#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/06/2230620.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_2230620
loop_
_publ_author_name
'Liu, Xi-Wang'
'Li, Jian-Yong'
'Yang, Ya-Jun'
'Zhang, Ji-Yu'
_publ_section_title
;
 4-Allyl-2-methoxyphenyl 2-acetoxybenzoate
;
_journal_coeditor_code           EZ2244
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1621
_journal_paper_doi               10.1107/S1600536811021416
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H18 O5'
_chemical_formula_moiety         'C19 H18 O5'
_chemical_formula_sum            'C19 H18 O5'
_chemical_formula_weight         326.33
_chemical_melting_point_gt       344
_chemical_melting_point_lt       345
_chemical_name_common            '4-allyl-2-methoxyphenyl 2-acetoxybenzoate '
_chemical_name_systematic
;
4-Allyl-2-methoxyphenyl 2-acetoxybenzoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 109.020(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.60(2)
_cell_length_b                   12.58(2)
_cell_length_c                   13.23(2)
_cell_measurement_reflns_used    2334
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.88
_cell_measurement_theta_min      2.30
_cell_volume                     1668(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0649
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8695
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9796
_exptl_absorpt_correction_T_min  0.9759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.248
_refine_ls_extinction_coef       0.044(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0505
_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)+(0.0532P)²+0.6544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1424
_reflns_number_gt                1786
_reflns_number_total             3089
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2244.cif
_cod_data_source_block           I
_cod_original_cell_volume        1667(5)
_cod_original_sg_symbol_Hall     'P 21/n'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2230620
loop_
_symmetry_equiv_pos_as_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'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5429(3) 0.8815(2) 1.1109(2) 0.0552(7) Uani d . 1 1 . .
H H1 0.5154 0.9490 1.0842 0.066 Uiso calc R 1 1 . .
C C2 0.6740(3) 0.8662(3) 1.1758(3) 0.0651(9) Uani d . 1 1 . .
H H2 0.7329 0.9233 1.1933 0.078 Uiso calc R 1 1 . .
C C3 0.7161(3) 0.7671(3) 1.2139(2) 0.0667(9) Uani d . 1 1 . .
H H3 0.8038 0.7566 1.2575 0.080 Uiso calc R 1 1 . .
C C4 0.6290(3) 0.6826(3) 1.1880(2) 0.0589(8) Uani d . 1 1 . .
H H4 0.6582 0.6150 1.2135 0.071 Uiso calc R 1 1 . .
C C5 0.4980(2) 0.6979(2) 1.1242(2) 0.0454(6) Uani d . 1 1 . .
C C6 0.4519(2) 0.7981(2) 1.0850(2) 0.0445(6) Uani d . 1 1 . .
C C7 0.3121(3) 0.8251(2) 1.0192(2) 0.0460(6) Uani d . 1 1 . .
C C8 0.0856(2) 0.7755(2) 0.9839(2) 0.0457(7) Uani d . 1 1 . .
C C9 0.0242(2) 0.8431(2) 1.0363(2) 0.0451(6) Uani d . 1 1 . .
C C10 -0.1134(3) 0.8549(2) 0.9951(2) 0.0522(7) Uani d . 1 1 . .
H H10 -0.1563 0.8996 1.0295 0.063 Uiso calc R 1 1 . .
C C11 -0.1880(3) 0.8015(2) 0.9038(2) 0.0563(7) Uani d . 1 1 . .
C C12 -0.1244(3) 0.7362(2) 0.8531(2) 0.0619(8) Uani d . 1 1 . .
H H12 -0.1735 0.7007 0.7911 0.074 Uiso calc R 1 1 . .
C C13 0.0134(3) 0.7226(2) 0.8936(2) 0.0563(8) Uani d . 1 1 . .
H H13 0.0560 0.6776 0.8593 0.068 Uiso calc R 1 1 . .
C C14 0.3662(3) 0.5694(2) 1.0060(3) 0.0523(7) Uani d . 1 1 . .
C C15 0.2725(3) 0.4813(3) 1.0018(3) 0.0784(10) Uani d . 1 1 . .
H H15A 0.2235 0.4650 0.9286 0.118 Uiso calc R 1 1 . .
H H15B 0.2114 0.5019 1.0382 0.118 Uiso calc R 1 1 . .
H H15C 0.3216 0.4197 1.0359 0.118 Uiso calc R 1 1 . .
C C16 0.0468(3) 0.9576(2) 1.1848(2) 0.0664(8) Uani d . 1 1 . .
H H16A -0.0043 1.0124 1.1391 0.100 Uiso calc R 1 1 . .
H H16B 0.1152 0.9894 1.2436 0.100 Uiso calc R 1 1 . .
H H16C -0.0109 0.9156 1.2118 0.100 Uiso calc R 1 1 . .
C C17 -0.3382(3) 0.8185(3) 0.8597(3) 0.0794(10) Uani d . 1 1 . .
H H17A -0.3803 0.7545 0.8231 0.095 Uiso calc R 1 1 . .
H H17B -0.3719 0.8312 0.9186 0.095 Uiso calc R 1 1 . .
C C18 -0.3746(4) 0.9083(4) 0.7853(5) 0.1113(15) Uani d . 1 1 . .
H H18 -0.3360 0.9723 0.8151 0.134 Uiso calc R 1 1 . .
C C19 -0.4456(4) 0.9161(4) 0.6917(4) 0.1173(16) Uani d . 1 1 . .
H H19A -0.4886 0.8564 0.6548 0.141 Uiso calc R 1 1 . .
H H19B -0.4565 0.9817 0.6575 0.141 Uiso calc R 1 1 . .
O O1 0.41425(17) 0.60944(14) 1.10660(15) 0.0517(5) Uani d . 1 1 . .
O O4 0.22313(15) 0.75382(14) 1.03094(14) 0.0512(5) Uani d . 1 1 . .
O O2 0.3986(2) 0.60219(17) 0.93385(16) 0.0684(6) Uani d . 1 1 . .
O O3 0.28083(19) 0.90274(16) 0.96467(17) 0.0681(6) Uani d . 1 1 . .
O O5 0.10653(18) 0.89150(15) 1.12579(15) 0.0582(5) 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 121.5(3) ?
C6 C1 H1 . . 119.3 ?
C2 C1 H1 . . 119.3 ?
C3 C2 C1 . . 119.8(3) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
C2 C3 C4 . . 120.1(3) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
C3 C4 C5 . . 120.2(3) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C4 C5 C6 . . 121.0(3) ?
C4 C5 O1 . . 116.6(3) ?
C6 C5 O1 . . 122.3(3) ?
C1 C6 C5 . . 117.5(3) ?
C1 C6 C7 . . 116.7(3) ?
C5 C6 C7 . . 125.8(2) ?
O3 C7 O4 . . 123.2(3) ?
O3 C7 C6 . . 124.4(2) ?
O4 C7 C6 . . 112.4(2) ?
C13 C8 C9 . . 121.1(3) ?
C13 C8 O4 . . 119.7(2) ?
C9 C8 O4 . . 118.9(3) ?
O5 C9 C8 . . 115.9(3) ?
O5 C9 C10 . . 125.9(2) ?
C8 C9 C10 . . 118.3(3) ?
C11 C10 C9 . . 121.3(2) ?
C11 C10 H10 . . 119.4 ?
C9 C10 H10 . . 119.4 ?
C12 C11 C10 . . 119.1(3) ?
C12 C11 C17 . . 121.2(3) ?
C10 C11 C17 . . 119.7(3) ?
C11 C12 C13 . . 120.5(3) ?
C11 C12 H12 . . 119.7 ?
C13 C12 H12 . . 119.7 ?
C8 C13 C12 . . 119.7(3) ?
C8 C13 H13 . . 120.1 ?
C12 C13 H13 . . 120.1 ?
O2 C14 O1 . . 123.0(3) ?
O2 C14 C15 . . 126.7(3) ?
O1 C14 C15 . . 110.4(3) ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O5 C16 H16A . . 109.5 ?
O5 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O5 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C18 C17 C11 . . 112.3(3) ?
C18 C17 H17A . . 109.1 ?
C11 C17 H17A . . 109.1 ?
C18 C17 H17B . . 109.1 ?
C11 C17 H17B . . 109.1 ?
H17A C17 H17B . . 107.9 ?
C19 C18 C17 . . 132.9(5) ?
C19 C18 H18 . . 113.5 ?
C17 C18 H18 . . 113.5 ?
C18 C19 H19A . . 120.0 ?
C18 C19 H19B . . 120.0 ?
H19A C19 H19B . . 120.0 ?
C14 O1 C5 . . 118.3(2) ?
C7 O4 C8 . . 118.8(2) ?
C9 O5 C16 . . 117.7(2) ?
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
C1 C6 . 1.390(4) ?
C1 C2 . 1.387(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.364(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.376(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.383(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.390(4) ?
C5 O1 . 1.394(4) ?
C6 C7 . 1.492(4) ?
C7 O3 . 1.195(3) ?
C7 O4 . 1.346(3) ?
C8 C13 . 1.363(4) ?
C8 C9 . 1.386(4) ?
C8 O4 . 1.412(4) ?
C9 O5 . 1.364(3) ?
C9 C10 . 1.389(4) ?
C10 C11 . 1.382(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.368(4) ?
C11 C17 . 1.521(5) ?
C12 C13 . 1.392(5) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 O2 . 1.189(4) ?
C14 O1 . 1.357(4) ?
C14 C15 . 1.477(4) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 O5 . 1.423(3) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 C18 . 1.465(6) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 C19 . 1.226(6) ?
C18 H18 . 0.9300 ?
C19 H19A . 0.9300 ?
C19 H19B . 0.9300 ?
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
C6 C1 C2 C3 . . . . 1.2(4) ?
C1 C2 C3 C4 . . . . 0.1(4) ?
C2 C3 C4 C5 . . . . -0.7(4) ?
C3 C4 C5 C6 . . . . 0.1(4) ?
C3 C4 C5 O1 . . . . -176.5(2) ?
C2 C1 C6 C5 . . . . -1.7(4) ?
C2 C1 C6 C7 . . . . 176.9(2) ?
C4 C5 C6 C1 . . . . 1.0(4) ?
O1 C5 C6 C1 . . . . 177.5(2) ?
C4 C5 C6 C7 . . . . -177.5(2) ?
O1 C5 C6 C7 . . . . -1.0(4) ?
C1 C6 C7 O3 . . . . 21.1(4) ?
C5 C6 C7 O3 . . . . -160.4(3) ?
C1 C6 C7 O4 . . . . -156.7(2) ?
C5 C6 C7 O4 . . . . 21.8(3) ?
C13 C8 C9 O5 . . . . 179.9(2) ?
O4 C8 C9 O5 . . . . 6.0(3) ?
C13 C8 C9 C10 . . . . 0.6(4) ?
O4 C8 C9 C10 . . . . -173.3(2) ?
O5 C9 C10 C11 . . . . -179.6(2) ?
C8 C9 C10 C11 . . . . -0.4(4) ?
C9 C10 C11 C12 . . . . -0.4(4) ?
C9 C10 C11 C17 . . . . -178.6(3) ?
C10 C11 C12 C13 . . . . 0.9(4) ?
C17 C11 C12 C13 . . . . 179.1(3) ?
C9 C8 C13 C12 . . . . -0.1(4) ?
O4 C8 C13 C12 . . . . 173.8(2) ?
C11 C12 C13 C8 . . . . -0.6(4) ?
C12 C11 C17 C18 . . . . -90.0(5) ?
C10 C11 C17 C18 . . . . 88.1(4) ?
C11 C17 C18 C19 . . . . 122.2(5) ?
O2 C14 O1 C5 . . . . 4.8(4) ?
C15 C14 O1 C5 . . . . -176.0(2) ?
C4 C5 O1 C14 . . . . -113.6(3) ?
C6 C5 O1 C14 . . . . 69.8(3) ?
O3 C7 O4 C8 . . . . -5.3(4) ?
C6 C7 O4 C8 . . . . 172.4(2) ?
C13 C8 O4 C7 . . . . 105.2(3) ?
C9 C8 O4 C7 . . . . -80.8(3) ?
C8 C9 O5 C16 . . . . -177.1(2) ?
C10 C9 O5 C16 . . . . 2.2(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656758
