#------------------------------------------------------------------------------
#$Date: 2016-09-06 13:40:16 +0300 (Tue, 06 Sep 2016) $
#$Revision: 186181 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/18/2241839.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_2241839
loop_
_publ_author_name
'Hübscher, Jörg'
'Rosin, Robert'
'Seichter, Wilhelm'
'Weber, Edwin'
_publ_section_title
;
 Crystal structures of 2-acetyl-4-ethynylphenol and
 2-acetyl-4-(3-hydroxy-3,3-dimethyl-1-propynyl)phenol
;
_journal_coeditor_code           SU5317
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1370
_journal_page_last               1373
_journal_paper_doi               10.1107/S2056989016013451
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C10 H8 O2'
_chemical_formula_moiety         'C10 H8 O2'
_chemical_formula_sum            'C10 H8 O2'
_chemical_formula_weight         160.16
_chemical_name_systematic
;
2-Acetyl-4-ethynylphenol
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                69.2410(10)
_cell_angle_beta                 79.9750(10)
_cell_angle_gamma                70.1270(10)
_cell_formula_units_Z            2
_cell_length_a                   6.97250(10)
_cell_length_b                   7.31740(10)
_cell_length_c                   8.9189(2)
_cell_measurement_reflns_used    4876
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      33.32
_cell_measurement_theta_min      2.45
_cell_volume                     399.422(12)
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.098
_diffrn_reflns_theta_min         2.447
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       irregular
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.186
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         2133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0380
_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)+(0.0597P)²+0.0965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1154
_reflns_number_gt                1881
_reflns_number_total             2133
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su5317sup1.cif
_cod_data_source_block           I
_cod_database_code               2241839
_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   0.956
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           .2013
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 1.41916(10) 0.74175(12) 0.41955(9) 0.0302(2) Uani d 1
H H1 1.3947 0.7603 0.3254 0.045 Uiso calc 1
O O2 1.20310(12) 0.78960(13) 0.19487(9) 0.0330(2) Uani d 1
C C1 1.24964(13) 0.73237(14) 0.51663(11) 0.0216(2) Uani d 1
C C2 1.06267(13) 0.75622(13) 0.45971(10) 0.01892(19) Uani d 1
C C3 0.89112(13) 0.75319(13) 0.56854(10) 0.01892(19) Uani d 1
H H3 0.7646 0.7693 0.5317 0.023 Uiso calc 1
C C4 0.90292(13) 0.72710(13) 0.72934(11) 0.01990(19) Uani d 1
C C5 1.09230(14) 0.69865(14) 0.78338(11) 0.0229(2) Uani d 1
H H5 1.1027 0.6783 0.8933 0.027 Uiso calc 1
C C6 1.26244(14) 0.70005(15) 0.67882(12) 0.0245(2) Uani d 1
H H6 1.3895 0.6788 0.7174 0.029 Uiso calc 1
C C7 1.04995(14) 0.78735(14) 0.28831(11) 0.0219(2) Uani d 1
C C8 0.85185(15) 0.81574(16) 0.22710(11) 0.0260(2) Uani d 1
H H8A 0.8665 0.8497 0.1099 0.039 Uiso calc 1
H H8B 0.7450 0.9274 0.2564 0.039 Uiso calc 1
H H8C 0.8142 0.6887 0.2748 0.039 Uiso calc 1
C C9 0.72595(14) 0.73051(15) 0.83939(11) 0.0233(2) Uani d 1
C C10 0.58198(16) 0.73495(18) 0.93333(12) 0.0303(2) Uani d 1
H H10 0.4670 0.7385 1.0084 0.036 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
C1 O1 H1 109.5
O1 C1 C6 117.45(8)
O1 C1 C2 122.56(8)
C6 C1 C2 119.99(8)
C3 C2 C1 118.61(8)
C3 C2 C7 121.40(8)
C1 C2 C7 119.98(8)
C4 C3 C2 121.23(8)
C4 C3 H3 119.4
C2 C3 H3 119.4
C3 C4 C5 118.87(8)
C3 C4 C9 121.18(8)
C5 C4 C9 119.94(8)
C6 C5 C4 120.77(8)
C6 C5 H5 119.6
C4 C5 H5 119.6
C5 C6 C1 120.47(8)
C5 C6 H6 119.8
C1 C6 H6 119.8
O2 C7 C2 120.17(8)
O2 C7 C8 119.66(8)
C2 C7 C8 120.17(8)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C10 C9 C4 178.07(10)
C9 C10 H10 180.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3447(10)
O1 H1 0.8400
O2 C7 1.2359(11)
C1 C6 1.3945(13)
C1 C2 1.4144(12)
C2 C3 1.4043(11)
C2 C7 1.4776(12)
C3 C4 1.3915(12)
C3 H3 0.9500
C4 C5 1.4081(13)
C4 C9 1.4357(12)
C5 C6 1.3760(13)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.4954(13)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C10 1.1896(14)
C10 H10 0.9500
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 . 0.84 1.83 2.5696(11) 146
C10 H10 O2 1_456 0.95 2.28 3.2214(14) 171
C8 H8C Cg1 2_786 0.97 2.72 3.6024(12) 150
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 -177.21(8)
C6 C1 C2 C3 2.03(13)
O1 C1 C2 C7 1.68(14)
C6 C1 C2 C7 -179.08(8)
C1 C2 C3 C4 -0.09(13)
C7 C2 C3 C4 -178.96(8)
C2 C3 C4 C5 -1.46(13)
C2 C3 C4 C9 178.01(8)
C3 C4 C5 C6 1.11(14)
C9 C4 C5 C6 -178.37(8)
C4 C5 C6 C1 0.82(14)
O1 C1 C6 C5 176.86(8)
C2 C1 C6 C5 -2.41(14)
C3 C2 C7 O2 179.92(8)
C1 C2 C7 O2 1.07(14)
C3 C2 C7 C8 -0.24(13)
C1 C2 C7 C8 -179.09(8)

_cod_database_fobs_code 2241839
