#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/28/1502893.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_1502893
loop_
_publ_author_name
'Li, Qian'
'Jiang, Guo-Jie'
'Jiao, Lei'
'Yu, Zhi-Xiang'
_publ_section_title
;
 Reaction of alpha-ene-vinylcyclopropanes: type II intramolecular [5+2]
 cycloaddition or [3+2] cycloaddition?
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1332
_journal_page_last               1335
_journal_paper_doi               10.1021/ol100237h
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C17 H21 N O2 S'
_chemical_formula_weight         303.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                78.21(3)
_cell_angle_beta                 86.73(3)
_cell_angle_gamma                65.64(3)
_cell_formula_units_Z            2
_cell_length_a                   8.4158(17)
_cell_length_b                   9.0268(18)
_cell_length_c                   11.505(2)
_cell_measurement_reflns_used    6376
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.81
_cell_volume                     779.0(3)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_molecular_graphics
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6376
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.9182
_exptl_absorpt_correction_T_min  0.8573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR by T.Higashi    8 March, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.59
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3552
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.199
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0468P)²+0.5930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1252
_reflns_number_gt                3275
_reflns_number_total             3552
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100237h_si_003.cif
_cod_data_source_block           sx2701
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502893
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
S1 S 0.21064(6) 0.85177(6) 0.69538(4) 0.01936(14) Uani 1 1 d .
O1 O 0.1353(2) 0.98780(18) 0.59719(13) 0.0274(3) Uani 1 1 d .
O2 O 0.35168(19) 0.84218(19) 0.76485(13) 0.0264(3) Uani 1 1 d .
N1 N 0.0516(2) 0.85837(19) 0.78851(14) 0.0189(3) Uani 1 1 d .
C1 C 0.1062(2) 0.7360(2) 0.90186(16) 0.0187(4) Uani 1 1 d .
H1A H 0.2058 0.7438 0.9379 0.022 Uiso 1 1 calc R
H1B H 0.1466 0.6229 0.8853 0.022 Uiso 1 1 calc R
C2 C -0.0393(2) 0.7620(2) 0.98998(16) 0.0182(4) Uani 1 1 d .
C3 C -0.2231(2) 0.8265(2) 0.93754(17) 0.0194(4) Uani 1 1 d .
C4 C -0.2377(3) 0.8689(2) 0.80573(18) 0.0229(4) Uani 1 1 d .
H4A H -0.3428 0.8846 0.7683 0.027 Uiso 1 1 calc R
C5 C -0.1110(3) 0.8859(2) 0.73743(17) 0.0230(4) Uani 1 1 d .
H5A H -0.1291 0.9168 0.6536 0.028 Uiso 1 1 calc R
C6 C 0.0198(3) 0.6274(3) 1.09968(17) 0.0219(4) Uani 1 1 d .
H6A H 0.0419 0.5150 1.0853 0.026 Uiso 1 1 calc R
C7 C -0.0391(3) 0.6514(3) 1.22247(19) 0.0346(5) Uani 1 1 d .
H7A H -0.1206 0.7640 1.2323 0.041 Uiso 1 1 calc R
H7B H -0.0571 0.5596 1.2766 0.041 Uiso 1 1 calc R
C8 C 0.1438(3) 0.6247(4) 1.1897(2) 0.0384(6) Uani 1 1 d .
H8A H 0.2386 0.5164 1.2235 0.046 Uiso 1 1 calc R
H8B H 0.1750 0.7209 1.1792 0.046 Uiso 1 1 calc R
C9 C -0.1674(3) 0.9351(2) 0.99596(18) 0.0234(4) Uani 1 1 d .
H9A H -0.1494 1.0284 0.9437 0.028 Uiso 1 1 calc R
H9B H -0.2153 0.9570 1.0743 0.028 Uiso 1 1 calc R
C10 C -0.3543(3) 0.7640(3) 0.99872(19) 0.0256(4) Uani 1 1 d .
H10A H -0.4650 0.8189 0.9528 0.038 Uiso 1 1 calc R
H10B H -0.3734 0.7888 1.0787 0.038 Uiso 1 1 calc R
H10C H -0.3095 0.6438 1.0042 0.038 Uiso 1 1 calc R
C11 C 0.2745(3) 0.6652(2) 0.64399(17) 0.0200(4) Uani 1 1 d .
C12 C 0.1896(3) 0.6624(3) 0.54469(17) 0.0247(4) Uani 1 1 d .
H12A H 0.1014 0.7612 0.5021 0.030 Uiso 1 1 calc R
C13 C 0.2363(3) 0.5124(3) 0.50907(18) 0.0279(5) Uani 1 1 d .
H13A H 0.1785 0.5096 0.4416 0.034 Uiso 1 1 calc R
C14 C 0.3656(3) 0.3660(3) 0.56948(19) 0.0265(4) Uani 1 1 d .
C15 C 0.4491(3) 0.3727(3) 0.6684(2) 0.0275(4) Uani 1 1 d .
H15A H 0.5386 0.2743 0.7102 0.033 Uiso 1 1 calc R
C16 C 0.4038(3) 0.5203(3) 0.70671(18) 0.0236(4) Uani 1 1 d .
H16A H 0.4602 0.5229 0.7750 0.028 Uiso 1 1 calc R
C17 C 0.4118(4) 0.2045(3) 0.5302(2) 0.0399(6) Uani 1 1 d .
H17A H 0.3905 0.2261 0.4443 0.060 Uiso 1 1 calc R
H17B H 0.3398 0.1493 0.5715 0.060 Uiso 1 1 calc R
H17C H 0.5354 0.1329 0.5493 0.060 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
O2 S1 O1 119.86(9)
O2 S1 N1 106.13(9)
O1 S1 N1 106.61(9)
O2 S1 C11 108.81(10)
O1 S1 C11 108.49(9)
N1 S1 C11 106.10(9)
C5 N1 C1 115.76(15)
C5 N1 S1 116.56(13)
C1 N1 S1 115.11(13)
N1 C1 C2 112.84(15)
N1 C1 H1A 109.0
C2 C1 H1A 109.0
N1 C1 H1B 109.0
C2 C1 H1B 109.0
H1A C1 H1B 107.8
C9 C2 C6 121.39(17)
C9 C2 C1 119.55(16)
C6 C2 C1 110.44(16)
C9 C2 C3 60.48(13)
C6 C2 C3 120.76(16)
C1 C2 C3 116.21(16)
C4 C3 C10 115.60(17)
C4 C3 C2 115.25(16)
C10 C3 C2 120.77(17)
C4 C3 C9 115.51(17)
C10 C3 C9 118.88(17)
C2 C3 C9 59.09(12)
C5 C4 C3 123.28(18)
C5 C4 H4A 118.4
C3 C4 H4A 118.4
C4 C5 N1 120.77(18)
C4 C5 H5A 119.6
N1 C5 H5A 119.6
C7 C6 C8 59.78(15)
C7 C6 C2 124.49(19)
C8 C6 C2 121.15(18)
C7 C6 H6A 113.7
C8 C6 H6A 113.7
C2 C6 H6A 113.7
C8 C7 C6 60.20(15)
C8 C7 H7A 117.8
C6 C7 H7A 117.8
C8 C7 H7B 117.8
C6 C7 H7B 117.8
H7A C7 H7B 114.9
C7 C8 C6 60.02(14)
C7 C8 H8A 117.8
C6 C8 H8A 117.8
C7 C8 H8B 117.8
C6 C8 H8B 117.8
H8A C8 H8B 114.9
C2 C9 C3 60.43(12)
C2 C9 H9A 117.7
C3 C9 H9A 117.7
C2 C9 H9B 117.7
C3 C9 H9B 117.7
H9A C9 H9B 114.8
C3 C10 H10A 109.5
C3 C10 H10B 109.5
H10A C10 H10B 109.5
C3 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C12 C11 C16 120.78(18)
C12 C11 S1 119.61(16)
C16 C11 S1 119.53(15)
C13 C12 C11 118.66(19)
C13 C12 H12A 120.7
C11 C12 H12A 120.7
C12 C13 C14 121.8(2)
C12 C13 H13A 119.1
C14 C13 H13A 119.1
C13 C14 C15 118.25(19)
C13 C14 C17 120.8(2)
C15 C14 C17 121.0(2)
C16 C15 C14 121.2(2)
C16 C15 H15A 119.4
C14 C15 H15A 119.4
C15 C16 C11 119.31(19)
C15 C16 H16A 120.3
C11 C16 H16A 120.3
C14 C17 H17A 109.5
C14 C17 H17B 109.5
H17A C17 H17B 109.5
C14 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4319(16)
S1 O1 1.4347(16)
S1 N1 1.6555(17)
S1 C11 1.760(2)
N1 C5 1.425(2)
N1 C1 1.481(2)
C1 C2 1.517(3)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C9 1.501(3)
C2 C6 1.504(3)
C2 C3 1.522(3)
C3 C4 1.485(3)
C3 C10 1.515(3)
C3 C9 1.523(3)
C4 C5 1.330(3)
C4 H4A 0.9500
C5 H5A 0.9500
C6 C7 1.498(3)
C6 C8 1.501(3)
C6 H6A 1.0000
C7 C8 1.494(3)
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9A 0.9900
C9 H9B 0.9900
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 C12 1.391(3)
C11 C16 1.394(3)
C12 C13 1.387(3)
C12 H12A 0.9500
C13 C14 1.392(3)
C13 H13A 0.9500
C14 C15 1.395(3)
C14 C17 1.504(3)
C15 C16 1.384(3)
C15 H15A 0.9500
C16 H16A 0.9500
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
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
O2 S1 N1 C5 173.58(14)
O1 S1 N1 C5 44.74(16)
C11 S1 N1 C5 -70.77(16)
O2 S1 N1 C1 -45.99(15)
O1 S1 N1 C1 -174.83(13)
C11 S1 N1 C1 69.67(15)
C5 N1 C1 C2 -46.7(2)
S1 N1 C1 C2 172.51(12)
N1 C1 C2 C9 -35.7(2)
N1 C1 C2 C6 176.03(15)
N1 C1 C2 C3 33.7(2)
C9 C2 C3 C4 105.82(19)
C6 C2 C3 C4 -143.10(18)
C1 C2 C3 C4 -4.9(2)
C9 C2 C3 C10 -107.4(2)
C6 C2 C3 C10 3.7(3)
C1 C2 C3 C10 141.95(18)
C6 C2 C3 C9 111.1(2)
C1 C2 C3 C9 -110.67(19)
C10 C3 C4 C5 -162.99(19)
C2 C3 C4 C5 -14.4(3)
C9 C3 C4 C5 51.7(3)
C3 C4 C5 N1 2.1(3)
C1 N1 C5 C4 29.8(3)
S1 N1 C5 C4 169.98(16)
C9 C2 C6 C7 -0.8(3)
C1 C2 C6 C7 146.8(2)
C3 C2 C6 C7 -72.8(3)
C9 C2 C6 C8 -73.4(3)
C1 C2 C6 C8 74.1(2)
C3 C2 C6 C8 -145.5(2)
C2 C6 C7 C8 -109.0(2)
C2 C6 C8 C7 114.4(2)
C6 C2 C9 C3 -110.1(2)
C1 C2 C9 C3 105.22(19)
C4 C3 C9 C2 -105.38(19)
C10 C3 C9 C2 110.5(2)
O2 S1 C11 C12 -158.19(15)
O1 S1 C11 C12 -26.23(18)
N1 S1 C11 C12 87.99(17)
O2 S1 C11 C16 24.92(18)
O1 S1 C11 C16 156.87(15)
N1 S1 C11 C16 -88.90(17)
C16 C11 C12 C13 -0.1(3)
S1 C11 C12 C13 -176.97(16)
C11 C12 C13 C14 -0.3(3)
C12 C13 C14 C15 0.0(3)
C12 C13 C14 C17 179.0(2)
C13 C14 C15 C16 0.7(3)
C17 C14 C15 C16 -178.3(2)
C14 C15 C16 C11 -1.1(3)
C12 C11 C16 C15 0.8(3)
S1 C11 C16 C15 177.67(15)
