#------------------------------------------------------------------------------
#$Date: 2019-11-17 08:51:53 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/97/7229780.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_7229780
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 N4 Ni O4'
_chemical_formula_sum            'C18 H20 Br2 N4 Ni O4'
_chemical_formula_weight         574.91
_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                101.295(7)
_cell_angle_beta                 100.541(6)
_cell_angle_gamma                99.102(7)
_cell_formula_units_Z            1
_cell_length_a                   6.3344(4)
_cell_length_b                   9.0280(8)
_cell_length_c                   10.1145(7)
_cell_measurement_reflns_used    1433
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      31.2180
_cell_measurement_theta_min      4.3170
_cell_volume                     546.23(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 0.996
_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  0.0148
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4386
_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         26.998
_diffrn_reflns_theta_min         4.141
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48123
_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    1.748
_exptl_crystal_description       prism
_exptl_crystal_F_000             286
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0312
_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)+(0.0244P)²+0.2513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0632
_refine_ls_wR_factor_ref         0.0675
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1970
_reflns_number_total             2375
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce01989k2.cif
_cod_data_source_block           5b
_cod_depositor_comments
'Adding full bibliography for 7229768--7229780.cif.'
_cod_database_code               7229780
_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
Ni1 Ni 0.5000 0.5000 0.5000 0.03640(12) Uani 1 2 d S T P
Br1 Br 0.49103(6) 0.78399(4) 0.02841(3) 0.07050(14) Uani 1 1 d . . .
O1 O 0.6735(3) 0.3337(2) 0.51120(18) 0.0450(4) Uani 1 1 d . . .
O2 O 0.2586(3) 0.3560(2) 0.35168(18) 0.0466(4) Uani 1 1 d . . .
N1 N 0.6512(3) 0.5624(2) 0.3371(2) 0.0409(5) Uani 1 1 d . . .
N2 N 0.8151(4) 0.6289(3) 0.1132(3) 0.0597(6) Uani 1 1 d . . .
C6 C 0.6252(5) 0.2016(3) 0.4299(3) 0.0456(6) Uani 1 1 d . . .
C1 C 0.5533(4) 0.6406(3) 0.2537(3) 0.0445(6) Uani 1 1 d . . .
H1 H 0.4266 0.6739 0.2698 0.053 Uiso 1 1 calc R . .
C4 C 0.8321(4) 0.5182(3) 0.3082(3) 0.0493(7) Uani 1 1 d . . .
H4 H 0.9062 0.4640 0.3643 0.059 Uiso 1 1 calc R . .
C2 C 0.6377(4) 0.6727(3) 0.1440(3) 0.0458(6) Uani 1 1 d . . .
C8 C 0.2686(4) 0.2219(3) 0.2908(3) 0.0468(6) Uani 1 1 d . . .
C7 C 0.4406(5) 0.1464(3) 0.3239(3) 0.0542(7) Uani 1 1 d . . .
H7 H 0.4298 0.0488 0.2689 0.065 Uiso 1 1 calc R . .
C3 C 0.9113(5) 0.5510(4) 0.1972(3) 0.0609(8) Uani 1 1 d . . .
H3 H 1.0372 0.5173 0.1801 0.073 Uiso 1 1 calc R . .
C5 C 0.7895(5) 0.0993(4) 0.4568(4) 0.0677(9) Uani 1 1 d . . .
H5A H 0.9340 0.1540 0.4602 0.102 Uiso 1 1 calc GR . .
H5B H 0.7527 0.0076 0.3838 0.102 Uiso 1 1 calc GR . .
H5C H 0.7855 0.0717 0.5434 0.102 Uiso 1 1 calc GR . .
C9 C 0.0756(5) 0.1408(4) 0.1741(3) 0.0735(10) Uani 1 1 d . . .
H9A H -0.0580 0.1539 0.2026 0.110 Uiso 1 1 calc GR . .
H9B H 0.0781 0.0330 0.1501 0.110 Uiso 1 1 calc GR . .
H9C H 0.0838 0.1840 0.0952 0.110 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'
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 180.00(11) 2_666 .
O1 Ni1 O2 91.64(7) . .
O1 Ni1 O2 88.36(7) . 2_666
O1 Ni1 O2 88.36(7) 2_666 .
O1 Ni1 O2 91.64(7) 2_666 2_666
O1 Ni1 N1 89.53(7) . 2_666
O1 Ni1 N1 90.47(7) . .
O1 Ni1 N1 89.53(7) 2_666 .
O1 Ni1 N1 90.47(7) 2_666 2_666
O2 Ni1 O2 180.0 . 2_666
O2 Ni1 N1 87.97(7) 2_666 2_666
O2 Ni1 N1 92.03(7) . 2_666
O2 Ni1 N1 92.03(7) 2_666 .
O2 Ni1 N1 87.97(7) . .
N1 Ni1 N1 180.0 2_666 .
C6 O1 Ni1 124.93(17) . .
C8 O2 Ni1 124.90(17) . .
C1 N1 Ni1 119.45(16) . .
C1 N1 C4 116.6(2) . .
C4 N1 Ni1 123.80(17) . .
C2 N2 C3 115.1(2) . .
O1 C6 C7 125.8(2) . .
O1 C6 C5 114.5(3) . .
C7 C6 C5 119.7(3) . .
N1 C1 H1 119.7 . .
N1 C1 C2 120.7(2) . .
C2 C1 H1 119.7 . .
N1 C4 H4 119.3 . .
N1 C4 C3 121.3(3) . .
C3 C4 H4 119.3 . .
N2 C2 Br1 117.6(2) . .
N2 C2 C1 123.6(2) . .
C1 C2 Br1 118.8(2) . .
O2 C8 C7 125.3(3) . .
O2 C8 C9 115.4(3) . .
C7 C8 C9 119.3(3) . .
C6 C7 C8 126.8(3) . .
C6 C7 H7 116.6 . .
C8 C7 H7 116.6 . .
N2 C3 C4 122.7(3) . .
N2 C3 H3 118.7 . .
C4 C3 H3 118.7 . .
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 2.0046(16) 2_666
Ni1 O1 2.0046(16) .
Ni1 O2 2.0116(17) 2_666
Ni1 O2 2.0116(17) .
Ni1 N1 2.172(2) 2_666
Ni1 N1 2.172(2) .
Br1 C2 1.896(3) .
O1 C6 1.266(3) .
O2 C8 1.263(3) .
N1 C1 1.333(3) .
N1 C4 1.334(3) .
N2 C2 1.318(3) .
N2 C3 1.330(4) .
C6 C7 1.383(4) .
C6 C5 1.519(4) .
C1 H1 0.9300 .
C1 C2 1.377(4) .
C4 H4 0.9300 .
C4 C3 1.375(4) .
C8 C7 1.399(4) .
C8 C9 1.508(4) .
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 3.272(3) 130.8 1_655
C3 H3 O2 0.93 2.80 3.380(3) 121.4 1_655
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 177.35(17)
Ni1 O2 C8 C7 5.6(4)
Ni1 O2 C8 C9 -174.61(19)
Ni1 N1 C1 C2 -175.6(2)
Ni1 N1 C4 C3 174.9(2)
O1 C6 C7 C8 -3.4(4)
O2 C8 C7 C6 2.0(4)
N1 C1 C2 Br1 179.87(19)
N1 C1 C2 N2 0.6(4)
N1 C4 C3 N2 0.5(5)
C1 N1 C4 C3 -0.5(4)
C4 N1 C1 C2 0.0(4)
C2 N2 C3 C4 0.0(5)
C3 N2 C2 Br1 -179.8(2)
C3 N2 C2 C1 -0.5(4)
C5 C6 C7 C8 176.1(3)
C9 C8 C7 C6 -177.8(3)
