#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/97/2019703.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_2019703
loop_
_publ_author_name
'Li, Xiang'
'Wang, Zhi-Gang'
'Chen, Hou-He'
'Liu, Sheng-Gao'
_publ_section_title
;
 The antioxidant methyl
 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate
;
_journal_coeditor_code           WQ3074
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1050
_journal_page_last               1053
_journal_paper_doi               10.1107/S2053229614021445
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C18 H28 O3'
_chemical_formula_moiety         'C18 H28 O3'
_chemical_formula_sum            'C18 H28 O3'
_chemical_formula_weight         292.40
_chemical_name_systematic
;
Methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.343(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9191(14)
_cell_length_b                   18.164(4)
_cell_length_c                   16.605(4)
_cell_measurement_reflns_used    1787
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.574
_cell_measurement_theta_min      4.959
_cell_volume                     1766.4(7)
_computing_cell_refinement
;
SAINT (Bruker, 1999)
;
_computing_data_collection
;
SMART (Bruker, 1997)
;
_computing_data_reduction
;
SAINT (Bruker, 1999)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 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  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10007
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.100
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0543
_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)+(0.0802P)²+0.2237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1503
_refine_ls_wR_factor_ref         0.1644
_reflns_number_gt                2155
_reflns_number_total             3224
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wq3074sup1.cf
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2019703.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2019703
_cod_database_fobs_code          2019703
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           1997
#END Tags that were not found in dictionaries
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
_atom_site_symmetry_multiplicity
O O1 0.2878(3) 0.27812(8) 0.33694(10) 0.0699(5) Uani d . 1 1
H H1 0.3618 0.2406 0.3323 0.105 Uiso calc R 1 1
O O2 0.6255(3) 0.64083(9) 0.06254(12) 0.0914(6) Uani d . 1 1
O O3 0.9655(3) 0.59379(10) 0.05976(12) 0.0961(6) Uani d . 1 1
C C1 0.3321(3) 0.45709(10) 0.24595(11) 0.0490(5) Uani d . 1 1
H H1A 0.2943 0.5057 0.2556 0.059 Uiso calc R 1 1
C C2 0.2843(3) 0.40351(10) 0.30023(10) 0.0441(5) Uani d . 1 1
C C3 0.3436(3) 0.33064(10) 0.28341(11) 0.0449(5) Uani d . 1 1
C C4 0.4484(3) 0.31184(10) 0.21592(11) 0.0459(5) Uani d . 1 1
C C5 0.4906(3) 0.36922(11) 0.16486(11) 0.0512(5) Uani d . 1 1
H H5 0.5606 0.3584 0.1196 0.061 Uiso calc R 1 1
C C6 0.4337(3) 0.44152(10) 0.17805(11) 0.0493(5) Uani d . 1 1
C C7 0.4840(4) 0.50247(12) 0.12122(12) 0.0618(6) Uani d . 1 1
H H7A 0.4429 0.4856 0.0656 0.074 Uiso calc R 1 1
H H7B 0.3873 0.5443 0.1289 0.074 Uiso calc R 1 1
C C8 0.7239(4) 0.52749(14) 0.13217(16) 0.0806(7) Uani d . 1 1
H H8A 0.8192 0.4874 0.1182 0.097 Uiso calc R 1 1
H H8B 0.7709 0.5392 0.1891 0.097 Uiso calc R 1 1
C C9 0.7639(4) 0.59316(13) 0.08212(13) 0.0626(6) Uani d . 1 1
C C10 1.0221(5) 0.65549(18) 0.01166(19) 0.1028(10) Uani d . 1 1
H H10A 0.9384 0.6519 -0.0422 0.154 Uiso calc R 1 1
H H10B 1.1829 0.6551 0.0087 0.154 Uiso calc R 1 1
H H10C 0.9827 0.7005 0.0365 0.154 Uiso calc R 1 1
C C11 0.1727(3) 0.42419(11) 0.37542(11) 0.0503(5) Uani d . 1 1
C C12 0.1328(5) 0.50727(13) 0.37994(14) 0.0810(8) Uani d . 1 1
H H12A 0.0307 0.5228 0.3328 0.121 Uiso calc R 1 1
H H12B 0.2758 0.5326 0.3818 0.121 Uiso calc R 1 1
H H12C 0.0670 0.5184 0.4281 0.121 Uiso calc R 1 1
C C13 -0.0591(4) 0.38666(15) 0.37253(16) 0.0812(8) Uani d . 1 1
H H13A -0.1565 0.4008 0.3237 0.122 Uiso calc R 1 1
H H13B -0.1276 0.4013 0.4190 0.122 Uiso calc R 1 1
H H13C -0.0390 0.3342 0.3731 0.122 Uiso calc R 1 1
C C14 0.3312(4) 0.40281(15) 0.45330(12) 0.0754(7) Uani d . 1 1
H H14A 0.2629 0.4172 0.4999 0.113 Uiso calc R 1 1
H H14B 0.4753 0.4273 0.4545 0.113 Uiso calc R 1 1
H H14C 0.3545 0.3505 0.4542 0.113 Uiso calc R 1 1
C C15 0.5157(4) 0.23204(11) 0.19761(12) 0.0537(5) Uani d . 1 1
C C16 0.3028(4) 0.18252(13) 0.18234(17) 0.0779(7) Uani d . 1 1
H H16A 0.1991 0.2016 0.1373 0.117 Uiso calc R 1 1
H H16B 0.2290 0.1816 0.2301 0.117 Uiso calc R 1 1
H H16C 0.3475 0.1335 0.1700 0.117 Uiso calc R 1 1
C C17 0.6896(4) 0.20143(12) 0.26731(14) 0.0668(6) Uani d . 1 1
H H17A 0.6190 0.1972 0.3156 0.100 Uiso calc R 1 1
H H17B 0.8179 0.2342 0.2773 0.100 Uiso calc R 1 1
H H17C 0.7404 0.1538 0.2525 0.100 Uiso calc R 1 1
C C18 0.6314(5) 0.22816(13) 0.12084(15) 0.0760(7) Uani d . 1 1
H H18A 0.6737 0.1782 0.1117 0.114 Uiso calc R 1 1
H H18B 0.7656 0.2586 0.1279 0.114 Uiso calc R 1 1
H H18C 0.5275 0.2453 0.0749 0.114 Uiso calc R 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
_geom_angle_publ_flag
C3 O1 H1 109.5(17) y
C9 O3 C10 117.5(2) y
C6 C1 C2 122.82(18) ?
C6 C1 H1A 118.6 ?
C2 C1 H1A 118.6 ?
C1 C2 C3 116.86(17) ?
C1 C2 C11 120.57(16) ?
C3 C2 C11 122.57(16) ?
O1 C3 C2 115.69(16) y
O1 C3 C4 121.59(16) y
C4 C3 C2 122.71(16) ?
C5 C4 C3 116.47(17) ?
C5 C4 C15 120.62(17) ?
C3 C4 C15 122.91(16) ?
C6 C5 C4 123.17(18) ?
C6 C5 H5 118.4 ?
C4 C5 H5 118.4 ?
C5 C6 C1 117.97(17) ?
C5 C6 C7 121.51(18) ?
C1 C6 C7 120.52(18) ?
C8 C7 C6 114.92(18) ?
C8 C7 H7A 108.5 ?
C6 C7 H7A 108.5 ?
C8 C7 H7B 108.5 ?
C6 C7 H7B 108.5 ?
H7A C7 H7B 107.5 ?
C7 C8 C9 113.9(2) ?
C7 C8 H8A 108.8 ?
C9 C8 H8A 108.8 ?
C7 C8 H8B 108.8 ?
C9 C8 H8B 108.8 ?
H8A C8 H8B 107.7 ?
O2 C9 O3 122.2(2) y
O2 C9 C8 124.7(2) ?
O3 C9 C8 113.1(2) ?
O3 C10 H10A 109.5 ?
O3 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
O3 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
C13 C11 C12 107.3(2) ?
C13 C11 C14 110.51(19) ?
C12 C11 C14 106.74(18) ?
C13 C11 C2 110.77(16) ?
C12 C11 C2 111.54(16) ?
C14 C11 C2 109.86(16) ?
C11 C12 H12A 109.5 ?
C11 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C11 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
C11 C13 H13A 109.5 ?
C11 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C11 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C11 C14 H14A 109.5 ?
C11 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C11 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
C18 C15 C16 106.86(18) ?
C18 C15 C17 106.16(18) ?
C16 C15 C17 110.82(18) ?
C18 C15 C4 111.44(17) ?
C16 C15 C4 110.62(17) ?
C17 C15 C4 110.78(16) ?
C15 C16 H16A 109.5 ?
C15 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C15 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
C15 C17 H17A 109.5 ?
C15 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C15 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
C15 C18 H18A 109.5 ?
C15 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C15 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 1.376(2) y
O1 H1 0.820(17) y
O2 C9 1.204(3) ?
O3 C9 1.300(3) ?
O3 C10 1.444(3) ?
C1 C6 1.382(3) y
C1 C2 1.383(3) y
C1 H1A 0.9300 ?
C2 C3 1.408(3) y
C2 C11 1.541(3) y
C3 C4 1.400(3) y
C4 C5 1.389(3) y
C4 C15 1.545(3) y
C5 C6 1.381(3) y
C5 H5 0.9300 ?
C6 C7 1.512(3) y
C7 C8 1.477(3) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 C9 1.492(3) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 0.9600 ?
C11 C12 1.531(3) y
C11 C13 1.526(3) y
C11 C14 1.533(3) y
C12 H12A 0.9600 ?
C12 H12B 0.9600 ?
C12 H12C 0.9600 ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
C15 C16 1.539(3) y
C15 C17 1.537(3) y
C15 C18 1.534(3) y
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 0.9600 ?
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 0.9600 ?
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 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
O1 H1 O2 2_645 0.82 2.51 3.003(2) 119.8
C10 H10B O2 1_655 0.96 2.65 3.558(4) 157.0
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
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.2(3) ?
C6 C1 C2 C11 179.46(17) y
C1 C2 C3 O1 -178.07(17) y
C11 C2 C3 O1 2.3(3) y
C1 C2 C3 C4 0.7(3) y
C11 C2 C3 C4 -178.92(16) y
O1 C3 C4 C5 178.19(17) y
C2 C3 C4 C5 -0.5(3) y
O1 C3 C4 C15 -1.9(3) y
C2 C3 C4 C15 179.44(17) y
C3 C4 C5 C6 -0.2(3) y
C15 C4 C5 C6 179.83(18) y
C4 C5 C6 C1 0.7(3) y
C4 C5 C6 C7 179.62(18) y
C2 C1 C6 C5 -0.5(3) ?
C2 C1 C6 C7 -179.42(18) ?
C5 C6 C7 C8 -78.0(3) ?
C1 C6 C7 C8 100.8(3) ?
C6 C7 C8 C9 -173.4(2) ?
C10 O3 C9 O2 1.7(4) y
C10 O3 C9 C8 -179.4(2) y
C7 C8 C9 O2 30.7(4) ?
C7 C8 C9 O3 -148.2(2) ?
C1 C2 C11 C13 118.3(2) ?
C3 C2 C11 C13 -62.1(2) ?
C1 C2 C11 C12 -1.2(3) y
C3 C2 C11 C12 178.40(19) y
C1 C2 C11 C14 -119.3(2) ?
C3 C2 C11 C14 60.3(2) ?
C5 C4 C15 C18 1.1(3) y
C3 C4 C15 C18 -178.90(18) y
C5 C4 C15 C16 -117.7(2) ?
C3 C4 C15 C16 62.4(2) ?
C5 C4 C15 C17 119.0(2) y
C3 C4 C15 C17 -60.9(2) ?
