#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/02/7150278.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_7150278
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   geom
_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             2004-06-23T13:25:51-00:00
_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                   9.9320(5)
_cell_length_b                   11.5642(6)
_cell_length_c                   14.7502(4)
_cell_measurement_reflns_used    6688
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      3.705
_cell_measurement_wavelength     0.71073
_cell_volume                     1694.14(13)
_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 0.967
_diffrn_measured_fraction_theta_max 0.967
_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      -0.65779E-1
_diffrn_orient_matrix_UB_12      0.144074E-1
_diffrn_orient_matrix_UB_13      -0.500687E-1
_diffrn_orient_matrix_UB_21      -0.744329E-1
_diffrn_orient_matrix_UB_22      0.60521E-2
_diffrn_orient_matrix_UB_23      0.454072E-1
_diffrn_orient_matrix_UB_31      0.164395E-1
_diffrn_orient_matrix_UB_32      0.850501E-1
_diffrn_orient_matrix_UB_33      0.52504E-2
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0458
_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       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12874
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         3.79
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.183
_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   0.07(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.97
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.97
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0627P)²+0.0356P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                2406
_reflns_number_total             2909
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b509994c.txt
_cod_data_source_block           jun2504
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_original_formula_sum        'C20 H24 O1 S1'
_cod_database_code               7150278
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 0.49878(6) 0.48424(4) 0.50138(4) 0.02991(18) Uani 1 1 d . . .
O O 0.39801(18) 0.40471(18) 0.54349(12) 0.0462(5) Uani 1 1 d . . .
C1 C 0.4244(4) 0.7799(3) 0.4158(3) 0.0573(9) Uani 1 1 d . . .
H1B H 0.437(4) 0.776(3) 0.481(3) 0.082(12) Uiso 1 1 d . . .
H1A H 0.438(3) 0.853(3) 0.388(2) 0.075(11) Uiso 1 1 d . . .
C2 C 0.5439(3) 0.7042(2) 0.3779(2) 0.0442(7) Uani 1 1 d . . .
H2B H 0.604(3) 0.688(2) 0.423(2) 0.047(8) Uiso 1 1 d . . .
H2A H 0.591(3) 0.745(2) 0.3323(19) 0.046(8) Uiso 1 1 d . . .
C3 C 0.4974(3) 0.59334(18) 0.33408(15) 0.0320(5) Uani 1 1 d . . .
C4 C 0.4569(2) 0.49593(19) 0.38326(16) 0.0281(5) Uani 1 1 d . . .
C5 C 0.3631(3) 0.4193(2) 0.34784(17) 0.0316(6) Uani 1 1 d . . .
H5 H 0.326(2) 0.366(2) 0.3901(17) 0.031(7) Uiso 1 1 d . . .
C6 C 0.3089(3) 0.4365(2) 0.26195(17) 0.0347(6) Uani 1 1 d . . .
C7 C 0.3727(3) 0.5165(2) 0.20623(18) 0.0402(7) Uani 1 1 d . . .
H7 H 0.339(3) 0.529(2) 0.146(2) 0.050(8) Uiso 1 1 d . . .
C8 C 0.4663(3) 0.5918(3) 0.24214(18) 0.0405(7) Uani 1 1 d . . .
H8 H 0.499(3) 0.650(3) 0.2090(19) 0.053(8) Uiso 1 1 d . . .
C9 C 0.1712(3) 0.3912(3) 0.2367(2) 0.0475(8) Uani 1 1 d . . .
H9B H 0.162(3) 0.319(3) 0.254(2) 0.072(11) Uiso 1 1 d . . .
H9A H 0.158(4) 0.390(3) 0.169(3) 0.081(11) Uiso 1 1 d . . .
C10 C 0.0552(4) 0.4639(5) 0.2757(4) 0.0710(12) Uani 1 1 d . . .
H10B H 0.009(5) 0.421(4) 0.312(3) 0.109(17) Uiso 1 1 d . . .
H10A H -0.006(5) 0.481(4) 0.232(3) 0.119(18) Uiso 1 1 d . . .
C11 C 0.1000(3) 0.5747(3) 0.3230(2) 0.0486(8) Uani 1 1 d . . .
C12 C 0.1340(3) 0.5734(3) 0.41418(19) 0.0461(7) Uani 1 1 d . . .
H12 H 0.103(3) 0.502(3) 0.4540(19) 0.055(8) Uiso 1 1 d . . .
C13 C 0.2265(3) 0.6526(3) 0.4484(2) 0.0422(7) Uani 1 1 d . . .
H13 H 0.262(3) 0.641(3) 0.512(2) 0.054(8) Uiso 1 1 d . . .
C14 C 0.2875(3) 0.7322(2) 0.39264(19) 0.0423(7) Uani 1 1 d . . .
C15 C 0.2299(3) 0.7489(3) 0.3073(2) 0.0515(8) Uani 1 1 d . . .
H15 H 0.267(3) 0.806(3) 0.268(2) 0.064(9) Uiso 1 1 d . . .
C16 C 0.1376(3) 0.6697(3) 0.2727(2) 0.0533(8) Uani 1 1 d . . .
H16 H 0.107(3) 0.675(2) 0.206(2) 0.056(8) Uiso 1 1 d . . .
C17 C 0.6584(2) 0.4009(2) 0.4962(2) 0.0372(6) Uani 1 1 d . . .
C18 C 0.7612(3) 0.4682(4) 0.4407(3) 0.0597(10) Uani 1 1 d . . .
H18C H 0.782(4) 0.554(4) 0.466(3) 0.100(14) Uiso 1 1 d . . .
H18B H 0.728(3) 0.474(3) 0.372(2) 0.065(9) Uiso 1 1 d . . .
H18A H 0.841(4) 0.424(3) 0.449(2) 0.083(12) Uiso 1 1 d . . .
C19 C 0.7038(4) 0.3929(3) 0.5949(2) 0.0507(8) Uani 1 1 d . . .
H19C H 0.726(4) 0.472(4) 0.618(3) 0.094(13) Uiso 1 1 d . . .
H19A H 0.637(4) 0.352(3) 0.629(2) 0.070(10) Uiso 1 1 d . . .
H19B H 0.787(3) 0.355(3) 0.593(2) 0.066(10) Uiso 1 1 d . . .
C20 C 0.6299(5) 0.2820(3) 0.4571(3) 0.0606(10) Uani 1 1 d . . .
H20C H 0.721(4) 0.237(4) 0.457(3) 0.105(14) Uiso 1 1 d . . .
H20A H 0.564(4) 0.250(3) 0.490(3) 0.072(13) Uiso 1 1 d . . .
H20B H 0.603(3) 0.284(3) 0.396(2) 0.057(9) 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 107.11(11) . . ?
O S C17 105.62(11) . . ?
C4 S C17 101.36(11) . . ?
C14 C1 C2 113.3(2) . . ?
C3 C2 C1 113.2(2) . . ?
C8 C3 C4 115.5(2) . . ?
C8 C3 C2 119.8(2) . . ?
C4 C3 C2 123.4(2) . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 S 118.21(18) . . ?
C3 C4 S 119.79(17) . . ?
C6 C5 C4 120.8(2) . . ?
C5 C6 C7 117.2(2) . . ?
C5 C6 C9 121.7(3) . . ?
C7 C6 C9 119.8(3) . . ?
C8 C7 C6 120.0(2) . . ?
C7 C8 C3 122.2(2) . . ?
C6 C9 C10 113.4(3) . . ?
C11 C10 C9 114.3(3) . . ?
C16 C11 C12 117.7(3) . . ?
C16 C11 C10 120.2(3) . . ?
C12 C11 C10 120.4(4) . . ?
C11 C12 C13 120.4(3) . . ?
C14 C13 C12 121.0(3) . . ?
C13 C14 C15 116.8(3) . . ?
C13 C14 C1 120.5(3) . . ?
C15 C14 C1 121.6(3) . . ?
C16 C15 C14 120.6(3) . . ?
C11 C16 C15 120.4(3) . . ?
C20 C17 C18 112.5(3) . . ?
C20 C17 C19 111.3(3) . . ?
C18 C17 C19 110.2(3) . . ?
C20 C17 S 109.1(2) . . ?
C18 C17 S 109.2(2) . . ?
C19 C17 S 104.1(2) . . ?
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 1.4943(18) . ?
S C4 1.796(2) . ?
S C17 1.857(2) . ?
C1 C14 1.507(4) . ?
C1 C2 1.577(5) . ?
C2 C3 1.509(4) . ?
C3 C8 1.391(4) . ?
C3 C4 1.399(3) . ?
C4 C5 1.388(3) . ?
C5 C6 1.391(4) . ?
C6 C7 1.391(4) . ?
C6 C9 1.511(4) . ?
C7 C8 1.380(4) . ?
C9 C10 1.537(5) . ?
C10 C11 1.526(5) . ?
C11 C16 1.377(5) . ?
C11 C12 1.387(4) . ?
C12 C13 1.392(4) . ?
C13 C14 1.375(4) . ?
C14 C15 1.396(4) . ?
C15 C16 1.392(5) . ?
C17 C20 1.518(4) . ?
C17 C18 1.523(4) . ?
C17 C19 1.527(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21141209
