#------------------------------------------------------------------------------
#$Date: 2019-11-17 13:58:42 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/76/7057660.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_7057660
loop_
_publ_author_name
'Rad-Yousefnia, Negar'
'Shaabani, Behrouz'
'Zahedi, Mansoureh'
'Kubicki, Maciej'
'Aygün, Muhittin'
'Lloret, Francesc'
'Julve, Miguel'
'Grześkiewicz, Anita M.'
'Zakerhamidi, Mohammad Sadegh'
'Kazak, Canan'
_publ_section_title
;
 Cd(ii) and Cu(ii) coordination polymers constructed from the expanded
 1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene ligand: conventional and
 ultrasound-assisted synthesis, crystal structure, luminescence and
 magnetic properties
;
_journal_issue                   19
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15860
_journal_paper_doi               10.1039/C8NJ02605J
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C12 H10 Cu N6 O6, C H Cl3'
_chemical_formula_sum            'C13 H11 Cl3 Cu N6 O6'
_chemical_formula_weight         517.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-01-29 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.285(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5429(4)
_cell_length_b                   11.9046(6)
_cell_length_c                   17.3544(10)
_cell_measurement_reflns_used    2141
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0490
_cell_measurement_theta_min      3.9250
_cell_volume                     1959.69(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0667
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  77.00   1.00   45.26    --   20.07  19.00 -60.00  103
  2  ω    -10.00  55.00   1.00   45.26    --   20.07 -99.00  90.00   65
  3  ω    -17.00   9.00   1.00   45.26    --  -22.02 -99.00-150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0185301000
_diffrn_orient_matrix_UB_12      -0.0569691000
_diffrn_orient_matrix_UB_13      0.0052638000
_diffrn_orient_matrix_UB_21      -0.0136601000
_diffrn_orient_matrix_UB_22      -0.0067450000
_diffrn_orient_matrix_UB_23      -0.0407328000
_diffrn_orient_matrix_UB_31      0.0711684000
_diffrn_orient_matrix_UB_32      -0.0160990000
_diffrn_orient_matrix_UB_33      -0.0017071000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6347
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.081
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.568
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.753
_exptl_crystal_description       prism
_exptl_crystal_F_000             1036
_exptl_crystal_preparation       'Magnetic properties,Luminescent'
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.135
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0466
_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)+(0.0440P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2712
_reflns_number_total             3944
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj02605j2.cif
_cod_data_source_block           iran_a425_2
_cod_depositor_comments
'Adding full bibliography for 7057660--7057662.cif.'
_cod_original_cell_volume        1959.68(17)
_cod_database_code               7057660
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C13 H11 Cl3 Cu N6 O6'
_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 98.67
_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 Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C0AA(H0AA), C4(H4), C1AA(H1AA), C2AA(H2AA), C7(H7), C8(H8), C9(H9), C11(H11),
 C12(H12), C13(H13)
;
_olex2_date_sample_data_collection 2015-10-16
_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 1.058
_oxdiff_exptl_absorpt_empirical_full_min 0.953
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Cu1 Cu 0.41629(4) 0.05532(3) 0.08389(2) 0.03317(15) Uani 1 1 d .
O1 O 0.5894(3) -0.0796(2) 0.18120(15) 0.0504(7) Uani 1 1 d .
O2 O 0.7282(3) -0.1633(3) 0.10900(17) 0.0674(9) Uani 1 1 d .
O3 O 0.5684(2) -0.0520(2) 0.05820(13) 0.0343(6) Uani 1 1 d .
O4 O 0.2582(2) 0.1688(2) 0.08358(14) 0.0399(6) Uani 1 1 d .
O5 O 0.3138(3) 0.1196(3) 0.20197(15) 0.0538(8) Uani 1 1 d .
O6 O 0.1377(3) 0.2321(3) 0.17255(17) 0.0677(9) Uani 1 1 d .
N1 N -0.0318(3) -0.4046(3) 0.09812(19) 0.0473(8) Uani 1 1 d .
N2 N 0.2733(3) -0.0670(2) 0.07594(16) 0.0304(7) Uani 1 1 d .
N3 N 0.5566(3) 0.1783(2) 0.09917(16) 0.0317(7) Uani 1 1 d .
N4 N 0.8600(3) 0.5175(3) 0.07685(19) 0.0470(8) Uani 1 1 d .
N3AA N 0.6313(3) -0.1007(3) 0.11842(19) 0.0373(7) Uani 1 1 d .
N4AA N 0.2356(3) 0.1749(3) 0.1548(2) 0.0426(8) Uani 1 1 d .
C0AA C -0.0322(3) -0.3267(3) 0.0493(2) 0.0402(9) Uani 1 1 d .
H0AA H -0.099250 -0.326207 0.006199 0.048 Uiso 1 1 calc R
C3 C 0.0727(3) -0.2364(3) 0.0603(2) 0.0319(8) Uani 1 1 d .
C4 C 0.0785(3) -0.1551(3) 0.0043(2) 0.0380(9) Uani 1 1 d .
H4 H 0.014583 -0.156335 -0.040209 0.046 Uiso 1 1 calc R
C1AA C 0.1784(3) -0.0724(3) 0.0142(2) 0.0367(9) Uani 1 1 d .
H1AA H 0.179785 -0.017670 -0.023944 0.044 Uiso 1 1 calc R
C2AA C 0.2672(3) -0.1449(3) 0.1304(2) 0.0368(9) Uani 1 1 d .
H2AA H 0.332244 -0.141531 0.174367 0.044 Uiso 1 1 calc R
C7 C 0.1701(3) -0.2297(3) 0.1249(2) 0.0379(9) Uani 1 1 d .
H7 H 0.169628 -0.282419 0.164445 0.045 Uiso 1 1 calc R
C8 C 0.5567(3) 0.2602(3) 0.0473(2) 0.0385(9) Uani 1 1 d .
H8 H 0.487839 0.259400 0.005028 0.046 Uiso 1 1 calc R
C9 C 0.6532(4) 0.3458(3) 0.0529(2) 0.0405(9) Uani 1 1 d .
H9 H 0.649528 0.401362 0.015085 0.049 Uiso 1 1 calc R
C10 C 0.7559(3) 0.3484(3) 0.1155(2) 0.0336(8) Uani 1 1 d .
C11 C 0.7540(4) 0.2651(3) 0.1703(2) 0.0469(10) Uani 1 1 d .
H11 H 0.820316 0.264622 0.213734 0.056 Uiso 1 1 calc R
C12 C 0.6534(4) 0.1833(3) 0.1601(2) 0.0439(10) Uani 1 1 d .
H12 H 0.652748 0.127960 0.197916 0.053 Uiso 1 1 calc R
C13 C 0.8626(4) 0.4379(3) 0.1256(2) 0.0413(9) Uani 1 1 d .
H13 H 0.931866 0.436067 0.167633 0.050 Uiso 1 1 calc R
Cl1 Cl -0.05543(13) 0.11443(12) 0.34904(8) 0.0797(4) Uani 1 1 d .
Cl2 Cl 0.16894(17) -0.04292(15) 0.36150(11) 0.1228(7) Uani 1 1 d .
Cl3 Cl -0.03151(17) -0.03608(17) 0.22538(11) 0.1291(7) Uani 1 1 d .
C1 C 0.0604(5) 0.0406(4) 0.2992(3) 0.0665(13) Uani 1 1 d .
H1 H 0.119879 0.094906 0.275478 0.080 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'
Cl Cl 0.1484 0.1585 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -6 -22 0.1115
13 -4 0 0.1013
4 5 21 0.0717
-13 3 -1 0.0958
11 -10 0 0.1117
9 11 -10 0.0799
-12 8 1 0.0891
10 11 1 0.0346
0 1 -24 0.1000
0 -1 24 0.0820
-5 -12 16 0.0865
-6 -15 2 0.0714
-4 -15 -5 0.0739
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_3
O3 Cu1 O4 167.10(10) .
N2 Cu1 O3 91.46(10) .
N2 Cu1 O4 89.05(10) .
N3 Cu1 O3 90.31(10) .
N3 Cu1 O4 89.98(10) .
N3 Cu1 N2 176.19(11) .
N3AA O3 Cu1 112.9(2) .
N4AA O4 Cu1 103.9(2) .
C0AA N1 N4 111.2(3) 1_445
C1AA N2 Cu1 119.6(2) .
C1AA N2 C2AA 117.5(3) .
C2AA N2 Cu1 123.0(2) .
C8 N3 Cu1 120.2(2) .
C8 N3 C12 117.1(3) .
C12 N3 Cu1 122.7(2) .
C13 N4 N1 110.9(3) 1_665
O1 N3AA O3 117.5(3) .
O2 N3AA O1 124.9(3) .
O2 N3AA O3 117.6(3) .
O5 N4AA O4 117.1(3) .
O6 N4AA O4 119.3(3) .
O6 N4AA O5 123.5(3) .
N1 C0AA H0AA 119.9 .
N1 C0AA C3 120.1(3) .
C3 C0AA H0AA 119.9 .
C4 C3 C0AA 120.2(3) .
C4 C3 C7 117.3(3) .
C7 C3 C0AA 122.5(3) .
C3 C4 H4 120.1 .
C1AA C4 C3 119.9(3) .
C1AA C4 H4 120.1 .
N2 C1AA C4 122.8(3) .
N2 C1AA H1AA 118.6 .
C4 C1AA H1AA 118.6 .
N2 C2AA H2AA 118.4 .
N2 C2AA C7 123.2(3) .
C7 C2AA H2AA 118.4 .
C3 C7 H7 120.3 .
C2AA C7 C3 119.4(3) .
C2AA C7 H7 120.3 .
N3 C8 H8 118.4 .
N3 C8 C9 123.3(3) .
C9 C8 H8 118.4 .
C8 C9 H9 120.4 .
C8 C9 C10 119.1(3) .
C10 C9 H9 120.4 .
C9 C10 C13 122.2(3) .
C11 C10 C9 117.7(3) .
C11 C10 C13 120.1(3) .
C10 C11 H11 120.4 .
C12 C11 C10 119.2(3) .
C12 C11 H11 120.4 .
N3 C12 C11 123.5(3) .
N3 C12 H12 118.2 .
C11 C12 H12 118.2 .
N4 C13 C10 119.9(3) .
N4 C13 H13 120.0 .
C10 C13 H13 120.0 .
Cl1 C1 Cl2 110.7(3) .
Cl1 C1 Cl3 109.9(2) .
Cl1 C1 H1 107.9 .
Cl2 C1 Cl3 112.4(3) .
Cl2 C1 H1 107.9 .
Cl3 C1 H1 107.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O3 2.020(2) .
Cu1 O4 2.025(2) .
Cu1 N2 1.990(2) .
Cu1 N3 1.982(2) .
O1 N3AA 1.227(4) .
O2 N3AA 1.213(4) .
O3 N3AA 1.285(3) .
O4 N4AA 1.280(4) .
O5 N4AA 1.235(4) .
O6 N4AA 1.222(3) .
N1 N4 1.407(4) 1_445
N1 C0AA 1.255(4) .
N2 C1AA 1.327(4) .
N2 C2AA 1.330(4) .
N3 C8 1.327(4) .
N3 C12 1.327(4) .
N4 C13 1.269(4) .
C0AA H0AA 0.9300 .
C0AA C3 1.467(4) .
C3 C4 1.378(5) .
C3 C7 1.378(5) .
C4 H4 0.9300 .
C4 C1AA 1.367(4) .
C1AA H1AA 0.9300 .
C2AA H2AA 0.9300 .
C2AA C7 1.367(4) .
C7 H7 0.9300 .
C8 H8 0.9300 .
C8 C9 1.369(4) .
C9 H9 0.9300 .
C9 C10 1.381(5) .
C10 C11 1.375(5) .
C10 C13 1.470(4) .
C11 H11 0.9300 .
C11 C12 1.366(4) .
C12 H12 0.9300 .
C13 H13 0.9300 .
Cl1 C1 1.719(4) .
Cl2 C1 1.728(5) .
Cl3 C1 1.731(5) .
C1 H1 0.9800 .
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
Cu1 O3 N3AA O1 2.3(3) .
Cu1 O3 N3AA O2 -177.1(2) .
Cu1 O4 N4AA O5 3.4(3) .
Cu1 O4 N4AA O6 -175.0(3) .
Cu1 N2 C1AA C4 179.0(3) .
Cu1 N2 C2AA C7 -179.4(3) .
Cu1 N3 C8 C9 -177.9(3) .
Cu1 N3 C12 C11 177.6(3) .
N1 N4 C13 C10 178.5(3) 1_665
N1 C0AA C3 C4 175.6(3) .
N1 C0AA C3 C7 -3.3(5) .
N2 C2AA C7 C3 0.0(5) .
N3 C8 C9 C10 -0.2(6) .
N4 N1 C0AA C3 -179.8(3) 1_445
C0AA C3 C4 C1AA -178.8(3) .
C0AA C3 C7 C2AA 178.3(3) .
C3 C4 C1AA N2 0.8(5) .
C4 C3 C7 C2AA -0.6(5) .
C1AA N2 C2AA C7 1.0(5) .
C2AA N2 C1AA C4 -1.4(5) .
C7 C3 C4 C1AA 0.2(5) .
C8 N3 C12 C11 -2.2(5) .
C8 C9 C10 C11 -1.4(5) .
C8 C9 C10 C13 -179.7(3) .
C9 C10 C11 C12 1.1(5) .
C9 C10 C13 N4 1.7(5) .
C10 C11 C12 N3 0.7(6) .
C11 C10 C13 N4 -176.6(4) .
C12 N3 C8 C9 2.0(5) .
C13 C10 C11 C12 179.5(3) .
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0040 -5.9974 -22.0006 0.2630 0.9640 -0.0085
13.0024 -3.9980 -0.0082 -0.0132 -0.1503 0.9897
4.0042 4.9979 20.9993 -0.2484 -0.9438 0.1687
-13.0025 2.9983 -0.9920 0.0649 0.1978 -0.9719
11.0020 -9.9975 -0.0084 0.3656 -0.0825 0.9440
8.9999 11.0004 -10.0029 -0.8461 0.2103 0.4805
-12.0020 7.9975 1.0085 -0.2279 0.0689 -0.9846
10.0020 10.9995 0.9967 -0.8067 -0.2514 0.5330
-0.0040 1.0020 -24.0003 -0.1833 0.9709 0.0246
0.0040 -1.0020 24.0003 0.1833 -0.9709 -0.0246
-4.9982 -12.0004 16.0006 0.8605 -0.5025 -0.1898
-6.0007 -14.9988 2.0002 0.9762 0.1017 -0.1890
-4.0015 -14.9980 -5.0011 0.9022 0.3595 -0.0348
