#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/72/2227291.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_2227291
loop_
_publ_author_name
'He, XiuLi'
'Shi, Feifei'
'Lu, Yonghong'
_publ_section_title
;
 (meso-5,7,7,12,14,14-Hexamethyl-1,4,8,11-tetraazacyclotetradeca-4,11-diene)nickel(II)
 dibromide dihydrate
;
_journal_coeditor_code           BX2296
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1339
_journal_paper_doi               10.1107/S1600536810033714
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Ni (C16 H32 N4)] Br2, 2H2 O'
_chemical_formula_moiety         'C16 H32 N4 Ni 2+, 2(Br -), 2(H2 O)'
_chemical_formula_sum            'C16 H36 Br2 N4 Ni O2'
_chemical_formula_weight         535.02
_chemical_name_systematic
;
(meso-5,7,7,12,14,14-Hexamethyl-1,4,8,11-tetraazacyclotetradeca-4,11-
diene)nickel(II) dibromide dihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.72(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.0349(16)
_cell_length_b                   15.619(3)
_cell_length_c                   8.9355(18)
_cell_measurement_reflns_used    3476
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4758
_cell_measurement_theta_min      2.3173
_cell_volume                     1105.3(4)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       'thin-slice ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11266
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.41
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.509
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.8310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.2700
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.743
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         2531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0317P)²+1.6713P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0985
_reflns_number_gt                1995
_reflns_number_total             2531
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bx2296.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227291
_cod_database_fobs_code          2227291
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni1 0.5000 0.5000 0.5000 0.02894(16) Uani d S 1 . .
Br Br1 0.69586(6) 0.10330(3) 0.63849(6) 0.06334(18) Uani d . 1 . .
C C1 0.8076(5) 0.5280(2) 0.7876(4) 0.0410(8) Uani d . 1 . .
H H1B 0.9228 0.5334 0.8406 0.061 Uiso calc R 1 . .
H H1C 0.7344 0.5312 0.8633 0.061 Uiso calc R 1 . .
C C2 0.7698(4) 0.6042(2) 0.6830(4) 0.0362(8) Uani d . 1 . .
C C3 0.5246(5) 0.6761(2) 0.5232(5) 0.0546(11) Uani d . 1 . .
H H3A 0.5877 0.6831 0.4405 0.065 Uiso calc R 1 . .
H H3B 0.5384 0.7273 0.5854 0.065 Uiso calc R 1 . .
C C4 0.3413(5) 0.6610(2) 0.4621(5) 0.0536(11) Uani d . 1 . .
H H4A 0.2748 0.6656 0.5429 0.064 Uiso calc R 1 . .
H H4B 0.3003 0.7030 0.3846 0.064 Uiso calc R 1 . .
C C5 0.2117(4) 0.5591(2) 0.2827(4) 0.0343(7) Uani d . 1 . .
C C6 0.8765(5) 0.6034(3) 0.5571(5) 0.0503(10) Uani d . 1 . .
H H6A 0.8525 0.5525 0.4972 0.075 Uiso calc R 1 . .
H H6B 0.9941 0.6044 0.6013 0.075 Uiso calc R 1 . .
H H6C 0.8503 0.6528 0.4937 0.075 Uiso calc R 1 . .
C C7 0.8061(5) 0.6849(3) 0.7812(5) 0.0561(11) Uani d . 1 . .
H H7A 0.7833 0.7348 0.7184 0.084 Uiso calc R 1 . .
H H7B 0.9225 0.6851 0.8290 0.084 Uiso calc R 1 . .
H H7C 0.7353 0.6853 0.8576 0.084 Uiso calc R 1 . .
C C8 0.0896(5) 0.6244(3) 0.2077(5) 0.0528(10) Uani d . 1 . .
H H8A 0.0147 0.5984 0.1252 0.079 Uiso calc R 1 . .
H H8B 0.1504 0.6702 0.1695 0.079 Uiso calc R 1 . .
H H8C 0.0252 0.6468 0.2802 0.079 Uiso calc R 1 . .
N N1 0.5857(3) 0.60021(16) 0.6151(3) 0.0332(6) Uani d . 1 . .
H H1A 0.5300 0.6015 0.6957 0.040 Uiso calc R 1 . .
N N2 0.3276(3) 0.57404(17) 0.3970(3) 0.0333(6) Uani d . 1 . .
O O1 0.6240(6) 0.8913(2) 0.6616(5) 0.0923(12) Uani d . 1 . .
H H1E 0.6525 0.9438 0.6665 0.111 Uiso d R 1 . .
H H1F 0.5421 0.8854 0.5885 0.111 Uiso d R 1 . .
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'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 Ni1 N2 . 3_666 180.0000(10) ?
N2 Ni1 N1 . . 86.01(12) ?
N2 Ni1 N1 3_666 . 93.99(12) ?
N2 Ni1 N1 . 3_666 93.99(12) ?
N2 Ni1 N1 3_666 3_666 86.01(12) ?
N1 Ni1 N1 . 3_666 180.0 ?
C5 C1 C2 3_666 . 117.5(3) ?
C5 C1 H1B 3_666 . 107.9 ?
C2 C1 H1B . . 107.9 ?
C5 C1 H1C 3_666 . 107.9 ?
C2 C1 H1C . . 107.9 ?
H1B C1 H1C . . 107.2 ?
N1 C2 C1 . . 107.3(3) ?
N1 C2 C6 . . 109.9(3) ?
C1 C2 C6 . . 111.7(3) ?
N1 C2 C7 . . 110.1(3) ?
C1 C2 C7 . . 107.1(3) ?
C6 C2 C7 . . 110.6(3) ?
N1 C3 C4 . . 106.8(3) ?
N1 C3 H3A . . 110.4 ?
C4 C3 H3A . . 110.4 ?
N1 C3 H3B . . 110.4 ?
C4 C3 H3B . . 110.4 ?
H3A C3 H3B . . 108.6 ?
N2 C4 C3 . . 106.9(3) ?
N2 C4 H4A . . 110.3 ?
C3 C4 H4A . . 110.3 ?
N2 C4 H4B . . 110.3 ?
C3 C4 H4B . . 110.3 ?
H4A C4 H4B . . 108.6 ?
N2 C5 C8 . . 124.5(3) ?
N2 C5 C1 . 3_666 120.7(3) ?
C8 C5 C1 . 3_666 114.8(3) ?
C2 C6 H6A . . 109.5 ?
C2 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C2 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C2 C7 H7A . . 109.5 ?
C2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C5 C8 H8A . . 109.5 ?
C5 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C5 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C3 N1 C2 . . 113.8(3) ?
C3 N1 Ni1 . . 107.4(2) ?
C2 N1 Ni1 . . 119.1(2) ?
C3 N1 H1A . . 105.1 ?
C2 N1 H1A . . 105.1 ?
Ni1 N1 H1A . . 105.1 ?
C5 N2 C4 . . 118.5(3) ?
C5 N2 Ni1 . . 129.9(2) ?
C4 N2 Ni1 . . 111.5(2) ?
H1E O1 H1F . . 108.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 N2 . 1.916(3) ?
Ni1 N2 3_666 1.916(3) ?
Ni1 N1 . 1.934(3) ?
Ni1 N1 3_666 1.934(3) ?
C1 C5 3_666 1.494(5) ?
C1 C2 . 1.513(5) ?
C1 H1B . 0.9700 ?
C1 H1C . 0.9700 ?
C2 N1 . 1.503(4) ?
C2 C6 . 1.525(5) ?
C2 C7 . 1.535(5) ?
C3 N1 . 1.477(4) ?
C3 C4 . 1.501(5) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 N2 . 1.475(5) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 N2 . 1.282(4) ?
C5 C8 . 1.494(5) ?
C5 C1 3_666 1.494(5) ?
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
C6 H6C . 0.9600 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
N1 H1A . 0.9100 ?
O1 H1E . 0.8500 ?
O1 H1F . 0.8500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A Br1 2_656 0.91 2.53 3.413(3) 164 yes
O1 H1E Br1 1_565 0.85 2.53 3.374(3) 169 yes
O1 H1F Br1 3_666 0.85 2.55 3.388(5) 170 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 C1 C2 N1 3_666 . . . 64.1(4) ?
C5 C1 C2 C6 3_666 . . . -56.4(4) ?
C5 C1 C2 C7 3_666 . . . -177.6(3) ?
N1 C3 C4 N2 . . . . -48.4(5) ?
C4 C3 N1 C2 . . . . 179.0(3) ?
C4 C3 N1 Ni1 . . . . 45.0(4) ?
C1 C2 N1 C3 . . . . 173.5(3) ?
C6 C2 N1 C3 . . . . -64.9(4) ?
C7 C2 N1 C3 . . . . 57.2(4) ?
C1 C2 N1 Ni1 . . . . -58.4(3) ?
C6 C2 N1 Ni1 . . . . 63.2(3) ?
C7 C2 N1 Ni1 . . . . -174.7(3) ?
N2 Ni1 N1 C3 . . . . -23.2(3) ?
N2 Ni1 N1 C3 3_666 . . . 156.8(3) ?
N1 Ni1 N1 C3 3_666 . . . -15E1(10) ?
N2 Ni1 N1 C2 . . . . -154.2(3) ?
N2 Ni1 N1 C2 3_666 . . . 25.8(3) ?
N1 Ni1 N1 C2 3_666 . . . 8E1(10) ?
C8 C5 N2 C4 . . . . 1.2(5) ?
C1 C5 N2 C4 3_666 . . . 180.0(3) ?
C8 C5 N2 Ni1 . . . . -176.6(3) ?
C1 C5 N2 Ni1 3_666 . . . 2.2(5) ?
C3 C4 N2 C5 . . . . -148.4(4) ?
C3 C4 N2 Ni1 . . . . 29.8(4) ?
N2 Ni1 N2 C5 3_666 . . . -7E1(10) ?
N1 Ni1 N2 C5 . . . . 173.9(3) ?
N1 Ni1 N2 C5 3_666 . . . -6.1(3) ?
N2 Ni1 N2 C4 3_666 . . . 12E1(10) ?
N1 Ni1 N2 C4 . . . . -4.0(3) ?
N1 Ni1 N2 C4 3_666 . . . 176.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079546
