#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:19:02 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229064 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/02/7230212.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_7230212
loop_
_publ_author_name
'Puttreddy, Rakesh'
'von Essen, Carolina'
'Peuronen, Anssi'
'Lahtinen, Manu'
'Rissanen, Kari'
_publ_section_title
;
 Halogen bonds in 2,5-dihalopyridine-copper(ii) chloride complexes
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              1954
_journal_paper_doi               10.1039/C8CE00209F
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C20 H12 Cl12 Cu2 N4'
_chemical_formula_sum            'C20 H12 Cl12 Cu2 N4'
_chemical_formula_weight         860.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_audit_update_record
;
2018-02-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.23(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.396(3)
_cell_length_b                   14.183(3)
_cell_length_c                   15.458(3)
_cell_measurement_reflns_used    3246
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.407
_cell_volume                     2878.1(12)
_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      170.0(1)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7740
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_min         2.114
_exptl_absorpt_coefficient_mu    2.614
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0594 before and 0.0472 after correction. The Ratio of minimum to maximum transmission is 0.8301. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.987
_exptl_crystal_description       block
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0202
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0197P)²+3.8531P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0503
_refine_ls_wR_factor_ref         0.0520
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2338
_reflns_number_total             2582
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00209f2.cif
_cod_data_source_block           2_4_CuCl2_2
_cod_depositor_comments
'Adding full bibliography for 7230211--7230222.cif.'
_cod_original_cell_volume        2878.2(12)
_cod_database_code               7230212
_shelx_shelxl_version_number     2014/7
_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.
;
_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), C3'(H3'), C4(H4), C4'(H4'), C6(H6), C6'(H6')
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
Cu1 Cu 0.36159(2) 0.58075(2) 0.61206(2) 0.01657(8) Uani 1 1 d .
Cl1 Cl 0.53147(4) 0.58138(3) 0.66253(3) 0.02404(12) Uani 1 1 d .
Cl1' Cl 0.18995(3) 0.58523(3) 0.57420(3) 0.01803(11) Uani 1 1 d .
Cl2 Cl 0.33382(5) 0.45030(4) 0.77461(3) 0.03251(14) Uani 1 1 d .
Cl2' Cl 0.37341(4) 0.68635(3) 0.79934(3) 0.02445(12) Uani 1 1 d .
Cl5 Cl 0.40358(4) 0.22569(4) 0.46712(4) 0.03016(13) Uani 1 1 d .
Cl5' Cl 0.38167(4) 0.95123(4) 0.48878(3) 0.02907(13) Uani 1 1 d .
N1 N 0.36346(12) 0.43445(11) 0.61901(10) 0.0195(4) Uani 1 1 d .
N1' N 0.36811(11) 0.72425(11) 0.63207(10) 0.0168(3) Uani 1 1 d .
C2 C 0.35173(15) 0.38597(15) 0.68803(13) 0.0212(4) Uani 1 1 d .
C2' C 0.37391(14) 0.76294(14) 0.71288(13) 0.0185(4) Uani 1 1 d .
C3 C 0.35573(16) 0.28895(15) 0.69532(14) 0.0255(5) Uani 1 1 d .
H3 H 0.3480 0.2586 0.7453 0.031 Uiso 1 1 calc R
C3' C 0.38165(15) 0.85858(14) 0.73112(13) 0.0214(4) Uani 1 1 d .
H3' H 0.3850 0.8820 0.7885 0.026 Uiso 1 1 calc R
C4 C 0.37150(15) 0.23825(15) 0.62662(14) 0.0245(5) Uani 1 1 d .
H4 H 0.3738 0.1727 0.6285 0.029 Uiso 1 1 calc R
C4' C 0.38420(16) 0.91822(14) 0.66181(14) 0.0225(4) Uani 1 1 d .
H4' H 0.3894 0.9831 0.6710 0.027 Uiso 1 1 calc R
C5 C 0.38382(15) 0.28724(14) 0.55478(13) 0.0214(4) Uani 1 1 d .
C5' C 0.37885(14) 0.87848(14) 0.57786(13) 0.0194(4) Uani 1 1 d .
C6 C 0.38143(14) 0.38426(14) 0.55294(13) 0.0202(4) Uani 1 1 d .
H6 H 0.3924 0.4160 0.5053 0.024 Uiso 1 1 calc R
C6' C 0.37121(14) 0.78275(14) 0.56453(13) 0.0186(4) Uani 1 1 d .
H6' H 0.3681 0.7577 0.5078 0.022 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'
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
Cl1 Cu1 Cl1' 99.00(4) 2_556
Cl1 Cu1 Cl1' 174.634(19) .
Cl1' Cu1 Cl1' 86.01(4) 2_556
N1 Cu1 Cl1 89.82(5) .
N1 Cu1 Cl1' 94.11(4) 2_556
N1 Cu1 Cl1' 91.75(5) .
N1' Cu1 Cl1 88.15(4) .
N1' Cu1 Cl1' 89.36(4) .
N1' Cu1 Cl1' 96.57(4) 2_556
N1' Cu1 N1 169.32(6) .
Cu1 Cl1' Cu1 93.91(4) 2_556
C2 N1 Cu1 123.49(13) .
C2 N1 C6 117.22(17) .
C6 N1 Cu1 119.25(13) .
C2' N1' Cu1 121.96(13) .
C2' N1' C6' 117.53(16) .
C6' N1' Cu1 120.45(12) .
N1 C2 Cl2 117.09(15) .
N1 C2 C3 124.28(18) .
C3 C2 Cl2 118.60(15) .
N1' C2' Cl2' 116.58(15) .
N1' C2' C3' 124.32(17) .
C3' C2' Cl2' 119.09(14) .
C2 C3 H3 120.9 .
C4 C3 C2 118.20(18) .
C4 C3 H3 120.9 .
C2' C3' H3' 121.0 .
C4' C3' C2' 118.04(17) .
C4' C3' H3' 121.0 .
C3 C4 H4 120.9 .
C3 C4 C5 118.27(19) .
C5 C4 H4 120.9 .
C3' C4' H4' 121.0 .
C3' C4' C5' 117.97(18) .
C5' C4' H4' 121.0 .
C4 C5 Cl5 119.48(16) .
C6 C5 Cl5 119.92(15) .
C6 C5 C4 120.59(18) .
C4' C5' Cl5' 119.37(15) .
C6' C5' Cl5' 119.76(14) .
C6' C5' C4' 120.87(17) .
N1 C6 C5 121.39(18) .
N1 C6 H6 119.3 .
C5 C6 H6 119.3 .
N1' C6' C5' 121.27(17) .
N1' C6' H6' 119.4 .
C5' C6' H6' 119.4 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Cl1 2.2413(8) .
Cu1 Cl1' 2.6629(8) 2_556
Cu1 Cl1' 2.2946(8) .
Cu1 N1 2.0773(17) .
Cu1 N1' 2.0550(17) .
Cl1' Cu1 2.6629(8) 2_556
Cl2 C2 1.724(2) .
Cl2' C2' 1.7247(19) .
Cl5 C5 1.731(2) .
Cl5' C5' 1.7344(19) .
N1 C2 1.337(2) .
N1 C6 1.354(2) .
N1' C2' 1.335(2) .
N1' C6' 1.349(2) .
C2 C3 1.380(3) .
C2' C3' 1.381(3) .
C3 H3 0.9300 .
C3 C4 1.376(3) .
C3' H3' 0.9300 .
C3' C4' 1.377(3) .
C4 H4 0.9300 .
C4 C5 1.382(3) .
C4' H4' 0.9300 .
C4' C5' 1.388(3) .
C5 C6 1.376(3) .
C5' C6' 1.371(3) .
C6 H6 0.9300 .
C6' H6' 0.9300 .
