#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/54/2235419.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_2235419
loop_
_publ_author_name
'Solanko, Katarzyna A.'
'Bond, Andrew D.'
_publ_section_title
;
 2-[(2-Acetoxybenzoyl)oxy]benzoic acid
;
_journal_coeditor_code           FY2058
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2108
_journal_paper_doi               10.1107/S1600536812026475
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H12 O6'
_chemical_formula_moiety         'C16 H12 O6'
_chemical_formula_sum            'C16 H12 O6'
_chemical_formula_weight         300.26
_chemical_name_common            'Acetylsalicylsalicylic acid'
_chemical_name_systematic
;
2-[(2-Acetoxybenzoyl)oxy]benzoic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 95.572(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6314(5)
_cell_length_b                   7.7548(3)
_cell_length_c                   18.0763(8)
_cell_measurement_reflns_used    5582
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.86
_cell_volume                     1343.73(11)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker Nonius X8 APEXII CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15807
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         3.63
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2367
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0328
_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)+(0.0341P)²+0.4730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0804
_reflns_number_gt                1868
_reflns_number_total             2367
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fy2058.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235419
_cod_database_fobs_code          2235419
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_symmetry_multiplicity
O O1 0.25601(10) 0.66416(13) 0.32136(5) 0.0262(3) Uani d . 1 1
O O2 0.38752(12) 0.75630(15) 0.42277(7) 0.0369(3) Uani d . 1 1
O O3 0.62427(10) 0.57401(13) 0.46447(5) 0.0245(3) Uani d . 1 1
O O4 0.69302(12) 0.76366(15) 0.38150(6) 0.0367(3) Uani d . 1 1
O O5 0.07707(13) 0.52229(15) 0.41146(6) 0.0373(3) Uani d D 1 1
H H5 0.052(3) 0.451(3) 0.4443(11) 0.082(8) Uiso d D 1 1
O O6 0.00116(13) 0.70903(14) 0.49167(6) 0.0351(3) Uani d . 1 1
C C1 0.45005(15) 0.49405(19) 0.36384(8) 0.0212(3) Uani d . 1 1
C C2 0.40413(16) 0.3714(2) 0.31037(8) 0.0249(4) Uani d . 1 1
H H2A 0.3206 0.3914 0.2791 0.030 Uiso calc R 1 1
C C3 0.47842(16) 0.2217(2) 0.30243(9) 0.0281(4) Uani d . 1 1
H H3A 0.4461 0.1398 0.2656 0.034 Uiso calc R 1 1
C C4 0.59942(17) 0.1906(2) 0.34767(9) 0.0296(4) Uani d . 1 1
H H4A 0.6494 0.0863 0.3426 0.036 Uiso calc R 1 1
C C5 0.64823(16) 0.3111(2) 0.40048(8) 0.0263(4) Uani d . 1 1
H H5A 0.7320 0.2903 0.4314 0.032 Uiso calc R 1 1
C C6 0.57436(15) 0.46175(19) 0.40792(8) 0.0213(3) Uani d . 1 1
C C7 0.36674(15) 0.6510(2) 0.37434(8) 0.0232(4) Uani d . 1 1
C C8 0.67024(15) 0.7322(2) 0.44426(9) 0.0266(4) Uani d . 1 1
C C9 0.68674(17) 0.8504(2) 0.50933(9) 0.0331(4) Uani d . 1 1
H H9A 0.7316 0.9574 0.4953 0.050 Uiso calc R 1 1
H H9B 0.7447 0.7949 0.5501 0.050 Uiso calc R 1 1
H H9C 0.5948 0.8768 0.5254 0.050 Uiso calc R 1 1
C C10 0.17065(15) 0.8088(2) 0.32687(8) 0.0236(4) Uani d . 1 1
C C11 0.18395(16) 0.9407(2) 0.27723(9) 0.0283(4) Uani d . 1 1
H H11A 0.2497 0.9319 0.2415 0.034 Uiso calc R 1 1
C C12 0.10136(16) 1.0862(2) 0.27940(9) 0.0305(4) Uani d . 1 1
H H12A 0.1091 1.1765 0.2445 0.037 Uiso calc R 1 1
C C13 0.00762(16) 1.1002(2) 0.33224(9) 0.0303(4) Uani d . 1 1
H H13A -0.0480 1.2009 0.3343 0.036 Uiso calc R 1 1
C C14 -0.00502(16) 0.9675(2) 0.38195(9) 0.0273(4) Uani d . 1 1
H H14A -0.0691 0.9784 0.4185 0.033 Uiso calc R 1 1
C C15 0.07431(15) 0.81807(19) 0.37966(8) 0.0234(3) Uani d . 1 1
C C16 0.04899(16) 0.6788(2) 0.43270(9) 0.0258(4) 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'
O O 0.0106 0.0060 '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
C7 O1 C10 115.71(11)
C8 O3 C6 117.58(11)
C16 O5 H5 108.2(16)
C6 C1 C2 117.99(14)
C6 C1 C7 121.35(13)
C2 C1 C7 120.63(14)
C3 C2 C1 120.84(15)
C3 C2 H2A 119.6
C1 C2 H2A 119.6
C2 C3 C4 120.23(15)
C2 C3 H3A 119.9
C4 C3 H3A 119.9
C3 C4 C5 120.08(14)
C3 C4 H4A 120.0
C5 C4 H4A 120.0
C6 C5 C4 119.63(15)
C6 C5 H5A 120.2
C4 C5 H5A 120.2
C5 C6 O3 117.13(13)
C5 C6 C1 121.20(14)
O3 C6 C1 121.54(13)
O2 C7 O1 121.63(14)
O2 C7 C1 126.80(14)
O1 C7 C1 111.55(12)
O4 C8 O3 121.91(14)
O4 C8 C9 127.32(15)
O3 C8 C9 110.77(13)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 C15 121.20(14)
C11 C10 O1 117.20(13)
C15 C10 O1 121.59(14)
C10 C11 C12 119.87(14)
C10 C11 H11A 120.1
C12 C11 H11A 120.1
C13 C12 C11 120.00(15)
C13 C12 H12A 120.0
C11 C12 H12A 120.0
C14 C13 C12 119.82(15)
C14 C13 H13A 120.1
C12 C13 H13A 120.1
C13 C14 C15 121.24(14)
C13 C14 H14A 119.4
C15 C14 H14A 119.4
C14 C15 C10 117.83(14)
C14 C15 C16 117.59(13)
C10 C15 C16 124.57(14)
O6 C16 O5 122.61(14)
O6 C16 C15 121.59(14)
O5 C16 C15 115.77(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.3662(18)
O1 C10 1.3998(18)
O2 C7 1.1995(18)
O3 C8 1.3659(19)
O3 C6 1.3923(18)
O4 C8 1.2013(18)
O5 C16 1.3090(19)
O5 H5 0.860(10)
O6 C16 1.2242(18)
C1 C6 1.395(2)
C1 C2 1.397(2)
C1 C7 1.480(2)
C2 C3 1.378(2)
C2 H2A 0.950
C3 C4 1.378(2)
C3 H3A 0.950
C4 C5 1.385(2)
C4 H4A 0.950
C5 C6 1.381(2)
C5 H5A 0.950
C8 C9 1.488(2)
C9 H9A 0.980
C9 H9B 0.980
C9 H9C 0.980
C10 C11 1.375(2)
C10 C15 1.396(2)
C11 C12 1.383(2)
C11 H11A 0.950
C12 C13 1.381(2)
C12 H12A 0.950
C13 C14 1.379(2)
C13 H13A 0.950
C14 C15 1.391(2)
C14 H14A 0.950
C15 C16 1.480(2)
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
O5 H5 O6 3_566 0.860(10) 1.810(10) 2.6660(16) 176(2)
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
C6 C1 C2 C3 1.1(2)
C7 C1 C2 C3 -177.36(13)
C1 C2 C3 C4 0.3(2)
C2 C3 C4 C5 -1.2(2)
C3 C4 C5 C6 0.6(2)
C4 C5 C6 O3 176.69(13)
C4 C5 C6 C1 0.9(2)
C8 O3 C6 C5 115.45(14)
C8 O3 C6 C1 -68.76(17)
C2 C1 C6 C5 -1.7(2)
C7 C1 C6 C5 176.74(13)
C2 C1 C6 O3 -177.31(12)
C7 C1 C6 O3 1.1(2)
C10 O1 C7 O2 0.9(2)
C10 O1 C7 C1 179.84(11)
C6 C1 C7 O2 -6.4(2)
C2 C1 C7 O2 172.01(15)
C6 C1 C7 O1 174.74(12)
C2 C1 C7 O1 -6.87(18)
C6 O3 C8 O4 -14.2(2)
C6 O3 C8 C9 166.09(12)
C7 O1 C10 C11 104.36(15)
C7 O1 C10 C15 -76.66(17)
C15 C10 C11 C12 0.3(2)
O1 C10 C11 C12 179.32(13)
C10 C11 C12 C13 1.2(2)
C11 C12 C13 C14 -1.1(2)
C12 C13 C14 C15 -0.6(2)
C13 C14 C15 C10 2.0(2)
C13 C14 C15 C16 -177.04(14)
C11 C10 C15 C14 -1.9(2)
O1 C10 C15 C14 179.14(13)
C11 C10 C15 C16 177.09(14)
O1 C10 C15 C16 -1.8(2)
C14 C15 C16 O6 -25.3(2)
C10 C15 C16 O6 155.67(15)
C14 C15 C16 O5 152.75(14)
C10 C15 C16 O5 -26.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10292
