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#$Date: 2016-03-25 13:35:19 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179852 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/48/7014899.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_7014899
loop_
_publ_author_name
'Jones, Roderick C.'
'Chojnacka, Maja W.'
'Quail, J. Wilson'
'Gardiner, Michael G.'
'Decken, Andreas'
'Yates, Brian F.'
'Gossage, Robert A.'
_publ_section_title
;
 Oxazoles revisited: On the nature of binding of benzoxazole and
 2-methylbenzoxazole with the zinc and palladium halides.
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1594
_journal_page_last               1600
_journal_paper_doi               10.1039/c0dt01266a
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C14 H10 Br2 N2 O2 Zn'
_chemical_formula_sum            'C14 H10 Br2 N2 O2 Zn'
_chemical_formula_weight         463.43
_chemical_name_systematic
;
?
;
_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                 91.279(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.9848(4)
_cell_length_b                   7.0380(2)
_cell_length_c                   13.5346(3)
_cell_measurement_reflns_used    3748
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1522.28(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Xtal3.7(Hall et al., 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'maXus(Mackay et al., 1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21346
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.866
_exptl_absorpt_correction_T_max  0.410
_exptl_absorpt_correction_T_min  0.310
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'Shelxtl 6.10 (Bruker-AXS, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.022
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chip
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       0.0053(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0322
_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)+(0.0255P)²+2.0033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0729
_reflns_number_gt                2760
_reflns_number_total             3488
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            C0DT01266A.TXT
_cod_data_source_block           1153
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7014899
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.24379(2) 0.51320(5) 0.33796(3) 0.02206(11) Uani 1 1 d . . .
Br1 Br 0.24626(2) 0.83967(5) 0.37420(3) 0.03354(12) Uani 1 1 d . . .
Br2 Br 0.26675(2) 0.42703(6) 0.17273(3) 0.03638(12) Uani 1 1 d . . .
O1 O 0.43800(14) 0.1679(3) 0.44873(18) 0.0277(5) Uani 1 1 d . . .
O2 O 0.06468(15) 0.1743(4) 0.4764(2) 0.0331(6) Uani 1 1 d . . .
N1 N 0.33519(16) 0.3757(4) 0.4199(2) 0.0227(6) Uani 1 1 d . . .
N2 N 0.14094(16) 0.3842(4) 0.3946(2) 0.0225(6) Uani 1 1 d . . .
C1 C 0.37448(19) 0.4236(5) 0.5114(2) 0.0220(7) Uani 1 1 d . . .
C2 C 0.3601(2) 0.5692(5) 0.5777(3) 0.0262(7) Uani 1 1 d . . .
H2 H 0.3165 0.6592 0.5672 0.031 Uiso 1 1 calc R . .
C3 C 0.4132(2) 0.5761(5) 0.6603(3) 0.0299(8) Uani 1 1 d . . .
H3 H 0.4051 0.6721 0.7085 0.036 Uiso 1 1 calc R . .
C4 C 0.4785(2) 0.4449(6) 0.6744(3) 0.0314(8) Uani 1 1 d . . .
H4 H 0.5142 0.4565 0.7311 0.038 Uiso 1 1 calc R . .
C5 C 0.4925(2) 0.2996(5) 0.6083(3) 0.0296(8) Uani 1 1 d . . .
H5 H 0.5365 0.2101 0.6177 0.036 Uiso 1 1 calc R . .
C6 C 0.4383(2) 0.2932(5) 0.5275(2) 0.0239(7) Uani 1 1 d . . .
C7 C 0.3754(2) 0.2282(5) 0.3891(3) 0.0261(7) Uani 1 1 d . . .
H7 H 0.3616 0.1669 0.3283 0.031 Uiso 1 1 calc R . .
C11 C 0.0090(2) 0.2904(5) 0.4249(2) 0.0248(7) Uani 1 1 d . . .
C12 C -0.0767(2) 0.2849(5) 0.4231(3) 0.0311(8) Uani 1 1 d . . .
H12 H -0.1073 0.1936 0.4592 0.037 Uiso 1 1 calc R . .
C13 C -0.1153(2) 0.4210(6) 0.3650(3) 0.0350(9) Uani 1 1 d . . .
H13 H -0.1747 0.4227 0.3598 0.042 Uiso 1 1 calc R . .
C14 C -0.0699(2) 0.5565(6) 0.3136(3) 0.0385(9) Uani 1 1 d . . .
H14 H -0.0994 0.6492 0.2755 0.046 Uiso 1 1 calc R . .
C15 C 0.0162(2) 0.5604(6) 0.3163(3) 0.0342(9) Uani 1 1 d . . .
H15 H 0.0470 0.6526 0.2809 0.041 Uiso 1 1 calc R . .
C16 C 0.05539(19) 0.4216(5) 0.3736(2) 0.0213(7) Uani 1 1 d . . .
C17 C 0.1406(2) 0.2411(5) 0.4535(3) 0.0284(7) Uani 1 1 d . . .
H17 H 0.1908 0.1860 0.4793 0.034 Uiso 1 1 calc R . .
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'
Br Br -0.2901 2.4595 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Zn1 N1 99.02(11) . . ?
N2 Zn1 Br1 111.50(8) . . ?
N1 Zn1 Br1 109.82(8) . . ?
N2 Zn1 Br2 112.68(8) . . ?
N1 Zn1 Br2 105.50(8) . . ?
Br1 Zn1 Br2 116.62(2) . . ?
C7 O1 C6 104.6(3) . . ?
C17 O2 C11 104.5(3) . . ?
C7 N1 C1 105.0(3) . . ?
C7 N1 Zn1 123.7(2) . . ?
C1 N1 Zn1 130.9(2) . . ?
C17 N2 C16 104.6(3) . . ?
C17 N2 Zn1 126.6(2) . . ?
C16 N2 Zn1 128.6(2) . . ?
C2 C1 C6 121.4(3) . . ?
C2 C1 N1 131.7(3) . . ?
C6 C1 N1 106.9(3) . . ?
C1 C2 C3 116.1(3) . . ?
C1 C2 H2 121.9 . . ?
C3 C2 H2 121.9 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 122.0(3) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 115.4(3) . . ?
C4 C5 H5 122.3 . . ?
C6 C5 H5 122.3 . . ?
C5 C6 O1 128.5(3) . . ?
C5 C6 C1 123.4(3) . . ?
O1 C6 C1 108.1(3) . . ?
N1 C7 O1 115.4(3) . . ?
N1 C7 H7 122.3 . . ?
O1 C7 H7 122.3 . . ?
C12 C11 C16 123.9(3) . . ?
C12 C11 O2 128.6(3) . . ?
C16 C11 O2 107.6(3) . . ?
C11 C12 C13 115.2(3) . . ?
C11 C12 H12 122.4 . . ?
C13 C12 H12 122.4 . . ?
C12 C13 C14 121.9(3) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C15 C14 C13 122.2(4) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C14 C15 C16 116.0(3) . . ?
C14 C15 H15 122.0 . . ?
C16 C15 H15 122.0 . . ?
C11 C16 C15 120.8(3) . . ?
C11 C16 N2 107.6(3) . . ?
C15 C16 N2 131.7(3) . . ?
N2 C17 O2 115.7(3) . . ?
N2 C17 H17 122.1 . . ?
O2 C17 H17 122.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N2 2.042(3) . ?
Zn1 N1 2.056(3) . ?
Zn1 Br1 2.3496(5) . ?
Zn1 Br2 2.3538(5) . ?
O1 C7 1.340(4) . ?
O1 C6 1.384(4) . ?
O2 C17 1.344(4) . ?
O2 C11 1.385(4) . ?
N1 C7 1.296(4) . ?
N1 C1 1.417(4) . ?
N2 C17 1.285(4) . ?
N2 C16 1.415(4) . ?
C1 C2 1.384(5) . ?
C1 C6 1.386(5) . ?
C2 C3 1.389(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(5) . ?
C5 H5 0.9500 . ?
C7 H7 0.9500 . ?
C11 C12 1.371(5) . ?
C11 C16 1.381(5) . ?
C12 C13 1.376(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(5) . ?
C15 H15 0.9500 . ?
C17 H17 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Zn1 N1 C7 96.1(3) . . . . ?
Br1 Zn1 N1 C7 -147.1(3) . . . . ?
Br2 Zn1 N1 C7 -20.6(3) . . . . ?
N2 Zn1 N1 C1 -91.5(3) . . . . ?
Br1 Zn1 N1 C1 25.3(3) . . . . ?
Br2 Zn1 N1 C1 151.8(3) . . . . ?
N1 Zn1 N2 C17 -8.5(3) . . . . ?
Br1 Zn1 N2 C17 -124.1(3) . . . . ?
Br2 Zn1 N2 C17 102.6(3) . . . . ?
N1 Zn1 N2 C16 176.1(3) . . . . ?
Br1 Zn1 N2 C16 60.5(3) . . . . ?
Br2 Zn1 N2 C16 -72.9(3) . . . . ?
C7 N1 C1 C2 178.6(4) . . . . ?
Zn1 N1 C1 C2 5.2(5) . . . . ?
C7 N1 C1 C6 0.2(4) . . . . ?
Zn1 N1 C1 C6 -173.3(2) . . . . ?
C6 C1 C2 C3 0.0(5) . . . . ?
N1 C1 C2 C3 -178.3(3) . . . . ?
C1 C2 C3 C4 1.2(5) . . . . ?
C2 C3 C4 C5 -1.5(6) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 O1 178.4(3) . . . . ?
C4 C5 C6 C1 0.9(5) . . . . ?
C7 O1 C6 C5 -177.3(3) . . . . ?
C7 O1 C6 C1 0.5(3) . . . . ?
C2 C1 C6 C5 -1.2(5) . . . . ?
N1 C1 C6 C5 177.5(3) . . . . ?
C2 C1 C6 O1 -179.1(3) . . . . ?
N1 C1 C6 O1 -0.4(4) . . . . ?
C1 N1 C7 O1 0.1(4) . . . . ?
Zn1 N1 C7 O1 174.2(2) . . . . ?
C6 O1 C7 N1 -0.4(4) . . . . ?
C17 O2 C11 C12 -179.3(4) . . . . ?
C17 O2 C11 C16 0.0(4) . . . . ?
C16 C11 C12 C13 0.3(5) . . . . ?
O2 C11 C12 C13 179.5(3) . . . . ?
C11 C12 C13 C14 -1.2(6) . . . . ?
C12 C13 C14 C15 1.2(7) . . . . ?
C13 C14 C15 C16 -0.2(6) . . . . ?
C12 C11 C16 C15 0.6(6) . . . . ?
O2 C11 C16 C15 -178.8(3) . . . . ?
C12 C11 C16 N2 179.3(3) . . . . ?
O2 C11 C16 N2 0.0(4) . . . . ?
C14 C15 C16 C11 -0.6(6) . . . . ?
C14 C15 C16 N2 -179.0(4) . . . . ?
C17 N2 C16 C11 0.1(4) . . . . ?
Zn1 N2 C16 C11 176.3(2) . . . . ?
C17 N2 C16 C15 178.6(4) . . . . ?
Zn1 N2 C16 C15 -5.2(5) . . . . ?
C16 N2 C17 O2 -0.1(4) . . . . ?
Zn1 N2 C17 O2 -176.4(2) . . . . ?
C11 O2 C17 N2 0.1(4) . . . . ?
