# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2009



data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Steven Bull'
'Phil Axe'
'Matt Cheeseman'
'Iwan R. Davies'
'Andrew L. Johnson'

_publ_contact_author_name        'Steven Bull'
_publ_contact_author_email       S.D.BULL@BATH.AC.UK

_publ_section_title              
;
A temporary stereocentre approach for the asymmetric
synthesis of chiral cyclopropane-carboxaldehydes
;

# Attachment 'X-ray_file.CIF'

data_compound4d
_database_code_depnum_ccdc_archive 'CCDC 257652'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'Compound 4d'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H28 N2 O6'
_chemical_formula_weight         452.49
_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           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   7.67000(10)
_cell_length_b                   14.8370(3)
_cell_length_c                   20.5190(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2335.06(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    32654
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9863
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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  KappaCCD
_diffrn_measurement_method       KappaCCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            43530
_diffrn_reflns_av_R_equivalents  0.1280
_diffrn_reflns_av_sigmaI/netI    0.0605
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.59
_diffrn_reflns_theta_max         27.46
_reflns_number_total             5310
_reflns_number_gt                4314
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'Collect, Nonius program suite version 1.9 (1997)'
_computing_cell_refinement       
'Collect, Nonius program suite version 1.9 (1997)'
_computing_data_reduction        
'Denzo and Scalepack (otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. 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^)+(0.0541P)^2^+0.0878P] 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     SHELXL
_refine_ls_extinction_coef       0.035(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(8)
_refine_ls_number_reflns         5310
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0998
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
O1 O 0.71988(17) 0.32131(8) 0.19098(6) 0.0372(3) Uani 1 1 d . . .
O2 O 0.76207(17) 0.46311(8) 0.15678(6) 0.0365(3) Uani 1 1 d . . .
O3 O 0.26636(15) 0.35543(7) 0.07870(5) 0.0303(3) Uani 1 1 d . . .
O4 O 0.52002(15) 0.21416(8) 0.00653(6) 0.0311(3) Uani 1 1 d . . .
H4 H 0.5277 0.1651 -0.0137 0.037 Uiso 1 1 calc R . .
O5 O 1.04367(17) 0.10080(9) 0.23748(7) 0.0390(3) Uani 1 1 d . . .
O6 O 1.19553(16) -0.01195(9) 0.20039(7) 0.0426(3) Uani 1 1 d . . .
N1 N 0.52220(18) 0.39460(9) 0.12208(7) 0.0278(3) Uani 1 1 d . . .
N2 N 1.05650(18) 0.02373(10) 0.21654(7) 0.0307(3) Uani 1 1 d . . .
C1 C 0.6726(2) 0.38553(12) 0.15996(9) 0.0317(4) Uani 1 1 d . . .
C2 C 0.6883(2) 0.52210(11) 0.10544(9) 0.0323(4) Uani 1 1 d . . .
C3 C 0.7866(3) 0.50062(13) 0.04338(10) 0.0429(5) Uani 1 1 d . . .
H3A H 0.9118 0.5091 0.0506 0.064 Uiso 1 1 calc R . .
H3B H 0.7474 0.5409 0.0085 0.064 Uiso 1 1 calc R . .
H3C H 0.7643 0.4379 0.0309 0.064 Uiso 1 1 calc R . .
C4 C 0.7163(3) 0.61817(11) 0.12760(10) 0.0389(4) Uani 1 1 d . . .
H4A H 0.6592 0.6273 0.1698 0.058 Uiso 1 1 calc R . .
H4B H 0.6664 0.6596 0.0954 0.058 Uiso 1 1 calc R . .
H4C H 0.8416 0.6298 0.1319 0.058 Uiso 1 1 calc R . .
C5 C 0.4984(2) 0.48883(11) 0.10143(8) 0.0285(4) Uani 1 1 d . . .
H5 H 0.4597 0.4899 0.0549 0.034 Uiso 1 1 calc R . .
C6 C 0.3605(2) 0.53629(12) 0.14361(8) 0.0322(4) Uani 1 1 d . . .
H6A H 0.2659 0.4929 0.1533 0.039 Uiso 1 1 calc R . .
H6B H 0.4147 0.5538 0.1855 0.039 Uiso 1 1 calc R . .
C7 C 0.2817(2) 0.61912(11) 0.11269(9) 0.0315(4) Uani 1 1 d . . .
C8 C 0.2607(3) 0.69806(12) 0.14825(10) 0.0411(5) Uani 1 1 d . . .
H8 H 0.3017 0.7008 0.1919 0.049 Uiso 1 1 calc R . .
C9 C 0.1804(3) 0.77321(14) 0.12075(14) 0.0539(6) Uani 1 1 d . . .
H9 H 0.1678 0.8268 0.1456 0.065 Uiso 1 1 calc R . .
C10 C 0.1192(3) 0.77025(15) 0.05758(14) 0.0559(6) Uani 1 1 d . . .
H10 H 0.0651 0.8217 0.0389 0.067 Uiso 1 1 calc R . .
C11 C 0.1370(3) 0.69189(15) 0.02164(12) 0.0494(5) Uani 1 1 d . . .
H11 H 0.0936 0.6891 -0.0217 0.059 Uiso 1 1 calc R . .
C12 C 0.2186(2) 0.61721(13) 0.04904(10) 0.0377(4) Uani 1 1 d . . .
H12 H 0.2315 0.5639 0.0239 0.045 Uiso 1 1 calc R . .
C13 C 0.3987(2) 0.32940(11) 0.10553(8) 0.0261(4) Uani 1 1 d . . .
C14 C 0.4407(2) 0.23149(11) 0.11794(8) 0.0250(3) Uani 1 1 d . . .
H14 H 0.4836 0.2249 0.1637 0.030 Uiso 1 1 calc R . .
C15 C 0.2772(2) 0.17406(11) 0.10942(8) 0.0293(4) Uani 1 1 d . . .
H15A H 0.1837 0.1979 0.1370 0.044 Uiso 1 1 calc R . .
H15B H 0.3026 0.1117 0.1221 0.044 Uiso 1 1 calc R . .
H15C H 0.2404 0.1756 0.0637 0.044 Uiso 1 1 calc R . .
C16 C 0.5873(2) 0.20338(11) 0.07072(8) 0.0257(3) Uani 1 1 d . . .
H16 H 0.6875 0.2458 0.0764 0.031 Uiso 1 1 calc R . .
C17 C 0.6516(2) 0.10826(11) 0.08267(8) 0.0260(3) Uani 1 1 d . . .
H17 H 0.5708 0.0584 0.0700 0.031 Uiso 1 1 calc R . .
C18 C 0.8434(2) 0.09049(12) 0.07404(9) 0.0300(4) Uani 1 1 d . . .
H18A H 0.9186 0.1417 0.0611 0.036 Uiso 1 1 calc R . .
H18B H 0.8787 0.0314 0.0560 0.036 Uiso 1 1 calc R . .
C19 C 0.7640(2) 0.09214(11) 0.14193(8) 0.0256(3) Uani 1 1 d . . .
H19 H 0.7911 0.1462 0.1692 0.031 Uiso 1 1 calc R . .
C20 C 0.7547(2) 0.00398(10) 0.17705(8) 0.0259(3) Uani 1 1 d . . .
C21 C 0.6086(2) -0.05181(12) 0.17490(9) 0.0331(4) Uani 1 1 d . . .
H21 H 0.5064 -0.0312 0.1534 0.040 Uiso 1 1 calc R . .
C22 C 0.6083(2) -0.13654(13) 0.20323(10) 0.0380(4) Uani 1 1 d . . .
H22 H 0.5062 -0.1727 0.2011 0.046 Uiso 1 1 calc R . .
C23 C 0.7549(2) -0.16915(12) 0.23450(9) 0.0341(4) Uani 1 1 d . . .
H23 H 0.7543 -0.2278 0.2531 0.041 Uiso 1 1 calc R . .
C24 C 0.9020(2) -0.11604(12) 0.23861(8) 0.0308(4) Uani 1 1 d . . .
H24 H 1.0039 -0.1373 0.2600 0.037 Uiso 1 1 calc R . .
C25 C 0.8979(2) -0.03124(11) 0.21098(8) 0.0261(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
O1 0.0391(7) 0.0305(6) 0.0422(7) 0.0029(5) -0.0154(5) 0.0003(6)
O2 0.0356(7) 0.0302(6) 0.0439(7) 0.0026(5) -0.0139(6) -0.0063(6)
O3 0.0291(6) 0.0303(6) 0.0316(6) -0.0006(5) -0.0053(5) 0.0011(5)
O4 0.0329(6) 0.0346(7) 0.0259(6) 0.0030(5) 0.0015(5) 0.0079(5)
O5 0.0438(8) 0.0345(7) 0.0386(7) -0.0011(6) -0.0105(5) -0.0060(6)
O6 0.0248(7) 0.0468(8) 0.0563(9) 0.0161(6) 0.0037(6) 0.0040(6)
N1 0.0294(7) 0.0225(7) 0.0314(8) 0.0006(6) -0.0068(6) -0.0006(6)
N2 0.0274(8) 0.0362(8) 0.0286(8) 0.0086(6) -0.0038(6) -0.0024(6)
C1 0.0317(9) 0.0285(9) 0.0348(10) -0.0022(7) -0.0073(7) -0.0020(7)
C2 0.0334(10) 0.0284(9) 0.0353(9) 0.0015(7) -0.0055(7) -0.0017(7)
C3 0.0363(11) 0.0452(11) 0.0473(11) 0.0000(9) 0.0049(9) -0.0033(9)
C4 0.0392(10) 0.0296(9) 0.0479(11) 0.0010(8) -0.0054(9) -0.0074(8)
C5 0.0323(9) 0.0246(8) 0.0287(9) 0.0016(6) -0.0025(6) -0.0010(7)
C6 0.0371(10) 0.0306(9) 0.0288(9) 0.0009(7) 0.0008(7) -0.0026(8)
C7 0.0268(9) 0.0282(8) 0.0396(10) 0.0003(7) 0.0051(7) -0.0026(7)
C8 0.0407(11) 0.0312(9) 0.0515(12) -0.0062(8) 0.0089(9) -0.0028(8)
C9 0.0453(12) 0.0278(10) 0.0888(19) -0.0030(10) 0.0189(12) 0.0034(9)
C10 0.0418(12) 0.0397(11) 0.0861(19) 0.0184(12) 0.0092(12) 0.0076(10)
C11 0.0394(12) 0.0512(13) 0.0576(14) 0.0145(10) 0.0009(9) 0.0086(10)
C12 0.0349(10) 0.0351(9) 0.0431(11) 0.0023(8) 0.0030(8) 0.0016(8)
C13 0.0270(9) 0.0291(8) 0.0221(8) -0.0018(6) -0.0009(6) -0.0007(7)
C14 0.0239(8) 0.0263(8) 0.0248(8) 0.0020(6) -0.0025(6) 0.0006(7)
C15 0.0273(9) 0.0265(8) 0.0340(9) 0.0010(7) 0.0035(7) -0.0021(7)
C16 0.0234(8) 0.0255(8) 0.0282(8) 0.0035(6) -0.0015(6) -0.0005(6)
C17 0.0225(8) 0.0272(8) 0.0283(9) 0.0021(6) -0.0030(6) -0.0006(7)
C18 0.0268(9) 0.0318(9) 0.0314(9) 0.0054(7) 0.0016(7) 0.0019(7)
C19 0.0227(8) 0.0273(8) 0.0267(8) 0.0004(6) -0.0004(6) -0.0003(7)
C20 0.0242(8) 0.0288(8) 0.0247(8) -0.0007(6) 0.0020(6) 0.0028(7)
C21 0.0257(9) 0.0368(10) 0.0369(10) 0.0065(8) -0.0027(7) -0.0010(8)
C22 0.0333(9) 0.0371(10) 0.0437(11) 0.0077(8) -0.0036(8) -0.0090(8)
C23 0.0376(10) 0.0288(8) 0.0359(9) 0.0088(7) 0.0011(7) -0.0025(8)
C24 0.0298(9) 0.0334(9) 0.0292(9) 0.0059(7) -0.0011(7) 0.0029(7)
C25 0.0225(8) 0.0319(9) 0.0239(8) 0.0015(7) 0.0009(6) -0.0007(7)

_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 C1 1.202(2) . ?
O2 C1 1.342(2) . ?
O2 C2 1.482(2) . ?
O3 C13 1.217(2) . ?
O4 C16 1.423(2) . ?
O4 H4 0.8400 . ?
O5 N2 1.226(2) . ?
O6 N2 1.236(2) . ?
N1 C13 1.396(2) . ?
N1 C1 1.397(2) . ?
N1 C5 1.472(2) . ?
N2 C25 1.469(2) . ?
C2 C4 1.512(2) . ?
C2 C3 1.514(3) . ?
C2 C5 1.540(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.537(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.509(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.389(2) . ?
C7 C12 1.393(3) . ?
C8 C9 1.393(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.510(2) . ?
C14 C15 1.526(2) . ?
C14 C16 1.542(2) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.515(2) . ?
C16 H16 1.0000 . ?
C17 C18 1.505(2) . ?
C17 C19 1.509(2) . ?
C17 H17 1.0000 . ?
C18 C19 1.521(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.495(2) . ?
C19 H19 1.0000 . ?
C20 C21 1.394(2) . ?
C20 C25 1.401(2) . ?
C21 C22 1.385(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.379(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(2) . ?
C24 H24 0.9500 . ?

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
C1 O2 C2 110.23(13) . . ?
C16 O4 H4 109.5 . . ?
C13 N1 C1 128.96(14) . . ?
C13 N1 C5 120.25(13) . . ?
C1 N1 C5 110.73(13) . . ?
O5 N2 O6 124.26(15) . . ?
O5 N2 C25 118.60(14) . . ?
O6 N2 C25 117.13(14) . . ?
O1 C1 O2 123.46(16) . . ?
O1 C1 N1 128.32(16) . . ?
O2 C1 N1 108.22(14) . . ?
O2 C2 C4 106.78(14) . . ?
O2 C2 C3 106.46(15) . . ?
C4 C2 C3 112.38(15) . . ?
O2 C2 C5 102.11(13) . . ?
C4 C2 C5 116.93(15) . . ?
C3 C2 C5 111.02(14) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C6 110.99(14) . . ?
N1 C5 C2 99.88(14) . . ?
C6 C5 C2 118.28(14) . . ?
N1 C5 H5 109.1 . . ?
C6 C5 H5 109.1 . . ?
C2 C5 H5 109.1 . . ?
C7 C6 C5 114.31(14) . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C8 C7 C12 117.99(17) . . ?
C8 C7 C6 120.80(17) . . ?
C12 C7 C6 121.11(15) . . ?
C7 C8 C9 120.9(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.6(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 119.9(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C7 121.25(18) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
O3 C13 N1 117.13(14) . . ?
O3 C13 C14 124.02(14) . . ?
N1 C13 C14 118.75(14) . . ?
C13 C14 C15 110.04(13) . . ?
C13 C14 C16 108.06(13) . . ?
C15 C14 C16 112.10(13) . . ?
C13 C14 H14 108.9 . . ?
C15 C14 H14 108.9 . . ?
C16 C14 H14 108.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 C17 111.87(13) . . ?
O4 C16 C14 106.65(13) . . ?
C17 C16 C14 112.81(13) . . ?
O4 C16 H16 108.5 . . ?
C17 C16 H16 108.5 . . ?
C14 C16 H16 108.5 . . ?
C18 C17 C19 60.59(11) . . ?
C18 C17 C16 117.54(15) . . ?
C19 C17 C16 117.64(14) . . ?
C18 C17 H17 116.5 . . ?
C19 C17 H17 116.5 . . ?
C16 C17 H17 116.5 . . ?
C17 C18 C19 59.85(11) . . ?
C17 C18 H18A 117.8 . . ?
C19 C18 H18A 117.8 . . ?
C17 C18 H18B 117.8 . . ?
C19 C18 H18B 117.8 . . ?
H18A C18 H18B 114.9 . . ?
C20 C19 C17 119.98(14) . . ?
C20 C19 C18 116.53(14) . . ?
C17 C19 C18 59.56(11) . . ?
C20 C19 H19 116.2 . . ?
C17 C19 H19 116.2 . . ?
C18 C19 H19 116.2 . . ?
C21 C20 C25 115.11(14) . . ?
C21 C20 C19 122.86(15) . . ?
C25 C20 C19 121.90(15) . . ?
C22 C21 C20 121.80(16) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C23 C22 C21 120.76(17) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 119.61(15) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 118.48(16) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 H24 120.8 . . ?
C24 C25 C20 124.20(16) . . ?
C24 C25 N2 117.06(15) . . ?
C20 C25 N2 118.72(14) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.073