#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:24:26 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179629 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/93/4509354.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4509354
loop_
_publ_author_name
'Hunger, Jens'
'Krautscheid, Harald'
'Sieler, Joachim'
_publ_section_title
;
 Hydrothermal Synthesis and Structure of Coordination Polymers by
 Combination of Bipyrazole and Aromatic Dicarboxylate Ligands
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4613
_journal_paper_doi               10.1021/cg801282r
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         'C13 H11 N2 O4 Zn'
_chemical_formula_sum            'C13 H11 N2 O4 Zn'
_chemical_formula_weight         324.61
_chemical_name_systematic
;
catena-(bis(μ₄-benzene-1,4-dicarboxylato)-(μ₂-3,3',5,5'-tetramethyl-
4,4'-bipyrazole)-di-zinc(ii))
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 108.035(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.1713(12)
_cell_length_b                   16.6592(14)
_cell_length_c                   12.4549(9)
_cell_measurement_reflns_used    7935
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      7.50
_cell_volume                     2795.9(4)
_computing_cell_refinement       'RECIPE (Stoe & Cie, 2002)'
_computing_data_collection       'EXPOSE (Stoe & Cie, 2002)'
_computing_data_reduction        'INTEGRATE (Stoe & Cie, 2002)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL97 and DIAMOND'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Stoe IPDS-I'
_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  0.0696
_diffrn_reflns_av_sigmaI/netI    0.0899
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            48754
_diffrn_reflns_theta_full        27.91
_diffrn_reflns_theta_max         27.91
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    1.770
_exptl_absorpt_correction_T_max  0.7354
_exptl_absorpt_correction_T_min  0.6410
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
[X-RED32 (Stoe & Cie, 2001);
crystal description using FACEIT (Stoe & Cie, 2002);
optimization using equivalent reflections
(X-SHAPE; Stoe & Cie, 1999)]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3346
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      0.682
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0244
_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)+(0.0213P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0490
_refine_ls_wR_factor_ref         0.0497
_reflns_number_gt                1991
_reflns_number_total             3346
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg801282rsup1.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4509354
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.47632(17) 0.24119(14) 0.29549(18) 0.0190(5) Uani 1 1 d D . .
C6 C 0.37123(18) 0.31073(18) 0.7323(2) 0.0281(6) Uani 1 1 d . . .
C7 C 0.3076(2) 0.38159(16) 0.7409(2) 0.0311(7) Uani 1 1 d . . .
C8 C 0.3170(3) 0.4158(2) 0.8452(3) 0.0494(10) Uani 1 1 d . . .
C9 C 0.2576(3) 0.4807(2) 0.8527(3) 0.0541(11) Uani 1 1 d . . .
C10 C 0.1889(2) 0.51186(16) 0.7574(3) 0.0339(7) Uani 1 1 d . . .
C11 C 0.6253(2) 0.08312(16) 0.7645(2) 0.0321(7) Uani 1 1 d . . .
C12 C 0.1794(2) 0.47737(16) 0.6535(3) 0.0304(7) Uani 1 1 d . . .
C13 C 0.2391(2) 0.41304(17) 0.6450(3) 0.0304(7) Uani 1 1 d . . .
N1 N 0.44659(13) 0.21629(11) 0.45867(15) 0.0225(5) Uani 1 1 d D . .
O1 O 0.57106(14) 0.28318(10) 0.67847(15) 0.0355(5) Uani 1 1 d . . .
O2 O 0.36045(13) 0.28284(10) 0.63435(15) 0.0328(5) Uani 1 1 d . . .
O3 O 0.56672(15) 0.10906(11) 0.67458(16) 0.0374(5) Uani 1 1 d . . .
O4 O 0.36272(15) 0.11247(12) 0.63830(18) 0.0413(5) Uani 1 1 d . . .
Zn1 Zn 0.461577(19) 0.197617(17) 0.62370(2) 0.01541(7) Uani 1 1 d . . .
C1A C 0.4018(8) 0.2893(6) 0.3077(8) 0.028(2) Uani 0.539(9) 1 d PD A 1
C4A C 0.3467(7) 0.3530(6) 0.2305(7) 0.065(3) Uani 0.539(9) 1 d PD A 1
H4A1 H 0.271 0.3380 0.201 0.097 Uiso 0.539(9) 1 calc PR A 1
H4A2 H 0.375 0.358 0.162 0.097 Uiso 0.539(9) 1 calc PR A 1
H4A3 H 0.355 0.408 0.274 0.097 Uiso 0.539(9) 1 calc PR A 1
C5A C 0.5785(5) 0.1270(5) 0.4242(5) 0.0384(19) Uani 0.539(9) 1 d PD A 1
H5A1 H 0.614 0.1319 0.494 0.058 Uiso 0.539(9) 1 calc PR A 1
H5A2 H 0.616 0.1308 0.382 0.058 Uiso 0.539(9) 1 calc PR A 1
H5A3 H 0.5497 0.081 0.414 0.058 Uiso 0.539(9) 1 calc PR A 1
N2A N 0.3858(10) 0.2730(7) 0.4024(12) 0.0244(19) Uani 0.539(9) 1 d PD A 1
H2A H 0.347 0.2933 0.4229 0.029 Uiso 0.539(9) 1 calc PR A 1
C3A C 0.5026(4) 0.1915(4) 0.3946(4) 0.0166(13) Uiso 0.539(9) 1 d PD A 1
C1B C 0.3791(9) 0.2676(7) 0.2783(8) 0.021(2) Uani 0.461(9) 1 d PD A 2
N2B N 0.3658(11) 0.2528(7) 0.3837(14) 0.0192(19) Uani 0.461(9) 1 d PD A 2
H2B H 0.321 0.2633 0.3973 0.023 Uiso 0.461(9) 1 calc PR A 2
C3B C 0.5146(4) 0.2158(4) 0.4031(5) 0.0142(15) Uiso 0.461(9) 1 d PD A 2
C5B C 0.6146(5) 0.1825(6) 0.4579(5) 0.037(2) Uani 0.461(9) 1 d PD A 2
H5B1 H 0.648 0.186 0.414 0.056 Uiso 0.461(9) 1 calc PR A 2
H5B2 H 0.6097 0.135 0.474 0.056 Uiso 0.461(9) 1 calc PR A 2
H5B3 H 0.642 0.208 0.516 0.056 Uiso 0.461(9) 1 calc PR A 2
C4B C 0.3012(5) 0.3012(6) 0.1805(6) 0.041(2) Uani 0.461(9) 1 d PD A 2
H4B1 H 0.245 0.285 0.181 0.061 Uiso 0.461(9) 1 calc PR A 2
H4B2 H 0.311 0.286 0.120 0.061 Uiso 0.461(9) 1 calc PR A 2
H4B3 H 0.303 0.352 0.184 0.061 Uiso 0.461(9) 1 calc PR A 2
H8 H 0.359 0.3962 0.912 0.057 Uiso 1 1 calc R . .
H9 H 0.269 0.5079 0.923 0.062 Uiso 1 1 calc R . .
H12 H 0.130 0.4953 0.589 0.035 Uiso 1 1 calc R . .
H13 H 0.2328 0.3914 0.578 0.034 Uiso 1 1 calc R . .
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'
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
C3B C2 C1A 99.2(5) . .
C3B C2 C1B 109.0(5) . .
C1A C2 C3A 104.2(5) . .
C1B C2 C3A 107.1(5) . .
C3B C2 C2 128.3(3) . 2_655
C1A C2 C2 129.1(5) . 2_655
C1B C2 C2 122.7(5) . 2_655
C3A C2 C2 126.7(3) . 2_655
O1 C6 O2 125.0(2) 2_656 .
O1 C6 C7 117.8(2) 2_656 .
O2 C6 C7 117.2(2) . .
C8 C7 C13 119.3(2) . .
C8 C7 C6 120.1(2) . .
C13 C7 C6 120.6(2) . .
C7 C8 C9 119.8(3) . .
C7 C8 H8 123.4 . .
C9 C8 H8 116.7 . .
C10 C9 C8 120.9(3) . .
C10 C9 H9 119.1 . .
C8 C9 H9 120 . .
C9 C10 C12 119.1(3) . .
C9 C10 C11 121.3(3) . 3_455
C12 C10 C11 119.6(3) . 3_455
O3 C11 O4 125.4(2) . 2_656
O3 C11 C10 117.6(2) . 3_545
O4 C11 C10 117.0(3) 2_656 3_545
C10 C12 C13 120.4(3) . .
C10 C12 H12 120.1 . .
C13 C12 H12 119.4 . .
C7 C13 C12 120.4(3) . .
C7 C13 H13 119.8 . .
C12 C13 H13 119.8 . .
N2A N1 C3B 100.6(7) . .
N2A N1 C3A 108.0(7) . .
C3B N1 N2B 103.4(7) . .
C3A N1 N2B 104.6(7) . .
N2A N1 Zn1 119.6(6) . .
C3B N1 Zn1 130.7(3) . .
C3A N1 Zn1 131.0(2) . .
N2B N1 Zn1 124.1(7) . .
C6 O1 Zn1 140.26(17) 2_656 .
C6 O2 Zn1 115.90(16) . .
C11 O3 Zn1 138.08(17) . .
C11 O4 Zn1 117.41(18) 2_656 .
N1 Zn1 O4 109.76(8) . .
N1 Zn1 O2 95.95(7) . .
O4 Zn1 O2 87.86(7) . .
N1 Zn1 O3 105.18(7) . .
O4 Zn1 O3 85.74(8) . .
O2 Zn1 O3 158.86(7) . .
N1 Zn1 O1 93.52(7) . .
O4 Zn1 O1 156.67(8) . .
O2 Zn1 O1 88.24(7) . .
O3 Zn1 O1 89.70(7) . .
N1 Zn1 Zn1 163.12(5) . 2_656
O4 Zn1 Zn1 86.72(6) . 2_656
O2 Zn1 Zn1 88.06(5) . 2_656
O3 Zn1 Zn1 71.49(5) . 2_656
O1 Zn1 Zn1 70.16(5) . 2_656
N2A C1A C2 109.7(10) . .
N2A C1A C4A 122.3(11) . .
C2 C1A C4A 128.0(8) . .
C1A N2A N1 111.3(12) . .
N1 N2A H2A 124.4 . .
N1 C3A C2 106.8(3) . .
N1 C3A C5A 125.9(4) . .
C2 C3A C5A 127.3(4) . .
C2 C1B N2B 102.3(10) . .
C2 C1B C4B 134.1(8) . .
N2B C1B C4B 123.6(11) . .
N1 N2B C1B 112.8(12) . .
N1 N2B H2B 123.6 . .
C1B N2B H2B 123.6 . .
C2 C3B N1 112.1(4) . .
C2 C3B C5B 127.6(5) . .
N1 C3B C5B 120.0(5) . .
C3B C5B H5B1 109.5 . .
C3B C5B H5B2 109.5 . .
H5B1 C5B H5B2 109.5 . .
C3B C5B H5B3 109.5 . .
H5B1 C5B H5B3 109.5 . .
H5B2 C5B H5B3 109.5 . .
C1B C4B H4B1 109.5 . .
C1B C4B H4B2 109.5 . .
H4B1 C4B H4B2 109.5 . .
C1B C4B H4B3 109.5 . .
H4B1 C4B H4B3 109.5 . .
H4B2 C4B H4B3 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 C3B 1.349(6) .
C2 C1A 1.370(11) .
C2 C1B 1.398(13) .
C2 C3A 1.436(5) .
C2 C2 1.485(4) 2_655
C6 O1 1.246(3) 2_656
C6 O2 1.270(3) .
C6 C7 1.509(3) .
C7 C8 1.387(4) .
C7 C13 1.388(4) .
C8 C9 1.391(4) .
C8 H8 0.92 .
C9 C10 1.383(4) .
C9 H9 0.96 .
C10 C12 1.384(4) .
C10 C11 1.510(3) 3_455
C11 O3 1.247(3) .
C11 O4 1.267(3) 2_656
C12 C13 1.389(4) .
C12 H12 0.93 .
C13 H13 0.89 .
N1 N2A 1.323(16) .
N1 C3B 1.350(6) .
N1 C3A 1.352(5) .
N1 N2B 1.375(18) .
N1 Zn1 2.0240(17) .
O1 Zn1 2.0613(17) .
O2 Zn1 2.0506(16) .
O3 Zn1 2.0527(18) .
O4 Zn1 2.0409(18) .
Zn1 Zn1 2.9937(6) 2_656
C1A N2A 1.297(19) .
C1A C4A 1.483(12) .
C4A H4A1 1.0485 .
C4A H4A2 1.0485 .
C4A H4A3 1.0485 .
C5A C3A 1.485(7) .
C5A H5A1 0.8569 .
C5A H5A2 0.8569 .
C5A H5A3 0.8569 .
N2A H2A 0.7582 .
C1B N2B 1.41(2) .
C1B C4B 1.478(13) .
N2B H2B 0.7311 .
C3B C5B 1.476(8) .
C5B H5B1 0.8240 .
C4B H4B1 0.8417 .
