#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/08/2220808.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_2220808
loop_
_publ_author_name
'Yu, Ming-Ming'
'Xu, Hong'
'Shi, Qiu-Zhi'
'Wei, Ying-Nai'
'Li, Zhan-Xian'
_publ_section_title
;{6,6'-Dimethoxy-2,2'-[4-bromo-o-phenylenebis(nitrilomethylidyne)]diphenolato}nickel(II)
 methanol solvate
;
_journal_coeditor_code           HG2467
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m225
_journal_paper_doi               10.1107/S1600536809002104
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Ni (C22 H17 Br N2 O4)], C H4 O'
_chemical_formula_moiety         'C22 H17 Br N2 Ni O4, C H4 O'
_chemical_formula_sum            'C23 H21 Br N2 Ni O5'
_chemical_formula_weight         544.04
_chemical_name_systematic
;
{6,6'-Dimethoxy-2,2'-[4-bromo-o-
phenylenebis(nitrilomethylidyne)]diphenolato}nickel(II) methanol solvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.042(2)
_cell_angle_beta                 96.971(3)
_cell_angle_gamma                95.932(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4991(12)
_cell_length_b                   11.8367(18)
_cell_length_c                   12.5428(19)
_cell_measurement_reflns_used    4086
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      1.70
_cell_volume                     1056.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5680
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    2.849
_exptl_absorpt_correction_T_max  0.8946
_exptl_absorpt_correction_T_min  0.7262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.614
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0951P)²+0.0167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1612
_reflns_number_gt                3123
_reflns_number_total             4086
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2467.cif
_cod_data_source_block           I
_cod_database_code               2220808
_cod_database_fobs_code          2220808
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C3 0.8652(7) 0.0691(4) 0.3998(4) 0.0510(12) Uani d . 1 . .
H H3 0.8869 -0.0085 0.3912 0.061 Uiso calc R 1 . .
C C4 0.7842(7) 0.1013(4) 0.3070(4) 0.0471(11) Uani d . 1 . .
C C5 0.7428(6) 0.2142(4) 0.3178(4) 0.0443(10) Uani d . 1 . .
H H5 0.6876 0.2363 0.2573 0.053 Uiso calc R 1 . .
C C6 0.7873(5) 0.2926(4) 0.4224(3) 0.0357(9) Uani d . 1 . .
C C1 0.8774(6) 0.2549(4) 0.5093(3) 0.0370(9) Uani d . 1 . .
C C7 1.0169(6) 0.3214(4) 0.6961(4) 0.0393(10) Uani d . 1 . .
H H7 1.0357 0.2435 0.6888 0.047 Uiso calc R 1 . .
C C8 1.0843(6) 0.4041(4) 0.7991(4) 0.0413(10) Uani d . 1 . .
C C9 1.1868(7) 0.3673(5) 0.8839(4) 0.0521(12) Uani d . 1 . .
H H9 1.2006 0.2879 0.8717 0.063 Uiso calc R 1 . .
C C10 1.2639(7) 0.4443(5) 0.9811(4) 0.0569(13) Uani d . 1 . .
H H10 1.3277 0.4176 1.0358 0.068 Uiso calc R 1 . .
C C11 1.2491(7) 0.5644(5) 1.0008(4) 0.0552(13) Uani d . 1 . .
H H11 1.3035 0.6174 1.0683 0.066 Uiso calc R 1 . .
C C12 1.1539(7) 0.6045(4) 0.9200(4) 0.0477(11) Uani d . 1 . .
C C13 1.0650(6) 0.5251(4) 0.8169(3) 0.0397(10) Uani d . 1 . .
C C14 1.2135(11) 0.8037(5) 1.0330(5) 0.093(2) Uani d . 1 . .
H H14B 1.3419 0.8015 1.0451 0.139 Uiso calc R 1 . .
H H14A 1.1605 0.7842 1.0930 0.139 Uiso calc R 1 . .
H H14C 1.1918 0.8815 1.0304 0.139 Uiso calc R 1 . .
C C15 0.6634(5) 0.4582(4) 0.3866(3) 0.0368(9) Uani d . 1 . .
H H15 0.6145 0.4089 0.3162 0.044 Uiso calc R 1 . .
C C16 0.6301(5) 0.5774(4) 0.4112(3) 0.0371(9) Uani d . 1 . .
C C17 0.5302(6) 0.6144(5) 0.3271(4) 0.0489(11) Uani d . 1 . .
H H17 0.4833 0.5601 0.2588 0.059 Uiso calc R 1 . .
C C18 0.5021(7) 0.7289(5) 0.3451(4) 0.0517(12) Uani d . 1 . .
H H18 0.4382 0.7527 0.2883 0.062 Uiso calc R 1 . .
C C19 0.5680(6) 0.8118(4) 0.4482(4) 0.0503(12) Uani d . 1 . .
H H19 0.5483 0.8900 0.4591 0.060 Uiso calc R 1 . .
C C20 0.6611(6) 0.7783(4) 0.5328(4) 0.0395(10) Uani d . 1 . .
C C21 0.6960(5) 0.6590(4) 0.5160(3) 0.0343(9) Uani d . 1 . .
C C22 0.7016(8) 0.9703(4) 0.6604(4) 0.0581(13) Uani d . 1 . .
H H22A 0.7580 1.0111 0.7354 0.087 Uiso calc R 1 . .
H H22B 0.5737 0.9744 0.6532 0.087 Uiso calc R 1 . .
H H22C 0.7536 1.0067 0.6091 0.087 Uiso calc R 1 . .
C C23 0.7099(11) 0.8110(6) 0.8879(5) 0.087(2) Uani d . 1 . .
H H23A 0.8401 0.8205 0.8984 0.131 Uiso calc R 1 . .
H H23B 0.6687 0.8131 0.9578 0.131 Uiso calc R 1 . .
H H23C 0.6685 0.8739 0.8607 0.131 Uiso calc R 1 . .
C C2 0.9109(5) 0.1459(3) 0.4982(3) 0.0303(8) Uani d . 1 . .
H H2 0.9658 0.1238 0.5588 0.036 Uiso calc R 1 . .
N N2 0.7574(4) 0.4124(3) 0.4553(3) 0.0349(8) Uani d . 1 . .
N N3 0.9301(4) 0.3451(3) 0.6101(3) 0.0343(7) Uani d . 1 . .
O O1 0.7893(4) 0.6322(2) 0.5995(2) 0.0385(7) Uani d . 1 . .
O O2 0.9756(4) 0.5679(3) 0.7446(2) 0.0416(7) Uani d . 1 . .
O O3 1.1343(6) 0.7207(3) 0.9303(3) 0.0678(11) Uani d . 1 . .
O O4 0.7307(5) 0.8499(3) 0.6360(3) 0.0501(8) Uani d . 1 . .
O O5 0.6410(5) 0.7031(3) 0.8107(3) 0.0665(10) Uani d . 1 . .
H H5' 0.6896 0.6966 0.7546 0.100 Uiso calc R 1 . .
Ni Ni1 0.86214(7) 0.48899(4) 0.60223(4) 0.03314(19) Uani d . 1 . .
Br Br1 0.73229(10) -0.01370(5) 0.16760(5) 0.0796(3) Uani d . 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
C2 C3 C4 . . 121.5(4) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
C5 C4 C3 . . 120.8(4) ?
C5 C4 Br1 . . 120.8(4) ?
C3 C4 Br1 . . 118.4(4) ?
C6 C5 C4 . . 116.7(4) ?
C6 C5 H5 . . 121.6 ?
C4 C5 H5 . . 121.6 ?
C5 C6 C1 . . 118.7(4) ?
C5 C6 N2 . . 127.6(4) ?
C1 C6 N2 . . 113.7(3) ?
C2 C1 C6 . . 123.6(4) ?
C2 C1 N3 . . 122.6(4) ?
C6 C1 N3 . . 113.9(4) ?
N3 C7 C8 . . 125.1(4) ?
N3 C7 H7 . . 117.4 ?
C8 C7 H7 . . 117.4 ?
C7 C8 C13 . . 121.2(4) ?
C7 C8 C9 . . 119.1(4) ?
C13 C8 C9 . . 119.5(4) ?
C10 C9 C8 . . 121.5(5) ?
C10 C9 H9 . . 119.3 ?
C8 C9 H9 . . 119.3 ?
C9 C10 C11 . . 120.5(4) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
C12 C11 C10 . . 120.0(5) ?
C12 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
O3 C12 C11 . . 124.5(4) ?
O3 C12 C13 . . 114.2(4) ?
C11 C12 C13 . . 121.3(5) ?
O2 C13 C8 . . 124.3(4) ?
O2 C13 C12 . . 118.5(4) ?
C8 C13 C12 . . 117.2(4) ?
O3 C14 H14B . . 109.5 ?
O3 C14 H14A . . 109.5 ?
H14B C14 H14A . . 109.5 ?
O3 C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
N2 C15 C16 . . 125.1(4) ?
N2 C15 H15 . . 117.5 ?
C16 C15 H15 . . 117.5 ?
C17 C16 C21 . . 119.7(4) ?
C17 C16 C15 . . 118.3(4) ?
C21 C16 C15 . . 122.0(4) ?
C18 C17 C16 . . 120.4(4) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C17 C18 C19 . . 120.9(4) ?
C17 C18 H18 . . 119.6 ?
C19 C18 H18 . . 119.6 ?
C20 C19 C18 . . 120.4(4) ?
C20 C19 H19 . . 119.8 ?
C18 C19 H19 . . 119.8 ?
O4 C20 C19 . . 125.8(4) ?
O4 C20 C21 . . 114.0(4) ?
C19 C20 C21 . . 120.2(4) ?
O1 C21 C16 . . 123.9(4) ?
O1 C21 C20 . . 117.6(4) ?
C16 C21 C20 . . 118.5(4) ?
O4 C22 H22A . . 109.5 ?
O4 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
O4 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
O5 C23 H23A . . 109.5 ?
O5 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
O5 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C3 C2 C1 . . 118.5(4) ?
C3 C2 H2 . . 120.7 ?
C1 C2 H2 . . 120.7 ?
C15 N2 C6 . . 121.1(3) ?
C15 N2 Ni1 . . 126.4(3) ?
C6 N2 Ni1 . . 112.5(3) ?
C7 N3 C1 . . 119.6(4) ?
C7 N3 Ni1 . . 127.2(3) ?
C1 N3 Ni1 . . 113.2(3) ?
C21 O1 Ni1 . . 127.9(3) ?
C13 O2 Ni1 . . 128.0(3) ?
C12 O3 C14 . . 116.9(4) ?
C20 O4 C22 . . 117.9(4) ?
C23 O5 H5' . . 109.5 ?
O2 Ni1 O1 . . 84.82(12) yes
O2 Ni1 N3 . . 93.97(14) yes
O1 Ni1 N3 . . 177.54(13) ?
O2 Ni1 N2 . . 177.07(14) ?
O1 Ni1 N2 . . 94.73(14) yes
N3 Ni1 N2 . . 86.59(15) yes
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
C3 C2 . 1.310(6) ?
C3 C4 . 1.406(7) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.380(7) ?
C4 Br1 . 1.885(4) ?
C5 C6 . 1.376(6) ?
C5 H5 . 0.9300 ?
C6 C1 . 1.406(6) ?
C6 N2 . 1.419(5) ?
C1 C2 . 1.316(6) ?
C1 N3 . 1.409(5) ?
C7 N3 . 1.301(5) ?
C7 C8 . 1.402(6) ?
C7 H7 . 0.9300 ?
C8 C13 . 1.417(6) ?
C8 C9 . 1.423(6) ?
C9 C10 . 1.339(7) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.397(7) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.381(6) ?
C11 H11 . 0.9300 ?
C12 O3 . 1.373(6) ?
C12 C13 . 1.425(6) ?
C13 O2 . 1.299(5) ?
C14 O3 . 1.419(6) ?
C14 H14B . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14C . 0.9600 ?
C15 N2 . 1.307(5) ?
C15 C16 . 1.419(6) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.408(6) ?
C16 C21 . 1.411(6) ?
C17 C18 . 1.358(7) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.401(7) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.366(6) ?
C19 H19 . 0.9300 ?
C20 O4 . 1.357(5) ?
C20 C21 . 1.429(6) ?
C21 O1 . 1.315(5) ?
C22 O4 . 1.423(5) ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
C23 O5 . 1.392(7) ?
C23 H23A . 0.9600 ?
C23 H23B . 0.9600 ?
C23 H23C . 0.9600 ?
C2 H2 . 0.9300 ?
N2 Ni1 . 1.862(3) yes
N3 Ni1 . 1.851(3) yes
O1 Ni1 . 1.841(3) yes
O2 Ni1 . 1.840(3) yes
O5 H5' . 0.8200 ?
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
O5 H5' O1 . 0.8200 2.1510 2.952(4) 164.84
C15 H15 O5 2_666 0.9300 2.3673 3.203(5) 149.35
C23 H23B Br1 1_566 0.9600 2.8369 3.556(6) 132.47
