#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:38:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178435 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/56/4025639.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_4025639
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 Br1 N1 O3 S1'
_chemical_formula_sum            'C20 H20 Br N O3 S'
_chemical_formula_weight         434.34
_chemical_name_systematic
;
?
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.7069(8)
_cell_length_b                   11.1373(3)
_cell_length_c                   6.0181(2)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1924.09(10)
_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      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            13869
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    2.264
_exptl_absorpt_correction_T_max  0.6602
_exptl_absorpt_correction_T_min  0.3001
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3367
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0316
_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)+(0.0306P)²+0.0374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0687
_reflns_number_gt                2896
_reflns_number_total             3367
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101148e_si_003_3.cif
_cod_data_source_block           a9856
_cod_database_code               4025639
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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
Br1 Br 0.498275(10) -0.27921(3) 0.72670(11) 0.06048(14) Uani 1 1 d . . .
C1 C 0.18984(10) 0.2902(2) 1.0107(5) 0.0302(7) Uani 1 1 d . . .
C2 C 0.17474(11) 0.1981(3) 1.1479(5) 0.0372(8) Uani 1 1 d . . .
H2 H 0.1880 0.1878 1.2911 0.045 Uiso 1 1 calc R . .
C3 C 0.14027(11) 0.1216(3) 1.0748(6) 0.0457(8) Uani 1 1 d . . .
H3 H 0.1300 0.0584 1.1688 0.055 Uiso 1 1 calc R . .
C4 C 0.12022(12) 0.1353(3) 0.8656(6) 0.0440(8) Uani 1 1 d . . .
C5 C 0.08097(12) 0.0562(3) 0.7906(7) 0.0638(12) Uani 1 1 d . . .
H5A H 0.0746 -0.0042 0.9049 0.096 Uiso 1 1 calc R . .
H5B H 0.0897 0.0160 0.6517 0.096 Uiso 1 1 calc R . .
H5C H 0.0531 0.1051 0.7661 0.096 Uiso 1 1 calc R . .
C6 C 0.13632(10) 0.2272(3) 0.7310(7) 0.0422(7) Uani 1 1 d . . .
H6 H 0.1231 0.2374 0.5875 0.051 Uiso 1 1 calc R . .
C7 C 0.17119(10) 0.3046(3) 0.8004(5) 0.0394(8) Uani 1 1 d . . .
H7 H 0.1821 0.3665 0.7052 0.047 Uiso 1 1 calc R . .
C8 C 0.29512(9) 0.3066(3) 0.8088(4) 0.0311(7) Uani 1 1 d . . .
H8A H 0.2988 0.3825 0.7251 0.037 Uiso 1 1 calc R . .
H8B H 0.2713 0.2561 0.7350 0.037 Uiso 1 1 calc R . .
C9 C 0.34146(9) 0.2400(3) 0.8311(5) 0.0274(6) Uani 1 1 d . . .
H9 H 0.3478 0.1922 0.6937 0.033 Uiso 1 1 calc R . .
C10 C 0.38095(10) 0.3230(3) 0.8767(5) 0.0316(7) Uani 1 1 d . . .
H10 H 0.3779 0.3765 0.9987 0.038 Uiso 1 1 calc R . .
C11 C 0.41945(9) 0.3277(3) 0.7620(6) 0.0426(8) Uani 1 1 d . . .
H11A H 0.4238 0.2756 0.6388 0.051 Uiso 1 1 calc R . .
H11B H 0.4431 0.3834 0.8016 0.051 Uiso 1 1 calc R . .
C12 C 0.33126(9) 0.1548(2) 1.0295(5) 0.0262(6) Uani 1 1 d . . .
H12 H 0.3132 0.0844 0.9730 0.031 Uiso 1 1 calc R . .
C13 C 0.29975(10) 0.2277(3) 1.1835(5) 0.0398(8) Uani 1 1 d . . .
H13A H 0.2732 0.1784 1.2362 0.048 Uiso 1 1 calc R . .
H13B H 0.3174 0.2573 1.3138 0.048 Uiso 1 1 calc R . .
C14 C 0.37424(9) 0.1086(3) 1.1471(5) 0.0264(7) Uani 1 1 d . . .
C15 C 0.40442(9) 0.0179(2) 1.0330(4) 0.0234(6) Uani 1 1 d . . .
C16 C 0.39478(9) -0.0285(2) 0.8250(4) 0.0270(6) Uani 1 1 d . . .
H16 H 0.3685 0.0004 0.7452 0.032 Uiso 1 1 calc R . .
C17 C 0.42258(8) -0.1159(2) 0.7310(5) 0.0309(6) Uani 1 1 d . . .
H17 H 0.4158 -0.1469 0.5875 0.037 Uiso 1 1 calc R . .
C18 C 0.46058(9) -0.1573(3) 0.8505(5) 0.0323(7) Uani 1 1 d . . .
C19 C 0.47162(10) -0.1112(3) 1.0567(5) 0.0353(7) Uani 1 1 d . . .
H19 H 0.4982 -0.1393 1.1352 0.042 Uiso 1 1 calc R . .
C20 C 0.44335(9) -0.0237(2) 1.1467(5) 0.0303(7) Uani 1 1 d . . .
H20 H 0.4506 0.0087 1.2885 0.036 Uiso 1 1 calc R . .
N1 N 0.28310(7) 0.3293(2) 1.0448(4) 0.0300(6) Uani 1 1 d . . .
O1 O 0.22961(8) 0.49742(19) 0.9754(4) 0.0464(6) Uani 1 1 d . . .
O2 O 0.23127(8) 0.39719(19) 1.3415(3) 0.0428(6) Uani 1 1 d . . .
O3 O 0.38446(7) 0.1427(2) 1.3318(4) 0.0433(6) Uani 1 1 d . . .
S1 S 0.23354(3) 0.39016(7) 1.10347(12) 0.03394(19) 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'
Br Br -0.2901 2.4595 '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 120.6(3) . . ?
C2 C1 S1 120.0(2) . . ?
C7 C1 S1 119.4(2) . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C6 C4 C3 118.2(3) . . ?
C6 C4 C5 120.6(3) . . ?
C3 C4 C5 121.2(3) . . ?
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 . . ?
C4 C6 C7 121.7(3) . . ?
C4 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C1 C7 C6 118.9(3) . . ?
C1 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
N1 C8 C9 101.6(2) . . ?
N1 C8 H8A 111.4 . . ?
C9 C8 H8A 111.4 . . ?
N1 C8 H8B 111.4 . . ?
C9 C8 H8B 111.4 . . ?
H8A C8 H8B 109.3 . . ?
C10 C9 C8 112.2(2) . . ?
C10 C9 C12 112.4(2) . . ?
C8 C9 C12 101.5(2) . . ?
C10 C9 H9 110.1 . . ?
C8 C9 H9 110.1 . . ?
C12 C9 H9 110.1 . . ?
C11 C10 C9 125.0(3) . . ?
C11 C10 H10 117.5 . . ?
C9 C10 H10 117.5 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C14 C12 C13 112.3(2) . . ?
C14 C12 C9 114.4(2) . . ?
C13 C12 C9 104.7(2) . . ?
C14 C12 H12 108.4 . . ?
C13 C12 H12 108.4 . . ?
C9 C12 H12 108.4 . . ?
N1 C13 C12 104.7(2) . . ?
N1 C13 H13A 110.8 . . ?
C12 C13 H13A 110.8 . . ?
N1 C13 H13B 110.8 . . ?
C12 C13 H13B 110.8 . . ?
H13A C13 H13B 108.9 . . ?
O3 C14 C15 119.5(3) . . ?
O3 C14 C12 121.4(3) . . ?
C15 C14 C12 119.1(2) . . ?
C20 C15 C16 118.8(2) . . ?
C20 C15 C14 117.7(2) . . ?
C16 C15 C14 123.5(2) . . ?
C17 C16 C15 121.3(3) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C18 C17 C16 118.5(3) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C17 C18 C19 121.6(3) . . ?
C17 C18 Br1 119.1(2) . . ?
C19 C18 Br1 119.4(2) . . ?
C20 C19 C18 118.7(3) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C19 C20 C15 121.0(3) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
C13 N1 C8 109.4(2) . . ?
C13 N1 S1 118.70(18) . . ?
C8 N1 S1 119.08(18) . . ?
O1 S1 O2 119.32(14) . . ?
O1 S1 N1 107.64(12) . . ?
O2 S1 N1 106.33(14) . . ?
O1 S1 C1 107.50(15) . . ?
O2 S1 C1 108.48(15) . . ?
N1 S1 C1 106.98(13) . . ?
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
Br1 C18 1.889(3) . ?
C1 C2 1.386(4) . ?
C1 C7 1.384(4) . ?
C1 S1 1.768(3) . ?
C2 C3 1.378(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(5) . ?
C3 H3 0.9500 . ?
C4 C6 1.384(5) . ?
C4 C5 1.500(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.386(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N1 1.484(3) . ?
C8 C9 1.529(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.488(4) . ?
C9 C12 1.553(4) . ?
C9 H9 1.0000 . ?
C10 C11 1.304(4) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9500 . ?
C11 H11B 0.9500 . ?
C12 C14 1.512(4) . ?
C12 C13 1.528(4) . ?
C12 H12 1.0000 . ?
C13 N1 1.486(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O3 1.210(3) . ?
C14 C15 1.498(4) . ?
C15 C20 1.390(4) . ?
C15 C16 1.382(4) . ?
C16 C17 1.380(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(4) . ?
C19 C20 1.380(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
N1 S1 1.615(2) . ?
O1 S1 1.426(2) . ?
O2 S1 1.436(2) . ?
