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#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/69/2226976.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_2226976
loop_
_publ_author_name
'Sauer, Anne M.'
'Mack, Art G.'
'Elnagar, Hassan Y.'
'Fronczek, Frank R.'
_publ_section_title
;
 Ethyl 2-(2,3,4,5,6-Pentabromophenyl)acetate
;
_journal_coeditor_code           JJ2038
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1994
_journal_paper_doi               10.1107/S1600536810025626
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H7 Br5 O2'
_chemical_formula_moiety         'C10 H7 Br5 O2'
_chemical_formula_sum            'C10 H7 Br5 O2'
_chemical_formula_weight         558.71
_chemical_name_systematic
;
Ethyl 2-(2,3,4,5,6-Pentabromophenyl)acetate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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
_cell_angle_beta                 90.993(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.6136(10)
_cell_length_b                   22.548(5)
_cell_length_c                   13.195(2)
_cell_measurement_reflns_used    2027
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.5
_cell_volume                     1372.4(5)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device
'Nonius KappaCCD diffractometer with Oxford Cryostream'
_diffrn_measurement_method       ' ω and φ 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  0.013
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10525
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         3.0
_exptl_absorpt_coefficient_mu    14.626
_exptl_absorpt_correction_T_max  0.273
_exptl_absorpt_correction_T_min  0.121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    2.704
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'needle fragment'
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.65
_refine_diff_density_min         -0.66
_refine_ls_abs_structure_details 'Flack (1983), 1842 Friedel pairs'
_refine_ls_abs_structure_Flack   0.467(13)
_refine_ls_extinction_coef       0.00100(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         3863
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.165
_refine_ls_R_factor_all          0.029
_refine_ls_R_factor_gt           0.025
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0154P)²+2.9894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.052
_refine_ls_wR_factor_ref         0.053
_reflns_number_gt                3676
_reflns_number_total             3863
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jj2038.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2226976
_cod_database_fobs_code          2226976
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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
Br Br1 0.88580(8) 0.721320(18) 0.44969(3) 0.01668(9) Uani d . 1 . .
Br Br2 0.57652(8) 0.735821(17) 0.22457(3) 0.01500(9) Uani d . 1 . .
Br Br3 0.16294(9) 0.628526(18) 0.13378(3) 0.01501(9) Uani d . 1 . .
Br Br4 0.06205(8) 0.507432(18) 0.26957(3) 0.01482(9) Uani d . 1 . .
Br Br5 0.36995(8) 0.495585(18) 0.49436(3) 0.01383(9) Uani d . 1 . .
O O1 0.7331(6) 0.61466(13) 0.7294(2) 0.0136(6) Uani d . 1 . .
O O2 0.3795(6) 0.65392(14) 0.6300(2) 0.0162(6) Uani d . 1 . .
C C1 0.6196(9) 0.60801(18) 0.4523(3) 0.0113(7) Uani d . 1 . .
C C2 0.6548(8) 0.65956(18) 0.3941(3) 0.0115(8) Uani d . 1 . .
C C3 0.5193(9) 0.66594(17) 0.3000(3) 0.0096(7) Uani d . 1 . .
C C4 0.3429(8) 0.62048(18) 0.2616(3) 0.0103(7) Uani d . 1 . .
C C5 0.2983(8) 0.56956(18) 0.3187(3) 0.0110(8) Uani d . 1 . .
C C6 0.4373(8) 0.56364(18) 0.4137(3) 0.0118(8) Uani d . 1 . .
C C7 0.7750(9) 0.60088(18) 0.5534(3) 0.0122(8) Uani d . 1 . .
H H7A 0.9647 0.6213 0.5510 0.015 Uiso calc R 1 . .
H H7B 0.8118 0.5582 0.5660 0.015 Uiso calc R 1 . .
C C8 0.6017(8) 0.62599(17) 0.6398(3) 0.0101(7) Uani d . 1 . .
C C9 0.5844(9) 0.6377(2) 0.8175(3) 0.0148(8) Uani d . 1 . .
H H9A 0.4116 0.6132 0.8316 0.018 Uiso calc R 1 . .
H H9B 0.5200 0.6790 0.8046 0.018 Uiso calc R 1 . .
C C10 0.7928(10) 0.6360(2) 0.9071(3) 0.0170(9) Uani d . 1 . .
H H10A 0.8614 0.5953 0.9176 0.026 Uiso calc R 1 . .
H H10B 0.6938 0.6497 0.9679 0.026 Uiso calc R 1 . .
H H10C 0.9583 0.6620 0.8939 0.026 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'
Br Br -0.2901 2.4595 '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'
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
C8 O1 C9 . . 115.0(3) ?
C6 C1 C2 . . 117.9(4) ?
C6 C1 C7 . . 121.2(4) ?
C2 C1 C7 . . 120.9(4) ?
C3 C2 C1 . . 121.4(4) ?
C3 C2 Br1 . . 120.8(3) ?
C1 C2 Br1 . . 117.8(3) ?
C2 C3 C4 . . 119.9(4) ?
C2 C3 Br2 . . 119.6(3) ?
C4 C3 Br2 . . 120.5(3) ?
C5 C4 C3 . . 120.0(3) ?
C5 C4 Br3 . . 120.0(3) ?
C3 C4 Br3 . . 120.0(3) ?
C4 C5 C6 . . 119.5(4) ?
C4 C5 Br4 . . 121.2(3) ?
C6 C5 Br4 . . 119.3(3) ?
C1 C6 C5 . . 121.3(4) ?
C1 C6 Br5 . . 118.6(3) ?
C5 C6 Br5 . . 120.1(3) ?
C1 C7 C8 . . 112.1(3) ?
C1 C7 H7A . . 109.2 ?
C8 C7 H7A . . 109.2 ?
C1 C7 H7B . . 109.2 ?
C8 C7 H7B . . 109.2 ?
H7A C7 H7B . . 107.9 ?
O2 C8 O1 . . 124.2(4) ?
O2 C8 C7 . . 124.9(4) ?
O1 C8 C7 . . 110.8(3) ?
O1 C9 C10 . . 108.3(3) ?
O1 C9 H9A . . 110.0 ?
C10 C9 H9A . . 110.0 ?
O1 C9 H9B . . 110.0 ?
C10 C9 H9B . . 110.0 ?
H9A C9 H9B . . 108.4 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 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
Br1 C2 . 1.894(4) ?
Br2 C3 . 1.885(4) ?
Br3 C4 . 1.876(4) ?
Br4 C5 . 1.883(4) ?
Br5 C6 . 1.896(4) ?
O1 C8 . 1.344(5) ?
O1 C9 . 1.456(5) ?
O2 C8 . 1.208(5) ?
C1 C6 . 1.397(6) ?
C1 C2 . 1.404(5) ?
C1 C7 . 1.512(5) ?
C2 C3 . 1.388(6) ?
C3 C4 . 1.398(6) ?
C4 C5 . 1.391(6) ?
C5 C6 . 1.404(5) ?
C7 C8 . 1.514(5) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C9 C10 . 1.511(6) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
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
C6 C1 C2 C3 . . . . -1.6(6) ?
C7 C1 C2 C3 . . . . 178.3(4) ?
C6 C1 C2 Br1 . . . . 176.8(3) ?
C7 C1 C2 Br1 . . . . -3.3(5) ?
C1 C2 C3 C4 . . . . 0.2(6) ?
Br1 C2 C3 C4 . . . . -178.1(3) ?
C1 C2 C3 Br2 . . . . -179.5(3) ?
Br1 C2 C3 Br2 . . . . 2.2(5) ?
C2 C3 C4 C5 . . . . 1.5(6) ?
Br2 C3 C4 C5 . . . . -178.9(3) ?
C2 C3 C4 Br3 . . . . -179.3(3) ?
Br2 C3 C4 Br3 . . . . 0.4(5) ?
C3 C4 C5 C6 . . . . -1.6(6) ?
Br3 C4 C5 C6 . . . . 179.1(3) ?
C3 C4 C5 Br4 . . . . 180.0(3) ?
Br3 C4 C5 Br4 . . . . 0.7(5) ?
C2 C1 C6 C5 . . . . 1.5(6) ?
C7 C1 C6 C5 . . . . -178.5(4) ?
C2 C1 C6 Br5 . . . . -176.6(3) ?
C7 C1 C6 Br5 . . . . 3.5(5) ?
C4 C5 C6 C1 . . . . 0.1(6) ?
Br4 C5 C6 C1 . . . . 178.6(3) ?
C4 C5 C6 Br5 . . . . 178.1(3) ?
Br4 C5 C6 Br5 . . . . -3.4(4) ?
C6 C1 C7 C8 . . . . -91.8(5) ?
C2 C1 C7 C8 . . . . 88.3(5) ?
C9 O1 C8 O2 . . . . 1.2(6) ?
C9 O1 C8 C7 . . . . 179.3(3) ?
C1 C7 C8 O2 . . . . -7.1(6) ?
C1 C7 C8 O1 . . . . 174.8(3) ?
C8 O1 C9 C10 . . . . -165.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745461
