# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2001
# CCDC Number: 207/506

#============================================================================
data_global
#============================================================================
_audit_creation_method               'form.cif (version 2.0)'

# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_data_validation_number      ?

_journal_date_recd_electronic        ?
_journal_date_to_coeditor            ?
_journal_date_from_coeditor          ?
_journal_date_accepted               ?
_journal_date_printers_first         ?
_journal_date_printers_final         ?
_journal_date_proofs_out             ?
_journal_date_proofs_in              ?
_journal_coeditor_name               ?
_journal_coeditor_code               ?
_journal_coeditor_notes
; ?
;
_journal_techeditor_code             ?
_journal_techeditor_notes
; ?
;
_journal_coden_ASTM                  ?
_journal_name_full                   ?
_journal_year                        ?
_journal_volume                      ?
_journal_issue                       ?
_journal_page_first                  ?
_journal_page_last                   ?
_journal_paper_category              ?
_journal_suppl_publ_number           ?
_journal_suppl_publ_pages            ?

#==============================================================================

# SUBMISSION DETAILS

_publ_contact_author_name           'Prof.Fun Hoong Kun'
_publ_contact_author_address          
;
      X-ray Crystallography Unit
      School of Physics                 
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA           
;
_publ_contact_author_email        'hkfun@usm.my'
_publ_contact_author_fax          '6 04 6579150'
_publ_contact_author_phone        '6 04 6577888  Ext. 3690'
_publ_requested_journal           'Acta Crystallographica C'
_publ_requested_category          'FO'
_publ_requested_coeditor_name     'Prof. '
_publ_contact_letter
;
     Date  :   1999

     The Managing Editor
     International Union of Crystallography
     5 Abbey Square
     Chester  CH1 2HU
     England

     Ref: Paper submission to Acta Cryst 'C'.

     Dear Sir,
                Attached is a manuscript with the after-mentioned title
     and authors which I wish to submit for publication in Acta Cryst. C.
                
                The structure factor tables and the figure shall be emailed
     to you after receiving the reference number. The letter of submission,
     the transfer of copyright form and the chemical diagram shall be sent
     in hard copy forms to you subsequently.

                                   Yours Sincerely,

                                    Hoong-Kun Fun
;
#============================================================================
# TITLE AND AUTHOR LIST

_publ_section_title
;
;
loop_
 _publ_author_name
 _publ_author_address
     'S.Shanmuga Sundara Raj'
;     X-ray Crystallography Unit
      School of Physics  
      Universiti Sains Malaysia 
      11800 USM, Penang
      Malaysia
;
     'Hoong-Kun Fun'
;     X-ray Crystallography Unit
      School of Physics  
      Universiti Sains Malaysia 
      11800 USM, Penang
      Malaysia
;     
#============================================================================
# TEXT

_publ_section_abstract
;
;

_publ_section_comment
;
;

_publ_section_acknowledgements
;
The authors would like to thank the Malaysian Government and Universiti 
Sains Malaysia for research grant R&D No. 305/pfizik/622004. SSSR thanks the 
Universiti  Sains Malaysia for a Visiting Post-Doctoral Fellowship.
;

_publ_section_references
;

Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G. & Taylor, R.
(1987). Chem. Soc. Perkin Trans. II, S1-S19.
 
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.

Orpen, A.G., Brammer, L., Allen, F.H., Kennard, O., Watson, D.G. & Taylor, R.
(1989). J. Chem. Soc. Dalton Trans., S1-S83.

Siemens (1996). SMART and SAINT. Area Detector Control and Integration
Software. Siemens Analytical X-Ray Systems, Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1996). SADABS. Program for Empirical  Absorption
Correction of Area Detector Data, University of G\"ottingen, Germany.

Sheldrick, G.M. (1997).  SHELXTL V5.1 Software Reference Manual, 
Bruker AXS, Inc., Madison, Wisconsin, USA.

Spek, A.L. (1990). Acta Cryst. A46, C-34.


;

_publ_section_figure_captions
;
Fig.1. The structure of title compound showing 50% probability displacement
       ellipsoids and the atom-numbering scheme.  
;

_publ_section_exptl_prep
;
;

_publ_section_exptl_refinement
;
The data collection covered over a hemisphere of reciprocal space by a
combination of three sets of exposures; each set had a different \f angle (0,
88 and 180\%) for the crystal and each exposure of 10s covered 0.3\% in \w.
The crystal-to-detector distance was 4 cm and the detector swing angle was
-35\%. Coverage of the unique set is over 99% complete. Crystal decay was 
monitored by repeating fifty initial frames at the end of data collection 
and analysing the duplicate reflections, and was found  to be negligible.

;

#============================================================================

data_compound11
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic: (3R,3'R)-1-Acetyl-2-oxo-3'-methyl-3'-phenylspiro[3H-indole-3,2'-oxetane] 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point:149-150
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C19 H17 N O3' 
_chemical_formula_weight          307.34 
 
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' 
 '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' 
 
_symmetry_cell_setting            Monoclinic 
_symmetry_space_group_name_H-M    'P 21/c' 
 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    8.1254(4) 
_cell_length_b                    25.2801(14) 
_cell_length_c                    8.1544(5) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  110.812(1) 
_cell_angle_gamma                 90.00 
_cell_volume                      1565.71(15) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     3394
_cell_measurement_theta_min       1.61 
_cell_measurement_theta_max       28.42 
 
_exptl_crystal_description        slab 
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.44 
_exptl_crystal_size_mid           0.28 
_exptl_crystal_size_min           0.22 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.304 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              648 
_exptl_absorpt_coefficient_mu     0.088 
_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       293(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
;
Siemens SMART CCD area detector diffractometer
;
_diffrn_measurement_method        '\w scans' 
_diffrn_detector_area_resol_mean  8.33
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             10793 
_diffrn_reflns_av_R_equivalents   0.0799 
_diffrn_reflns_av_sigmaI/netI     0.1052 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -22 
_diffrn_reflns_limit_k_max        33 
_diffrn_reflns_limit_l_min        -10 
_diffrn_reflns_limit_l_max        10 
_diffrn_reflns_theta_min          1.61 
_diffrn_reflns_theta_max          28.38 
_reflns_number_total              3789 
_reflns_number_gt                 1638 
_reflns_threshold_expression      'I > 2\s(I)'

_computing_data_collection        'SMART (Siemens, 1996)' 
_computing_cell_refinement        'SAINT (Siemens, 1996)' 
_computing_data_reduction          SAINT 
_computing_structure_solution     'SHELXTL (Sheldrick, 1997)' 
_computing_structure_refinement    SHELXTL  
_computing_molecular_graphics      SHELXTL 
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)
;
 
_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.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_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^)+(0.1004P)^2^+0.0000P] 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          3789 
_refine_ls_number_parameters      208 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1707 
_refine_ls_R_factor_gt            0.0736 
_refine_ls_wR_factor_ref          0.2071 
_refine_ls_wR_factor_gt           0.1646 
_refine_ls_goodness_of_fit_ref    0.915 
_refine_ls_restrained_S_all       0.915 
_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 
O1 O 0.2401(4) 0.51233(9) 0.5809(3) 0.0839(8) Uani 1 1 d . . . 
O2 O 0.0006(3) 0.57341(9) 0.0799(2) 0.0714(7) Uani 1 1 d . . . 
O3 O -0.1295(3) 0.67804(8) 0.1093(2) 0.0608(6) Uani 1 1 d . . . 
N1 N 0.0679(3) 0.56963(8) 0.3831(3) 0.0428(6) Uani 1 1 d . . . 
C1 C -0.4572(4) 0.61745(13) 0.3575(4) 0.0595(8) Uani 1 1 d . . . 
H1A H -0.3948 0.5859 0.3872 0.071 Uiso 1 1 calc R . . 
C2 C -0.5534(4) 0.63475(15) 0.4553(5) 0.0741(10) Uani 1 1 d . . . 
H2A H -0.5516 0.6156 0.5533 0.089 Uiso 1 1 calc R . . 
C3 C -0.6520(5) 0.67988(18) 0.4098(6) 0.0867(13) Uani 1 1 d . . . 
H3A H -0.7196 0.6911 0.4744 0.104 Uiso 1 1 calc R . . 
C4 C -0.6496(5) 0.70837(16) 0.2674(7) 0.0893(13) Uani 1 1 d . . . 
H4A H -0.7162 0.7391 0.2351 0.107 Uiso 1 1 calc R . . 
C5 C -0.5497(4) 0.69182(13) 0.1724(5) 0.0686(10) Uani 1 1 d . . . 
H5A H -0.5486 0.7119 0.0772 0.082 Uiso 1 1 calc R . . 
C6 C -0.4516(3) 0.64643(11) 0.2146(4) 0.0502(7) Uani 1 1 d . . . 
C7 C -0.3374(4) 0.62610(12) 0.1157(3) 0.0529(8) Uani 1 1 d . . . 
C8 C -0.3007(4) 0.66498(16) -0.0117(4) 0.0780(11) Uani 1 1 d . . . 
H8A H -0.2981 0.6481 -0.1176 0.094 Uiso 1 1 calc R . . 
H8B H -0.3807 0.6949 -0.0409 0.094 Uiso 1 1 calc R . . 
C9 C -0.3954(4) 0.57096(14) 0.0440(4) 0.0741(10) Uani 1 1 d . . . 
H9A H -0.3221 0.5587 -0.0181 0.111 Uiso 1 1 calc R . . 
H9B H -0.5157 0.5721 -0.0345 0.111 Uiso 1 1 calc R . . 
H9C H -0.3851 0.5473 0.1393 0.111 Uiso 1 1 calc R . . 
C10 C -0.1331(3) 0.63562(11) 0.2232(3) 0.0449(7) Uani 1 1 d . . . 
C11 C -0.0160(3) 0.58976(11) 0.2116(3) 0.0464(7) Uani 1 1 d . . . 
C12 C 0.1785(4) 0.52551(12) 0.4285(4) 0.0550(8) Uani 1 1 d . . . 
C13 C 0.2174(5) 0.49673(14) 0.2871(5) 0.0809(11) Uani 1 1 d . . . 
H13A H 0.1563 0.5134 0.1763 0.121 Uiso 1 1 calc R . . 
H13B H 0.1793 0.4607 0.2835 0.121 Uiso 1 1 calc R . . 
H13C H 0.3418 0.4976 0.3105 0.121 Uiso 1 1 calc R . . 
C14 C 0.0380(3) 0.60571(10) 0.5049(3) 0.0400(6) Uani 1 1 d . . . 
C15 C 0.1059(4) 0.60470(13) 0.6865(3) 0.0563(8) Uani 1 1 d . . . 
H15A H 0.1744 0.5766 0.7474 0.068 Uiso 1 1 calc R . . 
C16 C 0.0675(4) 0.64732(14) 0.7740(4) 0.0637(9) Uani 1 1 d . . . 
H16A H 0.1109 0.6476 0.8960 0.076 Uiso 1 1 calc R . . 
C17 C -0.0329(4) 0.68909(14) 0.6855(4) 0.0627(9) Uani 1 1 d . . . 
H17A H -0.0534 0.7175 0.7479 0.075 Uiso 1 1 calc R . . 
C18 C -0.1039(4) 0.68922(12) 0.5038(4) 0.0526(7) Uani 1 1 d . . . 
H18A H -0.1734 0.7172 0.4434 0.063 Uiso 1 1 calc R . . 
C19 C -0.0690(3) 0.64683(10) 0.4148(3) 0.0420(6) 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 
O1 0.123(2) 0.0681(16) 0.0515(14) 0.0152(12) 0.0206(13) 0.0339(14) 
O2 0.1034(17) 0.0766(15) 0.0378(11) -0.0037(11) 0.0294(11) 0.0234(13) 
O3 0.0817(14) 0.0526(13) 0.0489(12) 0.0147(10) 0.0242(11) 0.0024(11) 
N1 0.0546(13) 0.0394(13) 0.0327(11) 0.0005(10) 0.0135(10) 0.0016(11) 
C1 0.0598(18) 0.0545(19) 0.066(2) 0.0008(17) 0.0241(16) -0.0025(15) 
C2 0.072(2) 0.075(3) 0.087(3) -0.017(2) 0.044(2) -0.020(2) 
C3 0.067(2) 0.081(3) 0.124(4) -0.046(3) 0.049(2) -0.022(2) 
C4 0.073(2) 0.055(2) 0.132(4) -0.018(3) 0.027(3) 0.0113(19) 
C5 0.0634(19) 0.053(2) 0.080(2) 0.0016(18) 0.0132(17) 0.0124(16) 
C6 0.0471(15) 0.0424(16) 0.0514(17) -0.0018(14) 0.0058(13) 0.0008(13) 
C7 0.0620(18) 0.0551(18) 0.0349(14) 0.0059(14) 0.0091(13) 0.0076(14) 
C8 0.085(2) 0.092(3) 0.0550(19) 0.029(2) 0.0221(18) 0.019(2) 
C9 0.075(2) 0.081(3) 0.0551(19) -0.0239(19) 0.0088(16) -0.0029(19) 
C10 0.0588(16) 0.0409(15) 0.0354(14) 0.0047(12) 0.0172(12) 0.0006(13) 
C11 0.0572(16) 0.0452(17) 0.0354(15) -0.0009(13) 0.0147(12) -0.0013(13) 
C12 0.0666(19) 0.0433(18) 0.0518(19) 0.0009(15) 0.0170(15) 0.0000(15) 
C13 0.115(3) 0.057(2) 0.074(2) -0.0023(18) 0.038(2) 0.031(2) 
C14 0.0479(14) 0.0410(15) 0.0316(13) -0.0059(12) 0.0148(11) -0.0090(12) 
C15 0.0705(18) 0.061(2) 0.0334(15) 0.0025(14) 0.0133(13) -0.0051(15) 
C16 0.086(2) 0.071(2) 0.0361(16) -0.0173(17) 0.0243(15) -0.0204(19) 
C17 0.078(2) 0.060(2) 0.059(2) -0.0236(17) 0.0347(17) -0.0140(17) 
C18 0.0651(18) 0.0475(17) 0.0490(17) -0.0100(14) 0.0250(14) -0.0039(14) 
C19 0.0483(14) 0.0404(15) 0.0394(14) -0.0018(13) 0.0183(12) -0.0041(13) 
 
_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 
O1 C12 1.210(3) . ? 
O2 C11 1.202(3) . ? 
O3 C10 1.426(3) . ? 
O3 C8 1.429(4) . ? 
N1 C12 1.397(4) . ? 
N1 C11 1.415(3) . ? 
N1 C14 1.432(3) . ? 
C1 C2 1.371(4) . ? 
C1 C6 1.391(4) . ? 
C1 H1A 0.9300 . ? 
C2 C3 1.367(5) . ? 
C2 H2A 0.9300 . ? 
C3 C4 1.372(6) . ? 
C3 H3A 0.9300 . ? 
C4 C5 1.372(5) . ? 
C4 H4A 0.9300 . ? 
C5 C6 1.370(4) . ? 
C5 H5A 0.9300 . ? 
C6 C7 1.519(4) . ? 
C7 C9 1.520(4) . ? 
C7 C8 1.534(4) . ? 
C7 C10 1.596(4) . ? 
C8 H8A 0.9700 . ? 
C8 H8B 0.9700 . ? 
C9 H9A 0.9600 . ? 
C9 H9B 0.9600 . ? 
C9 H9C 0.9600 . ? 
C10 C19 1.488(4) . ? 
C10 C11 1.524(4) . ? 
C12 C13 1.489(4) . ? 
C13 H13A 0.9600 . ? 
C13 H13B 0.9600 . ? 
C13 H13C 0.9600 . ? 
C14 C15 1.385(4) . ? 
C14 C19 1.386(4) . ? 
C15 C16 1.388(4) . ? 
C15 H15A 0.9300 . ? 
C16 C17 1.372(4) . ? 
C16 H16A 0.9300 . ? 
C17 C18 1.386(4) . ? 
C17 H17A 0.9300 . ? 
C18 C19 1.379(4) . ? 
C18 H18A 0.9300 . ? 
 
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 
C10 O3 C8 92.0(2) . . ? 
C12 N1 C11 126.0(2) . . ? 
C12 N1 C14 125.2(2) . . ? 
C11 N1 C14 108.4(2) . . ? 
C2 C1 C6 120.9(3) . . ? 
C2 C1 H1A 119.5 . . ? 
C6 C1 H1A 119.5 . . ? 
C3 C2 C1 120.6(4) . . ? 
C3 C2 H2A 119.7 . . ? 
C1 C2 H2A 119.7 . . ? 
C2 C3 C4 119.0(4) . . ? 
C2 C3 H3A 120.5 . . ? 
C4 C3 H3A 120.5 . . ? 
C5 C4 C3 120.5(4) . . ? 
C5 C4 H4A 119.8 . . ? 
C3 C4 H4A 119.8 . . ? 
C6 C5 C4 121.5(4) . . ? 
C6 C5 H5A 119.3 . . ? 
C4 C5 H5A 119.3 . . ? 
C5 C6 C1 117.5(3) . . ? 
C5 C6 C7 124.1(3) . . ? 
C1 C6 C7 118.3(3) . . ? 
C6 C7 C9 110.5(3) . . ? 
C6 C7 C8 116.4(3) . . ? 
C9 C7 C8 115.8(3) . . ? 
C6 C7 C10 111.7(2) . . ? 
C9 C7 C10 118.0(2) . . ? 
C8 C7 C10 82.0(2) . . ? 
O3 C8 C7 93.2(2) . . ? 
O3 C8 H8A 113.1 . . ? 
C7 C8 H8A 113.1 . . ? 
O3 C8 H8B 113.1 . . ? 
C7 C8 H8B 113.1 . . ? 
H8A C8 H8B 110.5 . . ? 
C7 C9 H9A 109.5 . . ? 
C7 C9 H9B 109.5 . . ? 
H9A C9 H9B 109.5 . . ? 
C7 C9 H9C 109.5 . . ? 
H9A C9 H9C 109.5 . . ? 
H9B C9 H9C 109.5 . . ? 
O3 C10 C19 117.4(2) . . ? 
O3 C10 C11 111.9(2) . . ? 
C19 C10 C11 102.5(2) . . ? 
O3 C10 C7 90.78(19) . . ? 
C19 C10 C7 120.9(2) . . ? 
C11 C10 C7 113.7(2) . . ? 
O2 C11 N1 126.3(3) . . ? 
O2 C11 C10 126.0(2) . . ? 
N1 C11 C10 107.7(2) . . ? 
O1 C12 N1 119.0(3) . . ? 
O1 C12 C13 122.5(3) . . ? 
N1 C12 C13 118.6(3) . . ? 
C12 C13 H13A 109.5 . . ? 
C12 C13 H13B 109.5 . . ? 
H13A C13 H13B 109.5 . . ? 
C12 C13 H13C 109.5 . . ? 
H13A C13 H13C 109.5 . . ? 
H13B C13 H13C 109.5 . . ? 
C15 C14 C19 121.1(3) . . ? 
C15 C14 N1 129.0(3) . . ? 
C19 C14 N1 109.8(2) . . ? 
C14 C15 C16 117.3(3) . . ? 
C14 C15 H15A 121.3 . . ? 
C16 C15 H15A 121.3 . . ? 
C17 C16 C15 121.8(3) . . ? 
C17 C16 H16A 119.1 . . ? 
C15 C16 H16A 119.1 . . ? 
C16 C17 C18 120.6(3) . . ? 
C16 C17 H17A 119.7 . . ? 
C18 C17 H17A 119.7 . . ? 
C19 C18 C17 118.4(3) . . ? 
C19 C18 H18A 120.8 . . ? 
C17 C18 H18A 120.8 . . ? 
C18 C19 C14 120.8(2) . . ? 
C18 C19 C10 129.8(3) . . ? 
C14 C19 C10 109.5(2) . . ? 
 
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 
C6 C1 C2 C3 2.7(5) . . . . ? 
C1 C2 C3 C4 -1.7(5) . . . . ? 
C2 C3 C4 C5 -0.1(6) . . . . ? 
C3 C4 C5 C6 0.8(5) . . . . ? 
C4 C5 C6 C1 0.2(4) . . . . ? 
C4 C5 C6 C7 -179.6(3) . . . . ? 
C2 C1 C6 C5 -1.9(4) . . . . ? 
C2 C1 C6 C7 177.9(3) . . . . ? 
C5 C6 C7 C9 -121.2(3) . . . . ? 
C1 C6 C7 C9 59.0(3) . . . . ? 
C5 C6 C7 C8 13.6(4) . . . . ? 
C1 C6 C7 C8 -166.2(3) . . . . ? 
C5 C6 C7 C10 105.3(3) . . . . ? 
C1 C6 C7 C10 -74.5(3) . . . . ? 
C10 O3 C8 C7 11.2(2) . . . . ? 
C6 C7 C8 O3 100.2(3) . . . . ? 
C9 C7 C8 O3 -127.4(3) . . . . ? 
C10 C7 C8 O3 -10.1(2) . . . . ? 
C8 O3 C10 C19 -136.6(3) . . . . ? 
C8 O3 C10 C11 105.3(3) . . . . ? 
C8 O3 C10 C7 -10.7(2) . . . . ? 
C6 C7 C10 O3 -105.2(2) . . . . ? 
C9 C7 C10 O3 125.1(3) . . . . ? 
C8 C7 C10 O3 10.1(2) . . . . ? 
C6 C7 C10 C19 17.7(3) . . . . ? 
C9 C7 C10 C19 -111.9(3) . . . . ? 
C8 C7 C10 C19 133.1(3) . . . . ? 
C6 C7 C10 C11 140.3(2) . . . . ? 
C9 C7 C10 C11 10.7(4) . . . . ? 
C8 C7 C10 C11 -104.4(3) . . . . ? 
C12 N1 C11 O2 -3.3(5) . . . . ? 
C14 N1 C11 O2 169.8(3) . . . . ? 
C12 N1 C11 C10 176.1(2) . . . . ? 
C14 N1 C11 C10 -10.8(3) . . . . ? 
O3 C10 C11 O2 -39.6(4) . . . . ? 
C19 C10 C11 O2 -166.3(3) . . . . ? 
C7 C10 C11 O2 61.5(4) . . . . ? 
O3 C10 C11 N1 141.0(2) . . . . ? 
C19 C10 C11 N1 14.3(3) . . . . ? 
C7 C10 C11 N1 -117.9(2) . . . . ? 
C11 N1 C12 O1 -179.2(3) . . . . ? 
C14 N1 C12 O1 8.9(4) . . . . ? 
C11 N1 C12 C13 1.4(4) . . . . ? 
C14 N1 C12 C13 -170.6(3) . . . . ? 
C12 N1 C14 C15 -1.2(4) . . . . ? 
C11 N1 C14 C15 -174.3(3) . . . . ? 
C12 N1 C14 C19 175.8(2) . . . . ? 
C11 N1 C14 C19 2.6(3) . . . . ? 
C19 C14 C15 C16 -2.2(4) . . . . ? 
N1 C14 C15 C16 174.5(3) . . . . ? 
C14 C15 C16 C17 -0.3(4) . . . . ? 
C15 C16 C17 C18 1.9(5) . . . . ? 
C16 C17 C18 C19 -0.9(4) . . . . ? 
C17 C18 C19 C14 -1.5(4) . . . . ? 
C17 C18 C19 C10 177.2(3) . . . . ? 
C15 C14 C19 C18 3.1(4) . . . . ? 
N1 C14 C19 C18 -174.1(2) . . . . ? 
C15 C14 C19 C10 -175.8(2) . . . . ? 
N1 C14 C19 C10 7.0(3) . . . . ? 
O3 C10 C19 C18 45.3(4) . . . . ? 
C11 C10 C19 C18 168.4(3) . . . . ? 
C7 C10 C19 C18 -63.9(4) . . . . ? 
O3 C10 C19 C14 -136.0(2) . . . . ? 
C11 C10 C19 C14 -12.9(3) . . . . ? 
C7 C10 C19 C14 114.9(3) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.964 
_diffrn_reflns_theta_full              28.38 
_diffrn_measured_fraction_theta_full   0.964 
_refine_diff_density_max    0.256 
_refine_diff_density_min   -0.254 
_refine_diff_density_rms    0.067 

data_compound13
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic:(3R,3's,4'R)-1-Acetyl-2-oxo-3',4'-diphenylspiro[3H-indole-3,2'-oxetane] 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point:186-187 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C24 H19 N O3' 
_chemical_formula_weight          369.40 
 
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' 
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    'P 21/c' 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    9.9020(4) 
_cell_length_b                    8.9865(3) 
_cell_length_c                    22.1097(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  97.750(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      1949.45(12) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     3451
_cell_measurement_theta_min       1.86 
_cell_measurement_theta_max       28.32 
 
_exptl_crystal_description        slab 
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.34 
_exptl_crystal_size_mid           0.24 
_exptl_crystal_size_min           0.14 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.259 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              776 
_exptl_absorpt_coefficient_mu     0.083 
_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       293(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
;
Siemens SMART CCD area detector diffractometer
;
_diffrn_measurement_method        '\w scans' 
_diffrn_detector_area_resol_mean  8.33
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             13236 
_diffrn_reflns_av_R_equivalents   0.0942 
_diffrn_reflns_av_sigmaI/netI     0.1274 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -11 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -29 
_diffrn_reflns_limit_l_max        17 
_diffrn_reflns_theta_min          1.86 
_diffrn_reflns_theta_max          28.32 
_reflns_number_total              4737 
_reflns_number_gt                 1758 
_reflns_threshold_expression      'I > 2\s(I)' 

_computing_data_collection        'SMART (Siemens, 1996)' 
_computing_cell_refinement        'SAINT (Siemens, 1996)' 
_computing_data_reduction          SAINT 
_computing_structure_solution     'SHELXTL (Sheldrick, 1997)' 
_computing_structure_refinement    SHELXTL  
_computing_molecular_graphics      SHELXTL 
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)
;
 
_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.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_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^)+(0.0684P)^2^+0.0000P] 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      SHELXTL 
_refine_ls_extinction_coef        0.0138(16) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_number_reflns          4737 
_refine_ls_number_parameters      254 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1786 
_refine_ls_R_factor_gt            0.0617 
_refine_ls_wR_factor_ref          0.1747 
_refine_ls_wR_factor_gt           0.1345 
_refine_ls_goodness_of_fit_ref    0.846 
_refine_ls_restrained_S_all       0.846 
_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 
O1 O 0.02022(17) 0.94261(19) 0.22631(8) 0.0617(5) Uani 1 1 d . . . 
O2 O -0.13829(18) 1.0982(2) 0.12297(9) 0.0744(6) Uani 1 1 d . . . 
O3 O -0.1281(2) 0.8302(3) -0.02867(10) 0.1029(8) Uani 1 1 d . . . 
N1 N -0.0623(2) 0.9000(2) 0.06831(9) 0.0524(6) Uani 1 1 d . . . 
C1 C 0.1609(3) 0.9653(3) 0.34574(13) 0.0691(8) Uani 1 1 d . . . 
H1A H 0.1053 0.8839 0.3343 0.083 Uiso 1 1 calc R . . 
C2 C 0.2417(4) 0.9676(4) 0.40239(15) 0.0866(10) Uani 1 1 d . . . 
H2A H 0.2393 0.8874 0.4288 0.104 Uiso 1 1 calc R . . 
C3 C 0.3242(4) 1.0856(5) 0.41957(15) 0.0901(11) Uani 1 1 d . . . 
H3A H 0.3779 1.0858 0.4575 0.108 Uiso 1 1 calc R . . 
C4 C 0.3278(3) 1.2054(4) 0.38053(15) 0.0796(10) Uani 1 1 d . . . 
H4A H 0.3850 1.2858 0.3917 0.096 Uiso 1 1 calc R . . 
C5 C 0.2457(3) 1.2044(3) 0.32486(13) 0.0616(8) Uani 1 1 d . . . 
H5A H 0.2457 1.2864 0.2992 0.074 Uiso 1 1 calc R . . 
C6 C 0.1640(2) 1.0845(3) 0.30660(11) 0.0498(7) Uani 1 1 d . . . 
C7 C 0.0804(2) 1.0865(3) 0.24476(11) 0.0514(7) Uani 1 1 d . . . 
H7A H 0.0087 1.1620 0.2437 0.062 Uiso 1 1 calc R . . 
C8 C 0.1490(2) 1.0960(3) 0.18559(11) 0.0470(6) Uani 1 1 d . . . 
H8A H 0.1132 1.1821 0.1613 0.056 Uiso 1 1 calc R . . 
C9 C 0.3013(2) 1.0893(3) 0.18796(11) 0.0472(6) Uani 1 1 d . . . 
C10 C 0.3842(3) 0.9971(3) 0.22768(12) 0.0583(7) Uani 1 1 d . . . 
H10A H 0.3448 0.9367 0.2546 0.070 Uiso 1 1 calc R . . 
C11 C 0.5228(3) 0.9936(4) 0.22793(15) 0.0773(9) Uani 1 1 d . . . 
H11A H 0.5760 0.9296 0.2543 0.093 Uiso 1 1 calc R . . 
C12 C 0.5829(3) 1.0837(4) 0.18960(18) 0.0876(11) Uani 1 1 d . . . 
H12A H 0.6770 1.0821 0.1903 0.105 Uiso 1 1 calc R . . 
C13 C 0.5042(4) 1.1767(4) 0.15001(15) 0.0821(10) Uani 1 1 d . . . 
H13A H 0.5449 1.2382 0.1239 0.099 Uiso 1 1 calc R . . 
C14 C 0.3637(3) 1.1785(3) 0.14913(12) 0.0622(8) Uani 1 1 d . . . 
H14A H 0.3108 1.2409 0.1220 0.075 Uiso 1 1 calc R . . 
C15 C 0.0598(2) 0.9547(3) 0.16597(11) 0.0489(6) Uani 1 1 d . . . 
C16 C 0.1115(3) 0.8176(3) 0.13973(12) 0.0538(7) Uani 1 1 d . . . 
C17 C 0.2096(3) 0.7192(3) 0.16382(15) 0.0834(9) Uani 1 1 d . . . 
H17A H 0.2548 0.7339 0.2030 0.100 Uiso 1 1 calc R . . 
C18 C 0.2419(4) 0.5972(4) 0.12988(18) 0.1034(12) Uani 1 1 d . . . 
H18A H 0.3105 0.5320 0.1459 0.124 Uiso 1 1 calc R . . 
C19 C 0.1723(4) 0.5733(4) 0.07267(17) 0.0925(11) Uani 1 1 d . . . 
H19A H 0.1942 0.4914 0.0502 0.111 Uiso 1 1 calc R . . 
C20 C 0.0710(3) 0.6682(3) 0.04805(13) 0.0703(8) Uani 1 1 d . . . 
H20A H 0.0237 0.6511 0.0094 0.084 Uiso 1 1 calc R . . 
C21 C 0.0407(3) 0.7900(3) 0.08224(11) 0.0524(7) Uani 1 1 d . . . 
C22 C -0.0610(3) 0.9964(3) 0.11859(12) 0.0521(7) Uani 1 1 d . . . 
C23 C -0.1511(3) 0.9095(4) 0.01298(14) 0.0667(8) Uani 1 1 d . . . 
C24 C -0.2676(3) 1.0160(4) 0.00792(14) 0.0853(10) Uani 1 1 d . . . 
H24A H -0.2674 1.0675 0.0460 0.128 Uiso 0.50 1 calc PR . . 
H24B H -0.3516 0.9624 -0.0016 0.128 Uiso 0.50 1 calc PR . . 
H24C H -0.2588 1.0866 -0.0239 0.128 Uiso 0.50 1 calc PR . . 
H24F H -0.3178 1.0102 -0.0323 0.128 Uiso 0.50 1 calc PR . . 
H24E H -0.2336 1.1153 0.0153 0.128 Uiso 0.50 1 calc PR . . 
H24D H -0.3265 0.9910 0.0375 0.128 Uiso 0.50 1 calc PR . . 
 
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 
O1 0.0827(12) 0.0622(12) 0.0428(11) -0.0109(9) 0.0184(10) -0.0269(10) 
O2 0.0587(11) 0.0872(14) 0.0765(15) -0.0214(12) 0.0064(11) 0.0139(11) 
O3 0.1305(19) 0.121(2) 0.0508(14) -0.0216(14) -0.0121(14) 0.0222(16) 
N1 0.0578(13) 0.0598(14) 0.0397(13) -0.0057(11) 0.0073(11) -0.0055(11) 
C1 0.096(2) 0.0695(19) 0.0446(17) -0.0061(15) 0.0198(17) -0.0081(17) 
C2 0.120(3) 0.094(3) 0.047(2) 0.0064(18) 0.017(2) 0.012(2) 
C3 0.100(3) 0.120(3) 0.047(2) -0.015(2) -0.0025(19) 0.011(2) 
C4 0.085(2) 0.093(3) 0.060(2) -0.025(2) 0.0049(19) -0.0059(19) 
C5 0.0714(18) 0.0633(18) 0.0503(18) -0.0137(14) 0.0087(15) -0.0022(15) 
C6 0.0603(16) 0.0560(16) 0.0364(14) -0.0111(13) 0.0179(13) -0.0001(14) 
C7 0.0543(14) 0.0538(15) 0.0478(16) -0.0104(13) 0.0132(13) -0.0085(13) 
C8 0.0549(15) 0.0503(15) 0.0364(14) -0.0020(12) 0.0089(12) 0.0000(12) 
C9 0.0505(14) 0.0561(15) 0.0370(14) -0.0091(13) 0.0134(12) -0.0061(13) 
C10 0.0576(17) 0.0711(19) 0.0479(17) -0.0044(15) 0.0129(14) 0.0030(15) 
C11 0.0633(19) 0.105(3) 0.064(2) -0.015(2) 0.0134(17) 0.0128(19) 
C12 0.0614(19) 0.120(3) 0.085(3) -0.034(2) 0.022(2) -0.008(2) 
C13 0.086(2) 0.100(3) 0.068(2) -0.017(2) 0.037(2) -0.035(2) 
C14 0.076(2) 0.0676(18) 0.0453(16) -0.0085(14) 0.0166(15) -0.0190(15) 
C15 0.0583(15) 0.0518(15) 0.0380(14) -0.0061(12) 0.0114(13) -0.0046(13) 
C16 0.0642(16) 0.0487(15) 0.0478(17) -0.0035(14) 0.0054(15) 0.0038(14) 
C17 0.109(2) 0.0638(19) 0.070(2) -0.0154(18) -0.0158(19) 0.0135(19) 
C18 0.124(3) 0.073(2) 0.101(3) -0.029(2) -0.027(2) 0.034(2) 
C19 0.119(3) 0.068(2) 0.086(3) -0.028(2) -0.002(2) 0.023(2) 
C20 0.091(2) 0.0657(19) 0.0524(18) -0.0156(16) 0.0038(17) 0.0043(17) 
C21 0.0601(16) 0.0558(16) 0.0423(16) -0.0064(13) 0.0099(14) -0.0052(14) 
C22 0.0489(15) 0.0612(17) 0.0475(17) -0.0055(14) 0.0112(13) -0.0023(14) 
C23 0.0751(19) 0.077(2) 0.0469(18) -0.0012(17) 0.0040(17) -0.0027(17) 
C24 0.090(2) 0.097(3) 0.063(2) 0.0063(19) -0.0100(18) 0.014(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 
O1 C15 1.444(3) . ? 
O1 C7 1.459(3) . ? 
O2 C22 1.205(3) . ? 
O3 C23 1.210(3) . ? 
N1 C22 1.408(3) . ? 
N1 C23 1.410(3) . ? 
N1 C21 1.424(3) . ? 
C1 C6 1.380(4) . ? 
C1 C2 1.393(4) . ? 
C1 H1A 0.9300 . ? 
C2 C3 1.361(5) . ? 
C2 H2A 0.9300 . ? 
C3 C4 1.383(4) . ? 
C3 H3A 0.9300 . ? 
C4 C5 1.381(4) . ? 
C4 H4A 0.9300 . ? 
C5 C6 1.375(3) . ? 
C5 H5A 0.9300 . ? 
C6 C7 1.500(3) . ? 
C7 C8 1.555(3) . ? 
C7 H7A 0.9800 . ? 
C8 C9 1.503(3) . ? 
C8 C15 1.574(3) . ? 
C8 H8A 0.9800 . ? 
C9 C14 1.380(3) . ? 
C9 C10 1.391(3) . ? 
C10 C11 1.373(3) . ? 
C10 H10A 0.9300 . ? 
C11 C12 1.365(4) . ? 
C11 H11A 0.9300 . ? 
C12 C13 1.374(4) . ? 
C12 H12A 0.9300 . ? 
C13 C14 1.389(4) . ? 
C13 H13A 0.9300 . ? 
C14 H14A 0.9300 . ? 
C15 C16 1.482(3) . ? 
C15 C22 1.527(3) . ? 
C16 C17 1.367(4) . ? 
C16 C21 1.388(3) . ? 
C17 C18 1.390(4) . ? 
C17 H17A 0.9300 . ? 
C18 C19 1.373(4) . ? 
C18 H18A 0.9300 . ? 
C19 C20 1.372(4) . ? 
C19 H19A 0.9300 . ? 
C20 C21 1.386(4) . ? 
C20 H20A 0.9300 . ? 
C23 C24 1.491(4) . ? 
C24 H24A 0.9600 . ? 
C24 H24B 0.9600 . ? 
C24 H24C 0.9600 . ? 
C24 H24F 0.9600 . ? 
C24 H24E 0.9600 . ? 
C24 H24D 0.9600 . ? 
 
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 
C15 O1 C7 92.29(16) . . ? 
C22 N1 C23 125.9(2) . . ? 
C22 N1 C21 109.0(2) . . ? 
C23 N1 C21 125.1(2) . . ? 
C6 C1 C2 119.6(3) . . ? 
C6 C1 H1A 120.2 . . ? 
C2 C1 H1A 120.2 . . ? 
C3 C2 C1 120.8(3) . . ? 
C3 C2 H2A 119.6 . . ? 
C1 C2 H2A 119.6 . . ? 
C2 C3 C4 119.8(3) . . ? 
C2 C3 H3A 120.1 . . ? 
C4 C3 H3A 120.1 . . ? 
C5 C4 C3 119.3(3) . . ? 
C5 C4 H4A 120.4 . . ? 
C3 C4 H4A 120.4 . . ? 
C6 C5 C4 121.3(3) . . ? 
C6 C5 H5A 119.3 . . ? 
C4 C5 H5A 119.3 . . ? 
C5 C6 C1 119.1(3) . . ? 
C5 C6 C7 119.3(2) . . ? 
C1 C6 C7 121.7(2) . . ? 
O1 C7 C6 113.5(2) . . ? 
O1 C7 C8 91.26(17) . . ? 
C6 C7 C8 121.2(2) . . ? 
O1 C7 H7A 109.8 . . ? 
C6 C7 H7A 109.8 . . ? 
C8 C7 H7A 109.8 . . ? 
C9 C8 C7 121.2(2) . . ? 
C9 C8 C15 119.99(19) . . ? 
C7 C8 C15 83.98(16) . . ? 
C9 C8 H8A 109.7 . . ? 
C7 C8 H8A 109.7 . . ? 
C15 C8 H8A 109.7 . . ? 
C14 C9 C10 117.6(2) . . ? 
C14 C9 C8 119.1(2) . . ? 
C10 C9 C8 123.3(2) . . ? 
C11 C10 C9 121.4(3) . . ? 
C11 C10 H10A 119.3 . . ? 
C9 C10 H10A 119.3 . . ? 
C12 C11 C10 120.2(3) . . ? 
C12 C11 H11A 119.9 . . ? 
C10 C11 H11A 119.9 . . ? 
C11 C12 C13 120.0(3) . . ? 
C11 C12 H12A 120.0 . . ? 
C13 C12 H12A 120.0 . . ? 
C12 C13 C14 119.8(3) . . ? 
C12 C13 H13A 120.1 . . ? 
C14 C13 H13A 120.1 . . ? 
C9 C14 C13 121.1(3) . . ? 
C9 C14 H14A 119.5 . . ? 
C13 C14 H14A 119.5 . . ? 
O1 C15 C16 116.8(2) . . ? 
O1 C15 C22 111.52(19) . . ? 
C16 C15 C22 102.4(2) . . ? 
O1 C15 C8 91.05(17) . . ? 
C16 C15 C8 124.6(2) . . ? 
C22 C15 C8 110.5(2) . . ? 
C17 C16 C21 119.0(3) . . ? 
C17 C16 C15 130.5(3) . . ? 
C21 C16 C15 110.4(2) . . ? 
C16 C17 C18 120.2(3) . . ? 
C16 C17 H17A 119.9 . . ? 
C18 C17 H17A 119.9 . . ? 
C19 C18 C17 119.8(3) . . ? 
C19 C18 H18A 120.1 . . ? 
C17 C18 H18A 120.1 . . ? 
C20 C19 C18 121.2(3) . . ? 
C20 C19 H19A 119.4 . . ? 
C18 C19 H19A 119.4 . . ? 
C19 C20 C21 118.3(3) . . ? 
C19 C20 H20A 120.8 . . ? 
C21 C20 H20A 120.8 . . ? 
C20 C21 C16 121.4(3) . . ? 
C20 C21 N1 129.2(3) . . ? 
C16 C21 N1 109.4(2) . . ? 
O2 C22 N1 126.3(3) . . ? 
O2 C22 C15 125.4(2) . . ? 
N1 C22 C15 108.3(2) . . ? 
O3 C23 N1 117.7(3) . . ? 
O3 C23 C24 123.0(3) . . ? 
N1 C23 C24 119.3(3) . . ? 
C23 C24 H24A 109.5 . . ? 
C23 C24 H24B 109.5 . . ? 
H24A C24 H24B 109.5 . . ? 
C23 C24 H24C 109.5 . . ? 
H24A C24 H24C 109.5 . . ? 
H24B C24 H24C 109.5 . . ? 
C23 C24 H24F 109.5 . . ? 
H24A C24 H24F 141.1 . . ? 
H24B C24 H24F 56.3 . . ? 
H24C C24 H24F 56.3 . . ? 
C23 C24 H24E 109.5 . . ? 
H24A C24 H24E 56.3 . . ? 
H24B C24 H24E 141.1 . . ? 
H24C C24 H24E 56.3 . . ? 
H24F C24 H24E 109.5 . . ? 
C23 C24 H24D 109.5 . . ? 
H24A C24 H24D 56.3 . . ? 
H24B C24 H24D 56.3 . . ? 
H24C C24 H24D 141.1 . . ? 
H24F C24 H24D 109.5 . . ? 
H24E C24 H24D 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 
C6 C1 C2 C3 -0.3(5) . . . . ? 
C1 C2 C3 C4 0.2(5) . . . . ? 
C2 C3 C4 C5 1.0(5) . . . . ? 
C3 C4 C5 C6 -2.3(4) . . . . ? 
C4 C5 C6 C1 2.2(4) . . . . ? 
C4 C5 C6 C7 -177.8(2) . . . . ? 
C2 C1 C6 C5 -0.9(4) . . . . ? 
C2 C1 C6 C7 179.1(2) . . . . ? 
C15 O1 C7 C6 -134.5(2) . . . . ? 
C15 O1 C7 C8 -9.41(19) . . . . ? 
C5 C6 C7 O1 168.5(2) . . . . ? 
C1 C6 C7 O1 -11.5(3) . . . . ? 
C5 C6 C7 C8 61.5(3) . . . . ? 
C1 C6 C7 C8 -118.5(3) . . . . ? 
O1 C7 C8 C9 -112.9(2) . . . . ? 
C6 C7 C8 C9 5.7(4) . . . . ? 
O1 C7 C8 C15 8.67(17) . . . . ? 
C6 C7 C8 C15 127.3(2) . . . . ? 
C7 C8 C9 C14 -141.6(2) . . . . ? 
C15 C8 C9 C14 116.4(3) . . . . ? 
C7 C8 C9 C10 38.2(3) . . . . ? 
C15 C8 C9 C10 -63.8(3) . . . . ? 
C14 C9 C10 C11 -0.7(4) . . . . ? 
C8 C9 C10 C11 179.4(2) . . . . ? 
C9 C10 C11 C12 1.3(4) . . . . ? 
C10 C11 C12 C13 -0.9(5) . . . . ? 
C11 C12 C13 C14 -0.1(5) . . . . ? 
C10 C9 C14 C13 -0.3(4) . . . . ? 
C8 C9 C14 C13 179.6(2) . . . . ? 
C12 C13 C14 C9 0.7(4) . . . . ? 
C7 O1 C15 C16 139.5(2) . . . . ? 
C7 O1 C15 C22 -103.2(2) . . . . ? 
C7 O1 C15 C8 9.30(18) . . . . ? 
C9 C8 C15 O1 114.0(2) . . . . ? 
C7 C8 C15 O1 -8.76(18) . . . . ? 
C9 C8 C15 C16 -10.1(4) . . . . ? 
C7 C8 C15 C16 -132.8(2) . . . . ? 
C9 C8 C15 C22 -132.5(2) . . . . ? 
C7 C8 C15 C22 104.7(2) . . . . ? 
O1 C15 C16 C17 -50.3(4) . . . . ? 
C22 C15 C16 C17 -172.4(3) . . . . ? 
C8 C15 C16 C17 61.6(4) . . . . ? 
O1 C15 C16 C21 127.4(2) . . . . ? 
C22 C15 C16 C21 5.3(3) . . . . ? 
C8 C15 C16 C21 -120.7(3) . . . . ? 
C21 C16 C17 C18 3.0(5) . . . . ? 
C15 C16 C17 C18 -179.5(3) . . . . ? 
C16 C17 C18 C19 -1.9(6) . . . . ? 
C17 C18 C19 C20 0.2(6) . . . . ? 
C18 C19 C20 C21 0.4(5) . . . . ? 
C19 C20 C21 C16 0.8(4) . . . . ? 
C19 C20 C21 N1 -177.1(3) . . . . ? 
C17 C16 C21 C20 -2.4(4) . . . . ? 
C15 C16 C21 C20 179.6(2) . . . . ? 
C17 C16 C21 N1 175.8(2) . . . . ? 
C15 C16 C21 N1 -2.2(3) . . . . ? 
C22 N1 C21 C20 175.8(3) . . . . ? 
C23 N1 C21 C20 -3.9(4) . . . . ? 
C22 N1 C21 C16 -2.3(3) . . . . ? 
C23 N1 C21 C16 178.0(2) . . . . ? 
C23 N1 C22 O2 2.8(4) . . . . ? 
C21 N1 C22 O2 -176.9(2) . . . . ? 
C23 N1 C22 C15 -174.6(2) . . . . ? 
C21 N1 C22 C15 5.7(3) . . . . ? 
O1 C15 C22 O2 50.4(3) . . . . ? 
C16 C15 C22 O2 176.0(3) . . . . ? 
C8 C15 C22 O2 -49.3(3) . . . . ? 
O1 C15 C22 N1 -132.2(2) . . . . ? 
C16 C15 C22 N1 -6.6(2) . . . . ? 
C8 C15 C22 N1 128.1(2) . . . . ? 
C22 N1 C23 O3 170.8(3) . . . . ? 
C21 N1 C23 O3 -9.5(4) . . . . ? 
C22 N1 C23 C24 -8.9(4) . . . . ? 
C21 N1 C23 C24 170.8(2) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.979 
_diffrn_reflns_theta_full              28.32 
_diffrn_measured_fraction_theta_full   0.978 
_refine_diff_density_max    0.200 
_refine_diff_density_min   -0.227 
_refine_diff_density_rms    0.052 
 
data_compound19 
 
_audit_creation_method            SHELXL 
_chemical_name_systematic:(3s,2'aR,8'aR)-1-Acetyl-2a',3',8',8a'-tetrahydro-3',8'-(diphenylmethylenemethano)spiro[indoline-3,2'-2'H-oxoto[3,2-b]naphthalen]-2-one 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C34 H25 N O3' 
_chemical_formula_weight          495.55 
_chemical_melting_point:232          
_chemical_compound_source         ? 
 
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' 
 
_symmetry_cell_setting            orthorhombic
_symmetry_space_group_name_H-M    Pbca
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
 '-x, -y, -z' 
 'x-1/2, y, -z-1/2' 
 'x, -y-1/2, z-1/2' 
 '-x-1/2, y-1/2, z' 
 
_cell_length_a                    9.0605(2) 
_cell_length_b                    17.87250(10) 
_cell_length_c                    31.4066(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      5085.8(2) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.54
_exptl_crystal_size_mid           0.34
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.294 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              2080 
_exptl_absorpt_coefficient_mu     0.082 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(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        ? 
_diffrn_measurement_method        ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             30518 
_diffrn_reflns_av_R_equivalents   0.0665 
_diffrn_reflns_av_sigmaI/netI     0.0491 
_diffrn_reflns_limit_h_min        -13 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        -27 
_diffrn_reflns_limit_k_max        26 
_diffrn_reflns_limit_l_min        -19 
_diffrn_reflns_limit_l_max        48 
_diffrn_reflns_theta_min          2.59 
_diffrn_reflns_theta_max          27.50 
_reflns_number_total              5829 
_reflns_number_observed           3270 
_reflns_observed_criterion        >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 8 with very negative F^2^ 
 or flagged by the user for potential systematic errors.  Weighted R-factors 
 wR and all goodnesses 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 observed criterion 
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme 
 'calc w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+1.9794P] 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     ? 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          5821 
_refine_ls_number_parameters      343 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1305 
_refine_ls_R_factor_obs           0.0669 
_refine_ls_wR_factor_all          0.1597 
_refine_ls_wR_factor_obs          0.1311 
_refine_ls_goodness_of_fit_all    1.071 
_refine_ls_goodness_of_fit_obs    1.202 
_refine_ls_restrained_S_all       1.075 
_refine_ls_restrained_S_obs       1.202 
_refine_ls_shift/esd_max          0.000 
_refine_ls_shift/esd_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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
N1 N 0.0839(2) 0.34937(11) -0.00148(7) 0.0563(5) Uani 1 d . . 
O1 O 0.3356(2) 0.32337(13) 0.00267(7) 0.0861(6) Uani 1 d . . 
O2 O -0.0775(3) 0.31966(13) -0.05402(8) 0.0972(7) Uani 1 d . . 
O3 O 0.3404(2) 0.46135(9) 0.05025(5) 0.0591(5) Uani 1 d . . 
C1 C 0.3519(3) 0.61833(13) 0.14388(8) 0.0518(6) Uani 1 d . . 
C2 C 0.4013(3) 0.6632(2) 0.17661(10) 0.0740(8) Uani 1 d . . 
H2A H 0.3817(3) 0.6501(2) 0.20470(10) 0.089 Uiso 1 calc R . 
C3 C 0.4803(4) 0.7280(2) 0.16772(12) 0.0896(10) Uani 1 d . . 
H3A H 0.5136(4) 0.7578(2) 0.19000(12) 0.107 Uiso 1 calc R . 
C4 C 0.5096(3) 0.7483(2) 0.12699(12) 0.0810(9) Uani 1 d . . 
H4A H 0.5629(3) 0.7917(2) 0.12143(12) 0.097 Uiso 1 calc R . 
C5 C 0.4607(3) 0.7049(2) 0.09421(11) 0.0758(8) Uani 1 d . . 
H5A H 0.4802(3) 0.7188(2) 0.06623(11) 0.091 Uiso 1 calc R . 
C6 C 0.3820(3) 0.6403(2) 0.10258(9) 0.0655(7) Uani 1 d . . 
H6A H 0.3488(3) 0.6111(2) 0.08003(9) 0.079 Uiso 1 calc R . 
C7 C 0.2680(3) 0.54742(13) 0.15247(8) 0.0507(6) Uani 1 d . . 
C8 C 0.1244(3) 0.55381(14) 0.17522(8) 0.0522(6) Uani 1 d . . 
C9 C 0.0266(3) 0.61067(15) 0.16442(9) 0.0639(7) Uani 1 d . . 
H9A H 0.0547(3) 0.64678(15) 0.14469(9) 0.077 Uiso 1 calc R . 
C10 C -0.1129(3) 0.6140(2) 0.18289(10) 0.0757(9) Uani 1 d . . 
H10A H -0.1785(3) 0.6514(2) 0.17484(10) 0.091 Uiso 1 calc R . 
C11 C -0.1540(4) 0.5623(2) 0.21291(11) 0.0822(9) Uani 1 d . . 
H11A H -0.2476(4) 0.5644(2) 0.22502(11) 0.099 Uiso 1 calc R . 
C12 C -0.0562(4) 0.5074(2) 0.22505(10) 0.0774(9) Uani 1 d . . 
H12A H -0.0828(4) 0.4732(2) 0.24604(10) 0.093 Uiso 1 calc R . 
C13 C 0.0815(3) 0.50265(15) 0.20621(8) 0.0619(7) Uani 1 d . . 
H13A H 0.1461(3) 0.46484(15) 0.21435(8) 0.074 Uiso 1 calc R . 
C14 C 0.3207(3) 0.48263(13) 0.13792(8) 0.0502(6) Uani 1 d . . 
C15 C 0.4735(3) 0.46573(14) 0.11958(8) 0.0544(6) Uani 1 d . . 
H15A H 0.5389(3) 0.50863(14) 0.11497(8) 0.065 Uiso 1 calc R . 
C16 C 0.5221(3) 0.40904(14) 0.15252(8) 0.0584(7) Uani 1 d . . 
C17 C 0.6575(3) 0.3933(2) 0.16973(10) 0.0722(8) Uani 1 d . . 
H17A H 0.7415(3) 0.4190(2) 0.16102(10) 0.087 Uiso 1 calc R . 
C18 C 0.6657(4) 0.3379(2) 0.20043(11) 0.0900(10) Uani 1 d . . 
H18A H 0.7563(4) 0.3269(2) 0.21283(11) 0.108 Uiso 1 calc R . 
C19 C 0.5423(5) 0.2986(2) 0.21303(10) 0.0881(10) Uani 1 d . . 
H19A H 0.5510(5) 0.2620(2) 0.23390(10) 0.106 Uiso 1 calc R . 
C20 C 0.4041(4) 0.3131(2) 0.19489(9) 0.0719(8) Uani 1 d . . 
H20A H 0.3213(4) 0.2856(2) 0.20264(9) 0.086 Uiso 1 calc R . 
C21 C 0.3951(3) 0.36948(14) 0.16523(8) 0.0567(6) Uani 1 d . . 
C22 C 0.2668(3) 0.40121(13) 0.13950(7) 0.0523(6) Uani 1 d . . 
H22A H 0.1673(3) 0.39264(13) 0.15074(7) 0.063 Uiso 1 calc R . 
C23 C 0.2992(2) 0.37165(14) 0.09380(8) 0.0516(6) Uani 1 d . . 
H23A H 0.3151(2) 0.31751(14) 0.09191(8) 0.062 Uiso 1 calc R . 
C24 C 0.4327(3) 0.41975(14) 0.08037(8) 0.0553(6) Uani 1 d . . 
H24A H 0.5145(3) 0.39192(14) 0.06750(8) 0.066 Uiso 1 calc R . 
C25 C 0.2220(3) 0.40672(14) 0.05460(8) 0.0539(6) Uani 1 d . . 
C26 C 0.0672(3) 0.43458(13) 0.05375(8) 0.0519(6) Uani 1 d . . 
C27 C -0.0012(3) 0.4879(2) 0.07849(9) 0.0634(7) Uani 1 d . . 
H27A H 0.0506(3) 0.5118(2) 0.10013(9) 0.076 Uiso 1 calc R . 
C28 C -0.1480(3) 0.5057(2) 0.07094(9) 0.0667(7) Uani 1 d . . 
H28A H -0.1952(3) 0.5411(2) 0.08787(9) 0.080 Uiso 1 calc R . 
C29 C -0.2232(3) 0.4714(2) 0.03859(9) 0.0663(7) Uani 1 d . . 
H29A H -0.3209(3) 0.4846(2) 0.03348(9) 0.080 Uiso 1 calc R . 
C30 C -0.1572(3) 0.4173(2) 0.01324(9) 0.0630(7) Uani 1 d . . 
H30A H -0.2097(3) 0.3934(2) -0.00830(9) 0.076 Uiso 1 calc R . 
C31 C -0.0105(3) 0.39997(13) 0.02106(8) 0.0530(6) Uani 1 d . . 
C32 C 0.2266(3) 0.35373(15) 0.01585(8) 0.0593(7) Uani 1 d . . 
C33 C 0.0438(3) 0.3115(2) -0.03936(10) 0.0676(7) Uani 1 d . . 
C34 C 0.1552(4) 0.2620(2) -0.05966(11) 0.0962(11) Uani 1 d . . 
H34A H 0.2446(4) 0.2629(2) -0.04328(11) 0.144 Uiso 1 calc R . 
H34B H 0.1751(4) 0.2794(2) -0.08802(11) 0.144 Uiso 1 calc R . 
H34C H 0.1178(4) 0.2118(2) -0.06082(11) 0.144 Uiso 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 
N1 0.0575(13) 0.0567(12) 0.0546(13) 0.0044(10) -0.0051(10) -0.0046(10) 
O1 0.0667(13) 0.117(2) 0.0741(13) -0.0267(12) -0.0038(11) 0.0193(12) 
O2 0.092(2) 0.100(2) 0.100(2) -0.0229(13) -0.0361(14) 0.0057(14) 
O3 0.0514(10) 0.0650(11) 0.0609(10) 0.0098(9) 0.0012(8) -0.0049(8) 
C1 0.0435(13) 0.0488(13) 0.063(2) -0.0022(12) 0.0010(12) -0.0029(11) 
C2 0.077(2) 0.074(2) 0.071(2) -0.016(2) 0.016(2) -0.025(2) 
C3 0.092(2) 0.086(2) 0.091(2) -0.033(2) 0.026(2) -0.036(2) 
C4 0.068(2) 0.057(2) 0.119(3) -0.005(2) 0.023(2) -0.014(2) 
C5 0.074(2) 0.070(2) 0.084(2) 0.019(2) 0.003(2) -0.009(2) 
C6 0.064(2) 0.067(2) 0.065(2) 0.0086(14) -0.0097(14) -0.0117(14) 
C7 0.0453(13) 0.0528(14) 0.0539(14) 0.0023(12) -0.0008(11) -0.0040(11) 
C8 0.0512(14) 0.0547(14) 0.0508(14) -0.0099(12) 0.0010(11) -0.0087(12) 
C9 0.059(2) 0.060(2) 0.072(2) -0.0077(14) 0.0125(14) -0.0021(13) 
C10 0.060(2) 0.076(2) 0.091(2) -0.020(2) 0.010(2) 0.003(2) 
C11 0.065(2) 0.097(2) 0.085(2) -0.019(2) 0.024(2) -0.014(2) 
C12 0.081(2) 0.088(2) 0.063(2) -0.003(2) 0.018(2) -0.023(2) 
C13 0.064(2) 0.069(2) 0.0526(15) -0.0051(13) 0.0018(13) -0.0119(14) 
C14 0.0431(13) 0.0518(14) 0.0557(14) 0.0013(12) -0.0010(11) -0.0041(11) 
C15 0.0431(13) 0.0529(14) 0.067(2) -0.0011(12) 0.0010(12) -0.0030(11) 
C16 0.056(2) 0.0589(15) 0.061(2) -0.0128(13) -0.0067(13) 0.0053(13) 
C17 0.063(2) 0.082(2) 0.072(2) -0.017(2) -0.0141(15) 0.015(2) 
C18 0.085(2) 0.106(3) 0.079(2) -0.012(2) -0.021(2) 0.036(2) 
C19 0.121(3) 0.083(2) 0.060(2) 0.004(2) -0.015(2) 0.034(2) 
C20 0.099(2) 0.060(2) 0.057(2) -0.0014(14) -0.002(2) 0.008(2) 
C21 0.065(2) 0.0538(14) 0.0513(14) -0.0069(12) -0.0056(13) 0.0041(13) 
C22 0.0520(14) 0.0504(13) 0.0544(14) 0.0000(11) 0.0018(12) -0.0043(11) 
C23 0.0481(13) 0.0520(13) 0.0547(14) 0.0011(11) -0.0040(11) -0.0009(11) 
C24 0.0441(13) 0.0606(15) 0.061(2) 0.0023(13) -0.0004(12) 0.0010(12) 
C25 0.0481(14) 0.0593(14) 0.0542(14) 0.0034(12) -0.0014(11) -0.0043(12) 
C26 0.0485(14) 0.0563(14) 0.0509(14) 0.0078(12) -0.0004(11) -0.0038(12) 
C27 0.056(2) 0.075(2) 0.059(2) 0.0005(14) -0.0003(13) 0.0001(14) 
C28 0.056(2) 0.080(2) 0.065(2) 0.007(2) 0.0116(14) 0.0070(14) 
C29 0.0453(15) 0.086(2) 0.067(2) 0.021(2) 0.0027(14) -0.0026(14) 
C30 0.053(2) 0.076(2) 0.060(2) 0.0115(14) -0.0033(13) -0.0113(14) 
C31 0.0531(15) 0.0531(14) 0.0527(14) 0.0119(12) 0.0025(12) -0.0061(12) 
C32 0.057(2) 0.066(2) 0.055(2) 0.0028(13) 0.0001(13) 0.0028(14) 
C33 0.075(2) 0.060(2) 0.068(2) -0.0016(14) -0.009(2) -0.0092(15) 
C34 0.096(2) 0.093(2) 0.100(3) -0.036(2) -0.010(2) -0.005(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 
N1 C32 1.405(3) . ? 
N1 C33 1.416(3) . ? 
N1 C31 1.432(3) . ? 
O1 C32 1.200(3) . ? 
O2 C33 1.201(3) . ? 
O3 C25 1.457(3) . ? 
O3 C24 1.465(3) . ? 
C1 C2 1.379(4) . ? 
C1 C6 1.383(4) . ? 
C1 C7 1.502(3) . ? 
C2 C3 1.390(4) . ? 
C3 C4 1.356(5) . ? 
C4 C5 1.363(4) . ? 
C5 C6 1.382(4) . ? 
C7 C14 1.333(3) . ? 
C7 C8 1.489(3) . ? 
C8 C9 1.390(3) . ? 
C8 C13 1.391(3) . ? 
C9 C10 1.392(4) . ? 
C10 C11 1.371(4) . ? 
C11 C12 1.377(4) . ? 
C12 C13 1.383(4) . ? 
C14 C15 1.529(3) . ? 
C14 C22 1.536(3) . ? 
C15 C16 1.514(4) . ? 
C15 C24 1.526(3) . ? 
C16 C17 1.371(4) . ? 
C16 C21 1.408(4) . ? 
C17 C18 1.384(4) . ? 
C18 C19 1.378(5) . ? 
C19 C20 1.400(4) . ? 
C20 C21 1.374(4) . ? 
C21 C22 1.525(3) . ? 
C22 C23 1.557(3) . ? 
C23 C24 1.543(3) . ? 
C23 C25 1.549(3) . ? 
C25 C26 1.488(3) . ? 
C25 C32 1.543(4) . ? 
C26 C27 1.377(3) . ? 
C26 C31 1.390(3) . ? 
C27 C28 1.388(4) . ? 
C28 C29 1.369(4) . ? 
C29 C30 1.388(4) . ? 
C30 C31 1.387(3) . ? 
C33 C34 1.485(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 
C32 N1 C33 126.0(2) . . ? 
C32 N1 C31 108.8(2) . . ? 
C33 N1 C31 124.3(2) . . ? 
C25 O3 C24 91.1(2) . . ? 
C2 C1 C6 118.0(2) . . ? 
C2 C1 C7 121.4(2) . . ? 
C6 C1 C7 120.6(2) . . ? 
C1 C2 C3 120.2(3) . . ? 
C4 C3 C2 120.9(3) . . ? 
C3 C4 C5 119.8(3) . . ? 
C4 C5 C6 119.9(3) . . ? 
C5 C6 C1 121.2(3) . . ? 
C14 C7 C8 123.0(2) . . ? 
C14 C7 C1 119.3(2) . . ? 
C8 C7 C1 117.6(2) . . ? 
C9 C8 C13 118.3(2) . . ? 
C9 C8 C7 119.7(2) . . ? 
C13 C8 C7 122.0(2) . . ? 
C8 C9 C10 120.5(3) . . ? 
C11 C10 C9 120.3(3) . . ? 
C10 C11 C12 119.7(3) . . ? 
C11 C12 C13 120.4(3) . . ? 
C12 C13 C8 120.7(3) . . ? 
C7 C14 C15 128.7(2) . . ? 
C7 C14 C22 134.2(2) . . ? 
C15 C14 C22 96.5(2) . . ? 
C16 C15 C24 105.2(2) . . ? 
C16 C15 C14 97.9(2) . . ? 
C24 C15 C14 101.0(2) . . ? 
C17 C16 C21 121.1(3) . . ? 
C17 C16 C15 131.9(3) . . ? 
C21 C16 C15 107.0(2) . . ? 
C16 C17 C18 118.0(3) . . ? 
C19 C18 C17 121.4(3) . . ? 
C18 C19 C20 121.0(3) . . ? 
C21 C20 C19 117.7(3) . . ? 
C20 C21 C16 120.8(3) . . ? 
C20 C21 C22 132.6(3) . . ? 
C16 C21 C22 106.6(2) . . ? 
C21 C22 C14 97.3(2) . . ? 
C21 C22 C23 102.6(2) . . ? 
C14 C22 C23 103.4(2) . . ? 
C24 C23 C25 84.9(2) . . ? 
C24 C23 C22 102.2(2) . . ? 
C25 C23 C22 120.7(2) . . ? 
O3 C24 C15 112.7(2) . . ? 
O3 C24 C23 90.7(2) . . ? 
C15 C24 C23 105.6(2) . . ? 
O3 C25 C26 117.9(2) . . ? 
O3 C25 C32 108.5(2) . . ? 
C26 C25 C32 102.5(2) . . ? 
O3 C25 C23 90.7(2) . . ? 
C26 C25 C23 125.1(2) . . ? 
C32 C25 C23 111.5(2) . . ? 
C27 C26 C31 119.8(2) . . ? 
C27 C26 C25 130.2(2) . . ? 
C31 C26 C25 110.0(2) . . ? 
C26 C27 C28 119.6(3) . . ? 
C29 C28 C27 120.1(3) . . ? 
C28 C29 C30 121.6(3) . . ? 
C31 C30 C29 117.8(3) . . ? 
C30 C31 C26 121.1(2) . . ? 
C30 C31 N1 128.7(2) . . ? 
C26 C31 N1 110.1(2) . . ? 
O1 C32 N1 126.7(2) . . ? 
O1 C32 C25 124.9(2) . . ? 
N1 C32 C25 108.3(2) . . ? 
O2 C33 N1 119.9(3) . . ? 
O2 C33 C34 122.0(3) . . ? 
N1 C33 C34 118.1(3) . . ? 
 
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 
 C6 C1 C2 C3 -0.7(4) . . . . ? 
 C7 C1 C2 C3 179.1(3) . . . . ? 
 C1 C2 C3 C4 0.3(5) . . . . ? 
 C2 C3 C4 C5 0.2(5) . . . . ? 
 C3 C4 C5 C6 -0.3(5) . . . . ? 
 C4 C5 C6 C1 -0.2(4) . . . . ? 
 C2 C1 C6 C5 0.7(4) . . . . ? 
 C7 C1 C6 C5 -179.2(2) . . . . ? 
 C2 C1 C7 C14 -121.5(3) . . . . ? 
 C6 C1 C7 C14 58.3(3) . . . . ? 
 C2 C1 C7 C8 61.5(3) . . . . ? 
 C6 C1 C7 C8 -118.6(3) . . . . ? 
 C14 C7 C8 C9 -134.4(3) . . . . ? 
 C1 C7 C8 C9 42.4(3) . . . . ? 
 C14 C7 C8 C13 43.1(4) . . . . ? 
 C1 C7 C8 C13 -140.1(2) . . . . ? 
 C13 C8 C9 C10 -2.8(4) . . . . ? 
 C7 C8 C9 C10 174.8(2) . . . . ? 
 C8 C9 C10 C11 1.8(4) . . . . ? 
 C9 C10 C11 C12 0.6(4) . . . . ? 
 C10 C11 C12 C13 -2.0(5) . . . . ? 
 C11 C12 C13 C8 1.0(4) . . . . ? 
 C9 C8 C13 C12 1.4(4) . . . . ? 
 C7 C8 C13 C12 -176.2(2) . . . . ? 
 C8 C7 C14 C15 -171.0(2) . . . . ? 
 C1 C7 C14 C15 12.3(4) . . . . ? 
 C8 C7 C14 C22 -1.9(4) . . . . ? 
 C1 C7 C14 C22 -178.7(2) . . . . ? 
 C7 C14 C15 C16 118.2(3) . . . . ? 
 C22 C14 C15 C16 -53.9(2) . . . . ? 
 C7 C14 C15 C24 -134.6(3) . . . . ? 
 C22 C14 C15 C24 53.3(2) . . . . ? 
 C24 C15 C16 C17 110.3(3) . . . . ? 
 C14 C15 C16 C17 -145.9(3) . . . . ? 
 C24 C15 C16 C21 -70.0(2) . . . . ? 
 C14 C15 C16 C21 33.8(2) . . . . ? 
 C21 C16 C17 C18 -0.9(4) . . . . ? 
 C15 C16 C17 C18 178.8(3) . . . . ? 
 C16 C17 C18 C19 1.1(5) . . . . ? 
 C17 C18 C19 C20 0.5(5) . . . . ? 
 C18 C19 C20 C21 -2.2(4) . . . . ? 
 C19 C20 C21 C16 2.4(4) . . . . ? 
 C19 C20 C21 C22 -179.4(3) . . . . ? 
 C17 C16 C21 C20 -0.9(4) . . . . ? 
 C15 C16 C21 C20 179.4(2) . . . . ? 
 C17 C16 C21 C22 -179.5(2) . . . . ? 
 C15 C16 C21 C22 0.7(3) . . . . ? 
 C20 C21 C22 C14 146.9(3) . . . . ? 
 C16 C21 C22 C14 -34.7(2) . . . . ? 
 C20 C21 C22 C23 -107.6(3) . . . . ? 
 C16 C21 C22 C23 70.8(2) . . . . ? 
 C7 C14 C22 C21 -117.3(3) . . . . ? 
 C15 C14 C22 C21 54.1(2) . . . . ? 
 C7 C14 C22 C23 137.8(3) . . . . ? 
 C15 C14 C22 C23 -50.8(2) . . . . ? 
 C21 C22 C23 C24 -72.2(2) . . . . ? 
 C14 C22 C23 C24 28.6(2) . . . . ? 
 C21 C22 C23 C25 -163.5(2) . . . . ? 
 C14 C22 C23 C25 -62.7(3) . . . . ? 
 C25 O3 C24 C15 -119.6(2) . . . . ? 
 C25 O3 C24 C23 -12.3(2) . . . . ? 
 C16 C15 C24 O3 161.8(2) . . . . ? 
 C14 C15 C24 O3 60.4(2) . . . . ? 
 C16 C15 C24 C23 64.4(2) . . . . ? 
 C14 C15 C24 C23 -37.1(2) . . . . ? 
 C25 C23 C24 O3 11.6(2) . . . . ? 
 C22 C23 C24 O3 -108.7(2) . . . . ? 
 C25 C23 C24 C15 125.5(2) . . . . ? 
 C22 C23 C24 C15 5.2(2) . . . . ? 
 C24 O3 C25 C26 143.5(2) . . . . ? 
 C24 O3 C25 C32 -100.7(2) . . . . ? 
 C24 O3 C25 C23 12.3(2) . . . . ? 
 C24 C23 C25 O3 -11.7(2) . . . . ? 
 C22 C23 C25 O3 89.4(2) . . . . ? 
 C24 C23 C25 C26 -137.3(2) . . . . ? 
 C22 C23 C25 C26 -36.1(3) . . . . ? 
 C24 C23 C25 C32 98.5(2) . . . . ? 
 C22 C23 C25 C32 -160.3(2) . . . . ? 
 O3 C25 C26 C27 -55.6(3) . . . . ? 
 C32 C25 C26 C27 -174.6(2) . . . . ? 
 C23 C25 C26 C27 57.4(4) . . . . ? 
 O3 C25 C26 C31 122.2(2) . . . . ? 
 C32 C25 C26 C31 3.1(2) . . . . ? 
 C23 C25 C26 C31 -124.9(2) . . . . ? 
 C31 C26 C27 C28 1.0(4) . . . . ? 
 C25 C26 C27 C28 178.5(2) . . . . ? 
 C26 C27 C28 C29 -1.1(4) . . . . ? 
 C27 C28 C29 C30 1.4(4) . . . . ? 
 C28 C29 C30 C31 -1.4(4) . . . . ? 
 C29 C30 C31 C26 1.2(4) . . . . ? 
 C29 C30 C31 N1 -176.9(2) . . . . ? 
 C27 C26 C31 C30 -1.0(4) . . . . ? 
 C25 C26 C31 C30 -179.1(2) . . . . ? 
 C27 C26 C31 N1 177.4(2) . . . . ? 
 C25 C26 C31 N1 -0.6(3) . . . . ? 
 C32 N1 C31 C30 175.8(2) . . . . ? 
 C33 N1 C31 C30 5.6(4) . . . . ? 
 C32 N1 C31 C26 -2.5(3) . . . . ? 
 C33 N1 C31 C26 -172.7(2) . . . . ? 
 C33 N1 C32 O1 -3.9(4) . . . . ? 
 C31 N1 C32 O1 -173.9(3) . . . . ? 
 C33 N1 C32 C25 174.5(2) . . . . ? 
 C31 N1 C32 C25 4.4(3) . . . . ? 
 O3 C25 C32 O1 48.4(3) . . . . ? 
 C26 C25 C32 O1 173.8(3) . . . . ? 
 C23 C25 C32 O1 -50.0(3) . . . . ? 
 O3 C25 C32 N1 -130.0(2) . . . . ? 
 C26 C25 C32 N1 -4.6(3) . . . . ? 
 C23 C25 C32 N1 131.6(2) . . . . ? 
 C32 N1 C33 O2 -170.3(3) . . . . ? 
 C31 N1 C33 O2 -1.7(4) . . . . ? 
 C32 N1 C33 C34 10.0(4) . . . . ? 
 C31 N1 C33 C34 178.6(2) . . . . ? 
 
_refine_diff_density_max    0.225 
_refine_diff_density_min   -0.214 
_refine_diff_density_rms    0.036 

data_compound8 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic:(3R,3'R)-1-Acetyl-2-oxo-3'-phenylspiro[3H-indole-3,2'-oxetane] 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point108-109            
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C18 H15 N O3' 
_chemical_formula_weight          293.31 
 
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' 
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    'P 21/c'
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    9.4575(2) 
_cell_length_b                    17.2629(3) 
_cell_length_c                    9.2678(1) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  98.894(1) 
_cell_angle_gamma                 90.00 
_cell_volume                      1494.90(4) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     4466 
_cell_measurement_theta_min       2.18 
_cell_measurement_theta_max       28.31 
 
_exptl_crystal_description        slab
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.46 
_exptl_crystal_size_mid           0.34 
_exptl_crystal_size_min           0.24 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.303 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              616 
_exptl_absorpt_coefficient_mu     0.089 
_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       293(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
;
Siemens SMART CCD area detector diffractometer
;
_diffrn_measurement_method        '\w scans' 
_diffrn_detector_area_resol_mean  8.33
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             10318 
_diffrn_reflns_av_R_equivalents   0.0690 
_diffrn_reflns_av_sigmaI/netI     0.0766 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -20 
_diffrn_reflns_limit_k_max        22 
_diffrn_reflns_limit_l_min        -7 
_diffrn_reflns_limit_l_max        12 
_diffrn_reflns_theta_min          2.18 
_diffrn_reflns_theta_max          28.28 
_reflns_number_total              3631 
_reflns_number_gt                 1889 
_reflns_threshold_expression      'I > 2\s(I)' 

_computing_data_collection        'SMART (Siemens, 1996)' 
_computing_cell_refinement        'SAINT (Siemens, 1996)' 
_computing_data_reduction          SAINT 
_computing_structure_solution     'SHELXTL (Sheldrick, 1997)' 
_computing_structure_refinement    SHELXTL  
_computing_molecular_graphics      SHELXTL 
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)
;
 
_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.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_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^)+(0.0779P)^2^+0.0000P] 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      SHELXTL 
_refine_ls_extinction_coef        0.015(3) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_number_reflns          3631 
_refine_ls_number_parameters      200 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1020 
_refine_ls_R_factor_gt            0.0524 
_refine_ls_wR_factor_ref          0.1567 
_refine_ls_wR_factor_gt           0.1372 
_refine_ls_goodness_of_fit_ref    0.895 
_refine_ls_restrained_S_all       0.895 
_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 
O1 O -0.15146(18) 0.01924(10) 0.3522(2) 0.1074(7) Uani 1 1 d . . . 
O2 O 0.21917(15) 0.13717(7) 0.29153(17) 0.0740(5) Uani 1 1 d . . . 
O3 O 0.36411(13) 0.05146(7) 0.08712(13) 0.0573(4) Uani 1 1 d . . . 
N1 N 0.05885(15) 0.03351(8) 0.26632(18) 0.0563(4) Uani 1 1 d . . . 
C1 C 0.3965(2) -0.12435(11) 0.4330(2) 0.0592(5) Uani 1 1 d . . . 
H1A H 0.3298 -0.0986 0.4795 0.071 Uiso 1 1 calc R . . 
C2 C 0.4306(3) -0.20035(13) 0.4686(2) 0.0752(6) Uani 1 1 d . . . 
H2A H 0.3861 -0.2257 0.5380 0.090 Uiso 1 1 calc R . . 
C3 C 0.5299(3) -0.23872(13) 0.4022(3) 0.0793(7) Uani 1 1 d . . . 
H3A H 0.5548 -0.2895 0.4281 0.095 Uiso 1 1 calc R . . 
C4 C 0.5920(3) -0.20206(14) 0.2982(3) 0.0791(7) Uani 1 1 d . . . 
H4A H 0.6583 -0.2282 0.2518 0.095 Uiso 1 1 calc R . . 
C5 C 0.5566(2) -0.12572(12) 0.2609(2) 0.0622(5) Uani 1 1 d . . . 
H5A H 0.5990 -0.1013 0.1889 0.075 Uiso 1 1 calc R . . 
C6 C 0.46037(17) -0.08599(10) 0.32849(18) 0.0442(4) Uani 1 1 d . . . 
C7 C 0.42178(18) -0.00239(10) 0.29756(19) 0.0476(4) Uani 1 1 d . . . 
H7A H 0.4222 0.0264 0.3888 0.057 Uiso 1 1 calc R . . 
C8 C 0.4959(2) 0.04402(12) 0.1903(2) 0.0635(6) Uani 1 1 d . . . 
H8A H 0.5333 0.0933 0.2294 0.076 Uiso 1 1 calc R . . 
H8B H 0.5694 0.0149 0.1519 0.076 Uiso 1 1 calc R . . 
C9 C 0.28256(18) 0.01569(9) 0.18697(19) 0.0457(4) Uani 1 1 d . . . 
C10 C 0.18102(18) -0.04786(9) 0.13151(18) 0.0467(4) Uani 1 1 d . . . 
C11 C 0.1997(2) -0.11040(10) 0.0441(2) 0.0586(5) Uani 1 1 d . . . 
H11A H 0.2851 -0.1173 0.0077 0.070 Uiso 1 1 calc R . . 
C12 C 0.0882(2) -0.16298(12) 0.0116(2) 0.0692(6) Uani 1 1 d . . . 
H12A H 0.0983 -0.2052 -0.0484 0.083 Uiso 1 1 calc R . . 
C13 C -0.0361(2) -0.15310(12) 0.0669(3) 0.0774(7) Uani 1 1 d . . . 
H13A H -0.1089 -0.1895 0.0454 0.093 Uiso 1 1 calc R . . 
C14 C -0.0569(2) -0.09010(12) 0.1546(3) 0.0723(6) Uani 1 1 d . . . 
H14A H -0.1421 -0.0835 0.1914 0.087 Uiso 1 1 calc R . . 
C15 C 0.05359(18) -0.03778(10) 0.1850(2) 0.0513(5) Uani 1 1 d . . . 
C16 C 0.18710(18) 0.07228(10) 0.2535(2) 0.0527(5) Uani 1 1 d . . . 
C17 C -0.0471(2) 0.05864(12) 0.3461(3) 0.0776(7) Uani 1 1 d . . . 
C18 C -0.0208(3) 0.13395(14) 0.4262(4) 0.1151(11) Uani 1 1 d . . . 
H18A H 0.0676 0.1560 0.4068 0.173 Uiso 1 1 calc R . . 
H18B H -0.0152 0.1251 0.5292 0.173 Uiso 1 1 calc R . . 
H18C H -0.0979 0.1691 0.3939 0.173 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 
O1 0.0702(11) 0.0826(12) 0.185(2) -0.0170(12) 0.0683(13) -0.0106(9) 
O2 0.0711(10) 0.0444(8) 0.1104(12) -0.0134(7) 0.0262(8) -0.0097(7) 
O3 0.0522(8) 0.0605(8) 0.0610(8) 0.0081(6) 0.0146(6) -0.0085(6) 
N1 0.0468(9) 0.0417(8) 0.0839(11) 0.0013(7) 0.0213(8) 0.0007(6) 
C1 0.0570(12) 0.0564(12) 0.0665(12) 0.0004(10) 0.0163(10) -0.0058(9) 
C2 0.0891(17) 0.0571(13) 0.0778(15) 0.0129(11) 0.0081(12) -0.0144(12) 
C3 0.0955(18) 0.0463(12) 0.0883(17) -0.0020(11) -0.0106(14) 0.0064(12) 
C4 0.0826(16) 0.0679(15) 0.0852(16) -0.0115(12) 0.0079(13) 0.0233(12) 
C5 0.0591(12) 0.0656(13) 0.0643(12) -0.0017(10) 0.0166(10) 0.0075(10) 
C6 0.0374(9) 0.0475(10) 0.0470(10) -0.0021(7) 0.0040(7) -0.0040(7) 
C7 0.0420(9) 0.0440(10) 0.0564(11) -0.0042(8) 0.0069(8) -0.0062(7) 
C8 0.0477(11) 0.0561(12) 0.0868(14) 0.0091(10) 0.0108(10) -0.0115(9) 
C9 0.0418(9) 0.0429(9) 0.0540(10) 0.0025(8) 0.0124(8) -0.0019(7) 
C10 0.0426(9) 0.0412(9) 0.0552(11) 0.0028(8) 0.0039(8) -0.0005(7) 
C11 0.0599(12) 0.0492(11) 0.0655(12) -0.0058(9) 0.0054(9) -0.0009(9) 
C12 0.0769(15) 0.0488(11) 0.0777(14) -0.0092(10) -0.0014(12) -0.0050(10) 
C13 0.0626(14) 0.0541(13) 0.1109(18) -0.0049(12) -0.0016(13) -0.0160(10) 
C14 0.0476(12) 0.0554(13) 0.1135(18) 0.0039(12) 0.0115(11) -0.0077(9) 
C15 0.0427(10) 0.0391(9) 0.0717(12) 0.0052(8) 0.0076(9) 0.0006(7) 
C16 0.0469(10) 0.0428(10) 0.0695(12) 0.0029(9) 0.0127(9) -0.0036(8) 
C17 0.0618(14) 0.0573(13) 0.123(2) 0.0038(13) 0.0438(14) 0.0067(11) 
C18 0.120(2) 0.0721(17) 0.177(3) -0.0359(18) 0.095(2) -0.0060(15) 
 
_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 
O1 C17 1.207(2) . ? 
O2 C16 1.199(2) . ? 
O3 C9 1.433(2) . ? 
O3 C8 1.455(2) . ? 
N1 C17 1.403(2) . ? 
N1 C16 1.406(2) . ? 
N1 C15 1.440(2) . ? 
C1 C2 1.379(3) . ? 
C1 C6 1.386(2) . ? 
C1 H1A 0.9300 . ? 
C2 C3 1.371(3) . ? 
C2 H2A 0.9300 . ? 
C3 C4 1.360(3) . ? 
C3 H3A 0.9300 . ? 
C4 C5 1.390(3) . ? 
C4 H4A 0.9300 . ? 
C5 C6 1.367(2) . ? 
C5 H5A 0.9300 . ? 
C6 C7 1.505(2) . ? 
C7 C8 1.528(2) . ? 
C7 C9 1.570(2) . ? 
C7 H7A 0.9800 . ? 
C8 H8A 0.9700 . ? 
C8 H8B 0.9700 . ? 
C9 C10 1.496(2) . ? 
C9 C16 1.524(2) . ? 
C10 C11 1.377(2) . ? 
C10 C15 1.383(2) . ? 
C11 C12 1.389(3) . ? 
C11 H11A 0.9300 . ? 
C12 C13 1.364(3) . ? 
C12 H12A 0.9300 . ? 
C13 C14 1.390(3) . ? 
C13 H13A 0.9300 . ? 
C14 C15 1.377(3) . ? 
C14 H14A 0.9300 . ? 
C17 C18 1.499(3) . ? 
C18 H18A 0.9600 . ? 
C18 H18B 0.9600 . ? 
C18 H18C 0.9600 . ? 
 
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 
C9 O3 C8 91.67(12) . . ? 
C17 N1 C16 126.36(17) . . ? 
C17 N1 C15 124.78(15) . . ? 
C16 N1 C15 108.86(14) . . ? 
C2 C1 C6 120.68(19) . . ? 
C2 C1 H1A 119.7 . . ? 
C6 C1 H1A 119.7 . . ? 
C3 C2 C1 120.2(2) . . ? 
C3 C2 H2A 119.9 . . ? 
C1 C2 H2A 119.9 . . ? 
C4 C3 C2 119.6(2) . . ? 
C4 C3 H3A 120.2 . . ? 
C2 C3 H3A 120.2 . . ? 
C3 C4 C5 120.3(2) . . ? 
C3 C4 H4A 119.9 . . ? 
C5 C4 H4A 119.9 . . ? 
C6 C5 C4 120.89(19) . . ? 
C6 C5 H5A 119.6 . . ? 
C4 C5 H5A 119.6 . . ? 
C5 C6 C1 118.28(18) . . ? 
C5 C6 C7 123.56(16) . . ? 
C1 C6 C7 118.16(15) . . ? 
C6 C7 C8 120.29(15) . . ? 
C6 C7 C9 117.98(13) . . ? 
C8 C7 C9 83.90(13) . . ? 
C6 C7 H7A 110.7 . . ? 
C8 C7 H7A 110.7 . . ? 
C9 C7 H7A 110.7 . . ? 
O3 C8 C7 92.38(13) . . ? 
O3 C8 H8A 113.2 . . ? 
C7 C8 H8A 113.2 . . ? 
O3 C8 H8B 113.2 . . ? 
C7 C8 H8B 113.2 . . ? 
H8A C8 H8B 110.6 . . ? 
O3 C9 C10 118.37(14) . . ? 
O3 C9 C16 113.39(13) . . ? 
C10 C9 C16 102.72(13) . . ? 
O3 C9 C7 91.52(12) . . ? 
C10 C9 C7 120.50(14) . . ? 
C16 C9 C7 110.66(14) . . ? 
C11 C10 C15 120.50(16) . . ? 
C11 C10 C9 130.02(16) . . ? 
C15 C10 C9 109.46(15) . . ? 
C10 C11 C12 118.56(18) . . ? 
C10 C11 H11A 120.7 . . ? 
C12 C11 H11A 120.7 . . ? 
C13 C12 C11 120.40(19) . . ? 
C13 C12 H12A 119.8 . . ? 
C11 C12 H12A 119.8 . . ? 
C12 C13 C14 121.70(19) . . ? 
C12 C13 H13A 119.1 . . ? 
C14 C13 H13A 119.1 . . ? 
C15 C14 C13 117.5(2) . . ? 
C15 C14 H14A 121.2 . . ? 
C13 C14 H14A 121.2 . . ? 
C14 C15 C10 121.30(18) . . ? 
C14 C15 N1 129.17(17) . . ? 
C10 C15 N1 109.49(14) . . ? 
O2 C16 N1 127.03(17) . . ? 
O2 C16 C9 125.38(16) . . ? 
N1 C16 C9 107.56(14) . . ? 
O1 C17 N1 120.4(2) . . ? 
O1 C17 C18 122.7(2) . . ? 
N1 C17 C18 116.87(19) . . ? 
C17 C18 H18A 109.5 . . ? 
C17 C18 H18B 109.5 . . ? 
H18A C18 H18B 109.5 . . ? 
C17 C18 H18C 109.5 . . ? 
H18A C18 H18C 109.5 . . ? 
H18B C18 H18C 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 
C6 C1 C2 C3 0.8(3) . . . . ? 
C1 C2 C3 C4 -1.7(3) . . . . ? 
C2 C3 C4 C5 1.0(3) . . . . ? 
C3 C4 C5 C6 0.6(3) . . . . ? 
C4 C5 C6 C1 -1.4(3) . . . . ? 
C4 C5 C6 C7 177.49(18) . . . . ? 
C2 C1 C6 C5 0.7(3) . . . . ? 
C2 C1 C6 C7 -178.25(18) . . . . ? 
C5 C6 C7 C8 -2.7(3) . . . . ? 
C1 C6 C7 C8 176.24(16) . . . . ? 
C5 C6 C7 C9 97.2(2) . . . . ? 
C1 C6 C7 C9 -83.9(2) . . . . ? 
C9 O3 C8 C7 5.73(14) . . . . ? 
C6 C7 C8 O3 113.70(16) . . . . ? 
C9 C7 C8 O3 -5.25(12) . . . . ? 
C8 O3 C9 C10 -131.83(16) . . . . ? 
C8 O3 C9 C16 107.75(16) . . . . ? 
C8 O3 C9 C7 -5.57(13) . . . . ? 
C6 C7 C9 O3 -115.84(15) . . . . ? 
C8 C7 C9 O3 5.33(13) . . . . ? 
C6 C7 C9 C10 8.7(2) . . . . ? 
C8 C7 C9 C10 129.90(17) . . . . ? 
C6 C7 C9 C16 128.41(15) . . . . ? 
C8 C7 C9 C16 -110.42(15) . . . . ? 
O3 C9 C10 C11 44.8(2) . . . . ? 
C16 C9 C10 C11 170.53(17) . . . . ? 
C7 C9 C10 C11 -65.9(2) . . . . ? 
O3 C9 C10 C15 -136.81(16) . . . . ? 
C16 C9 C10 C15 -11.04(18) . . . . ? 
C7 C9 C10 C15 112.51(17) . . . . ? 
C15 C10 C11 C12 -0.2(3) . . . . ? 
C9 C10 C11 C12 178.08(18) . . . . ? 
C10 C11 C12 C13 -0.9(3) . . . . ? 
C11 C12 C13 C14 1.2(3) . . . . ? 
C12 C13 C14 C15 -0.5(3) . . . . ? 
C13 C14 C15 C10 -0.6(3) . . . . ? 
C13 C14 C15 N1 176.94(19) . . . . ? 
C11 C10 C15 C14 0.9(3) . . . . ? 
C9 C10 C15 C14 -177.65(18) . . . . ? 
C11 C10 C15 N1 -177.04(15) . . . . ? 
C9 C10 C15 N1 4.4(2) . . . . ? 
C17 N1 C15 C14 7.9(3) . . . . ? 
C16 N1 C15 C14 -172.8(2) . . . . ? 
C17 N1 C15 C10 -174.29(18) . . . . ? 
C16 N1 C15 C10 5.0(2) . . . . ? 
C17 N1 C16 O2 -10.6(3) . . . . ? 
C15 N1 C16 O2 170.10(19) . . . . ? 
C17 N1 C16 C9 167.27(19) . . . . ? 
C15 N1 C16 C9 -12.0(2) . . . . ? 
O3 C9 C16 O2 -39.2(3) . . . . ? 
C10 C9 C16 O2 -168.16(18) . . . . ? 
C7 C9 C16 O2 62.0(2) . . . . ? 
O3 C9 C16 N1 142.82(15) . . . . ? 
C10 C9 C16 N1 13.88(18) . . . . ? 
C7 C9 C16 N1 -116.00(15) . . . . ? 
C16 N1 C17 O1 -178.0(2) . . . . ? 
C15 N1 C17 O1 1.1(4) . . . . ? 
C16 N1 C17 C18 -0.4(3) . . . . ? 
C15 N1 C17 C18 178.8(2) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.980 
_diffrn_reflns_theta_full              28.28 
_diffrn_measured_fraction_theta_full   0.980 
_refine_diff_density_max    0.223 
_refine_diff_density_min   -0.190 
_refine_diff_density_rms    0.045