# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2005

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'R. Stockman'
'David L. Hughes'
'Martin Rejzek'
'van Maarseveen, Jan H.'

_publ_contact_author_name        'Dr Robert Stockman'
_publ_contact_author_address     
;
School of Chemical Sciences
University of East Anglia
Norwich
NR4 7TJ
UNITED KINGDOM
;

_publ_contact_author_email       R.STOCKMAN@UEA.AC.UK

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
Combining Two-Directional Synthesis and Tandem
Reactions: Unexpected Desymmetrisation by Triazole Fragmentation
;

data_martinr4
_database_code_depnum_ccdc_archive 'CCDC 277408'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'Compound 6'
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H29 N3 O4'
_chemical_formula_structural     C9H15N-CH2COOEt-2,-C(NNH2)COOEt-10
_chemical_formula_sum            'C17 H29 N3 O4'
_chemical_formula_weight         339.43

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.048(2)
_cell_length_b                   15.296(3)
_cell_length_c                   7.872(3)
_cell_angle_alpha                104.54(2)
_cell_angle_beta                 93.23(3)
_cell_angle_gamma                80.363(18)
_cell_volume                     924.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      7.7
_cell_measurement_theta_max      11.3

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear, colourless'
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   'not applied'
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Rigaku/MSC AFC7R diffractometer'
_diffrn_measurement_method       'scintillation counter'

_diffrn_standards_number         3
_diffrn_standards_interval_count 250
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0

_diffrn_reflns_number            3533
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0619
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         25.04
_reflns_number_total             3277
_reflns_number_gt                2006
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'MSC/AFC Diffractometer Software (MSC, 1993)'
_computing_cell_refinement       'MSC/AFC Diffractometer Software (MSC, 1993)'
_computing_data_reduction        'MSC TeXsan/PROCESS (MSC, 1993)'
_computing_structure_solution    'SHELXS (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Johnson, 1971)'
_computing_publication_material  'SHELXL (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^)+(0.0790P)^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         3277
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1660
_refine_ls_wR_factor_gt          0.1439
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.005
_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
N1 N 0.3909(2) 0.23796(12) 0.4096(2) 0.0443(5) Uani 1 1 d . . .
C2 C 0.2945(3) 0.30252(16) 0.5583(3) 0.0540(7) Uani 1 1 d . . .
H2 H 0.3679 0.3444 0.6255 0.065 Uiso 1 1 calc R . .
C3 C 0.1449(4) 0.3574(2) 0.4870(4) 0.0793(10) Uani 1 1 d . . .
H3A H 0.0665 0.3167 0.4311 0.095 Uiso 1 1 calc R . .
H3B H 0.0874 0.4025 0.5840 0.095 Uiso 1 1 calc R . .
C4 C 0.1929(4) 0.4058(2) 0.3561(4) 0.0832(10) Uani 1 1 d . . .
H4A H 0.2587 0.4528 0.4143 0.100 Uiso 1 1 calc R . .
H4B H 0.0921 0.4350 0.3063 0.100 Uiso 1 1 calc R . .
C5 C 0.2952(4) 0.33663(19) 0.2119(4) 0.0694(9) Uani 1 1 d . . .
H5A H 0.3318 0.3680 0.1313 0.083 Uiso 1 1 calc R . .
H5B H 0.2247 0.2936 0.1467 0.083 Uiso 1 1 calc R . .
C6 C 0.4487(3) 0.28462(16) 0.2856(3) 0.0507(7) Uani 1 1 d . . .
H6 H 0.5004 0.2367 0.1871 0.061 Uiso 1 1 calc R . .
C7 C 0.5304(3) 0.17562(14) 0.4683(3) 0.0402(6) Uani 1 1 d . . .
H7 H 0.6138 0.2120 0.5323 0.048 Uiso 1 1 calc R . .
C8 C 0.4673(4) 0.12501(16) 0.5916(3) 0.0530(7) Uani 1 1 d . . .
H8A H 0.3919 0.0847 0.5269 0.064 Uiso 1 1 calc R . .
H8B H 0.5625 0.0876 0.6333 0.064 Uiso 1 1 calc R . .
C9 C 0.3762(4) 0.19051(18) 0.7466(3) 0.0621(8) Uani 1 1 d . . .
H9A H 0.3317 0.1568 0.8181 0.075 Uiso 1 1 calc R . .
H9B H 0.4533 0.2274 0.8185 0.075 Uiso 1 1 calc R . .
C10 C 0.2345(4) 0.25096(19) 0.6789(4) 0.0663(8) Uani 1 1 d . . .
H10A H 0.1773 0.2947 0.7777 0.080 Uiso 1 1 calc R . .
H10B H 0.1538 0.2137 0.6155 0.080 Uiso 1 1 calc R . .
C61 C 0.5836(4) 0.34484(17) 0.3628(3) 0.0604(8) Uani 1 1 d . A .
H61A H 0.5424 0.3876 0.4708 0.073 Uiso 1 1 calc R . .
H61B H 0.6845 0.3064 0.3912 0.073 Uiso 1 1 calc R . .
C62 C 0.6272(5) 0.3967(2) 0.2396(4) 0.0746(9) Uani 1 1 d . . .
O62A O 0.575(2) 0.4770(8) 0.240(2) 0.083(3) Uani 0.50 1 d P A 1
O63A O 0.7529(9) 0.3454(6) 0.1270(12) 0.080(2) Uani 0.50 1 d P A 1
C64A C 0.814(2) 0.3878(9) 0.0047(15) 0.117(4) Uani 0.50 1 d P A 1
H64A H 0.7969 0.4534 0.0541 0.140 Uiso 0.50 1 calc PR A 1
H64B H 0.9351 0.3676 -0.0058 0.140 Uiso 0.50 1 calc PR A 1
C65A C 0.7453(18) 0.3716(7) -0.1573(14) 0.122(4) Uani 0.50 1 d P A 1
H65A H 0.7978 0.4016 -0.2284 0.183 Uiso 0.50 1 calc PR A 1
H65B H 0.6268 0.3947 -0.1504 0.183 Uiso 0.50 1 calc PR A 1
H65C H 0.7621 0.3069 -0.2090 0.183 Uiso 0.50 1 calc PR A 1
O62B O 0.607(2) 0.4761(9) 0.270(3) 0.121(6) Uani 0.50 1 d P A 2
O63B O 0.6728(8) 0.3409(6) 0.0825(10) 0.0616(17) Uani 0.50 1 d P A 2
C64B C 0.6990(13) 0.3822(7) -0.0570(12) 0.071(2) Uani 0.50 1 d P A 2
H64C H 0.6028 0.4285 -0.0653 0.085 Uiso 0.50 1 calc PR A 2
H64D H 0.7066 0.3359 -0.1673 0.085 Uiso 0.50 1 calc PR A 2
C65B C 0.8572(13) 0.4254(7) -0.0293(15) 0.104(3) Uani 0.50 1 d P A 2
H65D H 0.8692 0.4523 -0.1249 0.155 Uiso 0.50 1 calc PR A 2
H65E H 0.9532 0.3795 -0.0241 0.155 Uiso 0.50 1 calc PR A 2
H65F H 0.8496 0.4720 0.0788 0.155 Uiso 0.50 1 calc PR A 2
C71 C 0.6164(3) 0.10491(14) 0.3155(3) 0.0396(5) Uani 1 1 d . . .
N711 N 0.5439(2) 0.05786(12) 0.1798(2) 0.0415(5) Uani 1 1 d . . .
N712 N 0.3770(3) 0.07272(16) 0.1617(3) 0.0534(6) Uani 1 1 d . . .
H712 H 0.315(3) 0.1172(18) 0.223(3) 0.050(8) Uiso 1 1 d . . .
H713 H 0.347(3) 0.0462(19) 0.058(4) 0.062(8) Uiso 1 1 d . . .
C72 C 0.8009(3) 0.08097(16) 0.3252(3) 0.0471(6) Uani 1 1 d . . .
O72 O 0.8900(2) 0.12787(15) 0.4205(3) 0.0828(7) Uani 1 1 d . . .
O73 O 0.8606(2) -0.00023(11) 0.2171(2) 0.0543(5) Uani 1 1 d . . .
C74 C 1.0399(3) -0.0284(2) 0.2186(4) 0.0727(9) Uani 1 1 d . . .
H74A H 1.0803 -0.0259 0.3379 0.087 Uiso 1 1 calc R . .
H74B H 1.0951 0.0123 0.1725 0.087 Uiso 1 1 calc R . .
C75 C 1.0799(4) -0.1230(2) 0.1093(5) 0.0886(11) Uani 1 1 d . . .
H75A H 1.1996 -0.1425 0.1097 0.133 Uiso 1 1 calc R . .
H75B H 1.0405 -0.1249 -0.0088 0.133 Uiso 1 1 calc R . .
H75C H 1.0254 -0.1630 0.1561 0.133 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
N1 0.0601(13) 0.0321(10) 0.0338(10) 0.0005(8) 0.0034(9) 0.0017(9)
C2 0.0665(17) 0.0390(13) 0.0460(14) -0.0033(11) 0.0106(13) 0.0028(12)
C3 0.083(2) 0.0654(19) 0.073(2) 0.0062(16) 0.0099(17) 0.0201(17)
C4 0.102(3) 0.0582(18) 0.071(2) 0.0118(16) -0.0086(18) 0.0303(18)
C5 0.096(2) 0.0515(16) 0.0515(16) 0.0116(13) -0.0091(15) 0.0097(16)
C6 0.0759(18) 0.0337(12) 0.0375(13) 0.0058(10) 0.0025(12) 0.0018(12)
C7 0.0539(14) 0.0301(11) 0.0325(12) 0.0025(9) -0.0025(11) -0.0040(10)
C8 0.0764(18) 0.0368(13) 0.0445(14) 0.0076(11) 0.0064(13) -0.0074(12)
C9 0.090(2) 0.0515(15) 0.0454(15) 0.0081(13) 0.0168(14) -0.0132(15)
C10 0.079(2) 0.0566(17) 0.0571(17) 0.0003(14) 0.0248(15) -0.0060(15)
C61 0.095(2) 0.0430(14) 0.0454(15) 0.0146(12) 0.0077(14) -0.0088(14)
C62 0.123(3) 0.0425(16) 0.0583(18) 0.0105(14) 0.0193(18) -0.0094(19)
O62A 0.136(6) 0.035(5) 0.068(6) 0.016(3) 0.020(4) 0.027(4)
O63A 0.097(6) 0.061(3) 0.086(6) 0.020(4) 0.036(4) -0.007(4)
C64A 0.148(11) 0.125(9) 0.088(8) 0.016(6) 0.041(8) -0.056(9)
C65A 0.181(11) 0.112(7) 0.092(7) 0.043(7) -0.034(8) -0.060(7)
O62B 0.256(16) 0.045(5) 0.078(7) 0.020(4) 0.025(8) -0.050(7)
O63B 0.078(5) 0.057(3) 0.054(3) 0.021(2) 0.011(3) -0.009(3)
C64B 0.073(5) 0.096(5) 0.054(5) 0.032(5) 0.000(4) -0.019(4)
C65B 0.097(7) 0.118(8) 0.112(8) 0.051(6) 0.028(5) -0.019(6)
C71 0.0508(15) 0.0303(11) 0.0356(12) 0.0057(10) 0.0004(11) -0.0045(10)
N711 0.0451(12) 0.0341(10) 0.0398(11) 0.0002(9) 0.0009(9) -0.0040(9)
N712 0.0433(14) 0.0516(14) 0.0496(15) -0.0131(12) 0.0032(11) -0.0015(11)
C72 0.0546(16) 0.0455(14) 0.0413(14) 0.0123(12) -0.0033(12) -0.0068(12)
O72 0.0612(13) 0.0812(15) 0.0868(15) -0.0117(12) -0.0200(11) -0.0139(11)
O73 0.0465(10) 0.0459(10) 0.0643(11) 0.0080(9) 0.0051(8) 0.0027(8)
C74 0.0479(17) 0.083(2) 0.082(2) 0.0234(18) 0.0048(15) 0.0097(15)
C75 0.077(2) 0.070(2) 0.113(3) 0.028(2) 0.031(2) 0.0235(17)

_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 C7 1.479(3) . ?
N1 C6 1.480(3) . ?
N1 C2 1.487(3) . ?
C2 C3 1.514(4) . ?
C2 C10 1.520(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.511(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.516(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.522(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C61 1.542(4) . ?
C6 H6 0.9800 . ?
C7 C71 1.512(3) . ?
C7 C8 1.537(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.507(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.505(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C61 C62 1.486(4) . ?
C61 H61A 0.9700 . ?
C61 H61B 0.9700 . ?
C62 O62B 1.162(13) . ?
C62 O62A 1.230(12) . ?
C62 O63B 1.344(9) . ?
C62 O63A 1.382(9) . ?
O63A C64A 1.437(13) . ?
C64A C65A 1.344(17) . ?
C64A H64A 0.9700 . ?
C64A H64B 0.9700 . ?
C65A H65A 0.9600 . ?
C65A H65B 0.9600 . ?
C65A H65C 0.9600 . ?
O63B C64B 1.438(11) . ?
C64B C65B 1.511(15) . ?
C64B H64C 0.9700 . ?
C64B H64D 0.9700 . ?
C65B H65D 0.9600 . ?
C65B H65E 0.9600 . ?
C65B H65F 0.9600 . ?
C71 N711 1.298(3) . ?
C71 C72 1.471(3) . ?
N711 N712 1.330(3) . ?
N712 H712 0.83(3) . ?
N712 H713 0.86(3) . ?
C72 O72 1.197(3) . ?
C72 O73 1.347(3) . ?
O73 C74 1.436(3) . ?
C74 C75 1.479(4) . ?
C74 H74A 0.9700 . ?
C74 H74B 0.9700 . ?
C75 H75A 0.9600 . ?
C75 H75B 0.9600 . ?
C75 H75C 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
C7 N1 C6 111.90(18) . . ?
C7 N1 C2 112.74(17) . . ?
C6 N1 C2 112.87(17) . . ?
N1 C2 C3 109.3(2) . . ?
N1 C2 C10 110.69(19) . . ?
C3 C2 C10 109.9(2) . . ?
N1 C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
C10 C2 H2 109.0 . . ?
C4 C3 C2 113.3(3) . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 C5 109.0(2) . . ?
C3 C4 H4A 109.9 . . ?
C5 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
C5 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C4 C5 C6 111.7(2) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
N1 C6 C5 108.6(2) . . ?
N1 C6 C61 114.07(19) . . ?
C5 C6 C61 113.0(2) . . ?
N1 C6 H6 106.9 . . ?
C5 C6 H6 106.9 . . ?
C61 C6 H6 106.9 . . ?
N1 C7 C71 111.91(17) . . ?
N1 C7 C8 111.32(19) . . ?
C71 C7 C8 108.09(17) . . ?
N1 C7 H7 108.5 . . ?
C71 C7 H7 108.5 . . ?
C8 C7 H7 108.5 . . ?
C9 C8 C7 111.76(19) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 108.4(2) . . ?
C10 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
C10 C9 H9B 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C9 C10 C2 112.8(2) . . ?
C9 C10 H10A 109.0 . . ?
C2 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C2 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C62 C61 C6 112.3(2) . . ?
C62 C61 H61A 109.1 . . ?
C6 C61 H61A 109.1 . . ?
C62 C61 H61B 109.1 . . ?
C6 C61 H61B 109.1 . . ?
H61A C61 H61B 107.9 . . ?
O62B C62 O62A 16.1(19) . . ?
O62B C62 O63B 124.3(10) . . ?
O62A C62 O63B 115.7(9) . . ?
O62B C62 O63A 120.1(10) . . ?
O62A C62 O63A 121.0(8) . . ?
O63B C62 O63A 30.6(3) . . ?
O62B C62 C61 123.7(9) . . ?
O62A C62 C61 127.6(7) . . ?
O63B C62 C61 111.5(4) . . ?
O63A C62 C61 111.1(4) . . ?
C62 O63A C64A 117.8(8) . . ?
C65A C64A O63A 116.6(14) . . ?
C65A C64A H64A 108.2 . . ?
O63A C64A H64A 108.2 . . ?
C65A C64A H64B 108.1 . . ?
O63A C64A H64B 108.1 . . ?
H64A C64A H64B 107.3 . . ?
C64A C65A H65A 109.5 . . ?
C64A C65A H65B 109.5 . . ?
H65A C65A H65B 109.5 . . ?
C64A C65A H65C 109.5 . . ?
H65A C65A H65C 109.5 . . ?
H65B C65A H65C 109.5 . . ?
C62 O63B C64B 117.9(7) . . ?
O63B C64B C65B 112.4(9) . . ?
O63B C64B H64C 109.1 . . ?
C65B C64B H64C 109.1 . . ?
O63B C64B H64D 109.1 . . ?
C65B C64B H64D 109.1 . . ?
H64C C64B H64D 107.9 . . ?
C64B C65B H65D 109.5 . . ?
C64B C65B H65E 109.5 . . ?
H65D C65B H65E 109.5 . . ?
C64B C65B H65F 109.5 . . ?
H65D C65B H65F 109.5 . . ?
H65E C65B H65F 109.5 . . ?
N711 C71 C72 115.4(2) . . ?
N711 C71 C7 126.9(2) . . ?
C72 C71 C7 117.5(2) . . ?
C71 N711 N712 119.9(2) . . ?
N711 N712 H712 123.7(17) . . ?
N711 N712 H713 110.4(18) . . ?
H712 N712 H713 121(3) . . ?
O72 C72 O73 122.8(2) . . ?
O72 C72 C71 124.0(2) . . ?
O73 C72 C71 113.2(2) . . ?
C72 O73 C74 116.6(2) . . ?
O73 C74 C75 108.9(3) . . ?
O73 C74 H74A 109.9 . . ?
C75 C74 H74A 109.9 . . ?
O73 C74 H74B 109.9 . . ?
C75 C74 H74B 109.9 . . ?
H74A C74 H74B 108.3 . . ?
C74 C75 H75A 109.5 . . ?
C74 C75 H75B 109.5 . . ?
H75A C75 H75B 109.5 . . ?
C74 C75 H75C 109.5 . . ?
H75A C75 H75C 109.5 . . ?
H75B C75 H75C 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
C7 N1 C2 C3 -174.7(2) . . . . ?
C6 N1 C2 C3 57.3(3) . . . . ?
C7 N1 C2 C10 -53.4(3) . . . . ?
C6 N1 C2 C10 178.6(2) . . . . ?
N1 C2 C3 C4 -54.4(3) . . . . ?
C10 C2 C3 C4 -176.1(2) . . . . ?
C2 C3 C4 C5 54.0(4) . . . . ?
C3 C4 C5 C6 -55.7(4) . . . . ?
C7 N1 C6 C5 172.11(18) . . . . ?
C2 N1 C6 C5 -59.4(3) . . . . ?
C7 N1 C6 C61 -60.9(2) . . . . ?
C2 N1 C6 C61 67.6(3) . . . . ?
C4 C5 C6 N1 58.4(3) . . . . ?
C4 C5 C6 C61 -69.2(3) . . . . ?
C6 N1 C7 C71 -56.8(2) . . . . ?
C2 N1 C7 C71 174.68(19) . . . . ?
C6 N1 C7 C8 -177.89(17) . . . . ?
C2 N1 C7 C8 53.6(2) . . . . ?
N1 C7 C8 C9 -55.5(3) . . . . ?
C71 C7 C8 C9 -178.8(2) . . . . ?
C7 C8 C9 C10 56.1(3) . . . . ?
C8 C9 C10 C2 -56.9(3) . . . . ?
N1 C2 C10 C9 55.8(3) . . . . ?
C3 C2 C10 C9 176.7(2) . . . . ?
N1 C6 C61 C62 -175.0(2) . . . . ?
C5 C6 C61 C62 -50.3(3) . . . . ?
C6 C61 C62 O62B 118.4(13) . . . . ?
C6 C61 C62 O62A 99.1(12) . . . . ?
C6 C61 C62 O63B -54.1(4) . . . . ?
C6 C61 C62 O63A -87.0(4) . . . . ?
O62B C62 O63A C64A -21.6(16) . . . . ?
O62A C62 O63A C64A -2.9(15) . . . . ?
O63B C62 O63A C64A 85.9(15) . . . . ?
C61 C62 O63A C64A -177.2(8) . . . . ?
C62 O63A C64A C65A -95.7(13) . . . . ?
O62B C62 O63B C64B 0.3(15) . . . . ?
O62A C62 O63B C64B 16.1(12) . . . . ?
O63A C62 O63B C64B -91.9(14) . . . . ?
C61 C62 O63B C64B 172.7(6) . . . . ?
C62 O63B C64B C65B 71.2(9) . . . . ?
N1 C7 C71 N711 -44.1(3) . . . . ?
C8 C7 C71 N711 78.8(3) . . . . ?
N1 C7 C71 C72 140.8(2) . . . . ?
C8 C7 C71 C72 -96.2(2) . . . . ?
C72 C71 N711 N712 178.2(2) . . . . ?
C7 C71 N711 N712 3.0(3) . . . . ?
N711 C71 C72 O72 165.0(2) . . . . ?
C7 C71 C72 O72 -19.4(4) . . . . ?
N711 C71 C72 O73 -15.8(3) . . . . ?
C7 C71 C72 O73 159.86(18) . . . . ?
O72 C72 O73 C74 -0.9(4) . . . . ?
C71 C72 O73 C74 179.9(2) . . . . ?
C72 O73 C74 C75 173.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.042