# 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        'Luis Miranda'
_publ_contact_author_email       LMIRANDA@SERVIDOR.UNAM.MX

_publ_section_title              
;
Synthesis of azepino[4,5-b]indolones via an
intermolecular radical oxidative substitution of N-Boc tryptamine.
;
loop_
_publ_author_name
'Luis Miranda'
'Roberto Martinez'
'Paul E. Reyes-Gutierrez'
'Ruben O. Torres-Ochoa'

# Attachment '038MAR08.cif'

data_038MAR08
_database_code_depnum_ccdc_archive 'CCDC 711467'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 N2 O4'
_chemical_formula_sum            'C15 H16 N2 O4'
_chemical_formula_weight         288.30

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'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   10.7390(14)
_cell_length_b                   11.1934(15)
_cell_length_c                   12.1609(16)
_cell_angle_alpha                93.177(2)
_cell_angle_beta                 97.768(2)
_cell_angle_gamma                109.836(2)
_cell_volume                     1354.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5634
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      25.36

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.128
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_max          0.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_process_details   '(Sheldrick, 2007)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'Bruker Smart Apex CCD diffractometer'
_diffrn_measurement_method       \w-scans
_diffrn_detector_area_resol_mean 0.661
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14856
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         25.40
_reflns_number_total             4968
_reflns_number_gt                3863
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V 5.625 (Bruker, 1999)'
_computing_cell_refinement       'SMART V 5.625 (Bruker, 1999)'
_computing_data_reduction        'SAINT V 7.34A (Bruker, 2006)'
_computing_structure_solution    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'

_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^)+(0.0600P)^2^+0.6564P] 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         4968
_refine_ls_number_parameters     456
_refine_ls_number_restraints     139
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.049
_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
O1 O 0.59628(15) 0.62968(15) -0.06594(13) 0.0291(4) Uani 1 1 d . . .
O2 O 0.80344(16) 0.82751(16) -0.06993(13) 0.0284(4) Uani 1 1 d D . .
H2 H 0.721(2) 0.794(3) -0.102(2) 0.043 Uiso 1 1 d D . .
O3 O 0.87675(18) 0.97635(16) 0.13477(15) 0.0389(5) Uani 1 1 d . A .
C1 C 0.8940(2) 0.5485(2) 0.15997(18) 0.0250(5) Uani 1 1 d . . .
H1A H 0.9500 0.5402 0.2288 0.030 Uiso 1 1 calc R . .
H1B H 0.8656 0.4671 0.1109 0.030 Uiso 1 1 calc R . .
C2 C 0.7707(2) 0.5708(2) 0.19033(18) 0.0235(5) Uani 1 1 d . . .
H2A H 0.7283 0.5062 0.2392 0.028 Uiso 1 1 calc R . .
H2B H 0.7983 0.6561 0.2329 0.028 Uiso 1 1 calc R . .
N3 N 0.67237(18) 0.56322(18) 0.09199(15) 0.0239(4) Uani 1 1 d D . .
H3 H 0.599(2) 0.502(2) 0.080(2) 0.029 Uiso 1 1 d D . .
C3 C 0.6830(2) 0.6451(2) 0.01706(18) 0.0226(5) Uani 1 1 d . . .
C5 C 0.8078(2) 0.7690(2) 0.03052(17) 0.0224(5) Uani 1 1 d . A .
N6 N 1.04698(19) 0.83082(19) 0.01359(16) 0.0265(4) Uani 1 1 d D . .
H6 H 1.046(3) 0.893(2) -0.022(2) 0.032 Uiso 1 1 d D . .
C7 C 1.2844(2) 0.8440(3) 0.0099(2) 0.0340(6) Uani 1 1 d . . .
H7 H 1.3101 0.9184 -0.0279 0.041 Uiso 1 1 calc R . .
C8 C 1.3732(2) 0.7826(3) 0.0416(2) 0.0386(6) Uani 1 1 d . . .
H8 H 1.4616 0.8153 0.0248 0.046 Uiso 1 1 calc R . .
C9 C 1.3360(2) 0.6734(3) 0.0979(2) 0.0354(6) Uani 1 1 d . . .
H9 H 1.3998 0.6339 0.1191 0.043 Uiso 1 1 calc R . .
C10 C 1.2079(2) 0.6220(2) 0.12323(19) 0.0310(6) Uani 1 1 d . . .
H10 H 1.1832 0.5479 0.1616 0.037 Uiso 1 1 calc R . .
C11 C 1.1150(2) 0.6821(2) 0.09081(18) 0.0263(5) Uani 1 1 d . . .
C12 C 0.9765(2) 0.6543(2) 0.10174(18) 0.0235(5) Uani 1 1 d . . .
C13 C 0.9391(2) 0.7468(2) 0.05193(18) 0.0234(5) Uani 1 1 d . . .
C14 C 1.1553(2) 0.7923(2) 0.03570(19) 0.0286(5) Uani 1 1 d . . .
C15 C 0.8002(2) 0.8678(2) 0.12010(18) 0.0235(5) Uani 1 1 d . . .
O4 O 0.6967(2) 0.82314(18) 0.17226(19) 0.0323(5) Uani 0.925(4) 1 d PDU A 1
C16 C 0.6792(3) 0.9115(3) 0.2580(2) 0.0331(7) Uani 0.925(4) 1 d PDU A 1
H16A H 0.6989 0.9968 0.2311 0.040 Uiso 0.925(4) 1 calc PR A 1
H16B H 0.5845 0.8806 0.2698 0.040 Uiso 0.925(4) 1 calc PR A 1
C17 C 0.7665(5) 0.9231(5) 0.3642(3) 0.0717(13) Uani 0.925(4) 1 d PDU A 1
H17A H 0.7500 0.9811 0.4191 0.108 Uiso 0.925(4) 1 calc PR A 1
H17B H 0.8605 0.9572 0.3537 0.108 Uiso 0.925(4) 1 calc PR A 1
H17C H 0.7475 0.8389 0.3912 0.108 Uiso 0.925(4) 1 calc PR A 1
O4B O 0.752(3) 0.828(3) 0.215(2) 0.040(3) Uani 0.075(4) 1 d PDU A 2
C16B C 0.716(4) 0.843(3) 0.333(2) 0.043(3) Uani 0.075(4) 1 d PDU A 2
H16C H 0.6297 0.8573 0.3305 0.052 Uiso 0.075(4) 1 calc PR A 2
H16D H 0.7143 0.7691 0.3748 0.052 Uiso 0.075(4) 1 calc PR A 2
C17B C 0.833(5) 0.959(5) 0.378(4) 0.060(6) Uani 0.075(4) 1 d PDU A 2
H17D H 0.9077 0.9348 0.4116 0.090 Uiso 0.075(4) 1 calc PR A 2
H17E H 0.8085 1.0089 0.4350 0.090 Uiso 0.075(4) 1 calc PR A 2
H17F H 0.8602 1.0116 0.3174 0.090 Uiso 0.075(4) 1 calc PR A 2
O21 O 0.50270(14) 0.56678(14) 0.64164(12) 0.0244(4) Uani 1 1 d . . .
O22 O 0.45214(16) 0.72664(15) 0.77400(12) 0.0260(4) Uani 1 1 d D . .
H22 H 0.495(3) 0.675(2) 0.778(2) 0.039 Uiso 1 1 d D . .
O23 O 0.46858(17) 0.96049(15) 0.62148(13) 0.0308(4) Uani 1 1 d . A .
C21 C 0.2203(2) 0.6668(2) 0.41755(18) 0.0231(5) Uani 1 1 d . . .
H21A H 0.1802 0.7141 0.3658 0.028 Uiso 1 1 calc R . .
H21B H 0.1775 0.5746 0.3912 0.028 Uiso 1 1 calc R . .
C22 C 0.3700(2) 0.7076(2) 0.41333(18) 0.0235(5) Uani 1 1 d . . .
H22A H 0.3829 0.6972 0.3348 0.028 Uiso 1 1 calc R . .
H22B H 0.4134 0.7993 0.4414 0.028 Uiso 1 1 calc R . .
N23 N 0.43548(18) 0.63369(18) 0.47967(16) 0.0229(4) Uani 1 1 d D . .
H23 H 0.452(2) 0.576(2) 0.4430(19) 0.027 Uiso 1 1 d D . .
C24 C 0.4572(2) 0.6387(2) 0.58989(18) 0.0205(5) Uani 1 1 d . . .
C25 C 0.4220(2) 0.7393(2) 0.65956(18) 0.0214(5) Uani 1 1 d . A .
N26 N 0.20647(18) 0.73262(18) 0.71697(15) 0.0222(4) Uani 1 1 d D . .
H26 H 0.245(2) 0.747(2) 0.7848(15) 0.027 Uiso 1 1 d D . .
C27 C -0.0326(2) 0.7108(2) 0.7264(2) 0.0256(5) Uani 1 1 d . . .
H27 H -0.0221 0.7272 0.8052 0.031 Uiso 1 1 calc R . .
C28 C -0.1541(2) 0.6869(2) 0.6595(2) 0.0280(5) Uani 1 1 d . . .
H28 H -0.2290 0.6872 0.6930 0.034 Uiso 1 1 calc R . .
C29 C -0.1706(2) 0.6619(2) 0.5432(2) 0.0272(5) Uani 1 1 d . . .
H29 H -0.2559 0.6463 0.4995 0.033 Uiso 1 1 calc R . .
C30 C -0.0647(2) 0.6598(2) 0.4913(2) 0.0256(5) Uani 1 1 d . . .
H30 H -0.0765 0.6424 0.4125 0.031 Uiso 1 1 calc R . .
C31 C 0.0608(2) 0.68370(19) 0.55724(18) 0.0208(5) Uani 1 1 d . . .
C32 C 0.1899(2) 0.68990(19) 0.53185(17) 0.0201(5) Uani 1 1 d . . .
C33 C 0.2748(2) 0.71885(19) 0.63131(17) 0.0192(5) Uani 1 1 d . . .
C34 C 0.0747(2) 0.7099(2) 0.67335(18) 0.0218(5) Uani 1 1 d . . .
C35 C 0.5100(2) 0.8771(2) 0.64419(18) 0.0236(5) Uani 1 1 d . . .
O24 O 0.6382(2) 0.8918(2) 0.6658(2) 0.0327(6) Uani 0.925(4) 1 d PDU A 1
C36 C 0.7320(3) 1.0236(3) 0.6648(4) 0.0376(8) Uani 0.925(4) 1 d PDU A 1
H36A H 0.7161 1.0540 0.5910 0.045 Uiso 0.925(4) 1 calc PR A 1
H36B H 0.7187 1.0820 0.7226 0.045 Uiso 0.925(4) 1 calc PR A 1
C37 C 0.8671(3) 1.0210(3) 0.6873(3) 0.0453(8) Uani 0.925(4) 1 d PDU A 1
H37A H 0.9320 1.1073 0.6875 0.068 Uiso 0.925(4) 1 calc PR A 1
H37B H 0.8792 0.9634 0.6293 0.068 Uiso 0.925(4) 1 calc PR A 1
H37C H 0.8815 0.9906 0.7603 0.068 Uiso 0.925(4) 1 calc PR A 1
O24B O 0.632(3) 0.856(3) 0.628(3) 0.035(5) Uani 0.075(4) 1 d PDU A 2
C36B C 0.706(5) 0.995(4) 0.658(6) 0.036(4) Uani 0.075(4) 1 d PDU A 2
H36C H 0.6524 1.0463 0.6298 0.043 Uiso 0.075(4) 1 calc PR A 2
H36D H 0.7337 1.0158 0.7400 0.043 Uiso 0.075(4) 1 calc PR A 2
C37B C 0.820(3) 1.013(3) 0.602(4) 0.046(6) Uani 0.075(4) 1 d PDU A 2
H37D H 0.8974 1.0842 0.6431 0.069 Uiso 0.075(4) 1 calc PR A 2
H37E H 0.7991 1.0331 0.5260 0.069 Uiso 0.075(4) 1 calc PR A 2
H37F H 0.8423 0.9351 0.5997 0.069 Uiso 0.075(4) 1 calc PR A 2

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 0.0223(8) 0.0301(9) 0.0309(9) 0.0057(7) -0.0061(7) 0.0075(7)
O2 0.0243(9) 0.0334(9) 0.0268(9) 0.0097(7) 0.0029(7) 0.0086(7)
O3 0.0396(11) 0.0284(10) 0.0429(11) -0.0008(8) 0.0138(8) 0.0026(8)
C1 0.0242(12) 0.0274(12) 0.0237(11) 0.0025(9) -0.0020(9) 0.0115(10)
C2 0.0217(12) 0.0235(12) 0.0239(11) 0.0047(9) 0.0000(9) 0.0070(9)
N3 0.0175(10) 0.0218(10) 0.0287(10) 0.0045(8) -0.0010(8) 0.0036(8)
C3 0.0198(12) 0.0246(12) 0.0253(12) 0.0010(9) 0.0023(9) 0.0112(9)
C5 0.0228(12) 0.0232(11) 0.0215(11) 0.0044(9) 0.0028(9) 0.0085(9)
N6 0.0207(10) 0.0280(11) 0.0303(11) 0.0063(8) 0.0046(8) 0.0074(8)
C7 0.0240(13) 0.0435(15) 0.0331(14) 0.0047(11) 0.0057(10) 0.0093(11)
C8 0.0208(13) 0.0617(18) 0.0320(14) -0.0005(13) 0.0043(11) 0.0137(12)
C9 0.0266(14) 0.0546(17) 0.0290(13) -0.0051(12) -0.0004(10) 0.0226(12)
C10 0.0312(14) 0.0398(14) 0.0242(12) -0.0023(10) -0.0011(10) 0.0181(11)
C11 0.0234(12) 0.0338(13) 0.0214(11) -0.0037(10) -0.0001(9) 0.0123(10)
C12 0.0223(12) 0.0276(12) 0.0204(11) -0.0015(9) -0.0001(9) 0.0105(10)
C13 0.0203(12) 0.0256(12) 0.0215(11) -0.0020(9) 0.0017(9) 0.0058(9)
C14 0.0228(12) 0.0355(13) 0.0258(12) -0.0018(10) 0.0004(10) 0.0102(10)
C15 0.0198(12) 0.0233(12) 0.0287(12) 0.0076(9) 0.0035(9) 0.0088(10)
O4 0.0295(12) 0.0261(9) 0.0431(12) -0.0014(9) 0.0168(9) 0.0088(9)
C16 0.0383(15) 0.0299(14) 0.0385(14) 0.0010(11) 0.0177(11) 0.0174(12)
C17 0.091(3) 0.103(4) 0.0455(18) -0.008(2) 0.004(2) 0.071(3)
O4B 0.043(4) 0.034(4) 0.043(4) 0.001(4) 0.011(4) 0.015(4)
C16B 0.050(4) 0.043(4) 0.042(4) 0.000(4) 0.009(4) 0.024(4)
C17B 0.066(9) 0.065(8) 0.041(7) -0.006(6) -0.017(9) 0.022(7)
O21 0.0209(8) 0.0248(8) 0.0316(9) 0.0050(7) 0.0026(7) 0.0135(7)
O22 0.0258(9) 0.0302(9) 0.0241(8) 0.0039(7) -0.0014(7) 0.0146(7)
O23 0.0366(10) 0.0226(8) 0.0371(10) 0.0046(7) 0.0085(8) 0.0143(8)
C21 0.0269(12) 0.0210(11) 0.0228(11) 0.0036(9) 0.0010(9) 0.0110(9)
C22 0.0280(12) 0.0239(11) 0.0225(11) 0.0055(9) 0.0049(9) 0.0132(10)
N23 0.0243(10) 0.0223(10) 0.0268(10) 0.0022(8) 0.0061(8) 0.0136(8)
C24 0.0118(10) 0.0200(11) 0.0294(12) 0.0045(9) 0.0032(9) 0.0050(9)
C25 0.0196(11) 0.0223(11) 0.0233(11) 0.0027(9) 0.0008(9) 0.0098(9)
N26 0.0199(10) 0.0269(10) 0.0201(9) 0.0002(8) 0.0001(8) 0.0103(8)
C27 0.0223(12) 0.0252(12) 0.0310(13) 0.0005(10) 0.0055(10) 0.0105(10)
C28 0.0225(12) 0.0246(12) 0.0404(14) 0.0033(10) 0.0084(10) 0.0115(10)
C29 0.0179(12) 0.0247(12) 0.0396(14) 0.0043(10) -0.0005(10) 0.0101(10)
C30 0.0238(12) 0.0224(11) 0.0296(12) 0.0034(9) -0.0015(10) 0.0091(10)
C31 0.0200(11) 0.0154(10) 0.0287(12) 0.0035(9) 0.0026(9) 0.0085(9)
C32 0.0198(11) 0.0173(10) 0.0246(11) 0.0032(9) 0.0017(9) 0.0087(9)
C33 0.0191(11) 0.0160(10) 0.0251(11) 0.0021(8) 0.0036(9) 0.0094(9)
C34 0.0206(12) 0.0181(11) 0.0282(12) 0.0015(9) 0.0018(9) 0.0097(9)
C35 0.0229(12) 0.0244(12) 0.0245(12) -0.0006(9) 0.0037(9) 0.0101(10)
O24 0.0189(10) 0.0189(13) 0.0558(16) -0.0010(9) 0.0014(10) 0.0034(9)
C36 0.0264(18) 0.0203(17) 0.056(2) 0.0026(16) 0.0047(17) -0.0034(13)
C37 0.0284(15) 0.0306(15) 0.067(2) 0.0072(15) -0.0053(15) 0.0016(12)
O24B 0.021(7) 0.019(7) 0.057(8) 0.002(7) -0.006(7) 0.003(6)
C36B 0.024(6) 0.020(6) 0.056(6) 0.006(6) -0.007(6) 0.002(6)
C37B 0.038(9) 0.031(10) 0.058(11) 0.005(10) 0.004(8) -0.001(8)

_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 C3 1.239(3) . ?
O2 C5 1.420(3) . ?
O3 C15 1.201(3) . ?
C1 C12 1.497(3) . ?
C1 C2 1.517(3) . ?
C2 N3 1.463(3) . ?
N3 C3 1.316(3) . ?
C3 C5 1.549(3) . ?
C5 C13 1.504(3) . ?
C5 C15 1.539(3) . ?
N6 C14 1.371(3) . ?
N6 C13 1.378(3) . ?
C7 C8 1.379(4) . ?
C7 C14 1.396(3) . ?
C8 C9 1.399(4) . ?
C9 C10 1.385(3) . ?
C10 C11 1.408(3) . ?
C11 C14 1.402(3) . ?
C11 C12 1.439(3) . ?
C12 C13 1.374(3) . ?
C15 O4 1.318(3) . ?
C15 O4B 1.36(3) . ?
O4 C16 1.472(3) . ?
C16 C17 1.461(5) . ?
O4B C16B 1.55(2) . ?
C16B C17B 1.49(2) . ?
O21 C24 1.234(2) . ?
O22 C25 1.412(3) . ?
O23 C35 1.193(3) . ?
C21 C32 1.499(3) . ?
C21 C22 1.524(3) . ?
C22 N23 1.465(3) . ?
N23 C24 1.324(3) . ?
C24 C25 1.549(3) . ?
C25 C33 1.506(3) . ?
C25 C35 1.548(3) . ?
N26 C34 1.373(3) . ?
N26 C33 1.383(3) . ?
C27 C28 1.374(3) . ?
C27 C34 1.398(3) . ?
C28 C29 1.401(3) . ?
C29 C30 1.380(3) . ?
C30 C31 1.404(3) . ?
C31 C34 1.403(3) . ?
C31 C32 1.440(3) . ?
C32 C33 1.362(3) . ?
C35 O24 1.317(3) . ?
C35 O24B 1.45(4) . ?
O24 C36 1.479(3) . ?
C36 C37 1.451(5) . ?
O24B C36B 1.48(2) . ?
C36B C37B 1.44(2) . ?

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
C12 C1 C2 112.45(18) . . ?
N3 C2 C1 112.37(18) . . ?
C3 N3 C2 127.34(19) . . ?
O1 C3 N3 123.3(2) . . ?
O1 C3 C5 116.39(19) . . ?
N3 C3 C5 120.31(19) . . ?
O2 C5 C13 107.86(17) . . ?
O2 C5 C15 104.26(17) . . ?
C13 C5 C15 111.45(18) . . ?
O2 C5 C3 108.02(17) . . ?
C13 C5 C3 113.81(18) . . ?
C15 C5 C3 110.88(18) . . ?
C14 N6 C13 109.22(19) . . ?
C8 C7 C14 117.3(2) . . ?
C7 C8 C9 121.6(2) . . ?
C10 C9 C8 121.1(2) . . ?
C9 C10 C11 118.4(2) . . ?
C14 C11 C10 119.3(2) . . ?
C14 C11 C12 107.6(2) . . ?
C10 C11 C12 133.0(2) . . ?
C13 C12 C11 105.9(2) . . ?
C13 C12 C1 128.0(2) . . ?
C11 C12 C1 126.1(2) . . ?
C12 C13 N6 109.7(2) . . ?
C12 C13 C5 132.8(2) . . ?
N6 C13 C5 117.45(19) . . ?
N6 C14 C7 130.3(2) . . ?
N6 C14 C11 107.5(2) . . ?
C7 C14 C11 122.2(2) . . ?
O3 C15 O4 124.3(2) . . ?
O3 C15 O4B 111.9(12) . . ?
O3 C15 C5 122.5(2) . . ?
O4 C15 C5 113.06(19) . . ?
O4B C15 C5 119.5(12) . . ?
C15 O4 C16 117.2(2) . . ?
C17 C16 O4 112.3(3) . . ?
C15 O4B C16B 156(2) . . ?
C17B C16B O4B 97(2) . . ?
C32 C21 C22 113.40(18) . . ?
N23 C22 C21 112.66(18) . . ?
C24 N23 C22 126.63(19) . . ?
O21 C24 N23 124.1(2) . . ?
O21 C24 C25 117.20(19) . . ?
N23 C24 C25 118.67(18) . . ?
O22 C25 C33 108.70(17) . . ?
O22 C25 C35 105.58(17) . . ?
C33 C25 C35 111.46(17) . . ?
O22 C25 C24 108.88(17) . . ?
C33 C25 C24 110.54(17) . . ?
C35 C25 C24 111.50(17) . . ?
C34 N26 C33 109.12(18) . . ?
C28 C27 C34 117.1(2) . . ?
C27 C28 C29 121.8(2) . . ?
C30 C29 C28 121.0(2) . . ?
C29 C30 C31 118.7(2) . . ?
C34 C31 C30 119.1(2) . . ?
C34 C31 C32 107.54(18) . . ?
C30 C31 C32 133.4(2) . . ?
C33 C32 C31 106.29(18) . . ?
C33 C32 C21 128.2(2) . . ?
C31 C32 C21 125.47(19) . . ?
C32 C33 N26 109.77(19) . . ?
C32 C33 C25 131.6(2) . . ?
N26 C33 C25 118.58(18) . . ?
N26 C34 C27 130.3(2) . . ?
N26 C34 C31 107.26(19) . . ?
C27 C34 C31 122.4(2) . . ?
O23 C35 O24 124.4(2) . . ?
O23 C35 O24B 131.9(13) . . ?
O23 C35 C25 125.0(2) . . ?
O24 C35 C25 110.51(19) . . ?
O24B C35 C25 99.9(12) . . ?
C35 O24 C36 115.1(3) . . ?
C37 C36 O24 107.4(3) . . ?
C35 O24B C36B 89(2) . . ?
C37B C36B O24B 101(2) . . ?

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
O2 H2 O1 0.86(2) 1.99(3) 2.560(2) 123(2) .
N3 H3 O1 0.839(17) 2.090(18) 2.922(2) 171(2) 2_665
N6 H6 O3 0.847(17) 2.09(2) 2.866(3) 151(2) 2_775
O22 H22 O21 0.85(2) 2.03(3) 2.582(2) 122(2) .
O22 H22 O1 0.85(2) 2.23(3) 2.815(2) 126(2) 1_556
N23 H23 O21 0.843(17) 2.083(18) 2.926(2) 178(2) 2_666

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.053

# Attachment '238MAR08.cif'

data_238MAR08
_database_code_depnum_ccdc_archive 'CCDC 711468'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N2 O4'
_chemical_formula_sum            'C18 H18 N2 O4'
_chemical_formula_weight         326.34

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.7516(16)
_cell_length_b                   17.835(3)
_cell_length_c                   8.8391(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.635(2)
_cell_angle_gamma                90.00
_cell_volume                     1537.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4286
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      24.74

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.172
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_max          0.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9566
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_process_details   '(Sheldrick, 2000)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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  'Bruker Smart Apex CCD diffractometer'
_diffrn_measurement_method       \w-scans
_diffrn_detector_area_resol_mean 0.661
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12291
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2819
_reflns_number_gt                1953
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V 5.625 (Bruker, 1999)'
_computing_cell_refinement       'SMART V 5.625 (Bruker, 1999)'
_computing_data_reduction        'SAINT V 7.34A (Bruker, 2006)'
_computing_structure_solution    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'

_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^)+(0.0339P)^2^] 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         2819
_refine_ls_number_parameters     297
_refine_ls_number_restraints     171
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0817
_refine_ls_wR_factor_gt          0.0751
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_restrained_S_all      0.907
_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
O2 O 0.60532(12) 0.57582(6) 0.47864(13) 0.0527(3) Uani 1 1 d . A .
C1 C 0.8060(19) 0.4308(10) -0.0887(17) 0.046(2) Uani 0.50(4) 1 d PDU A 1
H1A H 0.8582 0.4638 -0.1537 0.055 Uiso 0.50(4) 1 calc PR A 1
H1B H 0.7303 0.4104 -0.1475 0.055 Uiso 0.50(4) 1 calc PR A 1
O1 O 0.7100(12) 0.2634(5) 0.2441(15) 0.048(3) Uani 0.50(4) 1 d PDU A 1
C2 C 0.8971(19) 0.3676(10) -0.033(2) 0.047(2) Uani 0.50(4) 1 d PDU A 1
H2A H 0.9432 0.3448 -0.1181 0.056 Uiso 0.50(4) 1 calc PR A 1
H2B H 0.9665 0.3874 0.0356 0.056 Uiso 0.50(4) 1 calc PR A 1
N3 N 0.817(2) 0.3113(11) 0.0445(14) 0.045(2) Uani 0.50(4) 1 d PDU A 1
H3 H 0.782(5) 0.2752(19) -0.011(5) 0.067 Uiso 0.50(4) 1 d PD A 1
C1B C 0.835(2) 0.4336(10) -0.0757(17) 0.047(2) Uani 0.50(4) 1 d PDU A 2
H1C H 0.7722 0.4136 -0.1518 0.057 Uiso 0.50(4) 1 calc PR A 2
H1D H 0.8939 0.4694 -0.1252 0.057 Uiso 0.50(4) 1 calc PR A 2
O1B O 0.7073(13) 0.2615(6) 0.2342(18) 0.069(4) Uani 0.50(4) 1 d PDU A 2
C2B C 0.9210(19) 0.3706(11) -0.015(2) 0.046(2) Uani 0.50(4) 1 d PDU A 2
H2C H 0.9718 0.3489 -0.0981 0.056 Uiso 0.50(4) 1 calc PR A 2
H2D H 0.9871 0.3910 0.0566 0.056 Uiso 0.50(4) 1 calc PR A 2
N3B N 0.844(2) 0.3118(11) 0.0583(15) 0.045(2) Uani 0.50(4) 1 d PDU A 2
H3B H 0.832(5) 0.2701(19) 0.007(5) 0.068 Uiso 0.50(4) 1 d PD A 2
C4 C 0.77241(18) 0.31519(9) 0.18683(19) 0.0422(4) Uani 1 1 d D . .
C5 C 0.79108(15) 0.38853(8) 0.27816(16) 0.0364(4) Uani 1 1 d D A .
C5A C 0.74408(15) 0.45667(8) 0.18974(17) 0.0362(4) Uani 1 1 d . . .
N6 N 0.67183(13) 0.51483(6) 0.26666(14) 0.0381(3) Uani 1 1 d . A .
C6 C 0.63331(16) 0.56913(8) 0.15885(18) 0.0399(4) Uani 1 1 d . . .
C7 C 0.56104(17) 0.63571(9) 0.1738(2) 0.0508(5) Uani 1 1 d . A .
H7 H 0.5290 0.6517 0.2671 0.061 Uiso 1 1 calc R . .
C8 C 0.53899(19) 0.67697(10) 0.0442(2) 0.0617(5) Uani 1 1 d . . .
H8 H 0.4909 0.7219 0.0505 0.074 Uiso 1 1 calc R A .
C9 C 0.5861(2) 0.65367(10) -0.0953(2) 0.0643(5) Uani 1 1 d . A .
H9 H 0.5699 0.6833 -0.1802 0.077 Uiso 1 1 calc R . .
C10 C 0.6567(2) 0.58734(9) -0.1101(2) 0.0560(5) Uani 1 1 d . . .
H10 H 0.6871 0.5713 -0.2041 0.067 Uiso 1 1 calc R A .
C10A C 0.68124(16) 0.54485(8) 0.01942(18) 0.0429(4) Uani 1 1 d . A .
C10B C 0.75177(17) 0.47434(8) 0.04185(17) 0.0412(4) Uani 1 1 d D A .
C11 C 0.70544(17) 0.38317(9) 0.42371(17) 0.0438(4) Uani 1 1 d . . .
H11A H 0.6112 0.3712 0.3972 0.053 Uiso 1 1 calc R A .
H11B H 0.7411 0.3431 0.4870 0.053 Uiso 1 1 calc R . .
C12 C 0.70955(17) 0.45600(9) 0.51104(17) 0.0452(4) Uani 1 1 d . A .
H12A H 0.6551 0.4507 0.6016 0.054 Uiso 1 1 calc R . .
H12B H 0.8034 0.4662 0.5424 0.054 Uiso 1 1 calc R . .
C13 C 0.65699(16) 0.52050(9) 0.42173(17) 0.0403(4) Uani 1 1 d . . .
C14 C 0.94074(17) 0.39520(10) 0.32884(18) 0.0445(4) Uani 1 1 d D . .
O3 O 0.9883(3) 0.32583(16) 0.3663(3) 0.0503(7) Uani 0.797(6) 1 d PDU A 1
O4 O 1.0043(9) 0.4525(4) 0.3400(9) 0.0544(12) Uani 0.797(6) 1 d PDU A 1
C15 C 1.1224(3) 0.3200(2) 0.4411(3) 0.0583(9) Uani 0.797(6) 1 d PDU A 1
H15A H 1.1829 0.3587 0.4032 0.070 Uiso 0.797(6) 1 calc PR A 1
H15B H 1.1630 0.2716 0.4192 0.070 Uiso 0.797(6) 1 calc PR A 1
C16 C 1.1064(4) 0.3287(3) 0.6074(3) 0.0789(12) Uani 0.797(6) 1 d PDU A 1
H16A H 1.1943 0.3236 0.6564 0.118 Uiso 0.797(6) 1 calc PR A 1
H16B H 1.0454 0.2908 0.6442 0.118 Uiso 0.797(6) 1 calc PR A 1
H16C H 1.0693 0.3773 0.6288 0.118 Uiso 0.797(6) 1 calc PR A 1
O3B O 0.9779(14) 0.3419(7) 0.4176(14) 0.059(3) Uani 0.203(6) 1 d PDU A 2
O4B O 1.014(4) 0.4488(15) 0.304(4) 0.061(6) Uani 0.203(6) 1 d PDU A 2
C15B C 1.1144(14) 0.3520(7) 0.4840(19) 0.061(2) Uani 0.203(6) 1 d PDU A 2
H15C H 1.1146 0.3928 0.5565 0.073 Uiso 0.203(6) 1 calc PR A 2
H15D H 1.1809 0.3628 0.4062 0.073 Uiso 0.203(6) 1 calc PR A 2
C16B C 1.1463(12) 0.2804(7) 0.5593(19) 0.074(3) Uani 0.203(6) 1 d PDU A 2
H16D H 1.2397 0.2810 0.5948 0.111 Uiso 0.203(6) 1 calc PR A 2
H16E H 1.1339 0.2399 0.4887 0.111 Uiso 0.203(6) 1 calc PR A 2
H16F H 1.0862 0.2735 0.6434 0.111 Uiso 0.203(6) 1 calc PR A 2

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
O2 0.0611(8) 0.0490(7) 0.0481(7) -0.0123(6) 0.0080(6) 0.0005(6)
C1 0.058(4) 0.044(3) 0.036(3) 0.003(2) 0.003(3) -0.003(3)
O1 0.078(6) 0.019(4) 0.048(4) 0.006(3) -0.005(4) -0.006(4)
C2 0.056(5) 0.047(3) 0.037(3) -0.005(3) 0.005(3) 0.001(3)
N3 0.062(6) 0.035(2) 0.036(3) -0.004(2) -0.005(3) -0.005(3)
C1B 0.064(5) 0.047(3) 0.031(3) -0.003(2) 0.002(4) -0.003(3)
O1B 0.075(6) 0.059(6) 0.075(6) 0.000(4) 0.016(5) -0.022(5)
C2B 0.056(4) 0.045(3) 0.039(3) -0.003(3) 0.009(3) 0.000(3)
N3B 0.057(5) 0.034(2) 0.045(3) -0.007(3) 0.005(4) 0.000(3)
C4 0.0495(11) 0.0339(10) 0.0429(11) 0.0035(8) -0.0034(9) 0.0016(8)
C5 0.0422(9) 0.0339(8) 0.0331(9) 0.0032(7) 0.0005(7) -0.0041(7)
C5A 0.0434(9) 0.0318(8) 0.0335(9) -0.0016(7) 0.0022(7) -0.0028(7)
N6 0.0479(8) 0.0345(7) 0.0319(7) -0.0013(6) 0.0004(6) -0.0004(6)
C6 0.0463(10) 0.0343(9) 0.0390(9) 0.0021(7) -0.0038(8) -0.0006(8)
C7 0.0531(11) 0.0453(10) 0.0539(11) -0.0003(9) -0.0023(9) 0.0044(9)
C8 0.0665(13) 0.0474(11) 0.0712(14) 0.0071(10) -0.0079(11) 0.0128(10)
C9 0.0810(15) 0.0544(12) 0.0572(13) 0.0177(10) -0.0126(11) 0.0047(11)
C10 0.0784(14) 0.0477(11) 0.0418(11) 0.0082(9) -0.0015(10) -0.0005(10)
C10A 0.0551(11) 0.0359(9) 0.0377(10) 0.0031(8) -0.0021(8) -0.0034(8)
C10B 0.0560(11) 0.0347(9) 0.0329(9) -0.0007(7) 0.0021(8) -0.0013(8)
C11 0.0494(10) 0.0427(9) 0.0394(10) 0.0074(8) 0.0025(8) -0.0012(8)
C12 0.0501(10) 0.0539(10) 0.0318(9) 0.0005(8) 0.0027(8) -0.0034(8)
C13 0.0409(10) 0.0425(10) 0.0374(10) -0.0058(8) 0.0012(8) -0.0084(8)
C14 0.0498(11) 0.0490(11) 0.0348(10) 0.0030(9) 0.0030(8) -0.0051(9)
O3 0.0476(11) 0.0502(13) 0.0528(15) 0.0047(10) -0.0129(12) 0.0013(9)
O4 0.052(2) 0.0568(17) 0.054(3) -0.0040(15) 0.002(2) -0.0192(14)
C15 0.0447(14) 0.068(2) 0.0616(18) 0.0001(15) -0.0116(14) 0.0001(16)
C16 0.073(2) 0.105(3) 0.0579(17) 0.0165(19) -0.0141(15) -0.028(2)
O3B 0.049(4) 0.065(5) 0.062(5) 0.016(4) -0.015(4) -0.010(4)
O4B 0.066(7) 0.062(8) 0.057(13) 0.004(7) 0.018(8) -0.024(6)
C15B 0.046(4) 0.066(5) 0.071(5) 0.005(4) -0.019(4) -0.004(5)
C16B 0.054(6) 0.069(6) 0.099(8) 0.014(6) -0.021(5) 0.006(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
O2 C13 1.2189(17) . ?
C1 C10B 1.493(10) . ?
C1 C2 1.514(9) . ?
O1 C4 1.219(8) . ?
C2 N3 1.449(9) . ?
N3 C4 1.337(10) . ?
C1B C2B 1.499(9) . ?
C1B C10B 1.509(10) . ?
O1B C4 1.225(8) . ?
C2B N3B 1.445(9) . ?
N3B C4 1.344(9) . ?
C4 C5 1.547(2) . ?
C5 C5A 1.513(2) . ?
C5 C14 1.527(2) . ?
C5 C11 1.544(2) . ?
C5A C10B 1.348(2) . ?
C5A N6 1.4300(18) . ?
N6 C13 1.3836(18) . ?
N6 C6 1.4068(18) . ?
C6 C7 1.388(2) . ?
C6 C10A 1.392(2) . ?
C7 C8 1.377(2) . ?
C8 C9 1.384(2) . ?
C9 C10 1.375(2) . ?
C10 C10A 1.392(2) . ?
C10A C10B 1.446(2) . ?
C11 C12 1.511(2) . ?
C12 C13 1.483(2) . ?
C14 O4 1.199(5) . ?
C14 O4B 1.214(16) . ?
C14 O3B 1.282(11) . ?
C14 O3 1.361(3) . ?
O3 C15 1.463(3) . ?
C15 C16 1.488(4) . ?
O3B C15B 1.460(13) . ?
C15B C16B 1.472(14) . ?

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
C10B C1 C2 110.3(12) . . ?
N3 C2 C1 110.6(10) . . ?
C4 N3 C2 126.2(14) . . ?
C2B C1B C10B 114.7(12) . . ?
N3B C2B C1B 114.3(10) . . ?
C4 N3B C2B 128.7(14) . . ?
O1 C4 N3 121.3(10) . . ?
O1B C4 N3 117.1(12) . . ?
O1 C4 N3B 125.8(11) . . ?
O1B C4 N3B 122.1(10) . . ?
O1 C4 C5 118.7(7) . . ?
O1B C4 C5 122.8(8) . . ?
N3 C4 C5 119.8(8) . . ?
N3B C4 C5 114.8(9) . . ?
C5A C5 C14 111.84(12) . . ?
C5A C5 C11 108.45(12) . . ?
C14 C5 C11 106.53(13) . . ?
C5A C5 C4 112.11(12) . . ?
C14 C5 C4 109.01(13) . . ?
C11 C5 C4 108.71(12) . . ?
C10B C5A N6 108.95(13) . . ?
C10B C5A C5 131.99(14) . . ?
N6 C5A C5 119.01(12) . . ?
C13 N6 C6 126.20(13) . . ?
C13 N6 C5A 125.56(13) . . ?
C6 N6 C5A 107.85(12) . . ?
C7 C6 C10A 121.77(15) . . ?
C7 C6 N6 131.02(15) . . ?
C10A C6 N6 107.21(13) . . ?
C8 C7 C6 116.90(17) . . ?
C7 C8 C9 122.03(17) . . ?
C10 C9 C8 120.97(17) . . ?
C9 C10 C10A 118.14(17) . . ?
C10 C10A C6 120.17(15) . . ?
C10 C10A C10B 131.59(15) . . ?
C6 C10A C10B 108.24(13) . . ?
C5A C10B C10A 107.74(13) . . ?
C5A C10B C1 130.7(8) . . ?
C10A C10B C1 121.2(8) . . ?
C5A C10B C1B 126.2(7) . . ?
C10A C10B C1B 125.6(7) . . ?
C12 C11 C5 111.15(12) . . ?
C13 C12 C11 112.81(13) . . ?
O2 C13 N6 121.08(15) . . ?
O2 C13 C12 123.37(14) . . ?
N6 C13 C12 115.54(14) . . ?
O4 C14 O3B 116.1(8) . . ?
O4B C14 O3B 122(2) . . ?
O4 C14 O3 125.5(5) . . ?
O4B C14 O3 124(2) . . ?
O4 C14 C5 125.6(5) . . ?
O4B C14 C5 125(2) . . ?
O3B C14 C5 112.6(6) . . ?
O3 C14 C5 108.81(19) . . ?
C14 O3 C15 118.4(3) . . ?
O3 C15 C16 109.7(2) . . ?
C14 O3B C15B 113.9(10) . . ?
O3B C15B C16B 105.2(10) . . ?

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
C10B C1 C2 N3 68.2(14) . . . . ?
C1 C2 N3 C4 -79.7(18) . . . . ?
C10B C1B C2B N3B 59.9(16) . . . . ?
C1B C2B N3B C4 -66.3(19) . . . . ?
C2 N3 C4 O1 -176.9(11) . . . . ?
C2 N3 C4 O1B -178.9(12) . . . . ?
C2 N3 C4 N3B -62(7) . . . . ?
C2 N3 C4 C5 7.4(18) . . . . ?
C2B N3B C4 O1 -179.7(11) . . . . ?
C2B N3B C4 O1B 177.1(12) . . . . ?
C2B N3B C4 N3 107(8) . . . . ?
C2B N3B C4 C5 -9.2(17) . . . . ?
O1 C4 C5 C5A -127.3(7) . . . . ?
O1B C4 C5 C5A -124.9(8) . . . . ?
N3 C4 C5 C5A 48.5(11) . . . . ?
N3B C4 C5 C5A 61.5(10) . . . . ?
O1 C4 C5 C14 108.3(7) . . . . ?
O1B C4 C5 C14 110.8(8) . . . . ?
N3 C4 C5 C14 -75.9(11) . . . . ?
N3B C4 C5 C14 -62.8(10) . . . . ?
O1 C4 C5 C11 -7.4(7) . . . . ?
O1B C4 C5 C11 -5.0(8) . . . . ?
N3 C4 C5 C11 168.4(11) . . . . ?
N3B C4 C5 C11 -178.6(10) . . . . ?
C14 C5 C5A C10B 86.2(2) . . . . ?
C11 C5 C5A C10B -156.63(17) . . . . ?
C4 C5 C5A C10B -36.6(2) . . . . ?
C14 C5 C5A N6 -96.93(16) . . . . ?
C11 C5 C5A N6 20.25(18) . . . . ?
C4 C5 C5A N6 140.28(14) . . . . ?
C10B C5A N6 C13 -172.39(14) . . . . ?
C5 C5A N6 C13 10.1(2) . . . . ?
C10B C5A N6 C6 0.77(17) . . . . ?
C5 C5A N6 C6 -176.77(12) . . . . ?
C13 N6 C6 C7 -7.5(3) . . . . ?
C5A N6 C6 C7 179.39(16) . . . . ?
C13 N6 C6 C10A 172.93(14) . . . . ?
C5A N6 C6 C10A -0.17(16) . . . . ?
C10A C6 C7 C8 -0.1(2) . . . . ?
N6 C6 C7 C8 -179.64(16) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C9 C10 C10A -1.0(3) . . . . ?
C9 C10 C10A C6 0.9(3) . . . . ?
C9 C10 C10A C10B -179.46(17) . . . . ?
C7 C6 C10A C10 -0.3(2) . . . . ?
N6 C6 C10A C10 179.27(15) . . . . ?
C7 C6 C10A C10B 179.95(14) . . . . ?
N6 C6 C10A C10B -0.44(17) . . . . ?
N6 C5A C10B C10A -1.03(17) . . . . ?
C5 C5A C10B C10A 176.08(15) . . . . ?
N6 C5A C10B C1 -174.7(10) . . . . ?
C5 C5A C10B C1 2.4(10) . . . . ?
N6 C5A C10B C1B 171.6(10) . . . . ?
C5 C5A C10B C1B -11.3(10) . . . . ?
C10 C10A C10B C5A -178.73(18) . . . . ?
C6 C10A C10B C5A 0.93(18) . . . . ?
C10 C10A C10B C1 -4.3(9) . . . . ?
C6 C10A C10B C1 175.3(9) . . . . ?
C10 C10A C10B C1B 8.5(10) . . . . ?
C6 C10A C10B C1B -171.8(10) . . . . ?
C2 C1 C10B C5A -17.5(14) . . . . ?
C2 C1 C10B C10A 169.5(6) . . . . ?
C2 C1 C10B C1B 54(7) . . . . ?
C2B C1B C10B C5A -3.8(15) . . . . ?
C2B C1B C10B C10A 167.6(7) . . . . ?
C2B C1B C10B C1 -121(8) . . . . ?
C5A C5 C11 C12 -52.84(16) . . . . ?
C14 C5 C11 C12 67.70(16) . . . . ?
C4 C5 C11 C12 -174.97(12) . . . . ?
C5 C11 C12 C13 58.88(18) . . . . ?
C6 N6 C13 O2 0.8(2) . . . . ?
C5A N6 C13 O2 172.70(14) . . . . ?
C6 N6 C13 C12 -178.38(14) . . . . ?
C5A N6 C13 C12 -6.5(2) . . . . ?
C11 C12 C13 O2 152.75(15) . . . . ?
C11 C12 C13 N6 -28.11(19) . . . . ?
C5A C5 C14 O4 20.8(5) . . . . ?
C11 C5 C14 O4 -97.6(5) . . . . ?
C4 C5 C14 O4 145.3(5) . . . . ?
C5A C5 C14 O4B 1.0(19) . . . . ?
C11 C5 C14 O4B -117.4(19) . . . . ?
C4 C5 C14 O4B 125.5(19) . . . . ?
C5A C5 C14 O3B 172.9(7) . . . . ?
C11 C5 C14 O3B 54.6(7) . . . . ?
C4 C5 C14 O3B -62.6(7) . . . . ?
C5A C5 C14 O3 -162.11(18) . . . . ?
C11 C5 C14 O3 79.6(2) . . . . ?
C4 C5 C14 O3 -37.6(2) . . . . ?
O4 C14 O3 C15 6.8(6) . . . . ?
O4B C14 O3 C15 26.5(19) . . . . ?
O3B C14 O3 C15 -66.7(18) . . . . ?
C5 C14 O3 C15 -170.3(2) . . . . ?
C14 O3 C15 C16 86.3(5) . . . . ?
O4 C14 O3B C15B -17.3(13) . . . . ?
O4B C14 O3B C15B 0(2) . . . . ?
O3 C14 O3B C15B 102(2) . . . . ?
C5 C14 O3B C15B -172.2(8) . . . . ?
C14 O3B C15B C16B -170.7(16) . . . . ?

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
N3 H3 O1 0.88(2) 2.37(4) 3.14(2) 147(4) 4_565
N3B H3B O3B 0.88(2) 2.58(4) 3.29(2) 138(4) 4_565

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.029