#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/87/2228798.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_2228798
loop_
_publ_author_name
'Shen, Xu-Ji'
'Liu, Shi-Yu'
'Jia, Pu'
'Wang, Shi-Xiang'
'Zheng, Xiao-Hui'
_publ_section_title
;
 (E)-Isopropyl 3-(3,4-dihydroxyphenyl)acrylate
;
_journal_coeditor_code           LH5158
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o17
_journal_paper_doi               10.1107/S1600536810044272
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H14 O4'
_chemical_formula_moiety         'C12 H14 O4'
_chemical_formula_sum            'C12 H14 O4'
_chemical_formula_weight         222.23
_chemical_melting_point          415
_chemical_name_systematic
;
(E)-Isopropyl 3-(3,4-dihydroxyphenyl)acrylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                65.690(2)
_cell_angle_beta                 89.370(3)
_cell_angle_gamma                81.018(3)
_cell_formula_units_Z            2
_cell_length_a                   5.8830(14)
_cell_length_b                   9.644(2)
_cell_length_c                   11.428(3)
_cell_measurement_reflns_used    966
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.48
_cell_measurement_theta_min      2.35
_cell_volume                     582.6(2)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_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 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0146
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2938
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.132
_refine_ls_extinction_coef       0.059(11)
_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   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0453
_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)+(0.0822P)²+0.0498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1507
_reflns_number_gt                1436
_reflns_number_total             2042
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5158.cif
_cod_data_source_block           I
_cod_database_code               2228798
_cod_database_fobs_code          2228798
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.2370(2) -0.06896(13) 0.33802(11) 0.0681(4) Uani d . 1 . .
O O2 -0.0059(3) 0.11022(15) 0.18106(14) 0.0914(6) Uani d . 1 . .
O O3 0.3441(2) 0.87422(13) -0.01294(13) 0.0716(4) Uani d . 1 . .
H H3 0.2302 0.8794 -0.0562 0.107 Uiso calc R 1 . .
O O4 0.7644(2) 0.80457(15) 0.11324(14) 0.0808(5) Uani d . 1 . .
H H4 0.6907 0.8884 0.0653 0.121 Uiso calc R 1 . .
C C1 -0.0940(5) -0.1810(3) 0.4336(3) 0.1171(10) Uani d . 1 . .
H H1A -0.0341 -0.1952 0.5163 0.176 Uiso calc R 1 . .
H H1B -0.1815 -0.2610 0.4439 0.176 Uiso calc R 1 . .
H H1C -0.1918 -0.0823 0.3940 0.176 Uiso calc R 1 . .
C C2 0.1019(4) -0.1880(2) 0.34997(19) 0.0718(6) Uani d . 1 . .
H H2 0.0411 -0.1707 0.2647 0.086 Uiso calc R 1 . .
C C3 0.2645(4) -0.3381(2) 0.4062(2) 0.0847(7) Uani d . 1 . .
H H3A 0.3904 -0.3349 0.3515 0.127 Uiso calc R 1 . .
H H3B 0.1847 -0.4205 0.4132 0.127 Uiso calc R 1 . .
H H3C 0.3228 -0.3552 0.4900 0.127 Uiso calc R 1 . .
C C4 0.1664(3) 0.0739(2) 0.25094(17) 0.0612(5) Uani d . 1 . .
C C5 0.3170(3) 0.1807(2) 0.25085(17) 0.0631(5) Uani d . 1 . .
H H5 0.4498 0.1430 0.3053 0.076 Uiso calc R 1 . .
C C6 0.2693(3) 0.3291(2) 0.17549(16) 0.0585(5) Uani d . 1 . .
H H6 0.1344 0.3605 0.1232 0.070 Uiso calc R 1 . .
C C7 0.4000(3) 0.45108(19) 0.16300(15) 0.0539(5) Uani d . 1 . .
C C8 0.6149(3) 0.4221(2) 0.22568(17) 0.0606(5) Uani d . 1 . .
H H8 0.6797 0.3213 0.2795 0.073 Uiso calc R 1 . .
C C9 0.7324(3) 0.5406(2) 0.20894(17) 0.0639(5) Uani d . 1 . .
H H9 0.8752 0.5194 0.2522 0.077 Uiso calc R 1 . .
C C10 0.6403(3) 0.69140(19) 0.12826(16) 0.0582(5) Uani d . 1 . .
C C11 0.4264(3) 0.72247(19) 0.06532(15) 0.0550(5) Uani d . 1 . .
C C12 0.3083(3) 0.60347(18) 0.08283(15) 0.0550(5) Uani d . 1 . .
H H12 0.1645 0.6252 0.0403 0.066 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
C4 O1 C2 . . 118.69(14) ?
C11 O3 H3 . . 109.5 ?
C10 O4 H4 . . 109.5 ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C2 C3 . . 106.18(17) ?
O1 C2 C1 . . 108.92(17) ?
C3 C2 C1 . . 112.69(18) ?
O1 C2 H2 . . 109.7 ?
C3 C2 H2 . . 109.7 ?
C1 C2 H2 . . 109.7 ?
C2 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
O2 C4 O1 . . 123.04(17) ?
O2 C4 C5 . . 124.39(16) ?
O1 C4 C5 . . 112.57(15) ?
C6 C5 C4 . . 121.51(17) ?
C6 C5 H5 . . 119.2 ?
C4 C5 H5 . . 119.2 ?
C5 C6 C7 . . 128.67(18) ?
C5 C6 H6 . . 115.7 ?
C7 C6 H6 . . 115.7 ?
C8 C7 C12 . . 118.10(16) ?
C8 C7 C6 . . 122.98(16) ?
C12 C7 C6 . . 118.91(16) ?
C9 C8 C7 . . 120.69(17) ?
C9 C8 H8 . . 119.7 ?
C7 C8 H8 . . 119.7 ?
C8 C9 C10 . . 120.69(17) ?
C8 C9 H9 . . 119.7 ?
C10 C9 H9 . . 119.7 ?
O4 C10 C11 . . 122.00(15) ?
O4 C10 C9 . . 118.59(16) ?
C11 C10 C9 . . 119.41(16) ?
O3 C11 C12 . . 123.54(15) ?
O3 C11 C10 . . 116.67(15) ?
C12 C11 C10 . . 119.79(15) ?
C11 C12 C7 . . 121.31(16) ?
C11 C12 H12 . . 119.3 ?
C7 C12 H12 . . 119.3 ?
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 C4 . 1.327(2) ?
O1 C2 . 1.457(2) ?
O2 C4 . 1.210(2) ?
O3 C11 . 1.3735(19) ?
O3 H3 . 0.8200 ?
O4 C10 . 1.358(2) ?
O4 H4 . 0.8200 ?
C1 C2 . 1.500(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.496(3) ?
C2 H2 . 0.9800 ?
C3 H3A . 0.9600 ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
C4 C5 . 1.459(3) ?
C5 C6 . 1.317(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.462(2) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.391(3) ?
C7 C12 . 1.395(2) ?
C8 C9 . 1.372(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.386(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.384(2) ?
C11 C12 . 1.377(2) ?
C12 H12 . 0.9300 ?
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
O3 H3 O2 2_565 0.82 1.916 2.725(2) 168.96 yes
O4 H4 O3 2_675 0.82 2.090 2.792(2) 143.34 yes
O4 H4 O3 1_555 0.82 2.281 2.721(2) 114.13 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
C4 O1 C2 C3 . . . . 155.38(16) ?
C4 O1 C2 C1 . . . . -83.0(2) ?
C2 O1 C4 O2 . . . . 0.3(3) ?
C2 O1 C4 C5 . . . . 179.43(15) ?
O2 C4 C5 C6 . . . . 2.5(3) ?
O1 C4 C5 C6 . . . . -176.64(16) ?
C4 C5 C6 C7 . . . . -179.87(16) ?
C5 C6 C7 C8 . . . . 5.7(3) ?
C5 C6 C7 C12 . . . . -175.59(17) ?
C12 C7 C8 C9 . . . . 0.1(3) ?
C6 C7 C8 C9 . . . . 178.84(17) ?
C7 C8 C9 C10 . . . . -0.6(3) ?
C8 C9 C10 O4 . . . . -179.05(16) ?
C8 C9 C10 C11 . . . . 0.8(3) ?
O4 C10 C11 O3 . . . . -0.4(3) ?
C9 C10 C11 O3 . . . . 179.78(16) ?
O4 C10 C11 C12 . . . . 179.41(17) ?
C9 C10 C11 C12 . . . . -0.4(3) ?
O3 C11 C12 C7 . . . . 179.71(14) ?
C10 C11 C12 C7 . . . . -0.1(3) ?
C8 C7 C12 C11 . . . . 0.2(3) ?
C6 C7 C12 C11 . . . . -178.53(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8189372
