#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/91/2239182.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_2239182
loop_
_publ_author_name
'Wu, Jinglan'
'Chen, Chen'
_publ_section_title
;
 (E)-2-Methyl-3-phenylselanyl-4-(phenylsulfinyl)oct-3-en-2-ol
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o8
_journal_paper_doi               10.1107/S1600536813032182
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C21 H26 O2 S Se'
_chemical_formula_moiety         'C21 H26 O2 S Se'
_chemical_formula_sum            'C21 H26 O2 S Se'
_chemical_formula_weight         421.44
_chemical_name_systematic
;
(E)-2-Methyl-3-phenylselanyl-4-(phenylsulfinyl)oct-3-en-2-ol
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.280(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.869(3)
_cell_length_b                   19.445(4)
_cell_length_c                   8.3702(18)
_cell_measurement_reflns_used    2566
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.27
_cell_measurement_theta_min      5.28
_cell_volume                     2060.9(8)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1295
_diffrn_reflns_av_sigmaI/netI    0.1057
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11048
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.61
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.934
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.993
_refine_diff_density_min         -0.560
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4029
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0859
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1331P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2189
_refine_ls_wR_factor_ref         0.2302
_reflns_number_gt                2554
_reflns_number_total             4029
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7167sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        2061.0(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239182
_cod_database_fobs_code          2239182
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_symmetry_multiplicity
Se Se 0.75777(6) 0.20048(3) 0.48905(9) 0.0587(3) Uani d . 1 1
S S 0.58519(11) -0.00576(8) 0.36854(17) 0.0387(4) Uani d . 1 1
O O1 0.7008(3) 0.0066(2) 0.6746(5) 0.0426(10) Uani d D 1 1
O O2 0.4924(3) -0.0048(2) 0.2318(5) 0.0492(11) Uani d . 1 1
C C1 0.7020(4) 0.1084(3) 0.5070(7) 0.0386(13) Uani d . 1 1
C C2 0.6377(4) 0.0827(3) 0.3772(7) 0.0373(13) Uani d . 1 1
C C3 0.5957(5) 0.1213(3) 0.2208(7) 0.0491(15) Uani d . 1 1
H H3A 0.5782 0.0886 0.1325 0.059 Uiso calc R 1 1
H H3B 0.6504 0.1516 0.1951 0.059 Uiso calc R 1 1
C C4 0.4977(6) 0.1639(4) 0.2346(8) 0.0600(18) Uani d . 1 1
H H4A 0.4414 0.1332 0.2520 0.072 Uiso calc R 1 1
H H4B 0.5138 0.1940 0.3282 0.072 Uiso calc R 1 1
C C5 0.4604(6) 0.2067(4) 0.0850(10) 0.071(2) Uani d . 1 1
H H5A 0.4431 0.1764 -0.0080 0.086 Uiso calc R 1 1
H H5B 0.5177 0.2364 0.0662 0.086 Uiso calc R 1 1
C C6 0.3650(8) 0.2508(5) 0.0966(13) 0.101(3) Uani d . 1 1
H H6A 0.3091 0.2222 0.1211 0.151 Uiso calc R 1 1
H H6B 0.3419 0.2738 -0.0049 0.151 Uiso calc R 1 1
H H6C 0.3836 0.2843 0.1812 0.151 Uiso calc R 1 1
C C7 0.7396(4) 0.0751(3) 0.6735(7) 0.0424(14) Uani d . 1 1
C C8 0.8601(5) 0.0684(4) 0.7106(9) 0.0636(19) Uani d . 1 1
H H8A 0.8812 0.0461 0.8136 0.095 Uiso calc R 1 1
H H8B 0.8914 0.1134 0.7144 0.095 Uiso calc R 1 1
H H8C 0.8833 0.0417 0.6272 0.095 Uiso calc R 1 1
C C9 0.7015(6) 0.1181(4) 0.8048(8) 0.0637(19) Uani d . 1 1
H H9A 0.6257 0.1193 0.7848 0.096 Uiso calc R 1 1
H H9B 0.7283 0.1641 0.8027 0.096 Uiso calc R 1 1
H H9C 0.7265 0.0980 0.9094 0.096 Uiso calc R 1 1
C C10 0.6901(4) -0.0421(3) 0.2807(6) 0.0362(12) Uani d . 1 1
C C11 0.7778(5) -0.0700(3) 0.3809(7) 0.0449(14) Uani d . 1 1
H H11 0.7810 -0.0713 0.4928 0.054 Uiso calc R 1 1
C C12 0.8597(5) -0.0957(4) 0.3142(8) 0.0545(17) Uani d . 1 1
H H12 0.9184 -0.1142 0.3813 0.065 Uiso calc R 1 1
C C13 0.8556(5) -0.0943(3) 0.1477(8) 0.0534(17) Uani d . 1 1
H H13 0.9117 -0.1112 0.1032 0.064 Uiso calc R 1 1
C C14 0.7675(5) -0.0676(4) 0.0483(8) 0.0549(17) Uani d . 1 1
H H14 0.7645 -0.0667 -0.0635 0.066 Uiso calc R 1 1
C C15 0.6836(5) -0.0422(3) 0.1137(7) 0.0467(15) Uani d . 1 1
H H15 0.6237 -0.0253 0.0462 0.056 Uiso calc R 1 1
C C16 0.8780(5) 0.1798(3) 0.3887(7) 0.0435(14) Uani d . 1 1
C C17 0.9578(6) 0.2285(4) 0.4050(8) 0.0568(17) Uani d . 1 1
H H17 0.9518 0.2686 0.4630 0.068 Uiso calc R 1 1
C C18 1.0448(7) 0.2181(5) 0.3372(10) 0.072(2) Uani d . 1 1
H H18 1.0966 0.2518 0.3461 0.087 Uiso calc R 1 1
C C19 1.0569(6) 0.1583(4) 0.2558(9) 0.066(2) Uani d . 1 1
H H19 1.1176 0.1511 0.2119 0.080 Uiso calc R 1 1
C C20 0.9785(6) 0.1086(4) 0.2390(9) 0.0629(19) Uani d . 1 1
H H20 0.9865 0.0677 0.1848 0.075 Uiso calc R 1 1
C C21 0.8876(5) 0.1202(4) 0.3038(8) 0.0549(17) Uani d . 1 1
H H21 0.8336 0.0877 0.2898 0.066 Uiso calc R 1 1
H H1 0.644(6) 0.000(8) 0.710(16) 0.19(6) Uiso d D 1 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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
_geom_angle_publ_flag
C16 Se C1 100.2(2) n
O2 S C10 104.3(2) n
O2 S C2 104.7(2) n
C10 S C2 95.0(2) n
C7 O1 H1 117(10) ?
C2 C1 C7 128.9(5) ?
C2 C1 Se 117.6(4) n
C7 C1 Se 113.5(4) n
C1 C2 C3 125.9(6) ?
C1 C2 S 123.3(4) n
C3 C2 S 110.8(4) n
C2 C3 C4 111.9(5) ?
C2 C3 H3A 109.2 ?
C4 C3 H3A 109.2 ?
C2 C3 H3B 109.2 ?
C4 C3 H3B 109.2 ?
H3A C3 H3B 107.9 ?
C5 C4 C3 112.4(6) ?
C5 C4 H4A 109.1 ?
C3 C4 H4A 109.1 ?
C5 C4 H4B 109.1 ?
C3 C4 H4B 109.1 ?
H4A C4 H4B 107.9 ?
C4 C5 C6 113.6(7) ?
C4 C5 H5A 108.8 ?
C6 C5 H5A 108.8 ?
C4 C5 H5B 108.8 ?
C6 C5 H5B 108.8 ?
H5A C5 H5B 107.7 ?
C5 C6 H6A 109.5 ?
C5 C6 H6B 109.5 ?
H6A C6 H6B 109.5 ?
C5 C6 H6C 109.5 ?
H6A C6 H6C 109.5 ?
H6B C6 H6C 109.5 ?
O1 C7 C9 110.5(5) n
O1 C7 C8 105.3(5) n
C9 C7 C8 110.1(6) ?
O1 C7 C1 110.3(4) n
C9 C7 C1 109.4(5) ?
C8 C7 C1 111.3(5) ?
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 ?
C7 C9 H9A 109.5 ?
C7 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C7 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C15 C10 C11 120.2(5) ?
C15 C10 S 120.0(4) n
C11 C10 S 119.8(4) n
C12 C11 C10 119.8(6) ?
C12 C11 H11 120.1 ?
C10 C11 H11 120.1 ?
C11 C12 C13 120.6(6) ?
C11 C12 H12 119.7 ?
C13 C12 H12 119.7 ?
C14 C13 C12 119.5(6) ?
C14 C13 H13 120.2 ?
C12 C13 H13 120.2 ?
C13 C14 C15 120.6(6) ?
C13 C14 H14 119.7 ?
C15 C14 H14 119.7 ?
C14 C15 C10 119.2(5) ?
C14 C15 H15 120.4 ?
C10 C15 H15 120.4 ?
C21 C16 C17 119.5(6) ?
C21 C16 Se 123.5(5) n
C17 C16 Se 117.0(5) n
C18 C17 C16 120.7(7) ?
C18 C17 H17 119.7 ?
C16 C17 H17 119.7 ?
C17 C18 C19 120.7(7) ?
C17 C18 H18 119.6 ?
C19 C18 H18 119.6 ?
C18 C19 C20 119.7(7) ?
C18 C19 H19 120.2 ?
C20 C19 H19 120.2 ?
C19 C20 C21 119.7(7) ?
C19 C20 H20 120.2 ?
C21 C20 H20 120.2 ?
C16 C21 C20 119.7(6) ?
C16 C21 H21 120.1 ?
C20 C21 H21 120.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Se C16 1.930(6) n
Se C1 1.945(6) n
S O2 1.499(4) n
S C10 1.793(6) n
S C2 1.844(6) n
O1 C7 1.422(7) n
O1 H1 0.85(2) ?
C1 C2 1.340(8) ?
C1 C7 1.534(8) ?
C2 C3 1.523(8) ?
C3 C4 1.529(9) ?
C3 H3A 0.9700 ?
C3 H3B 0.9700 ?
C4 C5 1.510(9) ?
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
C5 C6 1.514(11) ?
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
C6 H6A 0.9600 ?
C6 H6B 0.9600 ?
C6 H6C 0.9600 ?
C7 C9 1.530(9) ?
C7 C8 1.532(8) ?
C8 H8A 0.9600 ?
C8 H8B 0.9600 ?
C8 H8C 0.9600 ?
C9 H9A 0.9600 ?
C9 H9B 0.9600 ?
C9 H9C 0.9600 ?
C10 C15 1.386(8) ?
C10 C11 1.392(8) ?
C11 C12 1.371(9) ?
C11 H11 0.9300 ?
C12 C13 1.385(9) ?
C12 H12 0.9300 ?
C13 C14 1.382(9) ?
C13 H13 0.9300 ?
C14 C15 1.385(9) ?
C14 H14 0.9300 ?
C15 H15 0.9300 ?
C16 C21 1.378(9) ?
C16 C17 1.385(9) ?
C17 C18 1.357(11) ?
C17 H17 0.9300 ?
C18 C19 1.370(12) ?
C18 H18 0.9300 ?
C19 C20 1.387(10) ?
C19 H19 0.9300 ?
C20 C21 1.393(9) ?
C20 H20 0.9300 ?
C21 H21 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
_geom_hbond_publ_flag
O1 H1 O2 3_656 0.85(9) 1.91(8) 2.737(6) 167(10) yes
C11 H11 O1 . 0.93 2.50 3.180(7) 130 yes
C15 H15 O2 3_655 0.93 2.60 3.463(7) 155 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
C16 Se C1 C2 -84.4(5)
C16 Se C1 C7 95.7(4)
C7 C1 C2 C3 174.0(5)
Se C1 C2 C3 -5.9(8)
C7 C1 C2 S -4.4(8)
Se C1 C2 S 175.7(3)
O2 S C2 C1 161.7(5)
C10 S C2 C1 -92.1(5)
O2 S C2 C3 -16.9(4)
C10 S C2 C3 89.3(4)
C1 C2 C3 C4 -83.7(8)
S C2 C3 C4 94.9(6)
C2 C3 C4 C5 175.6(6)
C3 C4 C5 C6 -178.6(8)
C2 C1 C7 O1 3.4(8)
Se C1 C7 O1 -176.6(4)
C2 C1 C7 C9 -118.2(6)
Se C1 C7 C9 61.7(6)
C2 C1 C7 C8 119.9(7)
Se C1 C7 C8 -60.1(6)
O2 S C10 C15 19.7(5)
C2 S C10 C15 -86.9(5)
O2 S C10 C11 -160.4(5)
C2 S C10 C11 93.0(5)
C15 C10 C11 C12 2.1(9)
S C10 C11 C12 -177.8(5)
C10 C11 C12 C13 -0.3(10)
C11 C12 C13 C14 -0.9(11)
C12 C13 C14 C15 0.1(11)
C13 C14 C15 C10 1.7(10)
C11 C10 C15 C14 -2.8(9)
S C10 C15 C14 177.1(5)
C1 Se C16 C21 21.1(6)
C1 Se C16 C17 -158.8(5)
C21 C16 C17 C18 0.5(10)
Se C16 C17 C18 -179.6(5)
C16 C17 C18 C19 -2.1(11)
C17 C18 C19 C20 1.6(12)
C18 C19 C20 C21 0.6(11)
C17 C16 C21 C20 1.7(10)
Se C16 C21 C20 -178.2(5)
C19 C20 C21 C16 -2.2(10)
