Supplementary Material (ESI) for Organic & Biomolecular Chemistry
  This journal is (c) The Royal Society of Chemistry 2007



data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        "Peter O'Brien"
_publ_contact_author_address     
;
Department of Chemistry
University of York
Heslington
YORK
YO10 5DD
UNITED KINGDOM
;

_publ_contact_author_email       PAOB1@YORK.AC.UK

_publ_section_title              
;
Stereocontrolled Synthesis and Alkylation of Cyclic
b-Amino Esters: Asymmetric Synthesis of a (-)-Sparteine Surrogate
;
loop_
_publ_author_name
"P O'Brien"
'John Gilday'
'Jean-Paul R. Hermet'
'Matthew J. McGrath'
'Aurelien Viterisi'
;
A.C.Whitwood
;
'Jonathan M. Wright'

data_pob0401m
_database_code_depnum_ccdc_archive 'CCDC 623452'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            
;(2S)-3-phenyl-2-((2S)-1-((1S)-1-phenylethyl)piperidin-2-
yl)propionate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H31 N O2'
_chemical_formula_sum            'C24 H31 N O2'
_chemical_formula_weight         365.50
_chemical_absolute_configuration syn

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)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.7573(6)
_cell_length_b                   6.5351(5)
_cell_length_c                   20.5605(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.341(2)
_cell_angle_gamma                90.00
_cell_volume                     1040.54(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    115(2)
_cell_measurement_reflns_used    2571
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      27.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS V2.03; (Sheldrick)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      115(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            7226
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         0.99
_diffrn_reflns_theta_max         27.55
_reflns_number_total             4564
_reflns_number_gt                4140
_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^)+(0.0328P)^2^+0.2162P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(11)
_refine_ls_number_reflns         4564
_refine_ls_number_parameters     246
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 -0.04208(19) 0.9268(3) 0.77248(7) 0.0234(3) Uani 1 1 d . . .
N1 N 0.25636(15) 1.06173(19) 0.72209(6) 0.0181(3) Uani 1 1 d . . .
O1 O -0.14917(14) 1.0585(2) 0.76348(6) 0.0330(3) Uani 1 1 d . . .
C2 C 0.11541(19) 0.9392(2) 0.81914(7) 0.0206(3) Uani 1 1 d . . .
H2 H 0.1163 1.0754 0.8414 0.025 Uiso 1 1 calc R . .
O2 O -0.04680(13) 0.74537(19) 0.74192(5) 0.0281(3) Uani 1 1 d . . .
C3 C 0.27722(18) 0.9227(2) 0.77891(7) 0.0188(3) Uani 1 1 d . . .
H3 H 0.2799 0.7800 0.7614 0.023 Uiso 1 1 calc R . .
C4 C 0.44778(19) 0.9565(2) 0.81881(7) 0.0224(3) Uani 1 1 d . . .
H4A H 0.4502 0.8683 0.8580 0.027 Uiso 1 1 calc R . .
H4B H 0.5447 0.9149 0.7925 0.027 Uiso 1 1 calc R . .
C5 C 0.4731(2) 1.1778(3) 0.83979(8) 0.0271(3) Uani 1 1 d . . .
H5A H 0.5906 1.1955 0.8605 0.033 Uiso 1 1 calc R . .
H5B H 0.3887 1.2130 0.8724 0.033 Uiso 1 1 calc R . .
C6 C 0.4489(2) 1.3214(2) 0.78129(8) 0.0262(3) Uani 1 1 d . . .
H6A H 0.5453 1.3029 0.7524 0.031 Uiso 1 1 calc R . .
H6B H 0.4503 1.4651 0.7965 0.031 Uiso 1 1 calc R . .
C7 C 0.27732(19) 1.2770(2) 0.74330(7) 0.0212(3) Uani 1 1 d . . .
H7A H 0.1815 1.3128 0.7710 0.025 Uiso 1 1 calc R . .
H7B H 0.2680 1.3663 0.7044 0.025 Uiso 1 1 calc R . .
C8 C 0.37025(19) 1.0105(2) 0.66923(7) 0.0197(3) Uani 1 1 d . . .
H8 H 0.4928 1.0344 0.6852 0.024 Uiso 1 1 calc R . .
C9 C 0.3509(2) 0.7870(2) 0.64747(7) 0.0255(3) Uani 1 1 d . . .
H9A H 0.2282 0.7550 0.6389 0.038 Uiso 1 1 calc R . .
H9B H 0.3999 0.6971 0.6819 0.038 Uiso 1 1 calc R . .
H9C H 0.4121 0.7660 0.6076 0.038 Uiso 1 1 calc R . .
C10 C 0.11533(19) 0.7697(3) 0.87128(7) 0.0258(3) Uani 1 1 d . . .
H10A H 0.1318 0.6359 0.8499 0.031 Uiso 1 1 calc R . .
H10B H 0.2148 0.7916 0.9029 0.031 Uiso 1 1 calc R . .
C11 C -0.04770(19) 0.7607(3) 0.90800(7) 0.0229(3) Uani 1 1 d . . .
C12 C -0.1658(2) 0.6036(3) 0.89784(7) 0.0276(3) Uani 1 1 d . . .
H12 H -0.1460 0.5010 0.8664 0.033 Uiso 1 1 calc R . .
C13 C -0.3131(2) 0.5942(3) 0.93308(8) 0.0303(4) Uani 1 1 d . . .
H13 H -0.3929 0.4853 0.9256 0.036 Uiso 1 1 calc R . .
C14 C -0.3438(2) 0.7417(3) 0.97864(7) 0.0299(4) Uani 1 1 d . . .
H14 H -0.4442 0.7345 1.0029 0.036 Uiso 1 1 calc R . .
C15 C -0.2281(2) 0.9001(3) 0.98895(8) 0.0334(4) Uani 1 1 d . . .
H15 H -0.2494 1.0030 1.0201 0.040 Uiso 1 1 calc R . .
C16 C -0.0805(2) 0.9097(3) 0.95395(8) 0.0298(4) Uani 1 1 d . . .
H16 H -0.0013 1.0192 0.9615 0.036 Uiso 1 1 calc R . .
C17 C 0.3291(2) 1.1479(2) 0.61091(7) 0.0222(3) Uani 1 1 d . . .
C18 C 0.4598(2) 1.2580(3) 0.58389(7) 0.0261(3) Uani 1 1 d . . .
H18 H 0.5738 1.2516 0.6034 0.031 Uiso 1 1 calc R . .
C19 C 0.4269(3) 1.3772(3) 0.52891(8) 0.0333(4) Uani 1 1 d . . .
H19 H 0.5181 1.4514 0.5109 0.040 Uiso 1 1 calc R . .
C20 C 0.2629(3) 1.3883(3) 0.50042(8) 0.0400(5) Uani 1 1 d . . .
H20 H 0.2404 1.4699 0.4627 0.048 Uiso 1 1 calc R . .
C21 C 0.1302(3) 1.2802(3) 0.52681(9) 0.0409(5) Uani 1 1 d . . .
H21 H 0.0164 1.2879 0.5072 0.049 Uiso 1 1 calc R . .
C22 C 0.1634(2) 1.1602(3) 0.58207(8) 0.0316(4) Uani 1 1 d . . .
H22 H 0.0721 1.0864 0.6001 0.038 Uiso 1 1 calc R . .
C23 C -0.1838(2) 0.7192(3) 0.69171(9) 0.0394(4) Uani 1 1 d . . .
H23A H -0.1899 0.8397 0.6625 0.047 Uiso 1 1 calc R . .
H23B H -0.2963 0.7040 0.7116 0.047 Uiso 1 1 calc R . .
C24 C -0.1435(3) 0.5306(3) 0.65414(10) 0.0463(5) Uani 1 1 d . . .
H24A H -0.1453 0.4112 0.6829 0.069 Uiso 1 1 calc R . .
H24B H -0.0287 0.5440 0.6370 0.069 Uiso 1 1 calc R . .
H24C H -0.2300 0.5133 0.6179 0.069 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
C1 0.0192(7) 0.0295(9) 0.0225(7) 0.0062(7) 0.0079(6) -0.0006(6)
N1 0.0211(6) 0.0168(6) 0.0167(6) 0.0012(5) 0.0037(5) 0.0009(5)
O1 0.0226(6) 0.0363(7) 0.0403(7) 0.0063(6) 0.0043(5) 0.0067(5)
C2 0.0222(7) 0.0201(8) 0.0198(7) 0.0025(6) 0.0042(6) 0.0005(6)
O2 0.0228(5) 0.0313(6) 0.0299(6) -0.0016(5) -0.0011(4) -0.0009(5)
C3 0.0203(7) 0.0169(7) 0.0193(7) 0.0014(6) 0.0026(5) 0.0008(6)
C4 0.0199(7) 0.0258(8) 0.0216(7) 0.0040(6) 0.0008(6) 0.0008(6)
C5 0.0254(8) 0.0327(9) 0.0229(7) -0.0042(7) -0.0015(6) -0.0014(7)
C6 0.0308(8) 0.0203(8) 0.0278(8) -0.0055(6) 0.0039(7) -0.0038(6)
C7 0.0268(7) 0.0166(7) 0.0207(7) 0.0011(6) 0.0047(6) 0.0023(6)
C8 0.0200(7) 0.0199(8) 0.0196(7) -0.0009(6) 0.0042(5) -0.0018(6)
C9 0.0327(8) 0.0202(8) 0.0242(7) -0.0020(6) 0.0066(6) -0.0024(6)
C10 0.0257(8) 0.0291(9) 0.0230(7) 0.0073(7) 0.0062(6) 0.0015(7)
C11 0.0244(7) 0.0274(8) 0.0171(6) 0.0055(6) 0.0033(5) -0.0003(7)
C12 0.0365(9) 0.0249(9) 0.0220(7) -0.0017(6) 0.0057(7) -0.0028(7)
C13 0.0317(8) 0.0338(9) 0.0258(8) 0.0011(7) 0.0038(6) -0.0108(7)
C14 0.0238(8) 0.0441(10) 0.0221(7) 0.0011(7) 0.0042(6) -0.0031(7)
C15 0.0355(9) 0.0389(10) 0.0263(8) -0.0094(8) 0.0071(7) -0.0015(8)
C16 0.0308(9) 0.0323(9) 0.0266(8) -0.0043(7) 0.0039(7) -0.0085(7)
C17 0.0310(8) 0.0176(7) 0.0184(7) -0.0027(6) 0.0047(6) -0.0010(6)
C18 0.0348(8) 0.0206(8) 0.0236(7) -0.0033(7) 0.0085(6) -0.0027(7)
C19 0.0538(11) 0.0227(9) 0.0247(8) 0.0001(7) 0.0145(8) -0.0043(8)
C20 0.0705(14) 0.0292(10) 0.0205(8) 0.0045(7) 0.0045(8) 0.0026(9)
C21 0.0466(11) 0.0447(12) 0.0302(9) 0.0027(9) -0.0082(8) 0.0026(9)
C22 0.0339(9) 0.0341(10) 0.0266(8) 0.0044(7) -0.0002(7) -0.0042(7)
C23 0.0269(9) 0.0492(13) 0.0410(10) -0.0009(9) -0.0074(7) -0.0043(8)
C24 0.0410(11) 0.0511(13) 0.0455(11) -0.0082(10) -0.0089(9) -0.0131(9)

_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 O1 1.2032(19) . ?
C1 O2 1.341(2) . ?
C1 C2 1.511(2) . ?
N1 C8 1.4783(18) . ?
N1 C7 1.4787(19) . ?
N1 C3 1.4812(17) . ?
C2 C10 1.542(2) . ?
C2 C3 1.5469(19) . ?
C2 H2 1.0000 . ?
O2 C23 1.448(2) . ?
C3 C4 1.532(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.519(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.529(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.531(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C17 1.517(2) . ?
C8 C9 1.532(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.511(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.384(2) . ?
C11 C16 1.391(2) . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.374(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.386(2) . ?
C17 C18 1.386(2) . ?
C18 C19 1.384(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.371(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.392(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.497(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 124.11(15) . . ?
O1 C1 C2 125.77(15) . . ?
O2 C1 C2 110.12(13) . . ?
C8 N1 C7 111.84(11) . . ?
C8 N1 C3 113.48(11) . . ?
C7 N1 C3 110.22(11) . . ?
C1 C2 C10 111.71(13) . . ?
C1 C2 C3 107.93(11) . . ?
C10 C2 C3 110.79(12) . . ?
C1 C2 H2 108.8 . . ?
C10 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C1 O2 C23 115.93(13) . . ?
N1 C3 C4 112.67(12) . . ?
N1 C3 C2 108.92(11) . . ?
C4 C3 C2 113.96(11) . . ?
N1 C3 H3 107.0 . . ?
C4 C3 H3 107.0 . . ?
C2 C3 H3 107.0 . . ?
C5 C4 C3 112.50(13) . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C4 C5 C6 110.69(13) . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 C7 110.38(13) . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
N1 C7 C6 114.10(12) . . ?
N1 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 C17 109.87(12) . . ?
N1 C8 C9 112.19(12) . . ?
C17 C8 C9 108.71(12) . . ?
N1 C8 H8 108.7 . . ?
C17 C8 H8 108.7 . . ?
C9 C8 H8 108.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C2 114.18(13) . . ?
C11 C10 H10A 108.7 . . ?
C2 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C2 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C16 118.45(14) . . ?
C12 C11 C10 121.30(14) . . ?
C16 C11 C10 120.24(15) . . ?
C11 C12 C13 120.75(15) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 120.32(16) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.63(15) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.23(16) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.61(16) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C22 C17 C18 118.70(15) . . ?
C22 C17 C8 121.32(14) . . ?
C18 C17 C8 119.94(14) . . ?
C19 C18 C17 121.02(16) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 120.05(16) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 119.88(17) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 120.03(18) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 120.33(17) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
O2 C23 C24 107.37(15) . . ?
O2 C23 H23A 110.2 . . ?
C24 C23 H23A 110.2 . . ?
O2 C23 H23B 110.2 . . ?
C24 C23 H23B 110.2 . . ?
H23A C23 H23B 108.5 . . ?
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 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C10 119.98(16) . . . . ?
O2 C1 C2 C10 -59.87(16) . . . . ?
O1 C1 C2 C3 -117.99(16) . . . . ?
O2 C1 C2 C3 62.16(15) . . . . ?
O1 C1 O2 C23 5.0(2) . . . . ?
C2 C1 O2 C23 -175.10(13) . . . . ?
C8 N1 C3 C4 71.99(15) . . . . ?
C7 N1 C3 C4 -54.33(15) . . . . ?
C8 N1 C3 C2 -160.55(12) . . . . ?
C7 N1 C3 C2 73.14(14) . . . . ?
C1 C2 C3 N1 46.91(16) . . . . ?
C10 C2 C3 N1 169.51(12) . . . . ?
C1 C2 C3 C4 173.64(13) . . . . ?
C10 C2 C3 C4 -63.76(17) . . . . ?
N1 C3 C4 C5 54.01(16) . . . . ?
C2 C3 C4 C5 -70.75(17) . . . . ?
C3 C4 C5 C6 -52.11(17) . . . . ?
C4 C5 C6 C7 51.77(17) . . . . ?
C8 N1 C7 C6 -71.22(15) . . . . ?
C3 N1 C7 C6 56.01(15) . . . . ?
C5 C6 C7 N1 -55.25(16) . . . . ?
C7 N1 C8 C17 -59.60(15) . . . . ?
C3 N1 C8 C17 174.95(12) . . . . ?
C7 N1 C8 C9 179.35(12) . . . . ?
C3 N1 C8 C9 53.90(16) . . . . ?
C1 C2 C10 C11 -53.38(18) . . . . ?
C3 C2 C10 C11 -173.75(13) . . . . ?
C2 C10 C11 C12 108.12(17) . . . . ?
C2 C10 C11 C16 -73.05(19) . . . . ?
C16 C11 C12 C13 -0.5(2) . . . . ?
C10 C11 C12 C13 178.37(15) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C11 0.2(3) . . . . ?
C12 C11 C16 C15 0.3(2) . . . . ?
C10 C11 C16 C15 -178.55(15) . . . . ?
N1 C8 C17 C22 -55.58(18) . . . . ?
C9 C8 C17 C22 67.55(18) . . . . ?
N1 C8 C17 C18 126.98(15) . . . . ?
C9 C8 C17 C18 -109.90(16) . . . . ?
C22 C17 C18 C19 -0.4(2) . . . . ?
C8 C17 C18 C19 177.07(14) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C18 C17 C22 C21 0.4(3) . . . . ?
C8 C17 C22 C21 -177.09(16) . . . . ?
C20 C21 C22 C17 -0.1(3) . . . . ?
C1 O2 C23 C24 167.49(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.033