#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/02/7150279.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_7150279
loop_
_publ_author_name
'Hitchcock, Peter B.'
'Rowlands, Gareth J.'
'Seacome, Richard J.'
_publ_section_title
;
 The synthesis and directed ortho-lithiation of
 4-tert-butylsulfinyl[2.2]paracyclophane.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3873
_journal_page_last               3876
_journal_paper_doi               10.1039/b509994c
_journal_volume                  3
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H24 O1 S1'
_chemical_formula_sum            'C20 H24 O S'
_chemical_formula_weight         312.45
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2004-07-21T14:25:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9622(3)
_cell_length_b                   11.5421(3)
_cell_length_c                   14.9696(3)
_cell_measurement_reflns_used    15410
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      3.705
_cell_measurement_wavelength     0.71073
_cell_volume                     1721.28(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.197426E-1
_diffrn_orient_matrix_UB_12      -0.492042E-1
_diffrn_orient_matrix_UB_13      -0.533909E-1
_diffrn_orient_matrix_UB_21      0.391286E-1
_diffrn_orient_matrix_UB_22      0.687277E-1
_diffrn_orient_matrix_UB_23      -0.312465E-1
_diffrn_orient_matrix_UB_31      0.903062E-1
_diffrn_orient_matrix_UB_32      -0.190219E-1
_diffrn_orient_matrix_UB_33      0.252109E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23660
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         3.78
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.16
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         3022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0606P)²+0.2763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1001
_reflns_number_gt                2694
_reflns_number_total             3022
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b509994c.txt
_cod_data_source_block           jul2004
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_original_formula_sum        'C20 H24 O1 S1'
_cod_database_code               7150279
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.96363(6) 0.53669(5) 0.24181(4) 0.03489(18) Uani 1 1 d . . .
O O 0.9185(2) 0.64307(18) 0.29029(12) 0.0539(6) Uani 1 1 d . . .
C1 C 0.6594(3) 0.7313(4) 0.1713(3) 0.0676(10) Uani 1 1 d . . .
H1B H 0.664(5) 0.729(4) 0.229(3) 0.108(17) Uiso 1 1 d . . .
H1A H 0.610(4) 0.794(3) 0.147(2) 0.068(10) Uiso 1 1 d . . .
C2 C 0.8010(3) 0.7430(3) 0.1243(2) 0.0506(7) Uani 1 1 d . . .
H2A H 0.791(3) 0.799(3) 0.080(2) 0.058(9) Uiso 1 1 d . . .
H2B H 0.867(3) 0.775(3) 0.172(2) 0.066(9) Uiso 1 1 d . . .
C3 C 0.8474(2) 0.6291(2) 0.08301(17) 0.0351(6) Uani 1 1 d . . .
C4 C 0.8933(2) 0.5332(2) 0.13145(14) 0.0304(5) Uani 1 1 d . . .
C5 C 0.8744(3) 0.4219(2) 0.09843(17) 0.0350(6) Uani 1 1 d . . .
H5 H 0.899(3) 0.361(2) 0.1388(18) 0.043(7) Uiso 1 1 d . . .
C6 C 0.8165(3) 0.4027(2) 0.01510(17) 0.0388(6) Uani 1 1 d . . .
C7 C 0.8035(3) 0.4982(2) -0.03996(17) 0.0419(6) Uani 1 1 d . . .
H7 H 0.766(3) 0.487(3) -0.098(2) 0.056(8) Uiso 1 1 d . . .
C8 C 0.8194(3) 0.6088(2) -0.00632(17) 0.0408(6) Uani 1 1 d . . .
H8 H 0.791(3) 0.677(3) -0.041(2) 0.054(8) Uiso 1 1 d . . .
C9 C 0.7459(3) 0.2906(3) -0.0067(2) 0.0514(8) Uani 1 1 d . . .
H9A H 0.786(3) 0.223(3) 0.0212(19) 0.051(8) Uiso 1 1 d . . .
H9B H 0.736(4) 0.275(3) -0.077(3) 0.096(12) Uiso 1 1 d . . .
C10 C 0.5951(3) 0.2919(3) 0.0195(3) 0.0636(9) Uani 1 1 d . . .
H10A H 0.578(3) 0.247(3) 0.069(2) 0.057(10) Uiso 1 1 d . . .
H10B H 0.540(4) 0.291(3) -0.048(3) 0.088(11) Uiso 1 1 d . . .
C11 C 0.5542(3) 0.4003(3) 0.0715(2) 0.0480(7) Uani 1 1 d . . .
C12 C 0.5795(3) 0.4122(3) 0.1611(2) 0.0532(8) Uani 1 1 d . . .
H12 H 0.599(3) 0.328(3) 0.2157(19) 0.064 Uiso 1 1 d . . .
C13 C 0.5941(3) 0.5231(4) 0.1983(2) 0.0560(9) Uani 1 1 d . . .
H13 H 0.617(3) 0.535(3) 0.254(2) 0.067(9) Uiso 1 1 d . . .
C14 C 0.5849(3) 0.6222(3) 0.1453(2) 0.0488(7) Uani 1 1 d . . .
C15 C 0.5299(3) 0.6080(3) 0.06102(19) 0.0461(7) Uani 1 1 d . . .
H15 H 0.509(2) 0.681(2) 0.0264(16) 0.037(7) Uiso 1 1 d . . .
C16 C 0.5145(2) 0.4977(3) 0.02524(19) 0.0480(7) Uani 1 1 d . . .
H16 H 0.474(3) 0.491(2) -0.0401(18) 0.053(7) Uiso 1 1 d . . .
C17 C 1.1434(2) 0.5602(2) 0.21283(16) 0.0354(6) Uani 1 1 d . . .
C18 C 1.1615(3) 0.6750(3) 0.1655(2) 0.0510(8) Uani 1 1 d . . .
H18A H 1.117(3) 0.673(3) 0.106(2) 0.058(9) Uiso 1 1 d . . .
H18B H 1.117(3) 0.732(3) 0.197(2) 0.061(10) Uiso 1 1 d . . .
H18C H 1.265(4) 0.689(3) 0.157(2) 0.065(9) Uiso 1 1 d . . .
C19 C 1.2143(3) 0.5618(3) 0.30294(19) 0.0449(7) Uani 1 1 d . . .
H19A H 1.165(4) 0.628(3) 0.342(2) 0.071(10) Uiso 1 1 d . . .
H19B H 1.316(4) 0.566(3) 0.294(2) 0.080(11) Uiso 1 1 d . . .
H19C H 1.197(3) 0.492(3) 0.3363(19) 0.050(8) Uiso 1 1 d . . .
C20 C 1.1897(3) 0.4582(3) 0.15641(19) 0.0477(7) Uani 1 1 d . . .
H20A H 1.294(4) 0.456(3) 0.156(2) 0.091(11) Uiso 1 1 d . . .
H20B H 1.154(3) 0.378(3) 0.190(2) 0.068(10) Uiso 1 1 d . . .
H20C H 1.153(3) 0.461(2) 0.0967(17) 0.039(7) Uiso 1 1 d . . .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O S C4 110.36(11) . . ?
O S C17 106.38(11) . . ?
C4 S C17 99.46(11) . . ?
C14 C1 C2 113.2(3) . . ?
C3 C2 C1 112.1(3) . . ?
C8 C3 C4 115.6(2) . . ?
C8 C3 C2 118.4(3) . . ?
C4 C3 C2 124.8(2) . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 S 113.63(18) . . ?
C3 C4 S 125.92(18) . . ?
C4 C5 C6 121.4(2) . . ?
C7 C6 C5 116.5(2) . . ?
C7 C6 C9 120.8(2) . . ?
C5 C6 C9 121.5(3) . . ?
C8 C7 C6 120.6(2) . . ?
C7 C8 C3 122.0(2) . . ?
C6 C9 C10 112.8(2) . . ?
C11 C10 C9 113.2(2) . . ?
C12 C11 C16 117.5(3) . . ?
C12 C11 C10 122.1(3) . . ?
C16 C11 C10 119.2(3) . . ?
C11 C12 C13 119.9(3) . . ?
C14 C13 C12 121.0(3) . . ?
C15 C14 C13 116.6(3) . . ?
C15 C14 C1 121.8(3) . . ?
C13 C14 C1 120.3(3) . . ?
C14 C15 C16 120.2(3) . . ?
C11 C16 C15 121.5(3) . . ?
C18 C17 C20 112.5(3) . . ?
C18 C17 C19 110.4(2) . . ?
C20 C17 C19 111.1(2) . . ?
C18 C17 S 110.56(19) . . ?
C20 C17 S 107.95(18) . . ?
C19 C17 S 103.99(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S O 1.495(2) . ?
S C4 1.795(2) . ?
S C17 1.863(2) . ?
C1 C14 1.512(5) . ?
C1 C2 1.583(5) . ?
C2 C3 1.524(4) . ?
C3 C8 1.386(4) . ?
C3 C4 1.400(3) . ?
C4 C5 1.390(4) . ?
C5 C6 1.392(4) . ?
C6 C7 1.383(4) . ?
C6 C9 1.508(4) . ?
C7 C8 1.381(4) . ?
C9 C10 1.553(5) . ?
C10 C11 1.529(4) . ?
C11 C12 1.371(5) . ?
C11 C16 1.378(4) . ?
C12 C13 1.404(5) . ?
C13 C14 1.395(5) . ?
C14 C15 1.385(4) . ?
C15 C16 1.389(4) . ?
C17 C18 1.512(4) . ?
C17 C20 1.521(4) . ?
C17 C19 1.523(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21141209
