#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/95/2239514.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_2239514
loop_
_publ_author_name
'de Oliveira, Adriano Bof'
'Feitosa, Bárbara Regina Santos'
'Näther, Christian'
'Jess, Inke'
_publ_section_title
;
 Bis(4-hydroxy-3-methoxybenzaldehyde
 4-phenylthiosemicarbazonato-N¹,S)nickel(II)
;
_journal_coeditor_code           LR2126
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m195
_journal_paper_doi               10.1107/S1600536814009027
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          '[Ni (C15 H14 N3 O2 S)2]'
_chemical_formula_moiety         'C30 H28 N6 Ni O4 S2'
_chemical_formula_sum            'C30 H28 N6 Ni O4 S2'
_chemical_formula_weight         659.41
_chemical_name_common
;Bis(4-hydroxy-3-methoxybenzaldehyde
4-phenylthiosemicarbazonato-N¹,S)nickel(II)
;
_chemical_name_systematic
;
Bis(4-hydroxy-3-methoxybenzaldehyde
4-phenylthiosemicarbazonato-N¹,S)nickel(II)
;
_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                98.514(4)
_cell_angle_beta                 92.062(5)
_cell_angle_gamma                102.698(5)
_cell_formula_units_Z            1
_cell_length_a                   6.8080(4)
_cell_length_b                   7.5569(4)
_cell_length_c                   14.3902(8)
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      1.43
_cell_volume                     712.47(7)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2008)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2008)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe IPDS-1'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3117
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_T_max  0.9362
_exptl_absorpt_correction_T_min  0.8002
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(X-SHAPE and X-RED32; Stoe & Cie, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             342
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0302
_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)+(0.0482P)²+0.0121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0796
_reflns_number_gt                2539
_reflns_number_total             2539
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            lr2126sup1.cf
_cod_data_source_block           I
_cod_database_code               2239514
_cod_database_fobs_code          2239514
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_symmetry_multiplicity
Ni Ni1 0.5000 1.0000 0.0000 0.02742(11) Uani d S 1 2
C C1 0.1523(3) 0.8520(2) 0.32101(13) 0.0331(4) Uani d . 1 1
C C2 0.3262(3) 0.8457(3) 0.37156(15) 0.0435(5) Uani d . 1 1
H H2 0.4537 0.8789 0.3463 0.052 Uiso calc R 1 1
C C3 0.3138(4) 0.7905(3) 0.45971(16) 0.0516(6) Uani d . 1 1
H H3 0.4338 0.7874 0.4946 0.062 Uiso calc R 1 1
C C4 0.1309(5) 0.7404(4) 0.49672(18) 0.0651(7) Uani d . 1 1
H H4 0.1233 0.7025 0.5568 0.078 Uiso calc R 1 1
C C5 -0.0420(5) 0.7461(5) 0.4453(2) 0.0808(10) Uani d . 1 1
H H5 -0.1697 0.7112 0.4701 0.097 Uiso calc R 1 1
C C6 -0.0314(4) 0.8019(4) 0.35813(18) 0.0580(6) Uani d . 1 1
H H6 -0.1516 0.8058 0.3236 0.070 Uiso calc R 1 1
N N1 0.1511(3) 0.9162(2) 0.23399(12) 0.0329(3) Uani d . 1 1
H H1N1 0.056(4) 0.957(3) 0.2191(18) 0.051(7) Uiso d . 1 1
C C7 0.2813(3) 0.9123(2) 0.16455(13) 0.0281(4) Uani d . 1 1
S S1 0.21900(7) 1.00329(7) 0.06685(3) 0.03549(13) Uani d . 1 1
N N2 0.4377(2) 0.8401(2) 0.17166(11) 0.0312(3) Uani d . 1 1
N N3 0.5427(2) 0.8441(2) 0.08926(11) 0.0300(3) Uani d . 1 1
C C8 0.6613(3) 0.7309(3) 0.07729(14) 0.0337(4) Uani d . 1 1
H H8 0.739(3) 0.737(3) 0.0244(16) 0.035(5) Uiso d . 1 1
C C9 0.6955(3) 0.5875(2) 0.12971(13) 0.0317(4) Uani d . 1 1
C C10 0.8662(3) 0.5206(3) 0.10650(14) 0.0364(4) Uani d . 1 1
H H10 0.9538 0.5760 0.0637 0.044 Uiso calc R 1 1
C C11 0.9096(3) 0.3751(3) 0.14491(14) 0.0362(4) Uani d . 1 1
H H11 1.0260 0.3307 0.1286 0.043 Uiso calc R 1 1
C C12 0.7829(3) 0.2951(2) 0.20690(14) 0.0322(4) Uani d . 1 1
C C13 0.6150(3) 0.3636(2) 0.23340(13) 0.0302(4) Uani d . 1 1
C C14 0.5702(3) 0.5083(2) 0.19495(13) 0.0315(4) Uani d . 1 1
H H14 0.4552 0.5539 0.2126 0.038 Uiso calc R 1 1
O O1 0.8234(2) 0.14835(19) 0.24410(11) 0.0411(3) Uani d . 1 1
H H1O1 0.7174 0.0896 0.2635 0.062 Uiso calc R 1 1
O O2 0.5064(2) 0.27403(18) 0.29749(10) 0.0392(3) Uani d . 1 1
C C15 0.3366(4) 0.3391(3) 0.33051(18) 0.0478(5) Uani d . 1 1
H H15A 0.3816 0.4655 0.3637 0.072 Uiso calc R 1 1
H H15B 0.2688 0.2604 0.3736 0.072 Uiso calc R 1 1
H H15C 0.2423 0.3362 0.2769 0.072 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'
S S 0.1246 0.1234 '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
N3 Ni1 N3 . 2_675 180.00(6)
N3 Ni1 S1 . 2_675 95.42(5)
N3 Ni1 S1 2_675 2_675 84.58(5)
N3 Ni1 S1 . . 84.58(5)
N3 Ni1 S1 2_675 . 95.42(5)
S1 Ni1 S1 2_675 . 180.00(3)
C6 C1 C2 . . 119.5(2)
C6 C1 N1 . . 116.8(2)
C2 C1 N1 . . 123.65(18)
C1 C2 C3 . . 119.7(2)
C1 C2 H2 . . 120.1
C3 C2 H2 . . 120.1
C4 C3 C2 . . 120.9(2)
C4 C3 H3 . . 119.6
C2 C3 H3 . . 119.6
C3 C4 C5 . . 118.9(2)
C3 C4 H4 . . 120.5
C5 C4 H4 . . 120.5
C4 C5 C6 . . 120.7(3)
C4 C5 H5 . . 119.6
C6 C5 H5 . . 119.6
C1 C6 C5 . . 120.3(3)
C1 C6 H6 . . 119.8
C5 C6 H6 . . 119.8
C7 N1 C1 . . 130.38(17)
C7 N1 H1N1 . . 111.6(19)
C1 N1 H1N1 . . 117.9(19)
N2 C7 N1 . . 121.37(16)
N2 C7 S1 . . 123.56(14)
N1 C7 S1 . . 115.05(13)
C7 S1 Ni1 . . 96.21(6)
C7 N2 N3 . . 110.66(14)
C8 N3 N2 . . 115.09(15)
C8 N3 Ni1 . . 123.66(13)
N2 N3 Ni1 . . 121.20(11)
N3 C8 C9 . . 131.97(17)
N3 C8 H8 . . 116.2(13)
C9 C8 H8 . . 111.8(13)
C10 C9 C14 . . 119.10(16)
C10 C9 C8 . . 114.36(17)
C14 C9 C8 . . 126.46(16)
C11 C10 C9 . . 120.99(18)
C11 C10 H10 . . 119.5
C9 C10 H10 . . 119.5
C12 C11 C10 . . 119.49(17)
C12 C11 H11 . . 120.3
C10 C11 H11 . . 120.3
C11 C12 O1 . . 119.75(16)
C11 C12 C13 . . 120.43(16)
O1 C12 C13 . . 119.81(17)
O2 C13 C14 . . 125.69(16)
O2 C13 C12 . . 113.95(15)
C14 C13 C12 . . 120.35(17)
C13 C14 C9 . . 119.58(16)
C13 C14 H14 . . 120.2
C9 C14 H14 . . 120.2
C12 O1 H1O1 . . 109.5
C13 O2 C15 . . 117.54(14)
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 N3 . 1.9220(15)
Ni1 N3 2_675 1.9220(15)
Ni1 S1 2_675 2.1753(5)
Ni1 S1 . 2.1753(5)
C1 C6 . 1.376(3)
C1 C2 . 1.380(3)
C1 N1 . 1.409(2)
C2 C3 . 1.392(3)
C2 H2 . 0.9500
C3 C4 . 1.370(4)
C3 H3 . 0.9500
C4 C5 . 1.380(5)
C4 H4 . 0.9500
C5 C6 . 1.381(4)
C5 H5 . 0.9500
C6 H6 . 0.9500
N1 C7 . 1.361(2)
N1 H1N1 . 0.81(3)
C7 N2 . 1.306(2)
C7 S1 . 1.7322(18)
N2 N3 . 1.407(2)
N3 C8 . 1.298(2)
C8 C9 . 1.462(2)
C8 H8 . 0.94(2)
C9 C10 . 1.398(3)
C9 C14 . 1.402(3)
C10 C11 . 1.383(3)
C10 H10 . 0.9500
C11 C12 . 1.375(3)
C11 H11 . 0.9500
C12 O1 . 1.375(2)
C12 C13 . 1.398(3)
C13 O2 . 1.367(2)
C13 C14 . 1.381(2)
C14 H14 . 0.9500
O1 H1O1 . 0.8400
O2 C15 . 1.423(2)
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
N1 H1N1 O1 1_465 0.81(3) 2.37(3) 3.122(2) 154(2)
O1 H1O1 N2 1_545 0.84 2.54 3.131(2) 129
