#------------------------------------------------------------------------------
#$Date: 2015-06-05 03:11:44 +0300 (Fri, 05 Jun 2015) $
#$Revision: 138047 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/29/4512971.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_4512971
loop_
_publ_author_name
'Arıcı, Mürsel'
'Yeşilel, Okan Zafer'
'Taş, Murat'
_publ_section_title
;
 Coordination Polymers Assembled From
 3,3′,5,5′-Azobenzenetetracarboxylic Acid and Different
 Bis(imidazole) Ligands with Varying Flexibility
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3024
_journal_paper_doi               10.1021/acs.cgd.5b00432
_journal_volume                  15
_journal_year                    2015
_chemical_formula_sum            'C22 H19 N5 O6 Zn'
_chemical_formula_weight         514.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-02-27
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2015-03-04 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 103.3050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0990(2)
_cell_length_b                   12.1358(2)
_cell_length_c                   16.4905(2)
_cell_measurement_temperature    296(2)
_cell_volume                     2161.57(6)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            53188
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.016
_exptl_absorpt_coefficient_mu    1.188
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.912
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0365
_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)+(0.0685P)²+1.2771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1163
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4362
_reflns_number_total             4976
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5b00432_si_006.cif
_cod_data_source_block           ma1893p21n
_cod_depositor_comments
'Adding full bibliography for 4512970--4512974.cif.'
_cod_database_code               4512971
_shelxl_version_number           2013-4
_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   0.512
_shelx_estimated_absorpt_t_max   0.842
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Zn1 Zn 0.22643(2) 0.34648(2) 0.22765(2) 0.03222(10) Uani 1 1 d . .
O1 O 0.19068(15) 0.25895(14) 0.31998(10) 0.0411(4) Uani 1 1 d . .
N1 N 0.04557(17) 0.00156(18) 0.53048(12) 0.0385(4) Uani 1 1 d . .
C1 C 0.2914(2) 0.2320(2) 0.37222(14) 0.0377(5) Uani 1 1 d . .
O4 O 0.57784(16) 0.13176(16) 0.64260(12) 0.0475(4) Uani 1 1 d . .
O2 O 0.39503(17) 0.26113(19) 0.36609(13) 0.0575(5) Uani 1 1 d . .
N2 N 0.31762(17) 0.48538(16) 0.26955(13) 0.0374(4) Uani 1 1 d . .
C2 C 0.2777(2) 0.16223(17) 0.44502(13) 0.0319(4) Uani 1 1 d . .
O5 O 0.0560(7) -0.0357(10) 0.6058(4) 0.336(7) Uani 1 1 d . .
N3 N 0.48721(17) 0.58002(16) 0.31701(12) 0.0366(4) Uani 1 1 d . .
C3 C 0.16478(19) 0.11639(19) 0.44974(13) 0.0330(4) Uani 1 1 d . .
H3 H 0.0948 0.1281 0.4072 0.040 Uiso 1 1 calc R U
N4 N 0.97981(16) 0.71997(17) 0.35926(12) 0.0369(4) Uani 1 1 d . .
C4 C 0.15719(19) 0.05297(19) 0.51842(14) 0.0344(4) Uani 1 1 d . .
O3 O 0.47813(19) 0.0226(2) 0.71424(12) 0.0619(6) Uani 1 1 d . .
N5 N 1.15632(16) 0.77829(16) 0.33641(12) 0.0367(4) Uani 1 1 d . .
C5 C 0.2614(2) 0.0376(2) 0.58406(14) 0.0369(5) Uani 1 1 d . .
H5 H 0.2553 -0.0041 0.6303 0.044 Uiso 1 1 calc R U
O6 O 0.5305(3) 0.0934(3) 0.88748(15) 0.0877(9) Uani 1 1 d G .
H6A H 0.5839 0.1405 0.8804 0.132 Uiso 1 1 d G U
H6B H 0.4962 0.0646 0.8409 0.132 Uiso 1 1 d G U
C6 C 0.37337(19) 0.08490(19) 0.57975(13) 0.0352(5) Uani 1 1 d . .
C7 C 0.3810(2) 0.14528(19) 0.50936(14) 0.0347(5) Uani 1 1 d . .
H7 H 0.4568 0.1748 0.5054 0.042 Uiso 1 1 calc R U
C8 C 0.4840(2) 0.0764(2) 0.65242(14) 0.0401(5) Uani 1 1 d . .
C9 C 0.4305(2) 0.5080(2) 0.25989(15) 0.0384(5) Uani 1 1 d . .
H9 H 0.4653 0.4776 0.2188 0.046 Uiso 1 1 calc R U
C11 C 0.4067(2) 0.6064(2) 0.36569(18) 0.0469(6) Uani 1 1 d . .
H11 H 0.4208 0.6549 0.4105 0.056 Uiso 1 1 calc R U
C10 C 0.3024(2) 0.5478(2) 0.33543(17) 0.0442(5) Uani 1 1 d . .
H10 H 0.2314 0.5496 0.3563 0.053 Uiso 1 1 calc R U
C12 C 0.6139(2) 0.61559(19) 0.32777(15) 0.0360(5) Uani 1 1 d . .
C13 C 0.7035(2) 0.5726(2) 0.39304(15) 0.0404(5) Uani 1 1 d . .
C14 C 0.8249(2) 0.6080(2) 0.39968(15) 0.0407(5) Uani 1 1 d . .
H14 H 0.8878 0.5800 0.4419 0.049 Uiso 1 1 calc R U
C15 C 0.8532(2) 0.6838(2) 0.34469(15) 0.0366(5) Uani 1 1 d . .
C16 C 0.7625(2) 0.7277(2) 0.27925(16) 0.0453(6) Uani 1 1 d . .
C17 C 0.6420(2) 0.6905(2) 0.27248(16) 0.0436(5) Uani 1 1 d . .
H17 H 0.5791 0.7170 0.2296 0.052 Uiso 1 1 calc R U
C21 C 0.6741(3) 0.4904(3) 0.4538(2) 0.0631(8) Uani 1 1 d . .
H21A H 0.7449 0.4441 0.4739 0.095 Uiso 1 1 calc R U
H21B H 0.6052 0.4459 0.4265 0.095 Uiso 1 1 calc R U
H21C H 0.6536 0.5286 0.4998 0.095 Uiso 1 1 calc R U
C22 C 0.7862(3) 0.8151(4) 0.2202(3) 0.0852(14) Uani 1 1 d . .
H22A H 0.8291 0.7832 0.1815 0.128 Uiso 1 1 calc R U
H22B H 0.8359 0.8725 0.2511 0.128 Uiso 1 1 calc R U
H22C H 0.7088 0.8452 0.1902 0.128 Uiso 1 1 calc R U
C18 C 1.0460(2) 0.7376(2) 0.30191(15) 0.0402(5) Uani 1 1 d . .
H18 H 1.0179 0.7230 0.2453 0.048 Uiso 1 1 calc R U
C20 C 1.1622(2) 0.7840(2) 0.42042(15) 0.0424(5) Uani 1 1 d . .
H20 H 1.2299 0.8088 0.4606 0.051 Uiso 1 1 calc R U
C19 C 1.0541(2) 0.7478(2) 0.43567(16) 0.0448(6) Uani 1 1 d . .
H19 H 1.0341 0.7426 0.4873 0.054 Uiso 1 1 calc R 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'
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
O4 Zn1 O1 110.27(8) 4_565 .
O4 Zn1 N2 114.60(8) 4_565 .
O1 Zn1 N2 111.25(8) . .
O4 Zn1 N5 102.79(8) 4_565 2_645
O1 Zn1 N5 116.69(8) . 2_645
N2 Zn1 N5 100.88(8) . 2_645
C1 O1 Zn1 110.87(14) . .
N1 N1 O5 129.3(3) 3_556 .
N1 N1 C4 117.6(2) 3_556 .
O5 N1 C4 113.0(3) . .
O2 C1 O1 123.8(2) . .
O2 C1 C2 119.7(2) . .
O1 C1 C2 116.5(2) . .
C8 O4 Zn1 124.48(16) . 4_666
C9 N2 C10 105.9(2) . .
C9 N2 Zn1 123.22(17) . .
C10 N2 Zn1 126.51(16) . .
C7 C2 C3 119.7(2) . .
C7 C2 C1 118.43(19) . .
C3 C2 C1 121.85(19) . .
C9 N3 C11 107.56(19) . .
C9 N3 C12 124.9(2) . .
C11 N3 C12 127.4(2) . .
C4 C3 C2 119.52(19) . .
C18 N4 C19 107.20(19) . .
C18 N4 C15 127.1(2) . .
C19 N4 C15 125.7(2) . .
C3 C4 C5 120.62(19) . .
C3 C4 N1 124.63(19) . .
C5 C4 N1 114.72(19) . .
C18 N5 C20 106.10(19) . .
C18 N5 Zn1 124.72(17) . 2_655
C20 N5 Zn1 128.06(15) . 2_655
C6 C5 C4 119.7(2) . .
C5 C6 C7 119.25(19) . .
C5 C6 C8 120.4(2) . .
C7 C6 C8 120.2(2) . .
C2 C7 C6 121.16(19) . .
O3 C8 O4 125.9(2) . .
O3 C8 C6 120.5(2) . .
O4 C8 C6 113.6(2) . .
N2 C9 N3 110.9(2) . .
C10 C11 N3 106.2(2) . .
C11 C10 N2 109.5(2) . .
C17 C12 C13 122.1(2) . .
C17 C12 N3 118.7(2) . .
C13 C12 N3 119.2(2) . .
C12 C13 C14 116.9(2) . .
C12 C13 C21 122.6(2) . .
C14 C13 C21 120.4(2) . .
C15 C14 C13 121.1(2) . .
C14 C15 C16 121.9(2) . .
C14 C15 N4 117.1(2) . .
C16 C15 N4 121.0(2) . .
C17 C16 C15 116.5(2) . .
C17 C16 C22 119.0(2) . .
C15 C16 C22 124.4(2) . .
C12 C17 C16 121.5(2) . .
N5 C18 N4 111.1(2) . .
C19 C20 N5 109.4(2) . .
C20 C19 N4 106.2(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O4 1.9215(16) 4_565
Zn1 O1 1.9704(16) .
Zn1 N2 2.005(2) .
Zn1 N5 2.0315(19) 2_645
O1 C1 1.286(3) .
N1 N1 1.252(4) 3_556
N1 O5 1.301(7) .
N1 C4 1.441(3) .
C1 O2 1.230(3) .
C1 C2 1.505(3) .
O4 C8 1.281(3) .
O4 Zn1 1.9216(16) 4_666
N2 C9 1.327(3) .
N2 C10 1.366(3) .
C2 C7 1.387(3) .
C2 C3 1.389(3) .
N3 C9 1.332(3) .
N3 C11 1.370(3) .
N3 C12 1.442(3) .
C3 C4 1.388(3) .
N4 C18 1.341(3) .
N4 C19 1.380(3) .
N4 C15 1.438(3) .
C4 C5 1.403(3) .
O3 C8 1.225(3) .
N5 C18 1.322(3) .
N5 C20 1.373(3) .
N5 Zn1 2.0315(19) 2_655
C5 C6 1.386(3) .
C6 C7 1.392(3) .
C6 C8 1.509(3) .
C11 C10 1.352(4) .
C12 C17 1.374(3) .
C12 C13 1.389(3) .
C13 C14 1.393(3) .
C13 C21 1.502(4) .
C14 C15 1.378(3) .
C15 C16 1.401(3) .
C16 C17 1.391(3) .
C16 C22 1.504(4) .
C20 C19 1.354(3) .
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
C3 H3 O5 0.93 1.99 2.602(6) 122.1 3_556
O6 H6A O1 0.85 2.11 2.919(3) 160.2 4_666
O6 H6B O3 0.85 2.11 2.911(3) 155.9 .
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
Zn1 O1 C1 O2 2.5(3) .
Zn1 O1 C1 C2 -178.50(15) .
O2 C1 C2 C7 8.7(3) .
O1 C1 C2 C7 -170.3(2) .
O2 C1 C2 C3 -172.2(2) .
O1 C1 C2 C3 8.8(3) .
C7 C2 C3 C4 -0.8(3) .
C1 C2 C3 C4 -179.8(2) .
C2 C3 C4 C5 1.9(4) .
C2 C3 C4 N1 179.8(2) .
N1 N1 C4 C3 12.3(4) 3_556
O5 N1 C4 C3 -167.8(7) .
N1 N1 C4 C5 -169.8(3) 3_556
O5 N1 C4 C5 10.2(7) .
C3 C4 C5 C6 -0.9(4) .
N1 C4 C5 C6 -179.0(2) .
C4 C5 C6 C7 -1.2(4) .
C4 C5 C6 C8 175.5(2) .
C3 C2 C7 C6 -1.4(3) .
C1 C2 C7 C6 177.7(2) .
C5 C6 C7 C2 2.4(4) .
C8 C6 C7 C2 -174.3(2) .
Zn1 O4 C8 O3 -6.0(4) 4_666
Zn1 O4 C8 C6 172.22(16) 4_666
C5 C6 C8 O3 4.0(4) .
C7 C6 C8 O3 -179.4(3) .
C5 C6 C8 O4 -174.3(2) .
C7 C6 C8 O4 2.4(3) .
C10 N2 C9 N3 0.9(3) .
Zn1 N2 C9 N3 -156.88(16) .
C11 N3 C9 N2 -0.7(3) .
C12 N3 C9 N2 175.1(2) .
C9 N3 C11 C10 0.1(3) .
C12 N3 C11 C10 -175.5(2) .
N3 C11 C10 N2 0.4(3) .
C9 N2 C10 C11 -0.8(3) .
Zn1 N2 C10 C11 156.02(19) .
C9 N3 C12 C17 76.6(3) .
C11 N3 C12 C17 -108.5(3) .
C9 N3 C12 C13 -102.9(3) .
C11 N3 C12 C13 72.0(3) .
C17 C12 C13 C14 -0.8(4) .
N3 C12 C13 C14 178.7(2) .
C17 C12 C13 C21 -179.8(3) .
N3 C12 C13 C21 -0.3(4) .
C12 C13 C14 C15 1.3(4) .
C21 C13 C14 C15 -179.7(3) .
C13 C14 C15 C16 -0.8(4) .
C13 C14 C15 N4 176.6(2) .
C18 N4 C15 C14 139.5(3) .
C19 N4 C15 C14 -43.5(4) .
C18 N4 C15 C16 -43.0(4) .
C19 N4 C15 C16 134.0(3) .
C14 C15 C16 C17 -0.1(4) .
N4 C15 C16 C17 -177.5(2) .
C14 C15 C16 C22 176.5(3) .
N4 C15 C16 C22 -0.9(5) .
C13 C12 C17 C16 -0.2(4) .
N3 C12 C17 C16 -179.7(2) .
C15 C16 C17 C12 0.6(4) .
C22 C16 C17 C12 -176.2(3) .
C20 N5 C18 N4 1.8(3) .
Zn1 N5 C18 N4 -166.86(16) 2_655
C19 N4 C18 N5 -2.1(3) .
C15 N4 C18 N5 175.3(2) .
C18 N5 C20 C19 -0.8(3) .
Zn1 N5 C20 C19 167.36(18) 2_655
N5 C20 C19 N4 -0.5(3) .
C18 N4 C19 C20 1.5(3) .
C15 N4 C19 C20 -175.9(2) .
