#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/28/2212818.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_2212818
loop_
_publ_author_name
'Li, Zhen-Huan'
'Guo, Ming-Lin'
_publ_section_title
;
 (2-Acetoxy-3,5-dibromophenyl)methylene diacetate
;
_journal_coeditor_code           CI2306
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1971
_journal_page_last               o1972
_journal_paper_doi               10.1107/S1600536807012822
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H12 Br2 O6'
_chemical_formula_moiety         'C13 H12 Br2 O6'
_chemical_formula_sum            'C13 H12 Br2 O6'
_chemical_formula_weight         424.03
_chemical_name_systematic
;
(2-Acetoxy-3,5-dibromophenyl)methylene diacetate
;
_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                63.099(3)
_cell_angle_beta                 70.287(2)
_cell_angle_gamma                77.467(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4489(16)
_cell_length_b                   9.9453(18)
_cell_length_c                   10.3242(18)
_cell_measurement_reflns_used    1810
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.12
_cell_measurement_theta_min      2.30
_cell_volume                     812.1(2)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4228
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.30
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.012
_exptl_absorpt_correction_T_max  0.446
_exptl_absorpt_correction_T_min  0.310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick,1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.618
_refine_diff_density_min         -0.516
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2839
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0468P)²+0.2022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0896
_reflns_number_gt                2166
_reflns_number_total             2839
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2306.cif
_cod_data_source_block           I
_cod_database_code               2212818
_cod_database_fobs_code          2212818
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
Br Br1 0.30434(5) 0.71484(5) -0.35845(4) 0.05405(16) Uani d . 1 . .
Br Br2 -0.05905(5) 0.21989(5) -0.05707(5) 0.06163(17) Uani d . 1 . .
O O1 0.0691(3) 0.1630(3) 0.2010(3) 0.0442(6) Uani d . 1 . .
O O2 0.4326(3) 0.2084(3) 0.1760(3) 0.0506(7) Uani d . 1 . .
O O3 0.3455(3) 0.4246(3) 0.2082(3) 0.0544(7) Uani d . 1 A .
O O4 0.2205(4) -0.0117(3) 0.1269(3) 0.0601(8) Uani d . 1 . .
O O5 0.3499(5) 0.0283(4) 0.4035(4) 0.1115(16) Uani d . 1 . .
O O6 0.1469(11) 0.4157(13) 0.3958(18) 0.104(5) Uani d PD 0.61(3) A 1
O O6' 0.234(4) 0.355(2) 0.4518(9) 0.108(9) Uani d PD 0.39(3) A 2
C C1 0.2990(4) 0.3035(4) 0.1998(4) 0.0441(9) Uani d . 1 . .
H H1 0.2242 0.2484 0.2933 0.053 Uiso calc R 1 . .
C C2 0.2384(4) 0.3600(4) 0.0652(4) 0.0387(8) Uani d . 1 . .
C C3 0.1338(4) 0.2822(4) 0.0659(4) 0.0393(8) Uani d . 1 . .
C C4 0.0833(4) 0.3293(4) -0.0602(4) 0.0421(9) Uani d . 1 . .
C C5 0.1349(4) 0.4562(4) -0.1882(4) 0.0464(10) Uani d . 1 . .
H H5 0.1013 0.4877 -0.2732 0.056 Uiso calc R 1 . .
C C6 0.2376(4) 0.5356(4) -0.1874(4) 0.0416(9) Uani d . 1 . .
C C7 0.2911(4) 0.4893(4) -0.0636(4) 0.0401(9) Uani d . 1 . .
H H7 0.3613 0.5434 -0.0658 0.048 Uiso calc R 1 . .
C C8 0.1185(5) 0.0177(4) 0.2166(4) 0.0428(9) Uani d . 1 . .
C C9 0.0239(5) -0.0915(5) 0.3608(5) 0.0600(12) Uani d . 1 . .
H H9A 0.0225 -0.1823 0.3503 0.090 Uiso calc R 1 . .
H H9B -0.0772 -0.0465 0.3820 0.090 Uiso calc R 1 . .
H H9C 0.0657 -0.1155 0.4422 0.090 Uiso calc R 1 . .
C C10 0.4455(5) 0.0705(5) 0.2883(5) 0.0578(11) Uani d . 1 . .
C C11 0.5874(6) -0.0164(6) 0.2466(6) 0.0815(16) Uani d . 1 . .
H H11A 0.5911 -0.1143 0.3282 0.122 Uiso calc R 1 . .
H H11B 0.6714 0.0364 0.2266 0.122 Uiso calc R 1 . .
H H11C 0.5920 -0.0280 0.1578 0.122 Uiso calc R 1 . .
C C12 0.2753(7) 0.4570(6) 0.3275(6) 0.0781(15) Uani d D 1 . .
C C13 0.3413(7) 0.5836(6) 0.3207(7) 0.0891(18) Uani d . 1 A .
H H13A 0.3468 0.6674 0.2243 0.134 Uiso calc R 1 . .
H H13B 0.4407 0.5509 0.3340 0.134 Uiso calc R 1 . .
H H13C 0.2789 0.6141 0.3994 0.134 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
C8 O1 C3 118.3(3)
C10 O2 C1 118.1(3)
C12 O3 C1 118.8(3)
O3 C1 O2 105.4(3)
O3 C1 C2 110.6(3)
O2 C1 C2 107.8(3)
O3 C1 H1 111.0
O2 C1 H1 111.0
C2 C1 H1 111.0
C3 C2 C7 119.3(3)
C3 C2 C1 120.3(3)
C7 C2 C1 120.4(3)
C2 C3 C4 120.6(3)
C2 C3 O1 118.7(3)
C4 C3 O1 120.4(3)
C5 C4 C3 120.7(3)
C5 C4 Br2 119.5(3)
C3 C4 Br2 119.8(3)
C4 C5 C6 118.5(3)
C4 C5 H5 120.8
C6 C5 H5 120.8
C7 C6 C5 121.7(3)
C7 C6 Br1 118.8(3)
C5 C6 Br1 119.5(3)
C6 C7 C2 119.2(3)
C6 C7 H7 120.4
C2 C7 H7 120.4
O4 C8 O1 123.0(3)
O4 C8 C9 127.2(4)
O1 C8 C9 109.8(4)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O5 C10 O2 121.7(5)
O5 C10 C11 126.2(4)
O2 C10 C11 112.1(4)
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O6' C12 O6 52.4(10)
O6' C12 O3 119.7(10)
O6 C12 O3 116.3(7)
O6' C12 C13 116.6(8)
O6 C12 C13 127.7(6)
O3 C12 C13 111.7(5)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C6 1.892(3)
Br2 C4 1.889(3)
O1 C8 1.370(5)
O1 C3 1.403(4)
O2 C10 1.351(5)
O2 C1 1.424(5)
O3 C12 1.332(6)
O3 C1 1.416(5)
O4 C8 1.180(5)
O5 C10 1.181(5)
O6 C12 1.231(7)
O6' C12 1.218(8)
C1 C2 1.505(5)
C1 H1 0.98
C2 C3 1.378(5)
C2 C7 1.397(5)
C3 C4 1.383(5)
C4 C5 1.378(5)
C5 C6 1.382(5)
C5 H5 0.93
C6 C7 1.380(5)
C7 H7 0.93
C8 C9 1.502(5)
C9 H9A 0.96
C9 H9B 0.96
C9 H9C 0.96
C10 C11 1.474(7)
C11 H11A 0.96
C11 H11B 0.96
C11 H11C 0.96
C12 C13 1.487(7)
C13 H13A 0.96
C13 H13B 0.96
C13 H13C 0.96
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
C12 O3 C1 O2 -126.7(4)
C12 O3 C1 C2 117.0(4)
C10 O2 C1 O3 111.8(3)
C10 O2 C1 C2 -130.0(3)
O3 C1 C2 C3 -153.2(3)
O2 C1 C2 C3 92.0(4)
O3 C1 C2 C7 28.8(5)
O2 C1 C2 C7 -86.0(4)
C7 C2 C3 C4 1.3(6)
C1 C2 C3 C4 -176.7(4)
C7 C2 C3 O1 -172.9(3)
C1 C2 C3 O1 9.1(5)
C8 O1 C3 C2 -103.7(4)
C8 O1 C3 C4 82.1(4)
C2 C3 C4 C5 -1.0(6)
O1 C3 C4 C5 173.1(3)
C2 C3 C4 Br2 179.5(3)
O1 C3 C4 Br2 -6.4(5)
C3 C4 C5 C6 -0.3(6)
Br2 C4 C5 C6 179.2(3)
C4 C5 C6 C7 1.3(6)
C4 C5 C6 Br1 -177.5(3)
C5 C6 C7 C2 -1.0(6)
Br1 C6 C7 C2 177.8(3)
C3 C2 C7 C6 -0.3(6)
C1 C2 C7 C6 177.7(4)
C3 O1 C8 O4 6.0(5)
C3 O1 C8 C9 -173.8(3)
C1 O2 C10 O5 0.0(6)
C1 O2 C10 C11 178.6(4)
C1 O3 C12 O6' 36.7(18)
C1 O3 C12 O6 -23.2(11)
C1 O3 C12 C13 178.2(4)
