#------------------------------------------------------------------------------
#$Date: 2019-11-17 08:51:53 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/97/7229771.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_7229771
loop_
_publ_author_name
'Borovina, Mladen'
'Kodrin, Ivan'
'Đaković, Marijana'
_publ_section_title
;
 Testing the limits of halogen bonding in coordination chemistry
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              539
_journal_paper_doi               10.1039/C7CE01989K
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C18 H20 Br2 Co N4 O4'
_chemical_formula_sum            'C18 H20 Br2 Co N4 O4'
_chemical_formula_weight         575.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-10-27 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                100.396(6)
_cell_angle_beta                 101.149(7)
_cell_angle_gamma                100.044(6)
_cell_formula_units_Z            1
_cell_length_a                   6.3290(5)
_cell_length_b                   8.9473(6)
_cell_length_c                   10.2742(7)
_cell_measurement_reflns_used    1470
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      30.9810
_cell_measurement_theta_min      4.5090
_cell_volume                     548.09(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4340
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         4.339
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.459
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark orange'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_description       block
_exptl_crystal_F_000             285
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0354
_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)+(0.0407P)²+0.1584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0864
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1893
_reflns_number_total             2373
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce01989k2.cif
_cod_data_source_block           5a
_cod_depositor_comments
'Adding full bibliography for 7229768--7229780.cif.'
_cod_database_code               7229771
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C7(H7), C3(H3)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C9(H9A,H9B,H9C)
;
_olex2_date_sample_data_collection 2016-02-16
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Co1 Co 0.5000 0.5000 0.5000 0.03464(15) Uani 1 2 d S T P
Br1 Br 0.50568(7) 0.21222(4) 0.97161(4) 0.06823(16) Uani 1 1 d . . .
O1 O 0.6687(3) 0.3299(2) 0.5134(2) 0.0439(5) Uani 1 1 d . . .
O2 O 0.2561(3) 0.3494(2) 0.3528(2) 0.0451(5) Uani 1 1 d . . .
N1 N 0.3431(4) 0.4374(3) 0.6666(2) 0.0400(5) Uani 1 1 d . . .
N2 N 0.1848(4) 0.3702(3) 0.8890(3) 0.0579(7) Uani 1 1 d . . .
C1 C 0.4407(5) 0.3572(3) 0.7488(3) 0.0419(6) Uani 1 1 d . . .
H1 H 0.5653 0.3226 0.7323 0.050 Uiso 1 1 calc R . .
C6 C 0.6257(5) 0.2000(3) 0.4309(3) 0.0417(7) Uani 1 1 d . . .
C4 C 0.1658(5) 0.4831(4) 0.6957(3) 0.0476(7) Uani 1 1 d . . .
H4 H 0.0926 0.5389 0.6406 0.057 Uiso 1 1 calc R . .
C2 C 0.3589(5) 0.3254(3) 0.8573(3) 0.0439(7) Uani 1 1 d . . .
C8 C 0.2690(5) 0.2174(3) 0.2909(3) 0.0445(7) Uani 1 1 d . . .
C7 C 0.4430(6) 0.1446(3) 0.3226(3) 0.0509(8) Uani 1 1 d . . .
H7 H 0.4363 0.0496 0.2658 0.061 Uiso 1 1 calc R . .
C5 C 0.7928(6) 0.1002(4) 0.4575(4) 0.0627(9) Uani 1 1 d . . .
H5A H 0.9377 0.1590 0.4633 0.094 Uiso 1 1 calc GR . .
H5B H 0.7580 0.0097 0.3845 0.094 Uiso 1 1 calc GR . .
H5C H 0.7884 0.0686 0.5416 0.094 Uiso 1 1 calc GR . .
C3 C 0.0879(5) 0.4497(4) 0.8056(4) 0.0595(9) Uani 1 1 d . . .
H3 H -0.0368 0.4838 0.8225 0.071 Uiso 1 1 calc R . .
C9 C 0.0762(6) 0.1350(5) 0.1737(4) 0.0718(11) Uani 1 1 d . . .
H9A H -0.0592 0.1446 0.2000 0.108 Uiso 1 1 calc GR . .
H9B H 0.0801 0.0269 0.1495 0.108 Uiso 1 1 calc GR . .
H9C H 0.0851 0.1812 0.0970 0.108 Uiso 1 1 calc GR . .
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'
Co Co 0.3494 0.9721 '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_1
_geom_angle_site_symmetry_3
O1 Co1 O1 180.0 . 2_666
O1 Co1 O2 90.10(8) 2_666 .
O1 Co1 O2 89.90(8) 2_666 2_666
O1 Co1 O2 89.90(8) . .
O1 Co1 O2 90.10(8) . 2_666
O1 Co1 N1 89.67(8) 2_666 2_666
O1 Co1 N1 90.33(8) 2_666 .
O1 Co1 N1 89.67(8) . .
O1 Co1 N1 90.33(8) . 2_666
O2 Co1 O2 180.0 . 2_666
O2 Co1 N1 92.54(8) 2_666 2_666
O2 Co1 N1 87.46(8) . 2_666
O2 Co1 N1 87.46(8) 2_666 .
O2 Co1 N1 92.54(8) . .
N1 Co1 N1 180.0 2_666 .
C6 O1 Co1 125.77(18) . .
C8 O2 Co1 125.46(18) . .
C1 N1 Co1 118.61(19) . .
C4 N1 Co1 124.6(2) . .
C4 N1 C1 116.7(3) . .
C2 N2 C3 114.8(3) . .
N1 C1 H1 119.7 . .
N1 C1 C2 120.6(3) . .
C2 C1 H1 119.7 . .
O1 C6 C7 125.6(2) . .
O1 C6 C5 114.7(3) . .
C7 C6 C5 119.7(3) . .
N1 C4 H4 119.3 . .
N1 C4 C3 121.4(3) . .
C3 C4 H4 119.3 . .
N2 C2 Br1 117.2(2) . .
N2 C2 C1 124.0(3) . .
C1 C2 Br1 118.8(2) . .
O2 C8 C7 125.3(3) . .
O2 C8 C9 115.6(3) . .
C7 C8 C9 119.0(3) . .
C6 C7 C8 126.3(3) . .
C6 C7 H7 116.8 . .
C8 C7 H7 116.8 . .
C6 C5 H5A 109.5 . .
C6 C5 H5B 109.5 . .
C6 C5 H5C 109.5 . .
H5A C5 H5B 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
N2 C3 C4 122.5(3) . .
N2 C3 H3 118.7 . .
C4 C3 H3 118.7 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9B 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Co1 O1 2.0152(17) .
Co1 O1 2.0152(17) 2_666
Co1 O2 2.0304(19) 2_666
Co1 O2 2.0304(19) .
Co1 N1 2.245(2) 2_666
Co1 N1 2.245(2) .
Br1 C2 1.898(3) .
O1 C6 1.261(3) .
O2 C8 1.261(3) .
N1 C1 1.334(3) .
N1 C4 1.327(4) .
N2 C2 1.314(4) .
N2 C3 1.336(4) .
C1 H1 0.9300 .
C1 C2 1.371(4) .
C6 C7 1.387(4) .
C6 C5 1.515(4) .
C4 H4 0.9300 .
C4 C3 1.376(5) .
C8 C7 1.389(4) .
C8 C9 1.510(4) .
C7 H7 0.9300 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
C3 H3 0.9300 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
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
C4 H4 O2 0.93 2.58 3.282(3) 132.2 2_566
C3 H3 O2 0.93 2.85 3.416(4) 120.4 2_566
