#------------------------------------------------------------------------------
#$Date: 2015-06-05 03:11:44 +0300 (Fri, 05 Jun 2015) $
#$Revision: 138047 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/29/4512973.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_4512973
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_moiety         'C22 H17 Cd N5 O5'
_chemical_formula_sum            'C22 H17 Cd N5 O5'
_chemical_formula_weight         543.81
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-02-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                109.491(2)
_cell_angle_beta                 95.535(2)
_cell_angle_gamma                97.425(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6453(4)
_cell_length_b                   10.3129(5)
_cell_length_c                   12.7250(6)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      33.18
_cell_measurement_theta_min      2.40
_cell_volume                     1048.66(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21800
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.13
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.088
_exptl_absorpt_correction_T_max  0.9426
_exptl_absorpt_correction_T_min  0.7726
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.055
_refine_diff_density_max         2.899
_refine_diff_density_min         -5.600
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4273
_refine_ls_number_restraints     85
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0812P)²+4.9064P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1429
_refine_ls_wR_factor_ref         0.1447
_reflns_number_gt                4055
_reflns_number_total             4273
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00432_si_004.cif
_cod_data_source_block           ma1334_0m_a_a
_cod_depositor_comments
'Adding full bibliography for 4512970--4512974.cif.'
_cod_database_code               4512973
_shelxl_version_number           2013-4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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
Cd1 Cd -0.09387(4) 0.77204(3) 0.89481(3) 0.02387(15) Uani 1 1 d . U
O3 O -0.0381(6) 1.5398(5) 0.8767(4) 0.0541(7) Uani 1 1 d . U
O1 O -0.2271(5) 0.9045(4) 0.8266(4) 0.0389(9) Uani 1 1 d . U
O4 O -0.2158(6) 1.5551(5) 0.7459(4) 0.0541(7) Uani 1 1 d . U
N4 N 0.2732(6) 0.2852(5) 0.9994(4) 0.0356(10) Uani 1 1 d . U
N3 N 0.3742(6) 0.3799(5) 0.8849(4) 0.0370(10) Uani 1 1 d . U
O2 O -0.0559(7) 1.0878(5) 0.9366(4) 0.0619(15) Uani 1 1 d . U
C2 C -0.2093(5) 1.1112(5) 0.7836(4) 0.0223(9) Uani 1 1 d . U
N5 N -0.4560(7) 1.0561(5) 0.5091(4) 0.0428(12) Uani 1 1 d . U
C3 C -0.1523(6) 1.2537(5) 0.8171(4) 0.0240(9) Uani 1 1 d . U
H3 H -0.0829 1.2982 0.8840 0.029 Uiso 1 1 calc R .
C4 C -0.1979(6) 1.3299(5) 0.7517(4) 0.0262(10) Uani 1 1 d . U
C1 C -0.1609(6) 1.0303(5) 0.8560(4) 0.0268(10) Uani 1 1 d . U
N1 N 0.1164(6) 0.7880(5) 0.8054(5) 0.0448(12) Uani 1 1 d . U
C7 C -0.3123(6) 1.0434(5) 0.6834(4) 0.0263(10) Uani 1 1 d . U
H7 H -0.3516 0.9484 0.6613 0.032 Uiso 1 1 calc R .
N2 N 0.3119(7) 0.7079(6) 0.7213(5) 0.0476(13) Uani 1 1 d . U
C8 C -0.1459(6) 1.4853(5) 0.7934(4) 0.0264(10) Uani 1 1 d . U
C5 C -0.3003(7) 1.2613(5) 0.6502(4) 0.0316(11) Uani 1 1 d . U
H5 H -0.3311 1.3110 0.6051 0.038 Uiso 1 1 calc R .
C20 C 0.2579(7) 0.3737(6) 0.9461(5) 0.0342(11) Uani 1 1 d . U
H20 H 0.185(9) 0.416(8) 0.949(6) 0.041 Uiso 1 1 d R .
C6 C -0.3556(7) 1.1191(5) 0.6170(4) 0.0337(12) Uani 1 1 d . U
C22 C 0.4080(8) 0.2331(7) 0.9700(6) 0.0431(13) Uani 1 1 d . U
H22 H 0.450(9) 0.174(8) 1.008(7) 0.052 Uiso 1 1 d R .
C21 C 0.4694(9) 0.2899(8) 0.8986(6) 0.0496(15) Uani 1 1 d . U
H21 H 0.552(10) 0.281(8) 0.856(7) 0.060 Uiso 1 1 d R .
C19 C 0.3926(10) 0.4641(8) 0.8132(6) 0.0477(15) Uani 1 1 d . U
H19A H 0.510(10) 0.512(8) 0.822(7) 0.057 Uiso 1 1 d R .
H19B H 0.346(10) 0.530(9) 0.835(7) 0.057 Uiso 1 1 d R .
C18 C 0.3149(8) 0.3904(7) 0.6930(5) 0.0446(14) Uani 1 1 d . U
C9 C 0.1619(8) 0.6809(7) 0.7358(7) 0.0487(15) Uani 1 1 d . U
H9 H 0.102(10) 0.597(9) 0.693(7) 0.058 Uiso 1 1 d R .
C13 C 0.3247(9) 0.4643(8) 0.6175(6) 0.0528(16) Uani 1 1 d . U
C12 C 0.4057(10) 0.6127(10) 0.6540(8) 0.0610(19) Uani 1 1 d . U
H12A H 0.495(11) 0.612(10) 0.694(8) 0.073 Uiso 1 1 d R .
H12B H 0.427(11) 0.634(10) 0.593(8) 0.073 Uiso 1 1 d R .
C17 C 0.2334(12) 0.2547(9) 0.6548(7) 0.063(2) Uani 1 1 d . U
H17 H 0.237(12) 0.211(10) 0.699(9) 0.076 Uiso 1 1 d R .
C14 C 0.2515(13) 0.3977(12) 0.5061(7) 0.077(2) Uani 1 1 d . U
H14 H 0.2572 0.4456 0.4560 0.092 Uiso 1 1 calc R .
C11 C 0.3669(11) 0.8435(10) 0.7901(10) 0.081(3) Uani 1 1 d . U
H11 H 0.475(13) 0.874(11) 0.780(9) 0.097 Uiso 1 1 d R .
C10 C 0.2449(11) 0.8909(9) 0.8395(10) 0.085(3) Uani 1 1 d . U
H10 H 0.2479 0.9809 0.8896 0.102 Uiso 1 1 calc R .
C15 C 0.1727(16) 0.2656(14) 0.4697(7) 0.094(3) Uani 1 1 d . U
H15 H 0.109(14) 0.226(12) 0.386(11) 0.113 Uiso 1 1 d R .
C16 C 0.1639(15) 0.1922(12) 0.5437(9) 0.087(3) Uani 1 1 d . U
H16 H 0.108(14) 0.099(13) 0.546(10) 0.105 Uiso 1 1 d R .
O5 O -0.4160(6) 1.1255(5) 0.4373(4) 0.0541(7) Uani 1 1 d . 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'
Cd Cd -0.8075 1.2024 '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'
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
O3 Cd1 C8 27.15(16) 1_545 1_545
O1 Cd1 O3 148.62(16) . 1_545
O1 Cd1 O4 94.55(16) . 1_545
O1 Cd1 N4 98.68(17) . 2_567
O1 Cd1 O2 108.27(16) . 2_577
O1 Cd1 N1 96.71(19) . .
O1 Cd1 C8 121.55(15) . 1_545
O4 Cd1 O3 54.07(17) 1_545 1_545
O4 Cd1 C8 27.10(16) 1_545 1_545
N4 Cd1 O3 81.30(18) 2_567 1_545
N4 Cd1 O4 86.29(18) 2_567 1_545
N4 Cd1 O2 86.3(2) 2_567 2_577
N4 Cd1 C8 80.74(16) 2_567 1_545
O2 Cd1 O3 103.05(17) 2_577 1_545
O2 Cd1 O4 156.81(17) 2_577 1_545
O2 Cd1 C8 129.77(15) 2_577 1_545
N1 Cd1 O3 84.86(19) . 1_545
N1 Cd1 O4 91.1(2) . 1_545
N1 Cd1 N4 164.5(2) . 2_567
N1 Cd1 O2 90.2(2) . 2_577
N1 Cd1 C8 90.05(17) . 1_545
C8 O3 Cd1 90.5(3) . 1_565
C1 O1 Cd1 114.8(3) . .
C8 O4 Cd1 91.4(3) . 1_565
C20 N4 Cd1 124.3(4) . 2_567
C20 N4 C22 105.2(5) . .
C22 N4 Cd1 130.4(4) . 2_567
C20 N3 C21 107.5(5) . .
C20 N3 C19 126.3(6) . .
C21 N3 C19 126.2(6) . .
C1 O2 Cd1 165.6(5) . 2_577
C3 C2 C1 120.1(4) . .
C7 C2 C3 120.2(4) . .
C7 C2 C1 119.6(4) . .
N5 N5 C6 117.9(6) 2_476 .
N5 N5 O5 130.8(6) 2_476 .
O5 N5 C6 110.5(5) . .
C4 C3 C2 120.6(4) . .
C3 C4 C8 120.0(4) . .
C3 C4 C5 119.1(4) . .
C5 C4 C8 120.8(4) . .
O1 C1 C2 117.3(4) . .
O2 C1 O1 124.1(5) . .
O2 C1 C2 118.5(5) . .
C9 N1 Cd1 123.6(4) . .
C9 N1 C10 105.3(6) . .
C10 N1 Cd1 127.3(5) . .
C6 C7 C2 119.1(4) . .
C9 N2 C12 128.5(7) . .
C9 N2 C11 105.8(6) . .
C11 N2 C12 125.6(7) . .
O3 C8 Cd1 62.4(3) . 1_565
O3 C8 C4 118.3(5) . .
O4 C8 Cd1 61.5(3) . 1_565
O4 C8 O3 123.2(5) . .
O4 C8 C4 118.4(5) . .
C4 C8 Cd1 169.3(3) . 1_565
C6 C5 C4 119.9(5) . .
N4 C20 N3 111.4(5) . .
C7 C6 N5 122.9(5) . .
C7 C6 C5 121.0(5) . .
C5 C6 N5 116.1(5) . .
C21 C22 N4 109.6(6) . .
C22 C21 N3 106.4(6) . .
N3 C19 C18 114.0(6) . .
C13 C18 C19 118.1(6) . .
C17 C18 C19 122.5(6) . .
C17 C18 C13 119.4(7) . .
N1 C9 N2 112.7(6) . .
C18 C13 C12 122.2(7) . .
C14 C13 C18 118.7(8) . .
C14 C13 C12 119.0(7) . .
N2 C12 C13 111.3(6) . .
C16 C17 C18 120.1(9) . .
C15 C14 C13 121.5(9) . .
C10 C11 N2 106.3(7) . .
C11 C10 N1 109.9(8) . .
C14 C15 C16 119.9(9) . .
C17 C16 C15 120.4(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cd1 O3 2.444(5) 1_545
Cd1 O1 2.225(4) .
Cd1 O4 2.426(5) 1_545
Cd1 N4 2.294(5) 2_567
Cd1 O2 2.297(4) 2_577
Cd1 N1 2.253(5) .
Cd1 C8 2.759(5) 1_545
O3 Cd1 2.444(5) 1_565
O3 C8 1.259(7) .
O1 C1 1.262(6) .
O4 Cd1 2.426(5) 1_565
O4 C8 1.257(7) .
N4 Cd1 2.294(5) 2_567
N4 C20 1.318(7) .
N4 C22 1.378(8) .
N3 C20 1.338(8) .
N3 C21 1.360(9) .
N3 C19 1.460(8) .
O2 Cd1 2.297(4) 2_577
O2 C1 1.227(7) .
C2 C3 1.393(6) .
C2 C1 1.499(6) .
C2 C7 1.390(7) .
N5 N5 1.238(10) 2_476
N5 C6 1.446(7) .
N5 O5 1.378(7) .
C3 C4 1.385(7) .
C4 C8 1.501(7) .
C4 C5 1.400(7) .
N1 C9 1.298(9) .
N1 C10 1.358(9) .
C7 C6 1.386(7) .
N2 C9 1.334(8) .
N2 C12 1.460(9) .
N2 C11 1.371(11) .
C8 Cd1 2.759(5) 1_565
C5 C6 1.387(7) .
C22 C21 1.348(10) .
C19 C18 1.504(10) .
C18 C13 1.414(9) .
C18 C17 1.384(11) .
C13 C12 1.495(13) .
C13 C14 1.395(12) .
C17 C16 1.380(13) .
C14 C15 1.346(17) .
C11 C10 1.343(13) .
C15 C16 1.393(17) .
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_4
Cd1 O3 C8 O4 9.5(6) 1_565 .
Cd1 O3 C8 C4 -168.0(4) 1_565 .
Cd1 O1 C1 O2 -18.5(8) . .
Cd1 O1 C1 C2 158.3(3) . .
Cd1 O4 C8 O3 -9.6(6) 1_565 .
Cd1 O4 C8 C4 167.9(4) 1_565 .
Cd1 N4 C20 N3 -175.7(4) 2_567 .
Cd1 N4 C22 C21 174.8(5) 2_567 .
Cd1 O2 C1 O1 -114.3(16) 2_577 .
Cd1 O2 C1 C2 69(2) 2_577 .
Cd1 N1 C9 N2 -160.0(5) . .
Cd1 N1 C10 C11 157.8(8) . .
N4 C22 C21 N3 1.1(8) . .
N3 C19 C18 C13 179.2(6) . .
N3 C19 C18 C17 0.0(11) . .
C2 C3 C4 C8 175.1(5) . .
C2 C3 C4 C5 -1.0(8) . .
C2 C7 C6 N5 176.9(5) . .
C2 C7 C6 C5 -1.3(9) . .
N5 N5 C6 C7 22.7(11) 2_476 .
N5 N5 C6 C5 -159.0(8) 2_476 .
C3 C2 C1 O1 173.8(5) . .
C3 C2 C1 O2 -9.2(8) . .
C3 C2 C7 C6 0.8(8) . .
C3 C4 C8 Cd1 -78(2) . 1_565
C3 C4 C8 O3 13.2(7) . .
C3 C4 C8 O4 -164.3(5) . .
C3 C4 C5 C6 0.6(8) . .
C4 C5 C6 N5 -177.7(5) . .
C4 C5 C6 C7 0.6(9) . .
C1 C2 C3 C4 -179.1(5) . .
C1 C2 C7 C6 -179.7(5) . .
C7 C2 C3 C4 0.4(8) . .
C7 C2 C1 O1 -5.7(7) . .
C7 C2 C1 O2 171.4(6) . .
N2 C11 C10 N1 1.4(14) . .
C8 C4 C5 C6 -175.5(5) . .
C5 C4 C8 Cd1 98(2) . 1_565
C5 C4 C8 O3 -170.7(5) . .
C5 C4 C8 O4 11.7(8) . .
C20 N4 C22 C21 -0.9(8) . .
C20 N3 C21 C22 -0.9(8) . .
C20 N3 C19 C18 -90.7(8) . .
C22 N4 C20 N3 0.3(7) . .
C21 N3 C20 N4 0.4(7) . .
C21 N3 C19 C18 87.0(9) . .
C19 N3 C20 N4 178.4(6) . .
C19 N3 C21 C22 -179.0(6) . .
C19 C18 C13 C12 -1.5(10) . .
C19 C18 C13 C14 -179.2(7) . .
C19 C18 C17 C16 179.8(9) . .
C18 C13 C12 N2 -73.6(9) . .
C18 C13 C14 C15 -0.1(12) . .
C18 C17 C16 C15 -1.1(16) . .
C9 N1 C10 C11 -0.4(12) . .
C9 N2 C12 C13 -12.0(11) . .
C9 N2 C11 C10 -1.7(12) . .
C13 C18 C17 C16 0.6(13) . .
C13 C14 C15 C16 -0.4(16) . .
C12 N2 C9 N1 177.0(7) . .
C12 N2 C11 C10 -177.4(9) . .
C12 C13 C14 C15 -177.9(8) . .
C17 C18 C13 C12 177.7(7) . .
C17 C18 C13 C14 0.0(10) . .
C14 C13 C12 N2 104.1(8) . .
C14 C15 C16 C17 1.0(18) . .
C11 N2 C9 N1 1.6(10) . .
C11 N2 C12 C13 162.7(8) . .
C10 N1 C9 N2 -0.7(10) . .
O5 N5 C6 C7 -148.0(6) . .
O5 N5 C6 C5 30.3(8) . .
