#------------------------------------------------------------------------------
#$Date: 2019-11-07 22:12:39 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223730 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/24/7232419.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_7232419
loop_
_publ_author_name
'Hearne, Neil'
'Turnbull, Mark M.'
'Landee, Christopher P.'
'van der Merwe, Elizabet M.'
'Rademeyer, Melanie'
_publ_section_title
;
 Halide-bi-bridged polymers of amide substituted pyridines and -pyrazines:
 polymorphism, structures, thermal stability and magnetism
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              1910
_journal_paper_doi               10.1039/C9CE00071B
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C12 H12 Cl2 Cu N4 O2'
_chemical_formula_sum            'C12 H12 Cl2 Cu N4 O2'
_chemical_formula_weight         378.71
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-12-12 deposited with the CCDC.    2019-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.493(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.171(4)
_cell_length_b                   3.7103(5)
_cell_length_c                   32.824(5)
_cell_measurement_reflns_used    9911
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.26
_cell_measurement_theta_min      2.62
_cell_volume                     2739.0(7)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'SHELXTL, SHELXL-2014/7 (Sheldrick, 2015)'
_computing_publication_material
;
 ORTEP-3 for Windows (Farrugia, 1997), POV-RAY (Cason, 2004),
 Mercury (Macrae et al., 2008)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXTS (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            33282
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.147
_exptl_absorpt_coefficient_mu    1.993
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.837
_exptl_crystal_description       needle
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.339
_refine_diff_density_min         -1.052
_refine_diff_density_rms         0.176
_refine_ls_extinction_coef       0.0005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2809
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0652
_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)+(0.0784P)²+68.4533P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1799
_refine_ls_wR_factor_ref         0.1843
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2490
_reflns_number_total             2809
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00071b2.cif
_cod_data_source_block           inicCuCla
_cod_depositor_comments
'Adding full bibliography for 7232418--7232424.cif.'
_cod_database_code               7232419
_shelx_shelxl_version_number     2018/3
_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_min   0.741
_shelx_estimated_absorpt_t_max   0.961
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
Cu1 Cu 0.49665(3) 0.4054(2) 0.37168(2) 0.0094(3) Uani 1 1 d . .
Cl2 Cl 0.55602(7) 0.0561(4) 0.34675(5) 0.0113(4) Uani 1 1 d . .
Cl1 Cl 0.44361(7) 0.8296(4) 0.39421(5) 0.0094(4) Uani 1 1 d . .
O1 O 0.7355(2) 0.8046(16) 0.56288(15) 0.0208(12) Uani 1 1 d . .
O2 O 0.2488(2) 0.6347(15) 0.17990(16) 0.0203(12) Uani 1 1 d . .
N3 N 0.4320(3) 0.4154(16) 0.31148(18) 0.0133(4) Uani 1 1 d . .
N4 N 0.3125(3) 0.4281(16) 0.14910(18) 0.0133(4) Uani 1 1 d . .
H4A H 0.286695 0.457576 0.122261 0.016 Uiso 1 1 calc R U
H4B H 0.348153 0.342219 0.153440 0.016 Uiso 1 1 calc R U
N1 N 0.5615(3) 0.4265(16) 0.43157(18) 0.0133(4) Uani 1 1 d . .
N2 N 0.6772(3) 0.5597(16) 0.59526(18) 0.0133(4) Uani 1 1 d . .
H2A H 0.701725 0.621344 0.621584 0.016 Uiso 1 1 calc R U
H2B H 0.644198 0.443063 0.592042 0.016 Uiso 1 1 calc R U
C10 C 0.3303(3) 0.3588(18) 0.26278(19) 0.0120(14) Uani 1 1 d D .
H10 H 0.290346 0.302534 0.258880 0.014 Uiso 1 1 calc R U
C11 C 0.3751(3) 0.3345(18) 0.3039(2) 0.0109(13) Uani 1 1 d D .
H11 H 0.364806 0.257013 0.327830 0.013 Uiso 1 1 calc R U
C7 C 0.4458(3) 0.520(2) 0.2772(2) 0.0133(4) Uani 1 1 d D .
H7 H 0.486014 0.577525 0.282008 0.016 Uiso 1 1 calc R U
C8 C 0.4039(3) 0.5481(18) 0.2352(2) 0.0122(13) Uani 1 1 d D .
H8 H 0.415550 0.622570 0.211826 0.015 Uiso 1 1 calc R U
C9 C 0.3449(3) 0.4669(17) 0.2274(2) 0.0098(13) Uani 1 1 d D .
C12 C 0.2976(3) 0.513(2) 0.1831(2) 0.0144(14) Uani 1 1 d . .
C2 C 0.5889(3) 0.4044(19) 0.5097(2) 0.0133(4) Uani 1 1 d D .
H2 H 0.578295 0.348300 0.534180 0.016 Uiso 1 1 calc R U
C1 C 0.5483(3) 0.3507(19) 0.4673(2) 0.0133(4) Uani 1 1 d D .
H1 H 0.510102 0.257526 0.463343 0.016 Uiso 1 1 calc R U
C5 C 0.6162(3) 0.541(2) 0.4381(2) 0.0133(4) Uani 1 1 d D .
H5 H 0.626563 0.581269 0.413166 0.016 Uiso 1 1 calc R U
C4 C 0.6591(3) 0.6046(19) 0.47917(19) 0.0133(4) Uani 1 1 d D .
H4 H 0.697395 0.690121 0.482041 0.016 Uiso 1 1 calc R U
C3 C 0.6452(3) 0.5416(19) 0.5161(2) 0.0133(4) Uani 1 1 d D .
C6 C 0.6901(3) 0.6426(19) 0.5604(2) 0.0133(4) 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'
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_
_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
N1 Cu1 N3 176.7(3) .
N1 Cu1 Cl2 90.31(17) .
N3 Cu1 Cl2 91.25(17) .
N1 Cu1 Cl1 89.18(17) .
N3 Cu1 Cl1 88.86(17) .
Cl2 Cu1 Cl1 171.56(7) .
N1 Cu1 Cl1 92.32(18) 1_545
N3 Cu1 Cl1 90.45(18) 1_545
Cl2 Cu1 Cl1 94.11(6) 1_545
Cl1 Cu1 Cl1 94.33(6) 1_545
Cu1 Cl1 Cu1 94.33(6) 1_565
C11 N3 C7 117.6(6) .
C11 N3 Cu1 123.4(4) .
C7 N3 Cu1 119.0(5) .
C12 N4 H4A 120.0 .
C12 N4 H4B 120.0 .
H4A N4 H4B 120.0 .
C5 N1 C1 117.6(6) .
C5 N1 Cu1 122.7(4) .
C1 N1 Cu1 119.5(5) .
C6 N2 H2A 120.0 .
C6 N2 H2B 120.0 .
H2A N2 H2B 120.0 .
C11 C10 C9 119.0(6) .
C11 C10 H10 120.5 .
C9 C10 H10 120.5 .
N3 C11 C10 123.1(6) .
N3 C11 H11 118.4 .
C10 C11 H11 118.4 .
N3 C7 C8 122.8(6) .
N3 C7 H7 118.6 .
C8 C7 H7 118.6 .
C7 C8 C9 119.7(6) .
C7 C8 H8 120.1 .
C9 C8 H8 120.1 .
C8 C9 C10 117.8(6) .
C8 C9 C12 121.6(6) .
C10 C9 C12 120.5(6) .
O2 C12 N4 124.2(6) .
O2 C12 C9 119.5(6) .
N4 C12 C9 116.3(6) .
C1 C2 C3 119.4(6) .
C1 C2 H2 120.3 .
C3 C2 H2 120.3 .
N1 C1 C2 122.3(6) .
N1 C1 H1 118.8 .
C2 C1 H1 118.8 .
N1 C5 C4 123.7(6) .
N1 C5 H5 118.2 .
C4 C5 H5 118.2 .
C5 C4 C3 119.1(6) .
C5 C4 H4 120.5 .
C3 C4 H4 120.5 .
C4 C3 C2 117.7(6) .
C4 C3 C6 118.7(6) .
C2 C3 C6 123.4(6) .
O1 C6 N2 122.9(6) .
O1 C6 C3 119.7(6) .
N2 C6 C3 117.4(6) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 2.017(6) .
Cu1 N3 2.021(6) .
Cu1 Cl2 2.2954(18) .
Cu1 Cl1 2.3157(17) .
Cu1 Cl1 2.7294(18) 1_545
O1 C6 1.226(9) .
O2 C12 1.232(9) .
N3 C11 1.341(9) .
N3 C7 1.342(8) .
N4 C12 1.329(9) .
N4 H4A 0.8800 .
N4 H4B 0.8800 .
N1 C5 1.331(9) .
N1 C1 1.353(8) .
N2 C6 1.328(9) .
N2 H2A 0.8800 .
N2 H2B 0.8800 .
C10 C11 1.390(8) .
C10 C9 1.392(8) .
C10 H10 0.9500 .
C11 H11 0.9500 .
C7 C8 1.383(8) .
C7 H7 0.9500 .
C8 C9 1.386(8) .
C8 H8 0.9500 .
C9 C12 1.494(9) .
C2 C1 1.393(8) .
C2 C3 1.397(8) .
C2 H2 0.9500 .
C1 H1 0.9500 .
C5 C4 1.387(8) .
C5 H5 0.9500 .
C4 C3 1.389(8) .
C4 H4 0.9500 .
C3 C6 1.510(9) .
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
_geom_hbond_publ_flag
N4 H4A O1 0.88 2.08 2.932(7) 161.7 8_465 yes
N4 H4B Cl2 0.88 2.55 3.421(6) 170.7 2_655 yes
N2 H2A O2 0.88 2.04 2.911(8) 167.8 8_566 yes
N2 H2B Cl1 0.88 2.54 3.388(6) 163.0 5_666 yes
C10 H10 O2 0.95 2.59 3.244(8) 126.2 4_545 yes
C11 H11 Cl1 0.95 2.80 3.382(6) 120.3 1_545 yes
C7 H7 Cl2 0.95 2.81 3.436(7) 124.3 1_565 yes
C8 H8 Cl2 0.95 2.78 3.693(7) 161.5 2_665 yes
C2 H2 Cl1 0.95 2.67 3.623(7) 175.9 5_666 yes
C1 H1 Cl1 0.95 2.75 3.384(7) 124.6 1_545 yes
C5 H5 Cl2 0.95 2.84 3.400(7) 119.1 1_565 yes
C4 H4 O1 0.95 2.56 3.330(8) 138.2 7_666 yes
N4 H4A O1 0.88 2.08 2.932(7) 161.7 8_465 yes
N4 H4B Cl2 0.88 2.55 3.421(6) 170.7 2_655 yes
N2 H2A O2 0.88 2.04 2.911(8) 167.8 8_566 yes
N2 H2B Cl1 0.88 2.54 3.388(6) 163.0 5_666 yes
C10 H10 O2 0.95 2.59 3.244(8) 126.2 4_545 yes
C11 H11 Cl1 0.95 2.80 3.382(6) 120.3 1_545 yes
C7 H7 Cl2 0.95 2.81 3.436(7) 124.3 1_565 yes
C8 H8 Cl2 0.95 2.78 3.693(7) 161.5 2_665 yes
C2 H2 Cl1 0.95 2.67 3.623(7) 175.9 5_666 yes
C1 H1 Cl1 0.95 2.75 3.384(7) 124.6 1_545 yes
C5 H5 Cl2 0.95 2.84 3.400(7) 119.1 1_565 yes
C4 H4 O1 0.95 2.56 3.330(8) 138.2 7_666 yes
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
C7 N3 C11 C10 -0.8(10)
Cu1 N3 C11 C10 176.8(5)
C9 C10 C11 N3 1.0(10)
C11 N3 C7 C8 0.2(10)
Cu1 N3 C7 C8 -177.4(5)
N3 C7 C8 C9 0.2(11)
C7 C8 C9 C10 0.0(10)
C7 C8 C9 C12 176.5(6)
C11 C10 C9 C8 -0.5(10)
C11 C10 C9 C12 -177.1(6)
C8 C9 C12 O2 -139.9(7)
C10 C9 C12 O2 36.5(10)
C8 C9 C12 N4 38.1(10)
C10 C9 C12 N4 -145.5(7)
C5 N1 C1 C2 3.0(10)
Cu1 N1 C1 C2 -171.6(5)
C3 C2 C1 N1 0.1(11)
C1 N1 C5 C4 -3.6(11)
Cu1 N1 C5 C4 170.8(6)
N1 C5 C4 C3 1.1(11)
C5 C4 C3 C2 2.1(11)
C5 C4 C3 C6 -174.6(7)
C1 C2 C3 C4 -2.6(11)
C1 C2 C3 C6 174.0(7)
C4 C3 C6 O1 6.1(11)
C2 C3 C6 O1 -170.5(7)
C4 C3 C6 N2 -176.1(7)
C2 C3 C6 N2 7.4(11)
