# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011
data_global
_journal_name_full Org.Biomol.Chem.
_journal_coden_cambridge 0177
_journal_year ?
_journal_volume ?
_journal_page_first ?
loop_
_publ_author_address
;
FIRST AUTHORS ADDRESS
;
_publ_contact_author
;
Madeleine Helliwell
;
_publ_contact_author_email madeleine.helliwell@manchester.ac.uk
_publ_contact_author_fax ' ENTER FAX NUMBER '
_publ_contact_author_phone ' ENTER PHONE NUMBER '
_publ_contact_letter
;
ENTER TEXT OF LETTER
;
_publ_requested_coeditor_name ?
_publ_section_title
;
ENTER SECTION TITLE
;
loop_
_publ_author_name
'Znabet, Anass'
'Blanken, Sara'
'Janssen, Elwin'
'de Kanter, Frans'
'Helliwell, Madeleine'
'Turner, Nicholas'
'Ruijter, E.'
'Orru, Romano'
data_anas2bm
_database_code_depnum_ccdc_archive 'CCDC 844264'
#TrackingRef 'anas2bm.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_publ_section_abstract
;
ENTER ABSTRACT
;
_publ_section_exptl_prep
;
ENTER EXPERIMENTAL SECTION
;
_publ_section_exptl_refinement
;
The structure was solved by the direct methods.
All non-H atoms were refined anisotropically.
H atoms were included in calculated positions,
except H3 which was found by difference Fourier methods
and refined with Ueq value 1.2 times that of the parent atom.
The absolute configuration was input.
;
_publ_section_comment
;
ENTER TEXT
;
_publ_section_references
;
Bruker (2001). SMART (Version 5.625), SADABS (Version 2.03a) and
SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2002). SAINT. Version 6.36a. Bruker AXS Inc., Madison,
Wisconsin, USA.
M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini,
G. L. Cascarano, L. De Caro,C. Giacovazzo, G. Polidori
and R. Spagna
SIR2004: an improved tool for crystal structure determination
and refinement
J. Appl. Cryst. (2005). 38, 381-388
Sheldrick, G. M. (1997). SHELXS-97 and SHELXL-97.
University of G\"ottingen, Germany.
Sheldrick, G, M. (2005). CELL_NOW. University
of G\"ottingen, Germany.
Sheldrick, G, M. (2007). TWINABS. University
of G\"ottingen, Germany.
Spek, A.L. (2003) J.Appl.Cryst. 36, 2003, 7-13.
;
_publ_section_acknowledgements
;
ENTER ACKNOWLEDGEMENTS
;
_publ_section_table_legends
;
ENTER TABLE LEGENDS
;
_publ_section_figure_captions
;
ENTER FIGURE CAPTIONS
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C20 H25 N3 O3'
_chemical_formula_sum 'C20 H25 N3 O3'
_chemical_formula_weight 355.43
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 Orthorhombic
_symmetry_space_group_name_H-M P212121
_symmetry_space_group_name_Hall P2ac2ab
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 9.681(3)
_cell_length_b 12.864(4)
_cell_length_c 14.899(5)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1855.4(11)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 798
_cell_measurement_theta_min 2.51
_cell_measurement_theta_max 22.62
_exptl_crystal_description irregular
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.50
_exptl_crystal_size_mid 0.35
_exptl_crystal_size_min 0.15
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.272
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 760
_exptl_absorpt_coefficient_mu 0.087
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_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 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 7181
_diffrn_reflns_av_R_equivalents 0.0685
_diffrn_reflns_av_sigmaI/netI 0.0591
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_theta_min 2.09
_diffrn_reflns_theta_max 25.02
_reflns_number_total 1882
_reflns_number_gt 1668
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker SMART'
_computing_cell_refinement 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_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^)+(0.0302P)^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
_chemical_absolute_configuration syn
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 1882
_refine_ls_number_parameters 241
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0711
_refine_ls_R_factor_gt 0.0592
_refine_ls_wR_factor_ref 0.0970
_refine_ls_wR_factor_gt 0.0941
_refine_ls_goodness_of_fit_ref 1.278
_refine_ls_restrained_S_all 1.278
_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 0.4406(3) 0.3427(2) 0.0461(2) 0.0429(8) Uani 1 1 d . . .
O2 O 0.6329(3) 0.3380(2) -0.02992(19) 0.0350(7) Uani 1 1 d . . .
O3 O 1.1386(2) 0.54808(19) -0.01454(17) 0.0261(6) Uani 1 1 d . . .
N1 N 0.8229(3) 0.4547(2) 0.0883(2) 0.0181(7) Uani 1 1 d . . .
N2 N 0.5504(3) 0.3817(3) 0.0215(2) 0.0294(8) Uani 1 1 d . . .
N3 N 0.9594(3) 0.4544(2) -0.0720(2) 0.0200(7) Uani 1 1 d . . .
C1 C 0.9678(3) 0.4880(3) 0.0879(2) 0.0176(8) Uani 1 1 d . . .
H1 H 0.9752 0.5558 0.1204 0.021 Uiso 1 1 calc R . .
C2 C 1.0458(4) 0.4042(3) 0.1417(2) 0.0221(9) Uani 1 1 d . . .
H2 H 1.1203 0.3728 0.1040 0.026 Uiso 1 1 calc R . .
C3 C 0.9401(4) 0.3199(3) 0.1694(2) 0.0212(9) Uani 1 1 d . . .
H3 H 0.9711 0.2510 0.1456 0.025 Uiso 1 1 calc R . .
C4 C 0.8032(4) 0.3497(3) 0.1252(2) 0.0217(9) Uani 1 1 d . . .
H4A H 0.7799 0.3000 0.0767 0.026 Uiso 1 1 calc R . .
H4B H 0.7276 0.3494 0.1699 0.026 Uiso 1 1 calc R . .
C5 C 1.1058(4) 0.4399(3) 0.2330(3) 0.0276(9) Uani 1 1 d . . .
H5 H 1.1959 0.4777 0.2303 0.033 Uiso 1 1 calc R . .
C6 C 0.9910(4) 0.4942(3) 0.2834(2) 0.0287(10) Uani 1 1 d . . .
H6 H 0.9854 0.5665 0.2957 0.034 Uiso 1 1 calc R . .
C7 C 0.8997(4) 0.4228(3) 0.3074(3) 0.0282(10) Uani 1 1 d . . .
H7 H 0.8171 0.4346 0.3402 0.034 Uiso 1 1 calc R . .
C8 C 0.9507(4) 0.3193(3) 0.2730(3) 0.0266(9) Uani 1 1 d . . .
H8 H 0.9118 0.2566 0.3036 0.032 Uiso 1 1 calc R . .
C9 C 1.1075(4) 0.3353(3) 0.2834(3) 0.0305(10) Uani 1 1 d . . .
H9A H 1.1370 0.3420 0.3467 0.037 Uiso 1 1 calc R . .
H9B H 1.1627 0.2813 0.2525 0.037 Uiso 1 1 calc R . .
C10 C 0.7177(4) 0.5211(3) 0.0648(2) 0.0160(8) Uani 1 1 d . . .
C11 C 0.5811(4) 0.4890(3) 0.0466(2) 0.0201(8) Uani 1 1 d . . .
C12 C 0.4718(4) 0.5581(3) 0.0387(2) 0.0246(9) Uani 1 1 d . . .
H12 H 0.3802 0.5329 0.0317 0.030 Uiso 1 1 calc R . .
C13 C 0.4968(4) 0.6636(3) 0.0409(3) 0.0274(9) Uani 1 1 d . . .
H13 H 0.4226 0.7118 0.0377 0.033 Uiso 1 1 calc R . .
C14 C 0.6315(4) 0.6981(3) 0.0479(2) 0.0258(9) Uani 1 1 d . . .
H14 H 0.6502 0.7705 0.0441 0.031 Uiso 1 1 calc R . .
C15 C 0.7393(4) 0.6299(3) 0.0602(2) 0.0199(8) Uani 1 1 d . . .
H15 H 0.8305 0.6564 0.0657 0.024 Uiso 1 1 calc R . .
C16 C 1.0286(4) 0.5005(3) -0.0050(2) 0.0207(8) Uani 1 1 d . . .
C17 C 1.0059(4) 0.4423(3) -0.1652(2) 0.0222(8) Uani 1 1 d . . .
C18 C 0.8972(4) 0.3773(3) -0.2129(3) 0.0294(10) Uani 1 1 d . . .
H18A H 0.8900 0.3092 -0.1836 0.044 Uiso 1 1 calc R . .
H18B H 0.9238 0.3678 -0.2758 0.044 Uiso 1 1 calc R . .
H18C H 0.8078 0.4128 -0.2099 0.044 Uiso 1 1 calc R . .
C19 C 1.1441(4) 0.3855(3) -0.1666(3) 0.0336(10) Uani 1 1 d . . .
H19A H 1.2145 0.4286 -0.1375 0.050 Uiso 1 1 calc R . .
H19B H 1.1712 0.3718 -0.2288 0.050 Uiso 1 1 calc R . .
H19C H 1.1353 0.3195 -0.1342 0.050 Uiso 1 1 calc R . .
C20 C 1.0187(4) 0.5500(3) -0.2088(2) 0.0246(9) Uani 1 1 d . . .
H20A H 0.9305 0.5869 -0.2035 0.037 Uiso 1 1 calc R . .
H20B H 1.0425 0.5421 -0.2723 0.037 Uiso 1 1 calc R . .
H20C H 1.0911 0.5898 -0.1783 0.037 Uiso 1 1 calc R . .
H3N H 0.887(4) 0.425(3) -0.059(3) 0.029 Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0275(16) 0.0335(18) 0.068(2) 0.0086(15) -0.0079(16) -0.0149(14)
O2 0.0447(17) 0.0241(17) 0.0361(17) -0.0103(13) -0.0097(15) 0.0002(14)
O3 0.0210(13) 0.0225(15) 0.0348(16) 0.0075(12) -0.0020(12) -0.0057(12)
N1 0.0187(15) 0.0109(16) 0.0247(17) -0.0001(13) -0.0015(13) -0.0017(13)
N2 0.032(2) 0.0261(19) 0.0304(19) -0.0006(15) -0.0100(17) -0.0025(17)
N3 0.0176(16) 0.0163(17) 0.0260(18) 0.0003(13) 0.0039(14) -0.0047(14)
C1 0.0186(19) 0.0104(18) 0.024(2) -0.0025(15) -0.0033(16) -0.0016(16)
C2 0.022(2) 0.020(2) 0.024(2) 0.0014(15) 0.0023(17) 0.0048(17)
C3 0.024(2) 0.012(2) 0.027(2) -0.0001(15) 0.0027(18) 0.0042(16)
C4 0.029(2) 0.014(2) 0.022(2) -0.0015(16) 0.0020(17) -0.0007(17)
C5 0.021(2) 0.031(2) 0.030(2) 0.0029(18) -0.0040(17) -0.0042(18)
C6 0.036(2) 0.027(2) 0.023(2) -0.0065(17) -0.0109(19) 0.000(2)
C7 0.032(2) 0.030(3) 0.022(2) -0.0047(17) -0.0042(18) 0.0098(19)
C8 0.029(2) 0.023(2) 0.028(2) 0.0077(16) -0.0032(19) 0.0043(19)
C9 0.030(2) 0.036(3) 0.026(2) 0.0034(19) -0.0025(19) 0.0120(19)
C10 0.0216(19) 0.014(2) 0.0118(18) -0.0008(14) 0.0037(15) 0.0020(15)
C11 0.0247(19) 0.015(2) 0.0204(19) 0.0014(15) -0.0007(16) -0.0017(16)
C12 0.0172(19) 0.033(2) 0.024(2) 0.0060(17) -0.0025(17) 0.0011(19)
C13 0.028(2) 0.026(2) 0.028(2) 0.0031(18) -0.0026(19) 0.0120(18)
C14 0.037(2) 0.018(2) 0.022(2) 0.0053(16) -0.002(2) 0.0087(19)
C15 0.023(2) 0.018(2) 0.018(2) 0.0019(16) -0.0019(17) -0.0024(16)
C16 0.022(2) 0.0088(18) 0.031(2) 0.0025(15) -0.0031(18) 0.0022(17)
C17 0.023(2) 0.022(2) 0.022(2) 0.0019(16) 0.0029(16) 0.0009(17)
C18 0.041(2) 0.024(2) 0.023(2) -0.0047(17) 0.0013(19) -0.0013(18)
C19 0.034(2) 0.028(3) 0.038(3) 0.0070(19) 0.010(2) 0.009(2)
C20 0.021(2) 0.026(2) 0.026(2) 0.0066(17) -0.0023(17) 0.0046(18)
_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 N2 1.232(4) . ?
O2 N2 1.242(4) . ?
O3 C16 1.236(4) . ?
N1 C10 1.375(4) . ?
N1 C1 1.467(4) . ?
N1 C4 1.470(4) . ?
N2 C11 1.460(5) . ?
N3 C16 1.339(4) . ?
N3 C17 1.469(5) . ?
N3 H3N 0.83(4) . ?
C1 C16 1.513(5) . ?
C1 C2 1.541(5) . ?
C1 H1 1.0000 . ?
C2 C3 1.547(5) . ?
C2 C5 1.548(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.529(5) . ?
C3 C8 1.548(5) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.512(5) . ?
C5 C9 1.540(5) . ?
C5 H5 1.0000 . ?
C6 C7 1.323(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.509(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.539(5) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.411(5) . ?
C10 C15 1.417(5) . ?
C11 C12 1.387(5) . ?
C12 C13 1.379(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C17 C18 1.521(5) . ?
C17 C19 1.524(5) . ?
C17 C20 1.535(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
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
C10 N1 C1 121.7(3) . . ?
C10 N1 C4 124.8(3) . . ?
C1 N1 C4 113.2(3) . . ?
O1 N2 O2 123.7(3) . . ?
O1 N2 C11 119.0(3) . . ?
O2 N2 C11 117.1(3) . . ?
C16 N3 C17 126.7(3) . . ?
C16 N3 H3N 117(3) . . ?
C17 N3 H3N 116(3) . . ?
N1 C1 C16 114.1(3) . . ?
N1 C1 C2 105.1(3) . . ?
C16 C1 C2 111.1(3) . . ?
N1 C1 H1 108.8 . . ?
C16 C1 H1 108.8 . . ?
C2 C1 H1 108.8 . . ?
C1 C2 C3 107.8(3) . . ?
C1 C2 C5 115.7(3) . . ?
C3 C2 C5 102.8(3) . . ?
C1 C2 H2 110.1 . . ?
C3 C2 H2 110.1 . . ?
C5 C2 H2 110.1 . . ?
C4 C3 C8 119.2(3) . . ?
C4 C3 C2 106.4(3) . . ?
C8 C3 C2 103.0(3) . . ?
C4 C3 H3 109.2 . . ?
C8 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
N1 C4 C3 106.2(3) . . ?
N1 C4 H4A 110.5 . . ?
C3 C4 H4A 110.5 . . ?
N1 C4 H4B 110.5 . . ?
C3 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
C6 C5 C9 99.7(3) . . ?
C6 C5 C2 107.3(3) . . ?
C9 C5 C2 100.0(3) . . ?
C6 C5 H5 115.8 . . ?
C9 C5 H5 115.8 . . ?
C2 C5 H5 115.8 . . ?
C7 C6 C5 107.7(4) . . ?
C7 C6 H6 126.1 . . ?
C5 C6 H6 126.1 . . ?
C6 C7 C8 107.6(3) . . ?
C6 C7 H7 126.2 . . ?
C8 C7 H7 126.2 . . ?
C7 C8 C9 99.8(3) . . ?
C7 C8 C3 108.2(3) . . ?
C9 C8 C3 99.5(3) . . ?
C7 C8 H8 115.7 . . ?
C9 C8 H8 115.7 . . ?
C3 C8 H8 115.7 . . ?
C5 C9 C8 93.3(3) . . ?
C5 C9 H9A 113.1 . . ?
C8 C9 H9A 113.1 . . ?
C5 C9 H9B 113.1 . . ?
C8 C9 H9B 113.1 . . ?
H9A C9 H9B 110.4 . . ?
N1 C10 C11 124.2(3) . . ?
N1 C10 C15 121.1(3) . . ?
C11 C10 C15 114.7(3) . . ?
C12 C11 C10 122.9(3) . . ?
C12 C11 N2 115.4(3) . . ?
C10 C11 N2 121.0(3) . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 118.9(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 121.4(4) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C10 121.7(3) . . ?
C14 C15 H15 119.2 . . ?
C10 C15 H15 119.2 . . ?
O3 C16 N3 124.4(3) . . ?
O3 C16 C1 119.5(3) . . ?
N3 C16 C1 116.1(3) . . ?
N3 C17 C18 106.7(3) . . ?
N3 C17 C19 109.4(3) . . ?
C18 C17 C19 109.7(3) . . ?
N3 C17 C20 109.2(3) . . ?
C18 C17 C20 110.8(3) . . ?
C19 C17 C20 110.9(3) . . ?
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 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C10 N1 C1 C16 -73.1(4) . . . . ?
C4 N1 C1 C16 113.1(3) . . . . ?
C10 N1 C1 C2 164.9(3) . . . . ?
C4 N1 C1 C2 -8.9(4) . . . . ?
N1 C1 C2 C3 2.2(4) . . . . ?
C16 C1 C2 C3 -121.6(3) . . . . ?
N1 C1 C2 C5 -112.1(3) . . . . ?
C16 C1 C2 C5 124.0(3) . . . . ?
C1 C2 C3 C4 4.6(4) . . . . ?
C5 C2 C3 C4 127.3(3) . . . . ?
C1 C2 C3 C8 -121.6(3) . . . . ?
C5 C2 C3 C8 1.1(3) . . . . ?
C10 N1 C4 C3 -161.7(3) . . . . ?
C1 N1 C4 C3 11.9(4) . . . . ?
C8 C3 C4 N1 106.1(4) . . . . ?
C2 C3 C4 N1 -9.6(4) . . . . ?
C1 C2 C5 C6 49.9(4) . . . . ?
C3 C2 C5 C6 -67.3(4) . . . . ?
C1 C2 C5 C9 153.5(3) . . . . ?
C3 C2 C5 C9 36.3(3) . . . . ?
C9 C5 C6 C7 -33.6(4) . . . . ?
C2 C5 C6 C7 70.1(4) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
C6 C7 C8 C9 34.3(4) . . . . ?
C6 C7 C8 C3 -69.1(4) . . . . ?
C4 C3 C8 C7 -51.9(4) . . . . ?
C2 C3 C8 C7 65.6(4) . . . . ?
C4 C3 C8 C9 -155.6(3) . . . . ?
C2 C3 C8 C9 -38.1(3) . . . . ?
C6 C5 C9 C8 50.7(3) . . . . ?
C2 C5 C9 C8 -58.9(3) . . . . ?
C7 C8 C9 C5 -51.1(3) . . . . ?
C3 C8 C9 C5 59.4(3) . . . . ?
C1 N1 C10 C11 166.8(3) . . . . ?
C4 N1 C10 C11 -20.1(5) . . . . ?
C1 N1 C10 C15 -15.5(5) . . . . ?
C4 N1 C10 C15 157.6(3) . . . . ?
N1 C10 C11 C12 168.2(3) . . . . ?
C15 C10 C11 C12 -9.6(5) . . . . ?
N1 C10 C11 N2 -21.3(5) . . . . ?
C15 C10 C11 N2 160.9(3) . . . . ?
O1 N2 C11 C12 -42.8(5) . . . . ?
O2 N2 C11 C12 131.5(4) . . . . ?
O1 N2 C11 C10 146.0(4) . . . . ?
O2 N2 C11 C10 -39.7(5) . . . . ?
C10 C11 C12 C13 5.6(6) . . . . ?
N2 C11 C12 C13 -165.4(3) . . . . ?
C11 C12 C13 C14 2.2(6) . . . . ?
C12 C13 C14 C15 -5.5(6) . . . . ?
C13 C14 C15 C10 1.0(6) . . . . ?
N1 C10 C15 C14 -171.6(3) . . . . ?
C11 C10 C15 C14 6.2(5) . . . . ?
C17 N3 C16 O3 6.6(6) . . . . ?
C17 N3 C16 C1 -170.8(3) . . . . ?
N1 C1 C16 O3 165.2(3) . . . . ?
C2 C1 C16 O3 -76.2(4) . . . . ?
N1 C1 C16 N3 -17.3(4) . . . . ?
C2 C1 C16 N3 101.3(3) . . . . ?
C16 N3 C17 C18 175.3(3) . . . . ?
C16 N3 C17 C19 56.7(5) . . . . ?
C16 N3 C17 C20 -64.9(4) . . . . ?
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 H3N N1 0.83(4) 2.31(4) 2.729(4) 112(3) .
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 25.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 0.216
_refine_diff_density_min -0.202
_refine_diff_density_rms 0.047