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



data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Xiaoming Feng'
_publ_contact_author_email       XMFENG@SCU.EDU.CN

_publ_section_title              
;
Chiral Biphenylamide Derivative: Efficient
Organocatalyst for the Enantioselective Synthesis of ?-Hydroxy Phosphonates
;
loop_
_publ_author_name
'Xiaoming Feng'
'Xiaohong Chen'
'Yonghai Hui'
'Jun Jiang'
'Lili Lin'
;
Xiaohua Liu
;
'Jun Wang'

# Attachment 'CD4.CIF'

data_cd4
_database_code_depnum_ccdc_archive 'CCDC 738508'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H30 N4 O4'
_chemical_formula_weight         438.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   8.771(3)
_cell_length_b                   9.743(3)
_cell_length_c                   26.204(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2239.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    29
_cell_measurement_theta_min      4.41
_cell_measurement_theta_max      5.34

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9718
_exptl_absorpt_correction_T_max  0.9761

_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  CAD4
_diffrn_measurement_method       Omega/2-Theta
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 300
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0.182
_diffrn_reflns_number            2417
_diffrn_reflns_av_R_equivalents  0.0070
_diffrn_reflns_av_sigmaI/netI    0.1071
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         25.49
_reflns_number_total             2391
_reflns_number_gt                977
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'DIFRAC (E.J.Gabe,1993)'
_computing_cell_refinement       'DIFRAC (E.J.Gabe,1993)'
_computing_data_reduction        'NRCVAX (E.J.Gabe,1989)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L.J. Farrugia,1997)'
_computing_publication_material  'SHELXL-97 (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 w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_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(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2391
_refine_ls_number_parameters     303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1969
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1402
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -1.0828(6) -0.8775(5) -0.86178(16) 0.0764(15) Uani 1 d . . .
O2 O -0.4248(6) -1.0307(5) -0.96716(18) 0.0849(17) Uani 1 d . . .
O3 O -0.9797(6) -1.2276(4) -0.89813(14) 0.0681(15) Uani 1 d . . .
O4 O -0.6551(5) -0.9333(4) -0.70284(15) 0.0621(13) Uani 1 d . . .
N1 N -0.6176(6) -1.0828(5) -0.91191(17) 0.0538(15) Uani 1 d . . .
H1 H -0.6432 -1.1424 -0.8893 0.065 Uiso 1 calc R . .
N2 N -0.5196(7) -1.3340(6) -0.8937(2) 0.0689(18) Uani 1 d . . .
N3 N -0.7316(6) -0.9175(4) -0.78527(16) 0.0456(13) Uani 1 d . . .
H3 H -0.7273 -0.8642 -0.8114 0.055 Uiso 1 calc R . .
N4 N -0.5984(8) -0.6780(6) -0.8004(2) 0.0624(18) Uani 1 d . . .
C1 C -0.8457(8) -0.9717(6) -0.8848(2) 0.0453(16) Uani 1 d . . .
C2 C -0.9574(10) -0.8709(7) -0.8924(2) 0.061(2) Uani 1 d . . .
C3 C -0.9355(10) -0.7666(7) -0.9284(2) 0.070(2) Uani 1 d . . .
H3A H -1.0076 -0.6975 -0.9325 0.084 Uiso 1 calc R . .
C4 C -0.8058(10) -0.7683(7) -0.9575(2) 0.071(2) Uani 1 d G . .
H4 H -0.7911 -0.6995 -0.9816 0.085 Uiso 1 calc R . .
C5 C -0.6967(9) -0.8683(7) -0.9522(2) 0.066(2) Uani 1 d . . .
H5 H -0.6092 -0.8665 -0.9722 0.080 Uiso 1 calc R . .
C6 C -0.7182(8) -0.9712(6) -0.9170(2) 0.0495(17) Uani 1 d . . .
C7 C -1.2195(9) -0.8124(9) -0.8776(3) 0.107(3) Uani 1 d . . .
H7A H -1.2047 -0.7147 -0.8782 0.161 Uiso 1 calc R . .
H7B H -1.3000 -0.8347 -0.8542 0.161 Uiso 1 calc R . .
H7C H -1.2463 -0.8436 -0.9112 0.161 Uiso 1 calc R . .
C8 C -0.4871(8) -1.1107(7) -0.9371(2) 0.0586(19) Uani 1 d . . .
C9 C -0.4202(8) -1.2515(7) -0.9266(2) 0.0608(18) Uani 1 d . . .
H9 H -0.3216 -1.2399 -0.9095 0.073 Uiso 1 calc R . .
C10 C -0.3963(11) -1.3351(7) -0.9748(3) 0.089(3) Uani 1 d . . .
H10A H -0.4025 -1.2770 -1.0048 0.107 Uiso 1 calc R . .
H10B H -0.2976 -1.3800 -0.9744 0.107 Uiso 1 calc R . .
C11 C -0.5182(12) -1.4355(11) -0.9748(3) 0.155(5) Uani 1 d . . .
H11A H -0.4820 -1.5214 -0.9890 0.186 Uiso 1 calc R . .
H11B H -0.6024 -1.4031 -0.9956 0.186 Uiso 1 calc R . .
C12 C -0.5690(11) -1.4563(7) -0.9224(3) 0.095(3) Uani 1 d . . .
H12A H -0.5233 -1.5385 -0.9082 0.114 Uiso 1 calc R . .
H12B H -0.6790 -1.4656 -0.9211 0.114 Uiso 1 calc R . .
C13 C -0.8668(7) -1.0708(5) -0.84214(19) 0.0413(15) Uani 1 d . . .
C14 C -0.9385(7) -1.1964(6) -0.8491(2) 0.0491(16) Uani 1 d . . .
C15 C -0.9712(7) -1.2841(6) -0.8083(2) 0.0507(17) Uani 1 d . . .
H15 H -1.0229 -1.3662 -0.8137 0.061 Uiso 1 calc R . .
C16 C -0.9261(7) -1.2470(6) -0.7609(2) 0.0539(18) Uani 1 d . . .
H16 H -0.9484 -1.3046 -0.7336 0.065 Uiso 1 calc R . .
C17 C -0.8484(7) -1.1271(6) -0.7517(2) 0.0509(17) Uani 1 d . . .
H17 H -0.8183 -1.1041 -0.7188 0.061 Uiso 1 calc R . .
C18 C -0.8154(7) -1.0404(6) -0.7925(2) 0.0463(16) Uani 1 d . . .
C19 C -1.0206(9) -1.3683(7) -0.9088(3) 0.084(2) Uani 1 d . . .
H19A H -0.9395 -1.4279 -0.8980 0.126 Uiso 1 calc R . .
H19B H -1.0374 -1.3793 -0.9447 0.126 Uiso 1 calc R . .
H19C H -1.1121 -1.3913 -0.8906 0.126 Uiso 1 calc R . .
C20 C -0.6585(7) -0.8723(6) -0.7440(2) 0.0461(16) Uani 1 d . . .
C21 C -0.5732(7) -0.7378(6) -0.7505(2) 0.0531(17) Uani 1 d . . .
H21 H -0.4639 -0.7547 -0.7461 0.064 Uiso 1 calc R . .
C22 C -0.6261(8) -0.6317(6) -0.7105(2) 0.065(2) Uani 1 d . . .
H22A H -0.6803 -0.6764 -0.6828 0.078 Uiso 1 calc R . .
H22B H -0.5395 -0.5825 -0.6964 0.078 Uiso 1 calc R . .
C23 C -0.7288(8) -0.5364(6) -0.7385(2) 0.067(2) Uani 1 d . . .
H23A H -0.6950 -0.4423 -0.7343 0.080 Uiso 1 calc R . .
H23B H -0.8323 -0.5440 -0.7258 0.080 Uiso 1 calc R . .
C24 C -0.7222(9) -0.5773(7) -0.7945(2) 0.071(2) Uani 1 d . . .
H24A H -0.8185 -0.6173 -0.8049 0.086 Uiso 1 calc R . .
H24B H -0.7026 -0.4973 -0.8155 0.086 Uiso 1 calc R . .
HN2 H -0.481(8) -1.354(7) -0.860(3) 0.12(3) Uiso 1 d . . .
HN4 H -0.519(8) -0.644(8) -0.810(3) 0.09(3) Uiso 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 0.089(4) 0.089(4) 0.051(3) 0.012(2) 0.011(3) 0.037(3)
O2 0.088(4) 0.078(3) 0.089(4) 0.008(3) 0.037(3) -0.013(3)
O3 0.100(4) 0.054(3) 0.050(3) -0.002(2) -0.011(3) -0.024(3)
O4 0.083(3) 0.053(2) 0.050(3) 0.008(2) -0.027(2) -0.004(3)
N1 0.054(4) 0.062(4) 0.046(3) 0.016(3) 0.006(3) -0.003(3)
N2 0.101(5) 0.073(4) 0.033(3) 0.000(3) -0.005(3) 0.001(4)
N3 0.058(4) 0.036(3) 0.043(3) 0.007(2) -0.006(3) -0.004(3)
N4 0.070(5) 0.056(4) 0.061(4) 0.002(3) 0.017(4) -0.010(4)
C1 0.065(5) 0.034(3) 0.037(3) 0.003(3) -0.003(3) -0.002(4)
C2 0.084(6) 0.047(4) 0.053(4) -0.002(4) -0.012(4) 0.002(5)
C3 0.111(7) 0.050(4) 0.047(4) 0.008(4) -0.018(4) 0.011(5)
C4 0.112(7) 0.045(4) 0.055(4) 0.017(4) -0.009(4) -0.012(5)
C5 0.087(6) 0.065(4) 0.047(4) 0.021(4) 0.000(4) -0.006(5)
C6 0.064(5) 0.041(4) 0.043(4) 0.000(3) -0.010(4) -0.009(4)
C7 0.106(7) 0.133(8) 0.083(6) 0.016(6) -0.020(5) 0.031(7)
C8 0.054(5) 0.067(5) 0.055(4) -0.004(4) 0.010(4) -0.010(5)
C9 0.061(5) 0.078(5) 0.042(3) -0.001(4) 0.008(4) 0.009(5)
C10 0.109(7) 0.093(6) 0.066(5) -0.016(4) 0.020(5) 0.019(6)
C11 0.157(11) 0.199(11) 0.109(7) -0.094(8) 0.066(8) -0.069(11)
C12 0.128(8) 0.080(5) 0.076(5) 0.001(5) 0.001(6) -0.014(6)
C13 0.049(4) 0.033(3) 0.042(3) 0.001(3) -0.004(3) 0.005(3)
C14 0.059(4) 0.047(4) 0.042(3) 0.000(3) -0.004(3) 0.001(4)
C15 0.060(5) 0.035(3) 0.057(4) 0.003(3) 0.003(3) 0.000(4)
C16 0.072(5) 0.042(4) 0.048(4) 0.016(3) -0.002(4) 0.001(4)
C17 0.058(5) 0.052(4) 0.043(4) 0.009(3) -0.004(3) 0.013(4)
C18 0.048(4) 0.040(4) 0.052(4) 0.002(3) 0.002(3) 0.012(4)
C19 0.106(7) 0.059(4) 0.087(5) -0.017(4) -0.012(5) -0.016(5)
C20 0.047(4) 0.045(4) 0.046(4) -0.007(3) -0.006(3) 0.009(4)
C21 0.046(4) 0.051(4) 0.062(4) -0.007(4) -0.005(3) -0.004(4)
C22 0.085(6) 0.047(4) 0.064(4) -0.006(4) -0.017(4) 0.002(4)
C23 0.072(5) 0.043(4) 0.087(5) 0.003(4) 0.017(4) -0.002(4)
C24 0.080(6) 0.067(4) 0.067(4) 0.007(4) 0.004(4) 0.010(5)

_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 C2 1.363(8) . ?
O1 C7 1.418(8) . ?
O2 C8 1.235(7) . ?
O3 C14 1.368(6) . ?
O3 C19 1.444(7) . ?
O4 C20 1.231(6) . ?
N1 C8 1.350(7) . ?
N1 C6 1.407(7) . ?
N1 H1 0.8600 . ?
N2 C9 1.466(8) . ?
N2 C12 1.474(8) . ?
N2 HN2 0.97(7) . ?
N3 C20 1.332(7) . ?
N3 C18 1.417(7) . ?
N3 H3 0.8600 . ?
N4 C21 1.448(8) . ?
N4 C24 1.472(8) . ?
N4 HN4 0.81(7) . ?
C1 C6 1.401(8) . ?
C1 C2 1.401(9) . ?
C1 C13 1.489(7) . ?
C2 C3 1.399(8) . ?
C3 C4 1.370(9) . ?
C3 H3A 0.9300 . ?
C4 C5 1.372(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(8) . ?
C5 H5 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.517(9) . ?
C9 C10 1.519(8) . ?
C9 H9 0.9800 . ?
C10 C11 1.449(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.458(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.388(7) . ?
C13 C18 1.407(7) . ?
C14 C15 1.398(7) . ?
C15 C16 1.354(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.393(7) . ?
C17 H17 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.518(8) . ?
C21 C22 1.545(8) . ?
C21 H21 0.9800 . ?
C22 C23 1.488(8) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.519(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?

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
C2 O1 C7 119.2(5) . . ?
C14 O3 C19 117.2(5) . . ?
C8 N1 C6 129.9(6) . . ?
C8 N1 H1 115.1 . . ?
C6 N1 H1 115.1 . . ?
C9 N2 C12 108.5(5) . . ?
C9 N2 HN2 116(4) . . ?
C12 N2 HN2 114(4) . . ?
C20 N3 C18 129.6(5) . . ?
C20 N3 H3 115.2 . . ?
C18 N3 H3 115.2 . . ?
C21 N4 C24 106.5(5) . . ?
C21 N4 HN4 109(5) . . ?
C24 N4 HN4 113(6) . . ?
C6 C1 C2 118.1(6) . . ?
C6 C1 C13 123.6(6) . . ?
C2 C1 C13 118.3(6) . . ?
O1 C2 C3 122.8(7) . . ?
O1 C2 C1 116.6(6) . . ?
C3 C2 C1 120.6(7) . . ?
C4 C3 C2 118.7(7) . . ?
C4 C3 H3A 120.6 . . ?
C2 C3 H3A 120.6 . . ?
C3 C4 C5 122.1(7) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C4 C5 C6 119.3(7) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 121.0(7) . . ?
C5 C6 N1 122.8(6) . . ?
C1 C6 N1 116.2(5) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 N1 124.0(7) . . ?
O2 C8 C9 121.0(6) . . ?
N1 C8 C9 114.9(6) . . ?
N2 C9 C8 111.9(6) . . ?
N2 C9 C10 106.1(6) . . ?
C8 C9 C10 112.7(6) . . ?
N2 C9 H9 108.7 . . ?
C8 C9 H9 108.7 . . ?
C10 C9 H9 108.7 . . ?
C11 C10 C9 105.0(7) . . ?
C11 C10 H10A 110.7 . . ?
C9 C10 H10A 110.7 . . ?
C11 C10 H10B 110.7 . . ?
C9 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C10 C11 C12 108.7(7) . . ?
C10 C11 H11A 109.9 . . ?
C12 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
C12 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C11 C12 N2 106.2(7) . . ?
C11 C12 H12A 110.5 . . ?
N2 C12 H12A 110.5 . . ?
C11 C12 H12B 110.5 . . ?
N2 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C14 C13 C18 116.9(5) . . ?
C14 C13 C1 121.9(5) . . ?
C18 C13 C1 121.2(5) . . ?
O3 C14 C13 116.0(5) . . ?
O3 C14 C15 121.8(5) . . ?
C13 C14 C15 122.1(5) . . ?
C16 C15 C14 118.5(5) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C15 C16 C17 122.3(6) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C16 C17 C18 118.9(6) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C13 121.0(6) . . ?
C17 C18 N3 121.1(5) . . ?
C13 C18 N3 117.9(5) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 N3 124.3(6) . . ?
O4 C20 C21 120.2(5) . . ?
N3 C20 C21 115.5(5) . . ?
N4 C21 C20 112.0(5) . . ?
N4 C21 C22 107.4(5) . . ?
C20 C21 C22 110.7(5) . . ?
N4 C21 H21 108.9 . . ?
C20 C21 H21 108.9 . . ?
C22 C21 H21 108.9 . . ?
C23 C22 C21 105.3(5) . . ?
C23 C22 H22A 110.7 . . ?
C21 C22 H22A 110.7 . . ?
C23 C22 H22B 110.7 . . ?
C21 C22 H22B 110.7 . . ?
H22A C22 H22B 108.8 . . ?
C22 C23 C24 106.9(6) . . ?
C22 C23 H23A 110.3 . . ?
C24 C23 H23A 110.3 . . ?
C22 C23 H23B 110.3 . . ?
C24 C23 H23B 110.3 . . ?
H23A C23 H23B 108.6 . . ?
N4 C24 C23 107.8(6) . . ?
N4 C24 H24A 110.1 . . ?
C23 C24 H24A 110.1 . . ?
N4 C24 H24B 110.1 . . ?
C23 C24 H24B 110.1 . . ?
H24A C24 H24B 108.5 . . ?

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
C7 O1 C2 C3 23.9(10) . . . . ?
C7 O1 C2 C1 -158.7(6) . . . . ?
C6 C1 C2 O1 177.5(5) . . . . ?
C13 C1 C2 O1 -4.2(8) . . . . ?
C6 C1 C2 C3 -5.1(9) . . . . ?
C13 C1 C2 C3 173.2(5) . . . . ?
O1 C2 C3 C4 179.9(6) . . . . ?
C1 C2 C3 C4 2.7(9) . . . . ?
C2 C3 C4 C5 -0.4(10) . . . . ?
C3 C4 C5 C6 0.6(10) . . . . ?
C4 C5 C6 C1 -3.2(9) . . . . ?
C4 C5 C6 N1 175.2(5) . . . . ?
C2 C1 C6 C5 5.4(8) . . . . ?
C13 C1 C6 C5 -172.8(6) . . . . ?
C2 C1 C6 N1 -173.1(5) . . . . ?
C13 C1 C6 N1 8.7(8) . . . . ?
C8 N1 C6 C5 1.6(9) . . . . ?
C8 N1 C6 C1 -180.0(6) . . . . ?
C6 N1 C8 O2 7.5(10) . . . . ?
C6 N1 C8 C9 -171.7(5) . . . . ?
C12 N2 C9 C8 117.4(6) . . . . ?
C12 N2 C9 C10 -5.9(8) . . . . ?
O2 C8 C9 N2 -174.6(6) . . . . ?
N1 C8 C9 N2 4.7(8) . . . . ?
O2 C8 C9 C10 -55.1(9) . . . . ?
N1 C8 C9 C10 124.2(7) . . . . ?
N2 C9 C10 C11 18.2(9) . . . . ?
C8 C9 C10 C11 -104.6(8) . . . . ?
C9 C10 C11 C12 -24.1(10) . . . . ?
C10 C11 C12 N2 20.7(10) . . . . ?
C9 N2 C12 C11 -8.6(10) . . . . ?
C6 C1 C13 C14 -89.4(8) . . . . ?
C2 C1 C13 C14 92.4(7) . . . . ?
C6 C1 C13 C18 91.1(7) . . . . ?
C2 C1 C13 C18 -87.1(7) . . . . ?
C19 O3 C14 C13 165.7(6) . . . . ?
C19 O3 C14 C15 -16.3(9) . . . . ?
C18 C13 C14 O3 -176.3(5) . . . . ?
C1 C13 C14 O3 4.1(9) . . . . ?
C18 C13 C14 C15 5.6(9) . . . . ?
C1 C13 C14 C15 -173.9(6) . . . . ?
O3 C14 C15 C16 179.5(6) . . . . ?
C13 C14 C15 C16 -2.5(9) . . . . ?
C14 C15 C16 C17 -0.6(9) . . . . ?
C15 C16 C17 C18 0.3(9) . . . . ?
C16 C17 C18 C13 3.1(9) . . . . ?
C16 C17 C18 N3 -178.1(5) . . . . ?
C14 C13 C18 C17 -5.9(8) . . . . ?
C1 C13 C18 C17 173.6(6) . . . . ?
C14 C13 C18 N3 175.3(5) . . . . ?
C1 C13 C18 N3 -5.1(8) . . . . ?
C20 N3 C18 C17 8.5(9) . . . . ?
C20 N3 C18 C13 -172.7(6) . . . . ?
C18 N3 C20 O4 -1.6(10) . . . . ?
C18 N3 C20 C21 177.1(5) . . . . ?
C24 N4 C21 C20 96.0(6) . . . . ?
C24 N4 C21 C22 -25.7(7) . . . . ?
O4 C20 C21 N4 -176.6(6) . . . . ?
N3 C20 C21 N4 4.6(7) . . . . ?
O4 C20 C21 C22 -56.8(8) . . . . ?
N3 C20 C21 C22 124.4(6) . . . . ?
N4 C21 C22 C23 19.5(7) . . . . ?
C20 C21 C22 C23 -103.0(6) . . . . ?
C21 C22 C23 C24 -5.7(7) . . . . ?
C21 N4 C24 C23 22.1(7) . . . . ?
C22 C23 C24 N4 -9.6(7) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.070