#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/71/2017136.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_2017136
loop_
_publ_author_name
'Jones, Peter G.'
'Mangalagiu, Ionel I.'
_publ_section_title
;
 Concomitant polymorphism and conformational isomerism in
 4-acetylresorcinol
;
_journal_coeditor_code           GD3292
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o300
_journal_page_last               o302
_journal_paper_doi               10.1107/S0108270109017715
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C8 H8 O3'
_chemical_formula_moiety         'C8 H8 O3'
_chemical_formula_sum            'C8 H8 O3'
_chemical_formula_weight         152.14
_chemical_name_common            4-acetylresorcinol
_chemical_name_systematic
;
1-(2,4-dihydroxyphenyl)ethanone
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   6.7640(3)
_cell_length_b                   13.1193(6)
_cell_length_c                   23.9936(9)
_cell_measurement_reflns_used    13155
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      71.0026
_cell_measurement_theta_min      3.3641
_cell_volume                     2129.17(16)
_computing_cell_refinement
'CrysAlis RED (Version 1.171.32.15; Oxford Diffraction, 2008)'
_computing_data_collection
'CrysAlis CCD (Version 1.171.32.15; Oxford Diffraction, 2008)'
_computing_data_reduction
'CrysAlis RED (Version 1.171.32.15; Oxford Diffraction, (2008)'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean 8.3648
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Nova O'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0121
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20232
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         71.09
_diffrn_reflns_theta_min         3.84
_exptl_absorpt_coefficient_mu    0.922
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     276
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0660P)²+0.1332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0828
_reflns_number_gt                2185
_reflns_number_total             2327
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3292.cif
_cod_data_source_block           IO
_cod_database_code               2017136
_cod_database_fobs_code          2017136
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C11 0.3400(3) 0.40128(12) 0.20314(6) 0.0208(3) Uani d U 1 . .
C C12 0.3354(3) 0.46415(11) 0.24983(7) 0.0216(3) Uani d U 1 . .
H H12 0.3159 0.5355 0.2457 0.026 Uiso calc R 1 . .
C C13 0.3594(2) 0.42244(12) 0.30239(6) 0.0203(3) Uani d U 1 . .
C C14 0.3906(2) 0.31620(12) 0.30962(6) 0.0200(3) Uani d U 1 . .
C C15 0.3956(3) 0.25564(12) 0.26135(7) 0.0217(3) Uani d U 1 . .
H H15 0.4164 0.1843 0.2651 0.026 Uiso calc R 1 . .
C C16 0.3715(3) 0.29584(11) 0.20895(6) 0.0222(4) Uani d U 1 . .
H H16 0.3761 0.2530 0.1770 0.027 Uiso calc R 1 . .
C C17 0.4108(2) 0.27223(12) 0.36493(6) 0.0207(3) Uani d U 1 . .
C C18 0.4389(3) 0.15947(12) 0.37181(7) 0.0259(4) Uani d U 1 . .
H H18A 0.4588 0.1436 0.4113 0.039 Uiso calc R 1 . .
H H18B 0.5549 0.1375 0.3505 0.039 Uiso calc R 1 . .
H H18C 0.3214 0.1236 0.3581 0.039 Uiso calc R 1 . .
O O11 0.31297(19) 0.44485(9) 0.15300(5) 0.0258(3) Uani d U 1 . .
H H111 0.313(3) 0.3981(17) 0.1284(10) 0.035(6) Uiso d . 1 . .
O O12 0.3520(2) 0.48663(8) 0.34677(5) 0.0262(3) Uani d U 1 . .
H H112 0.368(4) 0.4509(19) 0.3773(12) 0.051(7) Uiso d . 1 . .
O O13 0.40316(19) 0.32726(9) 0.40723(5) 0.0260(3) Uani d U 1 . .
C C21 0.4359(3) 0.28363(12) 0.55851(7) 0.0205(3) Uani d U 1 . .
C C22 0.4373(3) 0.32412(12) 0.61192(7) 0.0214(3) Uani d U 1 . .
H H22 0.4549 0.3953 0.6172 0.026 Uiso calc R 1 . .
C C23 0.4131(2) 0.26072(11) 0.65741(6) 0.0198(3) Uani d U 1 . .
C C24 0.3873(2) 0.15368(11) 0.65035(6) 0.0188(3) Uani d U 1 . .
C C25 0.3838(3) 0.11589(12) 0.59548(6) 0.0213(3) Uani d U 1 . .
H H25 0.3646 0.0449 0.5897 0.026 Uiso calc R 1 . .
C C26 0.4074(3) 0.17867(12) 0.54997(6) 0.0221(3) Uani d U 1 . .
H H26 0.4044 0.1514 0.5133 0.027 Uiso calc R 1 . .
C C27 0.3664(2) 0.08772(12) 0.69875(7) 0.0209(3) Uani d U 1 . .
C C28 0.3508(3) -0.02619(12) 0.69194(7) 0.0273(4) Uani d U 1 . .
H H28A 0.3558 -0.0588 0.7287 0.041 Uiso calc R 1 . .
H H28B 0.4609 -0.0507 0.6691 0.041 Uiso calc R 1 . .
H H28C 0.2254 -0.0431 0.6737 0.041 Uiso calc R 1 . .
O O21 0.4635(2) 0.34990(8) 0.51629(5) 0.0273(3) Uani d U 1 . .
H H121 0.452(4) 0.317(2) 0.4864(11) 0.044(6) Uiso d . 1 . .
O O22 0.4129(2) 0.30461(9) 0.70836(5) 0.0256(3) Uani d U 1 . .
H H122 0.392(4) 0.255(2) 0.7314(11) 0.051(7) Uiso d . 1 . .
O O23 0.36192(19) 0.12502(9) 0.74660(4) 0.0249(3) Uani d U 1 . .
C C31 0.3192(3) 0.11514(12) 0.88848(6) 0.0198(3) Uani d U 1 . .
C C32 0.3163(3) 0.08269(11) 0.94379(6) 0.0207(3) Uani d U 1 . .
H H32 0.3178 0.0119 0.9522 0.025 Uiso calc R 1 . .
C C33 0.3112(2) 0.15340(12) 0.98649(6) 0.0194(3) Uani d U 1 . .
C C34 0.3090(3) 0.25978(12) 0.97507(6) 0.0187(3) Uani d U 1 . .
C C35 0.3095(3) 0.28943(12) 0.91848(6) 0.0211(3) Uani d U 1 . .
H H35 0.3064 0.3600 0.9097 0.025 Uiso calc R 1 . .
C C36 0.3144(3) 0.22004(12) 0.87595(6) 0.0217(3) Uani d U 1 . .
H H36 0.3146 0.2424 0.8383 0.026 Uiso calc R 1 . .
C C37 0.3087(2) 0.33376(12) 1.02014(7) 0.0202(3) Uani d U 1 . .
C C38 0.3085(3) 0.44614(11) 1.00702(7) 0.0245(4) Uani d U 1 . .
H H38A 0.3048 0.4852 1.0418 0.037 Uiso calc R 1 . .
H H38B 0.1919 0.4628 0.9845 0.037 Uiso calc R 1 . .
H H38C 0.4284 0.4635 0.9862 0.037 Uiso calc R 1 . .
O O31 0.32632(19) 0.04311(8) 0.84877(5) 0.0242(3) Uani d U 1 . .
H H131 0.328(4) 0.0703(18) 0.8167(11) 0.041(6) Uiso d . 1 . .
O O32 0.3096(2) 0.11749(9) 1.03946(4) 0.0249(3) Uani d U 1 . .
H H132 0.313(4) 0.171(2) 1.0595(11) 0.048(7) Uiso d . 1 . .
O O33 0.3097(2) 0.30534(8) 1.06971(4) 0.0235(3) Uani d U 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
O11 C11 C12 . . 117.74(13) ?
O11 C11 C16 . . 121.83(13) ?
C12 C11 C16 . . 120.44(14) ?
C13 C12 C11 . . 119.77(14) ?
O12 C13 C12 . . 117.68(13) ?
O12 C13 C14 . . 121.22(14) ?
C12 C13 C14 . . 121.10(14) ?
C15 C14 C13 . . 117.26(14) ?
C15 C14 C17 . . 121.73(13) ?
C13 C14 C17 . . 120.99(14) ?
C16 C15 C14 . . 122.33(14) ?
C15 C16 C11 . . 119.10(14) ?
O13 C17 C14 . . 120.63(14) ?
O13 C17 C18 . . 119.13(14) ?
C14 C17 C18 . . 120.23(14) ?
O21 C21 C22 . . 116.51(14) ?
O21 C21 C26 . . 122.77(15) ?
C22 C21 C26 . . 120.72(15) ?
C23 C22 C21 . . 119.89(14) ?
O22 C23 C22 . . 117.27(13) ?
O22 C23 C24 . . 121.82(14) ?
C22 C23 C24 . . 120.91(14) ?
C25 C24 C23 . . 117.41(14) ?
C25 C24 C27 . . 122.39(13) ?
C23 C24 C27 . . 120.20(14) ?
C26 C25 C24 . . 121.96(14) ?
C25 C26 C21 . . 119.09(14) ?
O23 C27 C24 . . 120.21(14) ?
O23 C27 C28 . . 119.13(14) ?
C24 C27 C28 . . 120.66(14) ?
O31 C31 C32 . . 117.45(13) ?
O31 C31 C36 . . 122.47(14) ?
C32 C31 C36 . . 120.08(14) ?
C33 C32 C31 . . 120.06(14) ?
O32 C33 C32 . . 117.50(13) ?
O32 C33 C34 . . 121.43(14) ?
C32 C33 C34 . . 121.06(14) ?
C35 C34 C33 . . 117.09(14) ?
C35 C34 C37 . . 122.10(14) ?
C33 C34 C37 . . 120.81(14) ?
C36 C35 C34 . . 122.27(14) ?
C35 C36 C31 . . 119.43(14) ?
O33 C37 C34 . . 120.68(14) ?
O33 C37 C38 . . 119.46(14) ?
C34 C37 C38 . . 119.87(14) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C16 C15 H15 . . 118.8 ?
C14 C15 H15 . . 118.8 ?
C15 C16 H16 . . 120.4 ?
C11 C16 H16 . . 120.4 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C11 O11 H111 . . 108.3(15) ?
C13 O12 H112 . . 108.6(17) ?
C23 C22 H22 . . 120.1 ?
C21 C22 H22 . . 120.1 ?
C26 C25 H25 . . 119.0 ?
C24 C25 H25 . . 119.0 ?
C25 C26 H26 . . 120.5 ?
C21 C26 H26 . . 120.5 ?
C27 C28 H28A . . 109.5 ?
C27 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C27 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C21 O21 H121 . . 107.3(17) ?
C23 O22 H122 . . 105.1(17) ?
C33 C32 H32 . . 120.0 ?
C31 C32 H32 . . 120.0 ?
C36 C35 H35 . . 118.9 ?
C34 C35 H35 . . 118.9 ?
C35 C36 H36 . . 120.3 ?
C31 C36 H36 . . 120.3 ?
C37 C38 H38A . . 109.5 ?
C37 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C37 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
C31 O31 H131 . . 110.4(16) ?
C33 O32 H132 . . 104.3(17) ?
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
C11 O11 . 1.3445(19) ?
C11 C12 . 1.392(2) ?
C11 C16 . 1.407(2) ?
C12 C13 . 1.384(2) ?
C13 O12 . 1.3584(19) ?
C13 C14 . 1.420(2) ?
C14 C15 . 1.405(2) ?
C14 C17 . 1.454(2) ?
C15 C16 . 1.373(2) ?
C17 O13 . 1.247(2) ?
C17 C18 . 1.501(2) ?
C21 O21 . 1.3480(19) ?
C21 C22 . 1.387(2) ?
C21 C26 . 1.405(2) ?
C22 C23 . 1.382(2) ?
C23 O22 . 1.3513(18) ?
C23 C24 . 1.425(2) ?
C24 C25 . 1.407(2) ?
C24 C27 . 1.455(2) ?
C25 C26 . 1.377(2) ?
C27 O23 . 1.2484(19) ?
C27 C28 . 1.507(2) ?
C31 O31 . 1.3427(19) ?
C31 C32 . 1.394(2) ?
C31 C36 . 1.409(2) ?
C32 C33 . 1.382(2) ?
C33 O32 . 1.3555(18) ?
C33 C34 . 1.422(2) ?
C34 C35 . 1.412(2) ?
C34 C37 . 1.453(2) ?
C35 C36 . 1.368(2) ?
C37 O33 . 1.246(2) ?
C37 C38 . 1.508(2) ?
C12 H12 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
O11 H111 . 0.85(2) ?
O12 H112 . 0.88(3) ?
C22 H22 . 0.9500 ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
C28 H28A . 0.9800 ?
C28 H28B . 0.9800 ?
C28 H28C . 0.9800 ?
O21 H121 . 0.84(3) ?
O22 H122 . 0.86(3) ?
C32 H32 . 0.9500 ?
C35 H35 . 0.9500 ?
C36 H36 . 0.9500 ?
C38 H38A . 0.9800 ?
C38 H38B . 0.9800 ?
C38 H38C . 0.9800 ?
O31 H131 . 0.85(3) ?
O32 H132 . 0.85(3) ?
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
O11 H111 O33 1_554 0.85(2) 1.86(2) 2.7101(16) 175(2)
O12 H112 O13 . 0.88(3) 1.79(3) 2.5682(16) 147(2)
O21 H121 O13 . 0.84(3) 1.93(3) 2.6650(16) 145(2)
O22 H122 O23 . 0.86(3) 1.76(3) 2.5519(16) 152(2)
O31 H131 O23 . 0.85(3) 1.84(3) 2.6875(15) 174(2)
O32 H132 O33 . 0.85(3) 1.79(3) 2.5691(15) 153(2)
C28 H28C O12 4_456 0.98 2.68 3.537(2) 146.7
C18 H18C O31 2_554 0.98 2.42 3.254(2) 143.2
C22 H22 O31 3_656 0.95 2.57 3.421(2) 148.8
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
O11 C11 C12 C13 . . . . 178.99(16) ?
C16 C11 C12 C13 . . . . -0.9(3) ?
C11 C12 C13 O12 . . . . -179.40(15) ?
C11 C12 C13 C14 . . . . 0.6(3) ?
O12 C13 C14 C15 . . . . 179.87(15) ?
C12 C13 C14 C15 . . . . -0.1(3) ?
O12 C13 C14 C17 . . . . 1.5(3) ?
C12 C13 C14 C17 . . . . -178.46(15) ?
C13 C14 C15 C16 . . . . -0.1(3) ?
C17 C14 C15 C16 . . . . 178.28(16) ?
C14 C15 C16 C11 . . . . -0.2(3) ?
O11 C11 C16 C15 . . . . -179.15(15) ?
C12 C11 C16 C15 . . . . 0.7(3) ?
C15 C14 C17 O13 . . . . -178.99(16) ?
C13 C14 C17 O13 . . . . -0.7(3) ?
C15 C14 C17 C18 . . . . 0.3(2) ?
C13 C14 C17 C18 . . . . 178.56(16) ?
O21 C21 C22 C23 . . . . -178.99(15) ?
C26 C21 C22 C23 . . . . 0.8(3) ?
C21 C22 C23 O22 . . . . -179.05(15) ?
C21 C22 C23 C24 . . . . 0.2(3) ?
O22 C23 C24 C25 . . . . 178.11(15) ?
C22 C23 C24 C25 . . . . -1.2(2) ?
O22 C23 C24 C27 . . . . -2.1(3) ?
C22 C23 C24 C27 . . . . 178.63(15) ?
C23 C24 C25 C26 . . . . 1.0(3) ?
C27 C24 C25 C26 . . . . -178.77(16) ?
C24 C25 C26 C21 . . . . 0.0(3) ?
O21 C21 C26 C25 . . . . 178.83(15) ?
C22 C21 C26 C25 . . . . -1.0(3) ?
C25 C24 C27 O23 . . . . -176.94(16) ?
C23 C24 C27 O23 . . . . 3.3(2) ?
C25 C24 C27 C28 . . . . 3.3(3) ?
C23 C24 C27 C28 . . . . -176.47(16) ?
O31 C31 C32 C33 . . . . 179.27(15) ?
C36 C31 C32 C33 . . . . -0.8(3) ?
C31 C32 C33 O32 . . . . -179.65(16) ?
C31 C32 C33 C34 . . . . -0.1(3) ?
O32 C33 C34 C35 . . . . -179.58(15) ?
C32 C33 C34 C35 . . . . 0.8(3) ?
O32 C33 C34 C37 . . . . 1.1(3) ?
C32 C33 C34 C37 . . . . -178.44(15) ?
C33 C34 C35 C36 . . . . -0.8(3) ?
C37 C34 C35 C36 . . . . 178.47(16) ?
C34 C35 C36 C31 . . . . 0.0(3) ?
O31 C31 C36 C35 . . . . -179.24(15) ?
C32 C31 C36 C35 . . . . 0.8(3) ?
C35 C34 C37 O33 . . . . -179.47(15) ?
C33 C34 C37 O33 . . . . -0.2(3) ?
C35 C34 C37 C38 . . . . 0.1(3) ?
C33 C34 C37 C38 . . . . 179.39(16) ?
