##############################################################################
#                                                                            #
# 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_global
_audit_creation_method     ?
_journal_date_recd_electronic     2014-10-04
_journal_date_accepted     2014-10-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue     11
_journal_page_first     o1153
_journal_page_last     o1153
_journal_paper_category     HO
_journal_paper_doi     10.1107/S1600536814021904
_journal_coeditor_code     HB7293
_publ_contact_author
;
Muhammad Nawaz Tahir
University of Sargodha
Department of Physics
Sargodha
Pakistan
;
_publ_contact_author_email     'dmntahir_uos@yahoo.com'
_publ_contact_author_fax     '0092 48 32 22 121'
_publ_contact_author_phone     '0092 48 92 30 914'
_publ_section_title
;
Crystal structure of 3-[(2-acetylphenoxy)carbonyl]benzoic acid
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Shoaib, Mohammad' .
;
Department of Pharmacy
University of Malakand
Khyber Pakhtunkhwa
Pakistan
;
    'Shah, Ismail' .
;
Department of Pharmacy
University of Malakand
Khyber Pakhtunkhwa
Pakistan
;
    'Shah, Syed Wadood Ali' .
;
Department of Pharmacy
University of Malakand
Khyber Pakhtunkhwa
Pakistan
;
    'Tahir, Muhammad Nawaz' .
;
Department of Physics
University of Sargodha
Sargodha
Punjab
Pakistan
;
    'Ullah, Shafi' .
;
Department of Pharmacy
University of Malakand
Khyber Pakhtunkhwa
Pakistan
;
    'Ayaz, Muhammad' .
;
Department of Pharmacy
University of Malakand
Khyber Pakhtunkhwa
Pakistan
;
data_I
_database_code_depnum_ccdc_archive 'CCDC 1027627'
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-[(2-Acetylphenoxy)carbonyl]benzoic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H12 O5'
_chemical_formula_sum     'C16 H12 O5'
_chemical_formula_iupac     'C16 H12 O5'
_chemical_formula_weight     284.26
_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     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     13.5081(10)
_cell_length_b     7.4743(6)
_cell_length_c     13.9421(11)
_cell_angle_alpha     90
_cell_angle_beta     106.671(3)
_cell_angle_gamma     90
_cell_volume     1348.48(18)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1971
_cell_measurement_theta_min     1.851
_cell_measurement_theta_max     26.0
_cell_measurement_temperature     296(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     'light yellow'
_exptl_crystal_size_max     0.38
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.400
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     592
_exptl_absorpt_coefficient_mu     0.105
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2005)
;
_exptl_absorpt_correction_T_min     0.963
_exptl_absorpt_correction_T_max     0.977
_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 Kappa APEXII CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     7.50
_diffrn_reflns_number     10280
_diffrn_reflns_av_R_equivalents     0.0221
_diffrn_reflns_theta_min     1.851
_diffrn_reflns_theta_max     26.000
_diffrn_reflns_theta_full     26.000
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_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     2655
_reflns_number_gt     1971
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0578
_refine_ls_R_factor_gt     0.0409
_refine_ls_wR_factor_gt     0.1024
_refine_ls_wR_factor_ref     0.1151
_refine_ls_goodness_of_fit_ref     1.027
_refine_ls_restrained_S_all     1.027
_refine_ls_number_reflns     2655
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0505P)²+0.4011P] 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     0.180
_refine_diff_density_min     -0.202
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, 2007)
;
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;
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 0.36130(10) 0.0311(2) 0.47366(9) 0.0704(5) Uani d 1 . .
    H H1 0.4166 0.0276 0.5177 0.106 Uiso calc 1 . .
    O O2 0.46474(9) -0.0058(2) 0.37694(9) 0.0627(4) Uani d 1 . .
    O O3 0.14695(9) -0.0066(2) -0.05814(9) 0.0669(4) Uani d 1 . .
    O O4 0.31564(8) -0.05274(16) 0.01634(7) 0.0411(3) Uani d 1 . .
    O O5 0.48190(13) 0.2965(2) -0.11562(12) 0.0767(5) Uani d 1 . .
    C C1 0.37753(13) 0.0154(2) 0.38694(11) 0.0435(4) Uani d 1 . .
    C C2 0.28422(12) 0.0221(2) 0.29912(11) 0.0370(4) Uani d 1 . .
    C C3 0.18668(13) 0.0478(2) 0.31086(12) 0.0435(4) Uani d 1 . .
    H H3 0.1791 0.0628 0.3746 0.052 Uiso calc 1 . .
    C C4 0.10086(13) 0.0512(3) 0.22840(13) 0.0505(5) Uani d 1 . .
    H H4 0.0355 0.0673 0.2366 0.061 Uiso calc 1 . .
    C C5 0.11211(13) 0.0306(3) 0.13359(13) 0.0471(4) Uani d 1 . .
    H H5 0.0542 0.0336 0.0780 0.056 Uiso calc 1 . .
    C C6 0.20966(12) 0.0052(2) 0.12066(11) 0.0368(4) Uani d 1 . .
    C C7 0.29593(12) 0.0005(2) 0.20355(11) 0.0370(4) Uani d 1 . .
    H H7 0.3613 -0.0169 0.1955 0.044 Uiso calc 1 . .
    C C8 0.21703(12) -0.0183(2) 0.01684(12) 0.0404(4) Uani d 1 . .
    C C9 0.33430(12) -0.0900(2) -0.07617(11) 0.0381(4) Uani d 1 . .
    C C10 0.30562(14) -0.2564(3) -0.11818(13) 0.0485(4) Uani d 1 . .
    H H10 0.2692 -0.3350 -0.0892 0.058 Uiso calc 1 . .
    C C11 0.33147(15) -0.3054(3) -0.20375(13) 0.0560(5) Uani d 1 . .
    H H11 0.3132 -0.4178 -0.2319 0.067 Uiso calc 1 . .
    C C12 0.38433(14) -0.1876(3) -0.24715(13) 0.0552(5) Uani d 1 . .
    H H12 0.4012 -0.2199 -0.3049 0.066 Uiso calc 1 . .
    C C13 0.41194(13) -0.0225(3) -0.20493(12) 0.0476(5) Uani d 1 . .
    H H13 0.4474 0.0559 -0.2351 0.057 Uiso calc 1 . .
    C C14 0.38845(12) 0.0318(2) -0.11770(11) 0.0375(4) Uani d 1 . .
    C C15 0.42394(13) 0.2153(2) -0.07883(12) 0.0456(4) Uani d 1 . .
    C C16 0.38994(17) 0.3003(3) 0.00334(16) 0.0614(5) Uani d 1 . .
    H H16A 0.4174 0.4195 0.0148 0.092 Uiso calc 1 . .
    H H16B 0.4148 0.2311 0.0635 0.092 Uiso calc 1 . .
    H H16C 0.3158 0.3051 -0.0154 0.092 Uiso calc 1 . .
_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
    O1 C1 . 1.2946(19) ?
    O1 H1 . 0.8200 ?
    O2 C1 . 1.236(2) ?
    O3 C8 . 1.1953(19) ?
    O4 C8 . 1.3587(19) ?
    O4 C9 . 1.4111(17) ?
    O5 C15 . 1.215(2) ?
    C1 C2 . 1.485(2) ?
    C2 C3 . 1.387(2) ?
    C2 C7 . 1.395(2) ?
    C3 C4 . 1.379(2) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.382(2) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.393(2) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.386(2) ?
    C6 C8 . 1.489(2) ?
    C7 H7 . 0.9300 ?
    C9 C10 . 1.382(2) ?
    C9 C14 . 1.394(2) ?
    C10 C11 . 1.385(2) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.379(3) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.372(3) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.402(2) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.502(2) ?
    C15 C16 . 1.493(2) ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
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
    C1 O1 H1 . . 109.5 ?
    C8 O4 C9 . . 118.33(12) ?
    O2 C1 O1 . . 122.65(15) ?
    O2 C1 C2 . . 121.50(14) ?
    O1 C1 C2 . . 115.84(14) ?
    C3 C2 C7 . . 120.03(15) ?
    C3 C2 C1 . . 121.19(14) ?
    C7 C2 C1 . . 118.78(14) ?
    C4 C3 C2 . . 120.27(15) ?
    C4 C3 H3 . . 119.9 ?
    C2 C3 H3 . . 119.9 ?
    C3 C4 C5 . . 119.91(15) ?
    C3 C4 H4 . . 120.0 ?
    C5 C4 H4 . . 120.0 ?
    C4 C5 C6 . . 120.44(15) ?
    C4 C5 H5 . . 119.8 ?
    C6 C5 H5 . . 119.8 ?
    C7 C6 C5 . . 119.71(14) ?
    C7 C6 C8 . . 122.18(14) ?
    C5 C6 C8 . . 118.11(14) ?
    C6 C7 C2 . . 119.65(15) ?
    C6 C7 H7 . . 120.2 ?
    C2 C7 H7 . . 120.2 ?
    O3 C8 O4 . . 122.75(15) ?
    O3 C8 C6 . . 125.75(15) ?
    O4 C8 C6 . . 111.49(13) ?
    C10 C9 C14 . . 121.90(14) ?
    C10 C9 O4 . . 117.60(14) ?
    C14 C9 O4 . . 120.23(15) ?
    C9 C10 C11 . . 119.60(17) ?
    C9 C10 H10 . . 120.2 ?
    C11 C10 H10 . . 120.2 ?
    C12 C11 C10 . . 119.96(18) ?
    C12 C11 H11 . . 120.0 ?
    C10 C11 H11 . . 120.0 ?
    C13 C12 C11 . . 119.85(16) ?
    C13 C12 H12 . . 120.1 ?
    C11 C12 H12 . . 120.1 ?
    C12 C13 C14 . . 122.08(17) ?
    C12 C13 H13 . . 119.0 ?
    C14 C13 H13 . . 119.0 ?
    C9 C14 C13 . . 116.61(16) ?
    C9 C14 C15 . . 126.71(14) ?
    C13 C14 C15 . . 116.68(15) ?
    O5 C15 C16 . . 119.23(18) ?
    O5 C15 C14 . . 118.82(16) ?
    C16 C15 C14 . . 121.95(15) ?
    C15 C16 H16A . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
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
    O2 C1 C2 C3 . . . . -179.32(18) ?
    O1 C1 C2 C3 . . . . 1.4(3) ?
    O2 C1 C2 C7 . . . . 1.2(3) ?
    O1 C1 C2 C7 . . . . -178.08(17) ?
    C7 C2 C3 C4 . . . . 0.4(3) ?
    C1 C2 C3 C4 . . . . -179.14(17) ?
    C2 C3 C4 C5 . . . . -0.6(3) ?
    C3 C4 C5 C6 . . . . 0.4(3) ?
    C4 C5 C6 C7 . . . . 0.0(3) ?
    C4 C5 C6 C8 . . . . 179.31(17) ?
    C5 C6 C7 C2 . . . . -0.3(3) ?
    C8 C6 C7 C2 . . . . -179.53(15) ?
    C3 C2 C7 C6 . . . . 0.1(2) ?
    C1 C2 C7 C6 . . . . 179.60(15) ?
    C9 O4 C8 O3 . . . . -5.1(3) ?
    C9 O4 C8 C6 . . . . 175.91(14) ?
    C7 C6 C8 O3 . . . . -175.87(18) ?
    C5 C6 C8 O3 . . . . 4.9(3) ?
    C7 C6 C8 O4 . . . . 3.1(2) ?
    C5 C6 C8 O4 . . . . -176.17(15) ?
    C8 O4 C9 C10 . . . . -74.90(19) ?
    C8 O4 C9 C14 . . . . 110.95(17) ?
    C14 C9 C10 C11 . . . . 0.3(3) ?
    O4 C9 C10 C11 . . . . -173.72(15) ?
    C9 C10 C11 C12 . . . . -0.8(3) ?
    C10 C11 C12 C13 . . . . 0.5(3) ?
    C11 C12 C13 C14 . . . . 0.2(3) ?
    C10 C9 C14 C13 . . . . 0.4(2) ?
    O4 C9 C14 C13 . . . . 174.31(13) ?
    C10 C9 C14 C15 . . . . -179.79(16) ?
    O4 C9 C14 C15 . . . . -5.9(2) ?
    C12 C13 C14 C9 . . . . -0.7(2) ?
    C12 C13 C14 C15 . . . . 179.48(16) ?
    C9 C14 C15 O5 . . . . 170.50(17) ?
    C13 C14 C15 O5 . . . . -9.7(2) ?
    C9 C14 C15 C16 . . . . -9.6(3) ?
    C13 C14 C15 C16 . . . . 170.19(17) ?
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
    _geom_hbond_publ_flag
    O1 H1 O2 3_656 0.82 1.84 2.6623(18) 175 yes
    C4 H4 O5 4_566 0.93 2.58 3.257(3) 130 yes
_shelxl_version_number     2014/6
