#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/03/2210380.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_2210380
loop_
_publ_author_name
'Xiao-Yang Qiu'
_publ_section_title
;
 Dichloro{2-[2-(ethylamino)ethyliminomethyl]-4-nitrophenolato}zinc(II)
;
_journal_coeditor_code           SJ2099
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2175
_journal_page_last               m2176
_journal_paper_doi               10.1107/S1600536806031461
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Zn Cl2 (C11 H15 N3 O3)]'
_chemical_formula_moiety         'C11 H15 Cl2 N3 O3 Zn'
_chemical_formula_sum            'C11 H15 Cl2 N3 O3 Zn'
_chemical_formula_weight         373.53
_chemical_name_systematic
;
Dichloro{4-nitro-2-[2-(ethylamino)ethyliminomethyl]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                 115.077(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.879(2)
_cell_length_b                   11.478(2)
_cell_length_c                   12.612(2)
_cell_measurement_reflns_used    815
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      2.4
_cell_volume                     1557.5(5)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Buker SMART APEX 1000 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  0.0942
_diffrn_reflns_av_sigmaI/netI    0.1105
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13152
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.928
_exptl_absorpt_correction_T_max  0.8768
_exptl_absorpt_correction_T_min  0.8016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.399
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0594
_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)+(0.0366P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1377
_reflns_number_gt                2082
_reflns_number_total             3559
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2099.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210380
_cod_database_fobs_code          2210380
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 0.97634(6) 0.07347(4) 0.24705(5) 0.0364(2) Uani d . 1
Cl Cl1 1.16283(13) 0.09410(10) 0.24321(12) 0.0467(4) Uani d . 1
Cl Cl2 0.94872(14) -0.07529(11) 0.34443(11) 0.0512(4) Uani d . 1
O O1 0.8451(3) 0.0643(3) 0.0874(3) 0.0426(9) Uani d . 1
O O2 0.5556(6) 0.5247(4) -0.1176(4) 0.121(2) Uani d . 1
O O3 0.4968(6) 0.4197(4) -0.2716(4) 0.126(2) Uani d . 1
N N1 0.5545(5) 0.4332(5) -0.1666(5) 0.0796(18) Uani d . 1
N N2 0.9233(3) 0.2249(3) 0.2898(3) 0.0295(9) Uani d . 1
N N3 1.1877(3) 0.3173(3) 0.4230(3) 0.0349(10) Uani d . 1
H H3A 1.1594 0.3009 0.3462 0.042 Uiso calc R 1
H H3B 1.1749 0.3937 0.4297 0.042 Uiso calc R 1
C C1 0.7711(4) 0.2597(4) 0.0878(4) 0.0336(11) Uani d . 1
C C2 0.7755(4) 0.1525(4) 0.0322(4) 0.0313(11) Uani d . 1
C C3 0.6999(4) 0.1418(4) -0.0888(4) 0.0378(12) Uani d . 1
H H3 0.6988 0.0713 -0.1256 0.045 Uiso calc R 1
C C4 0.6278(5) 0.2319(5) -0.1541(4) 0.0473(14) Uani d . 1
H H4 0.5790 0.2236 -0.2339 0.057 Uiso calc R 1
C C5 0.6304(5) 0.3356(4) -0.0968(5) 0.0464(14) Uani d . 1
C C6 0.6962(5) 0.3491(4) 0.0192(5) 0.0437(13) Uani d . 1
H H6 0.6917 0.4192 0.0542 0.052 Uiso calc R 1
C C7 0.8396(4) 0.2861(4) 0.2117(4) 0.0323(11) Uani d . 1
H H7 0.8198 0.3561 0.2369 0.039 Uiso calc R 1
C C8 0.9780(4) 0.2691(4) 0.4107(4) 0.0354(12) Uani d . 1
H H8A 0.9374 0.2316 0.4541 0.042 Uiso calc R 1
H H8B 0.9620 0.3521 0.4095 0.042 Uiso calc R 1
C C9 1.1152(5) 0.2485(4) 0.4729(4) 0.0379(12) Uani d . 1
H H9A 1.1431 0.2687 0.5548 0.045 Uiso calc R 1
H H9B 1.1317 0.1663 0.4686 0.045 Uiso calc R 1
C C10 1.3233(5) 0.2936(5) 0.4809(5) 0.0585(16) Uani d . 1
H H10A 1.3379 0.2114 0.4740 0.070 Uiso calc R 1
H H10B 1.3548 0.3123 0.5634 0.070 Uiso calc R 1
C C11 1.3915(6) 0.3637(6) 0.4270(7) 0.093(2) Uani d . 1
H H11A 1.3642 0.3415 0.3465 0.140 Uiso calc R 1
H H11B 1.4791 0.3496 0.4685 0.140 Uiso calc R 1
H H11C 1.3749 0.4450 0.4314 0.140 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 N2 96.85(14) y
O1 Zn1 Cl2 106.81(10) y
N2 Zn1 Cl2 112.60(11) y
O1 Zn1 Cl1 110.23(11) y
N2 Zn1 Cl1 109.90(11) y
Cl2 Zn1 Cl1 118.26(5) y
C2 O1 Zn1 123.7(3) ?
O2 N1 O3 123.0(6) ?
O2 N1 C5 118.8(5) ?
O3 N1 C5 118.2(6) ?
C7 N2 C8 117.9(4) ?
C7 N2 Zn1 120.2(3) ?
C8 N2 Zn1 121.9(3) ?
C10 N3 C9 113.3(4) ?
C10 N3 H3A 108.9 ?
C9 N3 H3A 108.9 ?
C10 N3 H3B 108.9 ?
C9 N3 H3B 108.9 ?
H3A N3 H3B 107.7 ?
C6 C1 C2 118.5(4) ?
C6 C1 C7 115.6(4) ?
C2 C1 C7 125.9(4) ?
O1 C2 C3 118.6(4) ?
O1 C2 C1 123.5(4) ?
C3 C2 C1 117.8(4) ?
C4 C3 C2 122.2(5) ?
C4 C3 H3 118.9 ?
C2 C3 H3 118.9 ?
C3 C4 C5 117.7(5) ?
C3 C4 H4 121.2 ?
C5 C4 H4 121.2 ?
C6 C5 C4 122.7(5) ?
C6 C5 N1 119.2(5) ?
C4 C5 N1 118.0(5) ?
C5 C6 C1 121.0(5) ?
C5 C6 H6 119.5 ?
C1 C6 H6 119.5 ?
N2 C7 C1 127.8(4) ?
N2 C7 H7 116.1 ?
C1 C7 H7 116.1 ?
N2 C8 C9 113.1(4) ?
N2 C8 H8A 109.0 ?
C9 C8 H8A 109.0 ?
N2 C8 H8B 109.0 ?
C9 C8 H8B 109.0 ?
H8A C8 H8B 107.8 ?
N3 C9 C8 113.0(4) ?
N3 C9 H9A 109.0 ?
C8 C9 H9A 109.0 ?
N3 C9 H9B 109.0 ?
C8 C9 H9B 109.0 ?
H9A C9 H9B 107.8 ?
N3 C10 C11 111.2(5) ?
N3 C10 H10A 109.4 ?
C11 C10 H10A 109.4 ?
N3 C10 H10B 109.4 ?
C11 C10 H10B 109.4 ?
H10A C10 H10B 108.0 ?
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 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Zn1 O1 1.958(3) y
Zn1 N2 1.999(4) y
Zn1 Cl2 2.2074(14) y
Zn1 Cl1 2.2487(15) y
O1 C2 1.306(5) ?
O2 N1 1.215(6) ?
O3 N1 1.216(6) ?
N1 C5 1.473(7) ?
N2 C7 1.273(5) ?
N2 C8 1.472(5) ?
N3 C10 1.485(6) ?
N3 C9 1.490(5) ?
N3 H3A 0.9000 ?
N3 H3B 0.9000 ?
C1 C6 1.393(6) ?
C1 C2 1.428(6) ?
C1 C7 1.455(6) ?
C2 C3 1.410(6) ?
C3 C4 1.371(7) ?
C3 H3 0.9300 ?
C4 C5 1.386(7) ?
C4 H4 0.9300 ?
C5 C6 1.344(7) ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
C8 C9 1.498(6) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 C11 1.494(8) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
C11 H11C 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
N3 H3B O1 2_755 0.90 1.97 2.857(5) 167
N3 H3A Cl1 . 0.90 2.71 3.350(4) 129
N3 H3A Cl2 2_755 0.90 2.61 3.300(4) 134
C7 H7 Cl1 2_755 0.93 2.74 3.583(4) 151
C9 H9A Cl1 4_566 0.97 2.78 3.684(4) 156
C10 H10B O3 1_656 0.97 2.39 3.261(4) 149
