#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/72/2227238.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227238
loop_
_publ_author_name
'Najafi, Ezzatollah'
'Amini, Mostafa M.'
'Ng, Seik Weng'
_publ_section_title
;
 Bromido(quinolin-8-ol-κ²N,O)(quinolin-8-olato-κ²N,O)zinc(II)
 methanol monosolvate
;
_journal_coeditor_code           BT5356
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1278
_journal_paper_doi               10.1107/S160053681003672X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Zn Br (C9 H6 N O) (C9 H7 N O)], C H4 O'
_chemical_formula_moiety         'C18 H13 Br N2 O2 Zn, C H4 O'
_chemical_formula_sum            'C19 H17 Br N2 O3 Zn'
_chemical_formula_weight         466.63
_chemical_name_systematic
;
Bromido(quinolin-8-ol-κ²N,O)(quinolin-8-olato-
κ²N,O)zinc(II) methanol monosolvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.2410(10)
_cell_angle_beta                 99.2090(10)
_cell_angle_gamma                109.4700(10)
_cell_formula_units_Z            2
_cell_length_a                   8.4485(7)
_cell_length_b                   8.6968(7)
_cell_length_c                   13.1868(10)
_cell_measurement_reflns_used    3867
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      2.5
_cell_volume                     884.81(12)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEX'
_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  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8392
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.53
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.668
_exptl_absorpt_correction_T_max  0.7106
_exptl_absorpt_correction_T_min  0.4058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.777
_refine_diff_density_min         -0.846
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0457P)²+1.9422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1033
_reflns_number_gt                3354
_reflns_number_total             4022
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5356.cif
_cod_data_source_block           I
_cod_database_code               2227238
_cod_database_fobs_code          2227238
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.45338(5) 0.64466(5) 0.71737(3) 0.01184(12) Uani d . 1 . .
Br Br1 0.58054(4) 0.92415(4) 0.81357(3) 0.01654(11) Uani d . 1 . .
O O1 0.6864(3) 0.6465(3) 0.64187(19) 0.0152(5) Uani d . 1 . .
O O2 0.2092(3) 0.5306(3) 0.73396(19) 0.0145(5) Uani d . 1 . .
H H2 0.1230 0.5461 0.7024 0.022 Uiso calc R 1 . .
O O3 0.9908(3) 0.6800(3) 0.7299(2) 0.0209(6) Uani d . 1 . .
H H3 0.8908 0.6707 0.7016 0.031 Uiso calc R 1 . .
N N1 0.3868(4) 0.6687(4) 0.5653(2) 0.0119(6) Uani d . 1 . .
N N2 0.5025(4) 0.4869(3) 0.8093(2) 0.0121(6) Uani d . 1 . .
C C1 0.5180(4) 0.7280(4) 0.5148(3) 0.0110(6) Uani d . 1 . .
C C2 0.6796(4) 0.7212(4) 0.5573(3) 0.0128(7) Uani d . 1 . .
C C3 0.8163(4) 0.7842(4) 0.5120(3) 0.0150(7) Uani d . 1 . .
H H3A 0.9255 0.7819 0.5415 0.018 Uiso calc R 1 . .
C C4 0.7946(5) 0.8531(5) 0.4209(3) 0.0177(7) Uani d . 1 . .
H H4 0.8897 0.8950 0.3892 0.021 Uiso calc R 1 . .
C C5 0.6384(4) 0.8603(4) 0.3777(3) 0.0151(7) Uani d . 1 . .
H H5 0.6264 0.9080 0.3172 0.018 Uiso calc R 1 . .
C C6 0.4957(5) 0.7963(4) 0.4238(3) 0.0141(7) Uani d . 1 . .
C C7 0.3290(5) 0.7915(4) 0.3821(3) 0.0153(7) Uani d . 1 . .
H H7 0.3085 0.8350 0.3208 0.018 Uiso calc R 1 . .
C C8 0.1969(5) 0.7238(5) 0.4304(3) 0.0173(7) Uani d . 1 . .
H H8 0.0835 0.7166 0.4020 0.021 Uiso calc R 1 . .
C C9 0.2328(4) 0.6652(4) 0.5232(3) 0.0156(7) Uani d . 1 . .
H H9 0.1412 0.6208 0.5571 0.019 Uiso calc R 1 . .
C C10 0.3596(4) 0.4025(4) 0.8429(3) 0.0109(6) Uani d . 1 . .
C C11 0.2035(4) 0.4283(4) 0.8012(3) 0.0138(7) Uani d . 1 . .
C C12 0.0569(4) 0.3427(4) 0.8339(3) 0.0150(7) Uani d . 1 . .
H H12 -0.0481 0.3560 0.8074 0.018 Uiso calc R 1 . .
C C13 0.0599(5) 0.2365(5) 0.9055(3) 0.0165(7) Uani d . 1 . .
H H13 -0.0433 0.1800 0.9263 0.020 Uiso calc R 1 . .
C C14 0.2083(5) 0.2119(4) 0.9464(3) 0.0165(7) Uani d . 1 . .
H H14 0.2079 0.1400 0.9951 0.020 Uiso calc R 1 . .
C C15 0.3606(4) 0.2956(4) 0.9146(3) 0.0128(7) Uani d . 1 . .
C C16 0.5206(5) 0.2803(4) 0.9519(3) 0.0145(7) Uani d . 1 . .
H H16 0.5282 0.2085 0.9996 0.017 Uiso calc R 1 . .
C C17 0.6636(5) 0.3682(4) 0.9194(3) 0.0153(7) Uani d . 1 . .
H H17 0.7716 0.3604 0.9457 0.018 Uiso calc R 1 . .
C C18 0.6497(4) 0.4706(4) 0.8467(3) 0.0134(7) Uani d . 1 . .
H H18 0.7494 0.5301 0.8235 0.016 Uiso calc R 1 . .
C C19 1.0704(5) 0.8335(5) 0.8036(3) 0.0271(9) Uani d . 1 . .
H H19A 1.0933 0.8107 0.8743 0.041 Uiso calc R 1 . .
H H19B 0.9936 0.8967 0.8004 0.041 Uiso calc R 1 . .
H H19C 1.1789 0.8984 0.7867 0.041 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 Zn1 N2 . . 82.51(11) ?
O2 Zn1 N1 . . 95.88(11) ?
N2 Zn1 N1 . . 143.75(11) ?
O2 Zn1 O1 . . 150.98(10) ?
N2 Zn1 O1 . . 90.06(10) ?
N1 Zn1 O1 . . 73.91(10) ?
O2 Zn1 Br1 . . 112.41(7) ?
N2 Zn1 Br1 . . 109.66(8) ?
N1 Zn1 Br1 . . 104.40(8) ?
O1 Zn1 Br1 . . 96.52(6) ?
C2 O1 Zn1 . . 108.4(2) ?
C11 O2 Zn1 . . 111.3(2) ?
C11 O2 H2 . . 124.4 ?
Zn1 O2 H2 . . 124.4 ?
C19 O3 H3 . . 109.5 ?
C9 N1 C1 . . 118.4(3) ?
C9 N1 Zn1 . . 122.8(2) ?
C1 N1 Zn1 . . 117.2(2) ?
C18 N2 C10 . . 119.0(3) ?
C18 N2 Zn1 . . 129.8(2) ?
C10 N2 Zn1 . . 110.8(2) ?
N1 C1 C2 . . 117.6(3) ?
N1 C1 C6 . . 122.0(3) ?
C2 C1 C6 . . 120.3(3) ?
O1 C2 C3 . . 124.0(3) ?
O1 C2 C1 . . 116.0(3) ?
C3 C2 C1 . . 119.9(3) ?
C2 C3 C4 . . 119.9(3) ?
C2 C3 H3A . . 120.0 ?
C4 C3 H3A . . 120.0 ?
C5 C4 C3 . . 121.2(3) ?
C5 C4 H4 . . 119.4 ?
C3 C4 H4 . . 119.4 ?
C4 C5 C6 . . 119.7(3) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C7 C6 C5 . . 123.5(3) ?
C7 C6 C1 . . 117.5(3) ?
C5 C6 C1 . . 118.9(3) ?
C8 C7 C6 . . 119.8(3) ?
C8 C7 H7 . . 120.1 ?
C6 C7 H7 . . 120.1 ?
C7 C8 C9 . . 118.8(3) ?
C7 C8 H8 . . 120.6 ?
C9 C8 H8 . . 120.6 ?
N1 C9 C8 . . 123.4(3) ?
N1 C9 H9 . . 118.3 ?
C8 C9 H9 . . 118.3 ?
N2 C10 C15 . . 122.9(3) ?
N2 C10 C11 . . 116.5(3) ?
C15 C10 C11 . . 120.7(3) ?
O2 C11 C12 . . 124.4(3) ?
O2 C11 C10 . . 118.4(3) ?
C12 C11 C10 . . 117.2(3) ?
C11 C12 C13 . . 121.4(3) ?
C11 C12 H12 . . 119.3 ?
C13 C12 H12 . . 119.3 ?
C14 C13 C12 . . 121.9(3) ?
C14 C13 H13 . . 119.0 ?
C12 C13 H13 . . 119.0 ?
C13 C14 C15 . . 118.6(3) ?
C13 C14 H14 . . 120.7 ?
C15 C14 H14 . . 120.7 ?
C10 C15 C14 . . 120.1(3) ?
C10 C15 C16 . . 116.4(3) ?
C14 C15 C16 . . 123.5(3) ?
C17 C16 C15 . . 120.2(3) ?
C17 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
C16 C17 C18 . . 119.3(3) ?
C16 C17 H17 . . 120.4 ?
C18 C17 H17 . . 120.4 ?
N2 C18 C17 . . 122.2(3) ?
N2 C18 H18 . . 118.9 ?
C17 C18 H18 . . 118.9 ?
O3 C19 H19A . . 109.5 ?
O3 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O3 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 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 O2 . 2.030(2) ?
Zn1 N2 . 2.040(3) ?
Zn1 N1 . 2.050(3) ?
Zn1 O1 . 2.340(2) ?
Zn1 Br1 . 2.3911(5) ?
O1 C2 . 1.362(4) ?
O2 C11 . 1.328(4) ?
O2 H2 . 0.8400 ?
O3 C19 . 1.430(5) ?
O3 H3 . 0.8400 ?
N1 C9 . 1.319(4) ?
N1 C1 . 1.372(4) ?
N2 C18 . 1.322(4) ?
N2 C10 . 1.361(4) ?
C1 C2 . 1.414(5) ?
C1 C6 . 1.418(5) ?
C2 C3 . 1.368(5) ?
C3 C4 . 1.422(5) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.376(5) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.416(5) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.412(5) ?
C7 C8 . 1.372(5) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.411(5) ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
C10 C15 . 1.409(5) ?
C10 C11 . 1.445(5) ?
C11 C12 . 1.383(5) ?
C12 C13 . 1.404(5) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.378(5) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.410(5) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.417(5) ?
C16 C17 . 1.364(5) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.406(5) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
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
_geom_hbond_publ_flag
O2 H2 O3 1_455 0.84 1.90 2.585(4) 137 yes
O3 H3 O1 . 0.84 1.71 2.551(4) 178 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 Zn1 O1 C2 . . . . 94.6(3) ?
N2 Zn1 O1 C2 . . . . 169.1(2) ?
N1 Zn1 O1 C2 . . . . 22.0(2) ?
Br1 Zn1 O1 C2 . . . . -81.1(2) ?
N2 Zn1 O2 C11 . . . . 6.3(2) ?
N1 Zn1 O2 C11 . . . . 149.9(2) ?
O1 Zn1 O2 C11 . . . . 82.7(3) ?
Br1 Zn1 O2 C11 . . . . -101.9(2) ?
O2 Zn1 N1 C9 . . . . 21.6(3) ?
N2 Zn1 N1 C9 . . . . 106.9(3) ?
O1 Zn1 N1 C9 . . . . 173.8(3) ?
Br1 Zn1 N1 C9 . . . . -93.4(3) ?
O2 Zn1 N1 C1 . . . . -173.6(2) ?
N2 Zn1 N1 C1 . . . . -88.3(3) ?
O1 Zn1 N1 C1 . . . . -21.3(2) ?
Br1 Zn1 N1 C1 . . . . 71.4(2) ?
O2 Zn1 N2 C18 . . . . -178.6(3) ?
N1 Zn1 N2 C18 . . . . 91.6(3) ?
O1 Zn1 N2 C18 . . . . 29.5(3) ?
Br1 Zn1 N2 C18 . . . . -67.5(3) ?
O2 Zn1 N2 C10 . . . . -6.2(2) ?
N1 Zn1 N2 C10 . . . . -96.0(3) ?
O1 Zn1 N2 C10 . . . . -158.1(2) ?
Br1 Zn1 N2 C10 . . . . 104.9(2) ?
C9 N1 C1 C2 . . . . -176.1(3) ?
Zn1 N1 C1 C2 . . . . 18.4(4) ?
C9 N1 C1 C6 . . . . 4.7(5) ?
Zn1 N1 C1 C6 . . . . -160.8(3) ?
Zn1 O1 C2 C3 . . . . 161.4(3) ?
Zn1 O1 C2 C1 . . . . -20.0(3) ?
N1 C1 C2 O1 . . . . 3.7(4) ?
C6 C1 C2 O1 . . . . -177.1(3) ?
N1 C1 C2 C3 . . . . -177.7(3) ?
C6 C1 C2 C3 . . . . 1.6(5) ?
O1 C2 C3 C4 . . . . 177.1(3) ?
C1 C2 C3 C4 . . . . -1.4(5) ?
C2 C3 C4 C5 . . . . 1.0(6) ?
C3 C4 C5 C6 . . . . -0.8(5) ?
C4 C5 C6 C7 . . . . -177.0(3) ?
C4 C5 C6 C1 . . . . 0.9(5) ?
N1 C1 C6 C7 . . . . -4.1(5) ?
C2 C1 C6 C7 . . . . 176.7(3) ?
N1 C1 C6 C5 . . . . 177.9(3) ?
C2 C1 C6 C5 . . . . -1.3(5) ?
C5 C6 C7 C8 . . . . 178.5(3) ?
C1 C6 C7 C8 . . . . 0.6(5) ?
C6 C7 C8 C9 . . . . 2.0(5) ?
C1 N1 C9 C8 . . . . -1.9(5) ?
Zn1 N1 C9 C8 . . . . 162.7(3) ?
C7 C8 C9 N1 . . . . -1.4(6) ?
C18 N2 C10 C15 . . . . -1.2(5) ?
Zn1 N2 C10 C15 . . . . -174.5(3) ?
C18 N2 C10 C11 . . . . 178.6(3) ?
Zn1 N2 C10 C11 . . . . 5.2(4) ?
Zn1 O2 C11 C12 . . . . 175.2(3) ?
Zn1 O2 C11 C10 . . . . -5.4(4) ?
N2 C10 C11 O2 . . . . 0.1(5) ?
C15 C10 C11 O2 . . . . 179.8(3) ?
N2 C10 C11 C12 . . . . 179.6(3) ?
C15 C10 C11 C12 . . . . -0.7(5) ?
O2 C11 C12 C13 . . . . -179.9(3) ?
C10 C11 C12 C13 . . . . 0.7(5) ?
C11 C12 C13 C14 . . . . -0.2(6) ?
C12 C13 C14 C15 . . . . -0.3(5) ?
N2 C10 C15 C14 . . . . 179.9(3) ?
C11 C10 C15 C14 . . . . 0.2(5) ?
N2 C10 C15 C16 . . . . 0.5(5) ?
C11 C10 C15 C16 . . . . -179.2(3) ?
C13 C14 C15 C10 . . . . 0.3(5) ?
C13 C14 C15 C16 . . . . 179.7(3) ?
C10 C15 C16 C17 . . . . 1.0(5) ?
C14 C15 C16 C17 . . . . -178.5(3) ?
C15 C16 C17 C18 . . . . -1.7(5) ?
C10 N2 C18 C17 . . . . 0.4(5) ?
Zn1 N2 C18 C17 . . . . 172.3(3) ?
C16 C17 C18 N2 . . . . 1.0(5) ?
