#------------------------------------------------------------------------------
#$Date: 2022-03-03 00:52:16 +0100 (jue 03 de mar de 2022) $
#$Revision: 273212 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/96/7709632.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_7709632
loop_
_publ_author_name
'Icsel, Ceyda'
'Yilmaz, Veysel T.'
'Aygün, Muhittin'
'Erkisa, merve'
'Ulukaya, Engin'
_publ_section_title
;
 Novel 5-fluorouracil complexes of Zn(II) with pyridine-based ligands as
 potential anticancer agents
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT04070G
_journal_year                    2022
_chemical_formula_moiety         'C20 H17 F2 N7 O4 Zn, 2(H2 O)'
_chemical_formula_sum            'C20 H21 F2 N7 O6 Zn'
_chemical_formula_weight         558.81
_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             2021-11-01
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-11-26 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                105.715(4)
_cell_angle_beta                 95.658(4)
_cell_angle_gamma                110.128(4)
_cell_formula_units_Z            2
_cell_length_a                   9.5983(4)
_cell_length_b                   11.3429(6)
_cell_length_c                   12.5297(6)
_cell_measurement_reflns_used    2590
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.6730
_cell_measurement_theta_min      3.3730
_cell_volume                     1204.87(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0667
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  17.00   1.00    4.61    --  -19.31 -99.00 120.00   41
  2  ω     -9.00  89.00   1.00    4.61    --   17.28  37.00 120.00   98
  3  ω     -4.00  86.00   1.00    4.61    --   17.28  57.00 -30.00   90
  4  ω    -52.00  39.00   1.00    4.61    --   17.28 -57.00-180.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0208207000
_diffrn_orient_matrix_UB_12      -0.0695630000
_diffrn_orient_matrix_UB_13      -0.0234076000
_diffrn_orient_matrix_UB_21      -0.0195864000
_diffrn_orient_matrix_UB_22      0.0030723000
_diffrn_orient_matrix_UB_23      -0.0549809000
_diffrn_orient_matrix_UB_31      0.0752962000
_diffrn_orient_matrix_UB_32      0.0107361000
_diffrn_orient_matrix_UB_33      -0.0071149000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7161
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_min         3.065
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.085
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.179
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0430
_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)+(0.0337P)²+0.4508P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0939
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3605
_reflns_number_total             4536
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt04070g2.cif
_cod_data_source_block           Compound_IV
_cod_database_code               7709632
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H20 F2 N7 O6 Zn'
_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.
;
_reflns_odcompleteness_completeness 99.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N5(H5), N7(H7), C1(H1), C2(H2A), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C18(H18)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.080
_oxdiff_exptl_absorpt_empirical_full_min 0.966
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
Zn1 Zn 0.27760(4) 0.19206(3) 0.28594(3) 0.03737(12) Uani 1 1 d . . . . .
F1 F 0.1883(3) 0.5326(2) 0.65337(18) 0.0868(8) Uani 1 1 d . . . . .
F2 F 0.4943(3) 0.6623(2) 0.2199(2) 0.1015(9) Uani 1 1 d . . . . .
O1 O 0.3056(3) 0.4779(2) 0.2973(2) 0.0585(6) Uani 1 1 d . . . . .
O2 O 0.4922(2) 0.1760(2) 0.12291(19) 0.0517(6) Uani 1 1 d . . . . .
O3 O 0.1174(2) 0.0445(2) 0.41104(18) 0.0482(6) Uani 1 1 d . . . . .
O4 O 0.0366(3) 0.3130(2) 0.7172(2) 0.0646(7) Uani 1 1 d . . . . .
N1 N 0.0479(3) 0.1252(3) 0.1960(2) 0.0449(6) Uani 1 1 d . . . . .
N2 N 0.2329(3) -0.0059(3) 0.1808(3) 0.0564(8) Uani 1 1 d . . . . .
H2 H 0.276(8) 0.019(7) 0.121(6) 0.23(4) Uiso 1 1 d . . . . .
N3 N 0.4546(3) 0.1504(2) 0.3660(2) 0.0424(6) Uani 1 1 d . . . . .
N4 N 0.4003(3) 0.3257(2) 0.2160(2) 0.0384(6) Uani 1 1 d . . . . .
N5 N 0.5849(3) 0.3806(3) 0.1081(2) 0.0512(7) Uani 1 1 d . . . . .
H5 H 0.643064 0.358592 0.065564 0.061 Uiso 1 1 calc R U . . .
N6 N 0.2197(3) 0.2642(2) 0.4377(2) 0.0416(6) Uani 1 1 d . . . . .
N7 N 0.0860(3) 0.1837(2) 0.5659(2) 0.0425(6) Uani 1 1 d . . . . .
H7 H 0.041417 0.116012 0.586321 0.051 Uiso 1 1 calc R U . . .
C1 C 0.5654(4) 0.2364(4) 0.4549(3) 0.0579(9) Uani 1 1 d . . . . .
H1 H 0.564226 0.319742 0.488605 0.069 Uiso 1 1 calc R U . . .
C2 C 0.6802(4) 0.2065(4) 0.4980(4) 0.0761(12) Uani 1 1 d . . . . .
H2A H 0.755798 0.268472 0.559821 0.091 Uiso 1 1 calc R U . . .
C3 C 0.6823(4) 0.0852(5) 0.4493(4) 0.0770(12) Uani 1 1 d . . . . .
H3 H 0.760209 0.063194 0.476993 0.092 Uiso 1 1 calc R U . . .
C4 C 0.5689(4) -0.0047(4) 0.3591(3) 0.0644(10) Uani 1 1 d . . . . .
H4 H 0.568138 -0.088772 0.325244 0.077 Uiso 1 1 calc R U . . .
C5 C 0.4557(3) 0.0308(3) 0.3192(3) 0.0424(7) Uani 1 1 d . . . . .
C6 C 0.3228(4) -0.0668(3) 0.2260(3) 0.0589(9) Uani 1 1 d . . . . .
H6A H 0.359677 -0.112604 0.165171 0.071 Uiso 1 1 calc R U . . .
H6B H 0.258867 -0.132647 0.254970 0.071 Uiso 1 1 calc R U . . .
C7 C 0.0757(3) -0.0851(3) 0.1316(3) 0.0494(8) Uani 1 1 d . . . . .
H7A H 0.038795 -0.150558 0.169283 0.059 Uiso 1 1 calc R U . . .
H7B H 0.064936 -0.132388 0.052189 0.059 Uiso 1 1 calc R U . . .
C8 C -0.0199(3) -0.0033(3) 0.1410(2) 0.0442(8) Uani 1 1 d . . . . .
C9 C -0.1754(4) -0.0616(4) 0.0966(3) 0.0630(11) Uani 1 1 d . . . . .
H9 H -0.222217 -0.152095 0.056880 0.076 Uiso 1 1 calc R U . . .
C10 C -0.2591(4) 0.0167(5) 0.1125(3) 0.0750(13) Uani 1 1 d . . . . .
H10 H -0.363364 -0.020523 0.083616 0.090 Uiso 1 1 calc R U . . .
C11 C -0.1878(4) 0.1488(5) 0.1706(3) 0.0720(12) Uani 1 1 d . . . . .
H11 H -0.242571 0.202995 0.183004 0.086 Uiso 1 1 calc R U . . .
C12 C -0.0346(4) 0.2003(4) 0.2105(3) 0.0583(9) Uani 1 1 d . . . . .
H12 H 0.014472 0.290898 0.249291 0.070 Uiso 1 1 calc R U . . .
C13 C 0.1414(3) 0.1600(3) 0.4687(2) 0.0386(7) Uani 1 1 d . . . . .
C14 C 0.2319(4) 0.3862(3) 0.5008(3) 0.0504(8) Uani 1 1 d . . . . .
H14 H 0.283037 0.458266 0.478325 0.060 Uiso 1 1 calc R U . . .
C15 C 0.1743(4) 0.4089(3) 0.5941(3) 0.0522(9) Uani 1 1 d . . . . .
C16 C 0.0949(4) 0.3041(3) 0.6334(3) 0.0451(8) Uani 1 1 d . . . . .
C17 C 0.4919(3) 0.2879(3) 0.1486(2) 0.0402(7) Uani 1 1 d . . . . .
C18 C 0.5877(4) 0.5058(4) 0.1333(3) 0.0591(10) Uani 1 1 d . . . . .
H18 H 0.654557 0.567443 0.107152 0.071 Uiso 1 1 calc R U . . .
C19 C 0.4955(4) 0.5394(3) 0.1948(3) 0.0589(10) Uani 1 1 d . . . . .
C20 C 0.3942(4) 0.4478(3) 0.2393(3) 0.0450(8) Uani 1 1 d . . . . .
O1W O -0.0915(3) 0.4717(3) 0.8321(2) 0.0698(7) Uani 1 1 d G . . . .
H1WA H -0.165859 0.467657 0.786412 0.105 Uiso 1 1 d G U . . .
H1WB H -0.046221 0.426384 0.796168 0.105 Uiso 1 1 d G U . . .
O2W O 0.8203(3) 0.3588(3) 0.0007(2) 0.0732(8) Uani 1 1 d G . . . .
H2WA H 0.842297 0.399938 -0.046653 0.110 Uiso 1 1 d G U . . .
H2WB H 0.898787 0.395893 0.054249 0.110 Uiso 1 1 d G U . . .
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 2 -17 0.0727
7 6 6 0.0982
11 -12 7 0.1300
-1 15 -3 0.1194
4 12 -9 0.1206
0 13 2 0.1208
-6 15 -9 0.1428
1 -11 16 0.1213
2 3 14 0.0807
3 13 -4 0.1195
13 -10 -3 0.1460
2 -15 3 0.1574
11 -4 8 0.1055
2 -3 -16 0.0775
-13 2 5 0.1115
0 -3 17 0.0960
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
N2 Zn1 N1 77.06(10) . . ?
N2 Zn1 N3 77.94(10) . . ?
N3 Zn1 N1 149.60(10) . . ?
N4 Zn1 N1 104.29(10) . . ?
N4 Zn1 N2 110.09(12) . . ?
N4 Zn1 N3 100.33(9) . . ?
N4 Zn1 N6 118.02(10) . . ?
N6 Zn1 N1 90.92(10) . . ?
N6 Zn1 N2 131.89(11) . . ?
N6 Zn1 N3 93.05(10) . . ?
C8 N1 Zn1 115.8(2) . . ?
C8 N1 C12 119.5(3) . . ?
C12 N1 Zn1 123.4(2) . . ?
Zn1 N2 H2 96(4) . . ?
C6 N2 Zn1 113.6(2) . . ?
C6 N2 H2 107(4) . . ?
C7 N2 Zn1 114.3(2) . . ?
C7 N2 H2 105(4) . . ?
C7 N2 C6 117.9(3) . . ?
C1 N3 Zn1 125.2(2) . . ?
C5 N3 Zn1 116.2(2) . . ?
C5 N3 C1 118.5(3) . . ?
C17 N4 Zn1 116.8(2) . . ?
C20 N4 Zn1 120.70(19) . . ?
C20 N4 C17 122.4(3) . . ?
C17 N5 H5 119.0 . . ?
C18 N5 H5 119.0 . . ?
C18 N5 C17 121.9(3) . . ?
C13 N6 Zn1 107.99(19) . . ?
C13 N6 C14 117.9(3) . . ?
C14 N6 Zn1 133.8(2) . . ?
C13 N7 H7 116.8 . . ?
C16 N7 H7 116.8 . . ?
C16 N7 C13 126.4(3) . . ?
N3 C1 H1 118.8 . . ?
N3 C1 C2 122.5(4) . . ?
C2 C1 H1 118.8 . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 H2A 120.5 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.3(4) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.2(4) . . ?
C5 C4 H4 120.4 . . ?
N3 C5 C4 121.5(3) . . ?
N3 C5 C6 117.0(3) . . ?
C4 C5 C6 121.4(3) . . ?
N2 C6 C5 113.1(3) . . ?
N2 C6 H6A 109.0 . . ?
N2 C6 H6B 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
N2 C7 H7A 109.1 . . ?
N2 C7 H7B 109.1 . . ?
N2 C7 C8 112.4(3) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
N1 C8 C7 117.8(3) . . ?
N1 C8 C9 120.9(3) . . ?
C9 C8 C7 121.2(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.0(4) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.3(4) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.8(4) . . ?
C12 C11 H11 120.6 . . ?
N1 C12 C11 122.4(4) . . ?
N1 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
O3 C13 N6 121.5(3) . . ?
O3 C13 N7 120.0(3) . . ?
N6 C13 N7 118.5(3) . . ?
N6 C14 H14 118.2 . . ?
C15 C14 N6 123.6(3) . . ?
C15 C14 H14 118.2 . . ?
F1 C15 C16 117.4(3) . . ?
C14 C15 F1 121.2(3) . . ?
C14 C15 C16 121.4(3) . . ?
O4 C16 N7 120.8(3) . . ?
O4 C16 C15 127.1(3) . . ?
N7 C16 C15 112.1(3) . . ?
O2 C17 N4 122.6(3) . . ?
O2 C17 N5 119.7(3) . . ?
N4 C17 N5 117.7(3) . . ?
N5 C18 H18 120.1 . . ?
C19 C18 N5 119.7(3) . . ?
C19 C18 H18 120.1 . . ?
F2 C19 C20 117.4(3) . . ?
C18 C19 F2 121.1(3) . . ?
C18 C19 C20 121.5(3) . . ?
O1 C20 N4 121.2(3) . . ?
O1 C20 C19 122.2(3) . . ?
N4 C20 C19 116.6(3) . . ?
H1WA O1W H1WB 109.5 . . ?
H2WA O2W H2WB 104.5 . . ?
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
Zn1 N1 2.146(3) . ?
Zn1 N2 2.141(3) . ?
Zn1 N3 2.142(3) . ?
Zn1 N4 2.037(2) . ?
Zn1 N6 2.068(2) . ?
F1 C15 1.351(4) . ?
F2 C19 1.348(4) . ?
O1 C20 1.247(3) . ?
O2 C17 1.223(4) . ?
O3 C13 1.241(3) . ?
O4 C16 1.234(3) . ?
N1 C8 1.317(4) . ?
N1 C12 1.340(4) . ?
N2 H2 0.95(6) . ?
N2 C6 1.439(4) . ?
N2 C7 1.431(4) . ?
N3 C1 1.337(4) . ?
N3 C5 1.328(4) . ?
N4 C17 1.371(4) . ?
N4 C20 1.358(4) . ?
N5 H5 0.8600 . ?
N5 C17 1.375(4) . ?
N5 C18 1.359(4) . ?
N6 C13 1.344(4) . ?
N6 C14 1.353(4) . ?
N7 H7 0.8600 . ?
N7 C13 1.374(4) . ?
N7 C16 1.368(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.363(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.354(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(4) . ?
C5 C6 1.500(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.505(4) . ?
C8 C9 1.390(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.360(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.364(5) . ?
C12 H12 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.342(4) . ?
C15 C16 1.415(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.316(5) . ?
C19 C20 1.436(4) . ?
O1W H1WA 0.8496 . ?
O1W H1WB 0.8501 . ?
O2W H2WA 0.8499 . ?
O2W H2WB 0.8505 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5 O2W 0.86 1.96 2.789(4) 162.8 . yes
N7 H7 O3 0.86 1.94 2.763(3) 159.1 2_556 yes
O1W H1WA O1 0.85 1.98 2.798(4) 161.2 2_566 yes
O1W H1WB O4 0.85 1.85 2.700(3) 174.4 . yes
O2W H2WA O1W 0.85 1.97 2.809(4) 169.7 1_654 yes
O2W H2WB O1W 0.85 2.03 2.857(4) 164.2 2_666 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 N1 C8 C7 -9.3(3) . . . . ?
Zn1 N1 C8 C9 168.6(2) . . . . ?
Zn1 N1 C12 C11 -166.6(3) . . . . ?
Zn1 N2 C6 C5 -15.3(4) . . . . ?
Zn1 N2 C7 C8 14.0(4) . . . . ?
Zn1 N3 C1 C2 -176.0(3) . . . . ?
Zn1 N3 C5 C4 176.3(2) . . . . ?
Zn1 N3 C5 C6 -7.8(4) . . . . ?
Zn1 N4 C17 O2 5.9(4) . . . . ?
Zn1 N4 C17 N5 -174.8(2) . . . . ?
Zn1 N4 C20 O1 -5.2(4) . . . . ?
Zn1 N4 C20 C19 174.3(2) . . . . ?
Zn1 N6 C13 O3 1.4(4) . . . . ?
Zn1 N6 C13 N7 -177.8(2) . . . . ?
Zn1 N6 C14 C15 174.3(3) . . . . ?
F1 C15 C16 O4 -0.4(6) . . . . ?
F1 C15 C16 N7 179.1(3) . . . . ?
F2 C19 C20 O1 1.4(5) . . . . ?
F2 C19 C20 N4 -178.0(3) . . . . ?
N1 C8 C9 C10 -1.1(5) . . . . ?
N2 C7 C8 N1 -3.2(4) . . . . ?
N2 C7 C8 C9 179.0(3) . . . . ?
N3 C1 C2 C3 -0.1(6) . . . . ?
N3 C5 C6 N2 15.4(4) . . . . ?
N5 C18 C19 F2 -179.2(3) . . . . ?
N5 C18 C19 C20 1.9(6) . . . . ?
N6 C14 C15 F1 -179.2(3) . . . . ?
N6 C14 C15 C16 -0.1(6) . . . . ?
C1 N3 C5 C4 -1.0(5) . . . . ?
C1 N3 C5 C6 175.0(3) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 N3 0.2(5) . . . . ?
C3 C4 C5 C6 -175.6(3) . . . . ?
C4 C5 C6 N2 -168.6(3) . . . . ?
C5 N3 C1 C2 0.9(5) . . . . ?
C6 N2 C7 C8 151.4(3) . . . . ?
C7 N2 C6 C5 -153.1(3) . . . . ?
C7 C8 C9 C10 176.8(3) . . . . ?
C8 N1 C12 C11 0.2(5) . . . . ?
C8 C9 C10 C11 0.2(6) . . . . ?
C9 C10 C11 C12 0.8(6) . . . . ?
C10 C11 C12 N1 -1.0(6) . . . . ?
C12 N1 C8 C7 -177.0(3) . . . . ?
C12 N1 C8 C9 0.9(5) . . . . ?
C13 N6 C14 C15 2.1(5) . . . . ?
C13 N7 C16 O4 177.7(3) . . . . ?
C13 N7 C16 C15 -1.8(5) . . . . ?
C14 N6 C13 O3 175.5(3) . . . . ?
C14 N6 C13 N7 -3.7(4) . . . . ?
C14 C15 C16 O4 -179.5(3) . . . . ?
C14 C15 C16 N7 -0.1(5) . . . . ?
C16 N7 C13 O3 -175.4(3) . . . . ?
C16 N7 C13 N6 3.8(5) . . . . ?
C17 N4 C20 O1 177.2(3) . . . . ?
C17 N4 C20 C19 -3.4(4) . . . . ?
C17 N5 C18 C19 -2.5(5) . . . . ?
C18 N5 C17 O2 179.4(3) . . . . ?
C18 N5 C17 N4 0.1(5) . . . . ?
C18 C19 C20 O1 -179.6(4) . . . . ?
C18 C19 C20 N4 0.9(5) . . . . ?
C20 N4 C17 O2 -176.3(3) . . . . ?
C20 N4 C17 N5 2.9(4) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.2010 2.2665 -17.4751 0.2264 0.9442 0.2391
7.2176 5.5514 6.2878 -0.6836 -0.4700 0.5583
11.0758 -11.6589 6.6406 0.4250 -0.6179 0.6615
-0.5596 15.0671 -3.1564 -0.9626 0.2308 0.1421
4.1511 12.3295 -8.9666 -0.7342 0.4496 0.5087
0.2057 13.4144 2.0929 -0.9864 -0.0779 0.1446
-5.8114 15.0769 -9.3258 -0.7095 0.6729 -0.2094
0.7665 -10.9259 15.6706 0.3773 -0.9102 -0.1711
2.0451 3.4431 13.8347 -0.6059 -0.7901 0.0925
3.4883 13.0148 -4.3388 -0.8764 0.2102 0.4333
12.6675 -9.6501 -2.9731 0.4771 -0.1143 0.8714
1.9227 -15.4484 2.6896 0.9716 -0.2330 -0.0402
10.8741 -3.6811 8.1738 -0.1617 -0.6737 0.7211
2.0628 -2.5437 -15.9288 0.5069 0.8276 0.2413
-13.1670 2.3311 4.7208 0.0015 0.0055 -1.0000
0.3061 -2.5848 17.2885 -0.2313 -0.9645 -0.1277
