#------------------------------------------------------------------------------
#$Date: 2015-06-05 03:11:44 +0300 (Fri, 05 Jun 2015) $
#$Revision: 138047 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/29/4512974.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_4512974
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 Mn N5 O5'
_chemical_formula_sum            'C22 H17 Mn N5 O5'
_chemical_formula_weight         486.35
_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   geom
_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                108.2540(10)
_cell_angle_beta                 97.8360(10)
_cell_angle_gamma                97.3020(10)
_cell_formula_units_Z            2
_cell_length_a                   8.60730(10)
_cell_length_b                   10.2090(2)
_cell_length_c                   12.6781(2)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      33.17
_cell_measurement_theta_min      2.43
_cell_volume                     1030.90(3)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0199
_diffrn_reflns_av_unetI/netI     0.0154
_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            20605
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.72
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  0.9220
_exptl_absorpt_correction_T_min  0.7850
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             498
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         4.383
_refine_diff_density_min         -3.783
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0920
_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)+(0.1562P)²+4.3950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2499
_refine_ls_wR_factor_ref         0.2521
_reflns_number_gt                3970
_reflns_number_total             4200
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00432_si_003.cif
_cod_data_source_block           ma1561_0m_a
_cod_depositor_comments
'Adding full bibliography for 4512970--4512974.cif.'
_cod_original_cell_volume        1030.89(3)
_cod_database_code               4512974
_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
Mn1 Mn 1.08796(8) 0.23270(6) 0.10926(5) 0.0237(3) Uani 1 1 d .
O2 O 0.7919(4) -0.0916(3) -0.1651(3) 0.0356(8) Uani 1 1 d .
O3 O 0.9612(4) 0.5475(3) -0.1205(3) 0.0300(7) Uani 1 1 d .
O4 O 0.7786(5) 0.5640(3) -0.2526(3) 0.0359(8) Uani 1 1 d .
O1 O 0.9261(6) 0.1067(4) -0.0389(4) 0.0615(14) Uani 1 1 d .
N5 N 0.5400(12) 0.0588(9) -0.4893(7) 0.0992(18) Uani 1 1 d .
N4 N 0.7351(6) 0.7192(5) -0.0049(4) 0.0380(10) Uani 1 1 d .
C4 C 0.7957(5) 0.3355(4) -0.2451(4) 0.0253(9) Uani 1 1 d .
N3 N 0.6268(5) 0.6277(5) 0.1097(4) 0.0396(10) Uani 1 1 d .
N1 N 0.8947(6) 0.2208(5) 0.2067(5) 0.0467(11) Uani 1 1 d .
C2 C 0.7910(5) 0.1174(4) -0.2082(3) 0.0227(8) Uani 1 1 d .
C3 C 0.8441(5) 0.2615(4) -0.1751(4) 0.0239(8) Uani 1 1 d .
H3 H 0.9121 0.3083 -0.1060 0.029 Uiso 1 1 calc R
C8 C 0.8498(5) 0.4931(4) -0.2042(4) 0.0258(9) Uani 1 1 d .
C7 C 0.6899(5) 0.0471(4) -0.3118(4) 0.0268(9) Uani 1 1 d .
H7 H 0.6548 -0.0493 -0.3342 0.032 Uiso 1 1 calc R
C1 C 0.8410(5) 0.0386(4) -0.1311(4) 0.0256(9) Uani 1 1 d .
C5 C 0.6953(6) 0.2665(5) -0.3480(4) 0.0333(10) Uani 1 1 d .
H5 H 0.6635 0.3163 -0.3948 0.040 Uiso 1 1 calc R
C6 C 0.6413(6) 0.1216(5) -0.3820(4) 0.0325(10) Uani 1 1 d .
C20 C 0.7439(6) 0.6291(6) 0.0501(4) 0.0353(10) Uani 1 1 d .
H20 H 0.8217 0.5734 0.0477 0.042 Uiso 1 1 calc R
N2 N 0.6948(6) 0.2944(7) 0.2832(5) 0.0557(14) Uani 1 1 d .
C19 C 0.6049(9) 0.5414(7) 0.1813(5) 0.0526(15) Uani 1 1 d .
H19A H 0.6485 0.4570 0.1520 0.063 Uiso 1 1 calc R
H19B H 0.4916 0.5133 0.1770 0.063 Uiso 1 1 calc R
C9 C 0.8430(8) 0.3273(7) 0.2677(6) 0.0547(16) Uani 1 1 d .
H9 H 0.9029 0.4175 0.2978 0.066 Uiso 1 1 calc R
C22 C 0.6018(8) 0.7750(7) 0.0204(5) 0.0513(15) Uani 1 1 d .
H22 H 0.5634 0.8414 -0.0072 0.062 Uiso 1 1 calc R
C21 C 0.5350(8) 0.7202(8) 0.0906(6) 0.0552(15) Uani 1 1 d .
H21 H 0.4445 0.7412 0.1201 0.066 Uiso 1 1 calc R
C18 C 0.6830(8) 0.6151(8) 0.3039(5) 0.0511(15) Uani 1 1 d .
C13 C 0.6756(9) 0.5404(10) 0.3806(6) 0.064(2) Uani 1 1 d .
C12 C 0.5953(10) 0.3872(10) 0.3426(8) 0.077(3) Uani 1 1 d .
H12A H 0.5742 0.3631 0.4081 0.092 Uiso 1 1 calc R
H12B H 0.4939 0.3738 0.2930 0.092 Uiso 1 1 calc R
C17 C 0.7603(11) 0.7532(9) 0.3432(7) 0.072(2) Uani 1 1 d .
H17 H 0.7648 0.8029 0.2932 0.087 Uiso 1 1 calc R
C14 C 0.7454(13) 0.6039(13) 0.4909(7) 0.086(3) Uani 1 1 d .
H14 H 0.7401 0.5537 0.5406 0.103 Uiso 1 1 calc R
C15 C 0.8211(15) 0.7362(16) 0.5294(7) 0.109(5) Uani 1 1 d .
H15 H 0.8686 0.7766 0.6053 0.131 Uiso 1 1 calc R
C10 C 0.7700(12) 0.1112(9) 0.1786(10) 0.098(4) Uani 1 1 d .
H10 H 0.7692 0.0201 0.1322 0.118 Uiso 1 1 calc R
C16 C 0.8311(14) 0.8188(12) 0.4557(9) 0.103(4) Uani 1 1 d .
H16 H 0.8828 0.9118 0.4827 0.124 Uiso 1 1 calc R
C11 C 0.6514(13) 0.1547(12) 0.2272(13) 0.117(5) Uani 1 1 d .
H11 H 0.5550 0.0993 0.2238 0.140 Uiso 1 1 calc R
O5 O 0.5822(10) 0.1212(7) -0.5637(5) 0.0992(18) Uani 1 1 d .
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'
Mn Mn 0.3368 0.7283 '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
O2 Mn1 O3 153.62(13) 2_755 2_765
O2 Mn1 O4 96.85(13) 2_755 2_765
O2 Mn1 N4 96.29(16) 2_755 2_765
O2 Mn1 N1 94.77(18) 2_755 .
O2 Mn1 C8 125.14(14) 2_755 2_765
O3 Mn1 O4 56.79(12) 2_765 2_765
O3 Mn1 C8 28.50(13) 2_765 2_765
O4 Mn1 C8 28.44(14) 2_765 2_765
O1 Mn1 O2 105.20(15) . 2_755
O1 Mn1 O3 101.16(14) . 2_765
O1 Mn1 O4 157.95(15) . 2_765
O1 Mn1 N4 90.5(2) . 2_765
O1 Mn1 N1 88.8(2) . .
O1 Mn1 C8 129.55(15) . 2_765
N4 Mn1 O3 82.64(14) 2_765 2_765
N4 Mn1 O4 86.71(15) 2_765 2_765
N4 Mn1 C8 81.79(15) 2_765 2_765
N1 Mn1 O3 86.44(16) . 2_765
N1 Mn1 O4 89.72(17) . 2_765
N1 Mn1 N4 168.71(18) . 2_765
N1 Mn1 C8 89.99(16) . 2_765
C1 O2 Mn1 123.7(3) . 2_755
C8 O3 Mn1 90.4(3) . 2_765
C8 O4 Mn1 89.5(3) . 2_765
C1 O1 Mn1 173.8(5) . .
N5 N5 C6 118.1(9) 2_654 .
N5 N5 O5 127.7(10) 2_654 .
O5 N5 C6 111.2(6) . .
C20 N4 Mn1 125.0(4) . 2_765
C20 N4 C22 104.4(5) . .
C22 N4 Mn1 130.6(4) . 2_765
C3 C4 C8 118.7(4) . .
C5 C4 C3 120.2(4) . .
C5 C4 C8 121.0(4) . .
C20 N3 C19 125.3(5) . .
C20 N3 C21 107.3(5) . .
C21 N3 C19 127.5(5) . .
C9 N1 Mn1 125.1(4) . .
C9 N1 C10 104.6(6) . .
C10 N1 Mn1 125.2(6) . .
C3 C2 C1 119.8(4) . .
C7 C2 C3 120.1(4) . .
C7 C2 C1 120.1(4) . .
C4 C3 C2 120.1(4) . .
O3 C8 Mn1 61.1(2) . 2_765
O3 C8 C4 118.3(4) . .
O4 C8 Mn1 62.1(2) . 2_765
O4 C8 O3 122.7(4) . .
O4 C8 C4 118.9(4) . .
C4 C8 Mn1 170.5(3) . 2_765
C2 C7 C6 119.8(4) . .
O2 C1 C2 117.6(4) . .
O1 C1 O2 125.0(4) . .
O1 C1 C2 117.4(4) . .
C4 C5 C6 120.0(4) . .
C7 C6 N5 123.8(5) . .
C7 C6 C5 119.8(4) . .
C5 C6 N5 116.4(5) . .
N4 C20 N3 111.8(5) . .
C9 N2 C12 128.6(7) . .
C9 N2 C11 105.0(7) . .
C11 N2 C12 126.3(7) . .
N3 C19 C18 113.6(5) . .
N1 C9 N2 113.0(6) . .
C21 C22 N4 110.5(6) . .
C22 C21 N3 106.0(5) . .
C13 C18 C19 118.8(7) . .
C17 C18 C19 122.0(6) . .
C17 C18 C13 119.1(7) . .
C18 C13 C12 121.9(7) . .
C14 C13 C18 120.0(9) . .
C14 C13 C12 118.0(8) . .
N2 C12 C13 111.4(6) . .
C18 C17 C16 121.2(9) . .
C15 C14 C13 121.3(9) . .
C14 C15 C16 121.4(8) . .
C11 C10 N1 109.5(8) . .
C17 C16 C15 117.0(11) . .
C10 C11 N2 107.8(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 O2 2.112(3) 2_755
Mn1 O3 2.301(3) 2_765
Mn1 O4 2.322(3) 2_765
Mn1 O1 2.108(4) .
Mn1 N4 2.253(4) 2_765
Mn1 N1 2.216(5) .
Mn1 C8 2.628(4) 2_765
O2 Mn1 2.112(3) 2_755
O2 C1 1.257(5) .
O3 Mn1 2.301(3) 2_765
O3 C8 1.254(6) .
O4 Mn1 2.322(3) 2_765
O4 C8 1.251(6) .
O1 C1 1.230(6) .
N5 N5 1.234(15) 2_654
N5 C6 1.418(9) .
N5 O5 1.356(10) .
N4 Mn1 2.253(4) 2_765
N4 C20 1.320(7) .
N4 C22 1.377(8) .
C4 C3 1.390(6) .
C4 C8 1.515(5) .
C4 C5 1.381(7) .
N3 C20 1.341(7) .
N3 C19 1.463(7) .
N3 C21 1.363(9) .
N1 C9 1.292(9) .
N1 C10 1.367(9) .
C2 C3 1.393(6) .
C2 C7 1.391(6) .
C2 C1 1.502(6) .
C8 Mn1 2.628(4) 2_765
C7 C6 1.396(6) .
C5 C6 1.401(6) .
N2 C9 1.333(8) .
N2 C12 1.461(10) .
N2 C11 1.355(12) .
C19 C18 1.513(9) .
C22 C21 1.343(9) .
C18 C13 1.414(9) .
C18 C17 1.382(11) .
C13 C12 1.522(13) .
C13 C14 1.357(12) .
C17 C16 1.384(12) .
C14 C15 1.328(17) .
C15 C16 1.444(18) .
C10 C11 1.318(14) .
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
Mn1 O2 C1 O1 -26.4(8) 2_755
Mn1 O2 C1 C2 154.2(3) 2_755
Mn1 O3 C8 O4 8.4(5) 2_765
Mn1 O3 C8 C4 -169.2(3) 2_765
Mn1 O4 C8 O3 -8.3(5) 2_765
Mn1 O4 C8 C4 169.3(4) 2_765
Mn1 N4 C20 N3 176.7(3) 2_765
Mn1 N4 C22 C21 -176.9(4) 2_765
Mn1 N1 C9 N2 156.9(5) .
Mn1 N1 C10 C11 -158.1(9) .
N5 N5 C6 C7 18.2(19) 2_654
N5 N5 C6 C5 -162.8(13) 2_654
N4 C22 C21 N3 -0.3(8) .
C4 C5 C6 N5 -179.3(7) .
C4 C5 C6 C7 -0.3(8) .
N3 C19 C18 C13 -177.5(6) .
N3 C19 C18 C17 3.0(10) .
N1 C10 C11 N2 2.8(16) .
C2 C7 C6 N5 179.3(7) .
C2 C7 C6 C5 0.3(7) .
C3 C4 C8 O3 14.5(6) .
C3 C4 C8 O4 -163.3(4) .
C3 C4 C5 C6 0.3(8) .
C3 C2 C7 C6 -0.3(7) .
C3 C2 C1 O2 -179.1(4) .
C3 C2 C1 O1 1.5(7) .
C8 C4 C3 C2 177.3(4) .
C8 C4 C5 C6 -177.3(4) .
C7 C2 C3 C4 0.3(7) .
C7 C2 C1 O2 1.9(6) .
C7 C2 C1 O1 -177.6(5) .
C1 C2 C3 C4 -178.7(4) .
C1 C2 C7 C6 178.7(4) .
C5 C4 C3 C2 -0.3(7) .
C5 C4 C8 O3 -167.9(4) .
C5 C4 C8 O4 14.3(7) .
C20 N4 C22 C21 1.0(7) .
C20 N3 C19 C18 93.3(7) .
C20 N3 C21 C22 -0.5(7) .
C19 N3 C20 N4 -178.8(5) .
C19 N3 C21 C22 179.5(6) .
C19 C18 C13 C12 1.7(9) .
C19 C18 C13 C14 179.7(7) .
C19 C18 C17 C16 -180.0(8) .
C9 N1 C10 C11 -2.5(13) .
C9 N2 C12 C13 5.3(11) .
C9 N2 C11 C10 -2.0(14) .
C22 N4 C20 N3 -1.3(6) .
C21 N3 C20 N4 1.2(7) .
C21 N3 C19 C18 -86.7(8) .
C18 C13 C12 N2 75.8(9) .
C18 C13 C14 C15 0.2(13) .
C18 C17 C16 C15 0.3(15) .
C13 C18 C17 C16 0.5(12) .
C13 C14 C15 C16 0.6(16) .
C12 N2 C9 N1 -177.1(7) .
C12 N2 C11 C10 175.6(9) .
C12 C13 C14 C15 178.3(8) .
C17 C18 C13 C12 -178.8(7) .
C17 C18 C13 C14 -0.8(10) .
C14 C13 C12 N2 -102.2(8) .
C14 C15 C16 C17 -0.9(16) .
C10 N1 C9 N2 1.2(9) .
C11 N2 C9 N1 0.4(11) .
C11 N2 C12 C13 -171.7(10) .
O5 N5 C6 C7 -143.7(7) .
O5 N5 C6 C5 35.3(11) .
