#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/97/2229755.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_2229755
loop_
_publ_author_name
'Yousuf, S.'
'Musharraf, S. G.'
'Khan, I.'
Samiullah
'Fun, Hoong-Kun'
_publ_section_title
;
 Absolute configuration of (2S)-4-(4-hydroxyphenyl)butan-2-ol
;
_journal_coeditor_code           LH5221
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o952
_journal_paper_doi               10.1107/S1600536811010026
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H14 O2'
_chemical_formula_moiety         'C10 H14 O2'
_chemical_formula_sum            'C10 H14 O2'
_chemical_formula_weight         166.21
_chemical_name_common            (+)-rhododendrol
_chemical_name_systematic
;
(2S)-4-(4-hydroxyphenyl)butan-2-ol
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.216(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.2342(2)
_cell_length_b                   6.3815(2)
_cell_length_c                   9.9419(4)
_cell_measurement_reflns_used    3477
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.26
_cell_measurement_theta_min      6.12
_cell_volume                     458.63(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type
;
Bruker SMART APEXII DUO CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4954
_diffrn_reflns_theta_full        67.49
_diffrn_reflns_theta_max         67.49
_diffrn_reflns_theta_min         6.12
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  0.9658
_exptl_absorpt_correction_T_min  0.7844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            Colorles
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             180
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.235
_refine_ls_abs_structure_details 'Flack (1983), 579 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.03(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1455
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0290
_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)+(0.0499P)²+0.0461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0750
_reflns_number_gt                1446
_reflns_number_total             1455
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5221.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2229755
_cod_database_fobs_code          2229755
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
O O1 0.33418(12) 0.03888(15) 0.11761(9) 0.0200(2) Uani d . 1 . .
O O2 0.33463(12) 0.33901(17) 0.93717(9) 0.0214(2) Uani d . 1 . .
C C1 0.22229(17) 0.3267(2) 0.42530(13) 0.0191(3) Uani d . 1 . .
C C2 0.25737(17) 0.2886(2) 0.29010(14) 0.0184(3) Uani d . 1 . .
C C3 0.29911(15) 0.08712(19) 0.24875(13) 0.0161(3) Uani d . 1 . .
C C4 0.30875(17) -0.0757(2) 0.34234(14) 0.0191(3) Uani d . 1 . .
C C5 0.27631(16) -0.0347(2) 0.47664(13) 0.0187(3) Uani d . 1 . .
C C6 0.23165(16) 0.1659(2) 0.52052(13) 0.0173(3) Uani d . 1 . .
C C7 0.19572(19) 0.2007(2) 0.66828(14) 0.0222(3) Uani d . 1 . .
C C8 0.20129(16) 0.4288(2) 0.71453(13) 0.0179(3) Uani d . 1 . .
C C9 0.18659(17) 0.4510(2) 0.86638(13) 0.0202(3) Uani d . 1 . .
C C10 0.1875(2) 0.6786(3) 0.91038(16) 0.0286(4) Uani d . 1 . .
H H1 0.192(2) 0.463(3) 0.4534(16) 0.019(4) Uiso d . 1 . .
H H2 0.245(2) 0.401(3) 0.2254(19) 0.026(4) Uiso d . 1 . .
H H4 0.339(2) -0.216(3) 0.3145(17) 0.024(4) Uiso d . 1 . .
H H5 0.281(2) -0.143(3) 0.5411(18) 0.025(4) Uiso d . 1 . .
H H7A 0.076(2) 0.136(3) 0.6896(18) 0.027(4) Uiso d . 1 . .
H H7B 0.293(3) 0.123(3) 0.720(2) 0.032(5) Uiso d . 1 . .
H H8A 0.103(3) 0.501(3) 0.6728(18) 0.026(4) Uiso d . 1 . .
H H8B 0.322(2) 0.494(3) 0.6865(15) 0.013(4) Uiso d . 1 . .
H H9 0.078(2) 0.383(3) 0.8913(17) 0.020(4) Uiso d . 1 . .
H H10A 0.075(3) 0.755(4) 0.873(2) 0.044(6) Uiso d . 1 . .
H H10B 0.304(2) 0.749(3) 0.8792(17) 0.021(4) Uiso d . 1 . .
H H10C 0.183(3) 0.691(3) 1.011(2) 0.040(5) Uiso d . 1 . .
H H1O1 0.319(3) 0.151(4) 0.062(2) 0.043(6) Uiso d . 1 . .
H H1O2 0.444(3) 0.400(3) 0.920(2) 0.036(5) Uiso d . 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
C3 O1 H1O1 . . 112.1(15) ?
C9 O2 H1O2 . . 109.6(13) ?
C6 C1 C2 . . 121.21(12) ?
C6 C1 H1 . . 118.9(10) ?
C2 C1 H1 . . 119.9(10) ?
C3 C2 C1 . . 119.72(12) ?
C3 C2 H2 . . 120.5(11) ?
C1 C2 H2 . . 119.7(11) ?
O1 C3 C2 . . 122.67(11) ?
O1 C3 C4 . . 117.40(11) ?
C2 C3 C4 . . 119.93(11) ?
C5 C4 C3 . . 119.64(12) ?
C5 C4 H4 . . 119.9(11) ?
C3 C4 H4 . . 120.4(11) ?
C4 C5 C6 . . 121.57(12) ?
C4 C5 H5 . . 120.8(12) ?
C6 C5 H5 . . 117.6(12) ?
C5 C6 C1 . . 117.92(12) ?
C5 C6 C7 . . 119.18(11) ?
C1 C6 C7 . . 122.90(12) ?
C6 C7 C8 . . 115.31(11) ?
C6 C7 H7A . . 109.3(11) ?
C8 C7 H7A . . 110.2(11) ?
C6 C7 H7B . . 106.5(12) ?
C8 C7 H7B . . 108.1(12) ?
H7A C7 H7B . . 107.0(15) ?
C9 C8 C7 . . 112.65(11) ?
C9 C8 H8A . . 108.3(11) ?
C7 C8 H8A . . 109.0(12) ?
C9 C8 H8B . . 109.0(9) ?
C7 C8 H8B . . 108.8(9) ?
H8A C8 H8B . . 109.0(14) ?
O2 C9 C10 . . 109.73(11) ?
O2 C9 C8 . . 110.92(10) ?
C10 C9 C8 . . 112.02(12) ?
O2 C9 H9 . . 104.8(11) ?
C10 C9 H9 . . 111.0(11) ?
C8 C9 H9 . . 108.0(10) ?
C9 C10 H10A . . 111.3(13) ?
C9 C10 H10B . . 109.5(11) ?
H10A C10 H10B . . 109.7(16) ?
C9 C10 H10C . . 111.3(13) ?
H10A C10 H10C . . 105.7(17) ?
H10B C10 H10C . . 109.3(15) ?
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
O1 C3 . 1.3728(15) ?
O1 H1O1 . 0.91(3) ?
O2 C9 . 1.4473(16) ?
O2 H1O2 . 0.90(2) ?
C1 C6 . 1.3959(19) ?
C1 C2 . 1.3988(18) ?
C1 H1 . 0.943(19) ?
C2 C3 . 1.3865(18) ?
C2 H2 . 0.96(2) ?
C3 C4 . 1.3948(18) ?
C4 C5 . 1.390(2) ?
C4 H4 . 0.97(2) ?
C5 C6 . 1.3942(19) ?
C5 H5 . 0.94(2) ?
C6 C7 . 1.5180(17) ?
C7 C8 . 1.5265(19) ?
C7 H7A . 0.988(19) ?
C7 H7B . 0.99(2) ?
C8 C9 . 1.5241(17) ?
C8 H8A . 0.93(2) ?
C8 H8B . 1.018(15) ?
C9 C10 . 1.517(2) ?
C9 H9 . 0.938(17) ?
C10 H10A . 1.01(2) ?
C10 H10B . 1.013(18) ?
C10 H10C . 1.01(2) ?
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
_geom_hbond_publ_flag
O1 H1O1 O2 1_554 0.92(2) 1.72(2) 2.6247(13) 166(2) yes
O2 H1O2 O1 2_656 0.91(2) 1.88(2) 2.7869(13) 177.8(19) yes
C8 H8A Cg1 2_566 0.93(2) 2.822(15) 3.7033(13) 158.1(14) yes
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
C6 C1 C2 C3 . . . . 1.14(18) ?
C1 C2 C3 O1 . . . . 179.72(10) ?
C1 C2 C3 C4 . . . . -0.99(17) ?
O1 C3 C4 C5 . . . . 179.33(10) ?
C2 C3 C4 C5 . . . . 0.01(17) ?
C3 C4 C5 C6 . . . . 0.86(17) ?
C4 C5 C6 C1 . . . . -0.71(17) ?
C4 C5 C6 C7 . . . . 179.36(11) ?
C2 C1 C6 C5 . . . . -0.29(18) ?
C2 C1 C6 C7 . . . . 179.64(11) ?
C5 C6 C7 C8 . . . . 163.67(11) ?
C1 C6 C7 C8 . . . . -16.26(18) ?
C6 C7 C8 C9 . . . . -173.32(10) ?
C7 C8 C9 O2 . . . . 58.43(14) ?
C7 C8 C9 C10 . . . . -178.58(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 802470
