#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/19/2221974.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_2221974
loop_
_publ_author_name
'Na, Risong'
'Wang, Min'
_publ_section_title
'[(1R,3S)-3-(1,3-Dithian-2-yl)-2,2-dimethylcyclopropyl]diphenylmethanol'
_journal_coeditor_code           CV2542
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1230
_journal_paper_doi               10.1107/S1600536809016079
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C22 H26 O S2'
_chemical_formula_moiety         'C22 H26 O S2'
_chemical_formula_sum            'C22 H26 O S2'
_chemical_formula_weight         370.55
_chemical_name_systematic
;
[(1R,3S)-3-(1,3-Dithian-2-yl)-2,2-
dimethylcyclopropyl]diphenylmethanol
;
_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                 101.14(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5578(19)
_cell_length_b                   11.199(2)
_cell_length_c                   9.6512(19)
_cell_measurement_reflns_used    7560
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.15
_cell_volume                     1013.6(4)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2000)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 2000)'
_computing_data_reduction        'CrystalStructure (Rigaku, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1071
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4303
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.9235
_exptl_absorpt_correction_T_min  0.8999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.296
_refine_ls_abs_structure_details 'Flack (1983), 1878 Friedel pairs'
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_coef       0.046(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.840
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4303
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.840
_refine_ls_R_factor_all          0.056
_refine_ls_R_factor_gt           0.038
_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)+(0.0379P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.080
_refine_ls_wR_factor_ref         0.084
_reflns_number_gt                2920
_reflns_number_total             4303
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2542.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2221974
_cod_database_fobs_code          2221974
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
C C1 0.6857(3) 0.2287(2) 0.2178(3) 0.0254(6) Uani d . 1 . .
H H1 0.6517 0.2825 0.1355 0.030 Uiso calc R 1 . .
C C2 0.6466(3) 0.2775(2) 0.3516(3) 0.0287(7) Uani d . 1 . .
C C3 0.8003(3) 0.2893(2) 0.3280(3) 0.0238(6) Uani d . 1 . .
H H3 0.8246 0.3717 0.3005 0.029 Uiso calc R 1 . .
C C4 0.5595(3) 0.3923(3) 0.3379(3) 0.0462(9) Uani d . 1 . .
H H4A 0.4577 0.3727 0.3176 0.069 Uiso calc R 1 . .
H H4B 0.5827 0.4407 0.2609 0.069 Uiso calc R 1 . .
H H4C 0.5822 0.4373 0.4265 0.069 Uiso calc R 1 . .
C C5 0.6172(3) 0.1950(3) 0.4668(3) 0.0369(8) Uani d . 1 . .
H H5A 0.5156 0.1745 0.4492 0.055 Uiso calc R 1 . .
H H5B 0.6432 0.2350 0.5585 0.055 Uiso calc R 1 . .
H H5C 0.6739 0.1220 0.4674 0.055 Uiso calc R 1 . .
C C6 0.9233(2) 0.2264(2) 0.4217(3) 0.0236(6) Uani d . 1 . .
H H6 0.8867 0.1549 0.4656 0.028 Uiso calc R 1 . .
C C7 1.1962(3) 0.1241(3) 0.4492(3) 0.0351(7) Uani d . 1 . .
H H7A 1.1632 0.0529 0.4944 0.042 Uiso calc R 1 . .
H H7B 1.2751 0.0987 0.4028 0.042 Uiso calc R 1 . .
C C8 1.2536(3) 0.2153(2) 0.5636(3) 0.0354(8) Uani d . 1 . .
H H8A 1.3404 0.1827 0.6245 0.042 Uiso calc R 1 . .
H H8B 1.2811 0.2887 0.5184 0.042 Uiso calc R 1 . .
C C9 1.1470(3) 0.2472(3) 0.6542(3) 0.0354(7) Uani d . 1 . .
H H9A 1.1958 0.2940 0.7366 0.042 Uiso calc R 1 . .
H H9B 1.1109 0.1729 0.6902 0.042 Uiso calc R 1 . .
C C10 0.6776(3) 0.0972(2) 0.1726(3) 0.0235(6) Uani d . 1 . .
C C11 0.7437(3) 0.0754(2) 0.0414(3) 0.0258(6) Uani d . 1 . .
C C12 0.7434(3) -0.0429(3) -0.0102(3) 0.0389(8) Uani d . 1 . .
H H12 0.6995 -0.1044 0.0341 0.047 Uiso calc R 1 . .
C C13 0.8053(3) -0.0705(3) -0.1232(3) 0.0479(9) Uani d . 1 . .
H H13 0.8059 -0.1507 -0.1551 0.057 Uiso calc R 1 . .
C C14 0.8676(3) 0.0196(4) -0.1912(3) 0.0522(10) Uani d . 1 . .
H H14 0.9091 0.0014 -0.2705 0.063 Uiso calc R 1 . .
C C15 0.8679(4) 0.1346(3) -0.1422(4) 0.0537(10) Uani d . 1 . .
H H15 0.9100 0.1958 -0.1885 0.064 Uiso calc R 1 . .
C C16 0.8079(3) 0.1635(3) -0.0258(3) 0.0404(8) Uani d . 1 . .
H H16 0.8108 0.2435 0.0074 0.048 Uiso calc R 1 . .
C C17 0.5212(3) 0.0589(2) 0.1427(3) 0.0259(6) Uani d . 1 . .
C C18 0.4713(3) -0.0319(3) 0.2171(3) 0.0345(7) Uani d . 1 . .
H H18 0.5356 -0.0737 0.2880 0.041 Uiso calc R 1 . .
C C19 0.3262(3) -0.0628(3) 0.1886(3) 0.0412(8) Uani d . 1 . .
H H19 0.2933 -0.1268 0.2385 0.049 Uiso calc R 1 . .
C C20 0.2309(3) -0.0007(3) 0.0882(3) 0.0392(8) Uani d . 1 . .
H H20 0.1323 -0.0203 0.0713 0.047 Uiso calc R 1 . .
C C21 0.2790(3) 0.0895(3) 0.0129(3) 0.0410(8) Uani d . 1 . .
H H21 0.2141 0.1313 -0.0575 0.049 Uiso calc R 1 . .
C C22 0.4234(3) 0.1196(3) 0.0402(3) 0.0370(8) Uani d . 1 . .
H H22 0.4559 0.1825 -0.0117 0.044 Uiso calc R 1 . .
O O1 0.75071(18) 0.02068(15) 0.28301(18) 0.0294(5) Uani d . 1 . .
H H2 0.8381 0.0324 0.2863 0.035 Uiso d R 1 . .
S S1 1.05026(7) 0.17887(6) 0.31479(7) 0.02959(18) Uani d . 1 . .
S S2 0.99674(7) 0.33324(6) 0.55984(8) 0.0331(2) Uani 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 0.0033 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'
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
C2 C1 C3 . . 60.55(17) ?
C2 C1 C10 . . 125.6(2) ?
C3 C1 C10 . . 127.8(2) ?
C2 C1 H1 . . 111.3 ?
C3 C1 H1 . . 111.3 ?
C10 C1 H1 . . 111.3 ?
C5 C2 C1 . . 121.2(2) ?
C5 C2 C4 . . 113.8(3) ?
C1 C2 C4 . . 116.8(2) ?
C5 C2 C3 . . 118.7(2) ?
C1 C2 C3 . . 60.24(18) ?
C4 C2 C3 . . 115.9(2) ?
C6 C3 C1 . . 125.3(2) ?
C6 C3 C2 . . 121.8(2) ?
C1 C3 C2 . . 59.21(17) ?
C6 C3 H3 . . 113.3 ?
C1 C3 H3 . . 113.3 ?
C2 C3 H3 . . 113.3 ?
C2 C4 H4A . . 109.5 ?
C2 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C2 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C2 C5 H5A . . 109.5 ?
C2 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C2 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C3 C6 S1 . . 108.90(19) ?
C3 C6 S2 . . 106.04(18) ?
S1 C6 S2 . . 113.65(13) ?
C3 C6 H6 . . 109.4 ?
S1 C6 H6 . . 109.4 ?
S2 C6 H6 . . 109.4 ?
C8 C7 S1 . . 114.18(19) ?
C8 C7 H7A . . 108.7 ?
S1 C7 H7A . . 108.7 ?
C8 C7 H7B . . 108.7 ?
S1 C7 H7B . . 108.7 ?
H7A C7 H7B . . 107.6 ?
C9 C8 C7 . . 112.9(2) ?
C9 C8 H8A . . 109.0 ?
C7 C8 H8A . . 109.0 ?
C9 C8 H8B . . 109.0 ?
C7 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
C8 C9 S2 . . 113.0(2) ?
C8 C9 H9A . . 109.0 ?
S2 C9 H9A . . 109.0 ?
C8 C9 H9B . . 109.0 ?
S2 C9 H9B . . 109.0 ?
H9A C9 H9B . . 107.8 ?
O1 C10 C17 . . 106.8(2) ?
O1 C10 C1 . . 111.8(2) ?
C17 C10 C1 . . 108.5(2) ?
O1 C10 C11 . . 107.24(19) ?
C17 C10 C11 . . 110.0(2) ?
C1 C10 C11 . . 112.4(2) ?
C16 C11 C12 . . 118.2(3) ?
C16 C11 C10 . . 124.1(2) ?
C12 C11 C10 . . 117.7(2) ?
C13 C12 C11 . . 121.2(3) ?
C13 C12 H12 . . 119.4 ?
C11 C12 H12 . . 119.4 ?
C12 C13 C14 . . 119.9(3) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
C15 C14 C13 . . 119.2(3) ?
C15 C14 H14 . . 120.4 ?
C13 C14 H14 . . 120.4 ?
C14 C15 C16 . . 121.5(3) ?
C14 C15 H15 . . 119.3 ?
C16 C15 H15 . . 119.3 ?
C11 C16 C15 . . 120.0(3) ?
C11 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C18 C17 C22 . . 118.3(3) ?
C18 C17 C10 . . 122.1(2) ?
C22 C17 C10 . . 119.5(2) ?
C17 C18 C19 . . 120.4(3) ?
C17 C18 H18 . . 119.8 ?
C19 C18 H18 . . 119.8 ?
C20 C19 C18 . . 120.4(3) ?
C20 C19 H19 . . 119.8 ?
C18 C19 H19 . . 119.8 ?
C21 C20 C19 . . 119.9(3) ?
C21 C20 H20 . . 120.1 ?
C19 C20 H20 . . 120.1 ?
C20 C21 C22 . . 119.8(3) ?
C20 C21 H21 . . 120.1 ?
C22 C21 H21 . . 120.1 ?
C21 C22 C17 . . 121.2(3) ?
C21 C22 H22 . . 119.4 ?
C17 C22 H22 . . 119.4 ?
C10 O1 H2 . . 105.8 ?
C7 S1 C6 . . 101.43(13) ?
C9 S2 C6 . . 99.98(13) ?
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 C2 . 1.515(4) ?
C1 C3 . 1.531(3) ?
C1 C10 . 1.533(4) ?
C1 H1 . 1.0000 ?
C2 C5 . 1.513(4) ?
C2 C4 . 1.523(4) ?
C2 C3 . 1.536(4) ?
C3 C6 . 1.511(3) ?
C3 H3 . 1.0000 ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
C4 H4C . 0.9800 ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C6 S1 . 1.818(3) ?
C6 S2 . 1.827(3) ?
C6 H6 . 1.0000 ?
C7 C8 . 1.526(4) ?
C7 S1 . 1.818(3) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C9 . 1.508(4) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 S2 . 1.821(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 O1 . 1.439(3) ?
C10 C17 . 1.529(4) ?
C10 C11 . 1.540(4) ?
C11 C16 . 1.387(4) ?
C11 C12 . 1.415(4) ?
C12 C13 . 1.372(4) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.398(5) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.371(5) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.395(4) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C17 C18 . 1.382(4) ?
C17 C22 . 1.399(4) ?
C18 C19 . 1.404(4) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.382(4) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.375(4) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.396(4) ?
C21 H21 . 0.9500 ?
C22 H22 . 0.9500 ?
O1 H2 . 0.8400 ?
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 H2 S1 . 0.84 2.58 3.330(2) 149.1
C7 H7A S2 2_746 0.99 2.89 3.736(3) 144.0
C9 H9A O1 2_756 0.99 2.60 3.236(3) 121.7
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
C3 C1 C2 C5 . . . . -107.5(3) ?
C10 C1 C2 C5 . . . . 10.0(4) ?
C3 C1 C2 C4 . . . . 106.0(3) ?
C10 C1 C2 C4 . . . . -136.5(3) ?
C10 C1 C2 C3 . . . . 117.5(3) ?
C2 C1 C3 C6 . . . . 109.2(3) ?
C10 C1 C3 C6 . . . . -4.9(4) ?
C10 C1 C3 C2 . . . . -114.1(3) ?
C5 C2 C3 C6 . . . . -3.5(4) ?
C1 C2 C3 C6 . . . . -115.0(3) ?
C4 C2 C3 C6 . . . . 137.5(3) ?
C5 C2 C3 C1 . . . . 111.5(3) ?
C4 C2 C3 C1 . . . . -107.5(3) ?
C1 C3 C6 S1 . . . . 71.5(3) ?
C2 C3 C6 S1 . . . . 144.1(2) ?
C1 C3 C6 S2 . . . . -165.9(2) ?
C2 C3 C6 S2 . . . . -93.3(3) ?
S1 C7 C8 C9 . . . . 66.4(3) ?
C7 C8 C9 S2 . . . . -69.4(3) ?
C2 C1 C10 O1 . . . . -51.7(3) ?
C3 C1 C10 O1 . . . . 26.2(4) ?
C2 C1 C10 C17 . . . . 65.9(3) ?
C3 C1 C10 C17 . . . . 143.8(3) ?
C2 C1 C10 C11 . . . . -172.3(2) ?
C3 C1 C10 C11 . . . . -94.4(3) ?
O1 C10 C11 C16 . . . . -121.1(3) ?
C17 C10 C11 C16 . . . . 123.0(3) ?
C1 C10 C11 C16 . . . . 2.1(3) ?
O1 C10 C11 C12 . . . . 56.5(3) ?
C17 C10 C11 C12 . . . . -59.4(3) ?
C1 C10 C11 C12 . . . . 179.7(2) ?
C16 C11 C12 C13 . . . . 0.4(4) ?
C10 C11 C12 C13 . . . . -177.4(3) ?
C11 C12 C13 C14 . . . . -1.4(4) ?
C12 C13 C14 C15 . . . . 1.1(5) ?
C13 C14 C15 C16 . . . . 0.1(5) ?
C12 C11 C16 C15 . . . . 0.9(4) ?
C10 C11 C16 C15 . . . . 178.5(3) ?
C14 C15 C16 C11 . . . . -1.1(5) ?
O1 C10 C17 C18 . . . . 1.3(3) ?
C1 C10 C17 C18 . . . . -119.4(3) ?
C11 C10 C17 C18 . . . . 117.4(3) ?
O1 C10 C17 C22 . . . . 179.1(2) ?
C1 C10 C17 C22 . . . . 58.5(3) ?
C11 C10 C17 C22 . . . . -64.8(3) ?
C22 C17 C18 C19 . . . . 0.8(4) ?
C10 C17 C18 C19 . . . . 178.6(3) ?
C17 C18 C19 C20 . . . . -1.7(5) ?
C18 C19 C20 C21 . . . . 1.9(5) ?
C19 C20 C21 C22 . . . . -1.3(5) ?
C20 C21 C22 C17 . . . . 0.4(5) ?
C18 C17 C22 C21 . . . . -0.2(4) ?
C10 C17 C22 C21 . . . . -178.1(3) ?
C8 C7 S1 C6 . . . . -55.9(2) ?
C3 C6 S1 C7 . . . . 173.11(18) ?
S2 C6 S1 C7 . . . . 55.16(17) ?
C8 C9 S2 C6 . . . . 61.1(2) ?
C3 C6 S2 C9 . . . . -176.75(19) ?
S1 C6 S2 C9 . . . . -57.17(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742287
