#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:19:02 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229064 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/02/7230222.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_7230222
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 Cl8 Cu2 I4 N4'
_chemical_formula_sum            'C20 H12 Cl8 Cu2 I4 N4'
_chemical_formula_weight         1226.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-I 2y'
_space_group_name_H-M_alt        'I 1 2/m 1'
_symmetry_space_group_name_Hall  '-I 2y'
_symmetry_space_group_name_H-M   'I 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-02-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.89(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0829(16)
_cell_length_b                   14.605(3)
_cell_length_c                   13.664(3)
_cell_measurement_reflns_used    2845
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.407
_cell_volume                     1612.2(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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7375
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.244
_diffrn_reflns_theta_min         2.042
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.833
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0780 before and 0.0498 after correction. The Ratio of minimum to maximum transmission is 0.7331. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    2.527
_exptl_crystal_description       block
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0192
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0152P)²+4.5168P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0430
_refine_ls_wR_factor_ref         0.0440
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1423
_reflns_number_total             1516
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00209f2.cif
_cod_data_source_block           4_1_4_CuCl2_2
_cod_depositor_comments
'Adding full bibliography for 7230211--7230222.cif.'
_cod_original_cell_volume        1612.1(6)
_cod_database_code               7230222
_shelxl_version_number           2013-2
_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_max   0.347
_shelx_estimated_absorpt_t_min   0.302
_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'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
I5 I 0.72811(2) 0.13895(2) 0.64866(2) 0.03251(9) Uani 1 1 d . . .
Cu1 Cu 0.39128(6) 0.5000 0.61454(4) 0.01807(12) Uani 1 2 d S T P
Cl1 Cl 0.43653(12) 0.5000 0.78035(8) 0.0257(2) Uani 1 2 d S T P
Cl1' Cl 0.30235(11) 0.5000 0.45154(7) 0.0192(2) Uani 1 2 d S T P
Cl2 Cl 0.05552(9) 0.38345(5) 0.62312(6) 0.03307(19) Uani 1 1 d . . .
N1 N 0.3756(3) 0.36018(15) 0.61908(17) 0.0201(5) Uani 1 1 d . . .
C2 C 0.2299(3) 0.31671(19) 0.6222(2) 0.0225(6) Uani 1 1 d . . .
C3 C 0.2152(4) 0.2228(2) 0.6266(2) 0.0292(7) Uani 1 1 d . . .
H3 H 0.1093 0.1945 0.6260 0.035 Uiso 1 1 calc R . .
C4 C 0.3577(4) 0.1706(2) 0.6319(2) 0.0295(7) Uani 1 1 d . . .
H4 H 0.3517 0.1057 0.6357 0.035 Uiso 1 1 calc R . .
C5 C 0.5090(3) 0.21452(19) 0.6315(2) 0.0226(6) Uani 1 1 d . . .
C6 C 0.5146(3) 0.30913(18) 0.6244(2) 0.0217(6) Uani 1 1 d . . .
H6 H 0.6191 0.3388 0.6232 0.026 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'
I I -0.4742 1.8119 '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' 102.48(5) . 5_666
Cl1 Cu1 Cl1' 171.16(4) . .
Cl1' Cu1 Cl1' 86.37(4) . 5_666
N1 Cu1 Cl1 88.74(7) 6_565 .
N1 Cu1 Cl1 88.74(7) . .
N1 Cu1 Cl1' 93.99(7) 6_565 5_666
N1 Cu1 Cl1' 90.66(7) 6_565 .
N1 Cu1 Cl1' 90.66(7) . .
N1 Cu1 Cl1' 93.99(7) . 5_666
N1 Cu1 N1 171.98(13) 6_565 .
Cu1 Cl1' Cu1 93.63(4) . 5_666
C2 N1 Cu1 121.94(18) . .
C2 N1 C6 117.9(2) . .
C6 N1 Cu1 120.06(18) . .
N1 C2 Cl2 117.0(2) . .
N1 C2 C3 123.3(3) . .
C3 C2 Cl2 119.6(2) . .
C2 C3 H3 120.7 . .
C2 C3 C4 118.6(3) . .
C4 C3 H3 120.7 . .
C3 C4 H4 120.7 . .
C3 C4 C5 118.7(3) . .
C5 C4 H4 120.7 . .
C4 C5 I5 120.0(2) . .
C4 C5 C6 119.6(3) . .
C6 C5 I5 120.3(2) . .
N1 C6 C5 121.8(3) . .
N1 C6 H6 119.1 . .
C5 C6 H6 119.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I5 C5 2.093(3) .
Cu1 Cl1 2.2830(12) .
Cu1 Cl1' 2.6636(12) 5_666
Cu1 Cl1' 2.3176(12) .
Cu1 N1 2.047(2) 6_565
Cu1 N1 2.047(2) .
Cl1' Cu1 2.6637(12) 5_666
Cl2 C2 1.714(3) .
N1 C2 1.340(4) .
N1 C6 1.348(4) .
C2 C3 1.379(4) .
C3 H3 0.9500 .
C3 C4 1.381(4) .
C4 H4 0.9500 .
C4 C5 1.382(4) .
C5 C6 1.386(4) .
C6 H6 0.9500 .
