#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/37/4023767.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_4023767
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 H23 N3 O3 S'
_chemical_formula_weight         385.47
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 107.790(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.325(8)
_cell_length_b                   7.976(2)
_cell_length_c                   16.450(7)
_cell_measurement_temperature    173(2)
_cell_volume                     1914.6(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7693
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_correction_T_min  0.9621
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0466
_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)+(0.0460P)²+0.5600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1127
_reflns_number_gt                3077
_reflns_number_total             4377
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801621d_si_001.cif
_cod_data_source_block           t2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023767
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.50896(4) 0.15329(5) 0.24679(3) 0.02860(15) Uani 1 1 d . . .
O1 O 0.55337(10) -0.00709(15) 0.25466(8) 0.0399(4) Uani 1 1 d . . .
O2 O 0.43435(10) 0.17723(18) 0.28108(8) 0.0373(4) Uani 1 1 d . . .
O3 O 0.32174(9) 0.49412(15) -0.14576(8) 0.0337(3) Uani 1 1 d . . .
H03 H 0.2738 0.4362 -0.1621 0.050 Uiso 1 1 calc R . .
N1 N 0.67018(11) 0.52475(18) 0.33864(9) 0.0265(4) Uani 1 1 d . . .
N2 N 0.73151(11) 0.40059(19) 0.34184(10) 0.0307(4) Uani 1 1 d . . .
N3 N 0.68436(11) 0.26458(19) 0.31352(9) 0.0304(4) Uani 1 1 d . . .
C1 C 0.78086(14) 0.6207(3) 0.52254(12) 0.0343(5) Uani 1 1 d . . .
H1 H 0.8181 0.5421 0.5051 0.041 Uiso 1 1 calc R . .
C2 C 0.78971(16) 0.6391(3) 0.60846(13) 0.0453(6) Uani 1 1 d . . .
H2 H 0.8336 0.5743 0.6498 0.054 Uiso 1 1 calc R . .
C3 C 0.73485(17) 0.7511(3) 0.63398(13) 0.0469(6) Uani 1 1 d . . .
H3 H 0.7403 0.7621 0.6928 0.056 Uiso 1 1 calc R . .
C4 C 0.67227(17) 0.8469(3) 0.57444(14) 0.0439(6) Uani 1 1 d . . .
H4 H 0.6346 0.9241 0.5923 0.053 Uiso 1 1 calc R . .
C5 C 0.66394(15) 0.8313(2) 0.48836(13) 0.0354(5) Uani 1 1 d . . .
H5 H 0.6213 0.8991 0.4475 0.042 Uiso 1 1 calc R . .
C6 C 0.71777(13) 0.7168(2) 0.46180(12) 0.0273(4) Uani 1 1 d . . .
C7 C 0.70537(14) 0.6931(2) 0.36770(12) 0.0297(4) Uani 1 1 d . . .
H7A H 0.6621 0.7784 0.3346 0.036 Uiso 1 1 calc R . .
H7B H 0.7649 0.7098 0.3570 0.036 Uiso 1 1 calc R . .
C8 C 0.58261(13) 0.4692(2) 0.30888(10) 0.0240(4) Uani 1 1 d . . .
C9 C 0.59350(13) 0.3016(2) 0.29308(11) 0.0258(4) Uani 1 1 d . . .
C10 C 0.50021(13) 0.5759(2) 0.30052(11) 0.0283(4) Uani 1 1 d . . .
H10A H 0.4488 0.5343 0.2522 0.034 Uiso 1 1 calc R . .
H10B H 0.5137 0.6923 0.2872 0.034 Uiso 1 1 calc R . .
C11 C 0.47097(13) 0.5765(2) 0.38153(11) 0.0293(4) Uani 1 1 d . . .
H11A H 0.4524 0.4616 0.3920 0.035 Uiso 1 1 calc R . .
H11B H 0.5241 0.6085 0.4307 0.035 Uiso 1 1 calc R . .
C12 C 0.39255(15) 0.6957(3) 0.37628(13) 0.0388(5) Uani 1 1 d . . .
H12A H 0.3362 0.6525 0.3341 0.047 Uiso 1 1 calc R . .
H12B H 0.4066 0.8064 0.3561 0.047 Uiso 1 1 calc R . .
C13 C 0.37553(16) 0.7166(3) 0.46227(14) 0.0440(6) Uani 1 1 d . . .
H13A H 0.3220 0.7887 0.4555 0.053 Uiso 1 1 calc R . .
H13B H 0.4294 0.7681 0.5030 0.053 Uiso 1 1 calc R . .
H13C H 0.3643 0.6066 0.4837 0.053 Uiso 1 1 calc R . .
C14 C 0.47188(13) 0.2123(2) 0.13842(11) 0.0237(4) Uani 1 1 d . . .
C15 C 0.39347(13) 0.3091(2) 0.10706(12) 0.0278(4) Uani 1 1 d . . .
H15 H 0.3570 0.3367 0.1427 0.033 Uiso 1 1 calc R . .
C16 C 0.36875(13) 0.3654(2) 0.02313(11) 0.0269(4) Uani 1 1 d . . .
H16 H 0.3151 0.4314 0.0013 0.032 Uiso 1 1 calc R . .
C17 C 0.42183(13) 0.3258(2) -0.02904(11) 0.0239(4) Uani 1 1 d . . .
C18 C 0.49951(14) 0.2274(2) 0.00361(12) 0.0286(4) Uani 1 1 d . . .
H18 H 0.5357 0.1990 -0.0321 0.034 Uiso 1 1 calc R . .
C19 C 0.52542(13) 0.1699(2) 0.08700(11) 0.0277(4) Uani 1 1 d . . .
H19 H 0.5787 0.1028 0.1086 0.033 Uiso 1 1 calc R . .
C20 C 0.39880(14) 0.3872(2) -0.12002(11) 0.0297(4) Uani 1 1 d . . .
H20A H 0.4525 0.4477 -0.1268 0.036 Uiso 1 1 calc R . .
H20B H 0.3875 0.2889 -0.1586 0.036 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
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
O2 S1 O1 119.74(9) . . ?
O2 S1 C9 108.22(9) . . ?
O1 S1 C9 107.20(9) . . ?
O2 S1 C14 108.24(9) . . ?
O1 S1 C14 109.06(9) . . ?
C9 S1 C14 103.13(8) . . ?
C20 O3 H03 109.5 . . ?
C8 N1 N2 111.94(15) . . ?
C8 N1 C7 129.81(16) . . ?
N2 N1 C7 118.24(16) . . ?
N3 N2 N1 106.93(15) . . ?
N2 N3 C9 108.69(15) . . ?
C2 C1 C6 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.13(19) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 119.11(18) . . ?
C5 C6 C7 120.23(17) . . ?
C1 C6 C7 120.63(18) . . ?
N1 C7 C6 111.44(14) . . ?
N1 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 C9 102.78(16) . . ?
N1 C8 C10 124.27(16) . . ?
C9 C8 C10 132.93(17) . . ?
N3 C9 C8 109.66(16) . . ?
N3 C9 S1 121.81(13) . . ?
C8 C9 S1 128.37(15) . . ?
C8 C10 C11 112.69(15) . . ?
C8 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C8 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 113.00(16) . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 111.97(17) . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
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 . . ?
C19 C14 C15 120.96(16) . . ?
C19 C14 S1 118.93(14) . . ?
C15 C14 S1 119.97(14) . . ?
C14 C15 C16 119.41(18) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 120.52(17) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 118.97(16) . . ?
C16 C17 C20 122.39(17) . . ?
C18 C17 C20 118.64(17) . . ?
C19 C18 C17 121.51(18) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C14 118.62(17) . . ?
C18 C19 H19 120.7 . . ?
C14 C19 H19 120.7 . . ?
O3 C20 C17 114.43(16) . . ?
O3 C20 H20A 108.7 . . ?
C17 C20 H20A 108.7 . . ?
O3 C20 H20B 108.7 . . ?
C17 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
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 O2 1.4339(16) . ?
S1 O1 1.4362(14) . ?
S1 C9 1.7477(19) . ?
S1 C14 1.7615(19) . ?
O3 C20 1.413(2) . ?
O3 H03 0.8400 . ?
N1 C8 1.355(2) . ?
N1 N2 1.355(2) . ?
N1 C7 1.471(2) . ?
N2 N3 1.308(2) . ?
N3 C9 1.361(2) . ?
C1 C2 1.386(3) . ?
C1 C6 1.389(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.377(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.513(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.382(2) . ?
C8 C10 1.494(3) . ?
C10 C11 1.530(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.514(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.524(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.388(3) . ?
C14 C15 1.389(3) . ?
C15 C16 1.390(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(3) . ?
C17 C20 1.510(2) . ?
C18 C19 1.385(3) . ?
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 H03 N3 0.84 2.07 2.877(2) 162.3 4_565
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 N2 N3 0.60(19) . . . . ?
C7 N1 N2 N3 179.67(14) . . . . ?
N1 N2 N3 C9 -0.50(19) . . . . ?
C6 C1 C2 C3 1.0(3) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C4 C5 C6 C7 176.80(18) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C1 C6 C7 -177.81(18) . . . . ?
C8 N1 C7 C6 88.2(2) . . . . ?
N2 N1 C7 C6 -90.7(2) . . . . ?
C5 C6 C7 N1 -113.8(2) . . . . ?
C1 C6 C7 N1 64.1(2) . . . . ?
N2 N1 C8 C9 -0.43(19) . . . . ?
C7 N1 C8 C9 -179.36(16) . . . . ?
N2 N1 C8 C10 178.18(15) . . . . ?
C7 N1 C8 C10 -0.8(3) . . . . ?
N2 N3 C9 C8 0.3(2) . . . . ?
N2 N3 C9 S1 176.03(12) . . . . ?
N1 C8 C9 N3 0.11(19) . . . . ?
C10 C8 C9 N3 -178.32(17) . . . . ?
N1 C8 C9 S1 -175.31(14) . . . . ?
C10 C8 C9 S1 6.3(3) . . . . ?
O2 S1 C9 N3 143.08(15) . . . . ?
O1 S1 C9 N3 12.65(17) . . . . ?
C14 S1 C9 N3 -102.39(16) . . . . ?
O2 S1 C9 C8 -41.99(19) . . . . ?
O1 S1 C9 C8 -172.42(16) . . . . ?
C14 S1 C9 C8 72.54(18) . . . . ?
N1 C8 C10 C11 -89.1(2) . . . . ?
C9 C8 C10 C11 89.0(2) . . . . ?
C8 C10 C11 C12 175.12(16) . . . . ?
C10 C11 C12 C13 -170.20(17) . . . . ?
O2 S1 C14 C19 -167.48(14) . . . . ?
O1 S1 C14 C19 -35.68(17) . . . . ?
C9 S1 C14 C19 78.01(16) . . . . ?
O2 S1 C14 C15 16.74(17) . . . . ?
O1 S1 C14 C15 148.54(15) . . . . ?
C9 S1 C14 C15 -97.77(16) . . . . ?
C19 C14 C15 C16 -0.5(3) . . . . ?
S1 C14 C15 C16 175.20(13) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C15 C16 C17 C20 -178.65(16) . . . . ?
C16 C17 C18 C19 -0.7(3) . . . . ?
C20 C17 C18 C19 178.72(17) . . . . ?
C17 C18 C19 C14 0.1(3) . . . . ?
C15 C14 C19 C18 0.5(3) . . . . ?
S1 C14 C19 C18 -175.20(14) . . . . ?
C16 C17 C20 O3 2.9(2) . . . . ?
C18 C17 C20 O3 -176.50(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658772
