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#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/81/2228174.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228174
loop_
_publ_author_name
'Torre-Fernández, Laura'
'Suero, Marcos G.'
'García-Granda, Santiago'
_publ_section_title
;
 5-Hydroxy-7-phenyl-5-(prop-2-yn-1-yl)-5,6-dihydro-1-benzofuran-2(4H)-one
 monohydrate
;
_journal_coeditor_code           ZQ2046
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2834
_journal_paper_doi               10.1107/S1600536810028400
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H14 O3, H2 O'
_chemical_formula_moiety         'C17 H14 O3, H2 O'
_chemical_formula_sum            'C17 H16 O4'
_chemical_formula_weight         284.30
_chemical_name_systematic
;
5-Hydroxy-7-phenyl-5-(prop-2-yn-1-yl)-5,6-dihydro-1-benzofuran-2(4H)-one
monohydrate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 91.145(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1585(2)
_cell_length_b                   9.2160(3)
_cell_length_c                   17.4628(5)
_cell_measurement_reflns_used    3327
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      1.00
_cell_volume                     1473.65(7)
_computing_cell_refinement       '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 (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'Enraf--Nonius FR590'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5821
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   '(XABS2; Parkin et al., 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.690
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3360
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0526
_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)+(0.1074P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1905
_reflns_number_gt                2251
_reflns_number_total             3360
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zq2046.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228174
_cod_database_fobs_code          2228174
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_disorder_assembly
_atom_site_disorder_group
O O10 0.09705(15) -0.35189(15) 0.55947(8) 0.0309(4) Uani d . 1 . .
H H10 0.0938 -0.3890 0.5168 0.046 Uiso calc R 1 . .
O O21 0.07886(17) -0.41878(17) 0.40700(9) 0.0371(4) Uani d GD 1 . .
H H21A 0.0106 -0.5029 0.4127 0.108(13) Uiso d GD 1 . .
H H21B 0.0326 -0.3487 0.3699 0.080(10) Uiso d GD 1 . .
O O1 0.15674(17) 0.09639(15) 0.59615(7) 0.0299(4) Uani d . 1 . .
O O14 0.0447(2) 0.21621(17) 0.69040(8) 0.0424(5) Uani d . 1 . .
C C16 0.2016(2) 0.0987(2) 0.42937(12) 0.0332(5) Uani d . 1 . .
H H16 0.1281 0.1288 0.4617 0.040 Uiso calc R 1 . .
C C5 0.2133(2) -0.0433(2) 0.58766(11) 0.0257(5) Uani d . 1 . .
C C9 0.2434(2) -0.2746(2) 0.66557(11) 0.0283(5) Uani d . 1 . .
H H9A 0.1778 -0.3283 0.6981 0.034 Uiso calc R 1 . .
H H9B 0.3403 -0.2774 0.6889 0.034 Uiso calc R 1 . .
C C11 0.3067(2) -0.4999(2) 0.58931(12) 0.0334(5) Uani d . 1 . .
H H11A 0.2479 -0.5566 0.6239 0.040 Uiso calc R 1 . .
H H11B 0.2965 -0.5428 0.5388 0.040 Uiso calc R 1 . .
C C8 0.2462(2) -0.3443(2) 0.58623(11) 0.0267(5) Uani d . 1 . .
C C2 0.1017(3) 0.1045(2) 0.66926(11) 0.0319(5) Uani d . 1 . .
C C12 0.4598(3) -0.5102(2) 0.61430(12) 0.0327(5) Uani d . 1 . .
C C4 0.1930(2) -0.1211(2) 0.65843(10) 0.0260(5) Uani d . 1 . .
C C6 0.2752(2) -0.0953(2) 0.52416(11) 0.0244(5) Uani d . 1 . .
C C17 0.2193(3) 0.1677(3) 0.35963(12) 0.0408(6) Uani d . 1 . .
H H17 0.1571 0.2432 0.3454 0.049 Uiso calc R 1 . .
C C7 0.3324(2) -0.2498(2) 0.53073(11) 0.0281(5) Uani d . 1 . .
H H7A 0.4338 -0.2469 0.5478 0.034 Uiso calc R 1 . .
H H7B 0.3288 -0.2945 0.4804 0.034 Uiso calc R 1 . .
C C15 0.2936(2) -0.0165(2) 0.45162(11) 0.0264(5) Uani d . 1 . .
C C20 0.4029(2) -0.0591(2) 0.40115(11) 0.0325(5) Uani d . 1 . .
H H20 0.4645 -0.1357 0.4143 0.039 Uiso calc R 1 . .
C C3 0.1265(2) -0.0318(2) 0.70729(11) 0.0308(5) Uani d . 1 . .
H H3 0.1009 -0.0542 0.7572 0.037 Uiso calc R 1 . .
C C19 0.4203(3) 0.0118(3) 0.33181(13) 0.0391(6) Uani d . 1 . .
H H19 0.4938 -0.0171 0.2991 0.047 Uiso calc R 1 . .
C C18 0.3288(3) 0.1249(3) 0.31113(12) 0.0412(6) Uani d . 1 . .
H H18 0.3409 0.1723 0.2647 0.049 Uiso calc R 1 . .
C C13 0.5838(3) -0.5168(3) 0.63321(14) 0.0429(6) Uani d . 1 . .
H H13 0.6818 -0.5221 0.6481 0.051 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 O10 H10 . . 109.5 ?
H21A O21 H21B . . 107.9 ?
C2 O1 C5 . . 106.88(15) ?
C17 C16 C15 . . 120.6(2) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C6 C5 O1 . . 125.43(18) ?
C6 C5 C4 . . 126.35(19) ?
O1 C5 C4 . . 108.21(16) ?
C4 C9 C8 . . 109.49(16) ?
C4 C9 H9A . . 109.8 ?
C8 C9 H9A . . 109.8 ?
C4 C9 H9B . . 109.8 ?
C8 C9 H9B . . 109.8 ?
H9A C9 H9B . . 108.2 ?
C12 C11 C8 . . 114.41(18) ?
C12 C11 H11A . . 108.7 ?
C8 C11 H11A . . 108.7 ?
C12 C11 H11B . . 108.7 ?
C8 C11 H11B . . 108.7 ?
H11A C11 H11B . . 107.6 ?
O10 C8 C9 . . 106.40(16) ?
O10 C8 C7 . . 108.67(15) ?
C9 C8 C7 . . 110.64(17) ?
O10 C8 C11 . . 107.82(16) ?
C9 C8 C11 . . 111.90(16) ?
C7 C8 C11 . . 111.21(17) ?
O14 C2 O1 . . 119.52(19) ?
O14 C2 C3 . . 131.7(2) ?
O1 C2 C3 . . 108.78(17) ?
C13 C12 C11 . . 178.7(2) ?
C3 C4 C5 . . 107.93(18) ?
C3 C4 C9 . . 132.25(18) ?
C5 C4 C9 . . 119.83(17) ?
C5 C6 C15 . . 126.24(19) ?
C5 C6 C7 . . 114.96(17) ?
C15 C6 C7 . . 118.79(16) ?
C18 C17 C16 . . 120.4(2) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C6 C7 C8 . . 113.49(16) ?
C6 C7 H7A . . 108.9 ?
C8 C7 H7A . . 108.9 ?
C6 C7 H7B . . 108.9 ?
C8 C7 H7B . . 108.9 ?
H7A C7 H7B . . 107.7 ?
C20 C15 C16 . . 117.96(19) ?
C20 C15 C6 . . 119.86(19) ?
C16 C15 C6 . . 122.15(19) ?
C19 C20 C15 . . 120.8(2) ?
C19 C20 H20 . . 119.6 ?
C15 C20 H20 . . 119.6 ?
C4 C3 C2 . . 108.20(18) ?
C4 C3 H3 . . 125.9 ?
C2 C3 H3 . . 125.9 ?
C18 C19 C20 . . 120.3(2) ?
C18 C19 H19 . . 119.9 ?
C20 C19 H19 . . 119.9 ?
C19 C18 C17 . . 119.9(2) ?
C19 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C12 C13 H13 . . 180.0 ?
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
O10 C8 . 1.436(2) ?
O10 H10 . 0.8200 ?
O21 H21A . 1.0020 ?
O21 H21B . 1.0021 ?
O1 C2 . 1.384(2) ?
O1 C5 . 1.397(2) ?
O14 C2 . 1.215(3) ?
C16 C17 . 1.386(3) ?
C16 C15 . 1.405(3) ?
C16 H16 . 0.9300 ?
C5 C6 . 1.344(3) ?
C5 C4 . 1.444(3) ?
C9 C4 . 1.492(3) ?
C9 C8 . 1.528(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C11 C12 . 1.463(3) ?
C11 C8 . 1.538(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C8 C7 . 1.533(3) ?
C2 C3 . 1.437(3) ?
C12 C13 . 1.179(3) ?
C4 C3 . 1.341(3) ?
C6 C15 . 1.473(3) ?
C6 C7 . 1.521(3) ?
C17 C18 . 1.383(4) ?
C17 H17 . 0.9300 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C15 C20 . 1.403(3) ?
C20 C19 . 1.387(3) ?
C20 H20 . 0.9300 ?
C3 H3 . 0.9300 ?
C19 C18 . 1.381(3) ?
C19 H19 . 0.9300 ?
C18 H18 . 0.9300 ?
C13 H13 . 0.9300 ?
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
O10 H10 O21 . 0.82 1.94 2.735(2) 163.4
O21 H21A O10 3_546 1.00 1.74 2.728(2) 169.2
O21 H21B O14 3_556 1.00 1.75 2.754(2) 176.0
C13 H13 O21 3_646 0.93 2.47 3.236(3) 139.4
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
C2 O1 C5 C6 . . . . 179.1(2) ?
C2 O1 C5 C4 . . . . -0.7(2) ?
C4 C9 C8 O10 . . . . -66.2(2) ?
C4 C9 C8 C7 . . . . 51.7(2) ?
C4 C9 C8 C11 . . . . 176.32(17) ?
C12 C11 C8 O10 . . . . 178.87(16) ?
C12 C11 C8 C9 . . . . -64.5(2) ?
C12 C11 C8 C7 . . . . 59.8(2) ?
C5 O1 C2 O14 . . . . -179.3(2) ?
C5 O1 C2 C3 . . . . 0.9(2) ?
C6 C5 C4 C3 . . . . -179.6(2) ?
O1 C5 C4 C3 . . . . 0.2(2) ?
C6 C5 C4 C9 . . . . 0.0(3) ?
O1 C5 C4 C9 . . . . 179.82(17) ?
C8 C9 C4 C3 . . . . 154.0(2) ?
C8 C9 C4 C5 . . . . -25.5(3) ?
O1 C5 C6 C15 . . . . -0.8(3) ?
C4 C5 C6 C15 . . . . 179.0(2) ?
O1 C5 C6 C7 . . . . 178.16(18) ?
C4 C5 C6 C7 . . . . -2.1(3) ?
C15 C16 C17 C18 . . . . -0.5(4) ?
C5 C6 C7 C8 . . . . 30.3(3) ?
C15 C6 C7 C8 . . . . -150.71(18) ?
O10 C8 C7 C6 . . . . 60.3(2) ?
C9 C8 C7 C6 . . . . -56.2(2) ?
C11 C8 C7 C6 . . . . 178.83(16) ?
C17 C16 C15 C20 . . . . -0.2(3) ?
C17 C16 C15 C6 . . . . -178.1(2) ?
C5 C6 C15 C20 . . . . 156.6(2) ?
C7 C6 C15 C20 . . . . -22.3(3) ?
C5 C6 C15 C16 . . . . -25.5(3) ?
C7 C6 C15 C16 . . . . 155.6(2) ?
C16 C15 C20 C19 . . . . 0.7(3) ?
C6 C15 C20 C19 . . . . 178.67(19) ?
C5 C4 C3 C2 . . . . 0.3(2) ?
C9 C4 C3 C2 . . . . -179.2(2) ?
O14 C2 C3 C4 . . . . 179.5(2) ?
O1 C2 C3 C4 . . . . -0.8(2) ?
C15 C20 C19 C18 . . . . -0.6(3) ?
C20 C19 C18 C17 . . . . -0.1(4) ?
C16 C17 C18 C19 . . . . 0.7(4) ?
