#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/78/2237827.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_2237827
loop_
_publ_author_name
'Wu, Chao'
'Guo, Yan-Jun'
'Xia, Ai-Bao'
_publ_section_title
;
 (4aR,9R,9aR)-7-Bromo-9-nitromethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthen-1-one
;
_journal_coeditor_code           FY2090
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o794
_journal_paper_doi               10.1107/S1600536813008659
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C14 H14 Br N O4'
_chemical_formula_moiety         'C14 H14 Br N O4'
_chemical_formula_sum            'C14 H14 Br N O4'
_chemical_formula_weight         340.17
_chemical_name_systematic
(4aR,9R,9aR)-7-Bromo-9-nitromethyl-2,3,4,4a,9,9a-hexahydro-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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.849(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.3457(7)
_cell_length_b                   5.4662(5)
_cell_length_c                   13.2446(12)
_cell_measurement_reflns_used    4391
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.2
_cell_volume                     730.25(11)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 2006)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 2006)'
_computing_data_reduction        'CrystalStructure (Rigaku, 2007)'
_computing_molecular_graphics    'ORTEP-3 for windows (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0900
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6335
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    2.826
_exptl_absorpt_correction_T_max  0.6732
_exptl_absorpt_correction_T_min  0.2236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.458
_refine_ls_abs_structure_details 'Flack (1983), 1058 Friedel pairs'
_refine_ls_abs_structure_Flack   0.021(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0525P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1367
_reflns_number_gt                1537
_reflns_number_total             2655
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fy2090.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2237827
_cod_database_fobs_code          2237827
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_symmetry_multiplicity
C C1 0.1121(7) 0.9599(12) 0.3568(5) 0.0740(18) Uani d . 1 1
C C2 0.2242(7) 0.9776(13) 0.4388(6) 0.084(2) Uani d . 1 1
H H2 0.2201 1.0658 0.4980 0.101 Uiso calc R 1 1
C C3 0.3408(7) 0.8631(13) 0.4308(5) 0.079(2) Uani d . 1 1
H H3 0.4154 0.8757 0.4847 0.095 Uiso calc R 1 1
C C4 0.3469(5) 0.7291(10) 0.3426(5) 0.0575(14) Uani d . 1 1
C C5 0.4665(5) 0.4397(10) 0.2629(5) 0.0594(15) Uani d . 1 1
H H5 0.4212 0.2917 0.2785 0.071 Uiso calc R 1 1
C C6 0.6112(5) 0.3829(12) 0.2656(6) 0.074(2) Uani d . 1 1
H H6A 0.6535 0.3222 0.3337 0.089 Uiso calc R 1 1
H H6B 0.6160 0.2555 0.2156 0.089 Uiso calc R 1 1
C C7 0.6840(5) 0.6043(15) 0.2415(5) 0.0816(19) Uani d . 1 1
H H7A 0.7741 0.5588 0.2397 0.098 Uiso calc R 1 1
H H7B 0.6882 0.7244 0.2960 0.098 Uiso calc R 1 1
C C8 0.6170(5) 0.7183(13) 0.1378(6) 0.077(2) Uani d . 1 1
H H8A 0.6599 0.8722 0.1292 0.092 Uiso calc R 1 1
H H8B 0.6273 0.6101 0.0820 0.092 Uiso calc R 1 1
C C9 0.4716(5) 0.7627(10) 0.1311(4) 0.0553(14) Uani d . 1 1
C C10 0.3944(4) 0.5445(8) 0.1576(4) 0.0461(12) Uani d . 1 1
H H10 0.3945 0.4183 0.1050 0.055 Uiso calc R 1 1
C C11 0.2504(4) 0.6049(10) 0.1573(4) 0.0487(12) Uani d . 1 1
H H11 0.2196 0.7266 0.1029 0.058 Uiso calc R 1 1
C C12 0.2391(5) 0.7152(9) 0.2586(5) 0.0518(14) Uani d . 1 1
C C13 0.1217(6) 0.8341(11) 0.2703(5) 0.0650(16) Uani d . 1 1
H H13 0.0473 0.8255 0.2160 0.078 Uiso calc R 1 1
C C14 0.1623(5) 0.3767(10) 0.1314(5) 0.0572(15) Uani d . 1 1
H H14A 0.2038 0.2403 0.1732 0.069 Uiso calc R 1 1
H H14B 0.0773 0.4073 0.1485 0.069 Uiso calc R 1 1
N N1 0.1410(4) 0.3111(10) 0.0188(5) 0.0621(14) Uani d . 1 1
O O1 0.4667(3) 0.6210(10) 0.3413(3) 0.0647(10) Uani d . 1 1
O O2 0.4213(4) 0.9576(7) 0.1075(4) 0.0745(13) Uani d . 1 1
O O3 0.1104(4) 0.0988(9) -0.0041(4) 0.1026(17) Uani d . 1 1
O O4 0.1497(5) 0.4689(10) -0.0439(4) 0.0874(14) Uani d . 1 1
Br Br1 -0.04348(7) 1.1196(2) 0.36550(7) 0.1208(5) Uani d . 1 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'
N N 0.0061 0.0033 '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
C13 C1 C2 119.0(6)
C13 C1 Br1 121.1(5)
C2 C1 Br1 119.8(5)
C3 C2 C1 119.6(6)
C3 C2 H2 120.2
C1 C2 H2 120.2
C2 C3 C4 120.3(6)
C2 C3 H3 119.8
C4 C3 H3 119.8
O1 C4 C3 116.4(5)
O1 C4 C12 122.0(5)
C3 C4 C12 121.5(5)
O1 C5 C6 106.3(5)
O1 C5 C10 108.8(4)
C6 C5 C10 111.9(5)
O1 C5 H5 109.9
C6 C5 H5 109.9
C10 C5 H5 109.9
C7 C6 C5 111.7(5)
C7 C6 H6A 109.3
C5 C6 H6A 109.3
C7 C6 H6B 109.3
C5 C6 H6B 109.3
H6A C6 H6B 107.9
C6 C7 C8 111.8(5)
C6 C7 H7A 109.2
C8 C7 H7A 109.2
C6 C7 H7B 109.2
C8 C7 H7B 109.2
H7A C7 H7B 107.9
C9 C8 C7 111.5(6)
C9 C8 H8A 109.3
C7 C8 H8A 109.3
C9 C8 H8B 109.3
C7 C8 H8B 109.3
H8A C8 H8B 108.0
O2 C9 C8 122.0(5)
O2 C9 C10 122.6(5)
C8 C9 C10 115.4(5)
C9 C10 C11 113.1(4)
C9 C10 C5 109.1(4)
C11 C10 C5 111.1(4)
C9 C10 H10 107.8
C11 C10 H10 107.8
C5 C10 H10 107.8
C12 C11 C10 110.8(4)
C12 C11 C14 111.4(4)
C10 C11 C14 110.8(4)
C12 C11 H11 107.9
C10 C11 H11 107.9
C14 C11 H11 107.9
C4 C12 C13 116.2(5)
C4 C12 C11 122.0(5)
C13 C12 C11 121.5(5)
C1 C13 C12 123.3(6)
C1 C13 H13 118.3
C12 C13 H13 118.3
N1 C14 C11 111.3(5)
N1 C14 H14A 109.4
C11 C14 H14A 109.4
N1 C14 H14B 109.4
C11 C14 H14B 109.4
H14A C14 H14B 108.0
O4 N1 O3 124.0(6)
O4 N1 C14 119.5(5)
O3 N1 C14 116.4(6)
C4 O1 C5 116.7(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C13 1.359(9)
C1 C2 1.405(9)
C1 Br1 1.857(6)
C2 C3 1.383(8)
C2 H2 0.9300
C3 C4 1.393(8)
C3 H3 0.9300
C4 O1 1.376(6)
C4 C12 1.391(7)
C5 O1 1.435(8)
C5 C6 1.521(7)
C5 C10 1.538(8)
C5 H5 0.9800
C6 C7 1.497(10)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C8 1.527(9)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.506(8)
C8 H8A 0.9700
C8 H8B 0.9700
C9 O2 1.196(6)
C9 C10 1.519(7)
C10 C11 1.525(6)
C10 H10 0.9800
C11 C12 1.499(7)
C11 C14 1.538(7)
C11 H11 0.9800
C12 C13 1.417(7)
C13 H13 0.9300
C14 N1 1.502(8)
C14 H14A 0.9700
C14 H14B 0.9700
N1 O4 1.214(6)
N1 O3 1.223(7)
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 O1 2_656 0.930 2.710 3.520(9) 146
C8 H8B O2 2_645 0.971 2.586 3.489(6) 155
C8 H8A O4 2_655 0.970 2.535 3.253(4) 131
C10 H10 O2 1_545 0.981 2.533 3.300(8) 135
C11 H11 O3 1_565 0.980 2.591 3.547(8) 165
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
C13 C1 C2 C3 -1.3(11)
Br1 C1 C2 C3 -178.5(6)
C1 C2 C3 C4 -0.6(11)
C2 C3 C4 O1 -179.9(6)
C2 C3 C4 C12 2.9(11)
O1 C5 C6 C7 -61.4(7)
C10 C5 C6 C7 57.2(7)
C5 C6 C7 C8 -55.4(7)
C6 C7 C8 C9 51.6(7)
C7 C8 C9 O2 128.3(7)
C7 C8 C9 C10 -51.1(7)
O2 C9 C10 C11 -3.6(8)
C8 C9 C10 C11 175.8(5)
O2 C9 C10 C5 -127.8(6)
C8 C9 C10 C5 51.6(6)
O1 C5 C10 C9 63.7(5)
C6 C5 C10 C9 -53.5(6)
O1 C5 C10 C11 -61.7(5)
C6 C5 C10 C11 -178.9(5)
C9 C10 C11 C12 -83.4(6)
C5 C10 C11 C12 39.7(6)
C9 C10 C11 C14 152.4(5)
C5 C10 C11 C14 -84.5(5)
O1 C4 C12 C13 179.8(5)
C3 C4 C12 C13 -3.2(9)
O1 C4 C12 C11 -6.6(8)
C3 C4 C12 C11 170.4(6)
C10 C11 C12 C4 -6.8(7)
C14 C11 C12 C4 117.0(5)
C10 C11 C12 C13 166.4(4)
C14 C11 C12 C13 -69.8(6)
C2 C1 C13 C12 1.0(10)
Br1 C1 C13 C12 178.1(4)
C4 C12 C13 C1 1.2(9)
C11 C12 C13 C1 -172.4(6)
C12 C11 C14 N1 162.8(4)
C10 C11 C14 N1 -73.3(5)
C11 C14 N1 O4 -25.2(6)
C11 C14 N1 O3 157.5(4)
C3 C4 O1 C5 166.4(6)
C12 C4 O1 C5 -16.5(8)
C6 C5 O1 C4 170.2(5)
C10 C5 O1 C4 49.5(7)
