#------------------------------------------------------------------------------
#$Date: 2016-12-06 02:19:15 +0200 (Tue, 06 Dec 2016) $
#$Revision: 188931 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/80/2108004.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_2108004
loop_
_publ_author_name
'Perdih, Franc'
_publ_section_title
;
 CuII and ZnII β-diketonate coordination polymers based on
 pyrimidin-2-amine, pyrazine and 1,2-bis(4-pyridyl)ethane
;
_journal_coeditor_code           EB5048
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              828
_journal_page_last               835
_journal_paper_doi               10.1107/S2052520616014566
_journal_volume                  72
_journal_year                    2016
_chemical_formula_moiety         'C24 H17 F6 N3 O4 Zn'
_chemical_formula_sum            'C24 H17 F6 N3 O4 Zn'
_chemical_formula_weight         590.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 115.198(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5334(4)
_cell_length_b                   9.2949(2)
_cell_length_c                   13.0287(5)
_cell_measurement_reflns_used    5290
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3455
_cell_measurement_theta_min      2.7850
_cell_volume                     1263.79(9)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_molecular_graphics    'Mercury (Macrae, 2006)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4933
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12548
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.791
_exptl_absorpt_coefficient_mu    1.052
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis Pro; Oxford Diffraction, 2013'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_description       plate
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.236
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0344
_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)+(0.0386P)²+0.3634P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0893
_reflns_number_gt                2260
_reflns_number_total             2861
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            eb5048sup1.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 2108003--2108008.cif.'
_cod_original_cell_volume        1263.79(8)
_cod_database_code               2108004
_cod_database_fobs_code          2108004
_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_min   0.621
_shelx_estimated_absorpt_t_max   0.969
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn Zn1 0.5000 0.5000 0.0000 0.04178(12) Uani d 1 . .
O O1 0.49666(12) 0.31644(14) 0.08326(11) 0.0436(3) Uani d 1 . .
O O2 0.35739(13) 0.58194(15) 0.03574(12) 0.0469(3) Uani d 1 . .
N N1 0.65295(15) 0.60274(17) 0.16441(13) 0.0413(4) Uani d 1 . .
N N2 0.7500 0.3916(3) 0.2500 0.0606(7) Uani d 1 . .
H H2A 0.6896 0.3453 0.1968 0.091 Uiso calc 0.5 . .
H H2B 0.8104 0.3453 0.3032 0.091 Uiso calc 0.5 . .
F F1A 0.3481(12) 0.1068(12) 0.2110(12) 0.140(4) Uani d 0.66(2) A 1
F F2A 0.3965(15) 0.0435(7) 0.0767(10) 0.153(4) Uani d 0.66(2) A 1
F F3A 0.5387(7) 0.1054(9) 0.2357(10) 0.122(3) Uani d 0.66(2) A 1
F F1B 0.317(2) 0.0900(19) 0.164(3) 0.157(8) Uani d 0.34(2) A 2
F F2B 0.447(3) 0.0395(15) 0.107(2) 0.156(9) Uani d 0.34(2) A 2
F F3B 0.508(4) 0.141(3) 0.265(2) 0.209(12) Uani d 0.34(2) A 2
C C1 0.4208(3) 0.1358(3) 0.1609(3) 0.0815(9) Uani d 1 . .
C C2 0.4083(2) 0.2881(2) 0.11364(17) 0.0452(5) Uani d 1 . .
C C3 0.3097(2) 0.3717(2) 0.1105(2) 0.0540(5) Uani d 1 . .
H H3 0.2508 0.3300 0.1328 0.065 Uiso calc 1 . .
C C4 0.29043(18) 0.5176(2) 0.07562(17) 0.0433(5) Uani d 1 . .
C C5 0.18948(19) 0.6052(3) 0.09068(18) 0.0514(5) Uani d 1 . .
C C6 0.1013(2) 0.5462(3) 0.1249(2) 0.0630(6) Uani d 1 . .
H H6 0.1020 0.4478 0.1382 0.076 Uiso calc 1 . .
C C7 0.0118(2) 0.6339(4) 0.1395(2) 0.0819(9) Uani d 1 . .
H H7 -0.0477 0.5936 0.1617 0.098 Uiso calc 1 . .
C C8 0.0106(3) 0.7770(5) 0.1216(3) 0.1039(12) Uani d 1 . .
H H8 -0.0501 0.8348 0.1310 0.125 Uiso calc 1 . .
C C9 0.0979(4) 0.8368(4) 0.0899(4) 0.1191(14) Uani d 1 . .
H H9 0.0981 0.9357 0.0794 0.143 Uiso calc 1 . .
C C10 0.1867(3) 0.7506(3) 0.0733(3) 0.0873(9) Uani d 1 . .
H H10 0.2449 0.7922 0.0500 0.105 Uiso calc 1 . .
C C11 0.7500 0.5343(3) 0.2500 0.0396(6) Uani d 1 . .
C C12 0.6541(2) 0.7458(2) 0.16808(18) 0.0512(5) Uani d 1 . .
H H12 0.5866 0.7956 0.1124 0.061 Uiso calc 1 . .
C C13 0.7500 0.8233(3) 0.2500 0.0586(8) Uani d 1 . .
H H13 0.7500 0.9233 0.2500 0.070 Uiso calc 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'
Zn Zn 0.2839 1.4301 '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'
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
O1 Zn1 O1 . 3_665 180.0
O1 Zn1 O2 . . 89.49(5)
O1 Zn1 O2 3_665 . 90.50(5)
O1 Zn1 O2 . 3_665 90.51(5)
O1 Zn1 O2 3_665 3_665 89.50(5)
O2 Zn1 O2 . 3_665 180.0
O1 Zn1 N1 . 3_665 88.14(5)
O1 Zn1 N1 3_665 3_665 91.86(5)
O2 Zn1 N1 . 3_665 89.68(6)
O2 Zn1 N1 3_665 3_665 90.32(6)
O1 Zn1 N1 . . 91.86(5)
O1 Zn1 N1 3_665 . 88.14(5)
O2 Zn1 N1 . . 90.32(6)
O2 Zn1 N1 3_665 . 89.68(6)
N1 Zn1 N1 3_665 . 180.00(7)
C2 O1 Zn1 . . 122.81(13)
C4 O2 Zn1 . . 128.11(13)
C12 N1 C11 . . 116.57(18)
C12 N1 Zn1 . . 115.85(13)
C11 N1 Zn1 . . 127.06(14)
C11 N2 H2A . . 120.0
C11 N2 H2B . . 120.0
H2A N2 H2B . . 120.0
F2B C1 F1B . . 103.3(13)
F2B C1 F3B . . 110.3(15)
F1B C1 F3B . . 107.4(14)
F1A C1 F3A . . 105.5(7)
F1A C1 F2A . . 109.2(7)
F3A C1 F2A . . 105.1(6)
F2B C1 C2 . . 116.4(8)
F1B C1 C2 . . 112.8(10)
F1A C1 C2 . . 115.3(5)
F3B C1 C2 . . 106.5(9)
F3A C1 C2 . . 112.8(4)
F2A C1 C2 . . 108.5(5)
O1 C2 C3 . . 129.99(19)
O1 C2 C1 . . 111.6(2)
C3 C2 C1 . . 118.4(2)
C2 C3 C4 . . 124.76(19)
C2 C3 H3 . . 117.6
C4 C3 H3 . . 117.6
O2 C4 C3 . . 123.37(19)
O2 C4 C5 . . 116.46(18)
C3 C4 C5 . . 120.11(19)
C10 C5 C6 . . 118.4(2)
C10 C5 C4 . . 118.6(2)
C6 C5 C4 . . 123.0(2)
C5 C6 C7 . . 120.1(3)
C5 C6 H6 . . 120.0
C7 C6 H6 . . 120.0
C8 C7 C6 . . 120.6(3)
C8 C7 H7 . . 119.7
C6 C7 H7 . . 119.7
C7 C8 C9 . . 120.0(3)
C7 C8 H8 . . 120.0
C9 C8 H8 . . 120.0
C8 C9 C10 . . 120.2(3)
C8 C9 H9 . . 119.9
C10 C9 H9 . . 119.9
C5 C10 C9 . . 120.7(3)
C5 C10 H10 . . 119.6
C9 C10 H10 . . 119.6
N2 C11 N1 . . 117.98(12)
N2 C11 N1 . 2_655 117.97(12)
N1 C11 N1 . 2_655 124.0(2)
N1 C12 C13 . . 123.1(2)
N1 C12 H12 . . 118.5
C13 C12 H12 . . 118.5
C12 C13 C12 . 2_655 116.6(3)
C12 C13 H13 . . 121.7
C12 C13 H13 2_655 . 121.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Zn1 O1 . 2.0310(13)
Zn1 O1 3_665 2.0310(13)
Zn1 O2 . 2.0382(13)
Zn1 O2 3_665 2.0382(13)
Zn1 N1 3_665 2.3226(16)
Zn1 N1 . 2.3226(16)
O1 C2 . 1.268(2)
O2 C4 . 1.251(2)
N1 C12 . 1.331(3)
N1 C11 . 1.356(2)
N2 C11 . 1.327(4)
N2 H2A . 0.8600
N2 H2B . 0.8600
F1A C1 . 1.292(8)
F2A C1 . 1.325(9)
F3A C1 . 1.322(9)
F1B C1 . 1.290(16)
F2B C1 . 1.249(16)
F3B C1 . 1.30(2)
C1 C2 . 1.526(3)
C2 C3 . 1.364(3)
C3 C4 . 1.417(3)
C3 H3 . 0.9300
C4 C5 . 1.500(3)
C5 C10 . 1.369(4)
C5 C6 . 1.386(3)
C6 C7 . 1.390(4)
C6 H6 . 0.9300
C7 C8 . 1.349(5)
C7 H7 . 0.9300
C8 C9 . 1.359(5)
C8 H8 . 0.9300
C9 C10 . 1.388(4)
C9 H9 . 0.9300
C10 H10 . 0.9300
C11 N1 2_655 1.356(2)
C12 C13 . 1.370(3)
C12 H12 . 0.9300
C13 C12 2_655 1.370(3)
C13 H13 . 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
N2 H2B O1 2_655 0.86 2.10 2.8878(14) 152.0
N2 H2A O1 . 0.86 2.10 2.8878(14) 152.0
C10 H10 O2 . 0.93 2.40 2.719(4) 100
C12 H12 O1 3_665 0.93 2.53 3.039(3) 114
C3 H3 F1A . 0.93 2.37 2.735(12) 103
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_4
_geom_torsion
Zn1 O1 C2 C3 . -7.7(3)
Zn1 O1 C2 C1 . 172.83(19)
F2B C1 C2 O1 . -43.3(16)
F1B C1 C2 O1 . -162.3(16)
F1A C1 C2 O1 . 168.9(9)
F3B C1 C2 O1 . 80(2)
F3A C1 C2 O1 . 47.6(7)
F2A C1 C2 O1 . -68.4(8)
F2B C1 C2 C3 . 137.2(16)
F1B C1 C2 C3 . 18.1(16)
F1A C1 C2 C3 . -10.7(9)
F3B C1 C2 C3 . -99(2)
F3A C1 C2 C3 . -131.9(6)
F2A C1 C2 C3 . 112.1(7)
O1 C2 C3 C4 . -3.5(4)
C1 C2 C3 C4 . 175.9(2)
Zn1 O2 C4 C3 . 4.2(3)
Zn1 O2 C4 C5 . -178.58(12)
C2 C3 C4 O2 . 5.6(4)
C2 C3 C4 C5 . -171.5(2)
O2 C4 C5 C10 . -7.6(3)
C3 C4 C5 C10 . 169.7(2)
O2 C4 C5 C6 . 174.50(19)
C3 C4 C5 C6 . -8.2(3)
C10 C5 C6 C7 . 0.8(4)
C4 C5 C6 C7 . 178.7(2)
C5 C6 C7 C8 . -0.7(4)
C6 C7 C8 C9 . -0.5(5)
C7 C8 C9 C10 . 1.5(6)
C6 C5 C10 C9 . 0.2(5)
C4 C5 C10 C9 . -177.8(3)
C8 C9 C10 C5 . -1.4(6)
C12 N1 C11 N2 . 178.58(13)
Zn1 N1 C11 N2 . -10.11(13)
C12 N1 C11 N1 2_655 -1.42(13)
Zn1 N1 C11 N1 2_655 169.89(13)
C11 N1 C12 C13 . 2.9(3)
Zn1 N1 C12 C13 . -169.37(13)
N1 C12 C13 C12 2_655 -1.56(14)
