#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:19:02 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229064 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/02/7230215.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_7230215
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         'C10 H6 Br2 Cl4 Cu N2'
_chemical_formula_sum            'C10 H6 Br2 Cl4 Cu N2'
_chemical_formula_weight         519.33
_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
_atom_sites_solution_primary     direct
_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                 91.79(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1656(16)
_cell_length_b                   12.708(3)
_cell_length_c                   14.591(3)
_cell_measurement_reflns_used    1250
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407
_cell_volume                     1513.3(6)
_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 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.0208
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2880
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.241
_diffrn_reflns_theta_max         25.241
_diffrn_reflns_theta_min         2.966
_exptl_absorpt_coefficient_mu    7.414
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1122 before and 0.0461 after correction. The Ratio of minimum to maximum transmission is 0.6445. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.279
_exptl_crystal_description       block
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     87
_refine_ls_number_reflns         1341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0237
_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)+(0.0072P)²+4.2282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0526
_refine_ls_wR_factor_ref         0.0543
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1224
_reflns_number_total             1341
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00209f2.cif
_cod_data_source_block           6_2_CuCl2
_cod_depositor_comments
'Adding full bibliography for 7230211--7230222.cif.'
_cod_original_cell_volume        1513.4(5)
_cod_database_code               7230215
_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), C4(H4), C6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Br2 Br 0.35668(4) 0.08036(3) 0.34809(2) 0.03286(13) Uani 1 1 d . . .
Cu1 Cu 0.5000 0.29458(4) 0.2500 0.02006(14) Uani 1 2 d S T P
Cl1 Cl 0.75616(8) 0.35444(6) 0.24197(5) 0.02715(18) Uani 1 1 d . . .
Cl5 Cl 0.65997(11) 0.43672(6) 0.60189(5) 0.0346(2) Uani 1 1 d . . .
N1 N 0.5151(3) 0.26776(18) 0.38645(15) 0.0201(5) Uani 1 1 d . . .
C2 C 0.4451(4) 0.1856(2) 0.42589(19) 0.0231(6) Uani 1 1 d . . .
C3 C 0.4361(4) 0.1734(3) 0.5201(2) 0.0282(7) Uani 1 1 d . . .
H3 H 0.3863 0.1146 0.5450 0.034 Uiso 1 1 calc R . .
C4 C 0.5033(4) 0.2512(3) 0.57593(19) 0.0272(7) Uani 1 1 d . . .
H4 H 0.4993 0.2461 0.6394 0.033 Uiso 1 1 calc R . .
C5 C 0.5763(3) 0.3362(2) 0.53534(18) 0.0228(6) Uani 1 1 d . . .
C6 C 0.5821(4) 0.3428(2) 0.44110(19) 0.0229(6) Uani 1 1 d . . .
H6 H 0.6333 0.4002 0.4147 0.027 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'
Br Br -0.2901 2.4595 '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_1
_geom_angle_site_symmetry_3
Cl1 Cu1 Cl1 140.15(5) 2_655 .
N1 Cu1 Cl1 91.96(7) 2_655 .
N1 Cu1 Cl1 91.97(7) . 2_655
N1 Cu1 Cl1 94.63(7) . .
N1 Cu1 Cl1 94.63(7) 2_655 2_655
N1 Cu1 N1 160.57(13) . 2_655
C2 N1 Cu1 123.02(19) . .
C2 N1 C6 118.1(2) . .
C6 N1 Cu1 118.35(19) . .
N1 C2 Br2 117.3(2) . .
N1 C2 C3 123.6(3) . .
C3 C2 Br2 119.1(2) . .
C2 C3 H3 120.9 . .
C4 C3 C2 118.1(3) . .
C4 C3 H3 120.9 . .
C3 C4 H4 120.8 . .
C5 C4 C3 118.5(3) . .
C5 C4 H4 120.8 . .
C4 C5 Cl5 120.4(2) . .
C4 C5 C6 120.3(3) . .
C6 C5 Cl5 119.2(2) . .
N1 C6 C5 121.4(3) . .
N1 C6 H6 119.3 . .
C5 C6 H6 119.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br2 C2 1.883(3) .
Cu1 Cl1 2.2323(8) .
Cu1 Cl1 2.2322(8) 2_655
Cu1 N1 2.020(2) 2_655
Cu1 N1 2.020(2) .
Cl5 C5 1.732(3) .
N1 C2 1.330(4) .
N1 C6 1.348(4) .
C2 C3 1.387(4) .
C3 H3 0.9300 .
C3 C4 1.384(4) .
C4 H4 0.9300 .
C4 C5 1.377(4) .
C5 C6 1.380(4) .
C6 H6 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
Br2 C2 C3 C4 179.4(2)
Cu1 N1 C2 Br2 9.6(3)
Cu1 N1 C2 C3 -171.3(2)
Cu1 N1 C6 C5 171.1(2)
Cl5 C5 C6 N1 -178.4(2)
N1 C2 C3 C4 0.2(5)
C2 N1 C6 C5 -1.1(4)
C2 C3 C4 C5 -0.3(5)
C3 C4 C5 Cl5 179.1(2)
C3 C4 C5 C6 -0.2(4)
C4 C5 C6 N1 1.0(4)
C6 N1 C2 Br2 -178.6(2)
C6 N1 C2 C3 0.5(4)
