#------------------------------------------------------------------------------
#$Date: 2022-12-05 11:59:06 +0200 (Mon, 05 Dec 2022) $
#$Revision: 279692 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/63/8106316.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_8106316
loop_
_publ_author_name
'Guang-Zhen, Liu'
'Meng-Zhen, Yan'
_publ_section_title
;
 Hydrothemal synthesis and crystal structure of
 triaqua-bis(5-carboxy-1-methyl-1H-imidazole-4-carboxylato-κ2
 N,O;κ1O)manganese(II), C12H16N4O11Mn
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              835
_journal_page_last               836
_journal_paper_doi               10.1515/ncrs-2018-0043
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C12 H16 Mn N4 O11'
_chemical_formula_sum            'C12 H16 Mn N4 O11'
_chemical_formula_weight         447.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                104.288(3)
_cell_angle_beta                 94.024(3)
_cell_angle_gamma                97.365(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7186(3)
_cell_length_b                   9.8439(3)
_cell_length_c                   11.6084(3)
_cell_measurement_reflns_used    8635
_cell_measurement_temperature    291.03(10)
_cell_measurement_theta_max      26.4510
_cell_measurement_theta_min      4.2350
_cell_volume                     842.91(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.03(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -20.00  29.00   1.00    3.00    --   -9.62 -99.00-150.00   49
  2  ω    -79.00   9.00   1.00    3.00    --   -9.62 -38.00 -90.00   88
  3  ω    -36.00  58.00   1.00    3.00    --   -9.62  77.00  60.00   94
  4  ω    -19.00  82.00   1.00    3.00    --   10.64  19.00-120.00  101
  5  ω    -20.00  50.00   1.00    3.00    --   10.64 -99.00  30.00   70
  6  ω     -6.00  78.00   1.00    3.00    --   10.64  57.00  90.00   84
  7  ω    -20.00  50.00   1.00    3.00    --   10.64 -99.00-150.00   70
  8  ω    -20.00  50.00   1.00    3.00    --   10.64 -99.00 120.00   70
  9  ω     -6.00  78.00   1.00    3.00    --   10.64  57.00  30.00   84
 10  ω    -56.00  34.00   1.00    3.00    --   10.64 -71.00 -91.00   90
 11  ω    -77.00 -29.00   1.00    3.00    --   -9.62 -77.00 150.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0082564000
_diffrn_orient_matrix_UB_12      0.0352246000
_diffrn_orient_matrix_UB_13      -0.0460969000
_diffrn_orient_matrix_UB_21      -0.0766007000
_diffrn_orient_matrix_UB_22      0.0246569000
_diffrn_orient_matrix_UB_23      0.0223610000
_diffrn_orient_matrix_UB_31      0.0524147000
_diffrn_orient_matrix_UB_32      0.0617089000
_diffrn_orient_matrix_UB_33      0.0373603000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14394
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.393
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.855
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_description       block
_exptl_crystal_F_000             458
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         2880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0322
_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)+(0.0383P)²+0.5684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2709
_reflns_number_total             2880
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0043_suppl.cif
_cod_data_source_block           lgz
_cod_original_cell_volume        842.93(5)
_cod_database_code               8106316
_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.
;
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     23.21
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Rotating group:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB), O3W(H3WA,H3WB)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C11(H11A,H11B,H11C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O7(H7)
;
_olex2_date_sample_data_collection 2017-09-20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.314
_oxdiff_exptl_absorpt_empirical_full_min 0.590
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.77286(4) 0.58068(3) 0.66268(3) 0.02699(13) Uani 1 1 d . . . . .
O1 O 0.48902(19) 0.56463(16) 0.69480(13) 0.0313(4) Uani 1 1 d . . . . .
O1W O 1.0479(2) 0.58940(18) 0.64937(15) 0.0400(4) Uani 1 1 d . . . . .
H1WA H 1.0690 0.5886 0.5779 0.060 Uiso 1 1 d GR . . . .
H1WB H 1.0812 0.5135 0.6602 0.060 Uiso 1 1 d GR . . . .
O3 O 0.2524(2) 0.32374(18) 0.92858(15) 0.0367(4) Uani 1 1 d . . . . .
H3 H 0.2641 0.3726 0.8810 0.055 Uiso 1 1 calc GR . . . .
O2W O 0.8310(2) 0.76948(17) 0.81111(15) 0.0442(4) Uani 1 1 d . . . . .
H2WA H 0.7394 0.7823 0.8469 0.066 Uiso 1 1 d GR . . . .
H2WB H 0.8530 0.8425 0.7844 0.066 Uiso 1 1 d GR . . . .
O4 O 0.4184(2) 0.21081(18) 1.02283(15) 0.0412(4) Uani 1 1 d . . . . .
O3W O 0.6959(2) 0.38549(16) 0.51154(13) 0.0323(4) Uani 1 1 d . . . . .
H3WA H 0.6204 0.3995 0.4558 0.048 Uiso 1 1 d GR . . . .
H3WB H 0.6351 0.3171 0.5357 0.048 Uiso 1 1 d GR . . . .
O5 O 0.7062(3) 0.69583(19) 0.53944(16) 0.0488(5) Uani 1 1 d . . . . .
O2 O 0.27823(19) 0.47657(17) 0.78836(14) 0.0361(4) Uani 1 1 d . . . . .
O6 O 0.9500(2) 0.7691(2) 0.46879(18) 0.0502(5) Uani 1 1 d . . . . .
O7 O 1.0381(2) 0.9113(2) 0.33200(19) 0.0545(5) Uani 1 1 d . . . . .
H7 H 1.0039 0.8596 0.3740 0.082 Uiso 1 1 calc GR . . . .
O8 O 0.9176(3) 1.0317(2) 0.21897(17) 0.0541(5) Uani 1 1 d . . . . .
N1 N 0.7366(2) 0.44486(18) 0.79222(15) 0.0254(4) Uani 1 1 d . . . . .
N2 N 0.7219(2) 0.30659(19) 0.91609(15) 0.0277(4) Uani 1 1 d . . . . .
N3 N 0.5053(2) 0.83313(18) 0.41636(15) 0.0273(4) Uani 1 1 d . . . . .
N4 N 0.5862(2) 0.97669(17) 0.30359(15) 0.0260(4) Uani 1 1 d . . . . .
C00I C 0.5676(3) 0.4253(2) 0.82085(17) 0.0217(4) Uani 1 1 d . . . . .
C1 C 0.4356(3) 0.4940(2) 0.76408(18) 0.0248(5) Uani 1 1 d . . . . .
C2 C 0.8237(3) 0.3718(2) 0.8507(2) 0.0302(5) Uani 1 1 d . . . . .
H2 H 0.9426 0.3659 0.8471 0.036 Uiso 1 1 calc R . . . .
C3 C 0.5547(3) 0.3395(2) 0.89804(17) 0.0230(4) Uani 1 1 d . . . . .
C4 C 0.7874(3) 0.2182(3) 0.9899(2) 0.0456(6) Uani 1 1 d . . . . .
H4A H 0.9089 0.2122 0.9799 0.068 Uiso 1 1 calc GR . . . .
H4B H 0.7203 0.1249 0.9655 0.068 Uiso 1 1 calc GR . . . .
H4C H 0.7758 0.2600 1.0724 0.068 Uiso 1 1 calc GR . . . .
C5 C 0.4030(3) 0.2856(2) 0.95499(18) 0.0274(5) Uani 1 1 d . . . . .
C6 C 0.7866(3) 0.7626(2) 0.4770(2) 0.0330(5) Uani 1 1 d . . . . .
C7 C 0.6822(3) 0.8401(2) 0.40923(18) 0.0233(4) Uani 1 1 d . . . . .
C8 C 0.4534(3) 0.9170(2) 0.35272(19) 0.0283(5) Uani 1 1 d . . . . .
H8 H 0.3379 0.9332 0.3428 0.034 Uiso 1 1 calc R . . . .
C9 C 0.7360(3) 0.9280(2) 0.33806(17) 0.0243(4) Uani 1 1 d . . . . .
C10 C 0.9066(3) 0.9620(2) 0.2921(2) 0.0357(5) Uani 1 1 d . . . . .
C11 C 0.5663(4) 1.0811(3) 0.2346(2) 0.0472(7) Uani 1 1 d . . . . .
H11A H 0.5850 1.0414 0.1530 0.071 Uiso 1 1 calc GR . . . .
H11B H 0.6509 1.1645 0.2680 0.071 Uiso 1 1 calc GR . . . .
H11C H 0.4499 1.1056 0.2377 0.071 Uiso 1 1 calc GR . . . .
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
O1 Mn1 O3W 87.10(6) . .
O1 Mn1 N1 73.63(6) . .
O1W Mn1 O1 173.89(6) . .
O1W Mn1 O2W 88.54(7) . .
O1W Mn1 O3W 94.89(6) . .
O1W Mn1 N1 100.60(6) . .
O2W Mn1 O1 89.46(6) . .
O2W Mn1 O3W 176.56(6) . .
O2W Mn1 N1 90.12(6) . .
O3W Mn1 N1 89.00(6) . .
O5 Mn1 O1 85.68(7) . .
O5 Mn1 O1W 100.19(7) . .
O5 Mn1 O2W 93.13(7) . .
O5 Mn1 O3W 86.52(6) . .
O5 Mn1 N1 159.03(7) . .
C1 O1 Mn1 118.71(13) . .
Mn1 O1W H1WA 109.8 . .
Mn1 O1W H1WB 109.8 . .
H1WA O1W H1WB 104.2 . .
C5 O3 H3 109.5 . .
Mn1 O2W H2WA 109.6 . .
Mn1 O2W H2WB 109.6 . .
H2WA O2W H2WB 104.4 . .
Mn1 O3W H3WA 111.8 . .
Mn1 O3W H3WB 111.0 . .
H3WA O3W H3WB 102.5 . .
C6 O5 Mn1 136.26(17) . .
C10 O7 H7 109.5 . .
C00I N1 Mn1 113.21(12) . .
C2 N1 Mn1 141.38(14) . .
C2 N1 C00I 105.39(17) . .
C2 N2 C3 106.79(17) . .
C2 N2 C4 123.32(19) . .
C3 N2 C4 129.88(18) . .
C8 N3 C7 105.19(17) . .
C8 N4 C9 107.02(17) . .
C8 N4 C11 123.58(19) . .
C9 N4 C11 129.27(19) . .
N1 C00I C1 117.47(17) . .
N1 C00I C3 109.97(17) . .
C3 C00I C1 132.54(19) . .
O1 C1 O2 124.34(19) . .
O1 C1 C00I 116.99(18) . .
O2 C1 C00I 118.66(18) . .
N1 C2 N2 112.52(18) . .
N1 C2 H2 123.7 . .
N2 C2 H2 123.7 . .
N2 C3 C5 123.10(18) . .
C00I C3 N2 105.32(17) . .
C00I C3 C5 131.58(19) . .
N2 C4 H4A 109.5 . .
N2 C4 H4B 109.5 . .
N2 C4 H4C 109.5 . .
H4A C4 H4B 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
O3 C5 C3 116.42(19) . .
O4 C5 O3 121.7(2) . .
O4 C5 C3 121.8(2) . .
O5 C6 O6 124.0(2) . .
O5 C6 C7 117.0(2) . .
O6 C6 C7 119.1(2) . .
N3 C7 C6 119.74(19) . .
N3 C7 C9 110.20(17) . .
C9 C7 C6 130.0(2) . .
N3 C8 N4 112.52(19) . .
N3 C8 H8 123.7 . .
N4 C8 H8 123.7 . .
N4 C9 C7 105.06(17) . .
N4 C9 C10 122.21(18) . .
C7 C9 C10 132.52(19) . .
O7 C10 C9 116.4(2) . .
O8 C10 O7 123.1(2) . .
O8 C10 C9 120.5(2) . .
N4 C11 H11A 109.5 . .
N4 C11 H11B 109.5 . .
N4 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 O1 2.2403(15) .
Mn1 O1W 2.1314(16) .
Mn1 O2W 2.1729(16) .
Mn1 O3W 2.2406(15) .
Mn1 O5 2.1078(16) .
Mn1 N1 2.2545(17) .
O1 C1 1.244(3) .
O1W H1WA 0.8551 .
O1W H1WB 0.8550 .
O3 H3 0.8200 .
O3 C5 1.306(3) .
O2W H2WA 0.8529 .
O2W H2WB 0.8530 .
O4 C5 1.213(3) .
O3W H3WA 0.8874 .
O3W H3WB 0.8849 .
O5 C6 1.239(3) .
O2 C1 1.266(3) .
O6 C6 1.266(3) .
O7 H7 0.8200 .
O7 C10 1.293(3) .
O8 C10 1.217(3) .
N1 C00I 1.370(3) .
N1 C2 1.315(3) .
N2 C2 1.342(3) .
N2 C3 1.385(3) .
N2 C4 1.471(3) .
N3 C7 1.368(3) .
N3 C8 1.316(3) .
N4 C8 1.347(3) .
N4 C9 1.378(3) .
N4 C11 1.466(3) .
C00I C1 1.495(3) .
C00I C3 1.375(3) .
C2 H2 0.9300 .
C3 C5 1.487(3) .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C6 C7 1.488(3) .
C7 C9 1.383(3) .
C8 H8 0.9300 .
C9 C10 1.485(3) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
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
O1W H1WA O3W 0.86 2.17 2.843(2) 135.3 2_766
O1W H1WA O6 0.86 2.64 3.169(2) 121.2 .
O1W H1WB O2 0.86 2.18 2.826(2) 132.2 1_655
O3 H3 O2 0.82 1.66 2.476(2) 176.5 .
O2W H2WA O4 0.85 2.00 2.809(2) 157.9 2_667
O2W H2WB O8 0.85 2.04 2.679(2) 131.6 2_776
O3W H3WA O1 0.89 2.02 2.880(2) 163.7 2_666
O3W H3WA O5 0.89 2.58 3.081(2) 116.3 2_666
O3W H3WB N3 0.88 1.94 2.821(2) 177.8 2_666
O7 H7 O6 0.82 1.62 2.439(3) 173.9 .
