#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:14:47 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180295 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/09/7150960.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_7150960
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            'C19 H21 N O3 S'
_chemical_formula_weight         343.43
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.7670(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6137(6)
_cell_length_b                   12.3450(8)
_cell_length_c                   15.2962(9)
_cell_measurement_reflns_used    3815
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     1738.19(19)
_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 0.960
_diffrn_measured_fraction_theta_max 0.960
_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  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10913
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.96161
_exptl_absorpt_correction_T_min  0.82682
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       Equant
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.043
_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     217
_refine_ls_number_reflns         4144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0576
_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)+(0.0633P)²+0.6116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1460
_reflns_number_gt                2942
_reflns_number_total             4144
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b806773m.txt
_cod_data_source_block           dc09m
_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.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' 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)/n
_cod_database_code               7150960
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
S1 S 0.47030(6) 0.80528(5) 0.07363(4) 0.04676(18) Uani 1 1 d . . .
O1 O 0.5132(2) 0.85834(15) 0.00200(12) 0.0617(5) Uani 1 1 d . . .
O2 O 0.4800(2) 0.69042(14) 0.08358(13) 0.0626(5) Uani 1 1 d . . .
O3 O 0.1056(2) 1.06753(14) 0.09090(14) 0.0689(5) Uani 1 1 d . . .
N1 N 0.2995(2) 0.83616(15) 0.05747(12) 0.0449(4) Uani 1 1 d . . .
C1 C 0.2513(3) 0.9471(2) 0.03109(17) 0.0547(6) Uani 1 1 d . . .
C2 C 0.1661(2) 0.98137(18) 0.09568(16) 0.0469(5) Uani 1 1 d . . .
C3 C 0.1685(2) 0.89126(17) 0.16373(15) 0.0422(5) Uani 1 1 d . . .
C4 C 0.2223(2) 0.79307(18) 0.12171(15) 0.0427(5) Uani 1 1 d . . .
C5 C 0.0830(3) 0.7325(2) 0.0716(2) 0.0631(7) Uani 1 1 d . . .
C6 C -0.0130(3) 0.7452(2) 0.1351(2) 0.0749(9) Uani 1 1 d . . .
C7 C 0.0160(3) 0.8601(2) 0.17330(19) 0.0588(7) Uani 1 1 d . . .
C8 C 0.0363(3) 0.8811(3) 0.2767(2) 0.0829(10) Uani 1 1 d . . .
C9 C 0.1446(4) 0.8010(3) 0.3306(2) 0.0874(10) Uani 1 1 d . . .
C10 C 0.2726(3) 0.8276(3) 0.32264(18) 0.0722(9) Uani 1 1 d . . .
C11 C 0.2534(3) 0.9276(2) 0.26372(17) 0.0572(6) Uani 1 1 d . . .
C12 C 0.1289(4) 0.9829(3) 0.2906(2) 0.0813(10) Uani 1 1 d . . .
C13 C 0.5696(2) 0.86202(18) 0.17873(15) 0.0410(5) Uani 1 1 d . . .
C14 C 0.6084(2) 0.97085(18) 0.18458(15) 0.0452(5) Uani 1 1 d . . .
C15 C 0.6754(2) 1.01558(19) 0.26852(16) 0.0472(5) Uani 1 1 d . . .
C16 C 0.7063(2) 0.9540(2) 0.34838(16) 0.0474(5) Uani 1 1 d . . .
C17 C 0.6707(3) 0.8446(2) 0.34050(16) 0.0522(6) Uani 1 1 d . . .
C18 C 0.6027(2) 0.79825(18) 0.25710(16) 0.0482(5) Uani 1 1 d . . .
C19 C 0.7758(3) 1.0042(2) 0.43967(19) 0.0713(8) Uani 1 1 d . . .
H1A H 0.3344 0.9988 0.0371 0.080 Uiso 1 1 d . . .
H1B H 0.1795 0.9445 -0.0318 0.080 Uiso 1 1 d . . .
H4A H 0.2905 0.7497 0.1677 0.080 Uiso 1 1 d . . .
H5A H 0.0352 0.7747 0.0087 0.080 Uiso 1 1 d . . .
H5B H 0.1051 0.6584 0.0639 0.080 Uiso 1 1 d . . .
H6A H -0.1153 0.7336 0.0995 0.080 Uiso 1 1 d . . .
H6B H 0.0199 0.6966 0.1811 0.080 Uiso 1 1 d . . .
H7A H -0.0564 0.9078 0.1380 0.080 Uiso 1 1 d . . .
H8A H -0.0494 0.8886 0.2911 0.080 Uiso 1 1 d . . .
H9A H 0.1190 0.7419 0.3547 0.080 Uiso 1 1 d . . .
H10A H 0.3561 0.7902 0.3456 0.080 Uiso 1 1 d . . .
H11A H 0.3385 0.9666 0.2664 0.080 Uiso 1 1 d . . .
H12A H 0.0862 1.0396 0.2501 0.080 Uiso 1 1 d . . .
H12B H 0.1641 1.0081 0.3503 0.080 Uiso 1 1 d . . .
H14A H 0.5946 1.0139 0.1317 0.080 Uiso 1 1 d . . .
H15A H 0.7047 1.0898 0.2727 0.080 Uiso 1 1 d . . .
H17A H 0.6934 0.8010 0.3951 0.080 Uiso 1 1 d . . .
H18A H 0.5785 0.7251 0.2514 0.080 Uiso 1 1 d . . .
H19A H 0.8238 1.0703 0.4354 0.080 Uiso 1 1 d . . .
H19B H 0.8358 0.9596 0.4716 0.080 Uiso 1 1 d . . .
H19C H 0.6954 1.0248 0.4644 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
O2 S1 O1 120.72(11) . . ?
O2 S1 N1 106.28(11) . . ?
O1 S1 N1 105.99(10) . . ?
O2 S1 C13 107.23(11) . . ?
O1 S1 C13 108.41(11) . . ?
N1 S1 C13 107.58(10) . . ?
C1 N1 C4 109.72(17) . . ?
C1 N1 S1 118.95(15) . . ?
C4 N1 S1 119.15(14) . . ?
N1 C1 C2 105.60(18) . . ?
O3 C2 C1 123.3(2) . . ?
O3 C2 C3 126.9(2) . . ?
C1 C2 C3 109.79(19) . . ?
C2 C3 C4 103.44(17) . . ?
C2 C3 C7 114.55(19) . . ?
C4 C3 C7 106.50(18) . . ?
C2 C3 C11 110.96(19) . . ?
C4 C3 C11 119.30(18) . . ?
C7 C3 C11 102.49(19) . . ?
N1 C4 C3 106.69(17) . . ?
N1 C4 C5 111.95(19) . . ?
C3 C4 C5 104.15(19) . . ?
C6 C5 C4 103.4(2) . . ?
C5 C6 C7 105.1(2) . . ?
C6 C7 C8 119.9(3) . . ?
C6 C7 C3 105.4(2) . . ?
C8 C7 C3 102.0(2) . . ?
C9 C8 C12 100.5(3) . . ?
C9 C8 C7 108.1(2) . . ?
C12 C8 C7 100.1(2) . . ?
C10 C9 C8 107.8(3) . . ?
C9 C10 C11 107.7(3) . . ?
C10 C11 C12 100.1(2) . . ?
C10 C11 C3 106.7(2) . . ?
C12 C11 C3 99.3(2) . . ?
C8 C12 C11 93.7(2) . . ?
C14 C13 C18 120.0(2) . . ?
C14 C13 S1 120.52(17) . . ?
C18 C13 S1 119.35(18) . . ?
C15 C14 C13 119.5(2) . . ?
C14 C15 C16 121.5(2) . . ?
C17 C16 C15 117.9(2) . . ?
C17 C16 C19 121.1(2) . . ?
C15 C16 C19 121.0(2) . . ?
C18 C17 C16 121.5(2) . . ?
C17 C18 C13 119.5(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 O2 1.4263(18) . ?
S1 O1 1.4351(17) . ?
S1 N1 1.6336(19) . ?
S1 C13 1.761(2) . ?
O3 C2 1.204(3) . ?
N1 C1 1.465(3) . ?
N1 C4 1.490(3) . ?
C1 C2 1.514(3) . ?
C2 C3 1.519(3) . ?
C3 C4 1.530(3) . ?
C3 C7 1.562(3) . ?
C3 C11 1.577(3) . ?
C4 C5 1.532(3) . ?
C5 C6 1.529(4) . ?
C6 C7 1.529(4) . ?
C7 C8 1.559(4) . ?
C8 C9 1.498(5) . ?
C8 C12 1.520(5) . ?
C9 C10 1.313(4) . ?
C10 C11 1.508(4) . ?
C11 C12 1.534(4) . ?
C13 C14 1.390(3) . ?
C13 C18 1.392(3) . ?
C14 C15 1.375(3) . ?
C15 C16 1.396(3) . ?
C16 C17 1.390(3) . ?
C16 C19 1.498(4) . ?
C17 C18 1.379(3) . ?
