# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2011

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Gharpure, Santosh'
_publ_contact_author_email       sjgharpure@iitm.ac.in

_publ_section_title              
;
Stereoselective synthesis of oxazino
[4,3-a]indoles employing oxa-Pictet-Spengler reaction
of indoles bearing N-tethered vinylogous caronate
;
loop_
_publ_author_name
S.J.Gharpure
A.M.Sathiyanarayanan

# Attachment '- SJG1.cif'

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 801688'
#TrackingRef '- SJG1.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 N O3'
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         273.32

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/n'
_symmetry_space_group_name_Hall  '-P 2yn '

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                   10.4764(4)
_cell_length_b                   8.4739(3)
_cell_length_c                   17.5527(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.944(2)
_cell_angle_gamma                90.00
_cell_volume                     1518.66(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(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          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9694
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_process_details   'SADABS (Bruker,2004)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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 APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12548
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         29.06
_reflns_number_total             3748
_reflns_number_gt                2032
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0944P)^2^+0.1235P] 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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3748
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1851
_refine_ls_wR_factor_gt          0.1533
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_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 0.67414(19) 0.1478(2) -0.02963(12) 0.0555(5) Uani 1 1 d . . .
C2 C 0.6333(2) 0.2212(3) -0.10170(13) 0.0732(6) Uani 1 1 d . . .
H2 H 0.5632 0.2912 -0.1114 0.088 Uiso 1 1 calc R . .
C3 C 0.7008(3) 0.1862(4) -0.15798(16) 0.0925(8) Uani 1 1 d . . .
H3 H 0.6763 0.2339 -0.2068 0.111 Uiso 1 1 calc R . .
C4 C 0.8054(3) 0.0805(4) -0.14360(16) 0.0973(9) Uani 1 1 d . . .
H4 H 0.8484 0.0582 -0.1833 0.117 Uiso 1 1 calc R . .
C5 C 0.8462(2) 0.0091(3) -0.07264(15) 0.0787(7) Uani 1 1 d . . .
H5 H 0.9165 -0.0607 -0.0638 0.094 Uiso 1 1 calc R . .
C6 C 0.78023(18) 0.0426(2) -0.01345(12) 0.0589(5) Uani 1 1 d . . .
C7 C 0.79236(18) -0.0081(2) 0.06524(13) 0.0580(5) Uani 1 1 d . . .
C8 C 0.69699(15) 0.0643(2) 0.09324(11) 0.0485(4) Uani 1 1 d . . .
C9 C 0.65956(16) 0.0571(2) 0.17038(11) 0.0496(5) Uani 1 1 d . . .
H9 H 0.6040 -0.0357 0.1713 0.059 Uiso 1 1 calc R . .
C10 C 0.47551(16) 0.2142(2) 0.12000(12) 0.0558(5) Uani 1 1 d . . .
H10 H 0.4287 0.1134 0.1109 0.067 Uiso 1 1 calc R . .
C11 C 0.51781(17) 0.2615(2) 0.04687(12) 0.0590(5) Uani 1 1 d . . .
H11A H 0.4443 0.2534 0.0022 0.071 Uiso 1 1 calc R . .
H11B H 0.5477 0.3702 0.0511 0.071 Uiso 1 1 calc R . .
C12 C 0.77887(16) 0.0466(2) 0.23814(11) 0.0572(5) Uani 1 1 d . . .
H12A H 0.8264 -0.0494 0.2326 0.069 Uiso 1 1 calc R . .
H12B H 0.8362 0.1350 0.2350 0.069 Uiso 1 1 calc R . .
C13 C 0.74706(19) 0.0471(2) 0.31679(13) 0.0615(5) Uani 1 1 d . . .
C14 C 0.6045(3) -0.0532(4) 0.39264(17) 0.1109(11) Uani 1 1 d . . .
H14A H 0.6014 -0.1618 0.4096 0.133 Uiso 1 1 calc R A 1
H14B H 0.6660 0.0039 0.4327 0.133 Uiso 1 1 calc R A 1
C15A C 0.4761(6) 0.0173(11) 0.3815(4) 0.122(2) Uani 0.571(6) 1 d P B 1
H15A H 0.4229 -0.0167 0.3323 0.183 Uiso 0.571(6) 1 calc PR B 1
H15B H 0.4841 0.1302 0.3816 0.183 Uiso 0.571(6) 1 calc PR B 1
H15C H 0.4359 -0.0147 0.4231 0.183 Uiso 0.571(6) 1 calc PR B 1
C15B C 0.4853(9) -0.1059(14) 0.3848(6) 0.122(2) Uani 0.429(6) 1 d P B 2
H15D H 0.4251 -0.0345 0.3528 0.183 Uiso 0.429(6) 1 calc PR B 2
H15E H 0.4649 -0.1140 0.4353 0.183 Uiso 0.429(6) 1 calc PR B 2
H15F H 0.4781 -0.2081 0.3606 0.183 Uiso 0.429(6) 1 calc PR B 2
C16 C 0.3876(2) 0.3359(3) 0.14445(16) 0.0832(7) Uani 1 1 d . . .
H16A H 0.3536 0.2953 0.1870 0.125 Uiso 1 1 calc R . .
H16B H 0.3164 0.3595 0.1011 0.125 Uiso 1 1 calc R . .
H16C H 0.4368 0.4302 0.1608 0.125 Uiso 1 1 calc R . .
N1 N 0.62351(13) 0.15820(17) 0.03575(9) 0.0513(4) Uani 1 1 d . . .
O1 O 0.58872(11) 0.19546(14) 0.18220(7) 0.0538(4) Uani 1 1 d . . .
O2 O 0.64730(14) -0.0479(2) 0.31969(9) 0.0789(5) Uani 1 1 d . B .
O3 O 0.80566(18) 0.1200(2) 0.37129(10) 0.1042(6) Uani 1 1 d . . .
H7 H 0.855(2) -0.074(2) 0.0923(13) 0.069(6) Uiso 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 0.0580(10) 0.0553(10) 0.0492(12) -0.0015(8) 0.0036(9) -0.0100(8)
C2 0.0832(14) 0.0758(14) 0.0559(14) 0.0054(11) 0.0056(12) -0.0076(11)
C3 0.1046(19) 0.113(2) 0.0579(16) 0.0127(14) 0.0131(15) -0.0180(17)
C4 0.0998(19) 0.134(2) 0.0647(18) -0.0074(17) 0.0319(15) -0.0210(18)
C5 0.0669(13) 0.1009(17) 0.0703(17) -0.0117(13) 0.0195(12) -0.0086(12)
C6 0.0522(10) 0.0683(12) 0.0548(13) -0.0072(10) 0.0093(9) -0.0104(9)
C7 0.0486(10) 0.0630(11) 0.0601(14) 0.0003(10) 0.0073(10) 0.0049(9)
C8 0.0431(9) 0.0466(9) 0.0520(11) 0.0014(8) 0.0024(8) -0.0024(7)
C9 0.0444(9) 0.0486(9) 0.0531(12) 0.0008(8) 0.0053(8) -0.0011(7)
C10 0.0415(9) 0.0580(11) 0.0621(13) -0.0046(9) -0.0007(9) 0.0025(8)
C11 0.0517(10) 0.0561(10) 0.0611(13) -0.0001(9) -0.0047(10) 0.0069(8)
C12 0.0467(10) 0.0628(11) 0.0584(13) 0.0077(9) 0.0036(9) 0.0014(8)
C13 0.0562(11) 0.0674(12) 0.0558(13) 0.0065(10) 0.0015(11) 0.0083(9)
C14 0.097(2) 0.167(3) 0.079(2) 0.0303(19) 0.0410(16) 0.0178(19)
C15A 0.106(3) 0.159(6) 0.112(3) 0.003(5) 0.050(2) 0.024(5)
C15B 0.106(3) 0.159(6) 0.112(3) 0.003(5) 0.050(2) 0.024(5)
C16 0.0684(13) 0.0903(16) 0.0894(18) -0.0113(13) 0.0142(13) 0.0224(12)
N1 0.0498(8) 0.0533(8) 0.0476(10) 0.0014(7) 0.0039(7) 0.0003(6)
O1 0.0477(7) 0.0561(7) 0.0535(8) -0.0063(6) 0.0026(6) 0.0033(5)
O2 0.0732(9) 0.1060(12) 0.0602(10) 0.0082(8) 0.0206(8) -0.0042(8)
O3 0.1168(14) 0.1215(15) 0.0647(12) -0.0225(10) 0.0002(11) -0.0199(12)

_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 N1 1.371(2) . ?
C1 C2 1.389(3) . ?
C1 C6 1.404(3) . ?
C2 C3 1.370(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.425(3) . ?
C7 C8 1.355(3) . ?
C7 H7 0.91(2) . ?
C8 N1 1.377(2) . ?
C8 C9 1.493(3) . ?
C9 O1 1.428(2) . ?
C9 C12 1.523(3) . ?
C9 H9 0.9800 . ?
C10 O1 1.430(2) . ?
C10 C11 1.503(3) . ?
C10 C16 1.507(3) . ?
C10 H10 0.9800 . ?
C11 N1 1.458(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.491(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O3 1.188(2) . ?
C13 O2 1.329(2) . ?
C14 C15B 1.305(9) . ?
C14 C15A 1.445(7) . ?
C14 O2 1.449(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
N1 C1 C2 129.51(19) . . ?
N1 C1 C6 107.99(16) . . ?
C2 C1 C6 122.5(2) . . ?
C3 C2 C1 117.2(2) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 118.8(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 C7 135.0(2) . . ?
C1 C6 C7 106.40(17) . . ?
C8 C7 C6 107.58(18) . . ?
C8 C7 H7 126.4(13) . . ?
C6 C7 H7 126.0(13) . . ?
C7 C8 N1 109.42(18) . . ?
C7 C8 C9 132.45(17) . . ?
N1 C8 C9 118.12(15) . . ?
O1 C9 C8 110.40(14) . . ?
O1 C9 C12 107.26(15) . . ?
C8 C9 C12 111.99(14) . . ?
O1 C9 H9 109.0 . . ?
C8 C9 H9 109.0 . . ?
C12 C9 H9 109.0 . . ?
O1 C10 C11 109.20(14) . . ?
O1 C10 C16 108.29(17) . . ?
C11 C10 C16 112.13(17) . . ?
O1 C10 H10 109.1 . . ?
C11 C10 H10 109.1 . . ?
C16 C10 H10 109.1 . . ?
N1 C11 C10 109.41(15) . . ?
N1 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
N1 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C9 114.11(15) . . ?
C13 C12 H12A 108.7 . . ?
C9 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C9 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
O3 C13 O2 123.6(2) . . ?
O3 C13 C12 124.4(2) . . ?
O2 C13 C12 112.00(19) . . ?
C15B C14 C15A 44.5(4) . . ?
C15B C14 O2 113.3(5) . . ?
C15A C14 O2 109.3(3) . . ?
C15B C14 H14A 67.0 . . ?
C15A C14 H14A 109.8 . . ?
O2 C14 H14A 109.8 . . ?
C15B C14 H14B 135.4 . . ?
C15A C14 H14B 109.8 . . ?
O2 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
C14 C15A H15A 109.5 . . ?
C14 C15A H15B 109.5 . . ?
C14 C15A H15C 109.5 . . ?
C14 C15B H15D 109.5 . . ?
C14 C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C14 C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 N1 C8 108.60(15) . . ?
C1 N1 C11 126.75(16) . . ?
C8 N1 C11 124.42(16) . . ?
C9 O1 C10 110.47(13) . . ?
C13 O2 C14 117.0(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
N1 C1 C2 C3 -178.41(19) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C4 C5 C6 C7 179.2(2) . . . . ?
N1 C1 C6 C5 178.24(17) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
N1 C1 C6 C7 -0.87(19) . . . . ?
C2 C1 C6 C7 -179.93(19) . . . . ?
C5 C6 C7 C8 -178.7(2) . . . . ?
C1 C6 C7 C8 0.2(2) . . . . ?
C6 C7 C8 N1 0.5(2) . . . . ?
C6 C7 C8 C9 179.21(17) . . . . ?
C7 C8 C9 O1 157.52(18) . . . . ?
N1 C8 C9 O1 -23.9(2) . . . . ?
C7 C8 C9 C12 38.1(3) . . . . ?
N1 C8 C9 C12 -143.34(16) . . . . ?
O1 C10 C11 N1 47.76(19) . . . . ?
C16 C10 C11 N1 167.79(15) . . . . ?
O1 C9 C12 C13 55.9(2) . . . . ?
C8 C9 C12 C13 177.14(16) . . . . ?
C9 C12 C13 O3 -137.3(2) . . . . ?
C9 C12 C13 O2 44.6(2) . . . . ?
C2 C1 N1 C8 -179.82(19) . . . . ?
C6 C1 N1 C8 1.21(19) . . . . ?
C2 C1 N1 C11 -5.2(3) . . . . ?
C6 C1 N1 C11 175.80(15) . . . . ?
C7 C8 N1 C1 -1.09(19) . . . . ?
C9 C8 N1 C1 -179.99(14) . . . . ?
C7 C8 N1 C11 -175.84(15) . . . . ?
C9 C8 N1 C11 5.3(2) . . . . ?
C10 C11 N1 C1 169.27(16) . . . . ?
C10 C11 N1 C8 -17.0(2) . . . . ?
C8 C9 O1 C10 57.05(17) . . . . ?
C12 C9 O1 C10 179.32(14) . . . . ?
C11 C10 O1 C9 -71.37(18) . . . . ?
C16 C10 O1 C9 166.26(16) . . . . ?
O3 C13 O2 C14 3.9(3) . . . . ?
C12 C13 O2 C14 -177.99(18) . . . . ?
C15B C14 O2 C13 159.5(6) . . . . ?
C15A C14 O2 C13 111.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.922
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.049

# Attachment '- SJG2.cif'

data_pox
_database_code_depnum_ccdc_archive 'CCDC 801689'
#TrackingRef '- SJG2.cif'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C14 H15 N O3'

_chemical_formula_weight         245.27

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   P2(1)/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                   6.05110(10)

_cell_length_b                   14.5244(5)

_cell_length_c                   14.0584(5)

_cell_angle_alpha                90.00

_cell_angle_beta                 100.186(2)

_cell_angle_gamma                90.00

_cell_volume                     1216.10(6)

_cell_formula_units_Z            4

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    2420

_cell_measurement_theta_min      2.80

_cell_measurement_theta_max      25.29

_exptl_crystal_description       Prism

_exptl_crystal_colour            clear

_exptl_crystal_size_max          0.35

_exptl_crystal_size_mid          0.28

_exptl_crystal_size_min          0.15

_exptl_crystal_density_meas      0

_exptl_crystal_density_diffrn    1.340

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             520

_exptl_absorpt_coefficient_mu    0.095

_exptl_absorpt_correction_type   none

_exptl_absorpt_correction_T_min  0.9677

_exptl_absorpt_correction_T_max  0.9860

_exptl_absorpt_process_details   ?

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      298(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  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            8987

_diffrn_reflns_av_R_equivalents  0.0323

_diffrn_reflns_av_sigmaI/netI    0.0418

_diffrn_reflns_limit_h_min       -7

_diffrn_reflns_limit_h_max       6

_diffrn_reflns_limit_k_min       -15

_diffrn_reflns_limit_k_max       19

_diffrn_reflns_limit_l_min       -18

_diffrn_reflns_limit_l_max       16

_diffrn_reflns_theta_min         3.17

_diffrn_reflns_theta_max         28.30

_reflns_number_total             2805

_reflns_number_gt                1883

_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.1000P)^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    mixed

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         2805

_refine_ls_number_parameters     164

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0749

_refine_ls_R_factor_gt           0.0440

_refine_ls_wR_factor_ref         0.1434

_refine_ls_wR_factor_gt          0.1207

_refine_ls_goodness_of_fit_ref   0.901

_refine_ls_restrained_S_all      0.901

_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 0.6820(2) 0.21807(10) 0.82592(11) 0.0290(4) Uani 1 1 d . . .
C2 C 0.5965(3) 0.19786(12) 0.90905(12) 0.0371(4) Uani 1 1 d . . .
H2 H 0.6072 0.2399 0.9596 0.044 Uiso 1 1 calc R . .
C3 C 0.4953(3) 0.11350(13) 0.91394(14) 0.0453(5) Uani 1 1 d . . .
H3 H 0.4368 0.0991 0.9690 0.054 Uiso 1 1 calc R . .
C4 C 0.4769(3) 0.04862(12) 0.83963(15) 0.0487(5) Uani 1 1 d . . .
H4 H 0.4024 -0.0067 0.8445 0.058 Uiso 1 1 calc R . .
C5 C 0.5693(3) 0.06699(12) 0.75950(14) 0.0424(4) Uani 1 1 d . . .
H5 H 0.5614 0.0239 0.7101 0.051 Uiso 1 1 calc R . .
C6 C 0.6752(2) 0.15129(10) 0.75331(11) 0.0313(4) Uani 1 1 d . . .
C7 C 0.7913(2) 0.18869(11) 0.68079(11) 0.0320(4) Uani 1 1 d . . .
C8 C 0.8829(2) 0.28388(10) 0.71811(11) 0.0295(4) Uani 1 1 d . . .
C9 C 1.0243(3) 0.38056(14) 0.61000(14) 0.0485(5) Uani 1 1 d . . .
H9A H 1.0689 0.4423 0.6316 0.058 Uiso 1 1 calc R . .
H9B H 0.9959 0.3796 0.5399 0.058 Uiso 1 1 calc R . .
C10 C 1.2055(3) 0.31200(13) 0.64948(13) 0.0417(4) Uani 1 1 d . . .
H10A H 1.2042 0.2596 0.6065 0.050 Uiso 1 1 calc R . .
H10B H 1.3530 0.3403 0.6594 0.050 Uiso 1 1 calc R . .
C11 C 1.1414(2) 0.28391(11) 0.74418(11) 0.0321(4) Uani 1 1 d . . .
H11 H 1.2005 0.2230 0.7651 0.039 Uiso 1 1 calc R . .
C12 C 1.1255(2) 0.34832(11) 0.89942(11) 0.0330(4) Uani 1 1 d . . .
H12 H 1.1484 0.2864 0.9271 0.040 Uiso 1 1 calc R . .
C13 C 0.8773(3) 0.36691(11) 0.87187(12) 0.0348(4) Uani 1 1 d . . .
H13A H 0.8078 0.3633 0.9289 0.042 Uiso 1 1 calc R . .
H13B H 0.8537 0.4285 0.8453 0.042 Uiso 1 1 calc R . .
C14 C 1.2461(3) 0.41746(12) 0.97019(13) 0.0443(4) Uani 1 1 d . . .
H14A H 1.4038 0.4038 0.9828 0.067 Uiso 1 1 calc R . .
H14B H 1.1883 0.4144 1.0294 0.067 Uiso 1 1 calc R . .
H14C H 1.2231 0.4782 0.9434 0.067 Uiso 1 1 calc R . .
N1 N 0.77355(19) 0.29991(8) 0.80060(9) 0.0307(3) Uani 1 1 d . . .
O1 O 0.8193(2) 0.15665(9) 0.60372(9) 0.0493(4) Uani 1 1 d . . .
O2 O 0.82686(17) 0.35275(7) 0.64663(8) 0.0388(3) Uani 1 1 d . . .
O3 O 1.22115(16) 0.35309(7) 0.81323(8) 0.0348(3) 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 0.0221(7) 0.0349(8) 0.0292(8) 0.0014(7) 0.0022(6) 0.0024(6)
C2 0.0351(9) 0.0436(10) 0.0323(9) 0.0004(7) 0.0054(7) 0.0031(7)
C3 0.0447(10) 0.0509(11) 0.0426(11) 0.0147(9) 0.0140(8) 0.0027(8)
C4 0.0499(10) 0.0351(9) 0.0630(13) 0.0091(9) 0.0153(9) -0.0046(8)
C5 0.0452(10) 0.0328(9) 0.0496(11) -0.0044(8) 0.0094(8) -0.0036(7)
C6 0.0306(8) 0.0315(8) 0.0307(9) -0.0023(6) 0.0026(6) 0.0006(6)
C7 0.0326(8) 0.0329(8) 0.0292(9) -0.0030(7) 0.0021(6) 0.0018(6)
C8 0.0314(8) 0.0306(8) 0.0267(8) -0.0001(6) 0.0058(6) 0.0022(6)
C9 0.0463(10) 0.0592(12) 0.0397(10) 0.0116(9) 0.0063(8) -0.0125(8)
C10 0.0371(9) 0.0549(11) 0.0354(10) -0.0046(9) 0.0131(7) -0.0077(8)
C11 0.0308(8) 0.0338(8) 0.0313(9) -0.0035(7) 0.0046(6) 0.0023(6)
C12 0.0387(9) 0.0318(8) 0.0285(9) -0.0020(6) 0.0059(7) -0.0029(6)
C13 0.0389(9) 0.0323(8) 0.0345(9) -0.0081(7) 0.0097(7) -0.0025(6)
C14 0.0467(10) 0.0452(10) 0.0390(10) -0.0086(8) 0.0015(8) -0.0085(8)
N1 0.0315(7) 0.0316(7) 0.0303(7) -0.0059(6) 0.0090(5) -0.0032(5)
O1 0.0665(8) 0.0484(8) 0.0353(7) -0.0148(6) 0.0154(6) -0.0096(6)
O2 0.0385(6) 0.0398(6) 0.0370(7) 0.0098(5) 0.0039(5) 0.0039(5)
O3 0.0330(6) 0.0389(6) 0.0324(6) -0.0055(5) 0.0052(5) -0.0062(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 N1 1.384(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.403(2) . ?
C2 C3 1.377(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.443(2) . ?
C7 O1 1.2182(19) . ?
C7 C8 1.546(2) . ?
C8 O2 1.4159(18) . ?
C8 N1 1.452(2) . ?
C8 C11 1.543(2) . ?
C9 O2 1.440(2) . ?
C9 C10 1.512(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.507(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O3 1.4209(18) . ?
C11 H11 0.9800 . ?
C12 O3 1.4340(19) . ?
C12 C13 1.508(2) . ?
C12 C14 1.508(2) . ?
C12 H12 0.9800 . ?
C13 N1 1.4567(19) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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

N1 C1 C2 128.50(14) . . ?
N1 C1 C6 111.61(14) . . ?
C2 C1 C6 119.86(14) . . ?
C3 C2 C1 117.69(16) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 122.71(17) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C5 C4 C3 119.59(16) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 118.83(16) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 121.15(15) . . ?
C5 C6 C7 131.49(15) . . ?
C1 C6 C7 107.36(13) . . ?
O1 C7 C6 130.27(15) . . ?
O1 C7 C8 123.06(15) . . ?
C6 C7 C8 106.66(13) . . ?
O2 C8 N1 111.59(12) . . ?
O2 C8 C11 105.89(12) . . ?
N1 C8 C11 113.36(12) . . ?
O2 C8 C7 111.37(12) . . ?
N1 C8 C7 103.18(12) . . ?
C11 C8 C7 111.61(12) . . ?
O2 C9 C10 106.12(14) . . ?
O2 C9 H9A 110.5 . . ?
C10 C9 H9A 110.5 . . ?
O2 C9 H9B 110.5 . . ?
C10 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
C11 C10 C9 102.66(13) . . ?
C11 C10 H10A 111.2 . . ?
C9 C10 H10A 111.2 . . ?
C11 C10 H10B 111.2 . . ?
C9 C10 H10B 111.2 . . ?
H10A C10 H10B 109.1 . . ?
O3 C11 C10 107.62(13) . . ?
O3 C11 C8 111.71(12) . . ?
C10 C11 C8 101.47(12) . . ?
O3 C11 H11 111.8 . . ?
C10 C11 H11 111.8 . . ?
C8 C11 H11 111.8 . . ?
O3 C12 C13 107.88(13) . . ?
O3 C12 C14 107.74(12) . . ?
C13 C12 C14 113.22(13) . . ?
O3 C12 H12 109.3 . . ?
C13 C12 H12 109.3 . . ?
C14 C12 H12 109.3 . . ?
N1 C13 C12 110.21(12) . . ?
N1 C13 H13A 109.6 . . ?
C12 C13 H13A 109.6 . . ?
N1 C13 H13B 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 C8 109.09(12) . . ?
C1 N1 C13 122.69(13) . . ?
C8 N1 C13 117.05(12) . . ?
C8 O2 C9 110.03(12) . . ?
C11 O3 C12 113.84(11) . . ?

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

N1 C1 C2 C3 174.22(14) . . . . ?
C6 C1 C2 C3 -3.7(2) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C5 2.4(3) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C4 C5 C6 C1 -2.0(2) . . . . ?
C4 C5 C6 C7 177.99(16) . . . . ?
N1 C1 C6 C5 -173.54(14) . . . . ?
C2 C1 C6 C5 4.7(2) . . . . ?
N1 C1 C6 C7 6.44(16) . . . . ?
C2 C1 C6 C7 -175.30(13) . . . . ?
C5 C6 C7 O1 3.1(3) . . . . ?
C1 C6 C7 O1 -176.89(16) . . . . ?
C5 C6 C7 C8 -177.07(16) . . . . ?
C1 C6 C7 C8 2.96(15) . . . . ?
O1 C7 C8 O2 49.51(19) . . . . ?
C6 C7 C8 O2 -130.35(13) . . . . ?
O1 C7 C8 N1 169.34(14) . . . . ?
C6 C7 C8 N1 -10.52(14) . . . . ?
O1 C7 C8 C11 -68.60(19) . . . . ?
C6 C7 C8 C11 111.54(14) . . . . ?
O2 C9 C10 C11 -29.95(18) . . . . ?
C9 C10 C11 O3 -81.05(15) . . . . ?
C9 C10 C11 C8 36.37(16) . . . . ?
O2 C8 C11 O3 83.17(15) . . . . ?
N1 C8 C11 O3 -39.49(17) . . . . ?
C7 C8 C11 O3 -155.48(13) . . . . ?
O2 C8 C11 C10 -31.24(15) . . . . ?
N1 C8 C11 C10 -153.90(13) . . . . ?
C7 C8 C11 C10 90.11(15) . . . . ?
O3 C12 C13 N1 58.57(16) . . . . ?
C14 C12 C13 N1 177.70(14) . . . . ?
C2 C1 N1 C8 168.12(14) . . . . ?
C6 C1 N1 C8 -13.80(16) . . . . ?
C2 C1 N1 C13 25.6(2) . . . . ?
C6 C1 N1 C13 -156.36(13) . . . . ?
O2 C8 N1 C1 134.18(12) . . . . ?
C11 C8 N1 C1 -106.37(14) . . . . ?
C7 C8 N1 C1 14.50(15) . . . . ?
O2 C8 N1 C13 -80.89(15) . . . . ?
C11 C8 N1 C13 38.57(17) . . . . ?
C7 C8 N1 C13 159.44(12) . . . . ?
C12 C13 N1 C1 91.39(17) . . . . ?
C12 C13 N1 C8 -48.43(17) . . . . ?
N1 C8 O2 C9 136.98(14) . . . . ?
C11 C8 O2 C9 13.20(16) . . . . ?
C7 C8 O2 C9 -108.30(14) . . . . ?
C10 C9 O2 C8 10.40(19) . . . . ?
C10 C11 O3 C12 165.10(12) . . . . ?
C8 C11 O3 C12 54.55(16) . . . . ?
C13 C12 O3 C11 -64.46(15) . . . . ?
C14 C12 O3 C11 172.98(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.932

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_full 0.965

_refine_diff_density_max         0.216

_refine_diff_density_min         -0.191

_refine_diff_density_rms         0.042