#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/71/2237129.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_2237129
loop_
_publ_author_name
'Slater, Kara A.'
'Andersh, Brad'
'Flint, Edward B.'
'Ferrence, Gregory M.'
_publ_section_title
;
 6-Phenyloxane-2,4-dione
;
_journal_coeditor_code           BX2433
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o69
_journal_paper_doi               10.1107/S1600536812049781
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C11 H10 O3'
_chemical_formula_moiety         'C11 H10 O3'
_chemical_formula_sum            'C11 H10 O3'
_chemical_formula_weight         190.19
_chemical_name_systematic
;
6-Phenyloxane-2,4-dione
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.9888(6)
_cell_length_b                   5.4501(2)
_cell_length_c                   19.7350(8)
_cell_measurement_reflns_used    2535
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.482
_cell_measurement_theta_min      2.387
_cell_volume                     1827.28(12)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury
(Macrae et al., 2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), PLATON (Spek, 2009)
and publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution
'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17960
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.247
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0390P)²+1.8272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1136
_reflns_number_gt                1322
_reflns_number_total             1804
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2433.cif
_cod_data_source_block           I
_cod_database_code               2237129
_cod_database_fobs_code          2237129
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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
C C1 0.15992(11) 0.2655(4) 0.22819(11) 0.0198(5) Uani d . 1
C C2 0.13487(12) 0.0646(4) 0.27556(11) 0.0208(5) Uani d . 1
H H2A 0.1203 0.1376 0.3198 0.025 Uiso calc R 1
H H2B 0.1799 -0.0474 0.2833 0.025 Uiso calc R 1
C C3 0.06630(12) -0.0808(4) 0.24883(12) 0.0200(5) Uani d . 1
C C4 0.06699(12) -0.1241(4) 0.17377(11) 0.0203(5) Uani d . 1
H H4A 0.0222 -0.0357 0.1529 0.024 Uiso calc R 1
H H4B 0.0598 -0.3015 0.1649 0.024 Uiso calc R 1
C C5 0.14301(12) -0.0391(4) 0.14093(11) 0.0197(5) Uani d . 1
H H5 0.1869 -0.1489 0.1557 0.024 Uiso calc R 1
C C6 0.13875(12) -0.0384(4) 0.06490(11) 0.0196(5) Uani d . 1
C C7 0.17318(12) -0.2284(4) 0.02863(12) 0.0240(5) Uani d . 1
H H7 0.2002 -0.3554 0.052 0.029 Uiso calc R 1
C C8 0.16830(13) -0.2336(4) -0.04141(12) 0.0289(6) Uani d . 1
H H8 0.1921 -0.364 -0.0659 0.035 Uiso calc R 1
C C9 0.12897(13) -0.0501(4) -0.07580(12) 0.0283(5) Uani d . 1
H H9 0.1257 -0.0542 -0.1238 0.034 Uiso calc R 1
C C10 0.09416(13) 0.1406(4) -0.03986(12) 0.0284(6) Uani d . 1
H H10 0.0672 0.2673 -0.0634 0.034 Uiso calc R 1
C C11 0.09869(12) 0.1464(4) 0.03021(11) 0.0242(5) Uani d . 1
H H11 0.0745 0.2763 0.0546 0.029 Uiso calc R 1
O O1 0.17979(9) 0.4702(3) 0.24675(8) 0.0240(4) Uani d . 1
O O2 0.01417(8) -0.1540(3) 0.28609(8) 0.0237(4) Uani d . 1
O O3 0.16073(8) 0.2144(3) 0.16170(7) 0.0211(4) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
O1 C1 O3 118.69(19)
O1 C1 C2 123.9(2)
O3 C1 C2 117.43(18)
C1 C2 C3 112.66(18)
C1 C2 H2A 109.1
C3 C2 H2A 109.1
C1 C2 H2B 109.1
C3 C2 H2B 109.1
H2A C2 H2B 107.8
O2 C3 C4 123.38(19)
O2 C3 C2 121.6(2)
C4 C3 C2 115.03(18)
C3 C4 C5 112.35(17)
C3 C4 H4A 109.1
C5 C4 H4A 109.1
C3 C4 H4B 109.1
C5 C4 H4B 109.1
H4A C4 H4B 107.9
O3 C5 C6 106.59(17)
O3 C5 C4 109.98(16)
C6 C5 C4 112.73(17)
O3 C5 H5 109.2
C6 C5 H5 109.2
C4 C5 H5 109.2
C7 C6 C11 119.4(2)
C7 C6 C5 119.53(19)
C11 C6 C5 121.03(19)
C8 C7 C6 120.3(2)
C8 C7 H7 119.8
C6 C7 H7 119.8
C9 C8 C7 120.3(2)
C9 C8 H8 119.9
C7 C8 H8 119.9
C8 C9 C10 119.8(2)
C8 C9 H9 120.1
C10 C9 H9 120.1
C11 C10 C9 120.2(2)
C11 C10 H10 119.9
C9 C10 H10 119.9
C10 C11 C6 120.0(2)
C10 C11 H11 120
C6 C11 H11 120
C1 O3 C5 117.72(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.222(3)
C1 O3 1.342(2)
C1 C2 1.501(3)
C2 C3 1.505(3)
C2 H2A 0.99
C2 H2B 0.99
C3 O2 1.218(2)
C3 C4 1.500(3)
C4 C5 1.517(3)
C4 H4A 0.99
C4 H4B 0.99
C5 O3 1.472(2)
C5 C6 1.502(3)
C5 H5 1
C6 C7 1.388(3)
C6 C11 1.395(3)
C7 C8 1.385(3)
C7 H7 0.95
C8 C9 1.381(3)
C8 H8 0.95
C9 C10 1.391(3)
C9 H9 0.95
C10 C11 1.385(3)
C10 H10 0.95
C11 H11 0.95
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
O1 C1 C2 C3 139.8(2)
O3 C1 C2 C3 -40.6(3)
C1 C2 C3 O2 -141.94(19)
C1 C2 C3 C4 37.3(2)
O2 C3 C4 C5 -173.43(19)
C2 C3 C4 C5 7.4(2)
C3 C4 C5 O3 -50.7(2)
C3 C4 C5 C6 -169.46(17)
O3 C5 C6 C7 137.70(18)
C4 C5 C6 C7 -101.5(2)
O3 C5 C6 C11 -44.2(2)
C4 C5 C6 C11 76.5(2)
C11 C6 C7 C8 0.4(3)
C5 C6 C7 C8 178.5(2)
C6 C7 C8 C9 -0.1(3)
C7 C8 C9 C10 0.0(3)
C8 C9 C10 C11 -0.2(3)
C9 C10 C11 C6 0.5(3)
C7 C6 C11 C10 -0.6(3)
C5 C6 C11 C10 -178.68(19)
O1 C1 O3 C5 174.97(17)
C2 C1 O3 C5 -4.6(3)
C6 C5 O3 C1 173.64(17)
C4 C5 O3 C1 51.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 485681
