#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/22/4022299.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_4022299
loop_
_publ_author_name
'Calum Macleod'
'Gordon J. McKiernan'
'Emma J. Guthrie'
'Louis J. Farrugia'
'Dieter W. Hamprecht'
'Jackie Macritchie'
'Richard C. Hartley'
_publ_section_title
;
 Synthesis of 2-Substituted Benzofurans and Indoles Using
 Functionalized Titanium Benzylidene Reagents on Solid Phase
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              387
_journal_page_last               401
_journal_paper_doi               10.1021/jo026384o
_journal_volume                  68
_journal_year                    2003
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H29 N O2 S2'
_chemical_formula_sum            'C20 H29 N O2 S2'
_chemical_formula_weight         379.56
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_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             2002-08-09T16:46:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 112.3080(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2187(2)
_cell_length_b                   9.1639(2)
_cell_length_c                   17.4445(3)
_cell_measurement_reflns_used    5913
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      2
_cell_measurement_wavelength     0.71073
_cell_volume                     2102.88(7)
_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      150(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      0.90632E-2
_diffrn_orient_matrix_UB_12      0.974232E-1
_diffrn_orient_matrix_UB_13      -0.220999E-1
_diffrn_orient_matrix_UB_21      0.8199E-3
_diffrn_orient_matrix_UB_22      0.476181E-1
_diffrn_orient_matrix_UB_23      0.518289E-1
_diffrn_orient_matrix_UB_31      0.754726E-1
_diffrn_orient_matrix_UB_32      -0.122164E-1
_diffrn_orient_matrix_UB_33      0.257807E-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  0.0406
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6127
_diffrn_reflns_reduction_process
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         2.41
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular flake cleaved from larger crystal'
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         6127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0415
_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)+(0.0454P)²+0.5722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                4407
_reflns_number_total             6127
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo026384o_s1_5.cif
_cod_data_source_block           cpd54a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022299
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_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
C2 C 0.63876(9) 0.94219(15) 0.71694(8) 0.0223(3) Uani 1 1 d .
H2 H 0.6413 0.8332 0.7197 0.027 Uiso 1 1 calc R
C6 C 0.47445(11) 0.91787(17) 0.76505(10) 0.0335(3) Uani 1 1 d .
H6A H 0.4861 0.8112 0.7703 0.04 Uiso 1 1 calc R
H6B H 0.4411 0.9461 0.8034 0.04 Uiso 1 1 calc R
C5 C 0.40246(11) 0.95171(18) 0.67689(10) 0.0349(3) Uani 1 1 d .
H5A H 0.3361 0.9045 0.6666 0.042 Uiso 1 1 calc R
H5B H 0.391 1.0584 0.6713 0.042 Uiso 1 1 calc R
C4 C 0.44132(10) 0.90072(17) 0.61133(9) 0.0328(3) Uani 1 1 d .
H4A H 0.3867 0.914 0.556 0.039 Uiso 1 1 calc R
H4B H 0.4566 0.7951 0.6191 0.039 Uiso 1 1 calc R
C1" C 0.77965(9) 0.65483(14) 0.70870(8) 0.0220(3) Uani 1 1 d .
C2" C 0.71799(10) 0.64070(15) 0.55729(8) 0.0234(3) Uani 1 1 d .
C6" C 0.85193(10) 0.69261(16) 0.85770(8) 0.0252(3) Uani 1 1 d .
H6"1 H 0.8055 0.6141 0.8605 0.03 Uiso 1 1 calc R
H6"2 H 0.8504 0.7711 0.8962 0.03 Uiso 1 1 calc R
C7" C 0.95776(11) 0.63309(16) 0.88476(8) 0.0276(3) Uani 1 1 d .
H7" H 0.969 0.5615 0.8498 0.033 Uiso 1 1 calc R
C8" C 1.03766(11) 0.66890(16) 0.95206(9) 0.0295(3) Uani 1 1 d .
C3" C 0.79056(12) 0.52211(18) 0.55317(10) 0.0368(4) Uani 1 1 d .
H3"1 H 0.8579 0.5645 0.5649 0.055 Uiso 1 1 calc R
H3"2 H 0.765 0.4787 0.4977 0.055 Uiso 1 1 calc R
H3"3 H 0.7956 0.4465 0.5943 0.055 Uiso 1 1 calc R
C4" C 0.61445(11) 0.5801(2) 0.54577(10) 0.0412(4) Uani 1 1 d .
H4"1 H 0.6222 0.502 0.5861 0.062 Uiso 1 1 calc R
H4"2 H 0.5818 0.5411 0.4895 0.062 Uiso 1 1 calc R
H4"3 H 0.5722 0.6581 0.5543 0.062 Uiso 1 1 calc R
C5" C 0.70752(13) 0.75871(17) 0.49410(9) 0.0360(4) Uani 1 1 d .
H5"1 H 0.6624 0.8356 0.4993 0.054 Uiso 1 1 calc R
H5"2 H 0.6788 0.7168 0.4383 0.054 Uiso 1 1 calc R
H5"3 H 0.7746 0.8003 0.5037 0.054 Uiso 1 1 calc R
C10" C 1.13991(12) 0.6008(2) 0.96924(11) 0.0455(4) Uani 1 1 d .
H10A H 1.1346 0.5309 0.9252 0.068 Uiso 1 1 calc R
H10B H 1.1628 0.55 1.0226 0.068 Uiso 1 1 calc R
H10C H 1.189 0.6771 0.971 0.068 Uiso 1 1 calc R
C9" C 1.03487(14) 0.7745(2) 1.01635(11) 0.0471(4) Uani 1 1 d .
H9"1 H 0.9729 0.8335 0.9939 0.071 Uiso 1 1 calc R
H9"2 H 1.0945 0.8384 1.0323 0.071 Uiso 1 1 calc R
H9"3 H 1.0354 0.7208 1.0651 0.071 Uiso 1 1 calc R
C2' C 0.82906(9) 0.90409(14) 0.76190(8) 0.0197(3) Uani 1 1 d .
C1' C 0.74475(9) 0.99838(14) 0.73551(8) 0.0206(2) Uani 1 1 d .
C6' C 0.76150(10) 1.14723(15) 0.72929(8) 0.0253(3) Uani 1 1 d .
H6' H 0.7052 1.2121 0.7106 0.03 Uiso 1 1 calc R
C5' C 0.85892(10) 1.20211(15) 0.74989(8) 0.0272(3) Uani 1 1 d .
H5' H 0.8691 1.3038 0.7456 0.033 Uiso 1 1 calc R
C4' C 0.94134(10) 1.10791(15) 0.77678(8) 0.0265(3) Uani 1 1 d .
H4' H 1.0082 1.1453 0.7915 0.032 Uiso 1 1 calc R
C3' C 0.92654(10) 0.95942(15) 0.78234(8) 0.0236(3) Uani 1 1 d .
H3' H 0.9833 0.8952 0.8002 0.028 Uiso 1 1 calc R
N1 N 0.81570(8) 0.75126(11) 0.77257(6) 0.0206(2) Uani 1 1 d .
O1 O 0.76593(8) 0.52553(10) 0.71767(6) 0.0311(2) Uani 1 1 d .
O2 O 0.76196(7) 0.72184(10) 0.63613(5) 0.0237(2) Uani 1 1 d .
S1 S 0.59677(3) 1.00929(4) 0.79712(2) 0.02810(9) Uani 1 1 d .
S3 S 0.55419(3) 0.99592(4) 0.61346(2) 0.02863(10) Uani 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'
N N 0.0061 0.0033 '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
C1' C2 S3 110.60(9)
C1' C2 S1 108.17(9)
S3 C2 S1 112.64(7)
C1' C2 H2 108.4
S3 C2 H2 108.4
S1 C2 H2 108.4
C5 C6 S1 114.55(10)
C5 C6 H6A 108.6
S1 C6 H6A 108.6
C5 C6 H6B 108.6
S1 C6 H6B 108.6
H6A C6 H6B 107.6
C4 C5 C6 113.62(12)
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 C4 S3 114.08(11)
C5 C4 H4A 108.7
S3 C4 H4A 108.7
C5 C4 H4B 108.7
S3 C4 H4B 108.7
H4A C4 H4B 107.6
O1 C1" O2 125.68(12)
O1 C1" N1 123.67(12)
O2 C1" N1 110.65(11)
O2 C2" C5" 102.04(10)
O2 C2" C4" 110.78(11)
C5" C2" C4" 110.13(13)
O2 C2" C3" 110.43(11)
C5" C2" C3" 110.99(12)
C4" C2" C3" 112.04(13)
N1 C6" C7" 112.01(10)
N1 C6" H6"1 109.2
C7" C6" H6"1 109.2
N1 C6" H6"2 109.2
C7" C6" H6"2 109.2
H6"1 C6" H6"2 107.9
C8" C7" C6" 127.46(13)
C8" C7" H7" 116.3
C6" C7" H7" 116.3
C7" C8" C9" 124.50(14)
C7" C8" C10" 120.75(15)
C9" C8" C10" 114.74(14)
C2" C3" H3"1 109.5
C2" C3" H3"2 109.5
H3"1 C3" H3"2 109.5
C2" C3" H3"3 109.5
H3"1 C3" H3"3 109.5
H3"2 C3" H3"3 109.5
C2" C4" H4"1 109.5
C2" C4" H4"2 109.5
H4"1 C4" H4"2 109.5
C2" C4" H4"3 109.5
H4"1 C4" H4"3 109.5
H4"2 C4" H4"3 109.5
C2" C5" H5"1 109.5
C2" C5" H5"2 109.5
H5"1 C5" H5"2 109.5
C2" C5" H5"3 109.5
H5"1 C5" H5"3 109.5
H5"2 C5" H5"3 109.5
C8" C10" H10A 109.5
C8" C10" H10B 109.5
H10A C10" H10B 109.5
C8" C10" H10C 109.5
H10A C10" H10C 109.5
H10B C10" H10C 109.5
C8" C9" H9"1 109.5
C8" C9" H9"2 109.5
H9"1 C9" H9"2 109.5
C8" C9" H9"3 109.5
H9"1 C9" H9"3 109.5
H9"2 C9" H9"3 109.5
C3' C2' C1' 120.22(12)
C3' C2' N1 119.43(11)
C1' C2' N1 120.26(11)
C6' C1' C2' 118.46(12)
C6' C1' C2 120.22(11)
C2' C1' C2 121.29(11)
C5' C6' C1' 121.15(12)
C5' C6' H6' 119.4
C1' C6' H6' 119.4
C4' C5' C6' 119.66(13)
C4' C5' H5' 120.2
C6' C5' H5' 120.2
C3' C4' C5' 120.25(13)
C3' C4' H4' 119.9
C5' C4' H4' 119.9
C4' C3' C2' 120.24(12)
C4' C3' H3' 119.9
C2' C3' H3' 119.9
C1" N1 C2' 123.70(11)
C1" N1 C6" 117.80(11)
C2' N1 C6" 118.23(11)
C1" O2 C2" 120.62(10)
C6 S1 C2 99.34(7)
C4 S3 C2 97.86(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 C1' 1.5069(18)
C2 S3 1.8163(13)
C2 S1 1.8233(13)
C2 H2 1
C6 C5 1.521(2)
C6 S1 1.8169(15)
C6 H6A 0.99
C6 H6B 0.99
C5 C4 1.520(2)
C5 H5A 0.99
C5 H5B 0.99
C4 S3 1.8145(15)
C4 H4A 0.99
C4 H4B 0.99
C1" O1 1.2204(16)
C1" O2 1.3421(15)
C1" N1 1.3607(17)
C2" O2 1.4774(15)
C2" C5" 1.5107(19)
C2" C4" 1.5135(19)
C2" C3" 1.519(2)
C6" N1 1.4760(16)
C6" C7" 1.4986(19)
C6" H6"1 0.99
C6" H6"2 0.99
C7" C8" 1.328(2)
C7" H7" 0.95
C8" C9" 1.493(2)
C8" C10" 1.504(2)
C3" H3"1 0.98
C3" H3"2 0.98
C3" H3"3 0.98
C4" H4"1 0.98
C4" H4"2 0.98
C4" H4"3 0.98
C5" H5"1 0.98
C5" H5"2 0.98
C5" H5"3 0.98
C10" H10A 0.98
C10" H10B 0.98
C10" H10C 0.98
C9" H9"1 0.98
C9" H9"2 0.98
C9" H9"3 0.98
C2' C3' 1.3893(18)
C2' C1' 1.4060(17)
C2' N1 1.4349(16)
C1' C6' 1.3960(18)
C6' C5' 1.3867(19)
C6' H6' 0.95
C5' C4' 1.386(2)
C5' H5' 0.95
C4' C3' 1.386(2)
C4' H4' 0.95
C3' H3' 0.95
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
S1 C6 C5 C4 63.50(16)
C6 C5 C4 S3 -66.27(16)
N1 C6" C7" C8" 125.39(15)
C6" C7" C8" C9" 2.5(2)
C6" C7" C8" C10" -178.58(14)
C3' C2' C1' C6' 0.96(19)
N1 C2' C1' C6' 177.31(12)
C3' C2' C1' C2 -177.01(12)
N1 C2' C1' C2 -0.65(18)
S3 C2 C1' C6' 56.10(15)
S1 C2 C1' C6' -67.69(14)
S3 C2 C1' C2' -125.97(11)
S1 C2 C1' C2' 110.24(12)
C2' C1' C6' C5' -1.1(2)
C2 C1' C6' C5' 176.89(12)
C1' C6' C5' C4' 0.3(2)
C6' C5' C4' C3' 0.6(2)
C5' C4' C3' C2' -0.7(2)
C1' C2' C3' C4' -0.06(19)
N1 C2' C3' C4' -176.44(12)
O1 C1" N1 C2' -178.12(12)
O2 C1" N1 C2' 1.92(16)
O1 C1" N1 C6" 7.81(19)
O2 C1" N1 C6" -172.15(10)
C3' C2' N1 C1" -106.32(14)
C1' C2' N1 C1" 77.30(16)
C3' C2' N1 C6" 67.73(15)
C1' C2' N1 C6" -108.65(13)
C7" C6" N1 C1" 80.73(14)
C7" C6" N1 C2' -93.67(14)
O1 C1" O2 C2" 2.83(19)
N1 C1" O2 C2" -177.21(10)
C5" C2" O2 C1" 177.51(11)
C4" C2" O2 C1" 60.30(15)
C3" C2" O2 C1" -64.43(15)
C5 C6 S1 C2 -57.40(12)
C1' C2 S1 C6 -176.24(9)
S3 C2 S1 C6 61.20(9)
C5 C4 S3 C2 61.79(12)
C1' C2 S3 C4 176.12(10)
S1 C2 S3 C4 -62.70(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9200477
