#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/87/2218716.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_2218716
loop_
_publ_author_name
'Muhammad, Khushi'
'Khawar Rauf, M.'
'Ebihara, Masahiro'
'Hameed, Shahid'
_publ_section_title
;
 4-(4-Propoxybenzoyloxy)benzoic acid
;
_journal_coeditor_code           HG2407
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1251
_journal_paper_doi               10.1107/S1600536808016942
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C17 H16 O5'
_chemical_formula_moiety         'C17 H16 O5'
_chemical_formula_sum            'C17 H16 O5'
_chemical_formula_weight         300.30
_chemical_name_common            '4-(4-Propoxybenzoyloxy)benzoic acid '
_chemical_name_systematic
;
4-(4-Propoxybenzoyloxy)benzoic acid
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 99.790(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.063(15)
_cell_length_b                   5.703(4)
_cell_length_c                   24.437(18)
_cell_measurement_reflns_used    3169
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.4
_cell_volume                     2893(4)
_computing_cell_refinement
'CrystalClear (Molecular Structure Corporation & Rigaku, 2001)'
_computing_data_collection
'CrystalClear (Molecular Structure Corporation & Rigaku, 2001)'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation & Rigaku, 2004)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and
TEXSAN (Molecular Structure Corporation & Rigaku, 2004)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            11426
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.38
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_correction_T_min  0.9701
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(NUMABS; Higashi, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.261
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.261
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0844
_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)+(0.026P)²+6.5341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1463
_reflns_number_gt                2824
_reflns_number_total             3297
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2407.cif
_cod_data_source_block           I
_cod_original_cell_volume        2893(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2218716
_cod_database_fobs_code          2218716
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.12026(11) 0.2626(4) 0.39828(9) 0.0171(5) Uani d . 1
C C2 0.15716(12) 0.4515(4) 0.42065(10) 0.0223(5) Uani d . 1
H H2 0.1686 0.5699 0.3968 0.027 Uiso calc R 1
C C3 0.17771(13) 0.4698(4) 0.47766(10) 0.0229(5) Uani d . 1
H H3 0.2030 0.6000 0.4926 0.027 Uiso calc R 1
C C4 0.16099(12) 0.2958(4) 0.51274(10) 0.0198(5) Uani d . 1
C C5 0.12360(12) 0.1058(4) 0.49037(10) 0.0229(5) Uani d . 1
H H5 0.1120 -0.0124 0.5142 0.027 Uiso calc R 1
C C6 0.10351(12) 0.0891(4) 0.43378(10) 0.0212(5) Uani d . 1
H H6 0.0781 -0.0408 0.4188 0.025 Uiso calc R 1
C C7 0.09682(11) 0.2342(4) 0.33803(10) 0.0176(5) Uani d . 1
O O1 0.06221(9) 0.0793(3) 0.31697(7) 0.0250(4) Uani d . 1
O O2 0.11946(8) 0.4078(3) 0.30793(7) 0.0216(4) Uani d . 1
C C8 0.09736(11) 0.4149(4) 0.25035(9) 0.0181(5) Uani d . 1
C C9 0.06788(11) 0.6204(4) 0.22986(10) 0.0192(5) Uani d . 1
H H9 0.0624 0.7460 0.2542 0.023 Uiso calc R 1
C C10 0.04640(11) 0.6402(4) 0.17308(10) 0.0177(5) Uani d . 1
H H10 0.0254 0.7794 0.1583 0.021 Uiso calc R 1
C C11 0.05562(11) 0.4570(4) 0.13782(10) 0.0169(5) Uani d . 1
C C12 0.08634(11) 0.2523(4) 0.15939(10) 0.0188(5) Uani d . 1
H H12 0.0928 0.1274 0.1352 0.023 Uiso calc R 1
C C13 0.10753(12) 0.2303(4) 0.21606(10) 0.0202(5) Uani d . 1
H H13 0.1286 0.0915 0.2310 0.024 Uiso calc R 1
C C14 0.03310(11) 0.4762(4) 0.07712(10) 0.0177(5) Uani d . 1
O O3 0.00181(9) 0.6673(3) 0.06089(7) 0.0272(4) Uani d . 1
H H3O -0.0102 0.6630 0.0263 0.041 Uiso calc R 1
O O4 0.04427(9) 0.3198(3) 0.04501(7) 0.0244(4) Uani d . 1
O O5 0.17781(9) 0.2955(3) 0.56890(7) 0.0238(4) Uani d . 1
C C15 0.21608(12) 0.4869(4) 0.59482(10) 0.0202(5) Uani d . 1
H H15A 0.1923 0.6365 0.5875 0.024 Uiso calc R 1
H H15B 0.2568 0.4988 0.5799 0.024 Uiso calc R 1
C C16 0.22997(12) 0.4371(4) 0.65666(10) 0.0207(5) Uani d . 1
H H16A 0.2560 0.2922 0.6636 0.025 Uiso calc R 1
H H16B 0.1889 0.4117 0.6704 0.025 Uiso calc R 1
C C17 0.26641(13) 0.6408(5) 0.68816(11) 0.0277(6) Uani d . 1
H H17A 0.3098 0.6505 0.6788 0.042 Uiso calc R 1
H H17B 0.2696 0.6153 0.7282 0.042 Uiso calc R 1
H H17C 0.2433 0.7875 0.6777 0.042 Uiso calc R 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
C2 C1 C6 119.3(2)
C2 C1 C7 123.2(2)
C6 C1 C7 117.6(2)
C1 C2 C3 120.8(2)
C1 C2 H2 119.6
C3 C2 H2 119.6
C2 C3 C4 119.6(2)
C2 C3 H3 120.2
C4 C3 H3 120.2
O5 C4 C3 124.9(2)
O5 C4 C5 115.3(2)
C3 C4 C5 119.7(2)
C6 C5 C4 120.2(2)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C1 120.4(2)
C5 C6 H6 119.8
C1 C6 H6 119.8
O1 C7 O2 122.9(2)
O1 C7 C1 125.5(2)
O2 C7 C1 111.61(19)
C7 O2 C8 118.23(18)
C9 C8 C13 122.2(2)
C9 C8 O2 116.1(2)
C13 C8 O2 121.7(2)
C8 C9 C10 118.8(2)
C8 C9 H9 120.6
C10 C9 H9 120.6
C11 C10 C9 120.2(2)
C11 C10 H10 119.9
C9 C10 H10 119.9
C10 C11 C12 120.0(2)
C10 C11 C14 120.7(2)
C12 C11 C14 119.3(2)
C13 C12 C11 120.2(2)
C13 C12 H12 119.9
C11 C12 H12 119.9
C8 C13 C12 118.6(2)
C8 C13 H13 120.7
C12 C13 H13 120.7
O4 C14 O3 123.5(2)
O4 C14 C11 121.2(2)
O3 C14 C11 115.3(2)
C14 O3 H3O 109.5
C4 O5 C15 118.32(19)
O5 C15 C16 107.18(19)
O5 C15 H15A 110.3
C16 C15 H15A 110.3
O5 C15 H15B 110.3
C16 C15 H15B 110.3
H15A C15 H15B 108.5
C15 C16 C17 110.8(2)
C15 C16 H16A 109.5
C17 C16 H16A 109.5
C15 C16 H16B 109.5
C17 C16 H16B 109.5
H16A C16 H16B 108.1
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.385(3)
C1 C6 1.400(3)
C1 C7 1.480(3)
C2 C3 1.391(4)
C2 H2 0.9500
C3 C4 1.395(3)
C3 H3 0.9500
C4 O5 1.358(3)
C4 C5 1.395(3)
C5 C6 1.379(3)
C5 H5 0.9500
C6 H6 0.9500
C7 O1 1.204(3)
C7 O2 1.367(3)
O2 C8 1.406(3)
C8 C9 1.380(3)
C8 C13 1.385(3)
C9 C10 1.389(3)
C9 H9 0.9500
C10 C11 1.389(3)
C10 H10 0.9500
C11 C12 1.394(3)
C11 C14 1.482(3)
C12 C13 1.387(3)
C12 H12 0.9500
C13 H13 0.9500
C14 O4 1.237(3)
C14 O3 1.300(3)
O3 H3O 0.8400
O5 C15 1.438(3)
C15 C16 1.516(3)
C15 H15A 0.9900
C15 H15B 0.9900
C16 C17 1.527(4)
C16 H16A 0.9900
C16 H16B 0.9900
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
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
O3 H3O O4 5_565 0.84 1.77 2.606(3) 172.1
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 0.2(4)
C7 C1 C2 C3 179.7(2)
C1 C2 C3 C4 0.0(4)
C2 C3 C4 O5 -179.5(2)
C2 C3 C4 C5 -0.3(4)
O5 C4 C5 C6 179.7(2)
C3 C4 C5 C6 0.3(4)
C4 C5 C6 C1 -0.1(4)
C2 C1 C6 C5 -0.1(4)
C7 C1 C6 C5 -179.7(2)
C2 C1 C7 O1 -176.3(2)
C6 C1 C7 O1 3.3(4)
C2 C1 C7 O2 3.8(3)
C6 C1 C7 O2 -176.6(2)
O1 C7 O2 C8 4.9(3)
C1 C7 O2 C8 -175.2(2)
C7 O2 C8 C9 122.6(2)
C7 O2 C8 C13 -60.5(3)
C13 C8 C9 C10 1.5(4)
O2 C8 C9 C10 178.5(2)
C8 C9 C10 C11 -1.1(3)
C9 C10 C11 C12 0.2(3)
C9 C10 C11 C14 -179.8(2)
C10 C11 C12 C13 0.3(3)
C14 C11 C12 C13 -179.7(2)
C9 C8 C13 C12 -1.1(4)
O2 C8 C13 C12 -177.8(2)
C11 C12 C13 C8 0.2(4)
C10 C11 C14 O4 175.9(2)
C12 C11 C14 O4 -4.1(3)
C10 C11 C14 O3 -3.7(3)
C12 C11 C14 O3 176.3(2)
C3 C4 O5 C15 -0.4(4)
C5 C4 O5 C15 -179.7(2)
C4 O5 C15 C16 -177.7(2)
O5 C15 C16 C17 -175.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 15492356
