Supplementary Material for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2006


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'P. Steel'
_publ_contact_author_address     
;
Chemistry Department
Durham University
University Science Laboratories
South Road
Durham
DH1 3LE
UNITED KINGDOM
;

_publ_contact_author_email       P.G.STEEL@DURHAM.AC.UK

_publ_section_title              
;
The Dihydrofuran Template Approach To Furofuran
Synthesis
;
loop_
_publ_author_name
'P. Steel'
'David J. Aldous'
'Andrei S. Batsanov'
'Anne J. Dalencon'
'William M. Dutton'
;
D.S.Yufit
;

data_(1)
_database_code_depnum_ccdc_archive 'CCDC 603915'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 2-endo,6-endo-bis(3',4'-methylenedioxyphenyl)
-3,7-dioxa-bicyclo[3.3.0]octane
;
_chemical_name_common            
;2-endo,6-endo-bis(3',4'-methylenedioxyphenyl) -3,7-dioxa-
bicyclo(3.3.0)octane
;
_chemical_melting_point          414(1)
_chemical_formula_moiety         'C20 H18 O6'
_chemical_formula_sum            'C20 H18 O6'
_chemical_formula_weight         354.34

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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'

_cell_length_a                   8.1928(10)
_cell_length_b                   7.4438(9)
_cell_length_c                   26.234(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.98(1)
_cell_angle_gamma                90.00
_cell_volume                     1588.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    883
_cell_measurement_theta_min      12.05
_cell_measurement_theta_max      26.13

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;The data collection nominally covered full sphere
of reciprocal space, by a combination of 5 sets of \w scans;
each set at different \f and/or 2\q angles and each
scan (15 sec exposure) covering 0.3\% in \w. Crystal to
detector distance 4.58 cm.
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SMART 1K CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 8
_diffrn_standards_number         0
_diffrn_reflns_number            18649
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         29.07
_reflns_number_total             4226
_reflns_number_gt                3562
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART version 5.060 (Bruker, 1999)'
_computing_cell_refinement       'SMART version 5.060 (Bruker, 1999)'
_computing_data_reduction        'SAINT version 6.02A (Bruker, 2001)'
_computing_structure_solution    'SHELXTL version 6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXTL version 6.12 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL version 6.12 (Bruker, 2001)'
_computing_publication_material  'SHELXTL version 6.12 (Bruker, 2001)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0566P)^2^+0.5918P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4226
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.53955(14) 0.52517(15) 0.22635(4) 0.0158(2) Uani 1 1 d . . .
H1 H 0.5718 0.3994 0.2187 0.019 Uiso 1 1 calc R . .
C2 C 0.41210(14) 0.60102(16) 0.18320(4) 0.0163(2) Uani 1 1 d . . .
H2 H 0.3436 0.4993 0.1676 0.020 Uiso 1 1 calc R . .
O3 O 0.30955(11) 0.71724(12) 0.20862(3) 0.01914(19) Uani 1 1 d . . .
C4 C 0.28333(14) 0.62567(16) 0.25492(5) 0.0176(2) Uani 1 1 d . . .
H41 H 0.1943 0.5358 0.2480 0.021 Uiso 1 1 calc R . .
H42 H 0.2521 0.7121 0.2807 0.021 Uiso 1 1 calc R . .
C5 C 0.44632(14) 0.53279(15) 0.27463(4) 0.0156(2) Uani 1 1 d . . .
H5 H 0.4274 0.4097 0.2880 0.019 Uiso 1 1 calc R . .
C6 C 0.56486(14) 0.64210(16) 0.31311(5) 0.0170(2) Uani 1 1 d . . .
H6 H 0.6463 0.5567 0.3313 0.020 Uiso 1 1 calc R . .
O7 O 0.65076(11) 0.75705(12) 0.28213(3) 0.0199(2) Uani 1 1 d . . .
C8 C 0.69111(15) 0.64371(16) 0.24149(5) 0.0183(2) Uani 1 1 d . . .
H81 H 0.7882 0.5687 0.2533 0.022 Uiso 1 1 calc R . .
H82 H 0.7161 0.7167 0.2119 0.022 Uiso 1 1 calc R . .
C11 C 0.48248(14) 0.70075(16) 0.14098(4) 0.0170(2) Uani 1 1 d . . .
C12 C 0.48891(15) 0.88968(17) 0.14091(5) 0.0195(2) Uani 1 1 d . . .
H12 H 0.4451 0.9591 0.1664 0.023 Uiso 1 1 calc R . .
C13 C 0.56187(15) 0.96863(16) 0.10202(5) 0.0195(2) Uani 1 1 d . . .
C14 C 0.62781(16) 0.87062(18) 0.06481(5) 0.0214(3) Uani 1 1 d . . .
C15 C 0.62297(17) 0.68606(18) 0.06399(5) 0.0240(3) Uani 1 1 d . . .
H15 H 0.6683 0.6186 0.0384 0.029 Uiso 1 1 calc R . .
C16 C 0.54753(16) 0.60279(17) 0.10296(5) 0.0217(3) Uani 1 1 d . . .
H16 H 0.5406 0.4754 0.1035 0.026 Uiso 1 1 calc R . .
O17 O 0.58297(14) 1.14918(13) 0.09382(4) 0.0319(3) Uani 1 1 d . . .
C18 C 0.66987(18) 1.16190(19) 0.04991(5) 0.0253(3) Uani 1 1 d . . .
H181 H 0.7779 1.2202 0.0595 0.030 Uiso 1 1 calc R . .
H182 H 0.6064 1.2354 0.0230 0.030 Uiso 1 1 calc R . .
O19 O 0.69279(14) 0.98408(14) 0.03092(4) 0.0309(2) Uani 1 1 d . . .
C21 C 0.49122(15) 0.75029(17) 0.35318(5) 0.0182(2) Uani 1 1 d . . .
C22 C 0.52236(15) 0.93525(17) 0.35864(5) 0.0187(2) Uani 1 1 d . . .
H22 H 0.5849 0.9979 0.3361 0.022 Uiso 1 1 calc R . .
C23 C 0.45818(15) 1.02169(17) 0.39810(5) 0.0197(2) Uani 1 1 d . . .
C24 C 0.36738(15) 0.93289(18) 0.43150(5) 0.0209(3) Uani 1 1 d . . .
C25 C 0.33270(17) 0.75306(19) 0.42652(5) 0.0252(3) Uani 1 1 d . . .
H25 H 0.2683 0.6928 0.4490 0.030 Uiso 1 1 calc R . .
C26 C 0.39727(16) 0.66256(18) 0.38652(5) 0.0230(3) Uani 1 1 d . . .
H26 H 0.3764 0.5377 0.3820 0.028 Uiso 1 1 calc R . .
O27 O 0.47325(13) 1.19995(13) 0.41133(4) 0.0299(2) Uani 1 1 d . . .
C28 C 0.37646(18) 1.22384(19) 0.45265(5) 0.0266(3) Uani 1 1 d . . .
H281 H 0.2798 1.3002 0.4414 0.032 Uiso 1 1 calc R . .
H282 H 0.4426 1.2838 0.4819 0.032 Uiso 1 1 calc R . .
O29 O 0.32358(12) 1.05085(14) 0.46808(4) 0.0271(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0153(5) 0.0131(5) 0.0188(5) -0.0007(4) 0.0018(4) 0.0014(4)
C2 0.0163(5) 0.0146(5) 0.0182(5) -0.0011(4) 0.0022(4) 0.0019(4)
O3 0.0197(4) 0.0186(4) 0.0200(4) 0.0031(3) 0.0061(3) 0.0066(3)
C4 0.0167(5) 0.0176(5) 0.0188(5) 0.0016(4) 0.0033(4) 0.0007(4)
C5 0.0159(5) 0.0123(5) 0.0185(5) 0.0009(4) 0.0012(4) -0.0007(4)
C6 0.0168(5) 0.0157(5) 0.0183(5) 0.0009(4) 0.0019(4) -0.0031(4)
O7 0.0213(4) 0.0184(4) 0.0213(4) -0.0041(3) 0.0080(3) -0.0065(3)
C8 0.0162(5) 0.0191(5) 0.0198(5) -0.0030(4) 0.0030(4) -0.0006(4)
C11 0.0168(5) 0.0165(5) 0.0178(5) 0.0011(4) 0.0017(4) 0.0021(4)
C12 0.0216(6) 0.0180(6) 0.0194(6) -0.0012(4) 0.0040(4) 0.0018(4)
C13 0.0221(6) 0.0146(5) 0.0216(6) 0.0007(4) 0.0022(5) 0.0013(4)
C14 0.0219(6) 0.0241(6) 0.0187(5) 0.0032(5) 0.0042(4) 0.0015(5)
C15 0.0293(7) 0.0228(6) 0.0214(6) -0.0030(5) 0.0085(5) 0.0044(5)
C16 0.0261(6) 0.0166(6) 0.0230(6) -0.0014(5) 0.0055(5) 0.0018(5)
O17 0.0463(6) 0.0158(5) 0.0377(6) 0.0032(4) 0.0214(5) 0.0003(4)
C18 0.0313(7) 0.0239(6) 0.0208(6) 0.0036(5) 0.0037(5) -0.0036(5)
O19 0.0426(6) 0.0245(5) 0.0291(5) 0.0050(4) 0.0186(4) 0.0020(4)
C21 0.0174(5) 0.0199(6) 0.0167(5) 0.0007(4) 0.0004(4) -0.0019(4)
C22 0.0193(5) 0.0191(6) 0.0181(5) 0.0006(4) 0.0038(4) -0.0024(4)
C23 0.0204(6) 0.0185(6) 0.0199(6) -0.0016(5) 0.0011(4) 0.0006(5)
C24 0.0202(6) 0.0281(6) 0.0140(5) -0.0004(5) 0.0014(4) 0.0025(5)
C25 0.0270(6) 0.0290(7) 0.0205(6) 0.0032(5) 0.0070(5) -0.0043(5)
C26 0.0265(6) 0.0214(6) 0.0217(6) 0.0007(5) 0.0053(5) -0.0053(5)
O27 0.0383(6) 0.0212(5) 0.0328(5) -0.0063(4) 0.0152(4) -0.0009(4)
C28 0.0327(7) 0.0276(7) 0.0197(6) -0.0034(5) 0.0040(5) 0.0048(6)
O29 0.0314(5) 0.0304(5) 0.0207(4) -0.0029(4) 0.0081(4) 0.0034(4)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C8 1.5356(16) . ?
C1 C2 1.5502(16) . ?
C1 C5 1.5577(17) . ?
C1 H1 1.0000 . ?
C2 O3 1.4267(14) . ?
C2 C11 1.5052(16) . ?
C2 H2 1.0000 . ?
O3 C4 1.4317(14) . ?
C4 C5 1.5364(16) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 C6 1.5446(16) . ?
C5 H5 1.0000 . ?
C6 O7 1.4237(14) . ?
C6 C21 1.5074(17) . ?
C6 H6 1.0000 . ?
O7 C8 1.4295(14) . ?
C8 H81 0.9900 . ?
C8 H82 0.9900 . ?
C11 C16 1.3927(16) . ?
C11 C12 1.4074(17) . ?
C12 C13 1.3754(17) . ?
C12 H12 0.9500 . ?
C13 O17 1.3754(15) . ?
C13 C14 1.3802(17) . ?
C14 C15 1.3745(19) . ?
C14 O19 1.3792(15) . ?
C15 C16 1.4018(18) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
O17 C18 1.4289(16) . ?
C18 O19 1.4347(17) . ?
C18 H181 0.9900 . ?
C18 H182 0.9900 . ?
C21 C26 1.3954(17) . ?
C21 C22 1.4044(17) . ?
C22 C23 1.3763(17) . ?
C22 H22 0.9500 . ?
C23 O27 1.3733(16) . ?
C23 C24 1.3844(18) . ?
C24 C25 1.3714(19) . ?
C24 O29 1.3800(15) . ?
C25 C26 1.4034(18) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
O27 C28 1.4299(16) . ?
C28 O29 1.4325(18) . ?
C28 H281 0.9900 . ?
C28 H282 0.9900 . ?

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
C8 C1 C2 115.55(10) . . ?
C8 C1 C5 103.28(9) . . ?
C2 C1 C5 103.13(9) . . ?
C8 C1 H1 111.4 . . ?
C2 C1 H1 111.4 . . ?
C5 C1 H1 111.4 . . ?
O3 C2 C11 110.18(9) . . ?
O3 C2 C1 105.20(9) . . ?
C11 C2 C1 115.64(10) . . ?
O3 C2 H2 108.5 . . ?
C11 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
C2 O3 C4 105.40(9) . . ?
O3 C4 C5 106.61(9) . . ?
O3 C4 H41 110.4 . . ?
C5 C4 H41 110.4 . . ?
O3 C4 H42 110.4 . . ?
C5 C4 H42 110.4 . . ?
H41 C4 H42 108.6 . . ?
C4 C5 C6 115.76(10) . . ?
C4 C5 C1 103.58(9) . . ?
C6 C5 C1 102.65(9) . . ?
C4 C5 H5 111.4 . . ?
C6 C5 H5 111.4 . . ?
C1 C5 H5 111.4 . . ?
O7 C6 C21 110.16(10) . . ?
O7 C6 C5 105.00(9) . . ?
C21 C6 C5 117.65(10) . . ?
O7 C6 H6 107.9 . . ?
C21 C6 H6 107.9 . . ?
C5 C6 H6 107.9 . . ?
C6 O7 C8 104.25(9) . . ?
O7 C8 C1 106.20(9) . . ?
O7 C8 H81 110.5 . . ?
C1 C8 H81 110.5 . . ?
O7 C8 H82 110.5 . . ?
C1 C8 H82 110.5 . . ?
H81 C8 H82 108.7 . . ?
C16 C11 C12 120.31(11) . . ?
C16 C11 C2 118.87(11) . . ?
C12 C11 C2 120.76(11) . . ?
C13 C12 C11 116.59(11) . . ?
C13 C12 H12 121.7 . . ?
C11 C12 H12 121.7 . . ?
O17 C13 C12 127.43(11) . . ?
O17 C13 C14 109.78(11) . . ?
C12 C13 C14 122.79(12) . . ?
C15 C14 O19 127.92(12) . . ?
C15 C14 C13 121.76(12) . . ?
O19 C14 C13 110.31(11) . . ?
C14 C15 C16 116.42(12) . . ?
C14 C15 H15 121.8 . . ?
C16 C15 H15 121.8 . . ?
C11 C16 C15 122.12(12) . . ?
C11 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C13 O17 C18 105.98(10) . . ?
O17 C18 O19 108.53(10) . . ?
O17 C18 H181 110.0 . . ?
O19 C18 H181 110.0 . . ?
O17 C18 H182 110.0 . . ?
O19 C18 H182 110.0 . . ?
H181 C18 H182 108.4 . . ?
C14 O19 C18 105.31(10) . . ?
C26 C21 C22 120.14(11) . . ?
C26 C21 C6 119.02(11) . . ?
C22 C21 C6 120.78(11) . . ?
C23 C22 C21 116.98(11) . . ?
C23 C22 H22 121.5 . . ?
C21 C22 H22 121.5 . . ?
O27 C23 C22 127.66(12) . . ?
O27 C23 C24 109.88(11) . . ?
C22 C23 C24 122.46(12) . . ?
C25 C24 O29 128.24(12) . . ?
C25 C24 C23 121.79(12) . . ?
O29 C24 C23 109.97(12) . . ?
C24 C25 C26 116.57(12) . . ?
C24 C25 H25 121.7 . . ?
C26 C25 H25 121.7 . . ?
C21 C26 C25 122.05(12) . . ?
C21 C26 H26 119.0 . . ?
C25 C26 H26 119.0 . . ?
C23 O27 C28 105.70(10) . . ?
O27 C28 O29 108.48(10) . . ?
O27 C28 H281 110.0 . . ?
O29 C28 H281 110.0 . . ?
O27 C28 H282 110.0 . . ?
O29 C28 H282 110.0 . . ?
H281 C28 H282 108.4 . . ?
C24 O29 C28 105.21(10) . . ?

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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C1 C2 O3 -84.81(11) . . . . ?
C5 C1 C2 O3 27.09(11) . . . . ?
C8 C1 C2 C11 36.99(14) . . . . ?
C5 C1 C2 C11 148.89(10) . . . . ?
C11 C2 O3 C4 -165.98(9) . . . . ?
C1 C2 O3 C4 -40.70(11) . . . . ?
C2 O3 C4 C5 37.94(12) . . . . ?
O3 C4 C5 C6 92.13(11) . . . . ?
O3 C4 C5 C1 -19.38(12) . . . . ?
C8 C1 C5 C4 116.15(10) . . . . ?
C2 C1 C5 C4 -4.52(11) . . . . ?
C8 C1 C5 C6 -4.68(11) . . . . ?
C2 C1 C5 C6 -125.35(10) . . . . ?
C4 C5 C6 O7 -83.05(12) . . . . ?
C1 C5 C6 O7 29.01(11) . . . . ?
C4 C5 C6 C21 39.84(14) . . . . ?
C1 C5 C6 C21 151.90(10) . . . . ?
C21 C6 O7 C8 -171.20(9) . . . . ?
C5 C6 O7 C8 -43.60(11) . . . . ?
C6 O7 C8 C1 40.61(11) . . . . ?
C2 C1 C8 O7 90.86(11) . . . . ?
C5 C1 C8 O7 -20.96(12) . . . . ?
O3 C2 C11 C16 -162.54(10) . . . . ?
C1 C2 C11 C16 78.37(14) . . . . ?
O3 C2 C11 C12 20.06(15) . . . . ?
C1 C2 C11 C12 -99.03(13) . . . . ?
C2 C11 C12 C13 177.22(11) . . . . ?
C11 C12 C13 O17 -179.92(13) . . . . ?
O17 C13 C14 C15 -179.87(12) . . . . ?
O17 C13 C14 O19 -0.49(15) . . . . ?
C12 C13 C14 O19 -179.88(12) . . . . ?
O19 C14 C15 C16 -179.28(13) . . . . ?
C2 C11 C16 C15 -176.56(12) . . . . ?
C12 C13 O17 C18 177.98(13) . . . . ?
C14 C13 O17 C18 -1.37(15) . . . . ?
C13 O17 C18 O19 2.68(15) . . . . ?
C15 C14 O19 C18 -178.55(14) . . . . ?
C13 C14 O19 C18 2.12(15) . . . . ?
O17 C18 O19 C14 -2.95(14) . . . . ?
O7 C6 C21 C26 178.00(11) . . . . ?
C5 C6 C21 C26 57.77(15) . . . . ?
O7 C6 C21 C22 -4.87(15) . . . . ?
C5 C6 C21 C22 -125.09(12) . . . . ?
C6 C21 C22 C23 -176.33(11) . . . . ?
C21 C22 C23 O27 179.32(12) . . . . ?
O27 C23 C24 C25 179.36(12) . . . . ?
O27 C23 C24 O29 -1.17(15) . . . . ?
C22 C23 C24 O29 178.00(11) . . . . ?
O29 C24 C25 C26 -177.92(12) . . . . ?
C6 C21 C26 C25 176.40(12) . . . . ?
C22 C23 O27 C28 176.55(13) . . . . ?
C24 C23 O27 C28 -4.33(14) . . . . ?
C23 O27 C28 O29 8.10(14) . . . . ?
C25 C24 O29 C28 -174.46(14) . . . . ?
C23 C24 O29 C28 6.12(14) . . . . ?
O27 C28 O29 C24 -8.74(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        29.07
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.060

#==============================================END

data_(15)
_database_code_depnum_ccdc_archive 'CCDC 603916'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; N-toluenesulfonyl-3-methoxycarbonyl-2-phenyl-3-pyrroline
;
_chemical_name_common            
N-toluenesulfonyl-3-methoxycarbonyl-2-phenyl-3-pyrroline
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N O4 S'
_chemical_formula_sum            'C19 H19 N O4 S'
_chemical_formula_weight         357.41

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8932(4)
_cell_length_b                   9.2189(7)
_cell_length_c                   16.1992(13)
_cell_angle_alpha                87.502(3)
_cell_angle_beta                 89.201(3)
_cell_angle_gamma                77.553(3)
_cell_volume                     858.57(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    1781
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      26.35

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      110.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       \w-scan
_diffrn_detector_area_resol_mean 8
_diffrn_standards_number         0
_diffrn_reflns_number            8583
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_sigmaI/netI    0.1039
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3371
_reflns_number_gt                2145
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART version 5.054 (Bruker, 1998)'
_computing_cell_refinement       'SMART version 5.054 (Bruker, 1998)'
_computing_data_reduction        'SAINT version 6.01 (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL version 5.10 (Bruker, 1997)'
_computing_publication_material  'SHELXTL version 5.10 (Bruker, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.
Methyl groups were refined as rigid bodies rotating around C---C or
O---C bonds, with a common refined U for three H atoms. Other H atoms:
"riding" model (constr).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3371
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1355
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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
S S 0.74394(14) 0.50787(9) 0.24362(5) 0.0173(2) Uani 1 1 d . . .
O1 O 0.9255(4) 0.5858(2) 0.25575(13) 0.0237(5) Uani 1 1 d . . .
O2 O 0.7987(4) 0.3504(2) 0.23228(13) 0.0233(5) Uani 1 1 d . . .
O3 O 0.0261(4) 0.7405(2) 0.51451(13) 0.0225(5) Uani 1 1 d . . .
O4 O 0.3513(4) 0.8319(2) 0.51941(14) 0.0279(6) Uani 1 1 d . . .
N N 0.5770(4) 0.5322(3) 0.32400(15) 0.0152(6) Uani 1 1 d . . .
C1 C 0.5308(5) 0.6721(3) 0.37094(18) 0.0159(7) Uani 1 1 d . . .
H1 H 0.6690 0.6755 0.4054 0.019 Uiso 1 1 calc R . .
C2 C 0.3337(5) 0.6435(3) 0.42624(18) 0.0168(7) Uani 1 1 d . . .
C3 C 0.2637(5) 0.5209(3) 0.40894(18) 0.0183(7) Uani 1 1 d . . .
H3 H 0.1388 0.4886 0.4365 0.022 Uiso 1 1 calc R . .
C4 C 0.4041(5) 0.4393(3) 0.34100(19) 0.0191(7) Uani 1 1 d . . .
H41 H 0.4798 0.3367 0.3595 0.023 Uiso 1 1 calc R . .
H42 H 0.3076 0.4359 0.2919 0.023 Uiso 1 1 calc R . .
C5 C 0.4637(5) 0.8144(3) 0.31815(18) 0.0160(7) Uani 1 1 d . . .
C6 C 0.6037(6) 0.9174(3) 0.3145(2) 0.0219(8) Uani 1 1 d . . .
H6 H 0.7429 0.8991 0.3457 0.026 Uiso 1 1 calc R . .
C7 C 0.5426(6) 1.0479(4) 0.2653(2) 0.0285(8) Uani 1 1 d . . .
H7 H 0.6414 1.1169 0.2625 0.034 Uiso 1 1 calc R . .
C8 C 0.3386(6) 1.0766(4) 0.2209(2) 0.0288(9) Uani 1 1 d . . .
H8 H 0.2967 1.1655 0.1875 0.035 Uiso 1 1 calc R . .
C9 C 0.1954(6) 0.9759(4) 0.2250(2) 0.0266(8) Uani 1 1 d . . .
H9 H 0.0547 0.9962 0.1945 0.032 Uiso 1 1 calc R . .
C10 C 0.2559(5) 0.8448(3) 0.27342(19) 0.0204(7) Uani 1 1 d . . .
H10 H 0.1564 0.7762 0.2761 0.024 Uiso 1 1 calc R . .
C11 C 0.2423(6) 0.7497(3) 0.49087(19) 0.0191(7) Uani 1 1 d . . .
C12 C -0.0734(6) 0.8356(4) 0.5804(2) 0.0273(8) Uani 1 1 d . . .
H121 H -0.0366 0.9338 0.5711 0.041(6) Uiso 1 1 calc R . .
H122 H -0.0085 0.7916 0.6334 0.041(6) Uiso 1 1 calc R . .
H123 H -0.2424 0.8459 0.5814 0.041(6) Uiso 1 1 calc R . .
C13 C 0.5837(6) 0.5916(3) 0.15613(19) 0.0200(7) Uani 1 1 d . . .
C14 C 0.4061(6) 0.5328(4) 0.1257(2) 0.0249(8) Uani 1 1 d . . .
H14 H 0.3754 0.4432 0.1498 0.030 Uiso 1 1 calc R . .
C15 C 0.2734(6) 0.6044(4) 0.0603(2) 0.0320(9) Uani 1 1 d . . .
H15 H 0.1495 0.5647 0.0405 0.038 Uiso 1 1 calc R . .
C16 C 0.3196(7) 0.7343(4) 0.0232(2) 0.0338(10) Uani 1 1 d . . .
C17 C 0.5021(7) 0.7875(4) 0.0525(2) 0.0341(9) Uani 1 1 d . . .
H17 H 0.5391 0.8737 0.0262 0.041 Uiso 1 1 calc R . .
C18 C 0.6341(6) 0.7199(4) 0.1192(2) 0.0267(8) Uani 1 1 d . . .
H18 H 0.7568 0.7604 0.1393 0.032 Uiso 1 1 calc R . .
C19 C 0.1712(8) 0.8125(5) -0.0480(2) 0.0501(13) Uani 1 1 d . . .
H191 H 0.1695 0.7422 -0.0915 0.092(10) Uiso 1 1 calc R . .
H192 H 0.2359 0.8957 -0.0701 0.092(10) Uiso 1 1 calc R . .
H193 H 0.0122 0.8501 -0.0283 0.092(10) Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S 0.0151(4) 0.0155(4) 0.0207(4) -0.0003(3) 0.0003(3) -0.0020(3)
O1 0.0144(12) 0.0300(13) 0.0276(13) -0.0032(10) 0.0008(10) -0.0061(10)
O2 0.0286(13) 0.0140(12) 0.0238(12) 0.0004(9) 0.0020(10) 0.0032(10)
O3 0.0226(13) 0.0223(12) 0.0237(12) -0.0072(10) 0.0066(10) -0.0061(10)
O4 0.0265(14) 0.0307(14) 0.0292(13) -0.0078(11) 0.0002(11) -0.0110(11)
N 0.0159(14) 0.0138(13) 0.0167(14) 0.0004(11) 0.0011(11) -0.0052(11)
C1 0.0158(17) 0.0165(16) 0.0164(16) -0.0020(13) -0.0059(13) -0.0051(13)
C2 0.0154(17) 0.0166(16) 0.0164(16) 0.0027(13) 0.0009(13) 0.0004(13)
C3 0.0186(17) 0.0193(17) 0.0159(16) 0.0054(13) 0.0002(13) -0.0032(13)
C4 0.0213(18) 0.0178(16) 0.0194(17) 0.0002(13) -0.0013(14) -0.0069(13)
C5 0.0165(17) 0.0132(15) 0.0188(16) -0.0021(13) 0.0029(13) -0.0041(13)
C6 0.0206(18) 0.0188(17) 0.0284(19) -0.0086(14) 0.0022(15) -0.0073(14)
C7 0.032(2) 0.0180(18) 0.038(2) -0.0075(16) 0.0123(17) -0.0099(15)
C8 0.035(2) 0.0138(17) 0.034(2) 0.0039(15) 0.0106(17) 0.0016(15)
C9 0.026(2) 0.0215(18) 0.0296(19) 0.0019(15) 0.0023(16) 0.0005(15)
C10 0.0191(18) 0.0182(17) 0.0237(18) 0.0025(14) 0.0018(14) -0.0045(13)
C11 0.0206(18) 0.0209(18) 0.0159(17) 0.0019(14) -0.0025(14) -0.0052(14)
C12 0.032(2) 0.0228(18) 0.0238(18) -0.0027(15) 0.0093(16) 0.0004(15)
C13 0.0226(18) 0.0149(16) 0.0201(17) -0.0034(13) 0.0010(14) 0.0016(14)
C14 0.0262(19) 0.0257(19) 0.0248(18) -0.0026(15) 0.0030(15) -0.0099(15)
C15 0.025(2) 0.047(2) 0.0221(19) -0.0064(18) -0.0049(15) -0.0039(17)
C16 0.043(2) 0.030(2) 0.0189(18) -0.0044(16) -0.0017(17) 0.0142(18)
C17 0.054(3) 0.0167(18) 0.028(2) 0.0045(15) -0.0038(19) 0.0004(17)
C18 0.034(2) 0.0216(18) 0.0247(19) 0.0003(15) -0.0051(16) -0.0068(15)
C19 0.066(3) 0.047(3) 0.024(2) -0.0036(19) -0.019(2) 0.019(2)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
S O1 1.432(2) . ?
S O2 1.437(2) . ?
S N 1.615(2) . ?
S C13 1.767(3) . ?
O3 C11 1.345(4) . ?
O3 C12 1.448(3) . ?
O4 C11 1.204(4) . ?
N C4 1.481(4) . ?
N C1 1.498(4) . ?
C1 C2 1.518(4) . ?
C1 C5 1.516(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.326(4) . ?
C2 C11 1.480(4) . ?
C3 C4 1.497(4) . ?
C3 H3 0.9500 . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 C6 1.385(4) . ?
C5 C10 1.401(4) . ?
C6 C7 1.396(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C12 H121 0.9800 . ?
C12 H122 0.9800 . ?
C12 H123 0.9800 . ?
C13 C14 1.384(5) . ?
C13 C18 1.389(5) . ?
C14 C15 1.382(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.373(5) . ?
C16 C19 1.515(5) . ?
C17 C18 1.384(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H191 0.9800 . ?
C19 H192 0.9800 . ?
C19 H193 0.9800 . ?

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
O1 S O2 120.34(13) . . ?
O1 S N 107.04(13) . . ?
O2 S N 105.85(13) . . ?
O1 S C13 107.56(15) . . ?
O2 S C13 106.85(14) . . ?
N S C13 108.82(14) . . ?
C11 O3 C12 115.6(3) . . ?
C4 N C1 113.2(2) . . ?
C4 N S 121.0(2) . . ?
C1 N S 123.20(19) . . ?
N C1 C2 99.5(2) . . ?
N C1 C5 114.9(2) . . ?
C2 C1 C5 112.7(2) . . ?
N C1 H1 109.7 . . ?
C2 C1 H1 109.7 . . ?
C5 C1 H1 109.7 . . ?
C3 C2 C11 127.7(3) . . ?
C3 C2 C1 113.2(3) . . ?
C11 C2 C1 119.1(3) . . ?
C2 C3 C4 112.2(3) . . ?
C2 C3 H3 123.9 . . ?
C4 C3 H3 123.9 . . ?
N C4 C3 101.4(2) . . ?
N C4 H41 111.5 . . ?
C3 C4 H41 111.5 . . ?
N C4 H42 111.5 . . ?
C3 C4 H42 111.5 . . ?
H41 C4 H42 109.3 . . ?
C6 C5 C10 119.0(3) . . ?
C6 C5 C1 120.8(3) . . ?
C10 C5 C1 120.2(3) . . ?
C5 C6 C7 120.7(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 120.0(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 119.9(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 120.5(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C5 119.8(3) . . ?
C9 C10 H10 120.1 . . ?
C5 C10 H10 120.1 . . ?
O4 C11 O3 124.6(3) . . ?
O4 C11 C2 123.7(3) . . ?
O3 C11 C2 111.7(3) . . ?
O3 C12 H121 109.5 . . ?
O3 C12 H122 109.5 . . ?
H121 C12 H122 109.5 . . ?
O3 C12 H123 109.5 . . ?
H121 C12 H123 109.5 . . ?
H122 C12 H123 109.5 . . ?
C14 C13 C18 120.1(3) . . ?
C14 C13 S 120.7(3) . . ?
C18 C13 S 119.2(3) . . ?
C13 C14 C15 120.1(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 118.2(3) . . ?
C17 C16 C19 121.7(4) . . ?
C15 C16 C19 120.1(4) . . ?
C16 C17 C18 122.2(3) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C17 C18 C13 118.7(3) . . ?
C17 C18 H18 120.6 . . ?
C13 C18 H18 120.6 . . ?
C16 C19 H191 109.5 . . ?
C16 C19 H192 109.5 . . ?
H191 C19 H192 109.5 . . ?
C16 C19 H193 109.5 . . ?
H191 C19 H193 109.5 . . ?
H192 C19 H193 109.5 . . ?

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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S N C4 -165.7(2) . . . . ?
O2 S N C4 -36.2(2) . . . . ?
C13 S N C4 78.3(2) . . . . ?
O1 S N C1 33.5(2) . . . . ?
O2 S N C1 163.0(2) . . . . ?
C13 S N C1 -82.4(2) . . . . ?
C4 N C1 C2 7.4(3) . . . . ?
S N C1 C2 169.49(19) . . . . ?
C4 N C1 C5 -113.3(3) . . . . ?
S N C1 C5 48.8(3) . . . . ?
N C1 C2 C3 -5.7(3) . . . . ?
C5 C1 C2 C3 116.6(3) . . . . ?
N C1 C2 C11 174.5(2) . . . . ?
C5 C1 C2 C11 -63.3(3) . . . . ?
C11 C2 C3 C4 -178.0(3) . . . . ?
C1 C2 C3 C4 2.1(4) . . . . ?
C1 N C4 C3 -6.4(3) . . . . ?
S N C4 C3 -168.97(19) . . . . ?
C2 C3 C4 N 2.5(3) . . . . ?
N C1 C5 C6 -116.4(3) . . . . ?
C2 C1 C5 C6 130.5(3) . . . . ?
N C1 C5 C10 64.8(4) . . . . ?
C2 C1 C5 C10 -48.3(4) . . . . ?
C10 C5 C6 C7 -1.7(5) . . . . ?
C12 O3 C11 O4 -1.6(4) . . . . ?
C12 O3 C11 C2 177.2(2) . . . . ?
C3 C2 C11 O4 157.5(3) . . . . ?
C1 C2 C11 O4 -22.6(4) . . . . ?
C3 C2 C11 O3 -21.3(4) . . . . ?
C1 C2 C11 O3 158.6(2) . . . . ?
O1 S C13 C14 175.4(2) . . . . ?
O2 S C13 C14 44.9(3) . . . . ?
N S C13 C14 -69.0(3) . . . . ?
O1 S C13 C18 -6.3(3) . . . . ?
O2 S C13 C18 -136.8(3) . . . . ?
N S C13 C18 109.4(3) . . . . ?
C18 C13 C14 C15 -2.2(5) . . . . ?
S C13 C14 C15 176.2(2) . . . . ?
S C13 C18 C17 -177.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.075

#=====================================END