#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/53/7235397.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_7235397
loop_
_publ_author_name
'Mirzaei, Masoud'
'Eshtiagh-Hosseini, Hossein'
'Bauzá, Antonio'
'Zarghami, Sara'
'Ballester, Pablo'
'Mague, Joel T.'
'Frontera, Antonio'
_publ_section_title
;
 On the importance of non covalent interactions in the structure of
 coordination Cu(ii) and Co(ii) complexes of pyrazine- and
 pyridine-dicarboxylic acid derivatives: experimental and theoretical
 views
;
_journal_issue                   27
_journal_name_full               CrystEngComm
_journal_page_first              6149
_journal_paper_doi               10.1039/C4CE00003J
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C14 H20 Cu2 N2 O15'
_chemical_formula_weight         583.40
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.111(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3425(5)
_cell_length_b                   27.1640(17)
_cell_length_c                   9.5946(6)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      39.26
_cell_measurement_theta_min      2.89
_cell_volume                     2152.5(2)
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            55047
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         39.61
_diffrn_reflns_theta_min         2.62
_diffrn_source                   'Rotating anode X-ray tube'
_diffrn_source_current           70
_diffrn_source_power             50
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_source_type              'Bruker-Nonius FR 591'
_exptl_absorpt_coefficient_mu    2.055
_exptl_absorpt_correction_T_max  0.5776
_exptl_absorpt_correction_T_min  0.5776
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.948
_refine_diff_density_min         -1.582
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         12365
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0580P)²+3.3794P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1253
_reflns_number_gt                11576
_reflns_number_total             12365
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00003j1.cif
_cod_data_source_block           mm2_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7235397
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.04305(16) 0.18274(5) 0.61970(14) 0.00863(18) Uani 1 1 d .
C2 C 0.14517(16) 0.21446(5) 0.53715(13) 0.00792(17) Uani 1 1 d .
C3 C 0.14553(18) 0.26565(5) 0.53184(16) 0.0113(2) Uani 1 1 d .
H3 H 0.0757 0.2845 0.5812 0.014 Uiso 1 1 calc R
C4 C 0.2514(2) 0.28852(5) 0.45196(17) 0.0132(2) Uani 1 1 d .
H4 H 0.2561 0.3234 0.4482 0.016 Uiso 1 1 calc R
C5 C 0.35040(19) 0.26041(5) 0.37757(16) 0.0122(2) Uani 1 1 d .
H5 H 0.4234 0.2756 0.3231 0.015 Uiso 1 1 calc R
C6 C 0.33884(16) 0.20946(5) 0.38571(14) 0.00840(18) Uani 1 1 d .
C7 C 0.42443(16) 0.17235(5) 0.30454(14) 0.00936(18) Uani 1 1 d .
C8 C 0.07968(15) 0.02993(5) 0.33602(13) 0.00729(17) Uani 1 1 d .
C9 C 0.19277(15) 0.00777(4) 0.45586(13) 0.00657(16) Uani 1 1 d .
C10 C 0.20587(16) -0.04202(5) 0.48902(14) 0.00827(18) Uani 1 1 d .
H10 H 0.1403 -0.0657 0.4349 0.010 Uiso 1 1 calc R
C11 C 0.31765(17) -0.05627(5) 0.60375(14) 0.00921(18) Uani 1 1 d .
H11 H 0.3269 -0.0899 0.6306 0.011 Uiso 1 1 calc R
C12 C 0.41582(16) -0.02099(5) 0.67900(14) 0.00894(18) Uani 1 1 d .
H12 H 0.4946 -0.0301 0.7560 0.011 Uiso 1 1 calc R
C13 C 0.39517(15) 0.02798(5) 0.63813(13) 0.00699(17) Uani 1 1 d .
C14 C 0.49544(15) 0.07036(5) 0.70465(13) 0.00741(17) Uani 1 1 d .
Cu1 Cu 0.76190(2) 0.100754(7) 0.944097(18) 0.00869(4) Uani 1 1 d .
Cu2 Cu 0.25007(2) 0.113957(6) 0.486452(19) 0.00883(4) Uani 1 1 d .
N1 N 0.24055(13) 0.18799(4) 0.46587(12) 0.00692(15) Uani 1 1 d .
N2 N 0.28419(13) 0.04148(4) 0.53113(11) 0.00639(15) Uani 1 1 d .
O1 O 0.06679(14) 0.13644(4) 0.61296(12) 0.01003(15) Uani 1 1 d .
O2 O -0.05329(15) 0.20294(4) 0.68958(14) 0.01398(19) Uani 1 1 d .
O3 O 0.38430(14) 0.12766(4) 0.31947(12) 0.01061(16) Uani 1 1 d .
O4 O 0.52122(15) 0.18763(5) 0.22667(13) 0.01511(19) Uani 1 1 d .
O5 O 0.08014(13) 0.07656(4) 0.32807(11) 0.00970(16) Uani 1 1 d .
O6 O -0.00520(14) 0.00156(4) 0.25367(12) 0.01065(16) Uani 1 1 d .
O7 O 0.45590(14) 0.11325(4) 0.65942(12) 0.01036(16) Uani 1 1 d .
O8 O 0.61096(13) 0.05921(4) 0.79657(11) 0.00982(16) Uani 1 1 d .
O9 O 0.80284(17) 0.03146(4) 1.02794(13) 0.0154(2) Uani 1 1 d D
H19 H 0.864(4) 0.0205(12) 1.103(2) 0.023 Uiso 1 1 d D
H29 H 0.776(4) 0.0021(6) 0.993(3) 0.023 Uiso 1 1 d D
O10 O 0.91594(14) 0.13159(4) 1.11214(11) 0.01009(16) Uani 1 1 d D
H110 H 0.955(4) 0.1109(9) 1.179(2) 0.015 Uiso 1 1 d D
H210 H 0.882(4) 0.1579(7) 1.154(3) 0.015 Uiso 1 1 d D
O11 O 0.71212(13) 0.16359(4) 0.82074(12) 0.01039(16) Uani 1 1 d D
H111 H 0.786(3) 0.1722(11) 0.770(3) 0.016 Uiso 1 1 d D
H211 H 0.636(3) 0.1579(11) 0.749(2) 0.016 Uiso 1 1 d D
O12 O 0.56071(16) 0.11607(5) 1.03728(15) 0.0162(2) Uani 1 1 d D
H112 H 0.474(3) 0.0974(11) 1.028(4) 0.024 Uiso 1 1 d D
H212 H 0.554(6) 0.1393(12) 1.100(4) 0.052(13) Uiso 1 1 d D
O13 O 0.97874(13) 0.08917(4) 0.84815(11) 0.00897(15) Uani 1 1 d D
H113 H 0.999(4) 0.1054(10) 0.773(2) 0.013 Uiso 1 1 d D
H213 H 0.980(4) 0.0591(5) 0.816(3) 0.013 Uiso 1 1 d D
O1W O 0.25987(14) 0.07168(4) 0.05606(12) 0.01245(17) Uani 1 1 d D
H2W1 H 0.257(4) 0.0829(12) 0.1422(16) 0.019 Uiso 1 1 d D
H1W1 H 0.178(3) 0.0804(12) -0.008(3) 0.019 Uiso 1 1 d D
O2W O 0.85021(16) 0.20574(4) 0.27516(15) 0.0167(2) Uani 1 1 d D
H1W2 H 0.7449(12) 0.2046(13) 0.269(4) 0.025 Uiso 1 1 d D
H2W2 H 0.885(4) 0.2352(6) 0.257(4) 0.025 Uiso 1 1 d 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'
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'
Cu Cu 0.3201 1.2651 '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
O2 C1 O1 125.34(13)
O2 C1 C2 119.04(12)
O1 C1 C2 115.60(11)
N1 C2 C3 121.09(12)
N1 C2 C1 112.54(11)
C3 C2 C1 126.37(12)
C2 C3 C4 118.04(13)
C5 C4 C3 120.31(13)
C6 C5 C4 117.78(13)
N1 C6 C5 121.35(12)
N1 C6 C7 112.24(11)
C5 C6 C7 126.35(12)
O4 C7 O3 126.03(13)
O4 C7 C6 118.65(13)
O3 C7 C6 115.26(12)
O6 C8 O5 125.72(12)
O6 C8 C9 118.31(11)
O5 C8 C9 115.97(11)
N2 C9 C10 121.49(11)
N2 C9 C8 112.77(10)
C10 C9 C8 125.74(11)
C9 C10 C11 118.25(11)
C10 C11 C12 119.81(12)
C13 C12 C11 118.11(11)
N2 C13 C12 121.68(11)
N2 C13 C14 113.50(11)
C12 C13 C14 124.80(11)
O8 C14 O7 126.94(12)
O8 C14 C13 116.10(11)
O7 C14 C13 116.94(11)
O12 Cu1 O9 96.67(6)
O12 Cu1 O11 88.37(5)
O9 Cu1 O11 168.54(5)
O12 Cu1 O8 87.30(5)
O9 Cu1 O8 79.72(4)
O11 Cu1 O8 90.28(4)
O12 Cu1 O10 91.97(5)
O9 Cu1 O10 90.85(4)
O11 Cu1 O10 99.29(4)
O8 Cu1 O10 170.39(4)
O12 Cu1 O13 176.53(5)
O9 Cu1 O13 86.02(5)
O11 Cu1 O13 89.38(4)
O8 Cu1 O13 95.36(4)
O10 Cu1 O13 85.79(4)
N1 Cu2 N2 171.79(4)
N1 Cu2 O3 76.61(4)
N2 Cu2 O3 104.94(4)
N1 Cu2 O1 75.73(4)
N2 Cu2 O1 104.13(4)
O3 Cu2 O1 149.91(4)
N1 Cu2 O5 112.54(4)
N2 Cu2 O5 75.67(4)
O3 Cu2 O5 85.16(4)
O1 Cu2 O5 94.64(4)
N1 Cu2 O7 95.59(4)
N2 Cu2 O7 76.24(4)
O3 Cu2 O7 97.58(5)
O1 Cu2 O7 96.68(4)
O5 Cu2 O7 151.51(4)
C2 N1 C6 121.37(11)
C2 N1 Cu2 120.35(9)
C6 N1 Cu2 118.17(9)
C13 N2 C9 120.61(11)
C13 N2 Cu2 119.45(9)
C9 N2 Cu2 119.93(8)
C1 O1 Cu2 115.62(9)
C7 O3 Cu2 115.42(9)
C8 O5 Cu2 115.52(8)
C14 O7 Cu2 113.61(8)
C14 O8 Cu1 132.81(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.2444(17)
C1 O1 1.2763(17)
C1 C2 1.5119(18)
C2 N1 1.3308(17)
C2 C3 1.3917(19)
C3 C4 1.395(2)
C4 C5 1.393(2)
C5 C6 1.3904(19)
C6 N1 1.3348(17)
C6 C7 1.5131(19)
C7 O4 1.2461(18)
C7 O3 1.2728(18)
C8 O6 1.2497(16)
C8 O5 1.2688(16)
C8 C9 1.5061(17)
C9 N2 1.3364(16)
C9 C10 1.3903(18)
C10 C11 1.3933(18)
C11 C12 1.3940(19)
C12 C13 1.3906(18)
C13 N2 1.3332(16)
C13 C14 1.5105(17)
C14 O8 1.2484(16)
C14 O7 1.2706(16)
Cu1 O12 2.0525(12)
Cu1 O9 2.0565(11)
Cu1 O11 2.0853(11)
Cu1 O8 2.0879(10)
Cu1 O10 2.0899(10)
Cu1 O13 2.1654(11)
Cu2 N1 2.0213(11)
Cu2 N2 2.0265(11)
Cu2 O3 2.1131(11)
Cu2 O1 2.1697(11)
Cu2 O5 2.1779(10)
Cu2 O7 2.2134(11)
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
O2 C1 C2 N1 -179.03(13)
O1 C1 C2 N1 2.27(17)
O2 C1 C2 C3 1.1(2)
O1 C1 C2 C3 -177.63(14)
N1 C2 C3 C4 -1.3(2)
C1 C2 C3 C4 178.54(14)
C2 C3 C4 C5 1.5(2)
C3 C4 C5 C6 0.3(2)
C4 C5 C6 N1 -2.3(2)
C4 C5 C6 C7 174.69(14)
N1 C6 C7 O4 -179.25(13)
C5 C6 C7 O4 3.5(2)
N1 C6 C7 O3 3.29(17)
C5 C6 C7 O3 -173.93(14)
O6 C8 C9 N2 176.04(12)
O5 C8 C9 N2 -3.78(17)
O6 C8 C9 C10 -3.8(2)
O5 C8 C9 C10 176.39(13)
N2 C9 C10 C11 0.0(2)
C8 C9 C10 C11 179.81(13)
C9 C10 C11 C12 -1.9(2)
C10 C11 C12 C13 1.6(2)
C11 C12 C13 N2 0.6(2)
C11 C12 C13 C14 -177.58(13)
N2 C13 C14 O8 -173.55(12)
C12 C13 C14 O8 4.8(2)
N2 C13 C14 O7 4.99(17)
C12 C13 C14 O7 -176.69(13)
C3 C2 N1 C6 -0.6(2)
C1 C2 N1 C6 179.45(12)
C3 C2 N1 Cu2 175.48(10)
C1 C2 N1 Cu2 -4.42(15)
C5 C6 N1 C2 2.5(2)
C7 C6 N1 C2 -174.85(12)
C5 C6 N1 Cu2 -173.68(11)
C7 C6 N1 Cu2 8.94(14)
N2 Cu2 N1 C2 -86.4(3)
O3 Cu2 N1 C2 171.71(11)
O1 Cu2 N1 C2 3.69(10)
O5 Cu2 N1 C2 92.83(10)
O7 Cu2 N1 C2 -91.80(10)
N2 Cu2 N1 C6 89.9(3)
O3 Cu2 N1 C6 -12.04(10)
O1 Cu2 N1 C6 179.94(11)
O5 Cu2 N1 C6 -90.92(10)
O7 Cu2 N1 C6 84.45(10)
C12 C13 N2 C9 -2.57(19)
C14 C13 N2 C9 175.81(11)
C12 C13 N2 Cu2 175.65(10)
C14 C13 N2 Cu2 -5.97(15)
C10 C9 N2 C13 2.25(19)
C8 C9 N2 C13 -177.58(11)
C10 C9 N2 Cu2 -175.96(10)
C8 C9 N2 Cu2 4.21(15)
N1 Cu2 N2 C13 -1.6(4)
O3 Cu2 N2 C13 98.26(10)
O1 Cu2 N2 C13 -89.61(10)
O5 Cu2 N2 C13 179.14(11)
O7 Cu2 N2 C13 3.94(10)
N1 Cu2 N2 C9 176.6(3)
O3 Cu2 N2 C9 -83.51(10)
O1 Cu2 N2 C9 88.62(10)
O5 Cu2 N2 C9 -2.63(10)
O7 Cu2 N2 C9 -177.83(11)
O2 C1 O1 Cu2 -177.97(12)
C2 C1 O1 Cu2 0.65(15)
N1 Cu2 O1 C1 -2.20(10)
N2 Cu2 O1 C1 169.34(10)
O3 Cu2 O1 C1 -25.95(15)
O5 Cu2 O1 C1 -114.29(10)
O7 Cu2 O1 C1 91.90(10)
O4 C7 O3 Cu2 169.54(12)
C6 C7 O3 Cu2 -13.22(15)
N1 Cu2 O3 C7 13.79(10)
N2 Cu2 O3 C7 -157.90(10)
O1 Cu2 O3 C7 37.44(15)
O5 Cu2 O3 C7 128.34(10)
O7 Cu2 O3 C7 -80.19(10)
O6 C8 O5 Cu2 -178.08(11)
C9 C8 O5 Cu2 1.72(15)
N1 Cu2 O5 C8 -179.58(10)
N2 Cu2 O5 C8 0.30(10)
O3 Cu2 O5 C8 107.09(10)
O1 Cu2 O5 C8 -103.11(10)
O7 Cu2 O5 C8 10.11(16)
O8 C14 O7 Cu2 176.55(12)
C13 C14 O7 Cu2 -1.81(15)
N1 Cu2 O7 C14 178.29(10)
N2 Cu2 O7 C14 -0.92(10)
O3 Cu2 O7 C14 -104.52(10)
O1 Cu2 O7 C14 102.04(10)
O5 Cu2 O7 C14 -10.70(16)
O7 C14 O8 Cu1 13.6(2)
C13 C14 O8 Cu1 -167.98(9)
O12 Cu1 O8 C14 65.27(14)
O9 Cu1 O8 C14 162.55(14)
O11 Cu1 O8 C14 -23.09(14)
O10 Cu1 O8 C14 151.1(2)
O13 Cu1 O8 C14 -112.49(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339263
