#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/55/2205553.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2205553
loop_
_publ_author_name
'Annie Michaud'
'Frédéric-Georges Fontaine'
'Davit Zargarian'
_publ_section_title
;
 Bis[tris(3,5-dimethylpyrazolyl)methane]nickel(II) dibromide
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m784
_journal_page_last               m786
_journal_paper_doi               10.1107/S1600536805009451
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '[Ni (C16 H22 N6)2] Br2'
_chemical_formula_moiety         'C32 H44 N12 Ni 2+ , 2Br -'
_chemical_formula_sum            'C32 H44 Br2 N12 Ni'
_chemical_formula_weight         815.322
_chemical_name_systematic
;
Bis[tris(3,5-dimethylpyrazolyl)methane]nickel(II) dibromide
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL96 (Sheldrick, 1996)'
_cell_angle_alpha                90.00
_cell_angle_beta                 92.5800(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   18.9240(2)
_cell_length_b                   10.9960(10)
_cell_length_c                   8.88210(10)
_cell_measurement_reflns_used    8952
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.88
_cell_measurement_theta_min      4.65
_cell_volume                     1846.39(17)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT '
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker SMART 2K/Platform'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus xray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1245
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11178
_diffrn_reflns_theta_full        72.88
_diffrn_reflns_theta_max         72.87
_diffrn_reflns_theta_min         4.65
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  60
_diffrn_standards_number         88
_exptl_absorpt_coefficient_mu    3.612
_exptl_absorpt_correction_T_max  0.6972
_exptl_absorpt_correction_T_min  0.4470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'translucent pale pink'
_exptl_crystal_density_diffrn    1.4665
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             836.0
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.603
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.070
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_restrained_S_obs      1.114
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0402
_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)+(0.0739P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1105
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                1702
_reflns_number_total             1907
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6391.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               2205553
_cod_database_fobs_code          2205553
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
loop_
_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_type_symbol
Ni 0.0000 0.0000 0.0000 0.0274(2) Uani d S 1 Ni
C11 0.14287(14) 0.0000 -0.1496(3) 0.0292(6) Uani d S 1 C
H11 0.1882 0.0000 -0.1989 0.035 Uiso calc SR 1 H
N1 0.10228(14) 0.0000 0.1050(3) 0.0399(6) Uani d S 1 N
N2 0.15766(13) 0.0000 0.0105(3) 0.0348(5) Uani d S 1 N
C1 0.0871(3) 0.0000 0.3796(5) 0.101(2) Uani d S 1 C
H1A 0.1090 -0.0510 0.4560 0.151 Uiso calc PR 0.50 H
H1B 0.0407 -0.0305 0.3528 0.151 Uiso calc PR 0.50 H
H1C 0.0834 0.0815 0.4173 0.151 Uiso calc PR 0.50 H
C2 0.1312(2) 0.0000 0.2423(4) 0.0543(9) Uani d S 1 C
C3 0.2049(2) 0.0000 0.2390(5) 0.0556(10) Uani d S 1 C
H3 0.2368 0.0000 0.3216 0.067 Uiso calc SR 1 H
C4 0.22085(17) 0.0000 0.0905(4) 0.0471(8) Uani d S 1 C
C5 0.2907(2) 0.0000 0.0190(6) 0.0821(16) Uani d S 1 C
H5A 0.2858 -0.0372 -0.0787 0.123 Uiso calc PR 0.50 H
H5B 0.3244 -0.0450 0.0810 0.123 Uiso calc PR 0.50 H
H5C 0.3069 0.0822 0.0087 0.123 Uiso calc PR 0.50 H
N3 0.03823(9) 0.12830(17) -0.1472(2) 0.0406(5) Uani d . 1 N
N4 0.10484(9) 0.10856(15) -0.1964(2) 0.0325(4) Uani d . 1 N
C6 -0.05222(19) 0.2906(3) -0.1803(5) 0.0876(13) Uani d . 1 C
H6A -0.0858 0.2272 -0.1631 0.131 Uiso calc R 1 H
H6B -0.0675 0.3365 -0.2678 0.131 Uiso calc R 1 H
H6C -0.0488 0.3434 -0.0942 0.131 Uiso calc R 1 H
C7 0.01861(14) 0.2355(2) -0.2051(3) 0.0522(7) Uani d . 1 C
C8 0.07280(15) 0.2840(2) -0.2889(3) 0.0551(7) Uani d . 1 C
H8 0.0719 0.3577 -0.3403 0.066 Uiso calc R 1 H
C9 0.12695(13) 0.2030(2) -0.2809(3) 0.0418(5) Uani d . 1 C
C10 0.19805(15) 0.2092(3) -0.3439(4) 0.0619(8) Uani d . 1 C
H10A 0.2332 0.2181 -0.2632 0.093 Uiso calc R 1 H
H10B 0.2002 0.2776 -0.4106 0.093 Uiso calc R 1 H
H10C 0.2069 0.1358 -0.3986 0.093 Uiso calc R 1 H
Br 0.658821(18) 0.0000 0.43123(4) 0.04606(17) Uani d S 1 Br
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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'
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
N3 Ni N3 6 . 85.65(11) y
N3 Ni N3 6 2 180.0 y
N3 Ni N3 . 2 94.35(11) y
N3 Ni N3 6 5 94.35(11) ?
N3 Ni N3 . 5 180.0 ?
N3 Ni N3 2 5 85.65(11) ?
N3 Ni N1 6 . 86.53(7) ?
N3 Ni N1 . . 86.53(7) y
N3 Ni N1 2 . 93.47(7) y
N3 Ni N1 5 . 93.47(7) ?
N3 Ni N1 6 5 93.47(7) ?
N3 Ni N1 . 5 93.47(7) ?
N3 Ni N1 2 5 86.53(7) ?
N3 Ni N1 5 5 86.53(7) ?
N1 Ni N1 . 5 180.0 y
N2 C11 N4 . . 110.91(15) ?
N2 C11 N4 . 6 110.91(15) ?
N4 C11 N4 . 6 111.4(2) ?
N2 C11 H11 . . 107.8 ?
N4 C11 H11 . . 107.8 ?
N4 C11 H11 6 . 107.8 ?
C2 N1 N2 . . 105.6(3) ?
C2 N1 Ni . . 138.2(2) ?
N2 N1 Ni . . 116.14(19) ?
C4 N2 N1 . . 111.0(3) ?
C4 N2 C11 . . 130.0(3) ?
N1 N2 C11 . . 119.0(2) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 C3 . . 110.8(3) ?
N1 C2 C1 . . 121.8(3) ?
C3 C2 C1 . . 127.4(4) ?
C4 C3 C2 . . 106.5(3) ?
C4 C3 H3 . . 126.7 ?
C2 C3 H3 . . 126.7 ?
N2 C4 C3 . . 106.0(3) ?
N2 C4 C5 . . 123.5(3) ?
C3 C4 C5 . . 130.5(3) ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C7 N3 N4 . . 105.14(17) ?
C7 N3 Ni . . 138.22(16) ?
N4 N3 Ni . . 116.45(12) ?
C9 N4 N3 . . 111.48(17) ?
C9 N4 C11 . . 128.95(19) ?
N3 N4 C11 . . 119.49(17) ?
C7 C6 H6A . . 109.5 ?
C7 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C7 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
N3 C7 C8 . . 110.1(2) ?
N3 C7 C6 . . 122.5(2) ?
C8 C7 C6 . . 127.4(2) ?
C9 C8 C7 . . 107.0(2) ?
C9 C8 H8 . . 126.5 ?
C7 C8 H8 . . 126.5 ?
C8 C9 N4 . . 106.3(2) ?
C8 C9 C10 . . 130.3(2) ?
N4 C9 C10 . . 123.5(2) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
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
Ni N3 6 2.0753(17) ?
Ni N3 . 2.0754(17) y
Ni N3 2 2.0754(17) ?
Ni N3 5 2.0754(17) ?
Ni N1 . 2.110(3) y
Ni N1 5 2.110(3) ?
C11 N2 . 1.438(4) y
C11 N4 . 1.445(2) y
C11 N4 6 1.445(2) ?
C11 H11 . 0.9800 ?
N1 C2 . 1.314(4) y
N1 N2 . 1.372(3) y
N2 C4 . 1.363(4) y
C1 C2 . 1.509(6) y
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.395(5) y
C3 C4 . 1.366(5) y
C3 H3 . 0.9300 ?
C4 C5 . 1.493(5) y
C5 H5A . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
N3 C7 . 1.332(3) y
N3 N4 . 1.370(2) y
N4 C9 . 1.358(3) y
C6 C7 . 1.496(4) y
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
C6 H6C . 0.9600 ?
C7 C8 . 1.399(3) y
C8 C9 . 1.357(3) y
C8 H8 . 0.9300 ?
C9 C10 . 1.482(3) y
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
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
N3 Ni N1 C2 6 -137.08(6)
N3 Ni N1 C2 . 137.08(6)
N3 Ni N1 C2 2 42.92(6)
N3 Ni N1 C2 5 -42.92(6)
N3 Ni N1 N2 6 42.92(6)
N3 Ni N1 N2 . -42.92(6)
N3 Ni N1 N2 2 -137.08(6)
N3 Ni N1 N2 5 137.08(6)
C2 N1 N2 C4 . 0.0
Ni N1 N2 C4 . 180.0
C2 N1 N2 C11 . 180.0
Ni N1 N2 C11 . 0.0
N4 C11 N2 C4 . -117.85(16)
N4 C11 N2 C4 6 117.85(16)
N4 C11 N2 N1 . 62.15(16)
N4 C11 N2 N1 6 -62.15(16)
N2 N1 C2 C3 . 0.0
Ni N1 C2 C3 . 180.0
N2 N1 C2 C1 . 180.0
Ni N1 C2 C1 . 0.0
N1 C2 C3 C4 . 0.0
C1 C2 C3 C4 . 180.0
N1 N2 C4 C3 . 0.0
C11 N2 C4 C3 . 180.0
N1 N2 C4 C5 . 180.0
C11 N2 C4 C5 . 0.0
C2 C3 C4 N2 . 0.0
C2 C3 C4 C5 . 180.0
N1 Ni N3 C7 . -132.5(3)
N1 Ni N3 C7 5 47.5(3)
N1 Ni N3 N4 . 41.38(16)
N1 Ni N3 N4 5 -138.62(16)
C7 N3 N4 C9 . 1.3(3)
Ni N3 N4 C9 . -174.53(16)
C7 N3 N4 C11 . 178.2(2)
Ni N3 N4 C11 . 2.4(3)
N2 C11 N4 C9 . 111.9(3)
N4 C11 N4 C9 6 -124.0(2)
N2 C11 N4 N3 . -64.4(3)
N4 C11 N4 N3 6 59.6(3)
N4 N3 C7 C8 . -0.7(3)
Ni N3 C7 C8 . 173.6(2)
N4 N3 C7 C6 . 178.9(3)
Ni N3 C7 C6 . -6.7(5)
N3 C7 C8 C9 . -0.1(4)
C6 C7 C8 C9 . -179.7(4)
C7 C8 C9 N4 . 0.8(3)
C7 C8 C9 C10 . -177.7(3)
N3 N4 C9 C8 . -1.3(3)
C11 N4 C9 C8 . -177.9(2)
N3 N4 C9 C10 . 177.3(2)
C11 N4 C9 C10 . 0.7(4)
