#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/15/2221506.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_2221506
loop_
_publ_author_name
'Han, Cheng-Li'
_publ_section_title
{4-Bromo-2-[(2-morpholinoethyl)iminomethyl]phenolato}iodido(methanol)zinc(II)
_journal_coeditor_code           SJ2595
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m418
_journal_paper_doi               10.1107/S1600536809009234
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Zn (C13 H16 Br N2 O2) I (C H4 O)]'
_chemical_formula_moiety         'C14 H20 Br I N2 O3 Zn'
_chemical_formula_sum            'C14 H20 Br I N2 O3 Zn'
_chemical_formula_weight         536.50
_chemical_name_systematic
;
{4-Bromo-2-[(2-morpholinoethyl)iminomethyl]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                 100.497(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.747(2)
_cell_length_b                   24.977(3)
_cell_length_c                   9.598(2)
_cell_measurement_reflns_used    3128
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.8
_cell_measurement_theta_min      2.6
_cell_volume                     1826.1(6)
_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 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12877
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.63
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.235
_exptl_absorpt_correction_T_max  0.231
_exptl_absorpt_correction_T_min  0.217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.951
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.958
_refine_diff_density_min         -0.708
_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     203
_refine_ls_number_reflns         3928
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0385P)²+2.0556P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0955
_reflns_number_gt                2994
_reflns_number_total             3928
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2595.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221506
_cod_database_fobs_code          2221506
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 0.50584(7) 0.55343(2) 0.28004(5) 0.03432(14) Uani d . 1 . .
I I1 0.17781(4) 0.568293(16) 0.25354(4) 0.05466(14) Uani d . 1 . .
Br Br1 1.05025(10) 0.31501(2) 0.17245(8) 0.0752(2) Uani d . 1 . .
O O1 0.5139(4) 0.47117(12) 0.3133(3) 0.0403(8) Uani d . 1 . .
O O2 0.6023(12) 0.73465(19) 0.4160(5) 0.119(3) Uani d . 1 . .
O O3 0.6375(4) 0.56560(12) 0.4796(3) 0.0370(7) Uani d D 1 . .
N N1 0.6591(4) 0.54528(13) 0.1329(4) 0.0276(7) Uani d . 1 . .
N N2 0.5630(5) 0.65133(14) 0.2055(4) 0.0381(9) Uani d . 1 . .
C C1 0.7471(6) 0.45205(16) 0.1873(4) 0.0298(9) Uani d . 1 . .
C C2 0.6310(6) 0.43807(17) 0.2793(5) 0.0340(10) Uani d . 1 . .
C C3 0.6426(7) 0.38546(18) 0.3320(5) 0.0464(13) Uani d . 1 . .
H H3 0.5649 0.3747 0.3899 0.056 Uiso calc R 1 . .
C C4 0.7640(8) 0.34916(19) 0.3017(5) 0.0502(13) Uani d . 1 . .
H H4 0.7691 0.3148 0.3396 0.060 Uiso calc R 1 . .
C C5 0.8782(7) 0.36454(18) 0.2139(5) 0.0409(11) Uani d . 1 . .
C C6 0.8706(6) 0.41432(18) 0.1569(5) 0.0364(10) Uani d . 1 . .
H H6 0.9477 0.4237 0.0972 0.044 Uiso calc R 1 . .
C C7 0.7474(6) 0.50294(17) 0.1163(4) 0.0310(9) Uani d . 1 . .
H H7 0.8209 0.5054 0.0501 0.037 Uiso calc R 1 . .
C C8 0.6873(6) 0.59135(17) 0.0431(5) 0.0366(10) Uani d . 1 . .
H H8A 0.6722 0.5799 -0.0549 0.044 Uiso calc R 1 . .
H H8B 0.8066 0.6044 0.0713 0.044 Uiso calc R 1 . .
C C9 0.5603(6) 0.63595(17) 0.0561(4) 0.0346(10) Uani d . 1 . .
H H9A 0.5897 0.6669 0.0041 0.042 Uiso calc R 1 . .
H H9B 0.4426 0.6247 0.0137 0.042 Uiso calc R 1 . .
C C10 0.4279(9) 0.6926(2) 0.2083(6) 0.0645(18) Uani d . 1 . .
H H10A 0.3126 0.6775 0.1741 0.077 Uiso calc R 1 . .
H H10B 0.4458 0.7219 0.1464 0.077 Uiso calc R 1 . .
C C11 0.4376(14) 0.7133(3) 0.3593(8) 0.099(3) Uani d . 1 . .
H H11A 0.3489 0.7407 0.3593 0.118 Uiso calc R 1 . .
H H11B 0.4118 0.6842 0.4192 0.118 Uiso calc R 1 . .
C C12 0.7298(13) 0.6951(3) 0.4179(7) 0.100(3) Uani d . 1 . .
H H12A 0.7050 0.6656 0.4769 0.119 Uiso calc R 1 . .
H H12B 0.8438 0.7097 0.4592 0.119 Uiso calc R 1 . .
C C13 0.7348(9) 0.6746(2) 0.2692(6) 0.0619(16) Uani d . 1 . .
H H13A 0.7629 0.7038 0.2106 0.074 Uiso calc R 1 . .
H H13B 0.8256 0.6476 0.2735 0.074 Uiso calc R 1 . .
C C14 0.8215(7) 0.5553(2) 0.5089(6) 0.0561(14) Uani d . 1 . .
H H14A 0.8423 0.5183 0.4908 0.084 Uiso calc R 1 . .
H H14B 0.8673 0.5633 0.6064 0.084 Uiso calc R 1 . .
H H14C 0.8788 0.5773 0.4492 0.084 Uiso calc R 1 . .
H H3A 0.592(8) 0.554(2) 0.547(4) 0.080 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'
Br Br -0.2901 2.4595 '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'
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
N1 Zn1 O3 . . 114.78(13) y
N1 Zn1 O1 . . 90.15(12) y
O3 Zn1 O1 . . 90.42(13) y
N1 Zn1 I1 . . 130.76(10) y
O3 Zn1 I1 . . 113.36(9) y
O1 Zn1 I1 . . 99.31(9) y
C2 O1 Zn1 . . 126.0(3) ?
C12 O2 C11 . . 109.3(5) ?
C14 O3 Zn1 . . 118.2(3) ?
C14 O3 H3A . . 109(4) ?
Zn1 O3 H3A . . 118(4) ?
C7 N1 C8 . . 115.5(3) ?
C7 N1 Zn1 . . 124.4(3) ?
C8 N1 Zn1 . . 119.9(3) ?
C10 N2 C13 . . 107.9(4) ?
C10 N2 C9 . . 108.4(4) ?
C13 N2 C9 . . 110.8(4) ?
C6 C1 C2 . . 119.8(4) ?
C6 C1 C7 . . 115.6(4) ?
C2 C1 C7 . . 124.6(4) ?
O1 C2 C3 . . 120.1(4) ?
O1 C2 C1 . . 123.2(4) ?
C3 C2 C1 . . 116.7(4) ?
C4 C3 C2 . . 122.8(4) ?
C4 C3 H3 . . 118.6 ?
C2 C3 H3 . . 118.6 ?
C3 C4 C5 . . 118.9(4) ?
C3 C4 H4 . . 120.5 ?
C5 C4 H4 . . 120.5 ?
C6 C5 C4 . . 121.0(4) ?
C6 C5 Br1 . . 119.3(4) ?
C4 C5 Br1 . . 119.6(4) ?
C5 C6 C1 . . 120.7(4) ?
C5 C6 H6 . . 119.7 ?
C1 C6 H6 . . 119.7 ?
N1 C7 C1 . . 128.3(4) ?
N1 C7 H7 . . 115.8 ?
C1 C7 H7 . . 115.8 ?
N1 C8 C9 . . 111.1(3) ?
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 C8 . . 112.2(4) ?
N2 C9 H9A . . 109.2 ?
C8 C9 H9A . . 109.2 ?
N2 C9 H9B . . 109.2 ?
C8 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
N2 C10 C11 . . 110.1(5) ?
N2 C10 H10A . . 109.6 ?
C11 C10 H10A . . 109.6 ?
N2 C10 H10B . . 109.6 ?
C11 C10 H10B . . 109.6 ?
H10A C10 H10B . . 108.2 ?
O2 C11 C10 . . 112.5(6) ?
O2 C11 H11A . . 109.1 ?
C10 C11 H11A . . 109.1 ?
O2 C11 H11B . . 109.1 ?
C10 C11 H11B . . 109.1 ?
H11A C11 H11B . . 107.8 ?
O2 C12 C13 . . 111.4(6) ?
O2 C12 H12A . . 109.4 ?
C13 C12 H12A . . 109.4 ?
O2 C12 H12B . . 109.4 ?
C13 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
N2 C13 C12 . . 110.2(6) ?
N2 C13 H13A . . 109.6 ?
C12 C13 H13A . . 109.6 ?
N2 C13 H13B . . 109.6 ?
C12 C13 H13B . . 109.6 ?
H13A C13 H13B . . 108.1 ?
O3 C14 H14A . . 109.5 ?
O3 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O3 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 N1 . 2.014(3) y
Zn1 O3 . 2.023(3) y
Zn1 O1 . 2.078(3) y
Zn1 I1 . 2.5346(9) y
Br1 C5 . 1.913(4) ?
O1 C2 . 1.311(5) ?
O2 C12 . 1.394(10) ?
O2 C11 . 1.398(11) ?
O3 C14 . 1.425(6) ?
O3 H3A . 0.84(5) ?
N1 C7 . 1.285(5) ?
N1 C8 . 1.478(5) ?
N2 C10 . 1.472(6) ?
N2 C13 . 1.478(7) ?
N2 C9 . 1.481(5) ?
C1 C6 . 1.411(6) ?
C1 C2 . 1.414(6) ?
C1 C7 . 1.442(6) ?
C2 C3 . 1.405(6) ?
C3 C4 . 1.375(7) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.383(7) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.355(6) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.507(6) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.528(9) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.525(8) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
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
O3 H3A O1 3_666 0.84(5) 1.81(5) 2.649(4) 178(7)
