##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2013-11-18
_journal_date_accepted     2013-11-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      1
_journal_page_first     o24
_journal_page_last     o24
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813032613
_journal_coeditor_code     SU2668
_publ_contact_author_name     'M.A. Neelakantan'
_publ_contact_author_address
;
   Chemistry Research Centre
   National Engineering College
   K.R. Nagar
   Kovilpatti 628 503
   India
;
_publ_contact_author_email     'drmaneelakantan@gmail.com'
_publ_contact_author_fax     '044 091 2499 3057'
_publ_contact_author_phone     '044 091 24484170'
_publ_section_title
;
1-[2-Hydroxy-4-(prop-2-yn-1-yloxy)phenyl]ethanone
;
loop_
    _publ_author_name
    _publ_author_address
    'V. Selvarani'
;
   Chemistry Research Centre
   National Engineering College
   K.R. Nagar
   Kovilpatti 628 503
   India
;
    'M. A. Neelakantan'
;
   Chemistry Research Centre
   National Engineering College
   K.R. Nagar
   Kovilpatti 628 503
   India
;
    'T. Srinivasan'
;
    Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai 600 025
    India
;
    'D. Velmurugan'
;
    Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai 600 025
    India
;
data_I
_database_code_depnum_ccdc_archive 'CCDC 966316'
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-[2-Hydroxy-4-(prop-2-yn-1-yloxy)phenyl]ethan-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H10 O3'
_chemical_formula_sum     'C11 H10 O3'
_chemical_formula_iupac     'C11 H10 O3'
_chemical_formula_weight     190.19
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     4.9975(2)
_cell_length_b     10.4305(4)
_cell_length_c     18.8467(7)
_cell_angle_alpha     90.00
_cell_angle_beta     97.257(2)
_cell_angle_gamma     90.00
_cell_volume     974.54(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2451
_cell_measurement_theta_min     2.18
_cell_measurement_theta_max     28.44
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.296
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     400
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.9677
_exptl_absorpt_correction_T_max     0.9813
_exptl_special_details     ?
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEXII area-detector'
_diffrn_measurement_method     'ω and φ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9316
_diffrn_reflns_av_R_equivalents     0.0205
_diffrn_reflns_av_sigmaI/netI     0.0176
_diffrn_reflns_theta_min     2.18
_diffrn_reflns_theta_max     28.44
_diffrn_reflns_theta_full     28.44
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -25
_diffrn_reflns_limit_l_max     25
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2451
_reflns_number_gt     1898
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0567
_refine_ls_R_factor_gt     0.0429
_refine_ls_wR_factor_gt     0.1175
_refine_ls_wR_factor_ref     0.1298
_refine_ls_goodness_of_fit_ref     1.047
_refine_ls_restrained_S_all     1.046
_refine_ls_number_reflns     2451
_refine_ls_number_parameters     138
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0637P)²+0.1394P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.172
_refine_diff_density_min     -0.205
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.020(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
 'ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.9425(3) 0.69719(11) 0.08613(7) 0.0455(3) Uani d . 1 1 . .
    C C2 0.9120(2) 0.81055(10) 0.12463(6) 0.0421(3) Uani d . 1 1 . .
    C C3 1.0579(3) 0.91806(11) 0.10720(6) 0.0475(3) Uani d . 1 1 . .
    H H3 1.0417 0.9941 0.1320 0.057 Uiso calc R 1 1 . .
    C C4 1.2229(3) 0.91474(11) 0.05494(7) 0.0506(3) Uani d . 1 1 . .
    H H4 1.3186 0.9874 0.0446 0.061 Uiso calc R 1 1 . .
    C C5 1.2467(3) 0.80135(11) 0.01728(6) 0.0446(3) Uani d . 1 1 . .
    C C6 1.1094(3) 0.69245(11) 0.03266(6) 0.0468(3) Uani d . 1 1 . .
    H H6 1.1283 0.6169 0.0076 0.056 Uiso calc R 1 1 . .
    C C7 0.7340(3) 0.81464(12) 0.18017(6) 0.0485(3) Uani d . 1 1 . .
    C C8 0.7041(4) 0.93600(15) 0.22030(9) 0.0632(4) Uani d D 1 1 . .
    H H8A 0.595(4) 0.9292(18) 0.2554(11) 0.095 Uiso d D 1 1 . .
    H H8B 0.648(4) 1.005(2) 0.1896(10) 0.095 Uiso d D 1 1 . .
    H H8C 0.872(4) 0.9636(19) 0.2446(10) 0.095 Uiso d D 1 1 . .
    C C9 1.4462(3) 0.69606(12) -0.07557(7) 0.0527(3) Uani d . 1 1 . .
    H H9A 1.2727 0.6639 -0.0972 0.063 Uiso calc R 1 1 . .
    H H9B 1.5342 0.6298 -0.0449 0.063 Uiso calc R 1 1 . .
    C C10 1.6120(3) 0.73056(13) -0.13064(7) 0.0546(3) Uani d . 1 1 . .
    C C11 1.7405(3) 0.75594(16) -0.17657(8) 0.0680(4) Uani d . 1 1 . .
    H H11 1.8424 0.7761 -0.2130 0.082 Uiso calc R 1 1 . .
    O O1 0.8072(2) 0.58946(8) 0.09853(6) 0.0691(4) Uani d . 1 1 . .
    H H1 0.7187 0.6017 0.1317 0.104 Uiso calc R 1 1 . .
    O O2 0.6074(2) 0.71799(10) 0.19459(5) 0.0624(3) Uani d . 1 1 . .
    O O3 1.4107(2) 0.80891(8) -0.03494(5) 0.0574(3) Uani d . 1 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    C1 O1 . 1.3469(14) ?
    C1 C6 . 1.3879(16) ?
    C1 C2 . 1.4056(16) ?
    C2 C3 . 1.3991(16) ?
    C2 C7 . 1.4573(16) ?
    C3 C4 . 1.3627(17) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.3920(16) ?
    C4 H4 . 0.9300 ?
    C5 O3 . 1.3602(14) ?
    C5 C6 . 1.3765(16) ?
    C6 H6 . 0.9300 ?
    C7 O2 . 1.2384(15) ?
    C7 C8 . 1.4918(18) ?
    C8 H8A . 0.91(2) ?
    C8 H8B . 0.94(2) ?
    C8 H8C . 0.95(2) ?
    C9 O3 . 1.4275(14) ?
    C9 C10 . 1.4529(18) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 C11 . 1.1712(19) ?
    C11 H11 . 0.9300 ?
    O1 H1 . 0.8200 ?
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
    O1 C1 C6 . . 117.20(10) ?
    O1 C1 C2 . . 121.51(11) ?
    C6 C1 C2 . . 121.27(10) ?
    C3 C2 C1 . . 117.34(11) ?
    C3 C2 C7 . . 121.92(10) ?
    C1 C2 C7 . . 120.75(10) ?
    C4 C3 C2 . . 122.03(10) ?
    C4 C3 H3 . . 119.0 ?
    C2 C3 H3 . . 119.0 ?
    C3 C4 C5 . . 119.24(10) ?
    C3 C4 H4 . . 120.4 ?
    C5 C4 H4 . . 120.4 ?
    O3 C5 C6 . . 124.19(10) ?
    O3 C5 C4 . . 114.68(10) ?
    C6 C5 C4 . . 121.13(10) ?
    C5 C6 C1 . . 118.99(10) ?
    C5 C6 H6 . . 120.5 ?
    C1 C6 H6 . . 120.5 ?
    O2 C7 C2 . . 120.59(11) ?
    O2 C7 C8 . . 119.53(12) ?
    C2 C7 C8 . . 119.89(11) ?
    C7 C8 H8A . . 114.1(12) ?
    C7 C8 H8B . . 112.2(12) ?
    H8A C8 H8B . . 110.2(17) ?
    C7 C8 H8C . . 111.3(12) ?
    H8A C8 H8C . . 104.4(16) ?
    H8B C8 H8C . . 103.9(17) ?
    O3 C9 C10 . . 107.45(10) ?
    O3 C9 H9A . . 110.2 ?
    C10 C9 H9A . . 110.2 ?
    O3 C9 H9B . . 110.2 ?
    C10 C9 H9B . . 110.2 ?
    H9A C9 H9B . . 108.5 ?
    C11 C10 C9 . . 177.83(15) ?
    C10 C11 H11 . . 180.0 ?
    C1 O1 H1 . . 109.5 ?
    C5 O3 C9 . . 117.87(9) ?
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
    O1 C1 C2 C3 . . . . -179.06(12) ?
    C6 C1 C2 C3 . . . . -0.40(19) ?
    O1 C1 C2 C7 . . . . 0.7(2) ?
    C6 C1 C2 C7 . . . . 179.39(12) ?
    C1 C2 C3 C4 . . . . 0.3(2) ?
    C7 C2 C3 C4 . . . . -179.52(12) ?
    C2 C3 C4 C5 . . . . 0.4(2) ?
    C3 C4 C5 O3 . . . . 178.37(12) ?
    C3 C4 C5 C6 . . . . -0.9(2) ?
    O3 C5 C6 C1 . . . . -178.44(12) ?
    C4 C5 C6 C1 . . . . 0.8(2) ?
    O1 C1 C6 C5 . . . . 178.60(12) ?
    C2 C1 C6 C5 . . . . -0.1(2) ?
    C3 C2 C7 O2 . . . . -179.90(12) ?
    C1 C2 C7 O2 . . . . 0.3(2) ?
    C3 C2 C7 C8 . . . . -0.1(2) ?
    C1 C2 C7 C8 . . . . -179.89(13) ?
    C6 C5 O3 C9 . . . . -1.1(2) ?
    C4 C5 O3 C9 . . . . 179.62(12) ?
    C10 C9 O3 C5 . . . . 175.97(12) ?
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 . 0.82 1.83 2.5551(14) 146
    C4 H4 O3 3_875 0.93 2.54 3.4609(16) 172
    C11 H11 O2 4_775 0.93 2.32 3.2337(18) 168
