#------------------------------------------------------------------------------
#$Date: 2019-11-17 08:51:53 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/97/7229774.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_7229774
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 I2 N4 Ni O4'
_chemical_formula_sum            'C18 H20 I2 N4 Ni O4'
_chemical_formula_weight         668.89
_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                102.659(5)
_cell_angle_beta                 100.162(4)
_cell_angle_gamma                98.163(4)
_cell_formula_units_Z            1
_cell_length_a                   6.3490(3)
_cell_length_b                   9.2589(5)
_cell_length_c                   10.2457(4)
_cell_measurement_reflns_used    2347
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      31.7240
_cell_measurement_theta_min      5.0780
_cell_volume                     568.11(5)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0177
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4563
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         4.149
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79869
_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            'light blue'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.955
_exptl_crystal_description       block
_exptl_crystal_F_000             322
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0287
_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)+(0.0259P)²+0.2987P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0662
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2139
_reflns_number_total             2476
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce01989k2.cif
_cod_data_source_block           6b
_cod_depositor_comments
'Adding full bibliography for 7229768--7229780.cif.'
_cod_database_code               7229774
_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 2016-02-13
_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 0.49138(4) 0.78627(3) 0.02676(2) 0.06575(11) Uani 1 1 d . . .
Ni1 Ni 0.5000 0.5000 0.5000 0.03766(13) Uani 1 2 d S T P
O1 O 0.3242(3) 0.6613(2) 0.4886(2) 0.0454(5) Uani 1 1 d . . .
O2 O 0.7378(3) 0.6432(3) 0.6469(2) 0.0484(5) Uani 1 1 d . . .
N1 N 0.6537(4) 0.5578(3) 0.3406(2) 0.0411(5) Uani 1 1 d . . .
N2 N 0.8292(5) 0.6247(4) 0.1254(3) 0.0573(7) Uani 1 1 d . . .
C6 C 0.3749(5) 0.7939(4) 0.5643(3) 0.0464(7) Uani 1 1 d . . .
C2 C 0.6488(5) 0.6669(3) 0.1534(3) 0.0431(6) Uani 1 1 d . . .
C1 C 0.5597(5) 0.6351(3) 0.2591(3) 0.0437(7) Uani 1 1 d . . .
H1 H 0.4322 0.6679 0.2739 0.052 Uiso 1 1 calc R . .
C4 C 0.8362(5) 0.5151(4) 0.3144(3) 0.0494(7) Uani 1 1 d . . .
H4 H 0.9077 0.4618 0.3695 0.059 Uiso 1 1 calc R . .
C8 C 0.7301(5) 0.7770(4) 0.7015(3) 0.0484(7) Uani 1 1 d . . .
C7 C 0.5605(6) 0.8517(4) 0.6674(4) 0.0558(8) Uani 1 1 d . . .
H7 H 0.5730 0.9499 0.7187 0.067 Uiso 1 1 calc R . .
C3 C 0.9219(5) 0.5478(4) 0.2076(4) 0.0594(9) Uani 1 1 d . . .
H3 H 1.0493 0.5150 0.1924 0.071 Uiso 1 1 calc R . .
C5 C 0.2127(7) 0.8940(4) 0.5351(4) 0.0686(10) Uani 1 1 d . . .
H5A H 0.2226 0.9203 0.4506 0.103 Uiso 1 1 calc GR . .
H5B H 0.2447 0.9840 0.6083 0.103 Uiso 1 1 calc GR . .
H5C H 0.0681 0.8413 0.5282 0.103 Uiso 1 1 calc GR . .
C9 C 0.9235(7) 0.8610(5) 0.8144(4) 0.0772(12) Uani 1 1 d . . .
H9A H 0.9286 0.8160 0.8905 0.116 Uiso 1 1 calc GR . .
H9B H 0.9098 0.9645 0.8433 0.116 Uiso 1 1 calc GR . .
H9C H 1.0551 0.8559 0.7810 0.116 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'
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'
Ni Ni 0.3393 1.1124 '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'
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 Ni1 O1 180.00(9) 2_666 .
O1 Ni1 O2 88.24(9) . 2_666
O1 Ni1 O2 91.76(9) . .
O1 Ni1 O2 91.76(9) 2_666 2_666
O1 Ni1 O2 88.24(9) 2_666 .
O1 Ni1 N1 90.35(9) . 2_666
O1 Ni1 N1 89.65(9) . .
O1 Ni1 N1 90.35(9) 2_666 .
O1 Ni1 N1 89.65(9) 2_666 2_666
O2 Ni1 O2 180.00(10) 2_666 .
O2 Ni1 N1 88.70(9) . 2_666
O2 Ni1 N1 91.30(9) 2_666 2_666
O2 Ni1 N1 91.30(9) . .
O2 Ni1 N1 88.70(9) 2_666 .
N1 Ni1 N1 180.0 2_666 .
C6 O1 Ni1 124.98(19) . .
C8 O2 Ni1 124.9(2) . .
C1 N1 Ni1 119.84(19) . .
C4 N1 Ni1 123.6(2) . .
C4 N1 C1 116.5(3) . .
C2 N2 C3 115.2(3) . .
O1 C6 C7 126.0(3) . .
O1 C6 C5 114.5(3) . .
C7 C6 C5 119.5(3) . .
N2 C2 I1 117.3(2) . .
N2 C2 C1 123.5(3) . .
C1 C2 I1 119.2(2) . .
N1 C1 C2 120.9(3) . .
N1 C1 H1 119.6 . .
C2 C1 H1 119.6 . .
N1 C4 H4 119.2 . .
N1 C4 C3 121.6(3) . .
C3 C4 H4 119.2 . .
O2 C8 C7 125.7(3) . .
O2 C8 C9 115.6(3) . .
C7 C8 C9 118.7(3) . .
C6 C7 C8 126.4(3) . .
C6 C7 H7 116.8 . .
C8 C7 H7 116.8 . .
N2 C3 C4 122.4(3) . .
N2 C3 H3 118.8 . .
C4 C3 H3 118.8 . .
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 . .
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 2.095(3) .
Ni1 O1 1.9983(19) 2_666
Ni1 O1 1.9984(19) .
Ni1 O2 2.014(2) 2_666
Ni1 O2 2.014(2) .
Ni1 N1 2.169(2) 2_666
Ni1 N1 2.169(2) .
O1 C6 1.263(4) .
O2 C8 1.255(4) .
N1 C1 1.331(4) .
N1 C4 1.329(4) .
N2 C2 1.320(4) .
N2 C3 1.330(4) .
C6 C7 1.388(5) .
C6 C5 1.514(4) .
C2 C1 1.374(4) .
C1 H1 0.9300 .
C4 H4 0.9300 .
C4 C3 1.376(5) .
C8 C7 1.394(5) .
C8 C9 1.511(5) .
C7 H7 0.9300 .
C3 H3 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 3.259(4) 129.0 2_766
C3 H3 O2 0.93 2.74 3.335(4) 122.5 2_766
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
I1 C2 C1 N1 179.1(2)
Ni1 O1 C6 C7 0.5(4)
Ni1 O1 C6 C5 -179.6(2)
Ni1 O2 C8 C7 -2.4(4)
Ni1 O2 C8 C9 177.2(2)
Ni1 N1 C1 C2 -177.0(2)
Ni1 N1 C4 C3 176.6(3)
O1 C6 C7 C8 3.6(5)
O2 C8 C7 C6 -2.6(6)
N1 C4 C3 N2 0.6(6)
N2 C2 C1 N1 0.0(5)
C2 N2 C3 C4 -0.2(5)
C1 N1 C4 C3 -0.7(5)
C4 N1 C1 C2 0.4(4)
C3 N2 C2 I1 -179.3(2)
C3 N2 C2 C1 -0.1(5)
C5 C6 C7 C8 -176.2(3)
C9 C8 C7 C6 177.8(3)
