#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/13/2221334.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_2221334
loop_
_publ_author_name
'Hong, Zhe'
_publ_section_title
;
 Redetermination of
 {2-[3-(dimethylammonio)propyliminomethyl]phenolato}dithiocyanatozinc(II)
;
_journal_coeditor_code           ER2062
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m419
_journal_paper_doi               10.1107/S1600536809009568
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Zn (N C S)2 (C12 H18 N2 O)]'
_chemical_formula_moiety         'C14 H18 N4 O S2 Zn'
_chemical_formula_sum            'C14 H18 N4 O S2 Zn'
_chemical_formula_weight         387.81
_chemical_name_systematic
;
{2-[3-(dimethylammonio)propyliminomethyl]phenolato}dithiocyanatozinc(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 101.450(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.850(2)
_cell_length_b                   14.931(3)
_cell_length_c                   12.290(3)
_cell_measurement_reflns_used    3352
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.5
_cell_measurement_theta_min      2.3
_cell_volume                     1771.5(7)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       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  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10464
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.627
_exptl_absorpt_correction_T_max  0.7367
_exptl_absorpt_correction_T_min  0.7059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.490
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         4067
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0357
_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)+(0.039P)²+0.5P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0890
_reflns_number_gt                3048
_reflns_number_total             4067
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            er2062.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2221334
_cod_database_fobs_code          2221334
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Zn Zn1 0.85499(3) 0.192204(19) 0.33421(2) 0.04580(11) Uani d . 1 . .
S S1 1.05230(8) 0.47887(5) 0.33292(6) 0.0647(2) Uani d . 1 . .
S S2 0.62695(9) 0.21786(8) 0.63228(6) 0.0849(3) Uani d . 1 . .
O O1 0.98390(17) 0.09278(11) 0.33954(13) 0.0506(4) Uani d . 1 . .
N N1 0.72661(19) 0.15862(14) 0.19440(16) 0.0444(4) Uani d . 1 . .
N N2 0.7435(2) 0.38001(14) -0.03594(16) 0.0473(5) Uani d D 1 . .
N N3 0.9446(3) 0.30791(16) 0.3333(2) 0.0607(6) Uani d . 1 . .
N N4 0.7670(3) 0.19029(16) 0.4625(2) 0.0660(6) Uani d . 1 . .
C C1 0.8647(2) 0.02717(16) 0.16587(19) 0.0448(5) Uani d . 1 . .
C C2 0.9731(2) 0.03075(15) 0.26025(19) 0.0431(5) Uani d . 1 . .
C C3 1.0747(3) -0.03634(17) 0.2697(2) 0.0558(7) Uani d . 1 . .
H H3 1.1456 -0.0368 0.3321 0.067 Uiso calc R 1 . .
C C4 1.0736(3) -0.10103(18) 0.1908(3) 0.0637(7) Uani d . 1 . .
H H4 1.1444 -0.1432 0.1997 0.076 Uiso calc R 1 . .
C C5 0.9690(3) -0.1042(2) 0.0987(3) 0.0708(8) Uani d . 1 . .
H H5 0.9685 -0.1479 0.0446 0.085 Uiso calc R 1 . .
C C6 0.8654(3) -0.0416(2) 0.0880(2) 0.0650(8) Uani d . 1 . .
H H6 0.7927 -0.0449 0.0269 0.078 Uiso calc R 1 . .
C C7 0.7495(2) 0.08861(17) 0.14064(19) 0.0483(6) Uani d . 1 . .
H H7 0.6836 0.0757 0.0773 0.058 Uiso calc R 1 . .
C C8 0.6009(3) 0.21127(19) 0.1489(2) 0.0556(7) Uani d . 1 . .
H H8A 0.5460 0.2186 0.2057 0.067 Uiso calc R 1 . .
H H8B 0.5454 0.1791 0.0872 0.067 Uiso calc R 1 . .
C C9 0.6387(3) 0.30309(17) 0.1095(2) 0.0518(6) Uani d . 1 . .
H H9A 0.5547 0.3354 0.0777 0.062 Uiso calc R 1 . .
H H9B 0.6877 0.3372 0.1724 0.062 Uiso calc R 1 . .
C C10 0.7288(3) 0.29423(15) 0.0237(2) 0.0464(6) Uani d . 1 . .
H H10A 0.8200 0.2737 0.0600 0.056 Uiso calc R 1 . .
H H10B 0.6892 0.2491 -0.0302 0.056 Uiso calc R 1 . .
C C11 0.7994(3) 0.45391(19) 0.0407(2) 0.0682(8) Uani d . 1 . .
H H11A 0.8824 0.4343 0.0897 0.102 Uiso calc R 1 . .
H H11B 0.7319 0.4708 0.0836 0.102 Uiso calc R 1 . .
H H11C 0.8199 0.5045 -0.0014 0.102 Uiso calc R 1 . .
C C12 0.8300(3) 0.3647(2) -0.1207(2) 0.0707(8) Uani d . 1 . .
H H12A 0.8385 0.4196 -0.1594 0.106 Uiso calc R 1 . .
H H12B 0.7871 0.3201 -0.1726 0.106 Uiso calc R 1 . .
H H12C 0.9203 0.3445 -0.0847 0.106 Uiso calc R 1 . .
C C13 0.9883(2) 0.37954(18) 0.33335(18) 0.0448(5) Uani d . 1 . .
C C14 0.7095(3) 0.20301(17) 0.5332(2) 0.0497(6) Uani d . 1 . .
H H2 0.6584(14) 0.3946(16) -0.0715(18) 0.052(7) Uiso d 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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 Zn1 N4 . . 107.10(10) ?
N3 Zn1 O1 . . 112.62(9) ?
N4 Zn1 O1 . . 110.76(9) ?
N3 Zn1 N1 . . 115.61(9) ?
N4 Zn1 N1 . . 112.86(10) ?
O1 Zn1 N1 . . 97.80(8) ?
C2 O1 Zn1 . . 123.25(14) ?
C7 N1 C8 . . 117.3(2) ?
C7 N1 Zn1 . . 120.38(16) ?
C8 N1 Zn1 . . 122.30(18) ?
C11 N2 C12 . . 111.5(2) ?
C11 N2 C10 . . 112.6(2) ?
C12 N2 C10 . . 109.6(2) ?
C11 N2 H2 . . 108.9(16) ?
C12 N2 H2 . . 107.9(16) ?
C10 N2 H2 . . 106.1(16) ?
C13 N3 Zn1 . . 174.8(2) ?
C14 N4 Zn1 . . 169.0(2) ?
C6 C1 C2 . . 118.8(2) ?
C6 C1 C7 . . 115.3(2) ?
C2 C1 C7 . . 125.8(2) ?
O1 C2 C3 . . 118.9(2) ?
O1 C2 C1 . . 124.3(2) ?
C3 C2 C1 . . 116.8(2) ?
C4 C3 C2 . . 122.7(2) ?
C4 C3 H3 . . 118.6 ?
C2 C3 H3 . . 118.6 ?
C3 C4 C5 . . 120.6(3) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C6 C5 C4 . . 118.6(3) ?
C6 C5 H5 . . 120.7 ?
C4 C5 H5 . . 120.7 ?
C5 C6 C1 . . 122.5(3) ?
C5 C6 H6 . . 118.7 ?
C1 C6 H6 . . 118.7 ?
N1 C7 C1 . . 128.3(2) ?
N1 C7 H7 . . 115.9 ?
C1 C7 H7 . . 115.9 ?
N1 C8 C9 . . 111.1(2) ?
N1 C8 H8A . . 109.4 ?
C9 C8 H8A . . 109.4 ?
N1 C8 H8B . . 109.4 ?
C9 C8 H8B . . 109.4 ?
H8A C8 H8B . . 108.0 ?
C10 C9 C8 . . 110.9(2) ?
C10 C9 H9A . . 109.5 ?
C8 C9 H9A . . 109.5 ?
C10 C9 H9B . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 108.1 ?
N2 C10 C9 . . 113.16(19) ?
N2 C10 H10A . . 108.9 ?
C9 C10 H10A . . 108.9 ?
N2 C10 H10B . . 108.9 ?
C9 C10 H10B . . 108.9 ?
H10A C10 H10B . . 107.8 ?
N2 C11 H11A . . 109.5 ?
N2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
N2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N2 C12 H12A . . 109.5 ?
N2 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N2 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N3 C13 S1 . . 178.9(2) ?
N4 C14 S2 . . 178.3(3) ?
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
Zn1 O1 . 1.946(2) ?
Zn1 N1 . 1.985(2) ?
Zn1 N3 . 1.941(2) ?
Zn1 N4 . 1.945(2) ?
S1 C13 . 1.612(3) ?
S2 C14 . 1.608(3) ?
O1 C2 . 1.333(3) ?
N1 C7 . 1.280(3) ?
N1 C8 . 1.479(3) ?
N2 C11 . 1.484(3) ?
N2 C12 . 1.489(3) ?
N2 C10 . 1.497(3) ?
N2 H2 . 0.891(10) ?
N3 C13 . 1.153(3) ?
N4 C14 . 1.142(3) ?
C1 C6 . 1.405(3) ?
C1 C2 . 1.413(3) ?
C1 C7 . 1.444(3) ?
C2 C3 . 1.404(3) ?
C3 C4 . 1.367(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.372(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.371(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.524(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.513(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 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
N2 H2 O1 4_565 0.891(10) 1.855(11) 2.737(2) 170(2)
