#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/04/2210450.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_2210450
loop_
_publ_author_name
'Chun-Nian Xia'
'Wei-Xiao Hu'
'Wei Zhou'
_publ_section_title
;
 tert-Butyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
;
_journal_coeditor_code           XU2113
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4118
_journal_page_last               o4119
_journal_paper_doi               10.1107/S1600536806033642
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H16 O4'
_chemical_formula_moiety         'C13 H16 O4'
_chemical_formula_sum            'C13 H16 O4'
_chemical_formula_weight         236.26
_chemical_melting_point          405.5(5)
_chemical_name_systematic
;
Tert-butyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.005(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.334(3)
_cell_length_b                   11.000(3)
_cell_length_c                   12.701(4)
_cell_measurement_reflns_used    987
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.7
_cell_measurement_theta_min      2.8
_cell_volume                     1291.4(7)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2003)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_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  0.078
_diffrn_reflns_av_sigmaI/netI    0.059
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6285
_diffrn_reflns_theta_full        27.1
_diffrn_reflns_theta_max         27.1
_diffrn_reflns_theta_min         2.2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
?
;
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.42
_refine_ls_extinction_coef       0.031(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.097
_refine_ls_R_factor_gt           0.067
_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)+(0.1179P)²+0.1691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.189
_refine_ls_wR_factor_ref         0.226
_reflns_number_gt                1857
_reflns_number_total             2826
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2113.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '405-406' was changed to '405.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '405-406' was changed to '405.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210450
_cod_database_fobs_code          2210450
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
O O1 0.0842(2) 0.06779(15) 0.61082(11) 0.0571(5) Uani d . 1
H H1 0.1201 0.1346 0.6265 0.086 Uiso calc R 1
O O2 0.0780(2) -0.17438(16) 0.57016(12) 0.0606(5) Uani d . 1
H H2 0.0518 -0.1171 0.5308 0.091 Uiso calc R 1
O O3 0.2151(2) 0.22496(17) 1.17783(13) 0.0748(7) Uani d . 1
O O4 0.3232(2) 0.04277(16) 1.19843(11) 0.0596(5) Uani d . 1
C C1 0.1819(2) -0.0549(2) 0.88120(16) 0.0477(6) Uani d U 1
C C2 0.1478(2) 0.0285(2) 0.79901(15) 0.0466(5) Uani d . 1
H H2A 0.1474 0.1112 0.8144 0.056 Uiso calc R 1
C C3 0.1148(2) -0.0097(2) 0.69547(15) 0.0422(5) Uani d . 1
C C4 0.1110(2) -0.1336(2) 0.67176(15) 0.0436(5) Uani d . 1
C C5 0.1432(3) -0.2163(2) 0.75218(17) 0.0528(6) Uani d . 1
H H5 0.1404 -0.2990 0.7369 0.063 Uiso calc R 1
C C6 0.1801(3) -0.1775(2) 0.85601(17) 0.0499(6) Uani d U 1
H H6 0.2039 -0.2345 0.9097 0.060 Uiso calc R 1
C C7 0.2206(3) -0.0162(2) 0.99188(16) 0.0513(6) Uani d . 1
H H7 0.2654 -0.0739 1.0390 0.062 Uiso calc R 1
C C8 0.1986(3) 0.0915(2) 1.03165(17) 0.0583(7) Uani d . 1
H H8 0.1507 0.1495 0.9864 0.070 Uiso calc R 1
C C9 0.2447(3) 0.1262(2) 1.14265(17) 0.0551(6) Uani d . 1
C C10 0.3837(2) 0.0615(2) 1.31156(15) 0.0489(6) Uani d . 1
C C11 0.4798(3) 0.1700(3) 1.3252(3) 0.0818(9) Uani d . 1
H H11A 0.5453 0.1681 1.2733 0.123 Uiso calc R 1
H H11B 0.5339 0.1694 1.3953 0.123 Uiso calc R 1
H H11C 0.4221 0.2425 1.3159 0.123 Uiso calc R 1
C C12 0.2613(3) 0.0679(3) 1.3763(2) 0.0696(8) Uani d . 1
H H12A 0.2030 0.1381 1.3555 0.104 Uiso calc R 1
H H12B 0.2994 0.0737 1.4503 0.104 Uiso calc R 1
H H12C 0.2031 -0.0041 1.3644 0.104 Uiso calc R 1
C C13 0.4710(3) -0.0533(3) 1.3350(2) 0.0734(8) Uani d . 1
H H13A 0.4085 -0.1226 1.3225 0.110 Uiso calc R 1
H H13B 0.5152 -0.0528 1.4079 0.110 Uiso calc R 1
H H13C 0.5448 -0.0573 1.2895 0.110 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
C3 O1 H1 109.5
C4 O2 H2 109.5
C9 O4 C10 122.17(18)
C6 C1 C2 118.30(19)
C6 C1 C7 119.9(2)
C2 C1 C7 121.8(2)
C3 C2 C1 120.8(2)
C3 C2 H2A 119.6
C1 C2 H2A 119.6
O1 C3 C2 123.7(2)
O1 C3 C4 116.24(18)
C2 C3 C4 120.10(19)
O2 C4 C5 119.1(2)
O2 C4 C3 121.51(19)
C5 C4 C3 119.43(19)
C4 C5 C6 120.4(2)
C4 C5 H5 119.8
C6 C5 H5 119.8
C5 C6 C1 120.9(2)
C5 C6 H6 119.5
C1 C6 H6 119.5
C8 C7 C1 126.8(2)
C8 C7 H7 116.6
C1 C7 H7 116.6
C7 C8 C9 124.3(2)
C7 C8 H8 117.9
C9 C8 H8 117.9
O3 C9 O4 124.1(2)
O3 C9 C8 122.2(2)
O4 C9 C8 113.7(2)
O4 C10 C11 111.5(2)
O4 C10 C12 108.76(18)
C11 C10 C12 113.0(2)
O4 C10 C13 101.38(18)
C11 C10 C13 110.4(2)
C12 C10 C13 111.3(2)
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C10 C13 H13A 109.5
C10 C13 H13B 109.5
H13A C13 H13B 109.5
C10 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.371(2)
O1 H1 0.8200
O2 C4 1.360(2)
O2 H2 0.8200
O3 C9 1.221(3)
O4 C9 1.318(3)
O4 C10 1.483(2)
C1 C6 1.386(3)
C1 C2 1.393(3)
C1 C7 1.465(3)
C2 C3 1.374(3)
C2 H2A 0.9300
C3 C4 1.395(3)
C4 C5 1.370(3)
C5 C6 1.383(3)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.316(3)
C7 H7 0.9300
C8 C9 1.466(3)
C8 H8 0.9300
C10 C11 1.489(4)
C10 C12 1.499(4)
C10 C13 1.509(4)
C11 H11A 0.9599
C11 H11B 0.9599
C11 H11C 0.9599
C12 H12A 0.9599
C12 H12B 0.9599
C12 H12C 0.9599
C13 H13A 0.9599
C13 H13B 0.9599
C13 H13C 0.9599
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
O1 H1 O3 4_565 0.82 1.85 2.669(2) 172 yes
O2 H2 O1 3_556 0.82 2.12 2.826(2) 144 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
C6 C1 C2 C3 -0.7(3)
C7 C1 C2 C3 178.6(2)
C1 C2 C3 O1 -178.1(2)
C1 C2 C3 C4 1.9(3)
O1 C3 C4 O2 -0.3(3)
C2 C3 C4 O2 179.7(2)
O1 C3 C4 C5 178.7(2)
C2 C3 C4 C5 -1.3(3)
O2 C4 C5 C6 178.7(2)
C3 C4 C5 C6 -0.3(3)
C4 C5 C6 C1 1.5(4)
C2 C1 C6 C5 -0.9(4)
C7 C1 C6 C5 179.7(2)
C6 C1 C7 C8 -164.7(3)
C2 C1 C7 C8 16.0(4)
C1 C7 C8 C9 -177.6(2)
C10 O4 C9 O3 0.2(4)
C10 O4 C9 C8 178.4(2)
C7 C8 C9 O3 -175.8(3)
C7 C8 C9 O4 6.0(4)
C9 O4 C10 C11 -58.7(3)
C9 O4 C10 C12 66.6(3)
C9 O4 C10 C13 -176.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655047
