#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/92/2229217.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_2229217
loop_
_publ_author_name
'Zeng, Wu-Lan'
_publ_section_title
;
 3-(4-Bromobenzylidene)-1,5-dioxaspiro[5.5]undecane-2,4-dione
;
_journal_coeditor_code           SI2324
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o426
_journal_paper_doi               10.1107/S1600536811001516
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H15 Br O4'
_chemical_formula_moiety         'C16 H15 Br O4'
_chemical_formula_sum            'C16 H15 Br O4'
_chemical_formula_weight         351.18
_chemical_name_systematic
;
3-(4-Bromobenzylidene)-1,5-dioxaspiro[5.5]undecane-2,4-dione
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6008(13)
_cell_length_b                   16.784(3)
_cell_length_c                   13.424(3)
_cell_measurement_reflns_used    2042
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.03
_cell_volume                     1487.2(5)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0649
_diffrn_reflns_av_sigmaI/netI    0.0828
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12420
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    2.777
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.344
_refine_ls_abs_structure_details 'Flack (1983), 1459 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.033(13)
_refine_ls_extinction_coef       0.0088(18)
_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   0.933
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3243
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0603P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                2042
_reflns_number_total             3243
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            si2324.cif
_cod_data_source_block           I
_cod_database_code               2229217
_cod_database_fobs_code          2229217
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, 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 -0.30705(7) 0.16937(3) 0.44191(6) 0.0845(2) Uani d . 1 . .
O O4 0.3239(4) 0.18964(18) -0.1213(2) 0.0495(7) Uani d U 1 . .
C C8 0.2952(5) 0.1895(3) -0.0213(4) 0.0474(9) Uani d U 1 . .
C C10 0.5373(7) 0.0731(3) -0.0208(4) 0.0683(13) Uani d . 1 . .
O O3 0.5363(4) 0.07733(19) -0.1204(2) 0.0628(8) Uani d . 1 . .
O O2 0.2192(4) 0.24707(17) 0.0163(3) 0.0565(7) Uani d . 1 . .
C C7 0.3358(7) 0.0974(3) 0.1252(4) 0.0625(11) Uani d . 1 . .
H H7A 0.4214 0.0577 0.1490 0.075 Uiso calc R 1 . .
C C4 0.1814(6) 0.1207(3) 0.1977(4) 0.0562(11) Uani d . 1 . .
C C9 0.3812(7) 0.1202(3) 0.0332(4) 0.0574(11) Uani d . 1 . .
C C12 0.3662(6) 0.1150(2) -0.1684(4) 0.0504(10) Uani d . 1 . .
C C6 -0.1475(7) 0.1696(3) 0.2454(5) 0.0654(13) Uani d . 1 . .
H H6A -0.2712 0.1920 0.2277 0.079 Uiso calc R 1 . .
C C5 -0.0046(7) 0.1545(2) 0.1731(4) 0.0626(11) Uani d . 1 . .
H H5A -0.0327 0.1670 0.1071 0.075 Uiso calc R 1 . .
C C1 -0.1088(7) 0.1517(2) 0.3444(3) 0.0569(10) Uani d . 1 . .
C C13 0.4385(7) 0.1343(3) -0.2731(4) 0.0669(13) Uani d . 1 . .
H H13A 0.5485 0.1725 -0.2697 0.080 Uiso calc R 1 . .
H H13B 0.4898 0.0862 -0.3043 0.080 Uiso calc R 1 . .
C C11 0.1829(5) 0.0624(2) -0.1692(3) 0.0540(10) Uani d . 1 . .
H H11A 0.1366 0.0539 -0.1015 0.065 Uiso calc R 1 . .
H H11B 0.2182 0.0110 -0.1973 0.065 Uiso calc R 1 . .
O O1 0.6638(6) 0.0322(3) 0.0197(3) 0.0997(14) Uani d . 1 . .
C C3 0.2160(7) 0.1015(3) 0.2968(4) 0.0635(12) Uani d . 1 . .
H H3A 0.3378 0.0775 0.3143 0.076 Uiso calc R 1 . .
C C2 0.0755(7) 0.1171(3) 0.3698(4) 0.0690(12) Uani d . 1 . .
H H2A 0.1036 0.1046 0.4358 0.083 Uiso calc R 1 . .
C C16 0.0131(6) 0.0998(3) -0.2304(4) 0.0694(13) Uani d . 1 . .
H H16A -0.1028 0.0643 -0.2316 0.083 Uiso calc R 1 . .
H H16B -0.0287 0.1495 -0.1997 0.083 Uiso calc R 1 . .
C C14 0.2691(10) 0.1683(3) -0.3360(5) 0.0853(18) Uani d . 1 . .
H H14A 0.3159 0.1742 -0.4041 0.102 Uiso calc R 1 . .
H H14B 0.2334 0.2207 -0.3112 0.102 Uiso calc R 1 . .
C C15 0.0829(9) 0.1154(4) -0.3347(4) 0.0873(17) Uani d . 1 . .
H H15A -0.0252 0.1409 -0.3719 0.105 Uiso calc R 1 . .
H H15B 0.1140 0.0651 -0.3670 0.105 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 O4 C12 . . 117.6(4) ?
O2 C8 O4 . . 118.3(4) ?
O2 C8 C9 . . 125.6(5) ?
O4 C8 C9 . . 115.8(4) ?
O1 C10 O3 . . 118.8(5) ?
O1 C10 C9 . . 124.1(5) ?
O3 C10 C9 . . 117.1(4) ?
C10 O3 C12 . . 118.3(4) ?
C9 C7 C4 . . 134.4(4) ?
C9 C7 H7A . . 112.8 ?
C4 C7 H7A . . 112.8 ?
C3 C4 C5 . . 117.8(5) ?
C3 C4 C7 . . 117.5(4) ?
C5 C4 C7 . . 124.5(5) ?
C7 C9 C10 . . 117.2(4) ?
C7 C9 C8 . . 126.7(4) ?
C10 C9 C8 . . 116.1(5) ?
O4 C12 O3 . . 109.8(3) ?
O4 C12 C11 . . 111.2(3) ?
O3 C12 C11 . . 112.0(3) ?
O4 C12 C13 . . 106.5(3) ?
O3 C12 C13 . . 105.2(3) ?
C11 C12 C13 . . 111.8(4) ?
C5 C6 C1 . . 120.6(4) ?
C5 C6 H6A . . 119.7 ?
C1 C6 H6A . . 119.7 ?
C6 C5 C4 . . 120.8(5) ?
C6 C5 H5A . . 119.6 ?
C4 C5 H5A . . 119.6 ?
C6 C1 C2 . . 119.1(5) ?
C6 C1 Br1 . . 120.4(4) ?
C2 C1 Br1 . . 120.4(4) ?
C14 C13 C12 . . 111.4(4) ?
C14 C13 H13A . . 109.3 ?
C12 C13 H13A . . 109.3 ?
C14 C13 H13B . . 109.3 ?
C12 C13 H13B . . 109.3 ?
H13A C13 H13B . . 108.0 ?
C12 C11 C16 . . 110.8(4) ?
C12 C11 H11A . . 109.5 ?
C16 C11 H11A . . 109.5 ?
C12 C11 H11B . . 109.5 ?
C16 C11 H11B . . 109.5 ?
H11A C11 H11B . . 108.1 ?
C2 C3 C4 . . 121.9(4) ?
C2 C3 H3A . . 119.0 ?
C4 C3 H3A . . 119.0 ?
C3 C2 C1 . . 119.7(5) ?
C3 C2 H2A . . 120.2 ?
C1 C2 H2A . . 120.2 ?
C15 C16 C11 . . 110.4(4) ?
C15 C16 H16A . . 109.6 ?
C11 C16 H16A . . 109.6 ?
C15 C16 H16B . . 109.6 ?
C11 C16 H16B . . 109.6 ?
H16A C16 H16B . . 108.1 ?
C13 C14 C15 . . 111.8(4) ?
C13 C14 H14A . . 109.3 ?
C15 C14 H14A . . 109.3 ?
C13 C14 H14B . . 109.3 ?
C15 C14 H14B . . 109.3 ?
H14A C14 H14B . . 107.9 ?
C16 C15 C14 . . 111.3(4) ?
C16 C15 H15A . . 109.4 ?
C14 C15 H15A . . 109.4 ?
C16 C15 H15B . . 109.4 ?
C14 C15 H15B . . 109.4 ?
H15A C15 H15B . . 108.0 ?
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 C1 . 1.875(5) ?
O4 C8 . 1.355(5) ?
O4 C12 . 1.431(5) ?
C8 O2 . 1.201(5) ?
C8 C9 . 1.487(6) ?
C10 O1 . 1.210(6) ?
C10 O3 . 1.338(6) ?
C10 C9 . 1.487(7) ?
O3 C12 . 1.441(5) ?
C7 C9 . 1.328(7) ?
C7 C4 . 1.462(7) ?
C7 H7A . 0.9300 ?
C4 C3 . 1.387(6) ?
C4 C5 . 1.392(6) ?
C12 C11 . 1.498(6) ?
C12 C13 . 1.520(6) ?
C6 C5 . 1.377(8) ?
C6 C1 . 1.385(7) ?
C6 H6A . 0.9300 ?
C5 H5A . 0.9300 ?
C1 C2 . 1.391(6) ?
C13 C14 . 1.513(8) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C11 C16 . 1.525(6) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C3 C2 . 1.374(7) ?
C3 H3A . 0.9300 ?
C2 H2A . 0.9300 ?
C16 C15 . 1.497(7) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C14 C15 . 1.517(9) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
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
C5 H5A O2 . 0.93 2.45 3.004(2) 117 no
C7 H7A O1 . 0.93 2.40 2.812(2) 106 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2964547
