#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/60/1506044.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_1506044
loop_
_publ_author_name
'Chen, Hung-Wei'
'Hsu, Ru-Ting'
'Chang, Meng-Yang'
'Chang, Nein-Chen'
_publ_section_title
;
 Efficient synthesis of fused bicyclic glutarimides. Its application to
 (+/-)-alloyohimbane and louisianin D.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3033
_journal_page_last               3035
_journal_paper_doi               10.1021/ol060958k
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C23 H25 N O4 S'
_chemical_formula_weight         411.50
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.164(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6243(11)
_cell_length_b                   12.1688(16)
_cell_length_c                   20.438(3)
_cell_measurement_reflns_used    4430
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.908
_cell_measurement_theta_min      2.624
_cell_volume                     2111.3(5)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11704
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.599
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4145
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0750P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1290
_reflns_number_gt                3017
_reflns_number_total             4145
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060958ksi20060421_062108.cif
_cod_data_source_block           h794-1m
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1506044
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
S S 0.01908(5) 0.69644(4) 0.22214(2) 0.05341(17) Uani 1 1 d .
O1 O 0.11805(15) 0.69323(12) 0.28621(6) 0.0699(4) Uani 1 1 d .
O2 O -0.02748(16) 0.59495(10) 0.18864(7) 0.0698(4) Uani 1 1 d .
O3 O -0.28845(17) 0.83241(11) 0.12679(7) 0.0757(4) Uani 1 1 d .
O4 O -0.47819(17) 0.52229(12) 0.20578(7) 0.0775(4) Uani 1 1 d .
N N -0.38149(16) 0.67638(11) 0.16576(7) 0.0528(4) Uani 1 1 d .
C1 C -0.15576(19) 0.77208(14) 0.23311(8) 0.0494(4) Uani 1 1 d .
H1B H -0.1258 0.8495 0.2401 0.059 Uiso 1 1 calc R
C2 C -0.2789(2) 0.76548(14) 0.17097(9) 0.0528(4) Uani 1 1 d .
C3 C -0.3906(2) 0.60068(13) 0.21664(9) 0.0536(4) Uani 1 1 d .
C4 C -0.2865(2) 0.61731(14) 0.28337(8) 0.0513(4) Uani 1 1 d .
H4A H -0.1958 0.5684 0.2845 0.062 Uiso 1 1 calc R
C5 C -0.2207(2) 0.73366(14) 0.29377(9) 0.0524(4) Uani 1 1 d .
H5A H -0.1343 0.7329 0.3320 0.063 Uiso 1 1 calc R
C6 C -0.3452(3) 0.81524(15) 0.30814(10) 0.0677(5) Uani 1 1 d .
H6A H -0.2972 0.8869 0.3175 0.081 Uiso 1 1 calc R
H6B H -0.4271 0.8220 0.2692 0.081 Uiso 1 1 calc R
C7 C -0.4179(3) 0.77841(18) 0.36690(12) 0.0810(7) Uani 1 1 d .
H7A H -0.4985 0.8303 0.3741 0.097 Uiso 1 1 calc R
H7B H -0.3377 0.7767 0.4066 0.097 Uiso 1 1 calc R
C8 C -0.4902(3) 0.66490(18) 0.35403(11) 0.0749(6) Uani 1 1 d .
H8A H -0.5343 0.6418 0.3923 0.090 Uiso 1 1 calc R
H8B H -0.5751 0.6681 0.3160 0.090 Uiso 1 1 calc R
C9 C -0.3690(2) 0.58172(16) 0.34081(10) 0.0641(5) Uani 1 1 d .
H9A H -0.4203 0.5114 0.3301 0.077 Uiso 1 1 calc R
H9B H -0.2908 0.5722 0.3808 0.077 Uiso 1 1 calc R
C10 C -0.4862(2) 0.66327(18) 0.10081(9) 0.0659(5) Uani 1 1 d .
H10A H -0.5413 0.7319 0.0889 0.079 Uiso 1 1 calc R
H10B H -0.5644 0.6074 0.1046 0.079 Uiso 1 1 calc R
C11 C -0.3975(2) 0.63115(17) 0.04625(9) 0.0617(5) Uani 1 1 d .
C12 C -0.3016(3) 0.54041(19) 0.05231(10) 0.0734(6) Uani 1 1 d .
H12A H -0.2894 0.4990 0.0911 0.088 Uiso 1 1 calc R
C13 C -0.2229(3) 0.5093(2) 0.00205(11) 0.0820(6) Uani 1 1 d .
H13A H -0.1578 0.4479 0.0075 0.098 Uiso 1 1 calc R
C14 C -0.2401(3) 0.5679(3) -0.05529(12) 0.0914(8) Uani 1 1 d .
H14A H -0.1885 0.5461 -0.0894 0.110 Uiso 1 1 calc R
C15 C -0.3337(4) 0.6593(3) -0.06239(13) 0.1053(10) Uani 1 1 d .
H15A H -0.3452 0.7001 -0.1014 0.126 Uiso 1 1 calc R
C16 C -0.4113(3) 0.6913(2) -0.01199(12) 0.0869(7) Uani 1 1 d .
H16A H -0.4737 0.7541 -0.0172 0.104 Uiso 1 1 calc R
C17 C 0.1075(2) 0.78129(15) 0.16973(9) 0.0542(4) Uani 1 1 d .
C18 C 0.2118(2) 0.86168(17) 0.19724(10) 0.0666(5) Uani 1 1 d .
H18A H 0.2382 0.8691 0.2431 0.080 Uiso 1 1 calc R
C19 C 0.2765(3) 0.93100(18) 0.15571(14) 0.0836(7) Uani 1 1 d .
H19A H 0.3463 0.9856 0.1741 0.100 Uiso 1 1 calc R
C20 C 0.2393(3) 0.9207(2) 0.08775(14) 0.0854(7) Uani 1 1 d .
C21 C 0.1344(3) 0.8397(2) 0.06140(11) 0.0873(7) Uani 1 1 d .
H21A H 0.1078 0.8326 0.0155 0.105 Uiso 1 1 calc R
C22 C 0.0686(3) 0.76946(19) 0.10127(10) 0.0716(6) Uani 1 1 d .
H22A H -0.0009 0.7148 0.0827 0.086 Uiso 1 1 calc R
C23 C 0.3134(5) 0.9984(3) 0.04413(19) 0.1425(14) Uani 1 1 d .
H23A H 0.2762 0.9809 -0.0018 0.214 Uiso 1 1 calc R
H23B H 0.4259 0.9908 0.0539 0.214 Uiso 1 1 calc R
H23C H 0.2851 1.0727 0.0526 0.214 Uiso 1 1 calc R
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
O1 S O2 118.98(9)
O1 S C17 108.71(9)
O2 S C17 109.27(8)
O1 S C1 105.98(8)
O2 S C1 109.09(8)
C17 S C1 103.71(8)
C2 N C3 124.98(14)
C2 N C10 115.64(14)
C3 N C10 119.38(14)
C2 C1 C5 111.35(14)
C2 C1 S 110.27(11)
C5 C1 S 112.24(12)
O3 C2 N 120.65(16)
O3 C2 C1 122.59(16)
N C2 C1 116.75(14)
O4 C3 N 119.72(16)
O4 C3 C4 121.54(16)
N C3 C4 118.71(14)
C3 C4 C5 113.43(14)
C3 C4 C9 111.75(15)
C5 C4 C9 111.44(14)
C1 C5 C4 110.66(14)
C1 C5 C6 109.22(15)
C4 C5 C6 111.90(15)
C7 C6 C5 111.26(16)
C6 C7 C8 110.23(17)
C9 C8 C7 111.36(17)
C8 C9 C4 112.02(16)
N C10 C11 112.47(15)
C12 C11 C16 117.5(2)
C12 C11 C10 121.15(17)
C16 C11 C10 121.3(2)
C11 C12 C13 121.4(2)
C14 C13 C12 120.4(3)
C13 C14 C15 119.4(3)
C14 C15 C16 120.4(2)
C15 C16 C11 120.9(3)
C18 C17 C22 120.58(19)
C18 C17 S 119.36(14)
C22 C17 S 120.03(15)
C17 C18 C19 119.15(19)
C20 C19 C18 121.2(2)
C19 C20 C21 118.6(2)
C19 C20 C23 119.3(3)
C21 C20 C23 122.1(3)
C22 C21 C20 121.6(2)
C21 C22 C17 118.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S O1 1.4319(13)
S O2 1.4347(13)
S C17 1.7562(19)
S C1 1.8139(17)
O3 C2 1.208(2)
O4 C3 1.213(2)
N C2 1.391(2)
N C3 1.402(2)
N C10 1.477(2)
C1 C2 1.507(2)
C1 C5 1.522(2)
C3 C4 1.508(2)
C4 C5 1.526(2)
C4 C9 1.539(2)
C5 C6 1.528(2)
C6 C7 1.517(3)
C7 C8 1.519(3)
C8 C9 1.513(3)
C10 C11 1.511(3)
C11 C12 1.372(3)
C11 C16 1.384(3)
C12 C13 1.380(3)
C13 C14 1.357(3)
C14 C15 1.366(4)
C15 C16 1.380(4)
C17 C18 1.380(3)
C17 C22 1.388(3)
C18 C19 1.382(3)
C19 C20 1.375(4)
C20 C21 1.381(3)
C20 C23 1.516(3)
C21 C22 1.371(3)
