#------------------------------------------------------------------------------
#$Date: 2023-01-13 10:50:19 +0200 (Fri, 13 Jan 2023) $
#$Revision: 280331 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106465.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_8106465
loop_
_publ_author_name
'Ha, Kwang'
_publ_section_title
;
 Crystal structure of
 trans-dibromido(1,4,8,11-tetraazacyclotetradecane)nickel(II),
 C10H24Br2N4Ni
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              153
_journal_page_last               154
_journal_paper_doi               10.1515/ncrs-2016-0205
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C10 H24 Br2 N4 Ni'
_chemical_formula_sum            'C10 H24 Br2 N4 Ni'
_chemical_formula_weight         418.86
_chemical_name_systematic
;
trans-Dibromido(1,4,8,11-tetraazacyclotetradecane)nickel(II)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 109.1167(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.9551(4)
_cell_length_b                   12.6275(7)
_cell_length_c                   8.7343(4)
_cell_measurement_reflns_used    7563
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      28.09
_cell_measurement_theta_min      2.95
_cell_volume                     724.79(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23002
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_min         2.949
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    6.837
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_description       stick
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     79
_refine_ls_number_reflns         1810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0226
_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)+(0.0073P)²+0.6054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0413
_refine_ls_wR_factor_ref         0.0439
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1556
_reflns_number_total             1810
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0205_suppl.cif
_cod_data_source_block           NiBr2(cyclam)
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8106465
_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.
;
_shelx_estimated_absorpt_t_min   0.389
_shelx_estimated_absorpt_t_max   0.726
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.0000 0.5000 0.5000 0.01629(9) Uani 1 2 d S . P . .
Br1 Br -0.20782(3) 0.47376(2) 0.70838(3) 0.02400(7) Uani 1 1 d . . . . .
N1 N 0.0476(3) 0.65389(13) 0.5815(2) 0.0193(4) Uani 1 1 d . . . . .
H1 H -0.0316 0.6637 0.6561 0.023 Uiso 1 1 calc R U . . .
N2 N 0.2760(3) 0.46927(14) 0.67581(19) 0.0182(4) Uani 1 1 d . . . . .
H2 H 0.3790 0.4691 0.6199 0.022 Uiso 1 1 calc R U . . .
C1 C 0.2651(3) 0.66118(17) 0.6817(3) 0.0227(5) Uani 1 1 d . . . . .
H1A H 0.2878 0.7241 0.7511 0.027 Uiso 1 1 calc R U . . .
H1B H 0.3498 0.6672 0.6118 0.027 Uiso 1 1 calc R U . . .
C2 C 0.3221(3) 0.56225(18) 0.7850(2) 0.0230(4) Uani 1 1 d . . . . .
H2A H 0.4672 0.5635 0.8485 0.028 Uiso 1 1 calc R U . . .
H2B H 0.2440 0.5586 0.8601 0.028 Uiso 1 1 calc R U . . .
C3 C 0.2970(3) 0.36721(18) 0.7611(3) 0.0244(5) Uani 1 1 d . . . . .
H3A H 0.2071 0.3664 0.8271 0.029 Uiso 1 1 calc R U . . .
H3B H 0.4373 0.3594 0.8340 0.029 Uiso 1 1 calc R U . . .
C4 C 0.2440(3) 0.27415(17) 0.6430(3) 0.0258(5) Uani 1 1 d . . . . .
H4A H 0.3224 0.2812 0.5686 0.031 Uiso 1 1 calc R U . . .
H4B H 0.2882 0.2087 0.7048 0.031 Uiso 1 1 calc R U . . .
C5 C 0.0196(3) 0.26272(17) 0.5425(3) 0.0248(5) Uani 1 1 d . . . . .
H5A H -0.0026 0.1933 0.4895 0.030 Uiso 1 1 calc R U . . .
H5B H -0.0627 0.2661 0.6145 0.030 Uiso 1 1 calc R U . . .
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'
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
N1 Ni1 N1 180.0 . 3_566
N1 Ni1 N2 85.13(7) . .
N1 Ni1 N2 94.87(7) 3_566 .
N1 Ni1 N2 94.87(7) . 3_566
N1 Ni1 N2 85.13(7) 3_566 3_566
N2 Ni1 N2 180.0 . 3_566
N1 Ni1 Br1 93.23(5) . 3_566
N1 Ni1 Br1 86.77(5) 3_566 3_566
N2 Ni1 Br1 87.22(5) . 3_566
N2 Ni1 Br1 92.78(5) 3_566 3_566
N1 Ni1 Br1 86.77(5) . .
N1 Ni1 Br1 93.23(5) 3_566 .
N2 Ni1 Br1 92.78(5) . .
N2 Ni1 Br1 87.22(5) 3_566 .
Br1 Ni1 Br1 180.0 3_566 .
C5 N1 C1 114.01(16) 3_566 .
C5 N1 Ni1 116.38(13) 3_566 .
C1 N1 Ni1 106.29(12) . .
C5 N1 H1 106.5 3_566 .
C1 N1 H1 106.5 . .
Ni1 N1 H1 106.5 . .
C3 N2 C2 113.83(16) . .
C3 N2 Ni1 117.06(13) . .
C2 N2 Ni1 106.40(12) . .
C3 N2 H2 106.3 . .
C2 N2 H2 106.3 . .
Ni1 N2 H2 106.3 . .
N1 C1 C2 108.51(17) . .
N1 C1 H1A 110.0 . .
C2 C1 H1A 110.0 . .
N1 C1 H1B 110.0 . .
C2 C1 H1B 110.0 . .
H1A C1 H1B 108.4 . .
N2 C2 C1 108.13(16) . .
N2 C2 H2A 110.1 . .
C1 C2 H2A 110.1 . .
N2 C2 H2B 110.1 . .
C1 C2 H2B 110.1 . .
H2A C2 H2B 108.4 . .
N2 C3 C4 111.72(17) . .
N2 C3 H3A 109.3 . .
C4 C3 H3A 109.3 . .
N2 C3 H3B 109.3 . .
C4 C3 H3B 109.3 . .
H3A C3 H3B 107.9 . .
C5 C4 C3 115.88(18) . .
C5 C4 H4A 108.3 . .
C3 C4 H4A 108.3 . .
C5 C4 H4B 108.3 . .
C3 C4 H4B 108.3 . .
H4A C4 H4B 107.4 . .
N1 C5 C4 111.95(17) 3_566 .
N1 C5 H5A 109.2 3_566 .
C4 C5 H5A 109.2 . .
N1 C5 H5B 109.2 3_566 .
C4 C5 H5B 109.2 . .
H5A C5 H5B 107.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N1 2.0586(17) .
Ni1 N1 2.0586(17) 3_566
Ni1 N2 2.0648(16) .
Ni1 N2 2.0648(16) 3_566
Ni1 Br1 2.6898(2) 3_566
Ni1 Br1 2.6898(2) .
N1 C5 1.473(3) 3_566
N1 C1 1.482(3) .
N1 H1 0.9900 .
N2 C3 1.472(3) .
N2 C2 1.480(3) .
N2 H2 0.9900 .
C1 C2 1.516(3) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C3 C4 1.527(3) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C4 C5 1.526(3) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C5 N1 1.473(3) 3_566
C5 H5A 0.9800 .
C5 H5B 0.9800 .
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
N1 H1 Br1 0.99 2.80 3.2939(17) 111.6 .
N2 H2 Br1 0.99 2.72 3.5074(17) 136.6 1_655
N2 H2 Br1 0.99 2.81 3.3106(16) 111.6 3_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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C5 N1 C1 C2 -171.19(17) 3_566 . . .
Ni1 N1 C1 C2 -41.63(18) . . . .
C3 N2 C2 C1 -171.86(17) . . . .
Ni1 N2 C2 C1 -41.44(18) . . . .
N1 C1 C2 N2 56.9(2) . . . .
C2 N2 C3 C4 178.91(17) . . . .
Ni1 N2 C3 C4 54.0(2) . . . .
N2 C3 C4 C5 -70.2(2) . . . .
C3 C4 C5 N1 71.2(2) . . . 3_566
