#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:14:47 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180295 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/09/7150959.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_7150959
loop_
_publ_author_name
'Chau, Chi-Min'
'Liu, Kuan-Miao'
_publ_section_title
;
 Diels--Alder reactions of three fused nitrogen-containing bicyclic
 enones: an efficient method toward novel nitrogen-containing angular
 tricyclic skeletons
;
_journal_issue                   17
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              3127
_journal_page_last               3134
_journal_paper_doi               10.1039/b806773m
_journal_volume                  6
_journal_year                    2008
_chemical_formula_sum            'C20 H23 N O3 S'
_chemical_formula_weight         357.45
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.7670(10)
_cell_angle_beta                 103.3140(10)
_cell_angle_gamma                98.3220(10)
_cell_formula_units_Z            2
_cell_length_a                   7.8582(5)
_cell_length_b                   10.1699(7)
_cell_length_c                   11.6933(8)
_cell_measurement_reflns_used    3257
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     872.06(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      295(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_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  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9136
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.96682
_exptl_absorpt_correction_T_min  0.88863
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       Tabular
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4095
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0479
_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)+(0.0749P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                2893
_reflns_number_total             4095
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b806773m.txt
_cod_data_source_block           ap16m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               7150959
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.37674(6) 0.35262(5) 0.76563(5) 0.03622(16) Uani 1 1 d . . .
N1 N 0.43065(19) 0.22367(16) 0.81712(13) 0.0332(4) Uani 1 1 d . . .
O1 O 0.7095(2) 0.11564(18) 1.04386(13) 0.0583(4) Uani 1 1 d . . .
O2 O 0.32648(19) 0.43827(16) 0.86025(14) 0.0498(4) Uani 1 1 d . . .
O3 O 0.25399(18) 0.29851(16) 0.64835(13) 0.0486(4) Uani 1 1 d . . .
C1 C 0.9777(3) 0.1004(2) 0.8717(2) 0.0488(6) Uani 1 1 d . . .
C2 C 0.8372(2) 0.1757(2) 0.81555(19) 0.0409(5) Uani 1 1 d D . .
C3 C 0.8397(3) 0.1333(3) 0.6844(2) 0.0513(6) Uani 1 1 d . . .
C4 C 0.8648(3) 0.0062(3) 0.6629(2) 0.0547(6) Uani 1 1 d . . .
C5 C 0.8868(3) -0.0368(2) 0.7808(2) 0.0468(5) Uani 1 1 d . . .
C6 C 0.7006(3) -0.0579(2) 0.80810(18) 0.0370(4) Uani 1 1 d . . .
C7 C 0.5546(3) -0.1745(2) 0.7181(2) 0.0464(5) Uani 1 1 d . . .
C8 C 0.4211(3) -0.1295(2) 0.62542(19) 0.0427(5) Uani 1 1 d . . .
C9 C 0.3455(2) -0.0149(2) 0.68774(17) 0.0378(5) Uani 1 1 d . . .
C10 C 0.4914(2) 0.11291(19) 0.74077(15) 0.0296(4) Uani 1 1 d . . .
C11 C 0.6615(2) 0.09034(18) 0.82609(16) 0.0305(4) Uani 1 1 d D . .
C12 C 0.6370(2) 0.1432(2) 0.95151(17) 0.0366(4) Uani 1 1 d . . .
C13 C 0.5083(3) 0.2395(2) 0.94681(17) 0.0409(5) Uani 1 1 d . . .
C14 C 0.5715(3) 0.44255(19) 0.74386(18) 0.0356(4) Uani 1 1 d . . .
C15 C 0.7076(3) 0.5233(2) 0.84188(18) 0.0430(5) Uani 1 1 d . . .
C16 C 0.8645(3) 0.5833(2) 0.8230(2) 0.0469(5) Uani 1 1 d . . .
C17 C 0.8884(3) 0.5666(2) 0.7070(2) 0.0460(5) Uani 1 1 d . . .
C18 C 0.7493(3) 0.4886(2) 0.6105(2) 0.0508(6) Uani 1 1 d . . .
C19 C 0.5919(3) 0.4252(2) 0.62730(19) 0.0439(5) Uani 1 1 d . . .
C20 C 1.0607(4) 0.6289(3) 0.6859(3) 0.0675(7) Uani 1 1 d . . .
H1A H 0.9794 0.1042 0.9536 0.080 Uiso 1 1 d . . .
H1B H 1.1032 0.1423 0.8657 0.080 Uiso 1 1 d . . .
H2A H 0.8551 0.2779 0.8467 0.080 Uiso 1 1 d . . .
H3A H 0.8224 0.1911 0.6325 0.080 Uiso 1 1 d . . .
H4A H 0.8579 -0.0566 0.5833 0.080 Uiso 1 1 d . . .
H5A H 0.9466 -0.1122 0.7911 0.080 Uiso 1 1 d . . .
H6A H 0.7202 -0.0818 0.8908 0.080 Uiso 1 1 d . . .
H7A H 0.6170 -0.2369 0.6799 0.080 Uiso 1 1 d . . .
H7B H 0.4889 -0.2302 0.7610 0.080 Uiso 1 1 d . . .
H8A H 0.4772 -0.0949 0.5658 0.080 Uiso 1 1 d . . .
H8B H 0.3264 -0.2060 0.5798 0.080 Uiso 1 1 d . . .
H9A H 0.2481 0.0085 0.6356 0.080 Uiso 1 1 d . . .
H9B H 0.3017 -0.0407 0.7576 0.080 Uiso 1 1 d . . .
H10A H 0.5202 0.1488 0.6702 0.080 Uiso 1 1 d . . .
H13A H 0.4047 0.2115 0.9821 0.080 Uiso 1 1 d . . .
H13B H 0.5702 0.3337 0.9861 0.080 Uiso 1 1 d . . .
H15A H 0.6963 0.5387 0.9205 0.080 Uiso 1 1 d . . .
H16A H 0.9560 0.6373 0.8912 0.080 Uiso 1 1 d . . .
H18A H 0.7638 0.4782 0.5317 0.080 Uiso 1 1 d . . .
H19A H 0.4934 0.3708 0.5616 0.080 Uiso 1 1 d . . .
H20A H 1.1152 0.7018 0.7457 0.080 Uiso 1 1 d . . .
H20B H 1.1326 0.5561 0.6614 0.080 Uiso 1 1 d . . .
H20C H 1.0459 0.6790 0.6255 0.080 Uiso 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
O3 S1 O2 120.46(9) . . ?
O3 S1 N1 107.42(9) . . ?
O2 S1 N1 105.92(8) . . ?
O3 S1 C14 106.75(9) . . ?
O2 S1 C14 108.59(9) . . ?
N1 S1 C14 107.03(8) . . ?
C13 N1 C10 111.97(14) . . ?
C13 N1 S1 120.94(13) . . ?
C10 N1 S1 120.28(12) . . ?
C5 C1 C2 93.05(16) . . ?
C3 C2 C1 99.41(17) . . ?
C3 C2 C11 106.55(16) . . ?
C1 C2 C11 101.54(15) . . ?
C4 C3 C2 107.7(2) . . ?
C3 C4 C5 107.2(2) . . ?
C4 C5 C1 100.5(2) . . ?
C4 C5 C6 108.12(16) . . ?
C1 C5 C6 100.25(16) . . ?
C7 C6 C5 116.44(17) . . ?
C7 C6 C11 117.25(15) . . ?
C5 C6 C11 102.01(15) . . ?
C8 C7 C6 115.16(17) . . ?
C9 C8 C7 110.37(17) . . ?
C8 C9 C10 109.21(15) . . ?
N1 C10 C9 111.39(14) . . ?
N1 C10 C11 104.80(14) . . ?
C9 C10 C11 113.81(15) . . ?
C12 C11 C10 102.84(14) . . ?
C12 C11 C6 111.80(15) . . ?
C10 C11 C6 118.06(15) . . ?
C12 C11 C2 109.14(15) . . ?
C10 C11 C2 112.78(14) . . ?
C6 C11 C2 102.27(14) . . ?
O1 C12 C13 123.10(18) . . ?
O1 C12 C11 126.49(18) . . ?
C13 C12 C11 110.41(16) . . ?
N1 C13 C12 104.34(15) . . ?
C19 C14 C15 120.04(18) . . ?
C19 C14 S1 118.92(16) . . ?
C15 C14 S1 120.93(15) . . ?
C16 C15 C14 119.64(18) . . ?
C15 C16 C17 121.3(2) . . ?
C18 C17 C16 117.99(19) . . ?
C18 C17 C20 120.4(2) . . ?
C16 C17 C20 121.6(2) . . ?
C17 C18 C19 121.82(19) . . ?
C18 C19 C14 119.2(2) . . ?
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 O3 1.4294(15) . ?
S1 O2 1.4306(15) . ?
S1 N1 1.6209(16) . ?
S1 C14 1.765(2) . ?
N1 C13 1.464(2) . ?
N1 C10 1.495(2) . ?
O1 C12 1.207(2) . ?
C1 C5 1.531(3) . ?
C1 C2 1.534(3) . ?
C2 C3 1.512(3) . ?
C2 C11 1.5655(16) . ?
C3 C4 1.318(3) . ?
C4 C5 1.509(3) . ?
C5 C6 1.562(3) . ?
C6 C7 1.540(3) . ?
C6 C11 1.564(3) . ?
C7 C8 1.517(3) . ?
C8 C9 1.515(3) . ?
C9 C10 1.517(3) . ?
C10 C11 1.550(2) . ?
C11 C12 1.522(3) . ?
C12 C13 1.505(3) . ?
C14 C19 1.388(3) . ?
C14 C15 1.389(3) . ?
C15 C16 1.380(3) . ?
C16 C17 1.391(3) . ?
C17 C18 1.383(3) . ?
C17 C20 1.505(3) . ?
C18 C19 1.384(3) . ?
