#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/87/1508751.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_1508751
loop_
_publ_author_name
'Zhou, Rong'
'Wang, Jianfang'
'Duan, Chong'
'He, Zhengjie'
_publ_section_title
;
 Phosphine-Triggered Tandem Annulation between Morita-Baylis-Hillman
 Carbonates and Dinucleophiles: Facile Syntheses of Oxazepanes,
 Thiazepanes, and Diazepanes.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6134
_journal_page_last               6137
_journal_paper_doi               10.1021/ol302696e
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C32 H44 N2 O8 S2'
_chemical_formula_weight         648.81
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 109.43(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.058(9)
_cell_length_b                   12.865(4)
_cell_length_c                   11.153(4)
_cell_measurement_reflns_used    4757
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.2
_cell_measurement_theta_min      1.7
_cell_volume                     3391(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.22
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15431
_diffrn_reflns_theta_full        26.07
_diffrn_reflns_theta_max         26.07
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.9755
_exptl_absorpt_correction_T_min  0.9597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0569
_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)+(0.0532P)²+0.1692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1259
_reflns_number_gt                2809
_reflns_number_total             3350
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302696e_si_003.cif
_cod_data_source_block           m110727b1
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1508751
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'
'-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
S1 S 0.18263(2) 0.05297(4) 0.47316(5) 0.02767(19) Uani 1 1 d .
O1 O 0.18115(7) 0.08085(12) 0.34765(14) 0.0336(4) Uani 1 1 d .
O2 O 0.19568(7) -0.05164(11) 0.51741(16) 0.0343(4) Uani 1 1 d .
O3 O 0.39572(7) 0.14822(12) 0.78286(16) 0.0348(4) Uani 1 1 d .
O4 O 0.34176(6) 0.00272(11) 0.74228(15) 0.0284(4) Uani 1 1 d .
N1 N 0.22986(7) 0.12910(13) 0.57040(17) 0.0235(4) Uani 1 1 d .
C1 C 0.11747(9) 0.08763(16) 0.4903(2) 0.0258(5) Uani 1 1 d .
C2 C 0.08221(10) 0.15968(17) 0.4080(2) 0.0326(6) Uani 1 1 d .
H2 H 0.0916 0.1869 0.3384 0.039 Uiso 1 1 calc R
C3 C 0.03306(10) 0.19116(18) 0.4293(2) 0.0338(6) Uani 1 1 d .
H3 H 0.0088 0.2399 0.3730 0.041 Uiso 1 1 calc R
C4 C 0.01845(10) 0.15311(17) 0.5310(2) 0.0312(6) Uani 1 1 d .
C5 C 0.05420(10) 0.08002(17) 0.6115(2) 0.0320(6) Uani 1 1 d .
H5 H 0.0446 0.0520 0.6805 0.038 Uiso 1 1 calc R
C6 C 0.10331(10) 0.04811(16) 0.5919(2) 0.0292(6) Uani 1 1 d .
H6 H 0.1274 -0.0009 0.6478 0.035 Uiso 1 1 calc R
C7 C -0.03483(10) 0.18843(19) 0.5528(3) 0.0409(7) Uani 1 1 d .
H7A H -0.0529 0.2432 0.4916 0.061 Uiso 1 1 calc R
H7B H -0.0255 0.2156 0.6394 0.061 Uiso 1 1 calc R
H7C H -0.0608 0.1295 0.5414 0.061 Uiso 1 1 calc R
C8 C 0.22742(9) 0.23933(15) 0.5301(2) 0.0254(5) Uani 1 1 d .
H8A H 0.2334 0.2852 0.6047 0.030 Uiso 1 1 calc R
H8B H 0.1896 0.2547 0.4680 0.030 Uiso 1 1 calc R
C9 C 0.24260(9) 0.11125(17) 0.7093(2) 0.0259(5) Uani 1 1 d .
H9A H 0.2422 0.0358 0.7265 0.031 Uiso 1 1 calc R
H9B H 0.2134 0.1451 0.7378 0.031 Uiso 1 1 calc R
C10 C 0.29981(10) 0.15565(17) 0.7806(2) 0.0268(5) Uani 1 1 d .
C11 C 0.30654(11) 0.23989(19) 0.8508(2) 0.0407(7) Uani 1 1 d .
H11A H 0.2744 0.2752 0.8580 0.049 Uiso 1 1 calc R
H11B H 0.3435 0.2654 0.8944 0.049 Uiso 1 1 calc R
C12 C 0.35145(10) 0.10384(17) 0.7683(2) 0.0260(5) Uani 1 1 d .
C13 C 0.38398(10) -0.06429(17) 0.7136(2) 0.0305(6) Uani 1 1 d .
C14 C 0.35363(12) -0.16799(19) 0.6882(3) 0.0480(8) Uani 1 1 d .
H14A H 0.3457 -0.1906 0.7645 0.072 Uiso 1 1 calc R
H14B H 0.3776 -0.2197 0.6663 0.072 Uiso 1 1 calc R
H14C H 0.3180 -0.1607 0.6175 0.072 Uiso 1 1 calc R
C15 C 0.39403(11) -0.02273(19) 0.5958(2) 0.0375(6) Uani 1 1 d .
H15A H 0.3576 -0.0116 0.5286 0.056 Uiso 1 1 calc R
H15B H 0.4164 -0.0730 0.5667 0.056 Uiso 1 1 calc R
H15C H 0.4146 0.0433 0.6160 0.056 Uiso 1 1 calc R
C16 C 0.43781(11) -0.0709(2) 0.8269(2) 0.0416(7) Uani 1 1 d .
H16A H 0.4558 -0.0023 0.8436 0.062 Uiso 1 1 calc R
H16B H 0.4638 -0.1207 0.8088 0.062 Uiso 1 1 calc R
H16C H 0.4288 -0.0941 0.9016 0.062 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O2 S1 O1 119.99(10) . .
O2 S1 N1 107.55(10) . .
O1 S1 N1 105.98(10) . .
O2 S1 C1 108.27(10) . .
O1 S1 C1 108.58(11) . .
N1 S1 C1 105.56(10) . .
C12 O4 C13 121.49(17) . .
C8 N1 C9 115.79(16) . .
C8 N1 S1 115.04(14) . .
C9 N1 S1 116.96(14) . .
C6 C1 C2 120.1(2) . .
C6 C1 S1 119.49(17) . .
C2 C1 S1 120.24(18) . .
C3 C2 C1 119.0(2) . .
C3 C2 H2 120.5 . .
C1 C2 H2 120.5 . .
C2 C3 C4 121.7(2) . .
C2 C3 H3 119.2 . .
C4 C3 H3 119.2 . .
C3 C4 C5 118.3(2) . .
C3 C4 C7 120.9(2) . .
C5 C4 C7 120.8(2) . .
C6 C5 C4 120.8(2) . .
C6 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
C5 C6 C1 120.2(2) . .
C5 C6 H6 119.9 . .
C1 C6 H6 119.9 . .
C4 C7 H7A 109.5 . .
C4 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C4 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N1 C8 C8 110.2(2) . 7_556
N1 C8 H8A 109.6 . .
C8 C8 H8A 109.6 7_556 .
N1 C8 H8B 109.6 . .
C8 C8 H8B 109.6 7_556 .
H8A C8 H8B 108.1 . .
N1 C9 C10 109.15(19) . .
N1 C9 H9A 109.9 . .
C10 C9 H9A 109.9 . .
N1 C9 H9B 109.9 . .
C10 C9 H9B 109.9 . .
H9A C9 H9B 108.3 . .
C11 C10 C9 122.7(2) . .
C11 C10 C12 118.5(2) . .
C9 C10 C12 118.85(19) . .
C10 C11 H11A 120.0 . .
C10 C11 H11B 120.0 . .
H11A C11 H11B 120.0 . .
O3 C12 O4 125.5(2) . .
O3 C12 C10 123.9(2) . .
O4 C12 C10 110.60(19) . .
O4 C13 C16 110.84(19) . .
O4 C13 C14 101.71(19) . .
C16 C13 C14 111.0(2) . .
O4 C13 C15 108.58(18) . .
C16 C13 C15 112.6(2) . .
C14 C13 C15 111.5(2) . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C13 C16 H16A 109.5 . .
C13 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C13 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.4333(16) .
S1 O1 1.4335(17) .
S1 N1 1.6378(19) .
S1 C1 1.763(2) .
O3 C12 1.210(3) .
O4 C12 1.337(3) .
O4 C13 1.480(3) .
N1 C8 1.483(2) .
N1 C9 1.492(3) .
C1 C6 1.391(3) .
C1 C2 1.394(3) .
C2 C3 1.390(3) .
C2 H2 0.9500 .
C3 C4 1.391(3) .
C3 H3 0.9500 .
C4 C5 1.399(3) .
C4 C7 1.504(3) .
C5 C6 1.382(3) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C8 1.520(4) 7_556
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.502(3) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.315(3) .
C10 C12 1.502(3) .
C11 H11A 0.9500 .
C11 H11B 0.9500 .
C13 C16 1.513(3) .
C13 C14 1.515(3) .
C13 C15 1.515(3) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
O2 S1 N1 C8 172.50(15) .
O1 S1 N1 C8 43.01(17) .
C1 S1 N1 C8 -72.07(17) .
O2 S1 N1 C9 -46.56(18) .
O1 S1 N1 C9 -176.06(15) .
C1 S1 N1 C9 68.87(17) .
O2 S1 C1 C6 33.8(2) .
O1 S1 C1 C6 165.56(16) .
N1 S1 C1 C6 -81.17(19) .
O2 S1 C1 C2 -150.69(17) .
O1 S1 C1 C2 -18.9(2) .
N1 S1 C1 C2 94.38(19) .
C6 C1 C2 C3 0.1(3) .
S1 C1 C2 C3 -175.42(17) .
C1 C2 C3 C4 0.4(3) .
C2 C3 C4 C5 -1.1(3) .
C2 C3 C4 C7 179.8(2) .
C3 C4 C5 C6 1.3(3) .
C7 C4 C5 C6 -179.6(2) .
C4 C5 C6 C1 -0.8(3) .
C2 C1 C6 C5 0.1(3) .
S1 C1 C6 C5 175.62(16) .
C9 N1 C8 C8 118.4(2) 7_556
S1 N1 C8 C8 -100.2(2) 7_556
C8 N1 C9 C10 -61.2(2) .
S1 N1 C9 C10 158.18(15) .
N1 C9 C10 C11 108.7(3) .
N1 C9 C10 C12 -69.4(2) .
C13 O4 C12 O3 -7.2(3) .
C13 O4 C12 C10 174.24(18) .
C11 C10 C12 O3 -24.3(3) .
C9 C10 C12 O3 153.9(2) .
C11 C10 C12 O4 154.3(2) .
C9 C10 C12 O4 -27.5(3) .
C12 O4 C13 C16 63.2(3) .
C12 O4 C13 C14 -178.7(2) .
C12 O4 C13 C15 -61.0(3) .
