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#$Date: 2023-05-12 10:46:04 +0300 (Fri, 12 May 2023) $
#$Revision: 283715 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/71/8107186.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_8107186
loop_
_publ_author_name
'Hong, Dong-Feng'
'Chen, Ye'
'Zhu, Wen-Li'
_publ_section_title
;
 The crystal structure of bis(pyrazolo[1,5-a]pyrimidine-3-carboxylato-κ 2
 N,O)-copper(ii), C14H8N6O4Cu
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              679
_journal_page_last               680
_journal_paper_doi               10.1515/ncrs-2022-0178
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C14 H8 Cu N6 O4'
_chemical_formula_sum            'C14 H8 Cu N6 O4'
_chemical_formula_weight         387.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 108.550(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6054(8)
_cell_length_b                   7.0441(3)
_cell_length_c                   12.6301(6)
_cell_measurement_reflns_used    3500
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9440
_cell_measurement_theta_min      4.3270
_cell_volume                     1316.25(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -83.00   3.00   1.00    2.00    --  -15.84 -38.00 120.00   86
  2  ω    -35.00  53.00   1.00    2.00    --  -15.84  38.00 -60.00   88
  3  ω    -69.00  -6.00   1.00    2.00    --  -15.84 124.00 166.25   63
  4  ω    -11.00  82.00   1.00    2.00    --   17.09  19.00 -30.00   93
  5  ω     18.00  86.00   1.00    2.00    --   17.09  38.00  60.00   68
  6  ω     -8.00  37.00   1.00    2.00    --   17.09  77.00 -90.00   45
  7  ω     -6.00  56.00   1.00    2.00    --   17.09 -99.00 150.00   62
  8  ω    -10.00  15.00   1.00    2.00    --   17.09  77.00 120.00   25
;
_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      -0.0149193000
_diffrn_orient_matrix_UB_12      -0.0921498000
_diffrn_orient_matrix_UB_13      0.0084780000
_diffrn_orient_matrix_UB_21      0.0392781000
_diffrn_orient_matrix_UB_22      -0.0397627000
_diffrn_orient_matrix_UB_23      -0.0079514000
_diffrn_orient_matrix_UB_31      0.0231194000
_diffrn_orient_matrix_UB_32      0.0080308000
_diffrn_orient_matrix_UB_33      0.0580763000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7521
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.361
_diffrn_reflns_theta_min         3.403
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.957
_exptl_crystal_description       block
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0317
_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)+(0.0304P)²+2.0704P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0778
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1460
_reflns_number_total             1631
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0178_suppl.cif
_cod_data_source_block           hdf20
_cod_original_cell_volume        1316.24(11)
_cod_database_code               8107186
_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   0.630
_shelx_estimated_absorpt_t_min   0.588
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7)
;
_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 1.204
_oxdiff_exptl_absorpt_empirical_full_min 0.776
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.21781(5) 0.7500 0.01938(13) Uani 1 2 d S T P . .
O1 O 0.40439(10) 0.1527(2) 0.61711(12) 0.0247(3) Uani 1 1 d . . . . .
O2 O 0.33477(10) 0.0902(2) 0.43799(13) 0.0280(4) Uani 1 1 d . . . . .
N1 N 0.59021(12) 0.2811(3) 0.67478(14) 0.0189(4) Uani 1 1 d . . . . .
N2 N 0.61305(12) 0.3513(3) 0.50131(14) 0.0199(4) Uani 1 1 d . . . . .
N3 N 0.56928(13) 0.3449(3) 0.38898(15) 0.0262(4) Uani 1 1 d . . . . .
C1 C 0.39972(14) 0.1533(3) 0.51255(17) 0.0187(4) Uani 1 1 d . . . . .
C2 C 0.47766(14) 0.2343(3) 0.48592(17) 0.0181(4) Uani 1 1 d . . . . .
C3 C 0.48836(16) 0.2733(3) 0.38201(18) 0.0234(5) Uani 1 1 d . . . . .
H3 H 0.4433 0.2514 0.3144 0.028 Uiso 1 1 calc R . . . .
C4 C 0.55932(14) 0.2860(3) 0.56175(17) 0.0172(4) Uani 1 1 d . . . . .
C5 C 0.69864(14) 0.4136(3) 0.55167(19) 0.0243(5) Uani 1 1 d . . . . .
H5 H 0.7340 0.4599 0.5105 0.029 Uiso 1 1 calc R . . . .
C6 C 0.73036(15) 0.4054(3) 0.6652(2) 0.0276(5) Uani 1 1 d . . . . .
H6 H 0.7891 0.4438 0.7032 0.033 Uiso 1 1 calc R . . . .
C7 C 0.67439(15) 0.3389(3) 0.72479(18) 0.0239(5) Uani 1 1 d . . . . .
H7 H 0.6971 0.3351 0.8023 0.029 Uiso 1 1 calc R . . . .
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 152.28(11) . 2_656
O1 Cu1 N1 89.99(7) 2_656 .
O1 Cu1 N1 96.20(7) . .
O1 Cu1 N1 96.20(7) 2_656 2_656
O1 Cu1 N1 89.99(7) . 2_656
N1 Cu1 N1 154.01(11) 2_656 .
C1 O1 Cu1 131.82(14) . .
C4 N1 Cu1 116.22(14) . .
C7 N1 Cu1 125.92(15) . .
C7 N1 C4 117.40(19) . .
N3 N2 C4 111.87(17) . .
C5 N2 N3 126.17(18) . .
C5 N2 C4 121.96(18) . .
C3 N3 N2 103.34(17) . .
O1 C1 C2 116.69(18) . .
O2 C1 O1 123.0(2) . .
O2 C1 C2 120.31(19) . .
C3 C2 C1 129.9(2) . .
C4 C2 C1 126.23(19) . .
C4 C2 C3 103.87(19) . .
N3 C3 C2 113.8(2) . .
N3 C3 H3 123.1 . .
C2 C3 H3 123.1 . .
N1 C4 N2 121.09(18) . .
N1 C4 C2 131.8(2) . .
C2 C4 N2 107.10(18) . .
N2 C5 H5 121.5 . .
N2 C5 C6 117.0(2) . .
C6 C5 H5 121.5 . .
C5 C6 H6 120.0 . .
C5 C6 C7 120.0(2) . .
C7 C6 H6 120.0 . .
N1 C7 C6 122.5(2) . .
N1 C7 H7 118.7 . .
C6 C7 H7 118.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.9131(14) .
Cu1 O1 1.9131(14) 2_656
Cu1 N1 1.9835(18) 2_656
Cu1 N1 1.9835(18) .
O1 C1 1.299(2) .
O2 C1 1.227(3) .
N1 C4 1.354(3) .
N1 C7 1.328(3) .
N2 N3 1.366(2) .
N2 C4 1.380(3) .
N2 C5 1.357(3) .
N3 C3 1.337(3) .
C1 C2 1.476(3) .
C2 C3 1.402(3) .
C2 C4 1.378(3) .
C3 H3 0.9300 .
C5 H5 0.9300 .
C5 C6 1.361(3) .
C6 H6 0.9300 .
C6 C7 1.403(3) .
C7 H7 0.9300 .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
Cu1 O1 C1 O2 173.19(16) . . . .
Cu1 O1 C1 C2 -6.6(3) . . . .
Cu1 N1 C4 N2 171.82(15) . . . .
Cu1 N1 C4 C2 -8.4(3) . . . .
Cu1 N1 C7 C6 -171.19(17) . . . .
O1 C1 C2 C3 -172.3(2) . . . .
O1 C1 C2 C4 9.1(3) . . . .
O2 C1 C2 C3 7.9(4) . . . .
O2 C1 C2 C4 -170.7(2) . . . .
N2 N3 C3 C2 0.5(3) . . . .
N2 C5 C6 C7 -1.5(3) . . . .
N3 N2 C4 N1 -179.89(19) . . . .
N3 N2 C4 C2 0.3(2) . . . .
N3 N2 C5 C6 -178.9(2) . . . .
C1 C2 C3 N3 -179.1(2) . . . .
C1 C2 C4 N1 -0.9(4) . . . .
C1 C2 C4 N2 178.89(19) . . . .
C3 C2 C4 N1 -179.8(2) . . . .
C3 C2 C4 N2 0.0(2) . . . .
C4 N1 C7 C6 0.8(3) . . . .
C4 N2 N3 C3 -0.5(2) . . . .
C4 N2 C5 C6 1.4(3) . . . .
C4 C2 C3 N3 -0.3(3) . . . .
C5 N2 N3 C3 179.8(2) . . . .
C5 N2 C4 N1 -0.1(3) . . . .
C5 N2 C4 C2 -179.95(19) . . . .
C5 C6 C7 N1 0.4(4) . . . .
C7 N1 C4 N2 -0.9(3) . . . .
C7 N1 C4 C2 178.8(2) . . . .
