#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/37/4023773.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_4023773
loop_
_publ_author_name
'Detian Gao'
'Huimin Zhai'
'Masood Parvez'
'Thomas G. Back'
_publ_section_title
;
 1,3-Dipolar Cycloadditions of Acetylenic Sulfones in Solution
 and on Solid Supports
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8057
_journal_page_last               8068
_journal_paper_doi               10.1021/jo801621d
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C20 H27 N O3 S'
_chemical_formula_weight         361.49
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.23(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.585(3)
_cell_length_b                   22.167(10)
_cell_length_c                   10.125(4)
_cell_measurement_temperature    173(2)
_cell_volume                     1859.2(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0586
_diffrn_reflns_av_sigmaI/netI    0.0780
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8228
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.5900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                2479
_reflns_number_total             4245
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801621d_si_007.cif
_cod_data_source_block           tim1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023773
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.83324(8) 0.14298(3) -0.10042(6) 0.0351(2) Uani 1 1 d . . .
O1 O 0.9873(2) 0.11347(8) -0.08080(18) 0.0424(5) Uani 1 1 d . . .
O2 O 0.7261(2) 0.14277(8) -0.23728(16) 0.0414(5) Uani 1 1 d . . .
O3 O 0.8337(2) 0.43601(9) 0.07079(19) 0.0524(5) Uani 1 1 d . . .
H3 H 0.7871 0.4193 0.1244 0.063 Uiso 1 1 calc R . .
N1 N 0.6653(2) 0.05276(9) 0.16066(19) 0.0320(5) Uani 1 1 d . . .
C1 C 0.6690(3) 0.00243(12) 0.2559(3) 0.0398(6) Uani 1 1 d . . .
H1A H 0.7715 0.0035 0.3290 0.048 Uiso 1 1 calc R . .
H1B H 0.6641 -0.0363 0.2063 0.048 Uiso 1 1 calc R . .
C2 C 0.5282(3) 0.00651(15) 0.3191(3) 0.0559(8) Uani 1 1 d . . .
H2A H 0.5173 -0.0323 0.3640 0.067 Uiso 1 1 calc R . .
H2B H 0.5511 0.0382 0.3906 0.067 Uiso 1 1 calc R . .
C3 C 0.3737(4) 0.02060(15) 0.2182(3) 0.0595(9) Uani 1 1 d . . .
H3A H 0.2865 0.0219 0.2655 0.071 Uiso 1 1 calc R . .
H3B H 0.3480 -0.0121 0.1492 0.071 Uiso 1 1 calc R . .
C4 C 0.3782(3) 0.07965(13) 0.1467(3) 0.0419(7) Uani 1 1 d . . .
H4A H 0.2839 0.0822 0.0659 0.050 Uiso 1 1 calc R . .
H4B H 0.3703 0.1131 0.2093 0.050 Uiso 1 1 calc R . .
C5 C 0.5300(3) 0.08676(11) 0.1014(2) 0.0321(6) Uani 1 1 d . . .
C6 C 0.5656(3) 0.12515(11) 0.0077(2) 0.0311(6) Uani 1 1 d . . .
C7 C 0.7315(3) 0.11302(11) 0.0107(2) 0.0316(6) Uani 1 1 d . . .
C8 C 0.7897(3) 0.06804(11) 0.1064(2) 0.0323(6) Uani 1 1 d . . .
C9 C 0.9498(3) 0.03762(13) 0.1550(3) 0.0444(7) Uani 1 1 d . . .
H9A H 1.0290 0.0582 0.1165 0.053 Uiso 1 1 calc R . .
H9B H 0.9401 -0.0046 0.1252 0.053 Uiso 1 1 calc R . .
H9C H 0.9854 0.0393 0.2552 0.053 Uiso 1 1 calc R . .
C10 C 0.4531(3) 0.17186(11) -0.0728(2) 0.0352(6) Uani 1 1 d . . .
H10A H 0.3416 0.1559 -0.0950 0.042 Uiso 1 1 calc R . .
H10B H 0.4814 0.1790 -0.1602 0.042 Uiso 1 1 calc R . .
C11 C 0.4579(3) 0.23199(11) 0.0021(2) 0.0352(6) Uani 1 1 d . . .
H11A H 0.4286 0.2249 0.0891 0.042 Uiso 1 1 calc R . .
H11B H 0.5698 0.2477 0.0251 0.042 Uiso 1 1 calc R . .
C12 C 0.3456(3) 0.27937(12) -0.0798(3) 0.0403(6) Uani 1 1 d . . .
H12A H 0.2327 0.2653 -0.0955 0.048 Uiso 1 1 calc R . .
H12B H 0.3682 0.2839 -0.1703 0.048 Uiso 1 1 calc R . .
C13 C 0.3624(3) 0.34052(13) -0.0096(3) 0.0484(7) Uani 1 1 d . . .
H13A H 0.2847 0.3688 -0.0656 0.058 Uiso 1 1 calc R . .
H13B H 0.4722 0.3558 0.0015 0.058 Uiso 1 1 calc R . .
H13C H 0.3413 0.3364 0.0805 0.058 Uiso 1 1 calc R . .
C14 C 0.8720(3) 0.21928(11) -0.0527(2) 0.0312(6) Uani 1 1 d . . .
C15 C 0.7998(3) 0.26536(12) -0.1395(3) 0.0385(6) Uani 1 1 d . . .
H15 H 0.7271 0.2564 -0.2255 0.046 Uiso 1 1 calc R . .
C16 C 0.8342(3) 0.32458(12) -0.0999(3) 0.0397(6) Uani 1 1 d . . .
H16 H 0.7846 0.3562 -0.1595 0.048 Uiso 1 1 calc R . .
C17 C 0.9404(3) 0.33871(12) 0.0258(3) 0.0359(6) Uani 1 1 d . . .
C18 C 1.0111(3) 0.29177(12) 0.1112(3) 0.0388(6) Uani 1 1 d . . .
H18 H 1.0832 0.3007 0.1976 0.047 Uiso 1 1 calc R . .
C19 C 0.9785(3) 0.23232(12) 0.0731(2) 0.0382(6) Uani 1 1 d . . .
H19 H 1.0284 0.2006 0.1323 0.046 Uiso 1 1 calc R . .
C20 C 0.9756(3) 0.40319(13) 0.0700(3) 0.0457(7) Uani 1 1 d . . .
H20A H 1.0501 0.4039 0.1630 0.055 Uiso 1 1 calc R . .
H20B H 1.0304 0.4232 0.0072 0.055 Uiso 1 1 calc R . .
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'
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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
O1 S1 O2 117.36(11) . . ?
O1 S1 C7 109.76(11) . . ?
O2 S1 C7 108.60(11) . . ?
O1 S1 C14 107.26(11) . . ?
O2 S1 C14 106.95(11) . . ?
C7 S1 C14 106.33(11) . . ?
C20 O3 H3 109.5 . . ?
C8 N1 C5 110.3(2) . . ?
C8 N1 C1 124.6(2) . . ?
C5 N1 C1 124.7(2) . . ?
N1 C1 C2 110.5(2) . . ?
N1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C3 C2 C1 113.1(2) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 112.6(2) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 112.0(2) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 N1 108.9(2) . . ?
C6 C5 C4 130.4(2) . . ?
N1 C5 C4 120.6(2) . . ?
C5 C6 C7 105.6(2) . . ?
C5 C6 C10 125.2(2) . . ?
C7 C6 C10 129.1(2) . . ?
C8 C7 C6 108.7(2) . . ?
C8 C7 S1 125.41(19) . . ?
C6 C7 S1 125.46(18) . . ?
N1 C8 C7 106.4(2) . . ?
N1 C8 C9 120.3(2) . . ?
C7 C8 C9 133.3(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 C11 113.71(19) . . ?
C6 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C6 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C10 113.7(2) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 113.1(2) . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 120.4(2) . . ?
C15 C14 S1 120.85(19) . . ?
C19 C14 S1 118.77(19) . . ?
C16 C15 C14 119.4(2) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 121.2(2) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 118.4(2) . . ?
C18 C17 C20 120.4(2) . . ?
C16 C17 C20 121.2(2) . . ?
C19 C18 C17 121.2(2) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C14 119.4(2) . . ?
C18 C19 H19 120.3 . . ?
C14 C19 H19 120.3 . . ?
O3 C20 C17 112.5(2) . . ?
O3 C20 H20A 109.1 . . ?
C17 C20 H20A 109.1 . . ?
O3 C20 H20B 109.1 . . ?
C17 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
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
S1 O1 1.4416(18) . ?
S1 O2 1.4480(18) . ?
S1 C7 1.728(3) . ?
S1 C14 1.766(3) . ?
O3 C20 1.420(3) . ?
O3 H3 0.8400 . ?
N1 C8 1.366(3) . ?
N1 C5 1.383(3) . ?
N1 C1 1.470(3) . ?
C1 C2 1.511(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.480(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.501(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.498(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.367(3) . ?
C6 C7 1.442(3) . ?
C6 C10 1.502(3) . ?
C7 C8 1.388(3) . ?
C8 C9 1.494(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.529(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.517(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.520(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.383(3) . ?
C14 C19 1.389(3) . ?
C15 C16 1.382(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(4) . ?
C17 C20 1.504(4) . ?
C18 C19 1.381(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O2 0.84 2.13 2.937(3) 162.3 4_566
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 167.7(2) . . . . ?
C5 N1 C1 C2 -20.1(3) . . . . ?
N1 C1 C2 C3 44.8(3) . . . . ?
C1 C2 C3 C4 -59.8(4) . . . . ?
C2 C3 C4 C5 45.1(4) . . . . ?
C8 N1 C5 C6 -0.4(3) . . . . ?
C1 N1 C5 C6 -173.6(2) . . . . ?
C8 N1 C5 C4 -178.2(2) . . . . ?
C1 N1 C5 C4 8.6(4) . . . . ?
C3 C4 C5 C6 162.5(3) . . . . ?
C3 C4 C5 N1 -20.1(3) . . . . ?
N1 C5 C6 C7 0.4(3) . . . . ?
C4 C5 C6 C7 178.0(2) . . . . ?
N1 C5 C6 C10 -176.5(2) . . . . ?
C4 C5 C6 C10 1.1(4) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C10 C6 C7 C8 176.5(2) . . . . ?
C5 C6 C7 S1 172.69(18) . . . . ?
C10 C6 C7 S1 -10.6(4) . . . . ?
O1 S1 C7 C8 1.0(3) . . . . ?
O2 S1 C7 C8 130.5(2) . . . . ?
C14 S1 C7 C8 -114.7(2) . . . . ?
O1 S1 C7 C6 -170.8(2) . . . . ?
O2 S1 C7 C6 -41.3(2) . . . . ?
C14 S1 C7 C6 73.5(2) . . . . ?
C5 N1 C8 C7 0.2(3) . . . . ?
C1 N1 C8 C7 173.4(2) . . . . ?
C5 N1 C8 C9 179.6(2) . . . . ?
C1 N1 C8 C9 -7.3(4) . . . . ?
C6 C7 C8 N1 0.0(3) . . . . ?
S1 C7 C8 N1 -172.93(17) . . . . ?
C6 C7 C8 C9 -179.2(3) . . . . ?
S1 C7 C8 C9 7.8(4) . . . . ?
C5 C6 C10 C11 86.1(3) . . . . ?
C7 C6 C10 C11 -90.1(3) . . . . ?
C6 C10 C11 C12 179.4(2) . . . . ?
C10 C11 C12 C13 -174.8(2) . . . . ?
O1 S1 C14 C15 128.7(2) . . . . ?
O2 S1 C14 C15 2.0(2) . . . . ?
C7 S1 C14 C15 -113.9(2) . . . . ?
O1 S1 C14 C19 -50.4(2) . . . . ?
O2 S1 C14 C19 -177.12(19) . . . . ?
C7 S1 C14 C19 67.0(2) . . . . ?
C19 C14 C15 C16 -0.1(4) . . . . ?
S1 C14 C15 C16 -179.2(2) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C15 C16 C17 C20 -178.8(2) . . . . ?
C16 C17 C18 C19 0.5(4) . . . . ?
C20 C17 C18 C19 179.1(2) . . . . ?
C17 C18 C19 C14 -0.5(4) . . . . ?
C15 C14 C19 C18 0.3(4) . . . . ?
S1 C14 C19 C18 179.4(2) . . . . ?
C18 C17 C20 O3 -122.0(3) . . . . ?
C16 C17 C20 O3 56.6(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658775
