#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/53/2225362.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_2225362
loop_
_publ_author_name
'Liu, Lin'
_publ_section_title
{5-Methoxy-2-[(2-morpholinoethyl)iminomethyl]phenolato}(thiocyanato-κN)nickel(II)
_journal_coeditor_code           RZ2416
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m289
_journal_paper_doi               10.1107/S160053681000468X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Ni (C14 H19 N2 O3) (N C S)]'
_chemical_formula_moiety         'C15 H19 N3 Ni O3 S'
_chemical_formula_sum            'C15 H19 N3 Ni O3 S'
_chemical_formula_weight         380.10
_chemical_name_systematic
{5-Methoxy-2-[(2-morpholinoethyl)iminomethyl]phenolato}(thiocyanato-κN)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                 114.756(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3983(18)
_cell_length_b                   11.8202(17)
_cell_length_c                   12.2913(18)
_cell_measurement_reflns_used    2524
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.6
_cell_measurement_theta_min      2.5
_cell_volume                     1635.8(4)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω scan'
_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  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9279
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    1.331
_exptl_absorpt_correction_T_max  0.7956
_exptl_absorpt_correction_T_min  0.7767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.376
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0361
_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)+(0.0433P)²+0.1781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0901
_reflns_number_gt                2729
_reflns_number_total             3554
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2416.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225362
_cod_database_fobs_code          2225362
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 0.08568(2) 0.38142(2) 0.14197(3) 0.03183(11) Uani d . 1 . .
O O1 0.19256(14) 0.46933(15) 0.26251(14) 0.0392(4) Uani d . 1 . .
O O2 0.53990(16) 0.69070(18) 0.46786(17) 0.0579(5) Uani d . 1 . .
O O3 -0.24289(16) 0.14271(16) -0.05535(17) 0.0499(5) Uani d . 1 . .
S S1 -0.23786(6) 0.53989(8) 0.18241(7) 0.0594(2) Uani d . 1 . .
N N1 0.19869(17) 0.32497(18) 0.09614(18) 0.0377(5) Uani d . 1 . .
N N2 -0.02732(16) 0.27875(16) 0.02024(16) 0.0334(4) Uani d . 1 . .
N N3 -0.03493(18) 0.44345(18) 0.17904(19) 0.0426(5) Uani d . 1 . .
C C1 0.3595(2) 0.4495(2) 0.2126(2) 0.0393(6) Uani d . 1 . .
C C2 0.3021(2) 0.4969(2) 0.2800(2) 0.0345(5) Uani d . 1 . .
C C3 0.3625(2) 0.5777(2) 0.3677(2) 0.0385(6) Uani d . 1 . .
H H3 0.3264 0.6089 0.4135 0.046 Uiso calc R 1 . .
C C4 0.4760(2) 0.6113(2) 0.3864(2) 0.0435(6) Uani d . 1 . .
C C5 0.5327(2) 0.5647(3) 0.3200(3) 0.0542(8) Uani d . 1 . .
H H5 0.6090 0.5878 0.3335 0.065 Uiso calc R 1 . .
C C6 0.4760(2) 0.4856(3) 0.2358(3) 0.0529(7) Uani d . 1 . .
H H6 0.5143 0.4543 0.1921 0.064 Uiso calc R 1 . .
C C7 0.3061(2) 0.3638(2) 0.1276(2) 0.0428(6) Uani d . 1 . .
H H7 0.3510 0.3321 0.0909 0.051 Uiso calc R 1 . .
C C8 0.1593(2) 0.2292(2) 0.0126(3) 0.0496(7) Uani d . 1 . .
H H8A 0.1724 0.1583 0.0560 0.060 Uiso calc R 1 . .
H H8B 0.2023 0.2274 -0.0376 0.060 Uiso calc R 1 . .
C C9 0.0292(2) 0.2477(2) -0.0620(2) 0.0472(7) Uani d . 1 . .
H H9A 0.0177 0.3079 -0.1194 0.057 Uiso calc R 1 . .
H H9B -0.0067 0.1792 -0.1057 0.057 Uiso calc R 1 . .
C C10 -0.0414(2) 0.1787(2) 0.0893(2) 0.0375(6) Uani d . 1 . .
H H10A -0.0668 0.2055 0.1495 0.045 Uiso calc R 1 . .
H H10B 0.0351 0.1422 0.1306 0.045 Uiso calc R 1 . .
C C11 -0.1300(2) 0.0925(2) 0.0110(2) 0.0457(6) Uani d . 1 . .
H H11A -0.1010 0.0594 -0.0439 0.055 Uiso calc R 1 . .
H H11B -0.1381 0.0323 0.0608 0.055 Uiso calc R 1 . .
C C12 -0.2340(2) 0.2320(2) -0.1291(2) 0.0500(7) Uani d . 1 . .
H H12A -0.3120 0.2644 -0.1744 0.060 Uiso calc R 1 . .
H H12B -0.2052 0.2021 -0.1855 0.060 Uiso calc R 1 . .
C C13 -0.1501(2) 0.3231(2) -0.0532(2) 0.0450(7) Uani d . 1 . .
H H13A -0.1456 0.3830 -0.1051 0.054 Uiso calc R 1 . .
H H13B -0.1817 0.3555 -0.0001 0.054 Uiso calc R 1 . .
C C14 -0.1188(2) 0.4842(2) 0.1815(2) 0.0378(6) Uani d . 1 . .
C C15 0.4866(3) 0.7462(3) 0.5363(3) 0.0716(10) Uani d . 1 . .
H H15A 0.4169 0.7862 0.4833 0.107 Uiso calc R 1 . .
H H15B 0.5421 0.7988 0.5907 0.107 Uiso calc R 1 . .
H H15C 0.4648 0.6911 0.5808 0.107 Uiso calc 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'
S S 0.1246 0.1234 '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
N1 Ni1 O1 . . 93.86(8) ?
N1 Ni1 N3 . . 176.31(9) ?
O1 Ni1 N3 . . 87.85(8) ?
N1 Ni1 N2 . . 86.27(8) ?
O1 Ni1 N2 . . 176.19(8) ?
N3 Ni1 N2 . . 92.24(8) ?
C2 O1 Ni1 . . 127.84(15) ?
C4 O2 C15 . . 118.7(2) ?
C11 O3 C12 . . 110.8(2) ?
C7 N1 C8 . . 118.6(2) ?
C7 N1 Ni1 . . 126.50(18) ?
C8 N1 Ni1 . . 114.88(15) ?
C9 N2 C13 . . 108.85(19) ?
C9 N2 C10 . . 112.65(19) ?
C13 N2 C10 . . 106.55(18) ?
C9 N2 Ni1 . . 106.12(14) ?
C13 N2 Ni1 . . 117.30(15) ?
C10 N2 Ni1 . . 105.51(13) ?
C14 N3 Ni1 . . 168.7(2) ?
C7 C1 C2 . . 121.6(2) ?
C7 C1 C6 . . 119.4(2) ?
C2 C1 C6 . . 119.0(2) ?
O1 C2 C3 . . 118.4(2) ?
O1 C2 C1 . . 122.8(2) ?
C3 C2 C1 . . 118.8(2) ?
C4 C3 C2 . . 120.2(2) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
O2 C4 C3 . . 123.9(3) ?
O2 C4 C5 . . 115.0(2) ?
C3 C4 C5 . . 121.0(3) ?
C6 C5 C4 . . 119.5(2) ?
C6 C5 H5 . . 120.2 ?
C4 C5 H5 . . 120.2 ?
C5 C6 C1 . . 121.4(3) ?
C5 C6 H6 . . 119.3 ?
C1 C6 H6 . . 119.3 ?
N1 C7 C1 . . 125.4(2) ?
N1 C7 H7 . . 117.3 ?
C1 C7 H7 . . 117.3 ?
N1 C8 C9 . . 105.9(2) ?
N1 C8 H8A . . 110.6 ?
C9 C8 H8A . . 110.6 ?
N1 C8 H8B . . 110.6 ?
C9 C8 H8B . . 110.6 ?
H8A C8 H8B . . 108.7 ?
N2 C9 C8 . . 108.1(2) ?
N2 C9 H9A . . 110.1 ?
C8 C9 H9A . . 110.1 ?
N2 C9 H9B . . 110.1 ?
C8 C9 H9B . . 110.1 ?
H9A C9 H9B . . 108.4 ?
N2 C10 C11 . . 113.25(19) ?
N2 C10 H10A . . 108.9 ?
C11 C10 H10A . . 108.9 ?
N2 C10 H10B . . 108.9 ?
C11 C10 H10B . . 108.9 ?
H10A C10 H10B . . 107.7 ?
O3 C11 C10 . . 111.2(2) ?
O3 C11 H11A . . 109.4 ?
C10 C11 H11A . . 109.4 ?
O3 C11 H11B . . 109.4 ?
C10 C11 H11B . . 109.4 ?
H11A C11 H11B . . 108.0 ?
O3 C12 C13 . . 110.5(2) ?
O3 C12 H12A . . 109.5 ?
C13 C12 H12A . . 109.5 ?
O3 C12 H12B . . 109.5 ?
C13 C12 H12B . . 109.5 ?
H12A C12 H12B . . 108.1 ?
N2 C13 C12 . . 112.5(2) ?
N2 C13 H13A . . 109.1 ?
C12 C13 H13A . . 109.1 ?
N2 C13 H13B . . 109.1 ?
C12 C13 H13B . . 109.1 ?
H13A C13 H13B . . 107.8 ?
N3 C14 S1 . . 178.8(2) ?
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
_geom_bond_publ_flag
Ni1 N1 . 1.840(2) ?
Ni1 O1 . 1.8402(16) ?
Ni1 N3 . 1.885(2) ?
Ni1 N2 . 1.9796(19) ?
O1 C2 . 1.323(3) ?
O2 C4 . 1.359(3) ?
O2 C15 . 1.429(4) ?
O3 C11 . 1.421(3) ?
O3 C12 . 1.425(3) ?
S1 C14 . 1.621(3) ?
N1 C7 . 1.304(3) ?
N1 C8 . 1.468(3) ?
N2 C9 . 1.497(3) ?
N2 C13 . 1.502(3) ?
N2 C10 . 1.508(3) ?
N3 C14 . 1.158(3) ?
C1 C7 . 1.406(3) ?
C1 C2 . 1.414(3) ?
C1 C6 . 1.415(3) ?
C2 C3 . 1.400(3) ?
C3 C4 . 1.385(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.394(4) ?
C5 C6 . 1.353(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.500(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.512(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.517(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
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
C3 H3 O3 2_555 0.93 2.40 3.313(4) 165
C7 H7 O2 2_645 0.93 2.44 3.329(4) 160
C10 H10B S1 2_545 0.97 2.87 3.797(2) 161
C13 H13A O1 3_565 0.97 2.49 3.432(3) 165
