#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/91/2219174.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_2219174
loop_
_publ_author_name
'Zhu, Xue-Wen'
'Yang, Xu-Zhao'
_publ_section_title
Dibromido{(E)-2-ethoxy-6-[3-(methylammonio)propyliminomethyl]phenolato}zinc(II)
_journal_coeditor_code           SJ2525
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1092
_journal_page_last               m1093
_journal_paper_doi               10.1107/S1600536808023672
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Zn Br2 (C13 H20 N2 O2)]'
_chemical_formula_moiety         'C13 H20 Br2 N2 O2 Zn'
_chemical_formula_sum            'C13 H20 Br2 N2 O2 Zn'
_chemical_formula_weight         461.50
_chemical_name_systematic
;
Dibromido{(E)-2-ethoxy-6-[3-
(methylammonio)propyliminomethyl]phenolato}zinc(II)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 114.482(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.884(3)
_cell_length_b                   14.374(2)
_cell_length_c                   14.992(2)
_cell_measurement_reflns_used    1842
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.1
_cell_measurement_theta_min      2.4
_cell_volume                     3507.4(9)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'ω scans'
_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  0.0683
_diffrn_reflns_av_sigmaI/netI    0.0812
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14138
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.959
_exptl_absorpt_correction_T_max  0.3675
_exptl_absorpt_correction_T_min  0.3410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.116
_refine_diff_density_min         -0.903
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0674
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1251P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1758
_refine_ls_wR_factor_ref         0.2215
_reflns_number_gt                1974
_reflns_number_total             3787
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2525.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2219174
_cod_database_fobs_code          2219174
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Zn Zn1 0.27393(5) 0.33839(6) 0.31911(7) 0.0412(3) Uani d . 1
Br Br1 0.41500(7) 0.37049(9) 0.38443(10) 0.0911(5) Uani d . 1
Br Br2 0.22492(8) 0.35250(9) 0.14417(9) 0.0842(4) Uani d . 1
O O1 0.2106(3) 0.4129(3) 0.3728(4) 0.0457(13) Uani d . 1
O O2 0.1034(3) 0.5348(4) 0.3750(4) 0.0524(15) Uani d . 1
N N1 0.2463(4) 0.2150(4) 0.3615(5) 0.0435(15) Uani d . 1
N N2 0.2234(4) 0.0849(4) 0.0895(5) 0.0506(17) Uani d . 1
H H2A 0.2508 0.1333 0.0793 0.061 Uiso calc R 1
H H2B 0.2536 0.0335 0.0945 0.061 Uiso calc R 1
C C1 0.1272(5) 0.2825(6) 0.3792(6) 0.049(2) Uani d . 1
C C2 0.1426(4) 0.3790(5) 0.3754(5) 0.0394(17) Uani d . 1
C C3 0.0835(5) 0.4402(6) 0.3797(5) 0.047(2) Uani d . 1
C C4 0.0121(5) 0.4091(8) 0.3825(6) 0.065(3) Uani d . 1
H H4 -0.0272 0.4517 0.3819 0.078 Uiso calc R 1
C C5 -0.0022(6) 0.3135(8) 0.3860(7) 0.074(3) Uani d . 1
H H5 -0.0509 0.2930 0.3879 0.089 Uiso calc R 1
C C6 0.0554(6) 0.2503(8) 0.3869(7) 0.068(3) Uani d . 1
H H6 0.0473 0.1870 0.3924 0.082 Uiso calc R 1
C C7 0.1826(6) 0.2104(5) 0.3813(6) 0.055(2) Uani d . 1
H H7 0.1713 0.1520 0.3995 0.066 Uiso calc R 1
C C8 0.2915(6) 0.1308(6) 0.3638(7) 0.057(2) Uani d . 1
H H8A 0.2641 0.0783 0.3781 0.069 Uiso calc R 1
H H8B 0.3462 0.1354 0.4162 0.069 Uiso calc R 1
C C9 0.2982(5) 0.1139(6) 0.2700(6) 0.055(2) Uani d . 1
H H9A 0.3320 0.0593 0.2767 0.067 Uiso calc R 1
H H9B 0.3253 0.1665 0.2557 0.067 Uiso calc R 1
C C10 0.2170(5) 0.0998(6) 0.1873(7) 0.057(2) Uani d . 1
H H10A 0.1828 0.1536 0.1818 0.068 Uiso calc R 1
H H10B 0.1906 0.0461 0.2009 0.068 Uiso calc R 1
C C11 0.1458(5) 0.0750(7) 0.0041(7) 0.065(3) Uani d . 1
H H11A 0.1211 0.0166 0.0073 0.097 Uiso calc R 1
H H11B 0.1554 0.0771 -0.0543 0.097 Uiso calc R 1
H H11C 0.1097 0.1249 0.0029 0.097 Uiso calc R 1
C C12 0.0459(6) 0.6012(7) 0.3834(7) 0.065(3) Uani d . 1
H H12A 0.0413 0.5924 0.4450 0.079 Uiso calc R 1
H H12B -0.0079 0.5922 0.3304 0.079 Uiso calc R 1
C C13 0.0754(6) 0.6948(8) 0.3788(8) 0.084(4) Uani d . 1
H H13A 0.1295 0.7025 0.4299 0.127 Uiso calc R 1
H H13B 0.0389 0.7395 0.3872 0.127 Uiso calc R 1
H H13C 0.0771 0.7041 0.3163 0.127 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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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 95.3(2) y
O1 Zn1 Br1 115.26(16) y
N1 Zn1 Br1 113.83(19) y
O1 Zn1 Br2 113.02(17) y
N1 Zn1 Br2 113.09(19) y
Br1 Zn1 Br2 106.38(6) y
C2 O1 Zn1 120.3(4) ?
C3 O2 C12 115.4(7) ?
C7 N1 C8 119.3(7) ?
C7 N1 Zn1 118.1(5) ?
C8 N1 Zn1 122.5(6) ?
C11 N2 C10 115.7(7) ?
C11 N2 H2A 108.4 ?
C10 N2 H2A 108.4 ?
C11 N2 H2B 108.4 ?
C10 N2 H2B 108.4 ?
H2A N2 H2B 107.4 ?
C6 C1 C2 121.3(8) ?
C6 C1 C7 114.0(8) ?
C2 C1 C7 124.6(7) ?
O1 C2 C3 119.4(7) ?
O1 C2 C1 123.7(7) ?
C3 C2 C1 116.8(7) ?
C4 C3 C2 121.9(9) ?
C4 C3 O2 124.8(8) ?
C2 C3 O2 113.1(7) ?
C3 C4 C5 120.5(9) ?
C3 C4 H4 119.8 ?
C5 C4 H4 119.8 ?
C6 C5 C4 120.1(9) ?
C6 C5 H5 119.9 ?
C4 C5 H5 119.9 ?
C5 C6 C1 119.2(9) ?
C5 C6 H6 120.4 ?
C1 C6 H6 120.4 ?
N1 C7 C1 129.0(8) ?
N1 C7 H7 115.5 ?
C1 C7 H7 115.5 ?
N1 C8 C9 112.2(7) ?
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 ?
C8 C9 C10 112.4(8) ?
C8 C9 H9A 109.1 ?
C10 C9 H9A 109.1 ?
C8 C9 H9B 109.1 ?
C10 C9 H9B 109.1 ?
H9A C9 H9B 107.9 ?
C9 C10 N2 112.7(7) ?
C9 C10 H10A 109.1 ?
N2 C10 H10A 109.1 ?
C9 C10 H10B 109.1 ?
N2 C10 H10B 109.1 ?
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 ?
O2 C12 C13 108.8(8) ?
O2 C12 H12A 109.9 ?
C13 C12 H12A 109.9 ?
O2 C12 H12B 109.9 ?
C13 C12 H12B 109.9 ?
H12A C12 H12B 108.3 ?
C12 C13 H13A 109.5 ?
C12 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C12 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Zn1 O1 1.958(5) y
Zn1 N1 2.014(6) y
Zn1 Br1 2.3429(16) y
Zn1 Br2 2.4046(18) y
O1 C2 1.325(8) ?
O2 C3 1.414(11) ?
O2 C12 1.446(9) ?
N1 C7 1.293(11) ?
N1 C8 1.447(10) ?
N2 C11 1.453(10) ?
N2 C10 1.532(11) ?
N2 H2A 0.9000 ?
N2 H2B 0.9000 ?
C1 C6 1.414(12) ?
C1 C2 1.420(11) ?
C1 C7 1.423(12) ?
C2 C3 1.396(11) ?
C3 C4 1.370(12) ?
C4 C5 1.403(15) ?
C4 H4 0.9300 ?
C5 C6 1.369(14) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
C8 C9 1.480(12) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 C10 1.481(11) ?
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 C13 1.456(15) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 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 H2B O1 4_545 0.90 1.84 2.697(8) 158
N2 H2B O2 4_545 0.90 2.40 3.005(8) 124
