#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/63/2236372.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_2236372
loop_
_publ_author_name
'Alexander, Catherine Thomas'
'Vargas, David'
'Fronczek, Frank R.'
'Watkins, Steven F.'
_publ_section_title
;
 1-(2-Hydroxy-5-methoxyphenyl)-3-methylbut-2-en-1-one
;
_journal_coeditor_code           IM2405
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3126
_journal_paper_doi               10.1107/S1600536812042158
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C12 H14 O3'
_chemical_formula_moiety         'C12 H14 O3'
_chemical_formula_sum            'C12 H14 O3'
_chemical_formula_weight         206.23
_chemical_name_systematic
;
1-(2-Hydroxy-5-methoxyphenyl)-3-methylbut-2-en-1-one
;
_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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.409(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.027(3)
_cell_length_b                   5.8160(10)
_cell_length_c                   12.829(3)
_cell_measurement_pressure       101.3
_cell_measurement_reflns_used    3442
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      32.6
_cell_measurement_theta_min      2.5
_cell_volume                     1046.3(4)
_computing_cell_refinement
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_ambient_temperature      100.0(5)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans '
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6425
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         32.59
_diffrn_reflns_theta_min         3.18
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9788
_exptl_absorpt_correction_T_min  0.9592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(HKL Scalepack; Otwinowski & Minor 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.222
_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_constraints    0
_refine_ls_number_parameters     143
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0692P)²+0.2297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1267
_reflns_number_gt                3179
_reflns_number_total             3784
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2405.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236372
_cod_database_fobs_code          2236372
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
C C1 0.38220(6) 1.03873(14) 0.88580(6) 0.01713(16) Uani d . 1 1
C C2 0.31710(6) 0.89827(14) 0.93398(6) 0.01652(15) Uani d . 1 1
H H2 0.3003 0.9281 1.0040 0.020 Uiso calc R 1 1
C C3 0.27530(6) 0.71019(14) 0.87973(6) 0.01641(15) Uani d . 1 1
C C4 0.30238(6) 0.66752(15) 0.77617(6) 0.01796(16) Uani d . 1 1
C C5 0.36779(6) 0.81313(15) 0.72851(6) 0.01992(17) Uani d . 1 1
H H5 0.3853 0.7853 0.6586 0.024 Uiso calc R 1 1
C C6 0.40689(6) 0.99610(16) 0.78231(6) 0.01999(17) Uani d . 1 1
H H6 0.4509 1.0944 0.7491 0.024 Uiso calc R 1 1
C C7 0.20366(6) 0.55840(14) 0.92711(7) 0.01901(16) Uani d . 1 1
C C8 0.17084(6) 0.60621(15) 1.03279(7) 0.01893(16) Uani d . 1 1
H H8 0.1897 0.7485 1.0632 0.023 Uiso calc R 1 1
C C9 0.11620(6) 0.46622(15) 1.09083(7) 0.01933(16) Uani d . 1 1
C C10 0.08404(7) 0.54666(17) 1.19537(7) 0.02467(19) Uani d . 1 1
H H10A 0.1069 0.7037 1.2079 0.037 Uiso calc R 1 1
H H10B 0.1100 0.4446 1.2498 0.037 Uiso calc R 1 1
H H10C 0.0142 0.5442 1.1967 0.037 Uiso calc R 1 1
C C11 0.08255(7) 0.23100(16) 1.05970(8) 0.02593(19) Uani d . 1 1
H H11A 0.0197 0.2424 1.0251 0.039 Uiso calc R 1 1
H H11B 0.0781 0.1342 1.1219 0.039 Uiso calc R 1 1
H H11C 0.1279 0.1625 1.0117 0.039 Uiso calc R 1 1
C C12 0.40983(6) 1.26466(15) 1.03865(7) 0.02072(17) Uani d . 1 1
H H12A 0.3425 1.3041 1.0465 0.031 Uiso calc R 1 1
H H12B 0.4497 1.3925 1.0637 0.031 Uiso calc R 1 1
H H12C 0.4249 1.1263 1.0794 0.031 Uiso calc R 1 1
O O1 0.42786(5) 1.22263(11) 0.93148(5) 0.02247(15) Uani d . 1 1
O O2 0.26717(5) 0.49087(12) 0.71825(5) 0.02388(15) Uani d . 1 1
H H2A 0.2287(12) 0.416(3) 0.7580(14) 0.052(5) Uiso d . 1 1
O O3 0.17042(5) 0.39337(13) 0.87547(6) 0.02755(16) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
O1 C1 C2 125.22(7)
O1 C1 C6 114.77(7)
C2 C1 C6 120.00(8)
C1 C2 C3 120.46(7)
C1 C2 H2 119.8
C3 C2 H2 119.8
C4 C3 C2 118.71(7)
C4 C3 C7 118.86(7)
C2 C3 C7 122.43(7)
O2 C4 C5 116.96(8)
O2 C4 C3 123.13(8)
C5 C4 C3 119.91(8)
C6 C5 C4 120.43(8)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 C1 120.48(8)
C5 C6 H6 119.8
C1 C6 H6 119.8
O3 C7 C8 120.88(8)
O3 C7 C3 119.26(8)
C8 C7 C3 119.85(7)
C9 C8 C7 126.04(8)
C9 C8 H8 117
C7 C8 H8 117
C8 C9 C11 125.55(8)
C8 C9 C10 119.40(8)
C11 C9 C10 115.05(8)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C9 C11 H11A 109.5
C9 C11 H11B 109.5
H11A C11 H11B 109.5
C9 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O1 C12 H12A 109.5
O1 C12 H12B 109.5
H12A C12 H12B 109.5
O1 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C1 O1 C12 117.01(7)
C4 O2 H2A 106.4(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.3708(10)
C1 C2 1.3824(11)
C1 C6 1.4023(12)
C2 C3 1.4159(11)
C2 H2 0.95
C3 C4 1.4127(12)
C3 C7 1.4795(12)
C4 O2 1.3540(10)
C4 C5 1.4002(12)
C5 C6 1.3751(12)
C5 H5 0.95
C6 H6 0.95
C7 O3 1.2499(11)
C7 C8 1.4690(12)
C8 C9 1.3538(12)
C8 H8 0.95
C9 C11 1.4982(13)
C9 C10 1.5003(13)
C10 H10A 0.98
C10 H10B 0.98
C10 H10C 0.98
C11 H11A 0.98
C11 H11B 0.98
C11 H11C 0.98
C12 O1 1.4251(11)
C12 H12A 0.98
C12 H12B 0.98
C12 H12C 0.98
O2 H2A 0.870(18)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H2A O3 0.87(2) 1.74(2) 2.5230(10) 149(2)
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 -178.95(8)
C6 C1 C2 C3 0.33(13)
C1 C2 C3 C4 0.82(12)
C1 C2 C3 C7 -178.54(8)
C2 C3 C4 O2 179.35(7)
C7 C3 C4 O2 -1.28(12)
C2 C3 C4 C5 -1.39(12)
C7 C3 C4 C5 177.99(8)
O2 C4 C5 C6 -179.87(8)
C3 C4 C5 C6 0.82(13)
C4 C5 C6 C1 0.34(13)
O1 C1 C6 C5 178.43(8)
C2 C1 C6 C5 -0.92(13)
C4 C3 C7 O3 1.59(12)
C2 C3 C7 O3 -179.06(8)
C4 C3 C7 C8 -176.96(7)
C2 C3 C7 C8 2.39(12)
O3 C7 C8 C9 11.11(14)
C3 C7 C8 C9 -170.37(8)
C7 C8 C9 C11 2.89(14)
C7 C8 C9 C10 -176.50(8)
C2 C1 O1 C12 3.14(12)
C6 C1 O1 C12 -176.18(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10532827
