#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/98/2239808.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_2239808
loop_
_publ_author_name
'Bahron, Hadariah'
'Tajuddin, Amalina Mohd'
'Ibrahim, Wan Nazihah Wan'
'Fun, Hoong-Kun'
'Chantrapromma, Suchada'
_publ_section_title
;
 Crystal structure of
 bis{2-[(E)-(4-methoxylbenzyl)iminomethyl]phenolato-κ²N,O¹}nickel(II)
;
_journal_coeditor_code           SJ5419
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              104
_journal_page_last               106
_journal_paper_doi               10.1107/S160053681401650X
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          '[Ni (C15 H14 N1 O2)2]'
_chemical_formula_moiety         'C30 H28 N2 Ni O4'
_chemical_formula_sum            'C30 H28 N2 Ni O4'
_chemical_formula_weight         539.23
_chemical_melting_point_gt       469
_chemical_melting_point_lt       472
_chemical_name_systematic
;
Bis{2-[(E)-(4-methoxylbenzyl)iminomethyl]phenolato-κ²N,O¹}nickel(II)
;
_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                 95.6820(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.1847(2)
_cell_length_b                   5.67380(10)
_cell_length_c                   17.7620(3)
_cell_measurement_reflns_used    3542
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      1.68
_cell_volume                     1221.92(4)
_computing_cell_refinement       'APEX2 (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009), Mercury
(Macrae et al., 2006) and publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14541
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.68
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  0.8759
_exptl_absorpt_correction_T_min  0.6702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.324
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         3542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0277
_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)+(0.0313P)²+0.7976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0744
_reflns_number_gt                3092
_reflns_number_total             3542
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5419sup1.cf
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239808
_cod_database_fobs_code          2239808
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_symmetry_multiplicity
Ni Ni1 0.5000 0.0000 0.5000 0.01253(7) Uani d S 1 2
O O1 0.58126(8) -0.03642(16) 0.41876(5) 0.01676(19) Uani d . 1 1
O O2 -0.03916(8) -0.2287(2) 0.34237(6) 0.0272(2) Uani d . 1 1
N N1 0.42000(8) 0.2622(2) 0.45360(6) 0.0142(2) Uani d . 1 1
C C1 0.60209(10) 0.1191(2) 0.36758(6) 0.0141(2) Uani d . 1 1
C C2 0.68624(10) 0.0696(3) 0.31981(7) 0.0164(2) Uani d . 1 1
H H2A 0.7260 -0.0744 0.3255 0.020 Uiso calc R 1 1
C C3 0.71053(10) 0.2297(3) 0.26525(7) 0.0176(2) Uani d . 1 1
H H3A 0.7676 0.1945 0.2343 0.021 Uiso calc R 1 1
C C4 0.65287(11) 0.4428(3) 0.25451(7) 0.0182(3) Uani d . 1 1
H H4A 0.6698 0.5501 0.2163 0.022 Uiso calc R 1 1
C C5 0.57101(10) 0.4940(2) 0.30048(7) 0.0157(2) Uani d . 1 1
H H5A 0.5315 0.6380 0.2938 0.019 Uiso calc R 1 1
C C6 0.54531(10) 0.3354(2) 0.35715(6) 0.0138(2) Uani d . 1 1
C C7 0.45329(10) 0.3875(2) 0.39913(7) 0.0146(2) Uani d . 1 1
H H7A 0.4130 0.5271 0.3857 0.018 Uiso calc R 1 1
C C8 0.31199(10) 0.3363(2) 0.47834(7) 0.0163(2) Uani d . 1 1
H H8A 0.2966 0.5015 0.4629 0.020 Uiso calc R 1 1
H H8B 0.3151 0.3279 0.5342 0.020 Uiso calc R 1 1
C C9 0.22048(10) 0.1787(2) 0.44360(7) 0.0159(2) Uani d . 1 1
C C10 0.16960(11) 0.2254(3) 0.37107(7) 0.0209(3) Uani d . 1 1
H H10A 0.1939 0.3559 0.3436 0.025 Uiso calc R 1 1
C C11 0.08462(11) 0.0860(3) 0.33834(7) 0.0235(3) Uani d . 1 1
H H11A 0.0517 0.1204 0.2888 0.028 Uiso calc R 1 1
C C12 0.04753(10) -0.1046(3) 0.37812(7) 0.0194(3) Uani d . 1 1
C C13 0.09757(11) -0.1573(3) 0.44988(8) 0.0216(3) Uani d . 1 1
H H13A 0.0735 -0.2887 0.4770 0.026 Uiso calc R 1 1
C C14 0.18353(11) -0.0150(3) 0.48172(8) 0.0203(3) Uani d . 1 1
H H14A 0.2176 -0.0518 0.5307 0.024 Uiso calc R 1 1
C C15 -0.08444(12) -0.4144(3) 0.38380(9) 0.0274(3) Uani d . 1 1
H H15A -0.1488 -0.4812 0.3537 0.041 Uiso calc R 1 1
H H15B -0.1069 -0.3521 0.4314 0.041 Uiso calc R 1 1
H H15C -0.0287 -0.5376 0.3947 0.041 Uiso calc R 1 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'
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
O1 Ni1 O1 . 3_656 180.0000(10)
O1 Ni1 N1 . . 92.30(4)
O1 Ni1 N1 3_656 . 87.70(4)
O1 Ni1 N1 . 3_656 87.70(4)
O1 Ni1 N1 3_656 3_656 92.30(4)
N1 Ni1 N1 . 3_656 180.00(6)
C1 O1 Ni1 . . 128.67(8)
C12 O2 C15 . . 117.36(11)
C7 N1 C8 . . 114.59(11)
C7 N1 Ni1 . . 124.19(9)
C8 N1 Ni1 . . 121.22(8)
O1 C1 C6 . . 123.41(11)
O1 C1 C2 . . 118.82(12)
C6 C1 C2 . . 117.77(11)
C3 C2 C1 . . 120.40(12)
C3 C2 H2A . . 119.8
C1 C2 H2A . . 119.8
C2 C3 C4 . . 121.55(12)
C2 C3 H3A . . 119.2
C4 C3 H3A . . 119.2
C5 C4 C3 . . 118.84(12)
C5 C4 H4A . . 120.6
C3 C4 H4A . . 120.6
C4 C5 C6 . . 120.87(12)
C4 C5 H5A . . 119.6
C6 C5 H5A . . 119.6
C5 C6 C1 . . 120.55(11)
C5 C6 C7 . . 118.67(12)
C1 C6 C7 . . 120.51(11)
N1 C7 C6 . . 126.28(12)
N1 C7 H7A . . 116.9
C6 C7 H7A . . 116.9
N1 C8 C9 . . 110.50(10)
N1 C8 H8A . . 109.5
C9 C8 H8A . . 109.5
N1 C8 H8B . . 109.5
C9 C8 H8B . . 109.5
H8A C8 H8B . . 108.1
C14 C9 C10 . . 117.60(12)
C14 C9 C8 . . 122.03(11)
C10 C9 C8 . . 120.37(12)
C11 C10 C9 . . 121.56(13)
C11 C10 H10A . . 119.2
C9 C10 H10A . . 119.2
C10 C11 C12 . . 119.86(12)
C10 C11 H11A . . 120.1
C12 C11 H11A . . 120.1
O2 C12 C13 . . 124.20(13)
O2 C12 C11 . . 115.95(12)
C13 C12 C11 . . 119.84(13)
C12 C13 C14 . . 119.37(13)
C12 C13 H13A . . 120.3
C14 C13 H13A . . 120.3
C9 C14 C13 . . 121.74(12)
C9 C14 H14A . . 119.1
C13 C14 H14A . . 119.1
O2 C15 H15A . . 109.5
O2 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
O2 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Ni1 O1 . 1.8407(9)
Ni1 O1 3_656 1.8407(9)
Ni1 N1 . 1.9191(11)
Ni1 N1 3_656 1.9191(11)
O1 C1 . 1.3095(15)
O2 C12 . 1.3717(16)
O2 C15 . 1.427(2)
N1 C7 . 1.2977(16)
N1 C8 . 1.4887(15)
C1 C6 . 1.4123(18)
C1 C2 . 1.4221(16)
C2 C3 . 1.3813(18)
C2 H2A . 0.9500
C3 C4 . 1.402(2)
C3 H3A . 0.9500
C4 C5 . 1.3810(17)
C4 H4A . 0.9500
C5 C6 . 1.4080(17)
C5 H5A . 0.9500
C6 C7 . 1.4374(16)
C7 H7A . 0.9500
C8 C9 . 1.5123(18)
C8 H8A . 0.9900
C8 H8B . 0.9900
C9 C14 . 1.3892(19)
C9 C10 . 1.3986(17)
C10 C11 . 1.384(2)
C10 H10A . 0.9500
C11 C12 . 1.392(2)
C11 H11A . 0.9500
C12 C13 . 1.3898(18)
C13 C14 . 1.3967(19)
C13 H13A . 0.9500
C14 H14A . 0.9500
C15 H15A . 0.9800
C15 H15B . 0.9800
C15 H15C . 0.9800
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
C11 H11A O2 2_555 0.95 2.47 3.3709(17) 158 y
C14 H14A O1 3_656 0.95 2.57 3.2281(17) 126 y
C5 H5A Cg1 2_655 0.95 2.68 3.3918(13) 132 y
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
N1 Ni1 O1 C1 . 22.59(11)
N1 Ni1 O1 C1 3_656 -157.41(11)
O1 Ni1 N1 C7 . -19.81(11)
O1 Ni1 N1 C8 . 159.85(9)
O1 Ni1 N1 C8 3_656 -20.15(9)
Ni1 O1 C1 C6 . -13.67(17)
Ni1 O1 C1 C2 . 166.19(9)
O1 C1 C2 C3 . -179.94(11)
C6 C1 C2 C3 . -0.06(18)
C1 C2 C3 C4 . -0.79(19)
C2 C3 C4 C5 . 0.89(19)
C3 C4 C5 C6 . -0.13(19)
C4 C5 C6 C1 . -0.71(18)
C4 C5 C6 C7 . -174.76(11)
O1 C1 C6 C5 . -179.33(11)
C2 C1 C6 C5 . 0.80(17)
O1 C1 C6 C7 . -5.40(18)
C2 C1 C6 C7 . 174.74(11)
C8 N1 C7 C6 . -170.38(11)
Ni1 N1 C7 C6 . 9.30(18)
C5 C6 C7 N1 . -178.90(12)
C1 C6 C7 N1 . 7.05(19)
C7 N1 C8 C9 . 99.88(13)
Ni1 N1 C8 C9 . -79.80(11)
N1 C8 C9 C14 . 95.30(14)
N1 C8 C9 C10 . -84.93(14)
C14 C9 C10 C11 . 0.7(2)
C8 C9 C10 C11 . -179.09(12)
C9 C10 C11 C12 . 0.5(2)
C15 O2 C12 C13 . 3.9(2)
C15 O2 C12 C11 . -175.51(13)
C10 C11 C12 O2 . 178.05(12)
C10 C11 C12 C13 . -1.4(2)
O2 C12 C13 C14 . -178.31(13)
C11 C12 C13 C14 . 1.1(2)
C10 C9 C14 C13 . -1.0(2)
C8 C9 C14 C13 . 178.78(12)
C12 C13 C14 C9 . 0.1(2)
