#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/27/2212706.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_2212706
loop_
_publ_author_name
'Shou-Xing Wang'
_publ_section_title
;
 Dichloro{2-[(2-isopropylaminoethylimino)methyl]-4-nitrophenolato}zinc(II)
;
_journal_coeditor_code           SU2002
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m706
_journal_page_last               m707
_journal_paper_doi               10.1107/S1600536807006010
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Zn Cl2 (C12 H17 N3 O3)]'
_chemical_formula_moiety         'C12 H17 Cl2 N3 O3 Zn'
_chemical_formula_sum            'C12 H17 Cl2 N3 O3 Zn'
_chemical_formula_weight         387.56
_chemical_name_systematic
;
Dichloro{4-nitro-2-[(2-isopropylaminoethylimino)methyl]phenolato}zinc(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                 109.1910(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7210(10)
_cell_length_b                   11.6750(10)
_cell_length_c                   12.356(2)
_cell_measurement_reflns_used    4303
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.4
_cell_volume                     1596.9(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13138
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.884
_exptl_absorpt_correction_T_max  0.6711
_exptl_absorpt_correction_T_min  0.5752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0328
_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)+(0.0416P)²+0.2873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0839
_reflns_number_gt                2929
_reflns_number_total             3631
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2002.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2212706
_cod_database_fobs_code          2212706
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
Zn Zn1 1.02182(2) 0.92077(2) 0.25907(2) 0.03657(10) Uani d . 1
Cl Cl1 0.84538(6) 0.90705(5) 0.29134(6) 0.04670(16) Uani d . 1
Cl Cl2 1.04556(6) 1.06472(5) 0.15077(5) 0.04535(16) Uani d . 1
O O1 1.15549(15) 0.92308(12) 0.40435(13) 0.0404(4) Uani d . 1
O O2 1.4097(2) 0.45170(18) 0.55851(19) 0.0771(7) Uani d . 1
O O3 1.5038(2) 0.5559(2) 0.7026(2) 0.0854(7) Uani d . 1
N N1 1.06479(15) 0.77315(14) 0.20042(14) 0.0314(4) Uani d . 1
N N2 0.81169(16) 0.67098(15) 0.09987(16) 0.0371(4) Uani d . 1
H H2A 0.8511 0.6739 0.1758 0.044 Uiso calc R 1
H H2B 0.8211 0.5998 0.0761 0.044 Uiso calc R 1
N N3 1.4287(2) 0.5435(2) 0.6085(2) 0.0561(6) Uani d . 1
C C1 1.21822(19) 0.72986(17) 0.38531(18) 0.0326(5) Uani d . 1
C C2 1.21922(19) 0.83231(17) 0.44774(18) 0.0334(5) Uani d . 1
C C3 1.2937(2) 0.83498(19) 0.56417(19) 0.0388(5) Uani d . 1
H H3 1.2971 0.9017 0.6063 0.047 Uiso calc R 1
C C4 1.3604(2) 0.7426(2) 0.6164(2) 0.0445(6) Uani d . 1
H H4 1.4077 0.7462 0.6932 0.053 Uiso calc R 1
C C5 1.3572(2) 0.6429(2) 0.5536(2) 0.0423(5) Uani d . 1
C C6 1.2885(2) 0.6363(2) 0.4406(2) 0.0394(5) Uani d . 1
H H6 1.2882 0.5692 0.4000 0.047 Uiso calc R 1
C C7 1.14665(19) 0.70878(18) 0.26600(18) 0.0329(5) Uani d . 1
H H7 1.1623 0.6409 0.2341 0.039 Uiso calc R 1
C C8 1.0059(2) 0.73661(19) 0.08119(17) 0.0357(5) Uani d . 1
H H8A 1.0237 0.6564 0.0739 0.043 Uiso calc R 1
H H8B 1.0387 0.7803 0.0315 0.043 Uiso calc R 1
C C9 0.8705(2) 0.75286(18) 0.04259(18) 0.0363(5) Uani d . 1
H H9A 0.8525 0.8306 0.0597 0.044 Uiso calc R 1
H H9B 0.8375 0.7422 -0.0397 0.044 Uiso calc R 1
C C10 0.6784(2) 0.6902(2) 0.0798(2) 0.0467(6) Uani d . 1
H H10 0.6661 0.7697 0.0987 0.056 Uiso calc R 1
C C11 0.6421(3) 0.6115(3) 0.1599(3) 0.0766(10) Uani d . 1
H H11A 0.6577 0.5335 0.1443 0.115 Uiso calc R 1
H H11B 0.5576 0.6209 0.1485 0.115 Uiso calc R 1
H H11C 0.6881 0.6301 0.2377 0.115 Uiso calc R 1
C C12 0.6064(3) 0.6685(3) -0.0440(3) 0.0670(8) Uani d . 1
H H12A 0.6350 0.7176 -0.0919 0.100 Uiso calc R 1
H H12B 0.5226 0.6842 -0.0565 0.100 Uiso calc R 1
H H12C 0.6156 0.5899 -0.0626 0.100 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
O1 Zn1 N1 97.09(7) n
O1 Zn1 Cl2 108.72(6) n
N1 Zn1 Cl2 109.73(6) n
O1 Zn1 Cl1 110.24(6) n
N1 Zn1 Cl1 111.17(5) n
Cl2 Zn1 Cl1 117.88(3) n
C2 O1 Zn1 122.88(13) ?
C7 N1 C8 118.21(18) ?
C7 N1 Zn1 120.27(14) ?
C8 N1 Zn1 121.51(13) ?
C9 N2 C10 116.16(18) ?
C9 N2 H2A 108.2 ?
C10 N2 H2A 108.2 ?
C9 N2 H2B 108.2 ?
C10 N2 H2B 108.2 ?
H2A N2 H2B 107.4 ?
O3 N3 O2 123.0(2) ?
O3 N3 C5 118.3(2) ?
O2 N3 C5 118.7(2) ?
C6 C1 C2 119.5(2) ?
C6 C1 C7 114.31(19) ?
C2 C1 C7 126.19(19) ?
O1 C2 C3 118.52(19) ?
O1 C2 C1 123.96(19) ?
C3 C2 C1 117.52(19) ?
C4 C3 C2 121.9(2) ?
C4 C3 H3 119.0 ?
C2 C3 H3 119.0 ?
C3 C4 C5 119.4(2) ?
C3 C4 H4 120.3 ?
C5 C4 H4 120.3 ?
C6 C5 C4 121.0(2) ?
C6 C5 N3 119.0(2) ?
C4 C5 N3 119.9(2) ?
C5 C6 C1 120.6(2) ?
C5 C6 H6 119.7 ?
C1 C6 H6 119.7 ?
N1 C7 C1 127.2(2) ?
N1 C7 H7 116.4 ?
C1 C7 H7 116.4 ?
N1 C8 C9 112.25(17) ?
N1 C8 H8A 109.2 ?
C9 C8 H8A 109.2 ?
N1 C8 H8B 109.2 ?
C9 C8 H8B 109.2 ?
H8A C8 H8B 107.9 ?
N2 C9 C8 111.83(17) ?
N2 C9 H9A 109.3 ?
C8 C9 H9A 109.3 ?
N2 C9 H9B 109.3 ?
C8 C9 H9B 109.3 ?
H9A C9 H9B 107.9 ?
C12 C10 C11 112.3(3) ?
C12 C10 N2 110.2(2) ?
C11 C10 N2 107.4(2) ?
C12 C10 H10 109.0 ?
C11 C10 H10 109.0 ?
N2 C10 H10 109.0 ?
C10 C11 H11A 109.5 ?
C10 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C10 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
C10 C12 H12A 109.5 ?
C10 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C10 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Zn1 O1 1.957(2) n
Zn1 N1 1.997(2) n
Zn1 Cl2 2.2220(10) n
Zn1 Cl1 2.2370(10) n
O1 C2 1.306(2) ?
O2 N3 1.220(3) ?
O3 N3 1.214(3) ?
N1 C7 1.277(3) ?
N1 C8 1.470(3) ?
N2 C9 1.487(3) ?
N2 C10 1.516(3) ?
N2 H2A 0.9000 ?
N2 H2B 0.9000 ?
N3 C5 1.462(3) ?
C1 C6 1.403(3) ?
C1 C2 1.421(3) ?
C1 C7 1.458(3) ?
C2 C3 1.417(3) ?
C3 C4 1.364(3) ?
C3 H3 0.9300 ?
C4 C5 1.392(4) ?
C4 H4 0.9300 ?
C5 C6 1.365(3) ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
C8 C9 1.511(3) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 C12 1.506(4) ?
C10 C11 1.510(4) ?
C10 H10 0.9800 ?
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 H2A Cl2 2_745 0.90 2.44 3.231(2) 146
N2 H2B O1 2_745 0.90 2.08 2.922(3) 154
C7 H7 Cl1 2_745 0.93 2.75 3.600(3) 153
C8 H8B Cl2 3_775 0.97 2.80 3.581(3) 138
C9 H9B Cl1 4_575 0.97 2.74 3.551(3) 141
