 C23 C24 . . . . 16.2(6) ?
O8 C22 C23 C28 . . . . -168.5(4) ?
C25 C24 C23 C28 . . . . -1.8(6) ?
C25 C24 C23 C22 . . . . 173.8(4) ?
C26 C25 C24 C23 . . . . 1.4(7) ?
C27 C26 C25 C24 . . . . 0.3(7) ?
C25 C26 C27 C28 . . . . -1.6(7) ?
C26 C27 C28 C23 . . . . 1.1(7) ?
C27 C28 C23 C24 . . . . 0.5(6) ?
C27 C28 C23 C22 . . . . -175.1(4) ?
N1 C29 C30 C31 . . . . 0.5(7) ?
N1 C29 C30 C34 . . . . -178.9(4) ?
C32 C31 C30 C29 . . . . -0.8(6) ?
C32 C31 C30 C34 . . . . 178.7(4) ?
C30 C31 C32 C33 . . . . -0.1(6) ?
N1 C33 C32 C31 . . . . 1.3(7) ?
N2 C34 C30 C29 . . . . -172.6(4) ?
N2 C34 C30 C31 . . . . 8.0(7) ?
O9 C34 C30 C29 . . . . 6.7(7) ?
O9 C34 C30 C31 . . . . -172.8(4) ?
C37 C36 C35 N3 . . . . 1.1(6) ?
C40 C36 C35 N3 . . . . -177.4(4) ?
C35 C36 C37 C38 . . . . -0.6(6) ?
C40 C36 C37 C38 . . . . 177.9(4) ?
C35 C36 C40 O10 . . . . -0.5(6) ?
C37 C36 C40 O10 . . . . -179.0(4) ?
C35 C36 C40 N4 . . . . 179.2(4) ?
C37 C36 C40 N4 . . . . 0.7(7) ?
C36 C37 C38 C39 . . . . -0.8(6) ?
N3 C39 C38 C37 . . . . 1.8(7) ?
C42 C41 C46 C45 . . . . -0.4(8) ?
C43 C42 C41 C46 . . . . -0.1(8) ?
F5 C43 C42 C41 . . . . 179.6(4) ?
C44 C43 C42 C41 . . . . 0.8(7) ?
C45 C44 C43 F5 . . . . -179.7(4) ?
C45 C44 C43 C42 . . . . -0.9(7) ?
C47 C44 C43 F5 . . . . 0.5(7) ?
C47 C44 C43 C42 . . . . 179.2(4) ?
C43 C44 C47 O11 . . . . -176.7(5) ?
C43 C44 C47 O12 . . . . 3.8(7) ?
C45 C44 C47 O11 . . . . 3.5(7) ?
C45 C44 C47 O12 . . . . -176.0(4) ?
C46 C45 C44 C43 . . . . 0.5(7) ?
C46 C45 C44 C47 . . . . -179.7(5) ?
C44 C45 C46 C41 . . . . 0.2(8) ?
