#------------------------------------------------------------------------------
#$Date: 2017-10-13 07:09:21 +0100 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/34/2203486.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_2203486
loop_
_publ_author_name
'Sandrock, Paul B.'
'Meyers, Cal Y.'
'Rath, Nigam P.'
'Robinson, Paul D.'
_publ_section_title
;
 Isopropyl 2,4,6-triisopropylphenyl sulfone: an aryl sulfone with
 unusual atom deviations from the aromatic least-squares plane
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o544
_journal_page_last               o546
_journal_paper_doi               10.1107/S1600536804004635
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C18 H30 O2 S1'
_chemical_formula_moiety         'C18 H30 O2 S1'
_chemical_formula_sum            'C18 H30 O2 S'
_chemical_formula_weight         310.49
_chemical_melting_point          .393E-305
_chemical_name_systematic
;
2,4,6-Triisopropylphenyl isopropyl sulfone
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.4705(6)
_cell_length_b                   11.5964(4)
_cell_length_c                   18.6412(7)
_cell_measurement_reflns_used    7039
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      2.4
_cell_volume                     3776.6(2)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2000)
;
_computing_publication_material
;
TEXSAN, SHELXL97 and PLATON (Spek, 2003)
;
_computing_structure_refinement
;
LS in TEXSAN (Molecular Structure Corporation, 1997) and
SHELXL97 (Sheldrick, 1997)
;
_computing_structure_solution    'SIR92 (Burla et al., 1989)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_av_sigmaI/netI    0.018
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            47817
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        <0.1
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.092
_exptl_crystal_density_meas      ?
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.065
_refine_ls_R_factor_gt           0.047
_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/[\s^2^(Fo^2^)+(0.0682P)^2^+1.2339P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.125
_refine_ls_wR_factor_ref         0.134
_reflns_number_gt                2530
_reflns_number_total             3319
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            om6220.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C18 H30 O2 S1'
_cod_database_code               2203486
_cod_database_fobs_code          2203486
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'
loop_
_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_type_symbol
S1 0.26750(3) 0.18789(4) 0.68743(3) 0.0530(2) Uani d . 1 S
O1 0.29869(9) 0.26676(13) 0.73887(9) 0.0719(5) Uani d . 1 O
O2 0.19212(9) 0.21430(15) 0.66199(9) 0.0729(5) Uani d . 1 O
C1 0.33006(11) 0.17647(16) 0.61105(11) 0.0482(5) Uani d . 1 C
C2 0.40502(12) 0.22266(17) 0.61247(12) 0.0528(5) Uani d . 1 C
C3 0.44467(13) 0.22577(19) 0.54772(13) 0.0620(6) Uani d . 1 C
C4 0.41564(14) 0.18375(19) 0.48372(13) 0.0639(6) Uani d . 1 C
C5 0.34502(14) 0.13205(19) 0.48617(12) 0.0623(6) Uani d . 1 C
C6 0.30062(12) 0.12626(17) 0.54746(11) 0.0543(5) Uani d . 1 C
C7 0.44725(13) 0.2693(2) 0.67762(13) 0.0650(6) Uani d . 1 C
C8 0.46094(18) 0.1940(3) 0.41454(16) 0.0896(9) Uani d . 1 C
C9 0.22496(13) 0.0613(2) 0.54023(13) 0.0647(6) Uani d . 1 C
C10 0.26564(12) 0.04734(18) 0.72788(12) 0.0566(5) Uani d . 1 C
C11 0.21031(17) 0.0509(3) 0.79086(15) 0.0884(8) Uani d . 1 C
C12 0.34410(14) 0.0074(2) 0.74870(16) 0.0807(8) Uani d . 1 C
C13 0.52705(16) 0.2171(3) 0.68480(17) 0.0924(9) Uani d . 1 C
C14 0.45244(18) 0.4007(2) 0.67426(18) 0.0953(9) Uani d . 1 C
C15 0.5264(3) 0.1173(3) 0.4121(2) 0.161(2) Uani d . 1 C
C16 0.4773(2) 0.3159(3) 0.39546(18) 0.1190(13) Uani d . 1 C
C17 0.17231(17) 0.1174(3) 0.48514(17) 0.0927(9) Uani d . 1 C
C18 0.23945(17) -0.0643(2) 0.52107(17) 0.0885(8) Uani d . 1 C
H3 0.4934 0.2579 0.5474 0.074 Uiso calc R 1 H
H5 0.3260 0.0991 0.4443 0.075 Uiso calc R 1 H
H7 0.4179 0.2485 0.7205 0.078 Uiso calc R 1 H
H8 0.4264 0.1661 0.3769 0.107 Uiso calc R 1 H
H9 0.1991 0.0634 0.5869 0.078 Uiso calc R 1 H
H10 0.2453 -0.0070 0.6924 0.068 Uiso calc R 1 H
H11A 0.2065 -0.0245 0.8118 0.133 Uiso calc R 1 H
H11B 0.1608 0.0749 0.7744 0.133 Uiso calc R 1 H
H11C 0.2287 0.1044 0.8261 0.133 Uiso calc R 1 H
H12A 0.3633 0.0551 0.7867 0.121 Uiso calc R 1 H
H12B 0.3776 0.0127 0.7080 0.121 Uiso calc R 1 H
H12C 0.3417 -0.0712 0.7647 0.121 Uiso calc R 1 H
H13A 0.5235 0.1345 0.6831 0.139 Uiso calc R 1 H
H13B 0.5491 0.2402 0.7297 0.139 Uiso calc R 1 H
H13C 0.5587 0.2437 0.6461 0.139 Uiso calc R 1 H
H14A 0.4811 0.4230 0.6326 0.143 Uiso calc R 1 H
H14B 0.4776 0.4289 0.7165 0.143 Uiso calc R 1 H
H14C 0.4019 0.4327 0.6715 0.143 Uiso calc R 1 H
H15A 0.5579 0.1368 0.3716 0.241 Uiso calc R 1 H
H15B 0.5091 0.0391 0.4075 0.241 Uiso calc R 1 H
H15C 0.5556 0.1252 0.4554 0.241 Uiso calc R 1 H
H16A 0.5086 0.3502 0.4320 0.178 Uiso calc R 1 H
H16B 0.4300 0.3577 0.3917 0.178 Uiso calc R 1 H
H16C 0.5038 0.3186 0.3504 0.178 Uiso calc R 1 H
H17A 0.1957 0.1137 0.4386 0.139 Uiso calc R 1 H
H17B 0.1638 0.1965 0.4980 0.139 Uiso calc R 1 H
H17C 0.1243 0.0772 0.4842 0.139 Uiso calc R 1 H
H18A 0.1919 -0.1058 0.5215 0.133 Uiso calc R 1 H
H18B 0.2738 -0.0977 0.5555 0.133 Uiso calc R 1 H
H18C 0.2618 -0.0688 0.4741 0.133 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0484(3) 0.0481(3) 0.0625(3) 0.0044(2) 0.0085(2) -0.0013(2)
O1 0.0747(11) 0.0610(9) 0.0800(11) -0.0046(8) 0.0145(9) -0.0197(8)
O2 0.0519(9) 0.0819(11) 0.0848(11) 0.0193(8) 0.0067(8) 0.0055(9)
C1 0.0464(11) 0.0425(11) 0.0558(12) 0.0025(9) 0.0054(9) 0.0055(9)
C2 0.0505(12) 0.0439(11) 0.0639(13) -0.0006(9) 0.0031(10) 0.0052(10)
C3 0.0502(12) 0.0575(13) 0.0782(16) -0.0057(10) 0.0128(11) 0.0092(12)
C4 0.0691(15) 0.0575(13) 0.0650(14) -0.0017(12) 0.0150(12) 0.0024(11)
C5 0.0712(15) 0.0587(13) 0.0569(13) -0.0046(11) 0.0060(11) -0.0030(11)
C6 0.0535(12) 0.0475(12) 0.0619(13) 0.0008(9) 0.0032(10) 0.0030(10)
C7 0.0547(13) 0.0687(15) 0.0715(15) -0.0087(11) 0.0012(11) 0.0005(12)
C8 0.102(2) 0.088(2) 0.0790(18) -0.0102(16) 0.0381(16) -0.0005(15)
C9 0.0605(14) 0.0671(15) 0.0666(14) -0.0122(11) 0.0002(11) -0.0019(11)
C10 0.0567(13) 0.0530(12) 0.0602(13) -0.0026(10) 0.0076(10) 0.0032(10)
C11 0.095(2) 0.088(2) 0.0825(18) 0.0049(16) 0.0356(15) 0.0132(15)
C12 0.0739(17) 0.0729(16) 0.0952(19) 0.0118(13) 0.0002(15) 0.0195(15)
C13 0.0650(17) 0.115(2) 0.098(2) 0.0022(16) -0.0154(15) 0.0072(18)
C14 0.094(2) 0.0752(18) 0.117(2) -0.0159(15) -0.0115(17) -0.0165(17)
C15 0.205(5) 0.113(3) 0.164(4) 0.054(3) 0.118(4) 0.020(3)
C16 0.161(3) 0.106(3) 0.090(2) 0.005(2) 0.043(2) 0.0300(19)
C17 0.0732(17) 0.098(2) 0.106(2) -0.0022(16) -0.0216(16) 0.0008(18)
C18 0.095(2) 0.0620(16) 0.109(2) -0.0218(14) -0.0021(17) 0.0015(15)
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'
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'
H H 0.0000 0.0000 '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
O2 S1 O1 115.76(10) no
O2 S1 C10 108.43(10) no
O1 S1 C10 107.77(10) no
O2 S1 C1 108.18(10) no
O1 S1 C1 110.21(10) no
C10 S1 C1 106.04(9) no
C2 C1 C6 120.47(19) yes
C3 C2 C1 117.0(2) yes
C4 C3 C2 123.8(2) yes
C5 C4 C3 117.0(2) yes
C4 C5 C6 123.6(2) yes
C5 C6 C1 117.88(19) yes
C2 C1 S1 121.28(16) no
C6 C1 S1 118.14(15) no
C3 C2 C7 116.22(19) no
C1 C2 C7 126.78(19) no
C5 C4 C8 122.1(2) no
C3 C4 C8 120.9(2) no
C5 C6 C9 115.9(2) no
C1 C6 C9 126.19(19) no
C2 C7 C13 111.9(2) no
C2 C7 C14 110.5(2) no
C13 C7 C14 110.2(2) no
C15 C8 C16 115.1(3) no
C15 C8 C4 113.0(3) no
C16 C8 C4 112.2(2) no
C18 C9 C17 110.5(2) no
C18 C9 C6 110.4(2) no
C17 C9 C6 111.8(2) no
C12 C10 C11 112.9(2) no
C12 C10 S1 111.89(16) no
C11 C10 S1 108.13(16) no
C4 C3 H3 118.1 no
C2 C3 H3 118.1 no
C4 C5 H5 118.2 no
C6 C5 H5 118.2 no
C2 C7 H7 108.0 no
C13 C7 H7 108.0 no
C14 C7 H7 108.0 no
C15 C8 H8 105.1 no
C16 C8 H8 105.1 no
C4 C8 H8 105.1 no
C18 C9 H9 108.0 no
C17 C9 H9 108.0 no
C6 C9 H9 108.0 no
C12 C10 H10 107.9 no
C11 C10 H10 107.9 no
S1 C10 H10 107.9 no
C10 C11 H11A 109.5 no
C10 C11 H11B 109.5 no
H11A C11 H11B 109.5 no
C10 C11 H11C 109.5 no
H11A C11 H11C 109.5 no
H11B C11 H11C 109.5 no
C10 C12 H12A 109.5 no
C10 C12 H12B 109.5 no
H12A C12 H12B 109.5 no
C10 C12 H12C 109.5 no
H12A C12 H12C 109.5 no
H12B C12 H12C 109.5 no
C7 C13 H13A 109.5 no
C7 C13 H13B 109.5 no
H13A C13 H13B 109.5 no
C7 C13 H13C 109.5 no
H13A C13 H13C 109.5 no
H13B C13 H13C 109.5 no
C7 C14 H14A 109.5 no
C7 C14 H14B 109.5 no
H14A C14 H14B 109.5 no
C7 C14 H14C 109.5 no
H14A C14 H14C 109.5 no
H14B C14 H14C 109.5 no
C8 C15 H15A 109.5 no
C8 C15 H15B 109.5 no
H15A C15 H15B 109.5 no
C8 C15 H15C 109.5 no
H15A C15 H15C 109.5 no
H15B C15 H15C 109.5 no
C8 C16 H16A 109.5 no
C8 C16 H16B 109.5 no
H16A C16 H16B 109.5 no
C8 C16 H16C 109.5 no
H16A C16 H16C 109.5 no
H16B C16 H16C 109.5 no
C9 C17 H17A 109.5 no
C9 C17 H17B 109.5 no
H17A C17 H17B 109.5 no
C9 C17 H17C 109.5 no
H17A C17 H17C 109.5 no
H17B C17 H17C 109.5 no
C9 C18 H18A 109.5 no
C9 C18 H18B 109.5 no
H18A C18 H18B 109.5 no
C9 C18 H18C 109.5 no
H18A C18 H18C 109.5 no
H18B C18 H18C 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 1.4328(16) no
S1 O1 1.4328(16) no
S1 C10 1.796(2) no
S1 C1 1.800(2) no
C1 C2 1.415(3) yes
C1 C6 1.417(3) yes
C2 C3 1.392(3) yes
C2 C7 1.520(3) no
C3 C4 1.385(3) yes
C4 C5 1.373(3) yes
C4 C8 1.518(3) no
C5 C6 1.383(3) yes
C6 C9 1.527(3) no
C7 C13 1.526(3) no
C7 C14 1.527(4) no
C8 C15 1.450(4) no
C8 C16 1.486(4) no
C9 C18 1.522(3) no
C9 C17 1.524(4) no
C10 C12 1.498(3) no
C10 C11 1.521(3) no
C3 H3 0.9300 no
C5 H5 0.9300 no
C7 H7 0.9800 no
C8 H8 0.9800 no
C9 H9 0.9800 no
C10 H10 0.9800 no
C11 H11A 0.9600 no
C11 H11B 0.9600 no
C11 H11C 0.9600 no
C12 H12A 0.9600 no
C12 H12B 0.9600 no
C12 H12C 0.9600 no
C13 H13A 0.9600 no
C13 H13B 0.9600 no
C13 H13C 0.9600 no
C14 H14A 0.9600 no
C14 H14B 0.9600 no
C14 H14C 0.9600 no
C15 H15A 0.9600 no
C15 H15B 0.9600 no
C15 H15C 0.9600 no
C16 H16A 0.9600 no
C16 H16B 0.9600 no
C16 H16C 0.9600 no
C17 H17A 0.9600 no
C17 H17B 0.9600 no
C17 H17C 0.9600 no
C18 H18A 0.9600 no
C18 H18B 0.9600 no
C18 H18C 0.9600 no
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
_geom_torsion_publ_flag
O2 S1 C1 C2 139.12(17) no
O1 S1 C1 C2 11.64(19) no
C10 S1 C1 C2 -104.74(17) no
O2 S1 C1 C6 -36.94(18) no
O1 S1 C1 C6 -164.41(15) no
C10 S1 C1 C6 79.21(17) no
C6 C1 C2 C3 5.7(3) no
S1 C1 C2 C3 -170.23(15) no
C6 C1 C2 C7 -174.1(2) no
S1 C1 C2 C7 9.9(3) no
C1 C2 C3 C4 -1.8(3) no
C7 C2 C3 C4 178.0(2) no
C2 C3 C4 C5 -2.9(3) no
C2 C3 C4 C8 177.7(2) no
C3 C4 C5 C6 3.9(3) no
C8 C4 C5 C6 -176.7(2) no
C4 C5 C6 C1 -0.1(3) no
C4 C5 C6 C9 -177.8(2) no
C2 C1 C6 C5 -4.9(3) no
S1 C1 C6 C5 171.22(16) no
C2 C1 C6 C9 172.61(19) no
S1 C1 C6 C9 -11.3(3) no
C3 C2 C7 C13 -50.2(3) no
C1 C2 C7 C13 129.6(2) no
C3 C2 C7 C14 73.0(3) no
C1 C2 C7 C14 -107.2(3) no
C5 C4 C8 C15 -107.5(4) no
C3 C4 C8 C15 71.8(4) no
C5 C4 C8 C16 120.3(3) no
C3 C4 C8 C16 -60.3(4) no
C5 C6 C9 C18 62.2(3) no
C1 C6 C9 C18 -115.3(3) no
C5 C6 C9 C17 -61.3(3) no
C1 C6 C9 C17 121.2(2) no
O2 S1 C10 C12 173.69(17) no
O1 S1 C10 C12 -60.3(2) no
C1 S1 C10 C12 57.7(2) no
O2 S1 C10 C11 -61.3(2) no
O1 S1 C10 C11 64.69(19) no
C1 S1 C10 C11 -177.30(18) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130948