#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:38:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178435 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/56/4025640.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_4025640
loop_
_publ_author_name
'Ming-Chang P. Yeh'
'Ming-Nan Lin'
'Wei-Jong Chang'
'Jia-Lun Liou'
'Ya-Fon Shih'
_publ_section_title
;
 Synthesis of cis-3-Acyl-4-alkenylpyrrolidines via Gold(I)-Catalyzed
 Cycloisomerization Reaction of
 (Z)-8-Aryl-5-tosyl-5-azaoct-2-en-7-yn-1-ols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6031
_journal_page_last               6034
_journal_paper_doi               10.1021/jo101148e
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C20 H20 N2 O5 S1'
_chemical_formula_sum            'C20 H20 N2 O5 S'
_chemical_formula_weight         400.44
_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                 99.333(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7243(7)
_cell_length_b                   6.0218(3)
_cell_length_c                   26.3225(17)
_cell_measurement_reflns_used    9197
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_volume                     1990.2(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Denzo and Scalepack'
_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-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.910
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0783
_diffrn_reflns_av_sigmaI/netI    0.1233
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6128
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.0664
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
?
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.2030
_refine_ls_R_factor_gt           0.0881
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2578
_refine_ls_wR_factor_ref         0.3541
_reflns_number_gt                1412
_reflns_number_total             3214
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101148e_si_003_4.cif
_cod_data_source_block           10161
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4025640
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
C1 C 0.1906(6) -0.0041(11) 0.2783(3) 0.0564(19) Uani 1 1 d . . .
C2 C 0.1679(7) 0.1650(13) 0.3101(3) 0.076(2) Uani 1 1 d . . .
H2 H 0.2098 0.2923 0.3136 0.091 Uiso 1 1 calc R . .
C3 C 0.0841(8) 0.1475(15) 0.3366(3) 0.086(3) Uani 1 1 d . . .
H3 H 0.0706 0.2628 0.3582 0.103 Uiso 1 1 calc R . .
C4 C 0.0196(7) -0.0360(18) 0.3321(4) 0.085(3) Uani 1 1 d . . .
C5 C -0.0730(9) -0.052(2) 0.3614(4) 0.126(4) Uani 1 1 d . . .
H5A H -0.0781 0.0822 0.3804 0.189 Uiso 1 1 calc R . .
H5B H -0.0621 -0.1756 0.3848 0.189 Uiso 1 1 calc R . .
H5C H -0.1378 -0.0742 0.3375 0.189 Uiso 1 1 calc R . .
C6 C 0.0441(7) -0.2070(16) 0.3016(4) 0.082(3) Uani 1 1 d . . .
H6 H 0.0033 -0.3358 0.2993 0.098 Uiso 1 1 calc R . .
C7 C 0.1264(7) -0.1932(12) 0.2746(3) 0.072(2) Uani 1 1 d . . .
H7 H 0.1401 -0.3104 0.2536 0.086 Uiso 1 1 calc R . .
C8 C 0.4639(6) 0.0705(12) 0.3232(3) 0.070(2) Uani 1 1 d . . .
H8A H 0.4177 0.1345 0.3452 0.084 Uiso 1 1 calc R . .
H8B H 0.5004 0.1891 0.3082 0.084 Uiso 1 1 calc R . .
C9 C 0.5419(6) -0.0897(11) 0.3525(3) 0.0608(19) Uani 1 1 d . . .
H9 H 0.5968 -0.1234 0.3315 0.073 Uiso 1 1 calc R . .
C10 C 0.4723(6) -0.3001(12) 0.3546(3) 0.066(2) Uani 1 1 d . . .
H10 H 0.5177 -0.4319 0.3610 0.079 Uiso 1 1 calc R . .
C11 C 0.4006(8) -0.2817(14) 0.3947(4) 0.088(3) Uani 1 1 d . . .
H11 H 0.3476 -0.1740 0.3893 0.106 Uiso 1 1 calc R . .
C12 C 0.4053(12) -0.3958(19) 0.4342(6) 0.163(6) Uani 1 1 d . . .
H12A H 0.4570 -0.5057 0.4413 0.195 Uiso 1 1 calc R . .
H12B H 0.3572 -0.3716 0.4567 0.195 Uiso 1 1 calc R . .
C13 C 0.4111(6) -0.3052(11) 0.2999(3) 0.072(2) Uani 1 1 d . . .
H13A H 0.4488 -0.3930 0.2777 0.087 Uiso 1 1 calc R . .
H13B H 0.3408 -0.3683 0.2993 0.087 Uiso 1 1 calc R . .
C14 C 0.5951(6) -0.0139(13) 0.4033(3) 0.070(2) Uani 1 1 d . . .
C15 C 0.6775(6) -0.1568(12) 0.4354(3) 0.072(2) Uani 1 1 d . . .
C16 C 0.7082(9) -0.1120(15) 0.4858(4) 0.105(3) Uani 1 1 d . . .
H16 H 0.6822 0.0145 0.4998 0.126 Uiso 1 1 calc R . .
C17 C 0.7774(10) -0.2499(18) 0.5172(5) 0.123(4) Uani 1 1 d . . .
H17 H 0.7956 -0.2244 0.5524 0.148 Uiso 1 1 calc R . .
C18 C 0.8187(8) -0.4302(16) 0.4932(5) 0.095(3) Uani 1 1 d . A .
C19 C 0.7935(7) -0.4739(15) 0.4457(4) 0.088(3) Uani 1 1 d . . .
H19 H 0.8233 -0.5965 0.4319 0.106 Uiso 1 1 calc R . .
C20 C 0.7202(6) -0.3380(14) 0.4132(4) 0.080(2) Uani 1 1 d . . .
H20 H 0.7014 -0.3690 0.3783 0.096 Uiso 1 1 calc R . .
N1 N 0.4034(5) -0.0714(9) 0.2830(2) 0.0646(18) Uani 1 1 d . . .
N2 N 0.8956(9) -0.5784(19) 0.5302(5) 0.116(3) Uani 1 1 d . . .
O1 O 0.3171(4) 0.2466(9) 0.2367(2) 0.0849(18) Uani 1 1 d . . .
O2 O 0.2812(5) -0.1349(9) 0.2034(2) 0.0898(18) Uani 1 1 d . . .
O3 O 0.5740(6) 0.1689(10) 0.4203(2) 0.108(2) Uani 1 1 d . . .
O4 O 0.942(2) -0.493(5) 0.5677(17) 0.152(11) Uani 0.50 1 d P A 1
O4' O 0.890(3) -0.574(5) 0.5750(14) 0.152(12) Uani 0.50 1 d P A 2
O5 O 0.9307(7) -0.7311(13) 0.5083(4) 0.157(4) Uani 1 1 d . A .
S1 S 0.29930(16) 0.0159(3) 0.24566(8) 0.0697(8) 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 0.0000 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
C2 C1 C7 117.9(8) . . ?
C2 C1 S1 120.6(6) . . ?
C7 C1 S1 121.5(6) . . ?
C3 C2 C1 120.6(8) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.5(9) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C6 C4 C3 117.8(8) . . ?
C6 C4 C5 121.2(10) . . ?
C3 C4 C5 120.9(10) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 121.8(8) . . ?
C7 C6 H6 119.1 . . ?
C4 C6 H6 119.1 . . ?
C6 C7 C1 120.3(8) . . ?
C6 C7 H7 119.8 . . ?
C1 C7 H7 119.8 . . ?
N1 C8 C9 102.8(6) . . ?
N1 C8 H8A 111.2 . . ?
C9 C8 H8A 111.2 . . ?
N1 C8 H8B 111.2 . . ?
C9 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
C14 C9 C8 115.8(6) . . ?
C14 C9 C10 113.8(6) . . ?
C8 C9 C10 102.0(6) . . ?
C14 C9 H9 108.3 . . ?
C8 C9 H9 108.3 . . ?
C10 C9 H9 108.3 . . ?
C11 C10 C13 112.9(7) . . ?
C11 C10 C9 112.2(6) . . ?
C13 C10 C9 101.0(6) . . ?
C11 C10 H10 110.1 . . ?
C13 C10 H10 110.1 . . ?
C9 C10 H10 110.1 . . ?
C12 C11 C10 126.5(10) . . ?
C12 C11 H11 116.8 . . ?
C10 C11 H11 116.8 . . ?
C11 C12 H12A 120.0 . . ?
C11 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
N1 C13 C10 105.4(6) . . ?
N1 C13 H13A 110.7 . . ?
C10 C13 H13A 110.7 . . ?
N1 C13 H13B 110.7 . . ?
C10 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
O3 C14 C9 120.8(7) . . ?
O3 C14 C15 118.6(7) . . ?
C9 C14 C15 120.6(7) . . ?
C16 C15 C20 120.0(8) . . ?
C16 C15 C14 120.2(8) . . ?
C20 C15 C14 119.8(8) . . ?
C15 C16 C17 121.5(10) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C16 C17 C18 116.5(10) . . ?
C16 C17 H17 121.8 . . ?
C18 C17 H17 121.8 . . ?
C19 C18 C17 123.5(10) . . ?
C19 C18 N2 122.3(11) . . ?
C17 C18 N2 114.1(11) . . ?
C18 C19 C20 120.7(9) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 117.6(8) . . ?
C15 C20 H20 121.2 . . ?
C19 C20 H20 121.2 . . ?
C13 N1 C8 109.5(5) . . ?
C13 N1 S1 120.4(5) . . ?
C8 N1 S1 122.2(5) . . ?
O5 N2 O4 124(2) . . ?
O5 N2 O4' 124.9(18) . . ?
O4 N2 O4' 43.0(17) . . ?
O5 N2 C18 112.6(11) . . ?
O4 N2 C18 117(2) . . ?
O4' N2 C18 118.6(17) . . ?
O2 S1 O1 119.9(4) . . ?
O2 S1 N1 106.4(3) . . ?
O1 S1 N1 106.3(3) . . ?
O2 S1 C1 107.4(3) . . ?
O1 S1 C1 107.9(4) . . ?
N1 S1 C1 108.5(3) . . ?
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
C1 C2 1.378(10) . ?
C1 C7 1.395(10) . ?
C1 S1 1.748(8) . ?
C2 C3 1.370(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(12) . ?
C3 H3 0.9300 . ?
C4 C6 1.372(12) . ?
C4 C5 1.513(13) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.360(12) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.477(8) . ?
C8 C9 1.504(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.469(10) . ?
C9 C10 1.552(9) . ?
C9 H9 0.9800 . ?
C10 C11 1.507(11) . ?
C10 C13 1.521(11) . ?
C10 H10 0.9800 . ?
C11 C12 1.239(13) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9300 . ?
C12 H12B 0.9300 . ?
C13 N1 1.476(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O3 1.234(8) . ?
C14 C15 1.506(11) . ?
C15 C16 1.347(11) . ?
C15 C20 1.390(10) . ?
C16 C17 1.383(13) . ?
C16 H16 0.9300 . ?
C17 C18 1.400(14) . ?
C17 H17 0.9300 . ?
C18 C19 1.268(12) . ?
C18 N2 1.547(13) . ?
C19 C20 1.417(12) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
N1 S1 1.604(6) . ?
N2 O5 1.209(12) . ?
N2 O4 1.18(4) . ?
N2 O4' 1.19(4) . ?
O1 S1 1.433(5) . ?
O2 S1 1.424(6) . ?
