#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/94/2229499.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_2229499
loop_
_publ_author_name
'Huang, Hong-Wei'
_publ_section_title
;
 (4-Chloro-2-{[(pyridin-2-ylmethyl)imino]methyl}phenolato)iodido(methanol)zinc(II)
;
_journal_coeditor_code           RZ2553
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m313
_journal_paper_doi               10.1107/S160053681100417X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Zn (C13 H10 Cl N2 O) I (C H4 O)]'
_chemical_formula_moiety         'C14 H14 Cl I N2 O2 Zn'
_chemical_formula_sum            'C14 H14 Cl I N2 O2 Zn'
_chemical_formula_weight         469.99
_chemical_name_systematic
;
(4-Chloro-2-{[(pyridin-2-
ylmethyl)imino]methyl}phenolato)iodido(methanol)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                 98.9940(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0769(9)
_cell_length_b                   12.7212(16)
_cell_length_c                   18.225(2)
_cell_measurement_reflns_used    3746
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      2.7
_cell_volume                     1620.6(3)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9273
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    3.589
_exptl_absorpt_correction_T_max  0.5643
_exptl_absorpt_correction_T_min  0.5338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.914
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3522
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0247
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0266P)²+0.3654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0540
_refine_ls_wR_factor_ref         0.0577
_reflns_number_gt                2947
_reflns_number_total             3522
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2553.cif
_cod_data_source_block           I
_cod_original_cell_volume        1620.5(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229499
_cod_database_fobs_code          2229499
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
Zn Zn1 0.56550(5) 1.00055(2) 0.370141(16) 0.03411(9) Uani d . 1 . .
Cl Cl1 0.80941(15) 0.43991(6) 0.42899(5) 0.0673(3) Uani d . 1 . .
I I1 0.20664(3) 1.054046(16) 0.337917(10) 0.04454(7) Uani d . 1 . .
O O1 0.5675(3) 0.87992(14) 0.44157(10) 0.0428(5) Uani d . 1 . .
O O2 0.6619(3) 1.10027(17) 0.45789(11) 0.0461(5) Uani d D 1 . .
N N1 0.6673(3) 0.89862(17) 0.29675(11) 0.0343(5) Uani d . 1 . .
N N2 0.6831(3) 1.10583(17) 0.29614(12) 0.0353(5) Uani d . 1 . .
C C1 0.6966(4) 0.7424(2) 0.37342(14) 0.0331(6) Uani d . 1 . .
C C2 0.6271(4) 0.7827(2) 0.43675(14) 0.0350(6) Uani d . 1 . .
C C3 0.6226(5) 0.7138(2) 0.49658(16) 0.0502(8) Uani d . 1 . .
H H3 0.5819 0.7388 0.5394 0.060 Uiso calc R 1 . .
C C4 0.6768(5) 0.6104(2) 0.49358(17) 0.0517(8) Uani d . 1 . .
H H4 0.6702 0.5664 0.5338 0.062 Uiso calc R 1 . .
C C5 0.7407(5) 0.5715(2) 0.43160(17) 0.0443(7) Uani d . 1 . .
C C6 0.7511(4) 0.6356(2) 0.37262(16) 0.0394(6) Uani d . 1 . .
H H6 0.7951 0.6086 0.3310 0.047 Uiso calc R 1 . .
C C7 0.7123(4) 0.8024(2) 0.30781(15) 0.0357(6) Uani d . 1 . .
H H7 0.7599 0.7676 0.2697 0.043 Uiso calc R 1 . .
C C8 0.6893(5) 0.9462(2) 0.22567(15) 0.0450(7) Uani d . 1 . .
H H8A 0.5762 0.9319 0.1896 0.054 Uiso calc R 1 . .
H H8B 0.7983 0.9150 0.2076 0.054 Uiso calc R 1 . .
C C9 0.7177(4) 1.0624(2) 0.23317(15) 0.0364(6) Uani d . 1 . .
C C10 0.7742(4) 1.1230(3) 0.17688(15) 0.0451(7) Uani d . 1 . .
H H10 0.7966 1.0917 0.1329 0.054 Uiso calc R 1 . .
C C11 0.7966(4) 1.2294(3) 0.18702(17) 0.0492(8) Uani d . 1 . .
H H11 0.8336 1.2712 0.1499 0.059 Uiso calc R 1 . .
C C12 0.7637(4) 1.2735(2) 0.25260(17) 0.0480(7) Uani d . 1 . .
H H12 0.7803 1.3452 0.2610 0.058 Uiso calc R 1 . .
C C13 0.7061(4) 1.2099(2) 0.30520(17) 0.0437(7) Uani d . 1 . .
H H13 0.6817 1.2400 0.3493 0.052 Uiso calc R 1 . .
C C14 0.8502(5) 1.1310(3) 0.48795(17) 0.0548(8) Uani d . 1 . .
H H14A 0.8972 1.0869 0.5296 0.082 Uiso calc R 1 . .
H H14B 0.8498 1.2029 0.5040 0.082 Uiso calc R 1 . .
H H14C 0.9315 1.1240 0.4507 0.082 Uiso calc R 1 . .
H H2 0.585(4) 1.104(2) 0.4897(14) 0.055(9) 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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
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
O1 Zn1 N1 . . 88.42(8) ?
O1 Zn1 O2 . . 89.96(8) ?
N1 Zn1 O2 . . 140.91(9) ?
O1 Zn1 N2 . . 156.05(8) ?
N1 Zn1 N2 . . 77.17(8) ?
O2 Zn1 N2 . . 89.42(8) ?
O1 Zn1 I1 . . 104.65(6) ?
N1 Zn1 I1 . . 116.29(6) ?
O2 Zn1 I1 . . 101.87(6) ?
N2 Zn1 I1 . . 98.90(6) ?
C2 O1 Zn1 . . 130.13(16) ?
C14 O2 Zn1 . . 130.14(18) ?
C14 O2 H2 . . 112(2) ?
Zn1 O2 H2 . . 113(2) ?
C7 N1 C8 . . 118.7(2) ?
C7 N1 Zn1 . . 127.11(18) ?
C8 N1 Zn1 . . 114.18(16) ?
C9 N2 C13 . . 118.8(2) ?
C9 N2 Zn1 . . 115.00(17) ?
C13 N2 Zn1 . . 125.93(18) ?
C6 C1 C2 . . 119.1(2) ?
C6 C1 C7 . . 116.5(2) ?
C2 C1 C7 . . 124.4(2) ?
O1 C2 C3 . . 119.3(2) ?
O1 C2 C1 . . 123.4(2) ?
C3 C2 C1 . . 117.3(2) ?
C4 C3 C2 . . 121.8(3) ?
C4 C3 H3 . . 119.1 ?
C2 C3 H3 . . 119.1 ?
C5 C4 C3 . . 120.5(3) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
C6 C5 C4 . . 120.0(3) ?
C6 C5 Cl1 . . 120.2(2) ?
C4 C5 Cl1 . . 119.8(2) ?
C5 C6 C1 . . 121.3(3) ?
C5 C6 H6 . . 119.4 ?
C1 C6 H6 . . 119.4 ?
N1 C7 C1 . . 126.4(2) ?
N1 C7 H7 . . 116.8 ?
C1 C7 H7 . . 116.8 ?
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 ?
N2 C9 C10 . . 121.3(3) ?
N2 C9 C8 . . 116.7(2) ?
C10 C9 C8 . . 122.0(2) ?
C11 C10 C9 . . 119.2(3) ?
C11 C10 H10 . . 120.4 ?
C9 C10 H10 . . 120.4 ?
C12 C11 C10 . . 119.2(3) ?
C12 C11 H11 . . 120.4 ?
C10 C11 H11 . . 120.4 ?
C13 C12 C11 . . 118.7(3) ?
C13 C12 H12 . . 120.7 ?
C11 C12 H12 . . 120.7 ?
N2 C13 C12 . . 122.9(3) ?
N2 C13 H13 . . 118.6 ?
C12 C13 H13 . . 118.6 ?
O2 C14 H14A . . 109.5 ?
O2 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O2 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 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
Zn1 O1 . 2.0111(18) ?
Zn1 N1 . 2.071(2) ?
Zn1 O2 . 2.071(2) ?
Zn1 N2 . 2.158(2) ?
Zn1 I1 . 2.6060(5) ?
Cl1 C5 . 1.746(3) ?
O1 C2 . 1.314(3) ?
O2 C14 . 1.415(4) ?
O2 H2 . 0.86(3) ?
N1 C7 . 1.272(3) ?
N1 C8 . 1.460(3) ?
N2 C9 . 1.330(3) ?
N2 C13 . 1.340(3) ?
C1 C6 . 1.412(4) ?
C1 C2 . 1.419(3) ?
C1 C7 . 1.438(4) ?
C2 C3 . 1.403(4) ?
C3 C4 . 1.373(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.373(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.361(4) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.496(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.391(4) ?
C10 C11 . 1.372(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.372(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.365(4) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 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
O2 H2 O1 3_676 0.86(3) 1.79(3) 2.643(3) 176(3)
