#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/47/4024759.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_4024759
loop_
_publ_author_name
'Prasath Kothandaraman'
'Shi Jia Foo'
'Philip Wai Hong Chan'
_publ_section_title
;
Gold-Catalyzed Intramolecular Allylic Amination of
2-Tosylaminophenylprop-1-en-3-ols. A Concise Synthesis of (\+-)-Angustureine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5947
_journal_page_last               5952
_journal_paper_doi               10.1021/jo900917q
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C23 H21 N O2 S'
_chemical_formula_sum            'C23 H21 N O2 S'
_chemical_formula_weight         375.47
_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                 98.572(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1459(5)
_cell_length_b                   8.8607(4)
_cell_length_c                   19.6255(8)
_cell_measurement_reflns_used    4924
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.33
_cell_measurement_theta_min      2.53
_cell_volume                     1916.57(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21704
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.9566
_exptl_absorpt_correction_T_min  0.9291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0811
_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)+(0.1212P)²+0.7098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1617
_refine_ls_wR_factor_ref         0.2094
_reflns_number_gt                2395
_reflns_number_total             3373
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900917q_si_004.cif
_cod_data_source_block           chan47
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4024759
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 0.7365(3) 0.7342(3) 0.17123(14) 0.0411(7) Uani 1 1 d . . .
C2 C 0.7499(3) 0.8853(3) 0.15616(17) 0.0506(8) Uani 1 1 d . . .
H2 H 0.8241 0.9328 0.1693 0.061 Uiso 1 1 calc R . .
C3 C 0.6540(3) 0.9655(4) 0.12184(17) 0.0558(9) Uani 1 1 d . . .
H3 H 0.6636 1.0668 0.1116 0.067 Uiso 1 1 calc R . .
C4 C 0.5431(3) 0.8958(4) 0.10254(18) 0.0561(9) Uani 1 1 d . . .
H4 H 0.4783 0.9497 0.0789 0.067 Uiso 1 1 calc R . .
C5 C 0.5290(3) 0.7458(4) 0.11858(17) 0.0491(8) Uani 1 1 d . . .
H5 H 0.4541 0.6996 0.1058 0.059 Uiso 1 1 calc R . .
C6 C 0.6248(2) 0.6622(3) 0.15355(14) 0.0414(7) Uani 1 1 d . . .
C7 C 0.6105(2) 0.5031(3) 0.17406(14) 0.0395(7) Uani 1 1 d . . .
C8 C 0.4957(2) 0.4247(3) 0.14445(15) 0.0394(7) Uani 1 1 d . . .
C9 C 0.3991(3) 0.4225(3) 0.18143(16) 0.0477(7) Uani 1 1 d . . .
H9 H 0.4078 0.4667 0.2249 0.057 Uiso 1 1 calc R . .
C10 C 0.2899(3) 0.3556(4) 0.15496(18) 0.0542(8) Uani 1 1 d . . .
H10 H 0.2253 0.3578 0.1799 0.065 Uiso 1 1 calc R . .
C11 C 0.2773(3) 0.2860(4) 0.09175(18) 0.0569(9) Uani 1 1 d . . .
H11 H 0.2046 0.2392 0.0742 0.068 Uiso 1 1 calc R . .
C12 C 0.3719(3) 0.2858(4) 0.05480(18) 0.0605(9) Uani 1 1 d . . .
H12 H 0.3633 0.2389 0.0120 0.073 Uiso 1 1 calc R . .
C13 C 0.4811(3) 0.3555(4) 0.08086(16) 0.0529(8) Uani 1 1 d . . .
H13 H 0.5448 0.3553 0.0551 0.063 Uiso 1 1 calc R . .
C14 C 0.6934(3) 0.4399(3) 0.22139(15) 0.0433(7) Uani 1 1 d . . .
C15 C 0.6838(3) 0.2857(4) 0.25070(19) 0.0586(9) Uani 1 1 d . . .
H15A H 0.6128 0.2364 0.2273 0.088 Uiso 1 1 calc R . .
H15B H 0.6781 0.2935 0.2989 0.088 Uiso 1 1 calc R . .
H15C H 0.7545 0.2282 0.2448 0.088 Uiso 1 1 calc R . .
C16 C 0.8009(3) 0.5308(3) 0.25362(16) 0.0482(7) Uani 1 1 d . . .
H16A H 0.7824 0.5757 0.2959 0.058 Uiso 1 1 calc R . .
H16B H 0.8694 0.4634 0.2657 0.058 Uiso 1 1 calc R . .
C17 C 0.9236(2) 0.4667(3) 0.11504(15) 0.0445(7) Uani 1 1 d . . .
C18 C 0.9521(3) 0.3204(4) 0.13692(17) 0.0513(8) Uani 1 1 d . . .
H18 H 0.9905 0.3019 0.1815 0.062 Uiso 1 1 calc R . .
C19 C 0.9226(3) 0.2025(4) 0.09140(19) 0.0573(9) Uani 1 1 d . . .
H19 H 0.9427 0.1045 0.1057 0.069 Uiso 1 1 calc R . .
C20 C 0.8638(3) 0.2266(4) 0.02494(19) 0.0612(9) Uani 1 1 d . . .
C21 C 0.8312(4) 0.0975(5) -0.0242(2) 0.0897(14) Uani 1 1 d . . .
H21A H 0.8346 0.0045 0.0011 0.134 Uiso 1 1 calc R . .
H21B H 0.8876 0.0936 -0.0567 0.134 Uiso 1 1 calc R . .
H21C H 0.7506 0.1121 -0.0484 0.134 Uiso 1 1 calc R . .
C22 C 0.8365(4) 0.3745(5) 0.00413(18) 0.0690(11) Uani 1 1 d . . .
H22 H 0.7977 0.3933 -0.0404 0.083 Uiso 1 1 calc R . .
C23 C 0.8666(3) 0.4931(4) 0.04886(18) 0.0618(9) Uani 1 1 d . . .
H23 H 0.8482 0.5914 0.0343 0.074 Uiso 1 1 calc R . .
N1 N 0.8360(2) 0.6513(3) 0.20881(13) 0.0454(6) Uani 1 1 d . . .
O1 O 0.9782(2) 0.7491(3) 0.13397(14) 0.0678(7) Uani 1 1 d . . .
O2 O 1.04845(19) 0.5673(3) 0.22676(13) 0.0667(7) Uani 1 1 d . . .
S1 S 0.95796(6) 0.61755(9) 0.17252(4) 0.0499(3) 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'
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'
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 C6 120.6(3) . . ?
C2 C1 N1 120.3(3) . . ?
C6 C1 N1 119.0(3) . . ?
C3 C2 C1 120.3(3) . . ?
C2 C3 C4 120.1(3) . . ?
C5 C4 C3 119.7(3) . . ?
C4 C5 C6 121.3(3) . . ?
C5 C6 C1 118.0(3) . . ?
C5 C6 C7 122.3(3) . . ?
C1 C6 C7 119.7(3) . . ?
C14 C7 C6 119.9(3) . . ?
C14 C7 C8 122.7(3) . . ?
C6 C7 C8 117.2(2) . . ?
C13 C8 C9 118.1(3) . . ?
C13 C8 C7 122.5(3) . . ?
C9 C8 C7 119.3(3) . . ?
C10 C9 C8 121.2(3) . . ?
C11 C10 C9 119.8(3) . . ?
C12 C11 C10 119.8(3) . . ?
C11 C12 C13 120.4(3) . . ?
C8 C13 C12 120.6(3) . . ?
C7 C14 C15 124.9(3) . . ?
C7 C14 C16 119.7(3) . . ?
C15 C14 C16 115.2(3) . . ?
N1 C16 C14 113.8(2) . . ?
C23 C17 C18 120.2(3) . . ?
C23 C17 S1 120.1(3) . . ?
C18 C17 S1 119.7(2) . . ?
C19 C18 C17 119.0(3) . . ?
C18 C19 C20 121.7(3) . . ?
C19 C20 C22 118.2(3) . . ?
C19 C20 C21 121.4(4) . . ?
C22 C20 C21 120.4(4) . . ?
C23 C22 C20 120.6(3) . . ?
C17 C23 C22 120.3(3) . . ?
C1 N1 C16 115.0(2) . . ?
C1 N1 S1 119.46(19) . . ?
C16 N1 S1 115.8(2) . . ?
O2 S1 O1 120.13(16) . . ?
O2 S1 N1 105.70(14) . . ?
O1 S1 N1 106.61(14) . . ?
O2 S1 C17 107.74(15) . . ?
O1 S1 C17 108.57(15) . . ?
N1 S1 C17 107.48(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
C1 C2 1.384(4) . ?
C1 C6 1.396(4) . ?
C1 N1 1.439(4) . ?
C2 C3 1.373(4) . ?
C3 C4 1.383(5) . ?
C4 C5 1.380(4) . ?
C5 C6 1.393(4) . ?
C6 C7 1.482(4) . ?
C7 C14 1.331(4) . ?
C7 C8 1.495(4) . ?
C8 C13 1.378(4) . ?
C8 C9 1.386(4) . ?
C9 C10 1.383(4) . ?
C10 C11 1.374(5) . ?
C11 C12 1.366(5) . ?
C12 C13 1.393(5) . ?
C14 C15 1.492(4) . ?
C14 C16 1.503(4) . ?
C16 N1 1.473(4) . ?
C17 C23 1.378(4) . ?
C17 C18 1.388(4) . ?
C17 S1 1.754(3) . ?
C18 C19 1.382(5) . ?
C19 C20 1.386(5) . ?
C20 C22 1.393(5) . ?
C20 C21 1.505(5) . ?
C22 C23 1.379(5) . ?
N1 S1 1.653(2) . ?
O1 S1 1.426(2) . ?
O2 S1 1.424(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659019
