# Electronic Supplementary Material (ESI) for Organic and 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              ?
_publ_contact_author_name        'Jia Chen'
_publ_contact_author_email       chenjia07@lzu.cn
loop_
_publ_author_name
'Jia Chen'
'Jian-Jun Chen'
X.-J.Yao
'Kun Gao'

# Attachment 'web_deposit_cif_file_1_JiaChen_1287647726.cif'

data_web_deposit_cif_file_1_JiaChen_1287647726
_database_code_depnum_ccdc_archive 'CCDC 797511'
#TrackingRef 'web_deposit_cif_file_1_JiaChen_1287647726.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H28 N2 O6'
_chemical_formula_weight         392.44
#_chemical_absolute_configuration none

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   P2(1)2(1)2(1)

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                   11.3829(13)
_cell_length_b                   12.3833(15)
_cell_length_c                   13.4311(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1893.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2356
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      20.24

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9653
_exptl_absorpt_correction_T_max  0.9701
_exptl_absorpt_process_details   SADABS

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11744
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0568
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3496
_reflns_number_gt                2421
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0349P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(14)
_refine_ls_number_reflns         3496
_refine_ls_number_parameters     285
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.0898
_refine_ls_wR_factor_gt          0.0795
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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
C1 C 0.8463(2) 0.40616(18) 0.23743(17) 0.0298(6) Uani 1 1 d . . .
C2 C 0.9206(2) 0.35412(19) 0.15652(17) 0.0315(6) Uani 1 1 d . . .
C3 C 1.0334(2) 0.3736(2) 0.1238(2) 0.0404(7) Uani 1 1 d . . .
H3 H 1.0797 0.4261 0.1540 0.048 Uiso 1 1 calc R . .
C4 C 1.0762(3) 0.3133(2) 0.0450(2) 0.0493(8) Uani 1 1 d . . .
H4 H 1.1516 0.3262 0.0213 0.059 Uiso 1 1 calc R . .
C5 C 1.0087(3) 0.2349(2) 0.0016(2) 0.0505(8) Uani 1 1 d . . .
H5 H 1.0391 0.1958 -0.0516 0.061 Uiso 1 1 calc R . .
C6 C 0.8963(3) 0.2123(2) 0.03491(19) 0.0456(7) Uani 1 1 d . . .
H6 H 0.8512 0.1582 0.0057 0.055 Uiso 1 1 calc R . .
C7 C 0.8536(2) 0.2732(2) 0.11322(18) 0.0362(6) Uani 1 1 d . . .
C8 C 0.7607(2) 0.31079(19) 0.26229(18) 0.0334(6) Uani 1 1 d . . .
C9 C 0.6424(2) 0.3427(2) 0.3084(2) 0.0416(7) Uani 1 1 d . . .
H9A H 0.5868 0.2846 0.2972 0.050 Uiso 1 1 calc R . .
H9B H 0.6525 0.3502 0.3798 0.050 Uiso 1 1 calc R . .
C10 C 0.5906(2) 0.4468(2) 0.2676(2) 0.0419(7) Uani 1 1 d . . .
H10A H 0.5229 0.4673 0.3073 0.050 Uiso 1 1 calc R . .
H10B H 0.5643 0.4352 0.1998 0.050 Uiso 1 1 calc R . .
C11 C 0.6807(2) 0.5376(2) 0.26953(19) 0.0385(7) Uani 1 1 d . . .
C12 C 0.7751(2) 0.50107(19) 0.19485(18) 0.0318(6) Uani 1 1 d . . .
H12 H 0.7386 0.4805 0.1315 0.038 Uiso 1 1 calc R . .
C13 C 0.6283(3) 0.6444(2) 0.2336(2) 0.0527(8) Uani 1 1 d . . .
H13A H 0.5888 0.6330 0.1705 0.063 Uiso 1 1 calc R . .
H13B H 0.5703 0.6692 0.2813 0.063 Uiso 1 1 calc R . .
C14 C 0.7226(3) 0.7309(2) 0.2209(2) 0.0624(9) Uani 1 1 d . . .
H14A H 0.6869 0.7960 0.1945 0.075 Uiso 1 1 calc R . .
H14B H 0.7560 0.7481 0.2854 0.075 Uiso 1 1 calc R . .
C15 C 0.8192(3) 0.6941(2) 0.1517(2) 0.0547(8) Uani 1 1 d . . .
H15A H 0.7888 0.6918 0.0843 0.066 Uiso 1 1 calc R . .
H15B H 0.8824 0.7466 0.1534 0.066 Uiso 1 1 calc R . .
C16 C 0.9484(2) 0.57654(19) 0.26672(19) 0.0401(7) Uani 1 1 d . . .
H16A H 0.9359 0.6365 0.3120 0.048 Uiso 1 1 calc R . .
H16B H 1.0299 0.5767 0.2456 0.048 Uiso 1 1 calc R . .
C17 C 0.9169(2) 0.46759(19) 0.31819(17) 0.0339(6) Uani 1 1 d . . .
H17 H 0.9873 0.4277 0.3385 0.041 Uiso 1 1 calc R . .
C18 C 0.8397(2) 0.4936(2) 0.40492(19) 0.0382(7) Uani 1 1 d . . .
C19 C 0.7273(2) 0.5512(2) 0.3784(2) 0.0428(7) Uani 1 1 d . . .
H19A H 0.7387 0.6277 0.3907 0.051 Uiso 1 1 calc R . .
H19B H 0.6665 0.5265 0.4236 0.051 Uiso 1 1 calc R . .
C20 C 0.8138(2) 0.2234(2) 0.3302(2) 0.0401(7) Uani 1 1 d . . .
H1 H 0.708(2) 0.201(2) 0.1656(17) 0.036(7) Uiso 1 1 d . . .
H1N H 0.9113(19) 0.5675(17) 0.1165(17) 0.027(6) Uiso 1 1 d . . .
H1W H 0.053(3) 0.645(2) 0.040(2) 0.086(12) Uiso 1 1 d D . .
H2W H 0.055(3) 0.554(3) -0.028(3) 0.15(2) Uiso 1 1 d D . .
H3W H 0.311(4) 0.558(4) 0.061(3) 0.16(2) Uiso 1 1 d D . .
H4W H 0.426(3) 0.589(5) 0.023(4) 0.25(4) Uiso 1 1 d D . .
N1 N 0.74315(19) 0.26695(19) 0.16036(16) 0.0400(6) Uani 1 1 d . . .
N2 N 0.8677(2) 0.58517(16) 0.17804(17) 0.0389(5) Uani 1 1 d . . .
O1 O 0.77620(18) 0.12868(16) 0.31845(15) 0.0548(5) Uani 1 1 d . . .
O2 O 0.88530(19) 0.25230(15) 0.39434(15) 0.0621(6) Uani 1 1 d . . .
O3 O 0.86898(17) 0.47776(15) 0.49022(13) 0.0540(5) Uani 1 1 d . . .
O4 O 0.3566(4) 0.5659(3) 0.0087(2) 0.1123(10) Uani 1 1 d D . .
O5 O 0.00816(19) 0.5927(2) 0.00941(17) 0.0555(6) Uani 1 1 d D . .
O6 O 0.7015(2) 0.0086(2) 0.1399(2) 0.0844(8) Uani 1 1 d D . .
H5W H 0.746(8) -0.017(15) 0.094(5) 1.00(15) Uiso 1 1 d D . .
H6W H 0.735(4) 0.019(4) 0.197(3) 0.15(2) Uiso 1 1 d 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
C1 0.0316(15) 0.0314(14) 0.0263(13) -0.0029(11) 0.0021(12) 0.0018(12)
C2 0.0363(15) 0.0315(14) 0.0266(14) 0.0021(11) -0.0012(12) 0.0040(12)
C3 0.0380(17) 0.0418(16) 0.0412(16) 0.0038(14) 0.0074(13) 0.0023(13)
C4 0.0457(18) 0.0595(19) 0.0425(17) 0.0043(16) 0.0144(15) 0.0068(17)
C5 0.061(2) 0.055(2) 0.0357(16) -0.0026(14) 0.0077(16) 0.0152(17)
C6 0.0548(19) 0.0463(18) 0.0356(16) -0.0059(13) -0.0031(14) 0.0081(15)
C7 0.0393(16) 0.0379(15) 0.0314(15) 0.0028(13) -0.0009(13) 0.0084(14)
C8 0.0335(15) 0.0346(14) 0.0322(15) -0.0012(12) 0.0016(12) -0.0034(12)
C9 0.0357(15) 0.0445(16) 0.0448(16) -0.0060(13) 0.0064(14) 0.0007(14)
C10 0.0329(15) 0.0481(17) 0.0447(17) -0.0076(13) 0.0030(13) 0.0036(13)
C11 0.0373(15) 0.0435(16) 0.0347(15) -0.0033(13) -0.0012(13) 0.0072(13)
C12 0.0338(15) 0.0331(14) 0.0285(13) -0.0060(11) -0.0031(12) 0.0013(12)
C13 0.0539(19) 0.0489(18) 0.0554(19) -0.0033(15) -0.0074(16) 0.0166(16)
C14 0.081(2) 0.0384(18) 0.068(2) 0.0048(16) -0.0070(19) 0.0179(18)
C15 0.072(2) 0.0333(17) 0.059(2) 0.0077(15) -0.0031(17) 0.0045(15)
C16 0.0431(17) 0.0387(15) 0.0386(16) -0.0032(13) -0.0046(14) -0.0050(12)
C17 0.0354(14) 0.0383(15) 0.0281(13) -0.0012(12) -0.0025(12) 0.0031(12)
C18 0.0480(18) 0.0371(16) 0.0296(16) -0.0035(12) -0.0001(14) -0.0009(14)
C19 0.0442(18) 0.0452(17) 0.0389(16) -0.0082(14) 0.0058(14) 0.0018(14)
C20 0.0400(16) 0.0413(18) 0.0392(17) 0.0010(14) 0.0066(14) 0.0002(14)
N1 0.0438(15) 0.0378(14) 0.0383(14) -0.0060(11) -0.0026(11) -0.0051(12)
N2 0.0460(14) 0.0376(12) 0.0330(12) 0.0036(10) -0.0001(12) -0.0003(11)
O1 0.0653(14) 0.0406(12) 0.0585(13) 0.0078(10) 0.0014(11) -0.0074(10)
O2 0.0837(16) 0.0464(12) 0.0562(13) 0.0118(10) -0.0272(13) -0.0023(12)
O3 0.0700(14) 0.0660(14) 0.0261(11) -0.0001(9) -0.0006(10) 0.0095(11)
O4 0.100(2) 0.148(3) 0.089(2) -0.053(2) 0.002(2) 0.016(2)
O5 0.0626(14) 0.0569(14) 0.0470(13) -0.0019(11) -0.0056(12) -0.0100(13)
O6 0.0803(19) 0.0752(18) 0.098(2) -0.0020(16) -0.0041(17) -0.0141(14)

_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
C1 C2 1.520(3) . ?
C1 C12 1.538(3) . ?
C1 C17 1.550(3) . ?
C1 C8 1.567(3) . ?
C2 C3 1.379(3) . ?
C2 C7 1.387(3) . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(4) . ?
C6 H6 0.9300 . ?
C7 N1 1.410(3) . ?
C8 N1 1.486(3) . ?
C8 C9 1.534(3) . ?
C8 C20 1.539(4) . ?
C9 C10 1.520(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.523(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C13 1.529(4) . ?
C11 C12 1.537(3) . ?
C11 C19 1.565(4) . ?
C12 N2 1.499(3) . ?
C12 H12 0.9800 . ?
C13 C14 1.526(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.510(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N2 1.500(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N2 1.508(3) . ?
C16 C17 1.558(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.495(3) . ?
C17 H17 0.9800 . ?
C18 O3 1.209(3) . ?
C18 C19 1.507(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 O2 1.238(3) . ?
C20 O1 1.258(3) . ?
N1 H1 0.91(3) . ?
N2 H1N 0.99(2) . ?
O4 H3W 0.88(2) . ?
O4 H4W 0.87(3) . ?
O5 H1W 0.92(2) . ?
O5 H2W 0.88(2) . ?
O6 H5W 0.86(3) . ?
O6 H6W 0.87(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C12 110.57(19) . . ?
C2 C1 C17 114.8(2) . . ?
C12 C1 C17 99.13(18) . . ?
C2 C1 C8 100.29(18) . . ?
C12 C1 C8 109.1(2) . . ?
C17 C1 C8 122.9(2) . . ?
C3 C2 C7 120.3(2) . . ?
C3 C2 C1 132.2(2) . . ?
C7 C2 C1 107.5(2) . . ?
C2 C3 C4 118.5(3) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 117.4(3) . . ?
C7 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
C6 C7 C2 121.4(2) . . ?
C6 C7 N1 128.7(3) . . ?
C2 C7 N1 110.0(2) . . ?
N1 C8 C9 110.34(19) . . ?
N1 C8 C20 110.0(2) . . ?
C9 C8 C20 106.6(2) . . ?
N1 C8 C1 99.36(19) . . ?
C9 C8 C1 116.0(2) . . ?
C20 C8 C1 114.4(2) . . ?
C10 C9 C8 114.5(2) . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C8 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C11 111.0(2) . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C13 111.7(2) . . ?
C10 C11 C12 104.0(2) . . ?
C13 C11 C12 108.8(2) . . ?
C10 C11 C19 108.9(2) . . ?
C13 C11 C19 109.5(2) . . ?
C12 C11 C19 113.9(2) . . ?
N2 C12 C11 112.6(2) . . ?
N2 C12 C1 102.48(18) . . ?
C11 C12 C1 110.52(19) . . ?
N2 C12 H12 110.3 . . ?
C11 C12 H12 110.3 . . ?
C1 C12 H12 110.3 . . ?
C14 C13 C11 111.6(2) . . ?
C14 C13 H13A 109.3 . . ?
C11 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C11 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C13 111.7(2) . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
N2 C15 C14 113.3(2) . . ?
N2 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
N2 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
N2 C16 C17 105.78(18) . . ?
N2 C16 H16A 110.6 . . ?
C17 C16 H16A 110.6 . . ?
N2 C16 H16B 110.6 . . ?
C17 C16 H16B 110.6 . . ?
H16A C16 H16B 108.7 . . ?
C18 C17 C1 110.2(2) . . ?
C18 C17 C16 107.1(2) . . ?
C1 C17 C16 103.52(18) . . ?
C18 C17 H17 111.9 . . ?
C1 C17 H17 111.9 . . ?
C16 C17 H17 111.9 . . ?
O3 C18 C17 122.7(2) . . ?
O3 C18 C19 122.3(2) . . ?
C17 C18 C19 114.7(2) . . ?
C18 C19 C11 117.2(2) . . ?
C18 C19 H19A 108.0 . . ?
C11 C19 H19A 108.0 . . ?
C18 C19 H19B 108.0 . . ?
C11 C19 H19B 108.0 . . ?
H19A C19 H19B 107.2 . . ?
O2 C20 O1 125.5(3) . . ?
O2 C20 C8 117.8(2) . . ?
O1 C20 C8 116.6(2) . . ?
C7 N1 C8 105.9(2) . . ?
C7 N1 H1 118.6(15) . . ?
C8 N1 H1 108.4(15) . . ?
C12 N2 C15 113.7(2) . . ?
C12 N2 C16 105.09(18) . . ?
C15 N2 C16 118.3(2) . . ?
C12 N2 H1N 109.0(12) . . ?
C15 N2 H1N 100.8(12) . . ?
C16 N2 H1N 109.8(13) . . ?
H3W O4 H4W 113(3) . . ?
H1W O5 H2W 108(2) . . ?
H5W O6 H6W 115(4) . . ?

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
C12 C1 C2 C3 90.2(3) . . . . ?
C17 C1 C2 C3 -20.9(4) . . . . ?
C8 C1 C2 C3 -154.7(3) . . . . ?
C12 C1 C2 C7 -90.0(2) . . . . ?
C17 C1 C2 C7 158.84(19) . . . . ?
C8 C1 C2 C7 25.0(2) . . . . ?
C7 C2 C3 C4 2.2(4) . . . . ?
C1 C2 C3 C4 -178.1(2) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 C7 0.9(4) . . . . ?
C5 C6 C7 C2 0.2(4) . . . . ?
C5 C6 C7 N1 179.7(2) . . . . ?
C3 C2 C7 C6 -1.8(4) . . . . ?
C1 C2 C7 C6 178.4(2) . . . . ?
C3 C2 C7 N1 178.6(2) . . . . ?
C1 C2 C7 N1 -1.1(3) . . . . ?
C2 C1 C8 N1 -37.8(2) . . . . ?
C12 C1 C8 N1 78.4(2) . . . . ?
C17 C1 C8 N1 -166.5(2) . . . . ?
C2 C1 C8 C9 -155.9(2) . . . . ?
C12 C1 C8 C9 -39.8(3) . . . . ?
C17 C1 C8 C9 75.3(3) . . . . ?
C2 C1 C8 C20 79.3(2) . . . . ?
C12 C1 C8 C20 -164.5(2) . . . . ?
C17 C1 C8 C20 -49.4(3) . . . . ?
N1 C8 C9 C10 -75.2(3) . . . . ?
C20 C8 C9 C10 165.4(2) . . . . ?
C1 C8 C9 C10 36.7(3) . . . . ?
C8 C9 C10 C11 -50.2(3) . . . . ?
C9 C10 C11 C13 -177.2(2) . . . . ?
C9 C10 C11 C12 65.7(3) . . . . ?
C9 C10 C11 C19 -56.1(3) . . . . ?
C10 C11 C12 N2 174.5(2) . . . . ?
C13 C11 C12 N2 55.3(3) . . . . ?
C19 C11 C12 N2 -67.1(3) . . . . ?
C10 C11 C12 C1 -71.5(2) . . . . ?
C13 C11 C12 C1 169.3(2) . . . . ?
C19 C11 C12 C1 46.8(3) . . . . ?
C2 C1 C12 N2 -72.1(2) . . . . ?
C17 C1 C12 N2 48.8(2) . . . . ?
C8 C1 C12 N2 178.47(18) . . . . ?
C2 C1 C12 C11 167.62(19) . . . . ?
C17 C1 C12 C11 -71.4(2) . . . . ?
C8 C1 C12 C11 58.2(2) . . . . ?
C10 C11 C13 C14 -171.6(2) . . . . ?
C12 C11 C13 C14 -57.3(3) . . . . ?
C19 C11 C13 C14 67.7(3) . . . . ?
C11 C13 C14 C15 55.7(3) . . . . ?
C13 C14 C15 N2 -50.4(3) . . . . ?
C2 C1 C17 C18 -167.2(2) . . . . ?
C12 C1 C17 C18 75.0(2) . . . . ?
C8 C1 C17 C18 -45.0(3) . . . . ?
C2 C1 C17 C16 78.5(2) . . . . ?
C12 C1 C17 C16 -39.3(2) . . . . ?
C8 C1 C17 C16 -159.3(2) . . . . ?
N2 C16 C17 C18 -100.1(2) . . . . ?
N2 C16 C17 C1 16.4(2) . . . . ?
C1 C17 C18 O3 133.1(3) . . . . ?
C16 C17 C18 O3 -114.9(3) . . . . ?
C1 C17 C18 C19 -52.6(3) . . . . ?
C16 C17 C18 C19 59.4(3) . . . . ?
O3 C18 C19 C11 -162.6(3) . . . . ?
C17 C18 C19 C11 23.1(3) . . . . ?
C10 C11 C19 C18 95.4(3) . . . . ?
C13 C11 C19 C18 -142.2(2) . . . . ?
C12 C11 C19 C18 -20.2(3) . . . . ?
N1 C8 C20 O2 144.4(2) . . . . ?
C9 C8 C20 O2 -96.0(3) . . . . ?
C1 C8 C20 O2 33.6(3) . . . . ?
N1 C8 C20 O1 -38.8(3) . . . . ?
C9 C8 C20 O1 80.8(3) . . . . ?
C1 C8 C20 O1 -149.6(2) . . . . ?
C6 C7 N1 C8 155.2(3) . . . . ?
C2 C7 N1 C8 -25.2(3) . . . . ?
C9 C8 N1 C7 161.4(2) . . . . ?
C20 C8 N1 C7 -81.2(2) . . . . ?
C1 C8 N1 C7 39.1(2) . . . . ?
C11 C12 N2 C15 -51.8(3) . . . . ?
C1 C12 N2 C15 -170.6(2) . . . . ?
C11 C12 N2 C16 79.1(2) . . . . ?
C1 C12 N2 C16 -39.7(2) . . . . ?
C14 C15 N2 C12 48.9(3) . . . . ?
C14 C15 N2 C16 -75.1(3) . . . . ?
C17 C16 N2 C12 14.1(2) . . . . ?
C17 C16 N2 C15 142.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.037