#------------------------------------------------------------------------------
#$Date: 2022-06-08 11:27:48 +0300 (Wed, 08 Jun 2022) $
#$Revision: 275907 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/53/8105361.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_8105361
loop_
_publ_author_name
'Du, Xigang'
'Wang, Chunwei'
_publ_section_title
;
 Crystal structure of bis(6-aminopyridine-2-carboxylato-κ2
 O,N)-copper(II), C12H10O6N4Cu
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1007
_journal_page_last               1008
_journal_paper_doi               10.1515/ncrs-2020-0041
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C12 H10 Cu N4 O4'
_chemical_formula_sum            'C12 H10 Cu N4 O4'
_chemical_formula_weight         337.78
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 91.060(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.7015(2)
_cell_length_b                   7.3920(4)
_cell_length_c                   21.3535(12)
_cell_measurement_reflns_used    2417
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.7200
_cell_measurement_theta_min      3.9560
_cell_volume                     584.16(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_temperature      293.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -81.00   2.00   1.00   16.56    --  -13.80 -57.00  60.00   83
  2  ω     -2.00  24.00   1.00   16.56    --  -13.80 -99.00 120.00   26
  3  ω    -41.00  31.00   1.00   16.56    --  -13.80  77.00 -60.00   72
  4  ω    -81.00 -31.00   1.00   16.56    --  -13.80 -57.00   0.00   50
  5  ω    -81.00  14.00   1.00   16.56    --  -13.80 -19.00 120.00   95
  6  ω     -5.00  54.00   1.00   16.56    --   14.82 -99.00  60.00   59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1808896000
_diffrn_orient_matrix_UB_12      -0.0112102000
_diffrn_orient_matrix_UB_13      0.0096243000
_diffrn_orient_matrix_UB_21      0.0464142000
_diffrn_orient_matrix_UB_22      0.0375922000
_diffrn_orient_matrix_UB_23      0.0296519000
_diffrn_orient_matrix_UB_31      -0.0429152000
_diffrn_orient_matrix_UB_32      0.0875758000
_diffrn_orient_matrix_UB_33      -0.0115038000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4327
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         3.352
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.894
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.920
_exptl_crystal_description       block
_exptl_crystal_F_000             342
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         1086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0319
_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)+(0.0290P)²+0.7540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0769
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1016
_reflns_number_total             1086
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0041_suppl.cif
_cod_data_source_block           20195198
_cod_database_code               8105361
_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_max   0.681
_shelx_estimated_absorpt_t_min   0.600
_reflns_odcompleteness_completeness 99.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
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_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
Cu1 Cu 0.5000 0.5000 0.5000 0.02190(18) Uani 1 2 d S T P . .
O1 O 0.8102(6) 0.6781(3) 0.53906(9) 0.0308(5) Uani 1 1 d . . . . .
O2 O 1.0079(6) 0.7760(3) 0.63203(9) 0.0312(5) Uani 1 1 d . . . . .
N1 N 0.5479(6) 0.3779(3) 0.58390(10) 0.0166(5) Uani 1 1 d . . . . .
N2 N 0.2922(7) 0.0955(3) 0.56337(11) 0.0273(6) Uani 1 1 d . . . . .
H2A H 0.2599 0.1255 0.5248 0.033 Uiso 1 1 calc R . . . .
H2B H 0.2266 -0.0097 0.5761 0.033 Uiso 1 1 calc R . . . .
C1 C 0.8531(7) 0.6635(3) 0.59926(12) 0.0201(6) Uani 1 1 d . . . . .
C2 C 0.7119(7) 0.4909(3) 0.62650(12) 0.0167(5) Uani 1 1 d . . . . .
C3 C 0.7606(7) 0.4500(4) 0.68811(12) 0.0200(6) Uani 1 1 d . . . . .
H3 H 0.8660 0.5328 0.7157 0.024 Uiso 1 1 calc R . . . .
C4 C 0.6477(7) 0.2795(4) 0.70897(12) 0.0214(6) Uani 1 1 d . . . . .
H4 H 0.6745 0.2479 0.7510 0.026 Uiso 1 1 calc R . . . .
C5 C 0.4991(7) 0.1610(4) 0.66742(12) 0.0216(6) Uani 1 1 d . . . . .
H5 H 0.4328 0.0460 0.6806 0.026 Uiso 1 1 calc R . . . .
C6 C 0.4444(7) 0.2123(3) 0.60363(12) 0.0173(5) 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'
Cu Cu 0.3201 1.2651 '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 Cu1 O1 180.0 . 3_666
O1 Cu1 N1 96.94(8) 3_666 .
O1 Cu1 N1 83.06(8) . .
O1 Cu1 N1 83.06(8) 3_666 3_666
O1 Cu1 N1 96.94(8) . 3_666
N1 Cu1 N1 180.0 . 3_666
C1 O1 Cu1 115.68(17) . .
C2 N1 Cu1 110.42(16) . .
C6 N1 Cu1 131.54(18) . .
C6 N1 C2 118.0(2) . .
H2A N2 H2B 120.0 . .
C6 N2 H2A 120.0 . .
C6 N2 H2B 120.0 . .
O1 C1 C2 114.7(2) . .
O2 C1 O1 124.0(2) . .
O2 C1 C2 121.3(2) . .
N1 C2 C1 114.5(2) . .
C3 C2 N1 123.9(2) . .
C3 C2 C1 121.6(2) . .
C2 C3 H3 120.9 . .
C2 C3 C4 118.2(2) . .
C4 C3 H3 120.9 . .
C3 C4 H4 120.3 . .
C5 C4 C3 119.5(2) . .
C5 C4 H4 120.3 . .
C4 C5 H5 119.9 . .
C4 C5 C6 120.2(2) . .
C6 C5 H5 119.9 . .
N1 C6 C5 120.2(2) . .
N2 C6 N1 120.2(2) . .
N2 C6 C5 119.6(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.9268(18) .
Cu1 O1 1.9268(18) 3_666
Cu1 N1 2.011(2) .
Cu1 N1 2.011(2) 3_666
O1 C1 1.297(3) .
O2 C1 1.222(3) .
N1 C2 1.369(3) .
N1 C6 1.352(3) .
N2 H2A 0.8600 .
N2 H2B 0.8600 .
N2 C6 1.336(3) .
C1 C2 1.501(4) .
C2 C3 1.359(4) .
C3 H3 0.9300 .
C3 C4 1.403(4) .
C4 H4 0.9300 .
C4 C5 1.356(4) .
C5 H5 0.9300 .
C5 C6 1.425(4) .
