# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2009


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Jian Zhou'
_publ_contact_author_email       JZHOU@CHEM.ECNU.EDU.CN

_publ_section_title              
;
Asymmetric Construction of Quaternary Stereocenters by Direct
Organocatalytic Amination of 3-Substituted Oxindoles
;
loop_
_publ_author_name
'Jian Zhou'
'Miao Ding'
'Tai-Ping Du'
'Zi-Qing Qian'
'Bo-Lun Wang'
;
Xiao-Li Zhao
;
'Feng Zhou'

# Attachment 'Z.cif'

data_z
_database_code_depnum_ccdc_archive 'CCDC 739060'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H26 Br N3 O5'
_chemical_formula_weight         504.38

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'
Br Br -0.2901 2.4595 '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                   9.0411(3)
_cell_length_b                   12.0586(4)
_cell_length_c                   12.8583(4)
_cell_angle_alpha                115.6260(10)
_cell_angle_beta                 92.7780(10)
_cell_angle_gamma                107.0370(10)
_cell_volume                     1183.27(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.523
_exptl_crystal_size_mid          0.282
_exptl_crystal_size_min          0.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    1.775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.670721
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13845
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4139
_reflns_number_gt                3348
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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^)+(0.0491P)^2^+1.0162P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4139
_refine_ls_number_parameters     289
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.024
_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
Br1 Br 0.57585(5) 1.13022(4) 0.17648(4) 0.08609(19) Uani 1 1 d . . .
O1 O 0.1115(2) 0.88373(17) 0.50466(16) 0.0436(4) Uani 1 1 d . . .
O2 O -0.2045(2) 0.47629(18) 0.42930(17) 0.0464(4) Uani 1 1 d . . .
O3 O -0.2406(2) 0.63975(18) 0.40090(17) 0.0440(4) Uani 1 1 d . . .
O4 O -0.0889(3) 0.34753(19) 0.17278(18) 0.0559(5) Uani 1 1 d . . .
O5 O 0.0777(2) 0.31406(17) 0.28413(17) 0.0482(5) Uani 1 1 d . . .
N1 N -0.0261(2) 0.58984(19) 0.35959(18) 0.0365(5) Uani 1 1 d . . .
N2 N 0.0619(2) 0.51055(19) 0.35162(19) 0.0379(5) Uani 1 1 d . . .
H2B H 0.1478 0.5388 0.4016 0.046 Uiso 1 1 calc R . .
N3 N -0.0599(2) 0.86659(19) 0.35647(18) 0.0389(5) Uani 1 1 d . . .
H3A H -0.0650 0.9441 0.3906 0.047 Uiso 1 1 calc R . .
C1 C 0.2264(3) 0.7982(3) 0.1453(2) 0.0460(6) Uani 1 1 d . . .
H1A H 0.1390 0.7312 0.0891 0.055 Uiso 1 1 calc R . .
C2 C 0.3171(4) 0.8962(3) 0.1219(3) 0.0553(7) Uani 1 1 d . . .
H2A H 0.2904 0.8955 0.0508 0.066 Uiso 1 1 calc R . .
C3 C 0.4468(3) 0.9943(3) 0.2049(3) 0.0517(7) Uani 1 1 d . . .
C4 C 0.4880(3) 0.9973(3) 0.3101(3) 0.0540(7) Uani 1 1 d . . .
H4A H 0.5767 1.0636 0.3654 0.065 Uiso 1 1 calc R . .
C5 C 0.3956(3) 0.9001(3) 0.3324(3) 0.0505(7) Uani 1 1 d . . .
H5A H 0.4222 0.9025 0.4043 0.061 Uiso 1 1 calc R . .
C6 C 0.2644(3) 0.7988(2) 0.2512(2) 0.0377(6) Uani 1 1 d . . .
C7 C 0.1798(3) 0.6888(2) 0.2775(2) 0.0398(6) Uani 1 1 d . . .
H7A H 0.2482 0.6944 0.3414 0.048 Uiso 1 1 calc R . .
H7B H 0.1657 0.6063 0.2087 0.048 Uiso 1 1 calc R . .
C8 C 0.0175(3) 0.6837(2) 0.3111(2) 0.0323(5) Uani 1 1 d . . .
C9 C 0.0302(3) 0.8237(2) 0.4057(2) 0.0344(5) Uani 1 1 d . . .
C10 C -0.1446(3) 0.7703(2) 0.2431(2) 0.0367(5) Uani 1 1 d . . .
C11 C -0.1054(3) 0.6590(2) 0.2122(2) 0.0347(5) Uani 1 1 d . . .
C12 C -0.1747(3) 0.5509(3) 0.1038(2) 0.0444(6) Uani 1 1 d . . .
H12A H -0.1489 0.4757 0.0819 0.053 Uiso 1 1 calc R . .
C13 C -0.2834(4) 0.5564(3) 0.0282(3) 0.0541(7) Uani 1 1 d . . .
H13A H -0.3303 0.4845 -0.0456 0.065 Uiso 1 1 calc R . .
C14 C -0.3228(3) 0.6677(3) 0.0611(3) 0.0560(8) Uani 1 1 d . . .
H14A H -0.3971 0.6691 0.0094 0.067 Uiso 1 1 calc R . .
C15 C -0.2540(3) 0.7771(3) 0.1693(3) 0.0485(7) Uani 1 1 d . . .
H15A H -0.2802 0.8521 0.1916 0.058 Uiso 1 1 calc R . .
C16 C 0.0054(3) 0.3846(2) 0.2600(2) 0.0407(6) Uani 1 1 d . . .
C17 C 0.0425(4) 0.1788(2) 0.1921(3) 0.0487(7) Uani 1 1 d U . .
H17A H -0.0674 0.1427 0.1500 0.058 Uiso 1 1 calc R . .
C18 C 0.1493(6) 0.1784(4) 0.1083(4) 0.0939(14) Uani 1 1 d U . .
H18A H 0.1303 0.2279 0.0707 0.141 Uiso 1 1 calc R . .
H18B H 0.1299 0.0897 0.0499 0.141 Uiso 1 1 calc R . .
H18C H 0.2571 0.2174 0.1502 0.141 Uiso 1 1 calc R . .
C19 C 0.0634(7) 0.1044(4) 0.2550(4) 0.0946(14) Uani 1 1 d U . .
H19A H -0.0089 0.1083 0.3077 0.142 Uiso 1 1 calc R . .
H19B H 0.1698 0.1424 0.2992 0.142 Uiso 1 1 calc R . .
H19C H 0.0428 0.0146 0.1989 0.142 Uiso 1 1 calc R . .
C20 C -0.1631(3) 0.5609(2) 0.3989(2) 0.0370(5) Uani 1 1 d . . .
C21 C -0.4012(3) 0.6066(3) 0.4210(3) 0.0599(8) Uani 1 1 d U . .
H21A H -0.4080 0.5707 0.4767 0.072 Uiso 1 1 calc R . .
C22 C -0.4328(5) 0.7313(5) 0.4734(4) 0.1071(17) Uani 1 1 d U . .
H22C H -0.5379 0.7150 0.4886 0.161 Uiso 1 1 calc R . .
H22D H -0.4229 0.7676 0.4197 0.161 Uiso 1 1 calc R . .
H22A H -0.3580 0.7921 0.5460 0.161 Uiso 1 1 calc R . .
C23 C -0.5086(5) 0.5089(5) 0.3092(5) 0.134(2) Uani 1 1 d U . .
H23C H -0.4830 0.4303 0.2794 0.202 Uiso 1 1 calc R . .
H23D H -0.4982 0.5427 0.2536 0.202 Uiso 1 1 calc R . .
H23A H -0.6153 0.4894 0.3210 0.202 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
Br1 0.0853(3) 0.0690(3) 0.1093(4) 0.0560(2) 0.0414(2) 0.0083(2)
O1 0.0530(11) 0.0372(9) 0.0351(10) 0.0123(8) 0.0017(9) 0.0166(8)
O2 0.0470(10) 0.0443(10) 0.0555(12) 0.0328(9) 0.0096(9) 0.0116(8)
O3 0.0396(9) 0.0490(10) 0.0608(12) 0.0357(9) 0.0189(9) 0.0221(8)
O4 0.0646(13) 0.0416(10) 0.0524(13) 0.0176(9) -0.0077(11) 0.0163(9)
O5 0.0600(12) 0.0321(9) 0.0527(12) 0.0175(9) 0.0053(9) 0.0208(8)
N1 0.0387(11) 0.0329(10) 0.0462(12) 0.0231(10) 0.0112(9) 0.0162(9)
N2 0.0363(11) 0.0309(10) 0.0480(13) 0.0186(10) 0.0046(9) 0.0142(9)
N3 0.0498(12) 0.0300(10) 0.0395(12) 0.0164(9) 0.0066(10) 0.0176(9)
C1 0.0432(14) 0.0460(15) 0.0435(16) 0.0191(13) 0.0100(12) 0.0114(12)
C2 0.0578(18) 0.0612(18) 0.0526(18) 0.0339(15) 0.0185(14) 0.0157(15)
C3 0.0499(16) 0.0439(15) 0.068(2) 0.0306(14) 0.0294(15) 0.0152(13)
C4 0.0463(16) 0.0437(15) 0.0578(19) 0.0178(14) 0.0130(14) 0.0057(12)
C5 0.0499(16) 0.0481(15) 0.0459(16) 0.0210(13) 0.0058(13) 0.0092(13)
C6 0.0362(13) 0.0358(13) 0.0421(14) 0.0173(11) 0.0138(11) 0.0145(10)
C7 0.0385(13) 0.0368(13) 0.0476(15) 0.0205(12) 0.0126(11) 0.0160(11)
C8 0.0354(12) 0.0286(11) 0.0334(13) 0.0149(10) 0.0068(10) 0.0111(9)
C9 0.0387(13) 0.0303(12) 0.0360(14) 0.0169(11) 0.0098(11) 0.0118(10)
C10 0.0376(13) 0.0382(13) 0.0386(14) 0.0217(11) 0.0090(11) 0.0128(10)
C11 0.0357(12) 0.0348(12) 0.0356(13) 0.0183(11) 0.0093(10) 0.0116(10)
C12 0.0463(15) 0.0408(14) 0.0390(15) 0.0156(12) 0.0058(12) 0.0109(12)
C13 0.0517(16) 0.0566(17) 0.0416(16) 0.0202(14) -0.0008(13) 0.0080(14)
C14 0.0447(15) 0.072(2) 0.0526(18) 0.0371(17) -0.0020(13) 0.0122(14)
C15 0.0480(15) 0.0557(17) 0.0556(18) 0.0348(15) 0.0097(13) 0.0230(13)
C16 0.0437(14) 0.0332(13) 0.0492(16) 0.0228(12) 0.0119(13) 0.0130(11)
C17 0.0571(16) 0.0289(12) 0.0550(17) 0.0152(12) 0.0122(14) 0.0151(12)
C18 0.122(4) 0.060(2) 0.089(3) 0.026(2) 0.055(3) 0.026(2)
C19 0.170(5) 0.051(2) 0.083(3) 0.038(2) 0.041(3) 0.053(3)
C20 0.0378(13) 0.0341(12) 0.0374(14) 0.0175(11) 0.0027(10) 0.0099(10)
C21 0.0448(16) 0.081(2) 0.083(2) 0.056(2) 0.0290(16) 0.0310(16)
C22 0.068(3) 0.115(4) 0.113(4) 0.016(3) 0.018(2) 0.056(3)
C23 0.046(2) 0.108(4) 0.153(5) -0.010(3) 0.000(3) 0.011(2)

_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
Br1 C3 1.902(3) . ?
O1 C9 1.218(3) . ?
O2 C20 1.212(3) . ?
O3 C20 1.329(3) . ?
O3 C21 1.457(3) . ?
O4 C16 1.198(3) . ?
O5 C16 1.335(3) . ?
O5 C17 1.467(3) . ?
N1 C20 1.368(3) . ?
N1 N2 1.388(3) . ?
N1 C8 1.484(3) . ?
N2 C16 1.376(3) . ?
N2 H2B 0.8600 . ?
N3 C9 1.346(3) . ?
N3 C10 1.402(3) . ?
N3 H3A 0.8600 . ?
C1 C6 1.384(4) . ?
C1 C2 1.387(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.374(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.368(5) . ?
C4 C5 1.377(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.385(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.509(3) . ?
C7 C8 1.541(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C11 1.510(3) . ?
C8 C9 1.562(3) . ?
C10 C15 1.381(4) . ?
C10 C11 1.383(3) . ?
C11 C12 1.379(4) . ?
C12 C13 1.384(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.383(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.383(4) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C17 C18 1.480(5) . ?
C17 C19 1.485(5) . ?
C17 H17A 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 C23 1.458(6) . ?
C21 C22 1.480(5) . ?
C21 H21A 0.9800 . ?
C22 H22C 0.9600 . ?
C22 H22D 0.9600 . ?
C22 H22A 0.9600 . ?
C23 H23C 0.9600 . ?
C23 H23D 0.9600 . ?
C23 H23A 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
C20 O3 C21 116.9(2) . . ?
C16 O5 C17 116.4(2) . . ?
C20 N1 N2 114.95(19) . . ?
C20 N1 C8 124.07(19) . . ?
N2 N1 C8 120.35(19) . . ?
C16 N2 N1 117.0(2) . . ?
C16 N2 H2B 121.5 . . ?
N1 N2 H2B 121.5 . . ?
C9 N3 C10 112.2(2) . . ?
C9 N3 H3A 123.9 . . ?
C10 N3 H3A 123.9 . . ?
C6 C1 C2 120.8(3) . . ?
C6 C1 H1A 119.6 . . ?
C2 C1 H1A 119.6 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 Br1 117.8(2) . . ?
C2 C3 Br1 120.9(2) . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 H4A 120.7 . . ?
C5 C4 H4A 120.7 . . ?
C4 C5 C6 122.1(3) . . ?
C4 C5 H5A 119.0 . . ?
C6 C5 H5A 119.0 . . ?
C1 C6 C5 117.8(2) . . ?
C1 C6 C7 123.3(2) . . ?
C5 C6 C7 118.6(2) . . ?
C6 C7 C8 117.2(2) . . ?
C6 C7 H7A 108.0 . . ?
C8 C7 H7A 108.0 . . ?
C6 C7 H7B 108.0 . . ?
C8 C7 H7B 108.0 . . ?
H7A C7 H7B 107.2 . . ?
N1 C8 C11 115.17(19) . . ?
N1 C8 C7 107.94(19) . . ?
C11 C8 C7 113.0(2) . . ?
N1 C8 C9 110.28(19) . . ?
C11 C8 C9 101.25(18) . . ?
C7 C8 C9 109.00(19) . . ?
O1 C9 N3 126.8(2) . . ?
O1 C9 C8 125.6(2) . . ?
N3 C9 C8 107.6(2) . . ?
C15 C10 C11 122.3(2) . . ?
C15 C10 N3 128.2(2) . . ?
C11 C10 N3 109.6(2) . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 C8 131.0(2) . . ?
C10 C11 C8 109.1(2) . . ?
C11 C12 C13 118.7(3) . . ?
C11 C12 H12A 120.6 . . ?
C13 C12 H12A 120.6 . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14A 119.4 . . ?
C13 C14 H14A 119.4 . . ?
C10 C15 C14 117.2(3) . . ?
C10 C15 H15A 121.4 . . ?
C14 C15 H15A 121.4 . . ?
O4 C16 O5 126.7(2) . . ?
O4 C16 N2 125.1(2) . . ?
O5 C16 N2 108.1(2) . . ?
O5 C17 C18 109.1(2) . . ?
O5 C17 C19 105.6(3) . . ?
C18 C17 C19 113.5(3) . . ?
O5 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C19 C17 H17A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 O3 125.6(2) . . ?
O2 C20 N1 123.9(2) . . ?
O3 C20 N1 110.5(2) . . ?
O3 C21 C23 108.9(3) . . ?
O3 C21 C22 106.0(3) . . ?
C23 C21 C22 113.0(4) . . ?
O3 C21 H21A 109.6 . . ?
C23 C21 H21A 109.6 . . ?
C22 C21 H21A 109.6 . . ?
C21 C22 H22C 109.5 . . ?
C21 C22 H22D 109.5 . . ?
H22C C22 H22D 109.5 . . ?
C21 C22 H22A 109.5 . . ?
H22C C22 H22A 109.5 . . ?
H22D C22 H22A 109.5 . . ?
C21 C23 H23C 109.5 . . ?
C21 C23 H23D 109.5 . . ?
H23C C23 H23D 109.5 . . ?
C21 C23 H23A 109.5 . . ?
H23C C23 H23A 109.5 . . ?
H23D C23 H23A 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
C20 N1 N2 C16 74.0(3) . . . . ?
C8 N1 N2 C16 -97.3(3) . . . . ?
C6 C1 C2 C3 0.5(4) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C1 C2 C3 Br1 179.5(2) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
Br1 C3 C4 C5 179.7(2) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C2 C1 C6 C7 -174.2(3) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C4 C5 C6 C7 173.7(3) . . . . ?
C1 C6 C7 C8 -78.5(3) . . . . ?
C5 C6 C7 C8 107.6(3) . . . . ?
C20 N1 C8 C11 -52.9(3) . . . . ?
N2 N1 C8 C11 117.5(2) . . . . ?
C20 N1 C8 C7 179.8(2) . . . . ?
N2 N1 C8 C7 -9.7(3) . . . . ?
C20 N1 C8 C9 60.9(3) . . . . ?
N2 N1 C8 C9 -128.7(2) . . . . ?
C6 C7 C8 N1 -167.0(2) . . . . ?
C6 C7 C8 C11 64.5(3) . . . . ?
C6 C7 C8 C9 -47.2(3) . . . . ?
C10 N3 C9 O1 -177.1(2) . . . . ?
C10 N3 C9 C8 5.1(3) . . . . ?
N1 C8 C9 O1 54.2(3) . . . . ?
C11 C8 C9 O1 176.6(2) . . . . ?
C7 C8 C9 O1 -64.1(3) . . . . ?
N1 C8 C9 N3 -127.9(2) . . . . ?
C11 C8 C9 N3 -5.5(2) . . . . ?
C7 C8 C9 N3 113.7(2) . . . . ?
C9 N3 C10 C15 176.4(3) . . . . ?
C9 N3 C10 C11 -2.5(3) . . . . ?
C15 C10 C11 C12 1.1(4) . . . . ?
N3 C10 C11 C12 -180.0(2) . . . . ?
C15 C10 C11 C8 179.6(2) . . . . ?
N3 C10 C11 C8 -1.5(3) . . . . ?
N1 C8 C11 C12 -58.6(3) . . . . ?
C7 C8 C11 C12 66.0(3) . . . . ?
C9 C8 C11 C12 -177.6(2) . . . . ?
N1 C8 C11 C10 123.1(2) . . . . ?
C7 C8 C11 C10 -112.3(2) . . . . ?
C9 C8 C11 C10 4.2(2) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C8 C11 C12 C13 -178.5(3) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C15 0.8(5) . . . . ?
C11 C10 C15 C14 -0.8(4) . . . . ?
N3 C10 C15 C14 -179.5(3) . . . . ?
C13 C14 C15 C10 -0.1(4) . . . . ?
C17 O5 C16 O4 2.6(4) . . . . ?
C17 O5 C16 N2 -175.3(2) . . . . ?
N1 N2 C16 O4 18.7(4) . . . . ?
N1 N2 C16 O5 -163.4(2) . . . . ?
C16 O5 C17 C18 85.9(3) . . . . ?
C16 O5 C17 C19 -151.8(3) . . . . ?
C21 O3 C20 O2 -11.7(4) . . . . ?
C21 O3 C20 N1 169.6(2) . . . . ?
N2 N1 C20 O2 2.7(4) . . . . ?
C8 N1 C20 O2 173.6(2) . . . . ?
N2 N1 C20 O3 -178.5(2) . . . . ?
C8 N1 C20 O3 -7.7(3) . . . . ?
C20 O3 C21 C23 -83.9(4) . . . . ?
C20 O3 C21 C22 154.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2B O2 0.86 2.30 2.961(3) 133.2 2_566
N3 H3A O1 0.86 2.11 2.954(3) 166.8 2_576

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.048