#------------------------------------------------------------------------------
#$Date: 2018-04-30 18:49:19 +0300 (Mon, 30 Apr 2018) $
#$Revision: 207527 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/10/2021088.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_2021088
loop_
_publ_author_name
'Liu, Yan-Ju'
'Cheng, Di'
'Li, Ya-Xue'
'Meng, Xiang-Ru'
'Yang, Huai-Xia'
_publ_section_title
;
 A new two-dimensional managnese(II) coordination polymer constructed by
 2,2'-(1,2-phenylene)bis(1H-imidazole-4,5-dicarboxylate)
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              599
_journal_page_last               603
_journal_paper_doi               10.1107/S2053229618005508
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          '[Mn (C16 H8 N4 O8)]'
_chemical_formula_moiety         'C16 H8 Mn N4 O8'
_chemical_formula_sum            'C16 H8 Mn N4 O8'
_chemical_formula_weight         439.20
_chemical_name_systematic
Poly[[μ₃-2,2'-(1,2-phenylene)bis(4-carboxy-1H-imidazole-5-carboxylato)-κ⁶O⁴,N³,N^3'^,O^4'^:O⁵:O^5'^:]manganese(II)]
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.108(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3422(4)
_cell_length_b                   16.4500(8)
_cell_length_c                   11.8773(5)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.45
_cell_volume                     1627.51(13)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2005)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22393
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.577
_diffrn_reflns_theta_min         3.014
_exptl_absorpt_coefficient_mu    0.872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2000)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_description       block
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.364
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0394P)²+0.9243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0843
_reflns_number_gt                3244
_reflns_number_total             3753
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk3685sup1.cif
_cod_data_source_block           I
_cod_database_code               2021088
_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   0.838
_shelx_estimated_absorpt_t_max   0.880
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
Mn Mn1 1.00156(3) 0.56363(2) 0.17925(2) 0.02691(9) Uani d 1 . .
N N1 0.47745(17) 0.61064(9) 0.11776(13) 0.0300(3) Uani d 1 . .
H H1A 0.3909 0.6371 0.1001 0.036 Uiso calc 1 . .
N N2 0.73381(17) 0.58357(9) 0.15029(13) 0.0286(3) Uani d 1 . .
N N3 0.96790(17) 0.68247(9) 0.25923(13) 0.0283(3) Uani d 1 . .
N N4 0.91528(18) 0.80371(9) 0.32423(13) 0.0297(3) Uani d 1 . .
H H4A 0.8733 0.8512 0.3293 0.036 Uiso calc 1 . .
O O1 0.21031(16) 0.50309(11) 0.13295(15) 0.0541(4) Uani d 1 A 1
O O2 0.37463(18) 0.40264(10) 0.18115(15) 0.0511(4) Uani d 1 . .
O O3 0.66409(18) 0.37515(9) 0.22286(16) 0.0504(4) Uani d 1 . .
H H3 0.5670 0.3829 0.2148 0.076 Uiso calc 1 . .
O O4 0.88557(16) 0.44914(8) 0.22465(13) 0.0376(3) Uani d 1 . .
O O5 1.0169(2) 0.88073(9) 0.51987(12) 0.0450(4) Uani d 1 B 1
O O6 1.20124(17) 0.78402(9) 0.55902(13) 0.0430(4) Uani d 1 . .
O O7 1.2319(2) 0.63322(10) 0.50006(14) 0.0500(4) Uani d 1 . .
H H7 1.2174 0.6788 0.5256 0.075 Uiso calc 1 . .
O O8 1.1452(2) 0.56090(9) 0.35227(14) 0.0516(4) Uani d 1 . .
C C1 0.3454(2) 0.47588(13) 0.15565(17) 0.0357(4) Uani d 1 . .
C C2 0.4861(2) 0.53054(11) 0.14972(16) 0.0292(4) Uani d 1 . .
C C3 0.6466(2) 0.51509(10) 0.17001(15) 0.0278(4) Uani d 1 . .
C C4 0.7387(2) 0.44240(11) 0.20821(17) 0.0319(4) Uani d 1 . .
C C5 0.6292(2) 0.64095(10) 0.11886(15) 0.0267(3) Uani d 1 . .
C C6 0.6667(2) 0.72430(11) 0.08298(16) 0.0285(4) Uani d 1 . .
C C7 0.5793(2) 0.75560(13) -0.01030(17) 0.0372(4) Uani d 1 . .
H H7A 0.5006 0.7237 -0.0471 0.045 Uiso calc 1 . .
C C8 0.6074(3) 0.83341(14) -0.04936(19) 0.0443(5) Uani d 1 . .
H H8A 0.5480 0.8532 -0.1120 0.053 Uiso calc 1 . .
C C9 0.7227(3) 0.88147(13) 0.00409(19) 0.0441(5) Uani d 1 . .
H H9A 0.7415 0.9336 -0.0223 0.053 Uiso calc 1 . .
C C10 0.8105(2) 0.85196(12) 0.09733(17) 0.0364(4) Uani d 1 . .
H H10A 0.8877 0.8849 0.1337 0.044 Uiso calc 1 . .
C C11 0.7854(2) 0.77349(10) 0.13806(15) 0.0277(4) Uani d 1 . .
C C12 0.8843(2) 0.75027(10) 0.23927(15) 0.0268(4) Uani d 1 . .
C C13 1.0855(2) 0.81509(12) 0.50117(16) 0.0339(4) Uani d 1 . .
C C14 1.0233(2) 0.77016(11) 0.40019(16) 0.0295(4) Uani d 1 . .
C C15 1.0542(2) 0.69432(11) 0.35922(16) 0.0289(4) Uani d 1 . .
C C16 1.1485(2) 0.62510(12) 0.40453(17) 0.0370(4) Uani d 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'
Mn Mn 0.3368 0.7283 '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
_geom_angle_publ_flag
O1 Mn1 O5 1_655 4_575 83.09(7) y
O1 Mn1 O4 1_655 . 92.30(6) y
O5 Mn1 O4 4_575 . 129.79(6) y
O1 Mn1 N3 1_655 . 131.34(6) y
O5 Mn1 N3 4_575 . 90.99(6) y
O4 Mn1 N3 . . 126.00(6) y
O1 Mn1 N2 1_655 . 148.40(6) y
O5 Mn1 N2 4_575 . 84.75(6) y
O4 Mn1 N2 . . 73.60(5) y
N3 Mn1 N2 . . 77.81(5) y
O1 Mn1 O8 1_655 . 80.07(6) y
O5 Mn1 O8 4_575 . 138.39(6) y
O4 Mn1 O8 . . 88.81(6) y
N3 Mn1 O8 . . 72.95(5) y
N2 Mn1 O8 . . 126.47(6) y
C5 N1 C2 . . 108.33(14) ?
C5 N1 H1A . . 125.8 ?
C2 N1 H1A . . 125.8 ?
C5 N2 C3 . . 106.67(14) ?
C5 N2 Mn1 . . 140.76(12) ?
C3 N2 Mn1 . . 112.57(11) ?
C12 N3 C15 . . 106.34(14) ?
C12 N3 Mn1 . . 138.32(12) ?
C15 N3 Mn1 . . 115.34(11) ?
C12 N4 C14 . . 108.95(15) ?
C12 N4 H4A . . 125.5 ?
C14 N4 H4A . . 125.5 ?
C1 O1 Mn1 . 1_455 151.27(16) ?
C4 O3 H3 . . 109.5 ?
C4 O4 Mn1 . . 118.96(12) ?
C13 O5 Mn1 . 4_576 125.81(13) ?
C16 O7 H7 . . 109.5 ?
C16 O8 Mn1 . . 115.36(13) ?
O1 C1 O2 . . 124.28(19) ?
O1 C1 C2 . . 119.18(19) ?
O2 C1 C2 . . 116.51(17) ?
C3 C2 N1 . . 105.23(15) ?
C3 C2 C1 . . 130.33(17) ?
N1 C2 C1 . . 124.42(16) ?
N2 C3 C2 . . 109.91(15) ?
N2 C3 C4 . . 116.50(15) ?
C2 C3 C4 . . 133.59(16) ?
O4 C4 O3 . . 122.63(17) ?
O4 C4 C3 . . 118.04(16) ?
O3 C4 C3 . . 119.34(17) ?
N2 C5 N1 . . 109.86(15) ?
N2 C5 C6 . . 126.68(15) ?
N1 C5 C6 . . 123.36(15) ?
C7 C6 C11 . . 118.75(17) ?
C7 C6 C5 . . 117.65(16) ?
C11 C6 C5 . . 123.60(16) ?
C8 C7 C6 . . 121.16(19) ?
C8 C7 H7A . . 119.4 ?
C6 C7 H7A . . 119.4 ?
C9 C8 C7 . . 120.25(19) ?
C9 C8 H8A . . 119.9 ?
C7 C8 H8A . . 119.9 ?
C8 C9 C10 . . 119.70(19) ?
C8 C9 H9A . . 120.1 ?
C10 C9 H9A . . 120.1 ?
C9 C10 C11 . . 121.24(19) ?
C9 C10 H10A . . 119.4 ?
C11 C10 H10A . . 119.4 ?
C10 C11 C6 . . 118.89(17) ?
C10 C11 C12 . . 115.76(16) ?
C6 C11 C12 . . 125.32(16) ?
N3 C12 N4 . . 109.57(15) ?
N3 C12 C11 . . 128.97(16) ?
N4 C12 C11 . . 121.12(15) ?
O5 C13 O6 . . 126.74(18) ?
O5 C13 C14 . . 115.65(18) ?
O6 C13 C14 . . 117.61(17) ?
N4 C14 C15 . . 105.38(16) ?
N4 C14 C13 . . 121.80(16) ?
C15 C14 C13 . . 132.80(18) ?
C14 C15 N3 . . 109.75(16) ?
C14 C15 C16 . . 133.11(17) ?
N3 C15 C16 . . 116.97(16) ?
O8 C16 O7 . . 121.70(18) ?
O8 C16 C15 . . 119.05(17) ?
O7 C16 C15 . . 119.24(18) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Mn1 O1 1_655 2.1049(15) y
Mn1 O5 4_575 2.1128(14) y
Mn1 O4 . 2.1979(13) y
Mn1 N3 . 2.1982(15) y
Mn1 N2 . 2.2654(14) y
Mn1 O8 . 2.3225(16) y
N1 C5 . 1.360(2) ?
N1 C2 . 1.372(2) ?
N1 H1A . 0.8600 ?
N2 C5 . 1.325(2) ?
N2 C3 . 1.368(2) ?
N3 C12 . 1.330(2) ?
N3 C15 . 1.369(2) ?
N4 C12 . 1.353(2) ?
N4 C14 . 1.358(2) ?
N4 H4A . 0.8600 ?
O1 C1 . 1.229(2) ?
O1 Mn1 1_455 2.1049(15) ?
O2 C1 . 1.263(3) ?
O3 C4 . 1.286(2) ?
O3 H3 . 0.8200 ?
O4 C4 . 1.235(2) ?
O5 C13 . 1.248(2) ?
O5 Mn1 4_576 2.1128(14) ?
O6 C13 . 1.262(2) ?
O7 C16 . 1.305(2) ?
O7 H7 . 0.8200 ?
O8 C16 . 1.225(2) ?
C1 C2 . 1.484(2) ?
C2 C3 . 1.372(2) ?
C3 C4 . 1.479(2) ?
C5 C6 . 1.474(2) ?
C6 C7 . 1.392(3) ?
C6 C11 . 1.412(2) ?
C7 C8 . 1.386(3) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.374(3) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.382(3) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.398(3) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.471(2) ?
C13 C14 . 1.479(3) ?
C14 C15 . 1.369(2) ?
C15 C16 . 1.469(3) ?
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
O3 H3 O2 . 0.82 1.67 2.480(2) 172
O7 H7 O6 . 0.82 1.78 2.594(2) 170
N1 H1A O6 4_475 0.86 2.08 2.937(2) 172
N4 H4A O2 2_655 0.86 2.23 2.913(2) 136
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_1
_geom_torsion
Mn1 O1 C1 O2 1_455 96.8(4)
Mn1 O1 C1 C2 1_455 -85.4(4)
C5 N1 C2 C3 . 0.3(2)
C5 N1 C2 C1 . -178.19(17)
O1 C1 C2 C3 . -179.6(2)
O2 C1 C2 C3 . -1.6(3)
O1 C1 C2 N1 . -1.5(3)
O2 C1 C2 N1 . 176.52(18)
C5 N2 C3 C2 . 0.4(2)
Mn1 N2 C3 C2 . -179.20(12)
C5 N2 C3 C4 . -179.12(16)
Mn1 N2 C3 C4 . 1.3(2)
N1 C2 C3 N2 . -0.4(2)
C1 C2 C3 N2 . 177.96(19)
N1 C2 C3 C4 . 179.0(2)
C1 C2 C3 C4 . -2.7(4)
Mn1 O4 C4 O3 . 173.51(16)
Mn1 O4 C4 C3 . -6.4(2)
N2 C3 C4 O4 . 3.2(3)
C2 C3 C4 O4 . -176.1(2)
N2 C3 C4 O3 . -176.66(18)
C2 C3 C4 O3 . 4.0(3)
C3 N2 C5 N1 . -0.2(2)
Mn1 N2 C5 N1 . 179.20(14)
C3 N2 C5 C6 . -176.61(17)
Mn1 N2 C5 C6 . 2.8(3)
C2 N1 C5 N2 . -0.1(2)
C2 N1 C5 C6 . 176.50(17)
N2 C5 C6 C7 . 136.9(2)
N1 C5 C6 C7 . -39.1(3)
N2 C5 C6 C11 . -43.2(3)
N1 C5 C6 C11 . 140.84(18)
C11 C6 C7 C8 . 0.2(3)
C5 C6 C7 C8 . -179.94(19)
C6 C7 C8 C9 . -0.2(3)
C7 C8 C9 C10 . -0.1(3)
C8 C9 C10 C11 . 0.6(3)
C9 C10 C11 C6 . -0.7(3)
C9 C10 C11 C12 . -178.72(19)
C7 C6 C11 C10 . 0.3(3)
C5 C6 C11 C10 . -179.61(17)
C7 C6 C11 C12 . 178.13(18)
C5 C6 C11 C12 . -1.8(3)
C15 N3 C12 N4 . -0.4(2)
Mn1 N3 C12 N4 . 179.42(13)
C15 N3 C12 C11 . 172.85(17)
Mn1 N3 C12 C11 . -7.3(3)
C14 N4 C12 N3 . 0.9(2)
C14 N4 C12 C11 . -172.96(16)
C10 C11 C12 N3 . -132.8(2)
C6 C11 C12 N3 . 49.3(3)
C10 C11 C12 N4 . 39.8(2)
C6 C11 C12 N4 . -138.15(18)
Mn1 O5 C13 O6 4_576 -26.7(3)
Mn1 O5 C13 C14 4_576 153.52(14)
C12 N4 C14 C15 . -1.0(2)
C12 N4 C14 C13 . 177.94(16)
O5 C13 C14 N4 . 9.3(3)
O6 C13 C14 N4 . -170.52(17)
O5 C13 C14 C15 . -172.1(2)
O6 C13 C14 C15 . 8.1(3)
N4 C14 C15 N3 . 0.8(2)
C13 C14 C15 N3 . -178.01(19)
N4 C14 C15 C16 . -174.1(2)
C13 C14 C15 C16 . 7.1(4)
C12 N3 C15 C14 . -0.3(2)
Mn1 N3 C15 C14 . 179.88(12)
C12 N3 C15 C16 . 175.60(16)
Mn1 N3 C15 C16 . -4.3(2)
Mn1 O8 C16 O7 . -176.34(16)
Mn1 O8 C16 C15 . 4.6(3)
C14 C15 C16 O8 . 174.3(2)
N3 C15 C16 O8 . -0.4(3)
C14 C15 C16 O7 . -4.8(3)
N3 C15 C16 O7 . -179.49(18)

_cod_database_fobs_code 2021088
