#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/02/2240249.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_2240249
loop_
_publ_author_name
'Martins, Lucimara Julio'
'de Simoni, Deborah'
'Aparicio, Ricardo'
'Coelho, Fernando'
_publ_section_title
;
 Crystal structure of methyl
 2-(2H-1,3-benzodioxol-5-yl)-7,9-dibromo-8-oxo-1-oxaspiro[4.5]deca-2,6,9-triene-3-carboxylate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1275
_journal_page_last               o1276
_journal_paper_doi               10.1107/S1600536814024763
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C18 H12 Br2 O6'
_chemical_formula_moiety         'C18 H12 Br2 O6'
_chemical_formula_sum            'C18 H12 Br2 O6'
_chemical_formula_weight         484.10
_chemical_name_systematic
2-(2H-1,3-Benzodioxol-5-yl)-7,9-dibromo-8-oxo-1-oxaspiro[4.5]deca-2,6,9-triene-3-carboxylate
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                84.485(4)
_cell_angle_beta                 80.007(5)
_cell_angle_gamma                78.077(4)
_cell_formula_units_Z            2
_cell_length_a                   8.1929(13)
_cell_length_b                   8.4811(14)
_cell_length_c                   12.761(2)
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.1
_cell_measurement_theta_min      3.2
_cell_volume                     852.7(2)
_computing_cell_refinement
;
SAINT (Bruker, 2010)
;
_computing_data_collection
;
APEX2 (Bruker, 2010)
;
_computing_data_reduction
;
SAINT (Bruker, 2010)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2006)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2003), PLATON (Spek, 2009) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXLE (Hübschle et al, 2011) and SHELXL2014 (Sheldrick,
2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27788
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.338
_diffrn_reflns_theta_min         3.031
_exptl_absorpt_coefficient_mu    4.787
_exptl_absorpt_correction_T_max  0.5147
_exptl_absorpt_correction_T_min  0.3087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2010)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.885
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.390
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         7098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0181
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0245P)²+0.2583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0455
_refine_ls_wR_factor_ref         0.0472
_reflns_number_gt                6288
_reflns_number_total             7098
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5413sup1.cif
_cod_data_source_block           I
_cod_database_code               2240249
_cod_database_fobs_code          2240249
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.309
_shelx_estimated_absorpt_t_max   0.515
_shelxl_version_number           2.014
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_occupancy
Br Br1 0.81611(2) 1.44904(2) 0.62579(2) 0.01782(3) Uani d 1
Br Br2 0.72560(2) 0.85491(2) 0.49155(2) 0.01638(3) Uani d 1
O O1 0.75814(11) 1.20677(9) 0.48397(6) 0.01915(14) Uani d 1
O O2 0.81234(9) 0.93071(9) 0.86474(5) 0.01450(12) Uani d 1
O O3 0.57197(10) 0.68379(9) 1.33065(6) 0.01608(13) Uani d 1
O O4 0.81596(9) 0.50402(9) 1.26861(6) 0.01609(13) Uani d 1
O O5 1.24024(10) 0.67487(10) 1.01728(6) 0.01916(14) Uani d 1
O O6 1.37041(9) 0.72220(9) 0.84968(6) 0.01529(12) Uani d 1
C C1 0.79228(12) 1.13898(10) 0.56785(7) 0.01214(14) Uani d 1
C C2 0.83286(12) 1.22429(10) 0.65381(7) 0.01222(14) Uani d 1
C C3 0.88062(12) 1.14902(11) 0.74351(7) 0.01357(15) Uani d 1
H H3 0.8963 1.2114 0.7977 0.016 Uiso calc 1
C C4 0.91021(12) 0.96878(11) 0.76100(7) 0.01264(15) Uani d 1
C C5 0.91926(12) 0.83972(10) 0.92957(7) 0.01135(14) Uani d 1
C C6 0.82769(11) 0.79788(10) 1.03513(7) 0.01106(14) Uani d 1
C C7 0.88494(12) 0.65586(11) 1.09690(7) 0.01202(14) Uani d 1
H H7 0.9864 0.5828 1.0731 0.014 Uiso calc 1
C C8 0.78592(12) 0.62914(11) 1.19325(7) 0.01182(14) Uani d 1
C C9 0.63896(12) 0.73620(11) 1.23042(7) 0.01254(14) Uani d 1
C C10 1.09810(12) 0.89627(12) 0.77135(7) 0.01504(16) Uani d 1
H H10A 1.1501 0.8183 0.7164 0.018 Uiso calc 1
H H10B 1.1655 0.9820 0.7656 0.018 Uiso calc 1
C C11 1.08297(12) 0.81321(11) 0.88176(7) 0.01190(14) Uani d 1
C C12 0.66357(14) 0.52054(12) 1.34563(8) 0.01708(17) Uani d 1
H H12A 0.6912 0.5003 1.4188 0.020 Uiso calc 1
H H12B 0.5948 0.4422 1.3344 0.020 Uiso calc 1
C C13 0.58111(12) 0.87530(11) 1.17181(8) 0.01435(15) Uani d 1
H H13 0.4809 0.9486 1.1975 0.017 Uiso calc 1
C C14 0.67762(12) 0.90331(11) 1.07223(7) 0.01288(15) Uani d 1
H H14 0.6401 0.9965 1.0287 0.015 Uiso calc 1
C C15 1.23289(12) 0.72953(11) 0.92621(7) 0.01239(14) Uani d 1
C C16 1.52864(13) 0.64225(14) 0.88280(9) 0.02125(19) Uani d 1
H H16A 1.5418 0.6880 0.9478 0.032 Uiso calc 1
H H16B 1.6222 0.6580 0.8261 0.032 Uiso calc 1
H H16C 1.5291 0.5265 0.8969 0.032 Uiso calc 1
C C17 0.85126(12) 0.88535(11) 0.68028(7) 0.01319(15) Uani d 1
H H17 0.8524 0.7728 0.6918 0.016 Uiso calc 1
C C18 0.79718(12) 0.96291(10) 0.59287(7) 0.01170(14) Uani 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'
O O 0.0106 0.0060 '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
C5 O2 C4 109.46(7)
C9 O3 C12 104.80(7)
C8 O4 C12 105.13(7)
C15 O6 C16 115.44(8)
O1 C1 C2 122.93(8)
O1 C1 C18 122.50(8)
C2 C1 C18 114.57(8)
C3 C2 C1 123.31(8)
C3 C2 Br1 121.81(7)
C1 C2 Br1 114.87(6)
C2 C3 C4 121.73(8)
C2 C3 H3 119.1
C4 C3 H3 119.1
O2 C4 C3 107.32(7)
O2 C4 C17 106.47(7)
C3 C4 C17 114.33(8)
O2 C4 C10 105.43(7)
C3 C4 C10 111.56(8)
C17 C4 C10 111.13(8)
C11 C5 O2 112.55(8)
C11 C5 C6 135.58(8)
O2 C5 C6 111.85(8)
C14 C6 C7 120.45(8)
C14 C6 C5 117.27(8)
C7 C6 C5 122.27(8)
C8 C7 C6 116.53(8)
C8 C7 H7 121.7
C6 C7 H7 121.7
O4 C8 C7 127.79(8)
O4 C8 C9 109.53(8)
C7 C8 C9 122.61(8)
O3 C9 C13 128.16(9)
O3 C9 C8 109.94(8)
C13 C9 C8 121.85(8)
C11 C10 C4 102.30(7)
C11 C10 H10A 111.3
C4 C10 H10A 111.3
C11 C10 H10B 111.3
C4 C10 H10B 111.3
H10A C10 H10B 109.2
C5 C11 C15 128.64(8)
C5 C11 C10 110.13(8)
C15 C11 C10 121.07(8)
O4 C12 O3 106.94(7)
O4 C12 H12A 110.3
O3 C12 H12A 110.3
O4 C12 H12B 110.3
O3 C12 H12B 110.3
H12A C12 H12B 108.6
C9 C13 C14 116.62(9)
C9 C13 H13 121.7
C14 C13 H13 121.7
C6 C14 C13 121.91(8)
C6 C14 H14 119.0
C13 C14 H14 119.0
O5 C15 O6 122.92(9)
O5 C15 C11 127.60(9)
O6 C15 C11 109.47(8)
O6 C16 H16A 109.5
O6 C16 H16B 109.5
H16A C16 H16B 109.5
O6 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C18 C17 C4 122.64(8)
C18 C17 H17 118.7
C4 C17 H17 118.7
C17 C18 C1 122.38(8)
C17 C18 Br2 121.91(7)
C1 C18 Br2 115.70(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.8863(9)
Br2 C18 1.8887(9)
O1 C1 1.2139(11)
O2 C5 1.3772(11)
O2 C4 1.4684(11)
O3 C9 1.3721(11)
O3 C12 1.4444(12)
O4 C8 1.3746(11)
O4 C12 1.4397(13)
O5 C15 1.2158(11)
O6 C15 1.3520(11)
O6 C16 1.4459(13)
C1 C2 1.4887(13)
C1 C18 1.4904(12)
C2 C3 1.3351(13)
C3 C4 1.4985(13)
C3 H3 0.9500
C4 C17 1.4996(13)
C4 C10 1.5585(14)
C5 C11 1.3563(13)
C5 C6 1.4733(12)
C6 C14 1.4001(13)
C6 C7 1.4158(12)
C7 C8 1.3775(13)
C7 H7 0.9500
C8 C9 1.3900(13)
C9 C13 1.3777(13)
C10 C11 1.5104(13)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C15 1.4623(13)
C12 H12A 0.9900
C12 H12B 0.9900
C13 C14 1.4026(13)
C13 H13 0.9500
C14 H14 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C17 C18 1.3354(13)
C17 H17 0.9500
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
C3 H3 O5 2_777 0.95 2.61 3.4272(13) 143.8
C7 H7 O5 . 0.95 2.34 2.9441(13) 120.7
C10 H10A O1 2_776 0.99 2.55 3.3995(13) 143.4
C12 H12A Br1 1_546 0.99 2.96 3.9411(12) 172.7
C12 H12A O1 1_546 0.99 2.53 3.0852(13) 115.5
C13 H13 O2 2_677 0.95 2.63 3.3909(13) 136.9
C16 H16C O5 2_867 0.98 2.59 3.2434(14) 124.1
C17 H17 Br1 1_545 0.95 3.03 3.9069(11) 153.4
C14 H14 O2 . 0.95 2.36 2.6937(12) 100.3
