##############################################################################
#                                                                            #
# 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-2014/7'
_chemical_name_systematic     ?
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H14 O6'
_chemical_formula_sum     'C20 H14 O6'
_chemical_formula_weight     350.31
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P n m a'
_space_group_name_Hall     '-P 2ac 2n'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z'
    'x+1/2, -y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z'
    '-x-1/2, y-1/2, z-1/2'
_cell_length_a     12.9597(12)
_cell_length_b     31.548(3)
_cell_length_c     3.8219(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1562.6(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6581
_cell_measurement_theta_min     2.58
_cell_measurement_theta_max     28.11
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.51
_exptl_crystal_size_mid     0.36
_exptl_crystal_size_min     0.29
_exptl_crystal_density_diffrn     1.489
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     728
_exptl_absorpt_coefficient_mu     0.111
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.6204
_exptl_absorpt_correction_T_max     0.7457
_exptl_special_details
;
One distinct cell was identified using APEX2 (Bruker, 2014).  Four
frame series were integrated and filtered for statistical outliers
using SAINT (Bruker, 2014) then corrected for absorption by integration
using SAINT/SADABS v2014/2 (Bruker, 2014) to sort, merge, and scale
the combined data.  No decay correction was applied.
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'microfocus sealed tube'
_diffrn_radiation_monochromator     'multilayer mirrors'
_diffrn_measurement_device     'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method     'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     16409
_diffrn_reflns_av_R_equivalents     0.0441
_diffrn_reflns_theta_min     2.582
_diffrn_reflns_theta_max     26.372
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -39
_diffrn_reflns_limit_k_max     39
_diffrn_reflns_limit_l_min     -4
_diffrn_reflns_limit_l_max     4
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Structure was phased by direct methods (Sheldrick, 2015).  Systematic
conditions suggested the ambiguous space group.  The space group choice
was confirmed by successful convergence of the full-matrix least-squares
refinement on F².  The final map had no other significant features.  A
final analysis of variance between observed and calculated structure
factors showed some dependence on amplitude and little dependence on
resolution.
;
_reflns_number_total     1625
_reflns_number_gt     1409
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0476
_refine_ls_R_factor_gt     0.0395
_refine_ls_wR_factor_gt     0.0891
_refine_ls_wR_factor_ref     0.0925
_refine_ls_goodness_of_fit_ref     1.164
_refine_ls_restrained_S_all     1.164
_refine_ls_number_reflns     1625
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0297P)²+1.0258P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.221
_refine_diff_density_min     -0.278
_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'
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014) and XPREP (Bruker, 2014)
;
_computing_structure_solution
;
SHELXT2014/4 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014/6 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
XCIF (Bruker, 2014) and publCIF (Westrip, 2010)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.53843(8) 0.37983(3) 0.6378(3) 0.0182(3) Uani d 1 . .
    O O2 0.64043(8) 0.32686(3) 0.6752(3) 0.0176(3) Uani d 1 . .
    O O3 0.49910(8) 0.32050(3) 0.3282(3) 0.0205(3) Uani d 1 . .
    C C1 0.45214(11) 0.40226(5) 0.5132(4) 0.0149(3) Uani d 1 . .
    C C2 0.47199(12) 0.44105(5) 0.3612(4) 0.0166(3) Uani d 1 . .
    H H2 0.5410 0.4506 0.3305 0.020 Uiso calc 1 . .
    C C3 0.38982(12) 0.46595(5) 0.2539(4) 0.0185(3) Uani d 1 . .
    H H3 0.4022 0.4928 0.1494 0.022 Uiso calc 1 . .
    C C4 0.28937(12) 0.45171(5) 0.2990(4) 0.0175(3) Uani d 1 . .
    H H4 0.2331 0.4687 0.2238 0.021 Uiso calc 1 . .
    C C5 0.27117(12) 0.41276(5) 0.4532(4) 0.0178(3) Uani d 1 . .
    H H5 0.2023 0.4031 0.4839 0.021 Uiso calc 1 . .
    C C6 0.35262(12) 0.38772(5) 0.5632(4) 0.0159(3) Uani d 1 . .
    H H6 0.3404 0.3611 0.6710 0.019 Uiso calc 1 . .
    C C7 0.55226(11) 0.33988(5) 0.5243(4) 0.0144(3) Uani d 1 . .
    C C8 0.68026(11) 0.28716(5) 0.5719(4) 0.0141(3) Uani d 1 . .
    C C9 0.63026(16) 0.2500 0.6630(6) 0.0146(4) Uani d 1 . .
    H H9 0.5657 0.2500 0.7808 0.018 Uiso calc 1 . .
    C C10 0.77487(11) 0.28802(5) 0.4077(4) 0.0152(3) Uani d 1 . .
    H H10 0.8068 0.3143 0.3513 0.018 Uiso calc 1 . .
    C C11 0.82269(16) 0.2500 0.3264(6) 0.0159(5) Uani d 1 . .
    H H11 0.8882 0.2500 0.2149 0.019 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    O1 C7 . 1.3446(18) ?
    O1 C1 . 1.4064(18) ?
    O2 C7 . 1.3442(18) ?
    O2 C8 . 1.4109(18) ?
    O3 C7 . 1.1878(18) ?
    C1 C2 . 1.379(2) ?
    C1 C6 . 1.382(2) ?
    C2 C3 . 1.385(2) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.388(2) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.383(2) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.384(2) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C8 C10 . 1.377(2) ?
    C8 C9 . 1.3842(19) ?
    C9 C8 7_565 1.3841(19) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.3856(18) ?
    C10 H10 . 0.9500 ?
    C11 C10 7_565 1.3856(18) ?
    C11 H11 . 0.9500 ?
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
    C7 O1 C1 . . 117.93(12) ?
    C7 O2 C8 . . 117.53(12) ?
    C2 C1 C6 . . 121.79(14) ?
    C2 C1 O1 . . 116.16(13) ?
    C6 C1 O1 . . 121.89(14) ?
    C1 C2 C3 . . 118.98(14) ?
    C1 C2 H2 . . 120.5 ?
    C3 C2 H2 . . 120.5 ?
    C2 C3 C4 . . 120.04(15) ?
    C2 C3 H3 . . 120.0 ?
    C4 C3 H3 . . 120.0 ?
    C5 C4 C3 . . 120.04(14) ?
    C5 C4 H4 . . 120.0 ?
    C3 C4 H4 . . 120.0 ?
    C4 C5 C6 . . 120.43(14) ?
    C4 C5 H5 . . 119.8 ?
    C6 C5 H5 . . 119.8 ?
    C1 C6 C5 . . 118.71(14) ?
    C1 C6 H6 . . 120.6 ?
    C5 C6 H6 . . 120.6 ?
    O3 C7 O2 . . 127.33(14) ?
    O3 C7 O1 . . 127.50(14) ?
    O2 C7 O1 . . 105.16(12) ?
    C10 C8 C9 . . 123.23(14) ?
    C10 C8 O2 . . 115.82(13) ?
    C9 C8 O2 . . 120.67(14) ?
    C8 C9 C8 7_565 . 115.8(2) ?
    C8 C9 H9 7_565 . 122.1 ?
    C8 C9 H9 . . 122.1 ?
    C8 C10 C11 . . 118.90(15) ?
    C8 C10 H10 . . 120.5 ?
    C11 C10 H10 . . 120.5 ?
    C10 C11 C10 . 7_565 119.9(2) ?
    C10 C11 H11 . . 120.0 ?
    C10 C11 H11 7_565 . 120.0 ?
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
    C7 O1 C1 C2 . . . . -125.86(15) ?
    C7 O1 C1 C6 . . . . 58.7(2) ?
    C6 C1 C2 C3 . . . . -0.4(2) ?
    O1 C1 C2 C3 . . . . -175.82(14) ?
    C1 C2 C3 C4 . . . . -0.2(2) ?
    C2 C3 C4 C5 . . . . 0.4(2) ?
    C3 C4 C5 C6 . . . . -0.1(2) ?
    C2 C1 C6 C5 . . . . 0.8(2) ?
    O1 C1 C6 C5 . . . . 175.92(14) ?
    C4 C5 C6 C1 . . . . -0.5(2) ?
    C8 O2 C7 O3 . . . . 5.6(2) ?
    C8 O2 C7 O1 . . . . -173.24(12) ?
    C1 O1 C7 O3 . . . . -0.4(2) ?
    C1 O1 C7 O2 . . . . 178.35(12) ?
    C7 O2 C8 C10 . . . . 116.32(15) ?
    C7 O2 C8 C9 . . . . -69.5(2) ?
    C10 C8 C9 C8 . . . 7_565 -1.4(3) ?
    O2 C8 C9 C8 . . . 7_565 -175.11(11) ?
    C9 C8 C10 C11 . . . . 0.5(3) ?
    O2 C8 C10 C11 . . . . 174.47(15) ?
    C8 C10 C11 C10 . . . 7_565 0.5(3) ?
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
    C10 H10 O3 6_656 0.95 2.592 3.2105(8) 123
data_global
_journal_date_recd_electronic     2017-11-10
_journal_date_accepted     2017-11-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2017
_journal_volume     73
_journal_issue     12
_journal_page_first     1942
_journal_page_last     1945
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989017016772
_journal_coeditor_code     SU5407
_publ_contact_author_name     'Jennifer A. Swift'
_publ_contact_author_address
;
Department of Chemistry,
Georgetown University,
37th and O Sts NW,
Washington, DC, 20057
USA
;
_publ_contact_author_email     jas2@georgetown.edu
_publ_contact_author_fax     '+ 202 687 5567'
_publ_contact_author_phone     '+ 202 687 6209'
_publ_section_title
;
Crystal structure of a diaryl carbonate: 1,3-phenylene bis(phenyl carbonate)
;
loop_
    _publ_author_name
    _publ_author_address
    'Marina A. Solomos'
;
Department of Chemistry,
Georgetown University,
37th and O Sts NW,
Washington, DC, 20057
USA
;
    'Jeffery A. Bertke'
;
Department of Chemistry,
Georgetown University,
37th and O Sts NW,
Washington, DC, 20057
USA
;
    'Jennifer A. Swift'
;
Department of Chemistry,
Georgetown University,
37th and O Sts NW,
Washington, DC, 20057
USA
;
_publ_section_synopsis
;
The whole molecule of the title diaryl carbonate is generated by mirror
symmetry, the mirror bisecting the central benzene ring, and the carbonate
groups adopt an s-cis-s-cis conformation. In the crystal, there are
only weak C---H...O hydrogen bonds and offset π--π interactions present.
;
