#------------------------------------------------------------------------------
#$Date: 2018-12-01 06:40:03 +0200 (Sat, 01 Dec 2018) $
#$Revision: 212280 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/03/1550314.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_1550314
loop_
_publ_author_name
'Abdou, Moaz M.'
'Matziari, Magdalini'
'O'Neill, Paul M.'
'Amigues, Eric'
'Zhou, Ruixue'
'Wang, Ruiyao'
'Ali, Basem F.'
_publ_section_title
;
 Methyl 3-(4-hydroxyphenyl)propionate
;
_journal_coeditor_code           RZ4027
_journal_issue                   11
_journal_name_full               IUCrData
_journal_page_first              x181662
_journal_paper_doi               10.1107/S2414314618016620
_journal_volume                  3
_journal_year                    2018
_chemical_formula_iupac          'C10 H12 O3'
_chemical_formula_moiety         'C10 H12 O3'
_chemical_formula_sum            'C10 H12 O3'
_chemical_formula_weight         180.20
_chemical_name_systematic
;
Methyl 3-(4-hydroxyphenyl)propionate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4774(6)
_cell_length_b                   11.1557(12)
_cell_length_c                   14.5610(17)
_cell_measurement_reflns_used    2736
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      3.34
_cell_volume                     889.74(17)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker D8 Venture diffractometer with PHOTON 100 CMOS detecter
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9443
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.341
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.150
_refine_ls_abs_structure_details
;
Flack x determined using 467 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   -0.5(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0427P)²+0.1279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0905
_reflns_number_gt                1390
_reflns_number_total             1756
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            rz4027sup1.cif
_cod_data_source_block           I
_cod_database_code               1550314
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_occupancy
O O1 0.5468(3) 0.18977(17) 0.77139(13) 0.0302(5) Uani d 1
H H1H 0.642(6) 0.235(3) 0.740(2) 0.051(11) Uiso d 1
O O2 0.1249(3) -0.19195(17) 0.84546(13) 0.0304(5) Uani d 1
O O3 -0.2348(3) -0.18421(16) 0.91771(11) 0.0267(5) Uani d 1
C C1 0.3762(5) 0.2573(2) 0.81696(17) 0.0220(6) Uani d 1
C C2 0.3865(5) 0.3815(2) 0.8200(2) 0.0270(7) Uani d 1
H H2A 0.515418 0.422762 0.789969 0.032 Uiso calc 1
C C3 0.2091(5) 0.4451(2) 0.86675(19) 0.0293(7) Uani d 1
H H3A 0.215294 0.530216 0.868476 0.035 Uiso calc 1
C C4 0.0235(6) 0.3849(2) 0.9108(2) 0.0293(7) Uani d 1
H H4A -0.097370 0.428212 0.943778 0.035 Uiso calc 1
C C5 0.0136(5) 0.2607(2) 0.90690(18) 0.0248(6) Uani d 1
H H5A -0.115233 0.219904 0.937426 0.030 Uiso calc 1
C C6 0.1866(4) 0.1949(2) 0.85970(16) 0.0203(6) Uani d 1
C C7 0.1802(5) 0.0596(2) 0.85041(19) 0.0251(6) Uani d 1
H H7A 0.191282 0.038987 0.784403 0.030 Uiso calc 1
H H7B 0.326584 0.026163 0.881019 0.030 Uiso calc 1
C C8 -0.0424(5) -0.0006(2) 0.88985(19) 0.0226(6) Uani d 1
H H8A -0.055581 0.020109 0.955777 0.027 Uiso calc 1
H H8B -0.189442 0.030922 0.858512 0.027 Uiso calc 1
C C9 -0.0375(5) -0.1341(2) 0.88018(19) 0.0209(6) Uani d 1
C C10 -0.2421(5) -0.3137(2) 0.91727(19) 0.0304(7) Uani d 1
H H10A -0.393610 -0.341096 0.946253 0.046 Uiso calc 1
H H10B -0.235700 -0.342708 0.853791 0.046 Uiso calc 1
H H10C -0.101883 -0.345081 0.951474 0.046 Uiso calc 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
C1 O1 H1H 111(2) ?
C9 O3 C10 116.1(2) y
O1 C1 C2 122.4(3) y
O1 C1 C6 116.6(2) y
C2 C1 C6 120.9(3) y
C3 C2 C1 120.0(3) ?
C3 C2 H2A 120.0 ?
C1 C2 H2A 120.0 ?
C4 C3 C2 119.8(3) ?
C4 C3 H3A 120.1 ?
C2 C3 H3A 120.1 ?
C3 C4 C5 119.8(3) ?
C3 C4 H4A 120.1 ?
C5 C4 H4A 120.1 ?
C6 C5 C4 121.6(3) y
C6 C5 H5A 119.2 ?
C4 C5 H5A 119.2 ?
C5 C6 C1 117.8(2) ?
C5 C6 C7 123.9(2) ?
C1 C6 C7 118.3(2) ?
C8 C7 C6 115.4(2) ?
C8 C7 H7A 108.4 ?
C6 C7 H7A 108.4 ?
C8 C7 H7B 108.4 ?
C6 C7 H7B 108.4 ?
H7A C7 H7B 107.5 ?
C9 C8 C7 113.2(2) y
C9 C8 H8A 108.9 ?
C7 C8 H8A 108.9 ?
C9 C8 H8B 108.9 ?
C7 C8 H8B 108.9 ?
H8A C8 H8B 107.8 ?
O2 C9 O3 122.9(2) y
O2 C9 C8 125.7(2) y
O3 C9 C8 111.4(2) y
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 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.372(3) y
O1 H1H 0.86(3) y
O2 C9 1.210(3) y
O3 C9 1.334(3) y
O3 C10 1.445(3) y
C1 C2 1.387(3) y
C1 C6 1.397(4) y
C2 C3 1.382(4) ?
C2 H2A 0.9500 ?
C3 C4 1.377(4) ?
C3 H3A 0.9500 ?
C4 C5 1.388(4) ?
C4 H4A 0.9500 ?
C5 C6 1.381(4) ?
C5 H5A 0.9500 ?
C6 C7 1.516(4) y
C7 C8 1.506(3) ?
C7 H7A 0.9900 ?
C7 H7B 0.9900 ?
C8 C9 1.496(3) y
C8 H8A 0.9900 ?
C8 H8B 0.9900 ?
C10 H10A 0.9800 ?
C10 H10B 0.9800 ?
C10 H10C 0.9800 ?
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 H1H O2 3_656 0.86(3) 1.96(4) 2.805(3) 169(3) 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
O1 C1 C2 C3 179.8(2)
C6 C1 C2 C3 0.8(4)
C1 C2 C3 C4 0.5(4)
C2 C3 C4 C5 -0.9(4)
C3 C4 C5 C6 0.1(5)
C4 C5 C6 C1 1.2(4)
C4 C5 C6 C7 -177.9(3)
O1 C1 C6 C5 179.3(2)
C2 C1 C6 C5 -1.6(4)
O1 C1 C6 C7 -1.6(3)
C2 C1 C6 C7 177.5(2)
C5 C6 C7 C8 5.0(4)
C1 C6 C7 C8 -174.0(2)
C6 C7 C8 C9 -179.1(2)
C10 O3 C9 O2 1.8(4)
C10 O3 C9 C8 -176.4(2)
C7 C8 C9 O2 0.5(4)
C7 C8 C9 O3 178.6(2)

_cod_database_fobs_code 1550314
