#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/31/2223177.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_2223177
loop_
_publ_author_name
'Xia, Ai-Bao'
'Tang, Jie'
'Jiang, Jun-Rong'
'Wang, Yi-Feng'
'Luo, Shu-Ping'
_publ_section_title
;
 (R)-7-Bromo-2,3,4,4a-tetrahydro-1H-xanthen-1-one
;
_journal_coeditor_code           PV2187
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2091
_journal_paper_doi               10.1107/S1600536809030244
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H11 Br O2'
_chemical_formula_moiety         'C13 H11 Br O2'
_chemical_formula_sum            'C13 H11 Br O2'
_chemical_formula_weight         279.13
_chemical_name_systematic
;
(R)-7-Bromo-2,3,4,4a-tetrahydro-1H-xanthen-1-one
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.7110(12)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   7.5419(4)
_cell_length_b                   6.9039(3)
_cell_length_c                   10.7634(5)
_cell_measurement_reflns_used    4299
_cell_measurement_temperature    296.0(10)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.2
_cell_volume                     559.26(5)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 2006)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 2006)'
_computing_data_reduction
'CrystalStructure (Rigaku/MSC and Rigaku, 2007)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'CrystalStructure (Rigaku/MSC and Rigaku, 2007) and PLATON Spek (2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5496
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_exptl_absorpt_coefficient_mu    3.666
_exptl_absorpt_correction_T_max  0.386
_exptl_absorpt_correction_T_min  0.252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             280.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.64
_refine_diff_density_min         -0.88
_refine_ls_abs_structure_details 'Flack (1983), 1145 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       0.035(3)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2525
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.02P)²+P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1019
_reflns_number_gt                1772
_reflns_number_total             2525
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            pv2187.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2223177
_cod_database_fobs_code          2223177
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +x,+y,+z
2 -x,1/2+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 0.96613(6) 0.67049(12) 0.66752(4) 0.0633(2) Uani d . 1.00 . .
O O1 0.5964(5) 0.6274(8) -0.0423(3) 0.0656(16) Uani d . 1.00 . .
O O2 0.2944(3) 0.6625(11) 0.3348(2) 0.0473(7) Uani d . 1.00 . .
C C1 0.4600(6) 0.6384(11) 0.0116(4) 0.0505(16) Uani d . 1.00 . .
C C2 0.2803(7) 0.6187(12) -0.0570(4) 0.063(2) Uani d . 1.00 . .
C C3 0.1314(6) 0.7222(8) 0.0028(4) 0.0557(18) Uani d . 1.00 . .
C C4 0.1286(5) 0.6734(16) 0.1395(3) 0.0519(11) Uani d . 1.00 . .
C C5 0.2999(6) 0.7335(7) 0.2089(4) 0.0440(13) Uani d . 1.00 . .
C C6 0.4495(4) 0.6742(14) 0.4075(3) 0.0401(8) Uani d . 1.00 . .
C C7 0.4396(5) 0.6820(14) 0.5352(3) 0.0434(10) Uani d . 1.00 . .
C C8 0.5937(5) 0.6827(14) 0.6123(3) 0.0454(11) Uani d . 1.00 . .
C C9 0.7562(5) 0.6759(14) 0.5602(3) 0.0412(9) Uani d . 1.00 . .
C C10 0.7694(5) 0.6637(16) 0.4334(3) 0.0425(9) Uani d . 1.00 . .
C C11 0.6136(4) 0.6623(14) 0.3548(3) 0.0393(8) Uani d . 1.00 . .
C C12 0.6132(5) 0.6402(11) 0.2208(4) 0.0447(15) Uani d . 1.00 . .
C C13 0.4640(4) 0.6636(15) 0.1494(3) 0.0413(9) Uani d . 1.00 . .
H H5 0.3034 0.8753 0.2117 0.053 Uiso c R 1.00 . .
H H7 0.3294 0.6868 0.5692 0.052 Uiso c R 1.00 . .
H H8 0.5879 0.6877 0.6983 0.054 Uiso c R 1.00 . .
H H10 0.8801 0.6564 0.4004 0.051 Uiso c R 1.00 . .
H H12 0.7181 0.6095 0.1844 0.054 Uiso c R 1.00 . .
H H21 0.2509 0.4820 -0.0622 0.075 Uiso c R 1.00 . .
H H22 0.2883 0.6705 -0.1402 0.075 Uiso c R 1.00 . .
H H31 0.0191 0.6841 -0.0391 0.067 Uiso c R 1.00 . .
H H32 0.1475 0.8609 -0.0060 0.067 Uiso c R 1.00 . .
H H41 0.0304 0.7408 0.1742 0.062 Uiso c R 1.00 . .
H H42 0.1129 0.5347 0.1486 0.062 Uiso c R 1.00 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -0.290 2.459
;
International Tables for Crystallography
(1992, 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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 O2 C6 . . . 116.2(3) ?
O1 C1 C2 . . . 121.5(4) ?
O1 C1 C13 . . . 121.2(4) ?
C2 C1 C13 . . . 117.2(4) ?
C1 C2 C3 . . . 114.7(4) ?
C2 C3 C4 . . . 111.5(5) ?
C3 C4 C5 . . . 110.8(4) ?
O2 C5 C4 . . . 107.2(4) ?
O2 C5 C13 . . . 111.3(4) ?
C4 C5 C13 . . . 113.7(4) ?
O2 C6 C7 . . . 118.2(3) ?
O2 C6 C11 . . . 120.8(3) ?
C7 C6 C11 . . . 120.8(3) ?
C6 C7 C8 . . . 120.0(3) ?
C7 C8 C9 . . . 119.2(3) ?
Br1 C9 C8 . . . 118.7(2) ?
Br1 C9 C10 . . . 119.4(2) ?
C8 C9 C10 . . . 121.8(3) ?
C9 C10 C11 . . . 119.1(3) ?
C6 C11 C10 . . . 119.0(3) ?
C6 C11 C12 . . . 117.7(3) ?
C10 C11 C12 . . . 123.3(3) ?
C11 C12 C13 . . . 120.6(4) ?
C1 C13 C5 . . . 119.6(3) ?
C1 C13 C12 . . . 121.5(4) ?
C5 C13 C12 . . . 118.7(3) ?
C1 C2 H21 . . . 108.1 no
C1 C2 H22 . . . 108.1 no
C3 C2 H21 . . . 108.1 no
C3 C2 H22 . . . 108.1 no
H21 C2 H22 . . . 109.5 no
C2 C3 H31 . . . 109.0 no
C2 C3 H32 . . . 109.0 no
C4 C3 H31 . . . 109.0 no
C4 C3 H32 . . . 109.0 no
H31 C3 H32 . . . 109.5 no
C3 C4 H41 . . . 109.1 no
C3 C4 H42 . . . 109.1 no
C5 C4 H41 . . . 109.1 no
C5 C4 H42 . . . 109.1 no
H41 C4 H42 . . . 109.5 no
O2 C5 H5 . . . 108.1 no
C4 C5 H5 . . . 108.1 no
C13 C5 H5 . . . 108.1 no
C6 C7 H7 . . . 120.0 no
C8 C7 H7 . . . 120.0 no
C7 C8 H8 . . . 120.4 no
C9 C8 H8 . . . 120.4 no
C9 C10 H10 . . . 120.4 no
C11 C10 H10 . . . 120.4 no
C11 C12 H12 . . . 119.7 no
C13 C12 H12 . . . 119.7 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C9 . . 1.899(3) ?
O1 C1 . . 1.215(6) ?
O2 C5 . . 1.444(5) ?
O2 C6 . . 1.367(4) ?
C1 C2 . . 1.507(7) ?
C1 C13 . . 1.492(6) ?
C2 C3 . . 1.510(8) ?
C3 C4 . . 1.511(6) ?
C4 C5 . . 1.508(6) ?
C5 C13 . . 1.509(6) ?
C6 C7 . . 1.382(5) ?
C6 C11 . . 1.397(5) ?
C7 C8 . . 1.384(5) ?
C8 C9 . . 1.381(5) ?
C9 C10 . . 1.377(5) ?
C10 C11 . . 1.403(5) ?
C11 C12 . . 1.450(5) ?
C12 C13 . . 1.330(5) ?
C2 H21 . . 0.970 no
C2 H22 . . 0.970 no
C3 H31 . . 0.970 no
C3 H32 . . 0.970 no
C4 H41 . . 0.970 no
C4 H42 . . 0.970 no
C5 H5 . . 0.980 no
C7 H7 . . 0.930 no
C8 H8 . . 0.930 no
C10 H10 . . 0.930 no
C12 H12 . . 0.930 no
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
C5 O2 C6 C7 . . . . 155.2(7) ?
C5 O2 C6 C11 . . . . -30.1(12) ?
C6 O2 C5 C4 . . . . 169.6(7) ?
C6 O2 C5 C13 . . . . 44.7(8) ?
O1 C1 C2 C3 . . . . -153.0(6) ?
O1 C1 C13 C5 . . . . 162.5(7) ?
O1 C1 C13 C12 . . . . -12.2(13) ?
C2 C1 C13 C5 . . . . -20.1(11) ?
C2 C1 C13 C12 . . . . 165.2(8) ?
C13 C1 C2 C3 . . . . 29.6(9) ?
C1 C2 C3 C4 . . . . -50.2(8) ?
C2 C3 C4 C5 . . . . 60.7(8) ?
C3 C4 C5 O2 . . . . -173.7(6) ?
C3 C4 C5 C13 . . . . -50.2(9) ?
O2 C5 C13 C1 . . . . 151.9(7) ?
O2 C5 C13 C12 . . . . -33.3(10) ?
C4 C5 C13 C1 . . . . 30.7(10) ?
C4 C5 C13 C12 . . . . -154.5(8) ?
O2 C6 C7 C8 . . . . 176.3(8) ?
O2 C6 C11 C10 . . . . -176.4(9) ?
O2 C6 C11 C12 . . . . 1.0(13) ?
C7 C6 C11 C10 . . . . -1.8(14) ?
C7 C6 C11 C12 . . . . 175.6(8) ?
C11 C6 C7 C8 . . . . 1.6(14) ?
C6 C7 C8 C9 . . . . 0.1(12) ?
C7 C8 C9 Br1 . . . . -178.5(7) ?
C7 C8 C9 C10 . . . . -1.6(15) ?
Br1 C9 C10 C11 . . . . 178.2(7) ?
C8 C9 C10 C11 . . . . 1.4(15) ?
C9 C10 C11 C6 . . . . 0.3(11) ?
C9 C10 C11 C12 . . . . -176.9(9) ?
C6 C11 C12 C13 . . . . 11.1(13) ?
C10 C11 C12 C13 . . . . -171.7(9) ?
C11 C12 C13 C1 . . . . -179.0(8) ?
C11 C12 C13 C5 . . . . 6.3(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742999
