#------------------------------------------------------------------------------
#$Date: 2019-11-17 08:51:53 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/97/7229776.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_7229776
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 Co I2 N4 O4'
_chemical_formula_sum            'C18 H20 Co I2 N4 O4'
_chemical_formula_weight         669.11
_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                102.241(8)
_cell_angle_beta                 100.737(9)
_cell_angle_gamma                98.708(11)
_cell_formula_units_Z            1
_cell_length_a                   6.3513(9)
_cell_length_b                   9.2560(11)
_cell_length_c                   10.3631(8)
_cell_measurement_reflns_used    1521
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.3730
_cell_measurement_theta_min      4.4190
_cell_volume                     573.27(12)
_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 0.992
_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  0.0244
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4009
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         4.271
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.471
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64739
_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    1.938
_exptl_crystal_description       block
_exptl_crystal_F_000             321
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.954
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0329
_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)+(0.0391P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0848
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1748
_reflns_number_total             2226
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce01989k2.cif
_cod_data_source_block           6a
_cod_depositor_comments
'Adding full bibliography for 7229768--7229780.cif.'
_cod_database_code               7229776
_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), C3(H3), C7(H7)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C9(H9A,H9B,H9C)
;
_olex2_date_sample_data_collection 2016-02-09
_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
I1 I 0.50385(5) 0.21152(4) 0.97343(3) 0.07043(16) Uani 1 1 d . . .
Co1 Co 0.5000 0.5000 0.5000 0.0415(2) Uani 1 2 d S T P
O1 O 0.3269(4) 0.6640(3) 0.4866(3) 0.0504(7) Uani 1 1 d . . .
O2 O 0.7383(4) 0.6491(3) 0.6457(3) 0.0518(7) Uani 1 1 d . . .
N1 N 0.3415(5) 0.4428(4) 0.6628(3) 0.0464(8) Uani 1 1 d . . .
N2 N 0.1697(6) 0.3771(5) 0.8770(4) 0.0615(10) Uani 1 1 d . . .
C1 C 0.4337(6) 0.3649(5) 0.7442(4) 0.0469(9) Uani 1 1 d . . .
H1 H 0.5605 0.3318 0.7297 0.056 Uiso 1 1 calc R . .
C2 C 0.3472(6) 0.3321(5) 0.8486(4) 0.0474(9) Uani 1 1 d . . .
C6 C 0.3723(7) 0.7947(5) 0.5625(4) 0.0492(10) Uani 1 1 d . . .
C4 C 0.1614(6) 0.4871(5) 0.6904(4) 0.0527(10) Uani 1 1 d . . .
H4 H 0.0903 0.5418 0.6367 0.063 Uiso 1 1 calc R . .
C8 C 0.7294(7) 0.7814(5) 0.7010(4) 0.0525(10) Uani 1 1 d . . .
C3 C 0.0780(7) 0.4542(6) 0.7958(5) 0.0653(13) Uani 1 1 d . . .
H3 H -0.0484 0.4874 0.8110 0.078 Uiso 1 1 calc R . .
C7 C 0.5564(7) 0.8536(5) 0.6667(4) 0.0584(11) Uani 1 1 d . . .
H7 H 0.5659 0.9504 0.7190 0.070 Uiso 1 1 calc R . .
C5 C 0.2061(8) 0.8924(6) 0.5324(5) 0.0776(15) Uani 1 1 d . . .
H5A H 0.2089 0.9147 0.4463 0.116 Uiso 1 1 calc GR . .
H5B H 0.2419 0.9847 0.6020 0.116 Uiso 1 1 calc GR . .
H5C H 0.0627 0.8394 0.5299 0.116 Uiso 1 1 calc GR . .
C9 C 0.9224(8) 0.8670(7) 0.8135(5) 0.0816(16) Uani 1 1 d . . .
H9A H 0.9212 0.8268 0.8916 0.122 Uiso 1 1 calc GR . .
H9B H 0.9137 0.9717 0.8366 0.122 Uiso 1 1 calc GR . .
H9C H 1.0554 0.8570 0.7841 0.122 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'
Co Co 0.3494 0.9721 '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'
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 90.09(11) 2_666 .
O1 Co1 O2 89.91(11) 2_666 2_666
O1 Co1 O2 89.91(11) . .
O1 Co1 O2 90.08(11) . 2_666
O1 Co1 N1 89.66(11) 2_666 .
O1 Co1 N1 90.34(11) 2_666 2_666
O1 Co1 N1 89.66(11) . 2_666
O1 Co1 N1 90.34(11) . .
O2 Co1 O2 180.00(13) . 2_666
O2 Co1 N1 91.36(12) 2_666 .
O2 Co1 N1 88.64(12) . .
O2 Co1 N1 88.64(12) 2_666 2_666
O2 Co1 N1 91.36(12) . 2_666
N1 Co1 N1 180.0 . 2_666
C6 O1 Co1 126.3(2) . .
C8 O2 Co1 126.1(3) . .
C1 N1 Co1 119.8(3) . .
C4 N1 Co1 124.6(3) . .
C4 N1 C1 115.6(3) . .
C2 N2 C3 115.3(4) . .
N1 C1 H1 119.0 . .
N1 C1 C2 121.9(4) . .
C2 C1 H1 119.0 . .
N2 C2 I1 117.7(3) . .
N2 C2 C1 122.7(4) . .
C1 C2 I1 119.6(3) . .
O1 C6 C7 125.6(4) . .
O1 C6 C5 114.8(4) . .
C7 C6 C5 119.6(4) . .
N1 C4 H4 119.1 . .
N1 C4 C3 121.7(4) . .
C3 C4 H4 119.1 . .
O2 C8 C7 125.3(4) . .
O2 C8 C9 116.1(4) . .
C7 C8 C9 118.6(4) . .
N2 C3 C4 122.8(4) . .
N2 C3 H3 118.6 . .
C4 C3 H3 118.6 . .
C6 C7 C8 126.2(4) . .
C6 C7 H7 116.9 . .
C8 C7 H7 116.9 . .
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 . .
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
I1 C2 2.093(4) .
Co1 O1 2.018(2) .
Co1 O1 2.018(2) 2_666
Co1 O2 2.026(3) .
Co1 O2 2.026(3) 2_666
Co1 N1 2.233(3) .
Co1 N1 2.233(3) 2_666
O1 C6 1.254(5) .
O2 C8 1.252(5) .
N1 C1 1.333(5) .
N1 C4 1.332(5) .
N2 C2 1.321(5) .
N2 C3 1.325(6) .
C1 H1 0.9300 .
C1 C2 1.369(6) .
C6 C7 1.385(6) .
C6 C5 1.521(5) .
C4 H4 0.9300 .
C4 C3 1.368(6) .
C8 C7 1.399(6) .
C8 C9 1.508(6) .
C3 H3 0.9300 .
C7 H7 0.9300 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
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 2.59 3.276(5) 131.1 1_455
C3 H3 O2 0.93 2.80 3.383(5) 121.7 1_455
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
Co1 O1 C6 C7 3.1(6)
Co1 O1 C6 C5 -177.3(3)
Co1 O2 C8 C7 -3.7(6)
Co1 O2 C8 C9 176.1(3)
Co1 N1 C1 C2 177.5(3)
Co1 N1 C4 C3 -176.9(4)
O1 C6 C7 C8 3.8(8)
O2 C8 C7 C6 -3.5(8)
N1 C1 C2 I1 -179.2(3)
N1 C1 C2 N2 -1.1(7)
N1 C4 C3 N2 0.1(8)
C1 N1 C4 C3 0.1(6)
C2 N2 C3 C4 -0.7(7)
C4 N1 C1 C2 0.4(6)
C3 N2 C2 I1 179.4(3)
C3 N2 C2 C1 1.2(6)
C5 C6 C7 C8 -175.8(4)
C9 C8 C7 C6 176.8(4)
