#------------------------------------------------------------------------------
#$Date: 2019-11-17 08:51:53 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/97/7229770.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_7229770
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 Cl2 N4 Ni O4'
_chemical_formula_sum            'C18 H20 Cl2 N4 Ni O4'
_chemical_formula_weight         485.99
_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                100.977(7)
_cell_angle_beta                 100.919(7)
_cell_angle_gamma                99.073(6)
_cell_formula_units_Z            1
_cell_length_a                   6.3212(5)
_cell_length_b                   8.9502(7)
_cell_length_c                   10.0197(8)
_cell_measurement_reflns_used    1303
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.3260
_cell_measurement_theta_min      4.4570
_cell_volume                     535.27(8)
_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 0.997
_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  0.0221
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4103
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         4.151
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96620
_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    1.508
_exptl_crystal_description       plate
_exptl_crystal_F_000             250
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0388
_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)+(0.0413P)²+0.0017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0859
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1803
_reflns_number_total             2100
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce01989k2.cif
_cod_data_source_block           4b
_cod_depositor_comments
'Adding full bibliography for 7229768--7229780.cif.'
_cod_database_code               7229770
_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 2016-03-30
_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
Ni1 Ni 0.5000 0.5000 0.5000 0.04007(16) Uani 1 2 d S T P
Cl1 Cl 0.50170(15) 0.22183(11) 0.96731(9) 0.0824(3) Uani 1 1 d . . .
O1 O 0.6739(3) 0.3329(2) 0.51164(18) 0.0493(4) Uani 1 1 d . . .
O2 O 0.2572(3) 0.3560(2) 0.35073(18) 0.0502(4) Uani 1 1 d . . .
N1 N 0.3513(3) 0.4370(2) 0.6651(2) 0.0441(5) Uani 1 1 d . . .
N2 N 0.1921(4) 0.3706(3) 0.8935(3) 0.0664(7) Uani 1 1 d . . .
C1 C 0.4498(4) 0.3578(3) 0.7496(3) 0.0489(6) Uani 1 1 d . . .
H1 H 0.5758 0.3234 0.7330 0.059 Uiso 1 1 calc R . .
C6 C 0.6271(4) 0.2006(3) 0.4286(3) 0.0495(6) Uani 1 1 d . . .
C8 C 0.2687(4) 0.2216(3) 0.2880(3) 0.0517(6) Uani 1 1 d . . .
C4 C 0.1713(4) 0.4824(3) 0.6949(3) 0.0532(7) Uani 1 1 d . . .
H4 H 0.0960 0.5369 0.6382 0.064 Uiso 1 1 calc R . .
C2 C 0.3679(4) 0.3262(3) 0.8610(3) 0.0521(6) Uani 1 1 d . . .
C3 C 0.0950(5) 0.4497(4) 0.8082(3) 0.0668(8) Uani 1 1 d . . .
H3 H -0.0301 0.4845 0.8261 0.080 Uiso 1 1 calc R . .
C7 C 0.4421(5) 0.1466(3) 0.3198(3) 0.0594(7) Uani 1 1 d . . .
H7 H 0.4332 0.0501 0.2622 0.071 Uiso 1 1 calc R . .
C5 C 0.7929(5) 0.0992(3) 0.4563(4) 0.0756(10) Uani 1 1 d . . .
H5A H 0.9376 0.1559 0.4615 0.113 Uiso 1 1 calc GR . .
H5B H 0.7582 0.0079 0.3819 0.113 Uiso 1 1 calc GR . .
H5C H 0.7882 0.0695 0.5430 0.113 Uiso 1 1 calc GR . .
C9 C 0.0749(5) 0.1404(4) 0.1694(3) 0.0814(10) Uani 1 1 d . . .
H9A H -0.0585 0.1613 0.1946 0.122 Uiso 1 1 calc GR . .
H9B H 0.0696 0.0304 0.1511 0.122 Uiso 1 1 calc GR . .
H9C H 0.0902 0.1776 0.0874 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'
Cl Cl 0.1484 0.1585 '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'
Ni Ni 0.3393 1.1124 '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 Ni1 O1 180.0 2_666 .
O1 Ni1 O2 91.77(7) . .
O1 Ni1 O2 88.23(7) . 2_666
O1 Ni1 O2 88.23(7) 2_666 .
O1 Ni1 O2 91.77(7) 2_666 2_666
O1 Ni1 N1 90.50(7) . 2_666
O1 Ni1 N1 89.50(7) . .
O1 Ni1 N1 90.51(7) 2_666 .
O1 Ni1 N1 89.50(7) 2_666 2_666
O2 Ni1 O2 180.0 . 2_666
O2 Ni1 N1 92.26(7) 2_666 2_666
O2 Ni1 N1 87.74(7) . 2_666
O2 Ni1 N1 87.74(7) 2_666 .
O2 Ni1 N1 92.26(7) . .
N1 Ni1 N1 180.0 2_666 .
C6 O1 Ni1 125.06(17) . .
C8 O2 Ni1 124.62(17) . .
C1 N1 Ni1 119.74(15) . .
C4 N1 Ni1 123.74(16) . .
C4 N1 C1 116.4(2) . .
C2 N2 C3 114.5(2) . .
N1 C1 H1 119.5 . .
N1 C1 C2 120.9(2) . .
C2 C1 H1 119.5 . .
O1 C6 C7 125.3(2) . .
O1 C6 C5 114.3(3) . .
C7 C6 C5 120.4(3) . .
O2 C8 C7 125.4(2) . .
O2 C8 C9 115.4(3) . .
C7 C8 C9 119.2(3) . .
N1 C4 H4 119.5 . .
N1 C4 C3 121.1(2) . .
C3 C4 H4 119.5 . .
N2 C2 Cl1 116.9(2) . .
N2 C2 C1 124.0(2) . .
C1 C2 Cl1 119.1(2) . .
N2 C3 C4 123.1(2) . .
N2 C3 H3 118.5 . .
C4 C3 H3 118.5 . .
C6 C7 C8 126.8(3) . .
C6 C7 H7 116.6 . .
C8 C7 H7 116.6 . .
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
Ni1 O1 1.9984(15) 2_666
Ni1 O1 1.9984(15) .
Ni1 O2 2.0067(17) 2_666
Ni1 O2 2.0067(17) .
Ni1 N1 2.1714(19) 2_666
Ni1 N1 2.1714(19) .
Cl1 C2 1.735(3) .
O1 C6 1.266(3) .
O2 C8 1.266(3) .
N1 C1 1.333(3) .
N1 C4 1.333(3) .
N2 C2 1.314(3) .
N2 C3 1.333(3) .
C1 H1 0.9300 .
C1 C2 1.373(3) .
C6 C7 1.388(4) .
C6 C5 1.512(3) .
C8 C7 1.391(4) .
C8 C9 1.510(4) .
C4 H4 0.9300 .
C4 C3 1.377(4) .
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 2.58 3.265(3) 131.1 2_566
C3 H3 O2 0.93 2.81 3.384(3) 121.1 2_566
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
Ni1 O1 C6 C7 -3.2(4)
Ni1 O1 C6 C5 176.84(15)
Ni1 O2 C8 C7 5.9(3)
Ni1 O2 C8 C9 -174.07(17)
Ni1 N1 C1 C2 175.3(2)
Ni1 N1 C4 C3 -174.5(2)
O1 C6 C7 C8 -4.8(4)
O2 C8 C7 C6 3.3(4)
N1 C1 C2 Cl1 179.69(19)
N1 C1 C2 N2 -0.4(4)
N1 C4 C3 N2 -0.8(5)
C1 N1 C4 C3 0.7(4)
C4 N1 C1 C2 -0.2(4)
C2 N2 C3 C4 0.2(5)
C3 N2 C2 Cl1 -179.7(2)
C3 N2 C2 C1 0.4(4)
C5 C6 C7 C8 175.1(3)
C9 C8 C7 C6 -176.8(3)
