#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/83/2228301.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228301
loop_
_publ_author_name
'Srinivasa, H. T.'
'Devarajegowda, H. C.'
'Arunkashi, H. K.'
'Meenakshi, T. G.'
_publ_section_title
;
 4-Ethoxyphenyl 4-[(methoxycarbonyl)oxy]benzoate
;
_journal_coeditor_code           FB2212
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3074
_journal_paper_doi               10.1107/S1600536810044661
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H16 O6'
_chemical_formula_moiety         'C17 H16 O6'
_chemical_formula_sum            'C17 H16 O6'
_chemical_formula_weight         316.30
_chemical_melting_point          356
_chemical_name_systematic
;
4-Ethoxyphenyl 4-[(methoxycarbonyl)oxy]benzoate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.949(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7397(5)
_cell_length_b                   16.9703(6)
_cell_length_c                   7.9324(3)
_cell_measurement_reflns_used    1797
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.40
_cell_volume                     1568.73(11)
_computing_cell_refinement
'CrysAlis Pro CCD (Oxford Diffraction, 2009)'
_computing_data_collection
'CrysAlis Pro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction
'CrysAlis Pro RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et
al.,
1993)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0839
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8839
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(CrysAlis Pro RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.110
_refine_ls_extinction_coef       0.0052(7)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    62
_refine_ls_number_parameters     211
_refine_ls_number_reflns         1797
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0352
_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)+(0.0418P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0852
_reflns_number_gt                1092
_reflns_number_total             1797
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fb2212.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2228301
_cod_database_fobs_code          2228301
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'
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_disorder_assembly
_atom_site_disorder_group
O O1 0.75904(19) 0.40401(15) 0.0153(3) 0.0827(7) Uani d . 1 . .
O O2 0.5908(2) 0.34329(14) 0.0242(3) 0.0794(7) Uani d . 1 . .
O O3 0.68466(18) 0.40619(14) 0.2481(3) 0.0749(6) Uani d . 1 . .
O O4 0.3150(2) 0.27835(12) 0.7091(3) 0.0812(7) Uani d . 1 . .
O O5 0.3405(2) 0.40346(11) 0.7901(3) 0.0681(6) Uani d . 1 . .
O O6 0.03480(19) 0.39014(13) 1.2645(3) 0.0725(6) Uani d . 1 . .
C C1 0.7605(3) 0.3799(3) -0.1598(5) 0.0961(12) Uani d . 1 . .
H H1A 0.8087 0.4149 -0.2145 0.144 Uiso calc R 1 . .
H H1B 0.6839 0.3815 -0.2180 0.144 Uiso calc R 1 . .
H H1C 0.7898 0.3271 -0.1629 0.144 Uiso calc R 1 . .
C C2 0.6705(3) 0.37896(19) 0.0872(4) 0.0630(8) Uani d . 1 . .
C C3 0.5995(3) 0.3876(2) 0.3513(3) 0.0604(8) Uani d . 1 . .
C C4 0.5405(3) 0.44911(18) 0.4107(4) 0.0610(8) Uani d . 1 . .
H H4 0.5522 0.5002 0.3743 0.073 Uiso calc R 1 . .
C C5 0.4636(2) 0.43453(17) 0.5251(4) 0.0587(8) Uani d . 1 . .
H H5 0.4253 0.4763 0.5693 0.070 Uiso calc R 1 . .
C C6 0.4428(2) 0.35787(17) 0.5747(3) 0.0523(7) Uani d . 1 . .
C C7 0.5019(3) 0.29643(17) 0.5101(4) 0.0610(8) Uani d . 1 . .
H H7 0.4877 0.2449 0.5415 0.073 Uiso calc R 1 . .
C C8 0.5816(3) 0.31082(18) 0.3996(4) 0.0653(8) Uani d . 1 . .
H H8 0.6224 0.2696 0.3583 0.078 Uiso calc R 1 . .
C C9 0.3606(2) 0.34004(17) 0.6952(4) 0.0549(7) Uani d . 1 . .
C C10 0.2640(3) 0.39527(16) 0.9136(4) 0.0577(8) Uani d . 1 . .
C C11 0.1571(3) 0.42874(17) 0.8805(4) 0.0639(8) Uani d . 1 . .
H H11 0.1354 0.4534 0.7769 0.077 Uiso calc R 1 . .
C C12 0.0830(3) 0.42581(17) 0.9999(4) 0.0620(8) Uani d . 1 . .
H H12 0.0105 0.4482 0.9774 0.074 Uiso calc R 1 . .
C C13 0.1157(3) 0.38941(16) 1.1553(4) 0.0530(7) Uani d . 1 . .
C C14 0.2230(3) 0.35663(17) 1.1868(4) 0.0635(8) Uani d . 1 . .
H H14 0.2455 0.3323 1.2905 0.076 Uiso calc R 1 . .
C C15 0.2983(3) 0.35972(17) 1.0643(4) 0.0628(8) Uani d . 1 . .
H H15 0.3712 0.3377 1.0855 0.075 Uiso calc R 1 . .
C C16 0.0587(3) 0.3503(2) 1.4190(5) 0.0816(10) Uani d . 1 . .
H H16A 0.1238 0.3744 1.4868 0.098 Uiso calc R 1 . .
H H16B 0.0773 0.2957 1.3989 0.098 Uiso calc R 1 . .
C C17 -0.0464(3) 0.3550(2) 1.5115(5) 0.0886(12) Uani d . 1 . .
H H17A -0.0310 0.3294 1.6198 0.133 Uiso calc R 1 . .
H H17B -0.1097 0.3294 1.4454 0.133 Uiso calc R 1 . .
H H17C -0.0654 0.4093 1.5281 0.133 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C1 . . 115.2(3) ?
C2 O3 C3 . . 117.4(2) ?
C9 O5 C10 . . 118.4(2) ?
C13 O6 C16 . . 118.2(3) ?
O1 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O2 C2 O1 . . 127.8(3) ?
O2 C2 O3 . . 125.4(3) ?
O1 C2 O3 . . 106.7(3) ?
C4 C3 C8 . . 121.6(3) ?
C4 C3 O3 . . 117.1(3) ?
C8 C3 O3 . . 121.2(3) ?
C3 C4 C5 . . 119.3(3) ?
C3 C4 H4 . . 120.4 ?
C5 C4 H4 . . 120.4 ?
C4 C5 C6 . . 120.4(3) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C7 C6 C5 . . 119.2(3) ?
C7 C6 C9 . . 118.9(3) ?
C5 C6 C9 . . 121.9(2) ?
C8 C7 C6 . . 120.7(3) ?
C8 C7 H7 . . 119.6 ?
C6 C7 H7 . . 119.6 ?
C7 C8 C3 . . 118.8(3) ?
C7 C8 H8 . . 120.6 ?
C3 C8 H8 . . 120.6 ?
O4 C9 O5 . . 122.7(3) ?
O4 C9 C6 . . 125.5(3) ?
O5 C9 C6 . . 111.8(2) ?
C15 C10 C11 . . 121.3(3) ?
C15 C10 O5 . . 120.6(3) ?
C11 C10 O5 . . 118.0(3) ?
C12 C11 C10 . . 119.8(3) ?
C12 C11 H11 . . 120.1 ?
C10 C11 H11 . . 120.1 ?
C11 C12 C13 . . 120.1(3) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
O6 C13 C14 . . 125.7(3) ?
O6 C13 C12 . . 114.9(3) ?
C14 C13 C12 . . 119.4(3) ?
C13 C14 C15 . . 120.3(3) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C10 C15 C14 . . 119.1(3) ?
C10 C15 H15 . . 120.5 ?
C14 C15 H15 . . 120.5 ?
O6 C16 C17 . . 108.1(3) ?
O6 C16 H16A . . 110.1 ?
C17 C16 H16A . . 110.1 ?
O6 C16 H16B . . 110.1 ?
C17 C16 H16B . . 110.1 ?
H16A C16 H16B . . 108.4 ?
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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.315(4) ?
O1 C1 . 1.450(4) ?
O2 C2 . 1.174(4) ?
O3 C2 . 1.349(4) ?
O3 C3 . 1.403(3) ?
O4 C9 . 1.187(3) ?
O5 C9 . 1.350(3) ?
O5 C10 . 1.414(3) ?
O6 C13 . 1.361(3) ?
O6 C16 . 1.398(4) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C3 C4 . 1.368(4) ?
C3 C8 . 1.381(4) ?
C4 C5 . 1.378(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.389(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.385(4) ?
C6 C9 . 1.470(4) ?
C7 C8 . 1.378(4) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C10 C15 . 1.356(4) ?
C10 C11 . 1.373(4) ?
C11 C12 . 1.362(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.390(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.373(4) ?
C14 C15 . 1.391(4) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 C17 . 1.512(5) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
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
C16 H16B O2 4_456 0.97 2.56 3.399(4) 145 yes
C1 H1B Cg1 1_554 0.96 2.99 3.853(4) 151 yes
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
C1 O1 C2 O2 . . . . -4.3(5) ?
C1 O1 C2 O3 . . . . 179.3(3) ?
C3 O3 C2 O2 . . . . 2.9(5) ?
C3 O3 C2 O1 . . . . 179.4(3) ?
C2 O3 C3 C4 . . . . -117.8(3) ?
C2 O3 C3 C8 . . . . 66.3(4) ?
C8 C3 C4 C5 . . . . 1.8(4) ?
O3 C3 C4 C5 . . . . -174.0(3) ?
C3 C4 C5 C6 . . . . -2.4(4) ?
C4 C5 C6 C7 . . . . 1.1(4) ?
C4 C5 C6 C9 . . . . -179.5(3) ?
C5 C6 C7 C8 . . . . 0.8(4) ?
C9 C6 C7 C8 . . . . -178.6(3) ?
C6 C7 C8 C3 . . . . -1.5(5) ?
C4 C3 C8 C7 . . . . 0.1(4) ?
O3 C3 C8 C7 . . . . 175.8(3) ?
C10 O5 C9 O4 . . . . 1.5(4) ?
C10 O5 C9 C6 . . . . -179.3(2) ?
C7 C6 C9 O4 . . . . -22.4(4) ?
C5 C6 C9 O4 . . . . 158.2(3) ?
C7 C6 C9 O5 . . . . 158.5(3) ?
C5 C6 C9 O5 . . . . -20.9(3) ?
C9 O5 C10 C15 . . . . 77.9(3) ?
C9 O5 C10 C11 . . . . -106.2(3) ?
C15 C10 C11 C12 . . . . -0.7(4) ?
O5 C10 C11 C12 . . . . -176.5(2) ?
C10 C11 C12 C13 . . . . 0.4(4) ?
C16 O6 C13 C14 . . . . -4.1(4) ?
C16 O6 C13 C12 . . . . 176.0(3) ?
C11 C12 C13 O6 . . . . 179.9(2) ?
C11 C12 C13 C14 . . . . 0.0(4) ?
O6 C13 C14 C15 . . . . -180.0(2) ?
C12 C13 C14 C15 . . . . -0.1(4) ?
C11 C10 C15 C14 . . . . 0.6(4) ?
O5 C10 C15 C14 . . . . 176.3(2) ?
C13 C14 C15 C10 . . . . -0.2(4) ?
C13 O6 C16 C17 . . . . -176.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 23076991
