##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(1'S,6'S,8'S,9'R)-9'-Bromo-12'-oxaspiro[1,3-
dioxolane-2,4'-tricyclo[6.3.1.0^1,6^]dodecane]
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H19 Br O3'
_chemical_formula_sum     'C13 H19 Br O3'
_chemical_formula_iupac     'C13 H19 Br O3'
_chemical_formula_weight     303.19
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     11.0159(3)
_cell_length_b     12.6619(3)
_cell_length_c     10.2763(2)
_cell_angle_alpha     90.00
_cell_angle_beta     117.0440(10)
_cell_angle_gamma     90.00
_cell_volume     1276.63(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4277
_cell_measurement_theta_min     2.63
_cell_measurement_theta_max     24.21
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.577
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     624
_exptl_absorpt_coefficient_mu     3.214
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.4456
_exptl_absorpt_correction_T_max     0.6442
_exptl_special_details     ?
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11338
_diffrn_reflns_av_R_equivalents     0.0265
_diffrn_reflns_av_sigmaI/netI     0.0215
_diffrn_reflns_theta_min     2.08
_diffrn_reflns_theta_max     25.44
_diffrn_reflns_theta_full     25.44
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2368
_reflns_number_gt     1859
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0428
_refine_ls_R_factor_gt     0.0296
_refine_ls_wR_factor_gt     0.0704
_refine_ls_wR_factor_ref     0.0762
_refine_ls_goodness_of_fit_ref     1.022
_refine_ls_restrained_S_all     1.022
_refine_ls_number_reflns     2368
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     .
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0436P)²+0.2892P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.247
_refine_diff_density_min     -0.317
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Br Br1 0.70444(3) 0.11259(2) 0.71170(3) 0.06222(13) Uani d . 1 1 . .
    O O1 0.66345(15) 0.35583(12) 0.61783(15) 0.0391(4) Uani d . 1 1 . .
    O O2 0.7122(2) 0.73040(14) 0.57865(18) 0.0640(5) Uani d . 1 1 . .
    O O3 0.84162(18) 0.72842(13) 0.82550(18) 0.0529(4) Uani d . 1 1 . .
    C C1 0.6947(2) 0.24005(18) 0.8181(2) 0.0424(5) Uani d . 1 1 . .
    H H1 0.6541 0.2205 0.8820 0.051 Uiso calc R 1 1 . .
    C C11 0.6034(2) 0.32101(18) 0.7079(2) 0.0404(5) Uani d . 1 1 . .
    H H11 0.5125 0.2915 0.6480 0.048 Uiso calc R 1 1 . .
    C C13 0.7789(3) 0.8290(2) 0.7886(3) 0.0547(7) Uani d . 1 1 . .
    H H13A 0.8441 0.8848 0.8377 0.066 Uiso calc R 1 1 . .
    H H13B 0.7043 0.8344 0.8138 0.066 Uiso calc R 1 1 . .
    C C4 0.7757(2) 0.42229(17) 0.7136(2) 0.0348(5) Uani d . 1 1 . .
    C C2 0.8358(2) 0.2838(2) 0.9109(3) 0.0479(6) Uani d . 1 1 . .
    H H2A 0.8985 0.2259 0.9566 0.057 Uiso calc R 1 1 . .
    H H2B 0.8345 0.3275 0.9878 0.057 Uiso calc R 1 1 . .
    C C7 0.7737(2) 0.66148(18) 0.7019(2) 0.0439(5) Uani d . 1 1 . .
    C C5 0.8222(3) 0.48727(18) 0.6187(3) 0.0482(6) Uani d . 1 1 . .
    H H5A 0.8906 0.4482 0.6038 0.058 Uiso calc R 1 1 . .
    H H5B 0.7453 0.4997 0.5239 0.058 Uiso calc R 1 1 . .
    C C3 0.8863(2) 0.34948(19) 0.8204(3) 0.0439(5) Uani d . 1 1 . .
    H H3A 0.9638 0.3916 0.8854 0.053 Uiso calc R 1 1 . .
    H H3B 0.9165 0.3025 0.7663 0.053 Uiso calc R 1 1 . .
    C C9 0.7113(2) 0.49168(18) 0.7904(2) 0.0371(5) Uani d . 1 1 . .
    H H9 0.7779 0.5045 0.8922 0.044 Uiso calc R 1 1 . .
    C C8 0.6607(2) 0.59613(19) 0.7111(3) 0.0463(6) Uani d . 1 1 . .
    H H8A 0.6205 0.6371 0.7613 0.056 Uiso calc R 1 1 . .
    H H8B 0.5900 0.5822 0.6130 0.056 Uiso calc R 1 1 . .
    C C6 0.8809(3) 0.59178(19) 0.6909(3) 0.0510(6) Uani d . 1 1 . .
    H H6A 0.9192 0.6282 0.6350 0.061 Uiso calc R 1 1 . .
    H H6B 0.9540 0.5790 0.7881 0.061 Uiso calc R 1 1 . .
    C C12 0.7281(3) 0.8340(2) 0.6265(3) 0.0637(7) Uani d . 1 1 . .
    H H12A 0.6419 0.8713 0.5805 0.076 Uiso calc R 1 1 . .
    H H12B 0.7934 0.8703 0.6032 0.076 Uiso calc R 1 1 . .
    C C10 0.5940(2) 0.4216(2) 0.7848(3) 0.0467(6) Uani d . 1 1 . .
    H H10A 0.6061 0.4061 0.8825 0.056 Uiso calc R 1 1 . .
    H H10B 0.5065 0.4560 0.7300 0.056 Uiso calc R 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Br1 0.0895(3) 0.04123(17) 0.0633(2) -0.00573(13) 0.04119(18) -0.00022(12)
    O1 0.0431(9) 0.0423(8) 0.0294(8) -0.0076(7) 0.0142(7) -0.0022(6)
    O2 0.0890(14) 0.0478(10) 0.0373(10) -0.0019(10) 0.0129(10) 0.0008(8)
    O3 0.0545(10) 0.0443(9) 0.0425(9) 0.0021(8) 0.0068(8) -0.0056(7)
    C1 0.0489(14) 0.0453(13) 0.0364(12) -0.0032(10) 0.0223(11) 0.0011(10)
    C11 0.0321(12) 0.0482(13) 0.0380(13) -0.0066(10) 0.0134(10) 0.0023(10)
    C13 0.0602(17) 0.0420(14) 0.0590(17) -0.0012(12) 0.0246(14) -0.0077(12)
    C4 0.0335(12) 0.0383(11) 0.0327(12) -0.0032(9) 0.0153(10) -0.0047(10)
    C2 0.0453(14) 0.0514(14) 0.0364(13) 0.0075(11) 0.0094(11) 0.0049(11)
    C7 0.0488(14) 0.0384(12) 0.0372(13) -0.0014(11) 0.0132(11) -0.0032(10)
    C5 0.0584(16) 0.0430(13) 0.0569(15) -0.0040(11) 0.0382(13) -0.0051(11)
    C3 0.0313(12) 0.0458(12) 0.0504(14) 0.0011(10) 0.0149(11) -0.0047(11)
    C9 0.0325(12) 0.0443(12) 0.0337(12) 0.0026(9) 0.0144(10) -0.0042(10)
    C8 0.0370(12) 0.0462(14) 0.0493(15) 0.0067(10) 0.0140(11) -0.0024(11)
    C6 0.0516(15) 0.0453(14) 0.0621(16) -0.0098(11) 0.0311(13) -0.0067(12)
    C12 0.075(2) 0.0490(16) 0.0596(17) 0.0066(14) 0.0237(15) 0.0063(13)
    C10 0.0399(13) 0.0549(14) 0.0508(14) 0.0033(11) 0.0255(12) 0.0035(12)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 . 1.979(2) ?
    O1 C11 . 1.430(3) ?
    O1 C4 . 1.449(3) ?
    O2 C12 . 1.384(3) ?
    O2 C7 . 1.430(3) ?
    O3 C13 . 1.416(3) ?
    O3 C7 . 1.424(3) ?
    C1 C2 . 1.512(3) ?
    C1 C11 . 1.519(3) ?
    C1 H1 . 0.9800 ?
    C11 C10 . 1.528(3) ?
    C11 H11 . 0.9800 ?
    C13 C12 . 1.498(4) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C4 C3 . 1.524(3) ?
    C4 C5 . 1.531(3) ?
    C4 C9 . 1.552(3) ?
    C2 C3 . 1.529(3) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C7 C6 . 1.519(3) ?
    C7 C8 . 1.533(4) ?
    C5 C6 . 1.511(3) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C9 C8 . 1.520(3) ?
    C9 C10 . 1.547(3) ?
    C9 H9 . 0.9800 ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
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
    C11 O1 C4 . . 104.04(15) ?
    C12 O2 C7 . . 109.37(19) ?
    C13 O3 C7 . . 107.58(18) ?
    C2 C1 C11 . . 111.43(19) ?
    C2 C1 Br1 . . 110.40(16) ?
    C11 C1 Br1 . . 108.80(15) ?
    C2 C1 H1 . . 108.7 ?
    C11 C1 H1 . . 108.7 ?
    Br1 C1 H1 . . 108.7 ?
    O1 C11 C1 . . 110.25(17) ?
    O1 C11 C10 . . 103.78(17) ?
    C1 C11 C10 . . 110.77(19) ?
    O1 C11 H11 . . 110.6 ?
    C1 C11 H11 . . 110.6 ?
    C10 C11 H11 . . 110.6 ?
    O3 C13 C12 . . 103.1(2) ?
    O3 C13 H13A . . 111.2 ?
    C12 C13 H13A . . 111.2 ?
    O3 C13 H13B . . 111.2 ?
    C12 C13 H13B . . 111.2 ?
    H13A C13 H13B . . 109.1 ?
    O1 C4 C3 . . 107.08(17) ?
    O1 C4 C5 . . 107.98(17) ?
    C3 C4 C5 . . 113.22(18) ?
    O1 C4 C9 . . 103.17(16) ?
    C3 C4 C9 . . 112.15(18) ?
    C5 C4 C9 . . 112.49(18) ?
    C1 C2 C3 . . 111.68(18) ?
    C1 C2 H2A . . 109.3 ?
    C3 C2 H2A . . 109.3 ?
    C1 C2 H2B . . 109.3 ?
    C3 C2 H2B . . 109.3 ?
    H2A C2 H2B . . 107.9 ?
    O3 C7 O2 . . 105.78(18) ?
    O3 C7 C6 . . 107.5(2) ?
    O2 C7 C6 . . 111.1(2) ?
    O3 C7 C8 . . 112.2(2) ?
    O2 C7 C8 . . 108.2(2) ?
    C6 C7 C8 . . 111.80(19) ?
    C6 C5 C4 . . 110.50(19) ?
    C6 C5 H5A . . 109.5 ?
    C4 C5 H5A . . 109.5 ?
    C6 C5 H5B . . 109.5 ?
    C4 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 108.1 ?
    C4 C3 C2 . . 111.99(18) ?
    C4 C3 H3A . . 109.2 ?
    C2 C3 H3A . . 109.2 ?
    C4 C3 H3B . . 109.2 ?
    C2 C3 H3B . . 109.2 ?
    H3A C3 H3B . . 107.9 ?
    C8 C9 C10 . . 112.51(19) ?
    C8 C9 C4 . . 111.12(18) ?
    C10 C9 C4 . . 102.94(18) ?
    C8 C9 H9 . . 110.0 ?
    C10 C9 H9 . . 110.0 ?
    C4 C9 H9 . . 110.0 ?
    C9 C8 C7 . . 113.1(2) ?
    C9 C8 H8A . . 108.9 ?
    C7 C8 H8A . . 108.9 ?
    C9 C8 H8B . . 108.9 ?
    C7 C8 H8B . . 108.9 ?
    H8A C8 H8B . . 107.8 ?
    C5 C6 C7 . . 111.8(2) ?
    C5 C6 H6A . . 109.3 ?
    C7 C6 H6A . . 109.3 ?
    C5 C6 H6B . . 109.3 ?
    C7 C6 H6B . . 109.3 ?
    H6A C6 H6B . . 107.9 ?
    O2 C12 C13 . . 106.1(2) ?
    O2 C12 H12A . . 110.5 ?
    C13 C12 H12A . . 110.5 ?
    O2 C12 H12B . . 110.5 ?
    C13 C12 H12B . . 110.5 ?
    H12A C12 H12B . . 108.7 ?
    C11 C10 C9 . . 104.20(17) ?
    C11 C10 H10A . . 110.9 ?
    C9 C10 H10A . . 110.9 ?
    C11 C10 H10B . . 110.9 ?
    C9 C10 H10B . . 110.9 ?
    H10A C10 H10B . . 108.9 ?
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
    C11 H11 O2 3_666 0.98 2.53 3.445(3) 156.0
    C1 H1 O1 4_566 0.98 2.57 3.471(3) 153.3
data_global
_journal_date_recd_electronic     2012-06-15
_journal_date_accepted     2012-06-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      8
_journal_page_first     o2411
_journal_page_last     o2412
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812029777
_journal_coeditor_code     DS2204
_publ_contact_author_name     'Goverdhan Mehta'
_publ_contact_author_address
;
Department of Organic Chemistry
Indian Institute of Science
Bangalore 560 012
Karnataka
India
School of Chemistry
University of Hyderabad
Hyderabad 500 046
A.P. India
;
_publ_contact_author_email     'gmsc@uohyd.ernet.in, gm@orgchem.iisc.ernet.in'
_publ_contact_author_fax     '+91 4023012460'
_publ_contact_author_phone     '+91 4023010785'
_publ_section_title
;\
(1'S,6'S,8'S,9'R)-9'-Bromo-12'-oxaspiro[1,3-\
dioxolane-2,4'-tricyclo[6.3.1.0^1,6^]dodecane]
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Mehta, Goverdhan' .
;
Department of Organic Chemistry, Indian Institute of Science
Bangalore 560 012
Karnataka
India
School of Chemistry
University of Hyderabad
Hyderabad 500 046
A.P. India
;
    'Khan, Tabrez Babu' .
;
Department of Organic Chemistry, Indian Institute of Science
Bangalore 560 012
Karnataka
India
School of Chemistry
University of Hyderabad
Hyderabad 500 046
A.P. India
;
