# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2008
data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Georges Dewynter'
_publ_contact_author_email       DEWYNTER@UNIV-MONTP2.FR

_publ_section_title              
;
Transannular rearrangement of activated
2,5-diketopiperazines: a key access to original scaffolds
;
loop_
_publ_author_name
'Georges Dewynter'
'Daniel Farran'
'Jean Martinez'
'Isabelle Parrot'
'Loic Toupet'

# Attachment 'df405revu.cif'

data_df405revu
_database_code_depnum_ccdc_archive 'CCDC 643845'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 N2 O4'
_chemical_formula_weight         404.45

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

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

_cell_length_a                   10.4911(5)
_cell_length_b                   12.2289(6)
_cell_length_c                   16.1319(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2069.64(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.089
_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      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Saphire 3 Xcalibur'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 19.64
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15200
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         26.99
_reflns_number_total             4503
_reflns_number_gt                3815
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlis CCD, Oxford Diffraction Ltd.,Version 1.171.26'
_computing_cell_refinement       
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.26'
_computing_data_reduction        
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.26'

_computing_structure_solution    'SIR-97_(Altomare & al., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON_(Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0722P)^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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0105(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_number_reflns         4503
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0728
_refine_ls_wR_factor_gt          0.0697
_refine_ls_goodness_of_fit_ref   0.724
_refine_ls_restrained_S_all      0.724
_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 0.11180(8) -0.55050(8) 0.69276(6) 0.0225(2) Uani 1 1 d . . .
O2 O -0.06876(9) -0.39950(7) 0.93163(5) 0.0211(2) Uani 1 1 d . . .
O3 O 0.25936(8) -0.24598(7) 0.71522(6) 0.0200(2) Uani 1 1 d . . .
O4 O 0.15250(8) -0.59165(7) 0.88262(6) 0.0215(2) Uani 1 1 d . . .
N1 N 0.14769(9) -0.38952(8) 0.76706(6) 0.0169(2) Uani 1 1 d . . .
N2 N -0.04938(10) -0.60221(9) 0.83793(6) 0.0180(2) Uani 1 1 d . . .
H2 H -0.1194 -0.6383 0.8335 0.022 Uiso 1 1 calc R . .
C1 C 0.08431(12) -0.48736(10) 0.74721(8) 0.0172(3) Uani 1 1 d . . .
C2 C -0.03484(12) -0.49508(9) 0.80163(7) 0.0165(3) Uani 1 1 d . . .
C3 C -0.01379(11) -0.40523(10) 0.86637(7) 0.0158(2) Uani 1 1 d . . .
C4 C 0.08293(12) -0.32358(10) 0.83229(8) 0.0167(3) Uani 1 1 d . . .
H4 H 0.0365 -0.2638 0.8054 0.020 Uiso 1 1 calc R . .
C5 C 0.17521(13) -0.27439(10) 0.89607(8) 0.0203(3) Uani 1 1 d . . .
H5 H 0.2364 -0.2295 0.8653 0.024 Uiso 1 1 calc R . .
C6 C 0.25180(13) -0.35952(12) 0.94394(9) 0.0280(3) Uani 1 1 d . . .
H6A H 0.2963 -0.4059 0.9056 0.042 Uiso 1 1 calc R . .
H6B H 0.1951 -0.4030 0.9771 0.042 Uiso 1 1 calc R . .
H6C H 0.3122 -0.3233 0.9793 0.042 Uiso 1 1 calc R . .
C7 C 0.10408(14) -0.19780(11) 0.95550(9) 0.0259(3) Uani 1 1 d . . .
H7A H 0.0570 -0.1447 0.9241 0.039 Uiso 1 1 calc R . .
H7B H 0.1644 -0.1611 0.9906 0.039 Uiso 1 1 calc R . .
H7C H 0.0463 -0.2397 0.9890 0.039 Uiso 1 1 calc R . .
C8 C -0.15131(12) -0.46444(11) 0.74722(8) 0.0191(3) Uani 1 1 d . . .
H8A H -0.1328 -0.3966 0.7185 0.023 Uiso 1 1 calc R . .
H8B H -0.1631 -0.5208 0.7056 0.023 Uiso 1 1 calc R . .
C9 C -0.27337(12) -0.45104(12) 0.79432(8) 0.0231(3) Uani 1 1 d . . .
H9 H -0.3107 -0.5130 0.8173 0.028 Uiso 1 1 calc R . .
C10 C -0.33036(15) -0.35689(14) 0.80493(11) 0.0362(4) Uani 1 1 d . . .
H10A H -0.2951 -0.2936 0.7826 0.043 Uiso 1 1 calc R . .
H10B H -0.4061 -0.3533 0.8348 0.043 Uiso 1 1 calc R . .
C11 C 0.25071(11) -0.34525(10) 0.72272(8) 0.0166(3) Uani 1 1 d . . .
C12 C 0.34938(11) -0.42096(10) 0.69036(8) 0.0176(3) Uani 1 1 d . . .
C13 C 0.41771(12) -0.38806(11) 0.62097(8) 0.0212(3) Uani 1 1 d . . .
H13 H 0.4000 -0.3212 0.5960 0.025 Uiso 1 1 calc R . .
C14 C 0.51249(12) -0.45510(12) 0.58898(8) 0.0244(3) Uani 1 1 d . . .
H14 H 0.5566 -0.4345 0.5415 0.029 Uiso 1 1 calc R . .
C15 C 0.54093(13) -0.55261(12) 0.62819(9) 0.0262(3) Uani 1 1 d . . .
H15 H 0.6040 -0.5977 0.6065 0.031 Uiso 1 1 calc R . .
C16 C 0.47681(12) -0.58402(10) 0.69923(9) 0.0237(3) Uani 1 1 d . . .
H16 H 0.4990 -0.6486 0.7261 0.028 Uiso 1 1 calc R . .
C17 C 0.37922(12) -0.51902(10) 0.73039(8) 0.0195(3) Uani 1 1 d . . .
H17 H 0.3343 -0.5405 0.7773 0.023 Uiso 1 1 calc R . .
C18 C 0.05230(11) -0.64355(10) 0.87931(7) 0.0166(2) Uani 1 1 d . . .
C19 C 0.03728(13) -0.75051(9) 0.92276(7) 0.0164(2) Uani 1 1 d . . .
C20 C -0.08051(12) -0.78752(10) 0.95015(8) 0.0191(3) Uani 1 1 d . . .
H20 H -0.1541 -0.7491 0.9365 0.023 Uiso 1 1 calc R . .
C21 C -0.08874(12) -0.88203(11) 0.99804(9) 0.0223(3) Uani 1 1 d . . .
H21 H -0.1677 -0.9068 1.0163 0.027 Uiso 1 1 calc R . .
C22 C 0.02089(13) -0.93888(11) 1.01827(8) 0.0228(3) Uani 1 1 d . . .
H22 H 0.0155 -1.0013 1.0510 0.027 Uiso 1 1 calc R . .
C23 C 0.13909(12) -0.90339(11) 0.99012(8) 0.0206(3) Uani 1 1 d . . .
H23 H 0.2123 -0.9427 1.0031 0.025 Uiso 1 1 calc R . .
C24 C 0.14764(12) -0.80913(10) 0.94255(7) 0.0177(3) Uani 1 1 d . . .
H24 H 0.2266 -0.7850 0.9238 0.021 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
O1 0.0241(5) 0.0212(5) 0.0222(5) -0.0061(4) 0.0015(4) -0.0021(4)
O2 0.0211(4) 0.0245(5) 0.0176(4) 0.0015(4) 0.0006(4) -0.0017(4)
O3 0.0188(4) 0.0156(5) 0.0256(5) 0.0039(3) 0.0020(4) 0.0011(4)
O4 0.0176(4) 0.0201(4) 0.0267(5) 0.0047(4) -0.0038(4) -0.0054(4)
N1 0.0165(5) 0.0141(5) 0.0199(5) -0.0007(4) 0.0023(4) -0.0008(4)
N2 0.0153(5) 0.0158(5) 0.0230(5) 0.0030(4) -0.0016(4) -0.0034(4)
C1 0.0173(6) 0.0151(6) 0.0191(6) 0.0031(5) -0.0026(5) -0.0017(5)
C2 0.0160(6) 0.0155(6) 0.0180(6) 0.0018(5) -0.0024(5) -0.0012(5)
C3 0.0138(6) 0.0157(6) 0.0177(6) 0.0021(5) -0.0032(4) 0.0011(5)
C4 0.0167(6) 0.0155(6) 0.0179(6) -0.0005(5) 0.0014(5) 0.0012(5)
C5 0.0193(6) 0.0175(6) 0.0242(7) -0.0027(5) -0.0002(5) -0.0036(5)
C6 0.0238(7) 0.0272(7) 0.0331(8) -0.0077(6) -0.0112(6) 0.0029(6)
C7 0.0297(7) 0.0210(7) 0.0272(7) -0.0055(6) -0.0016(6) 0.0004(6)
C8 0.0185(6) 0.0197(6) 0.0190(6) 0.0016(5) -0.0042(5) -0.0020(5)
C9 0.0180(6) 0.0273(7) 0.0240(7) 0.0041(6) -0.0060(5) -0.0017(5)
C10 0.0284(8) 0.0373(9) 0.0430(9) 0.0030(7) 0.0006(7) 0.0058(7)
C11 0.0150(6) 0.0183(6) 0.0166(6) 0.0028(5) -0.0015(5) 0.0000(5)
C12 0.0147(6) 0.0172(6) 0.0208(6) -0.0015(5) -0.0015(5) 0.0002(5)
C13 0.0188(6) 0.0225(7) 0.0222(6) 0.0024(5) -0.0011(5) 0.0017(5)
C14 0.0209(7) 0.0309(7) 0.0213(7) 0.0000(6) 0.0026(5) 0.0032(6)
C15 0.0213(7) 0.0276(7) 0.0298(7) -0.0073(6) -0.0020(6) 0.0067(6)
C16 0.0213(6) 0.0167(6) 0.0330(7) -0.0017(5) -0.0061(6) 0.0045(5)
C17 0.0184(6) 0.0168(6) 0.0234(6) 0.0013(5) -0.0019(5) -0.0008(5)
C18 0.0178(6) 0.0156(6) 0.0165(6) -0.0002(5) 0.0003(5) 0.0002(5)
C19 0.0204(6) 0.0148(6) 0.0141(6) -0.0019(5) 0.0004(5) -0.0018(5)
C20 0.0181(6) 0.0185(6) 0.0209(7) -0.0004(5) 0.0006(5) 0.0012(5)
C21 0.0199(6) 0.0201(7) 0.0269(7) 0.0018(5) 0.0051(5) -0.0027(5)
C22 0.0280(7) 0.0155(6) 0.0248(7) 0.0031(5) 0.0031(6) -0.0010(5)
C23 0.0195(6) 0.0177(6) 0.0247(7) -0.0012(5) -0.0019(5) 0.0023(5)
C24 0.0159(6) 0.0180(6) 0.0192(6) -0.0030(5) 0.0000(5) -0.0012(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
O1 C1 1.2045(16) . ?
O2 C3 1.2024(15) . ?
O3 C11 1.2234(15) . ?
O4 C18 1.2291(15) . ?
N1 C11 1.4046(16) . ?
N1 C1 1.4057(16) . ?
N1 C4 1.4897(16) . ?
N2 C18 1.3561(16) . ?
N2 C2 1.4431(15) . ?
N2 H2 0.8600 . ?
C1 C2 1.5305(18) . ?
C2 C3 1.5319(16) . ?
C2 C8 1.5504(17) . ?
C3 C4 1.5261(17) . ?
C4 C5 1.5356(18) . ?
C4 H4 0.9800 . ?
C5 C6 1.5251(19) . ?
C5 C7 1.5339(19) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.4979(18) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.309(2) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C11 C12 1.4837(17) . ?
C12 C17 1.3976(18) . ?
C12 C13 1.3888(18) . ?
C13 C14 1.3882(18) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.3902(18) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.4922(17) . ?
C19 C20 1.3883(18) . ?
C19 C24 1.3987(18) . ?
C20 C21 1.3928(19) . ?
C20 H20 0.9300 . ?
C21 C22 1.3830(19) . ?
C21 H21 0.9300 . ?
C22 C23 1.3901(18) . ?
C22 H22 0.9300 . ?
C23 C24 1.3877(19) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

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
C11 N1 C1 125.16(11) . . ?
C11 N1 C4 120.14(10) . . ?
C1 N1 C4 113.95(10) . . ?
C18 N2 C2 117.07(10) . . ?
C18 N2 H2 121.5 . . ?
C2 N2 H2 121.5 . . ?
O1 C1 N1 126.77(12) . . ?
O1 C1 C2 125.05(11) . . ?
N1 C1 C2 107.94(10) . . ?
N2 C2 C3 112.94(10) . . ?
N2 C2 C1 112.03(10) . . ?
C3 C2 C1 103.25(10) . . ?
N2 C2 C8 111.45(10) . . ?
C3 C2 C8 109.04(10) . . ?
C1 C2 C8 107.70(9) . . ?
O2 C3 C4 126.60(11) . . ?
O2 C3 C2 124.72(11) . . ?
C4 C3 C2 108.63(10) . . ?
N1 C4 C3 101.75(10) . . ?
N1 C4 C5 113.45(10) . . ?
C3 C4 C5 115.73(10) . . ?
N1 C4 H4 108.5 . . ?
C3 C4 H4 108.5 . . ?
C5 C4 H4 108.5 . . ?
C6 C5 C7 110.90(11) . . ?
C6 C5 C4 113.83(11) . . ?
C7 C5 C4 110.56(11) . . ?
C6 C5 H5 107.1 . . ?
C7 C5 H5 107.1 . . ?
C4 C5 H5 107.1 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C2 114.40(10) . . ?
C9 C8 H8A 108.7 . . ?
C2 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C2 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 123.59(14) . . ?
C10 C9 H9 118.2 . . ?
C8 C9 H9 118.2 . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
O3 C11 N1 119.33(11) . . ?
O3 C11 C12 122.19(11) . . ?
N1 C11 C12 118.40(10) . . ?
C17 C12 C13 120.36(12) . . ?
C17 C12 C11 121.95(11) . . ?
C13 C12 C11 117.57(11) . . ?
C14 C13 C12 119.88(12) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 119.60(13) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.91(12) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 119.93(12) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 119.24(12) . . ?
C12 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
O4 C18 N2 120.11(11) . . ?
O4 C18 C19 121.50(11) . . ?
N2 C18 C19 118.35(11) . . ?
C20 C19 C24 119.81(11) . . ?
C20 C19 C18 121.96(11) . . ?
C24 C19 C18 117.97(11) . . ?
C19 C20 C21 120.15(12) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 119.77(12) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.52(12) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 119.85(12) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C19 C24 C23 119.90(11) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?

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
C11 N1 C1 O1 4.1(2) . . . . ?
C4 N1 C1 O1 174.16(12) . . . . ?
C11 N1 C1 C2 -170.45(11) . . . . ?
C4 N1 C1 C2 -0.41(13) . . . . ?
C18 N2 C2 C3 -64.04(14) . . . . ?
C18 N2 C2 C1 52.04(14) . . . . ?
C18 N2 C2 C8 172.80(10) . . . . ?
O1 C1 C2 N2 51.13(16) . . . . ?
N1 C1 C2 N2 -134.18(10) . . . . ?
O1 C1 C2 C3 172.94(12) . . . . ?
N1 C1 C2 C3 -12.37(12) . . . . ?
O1 C1 C2 C8 -71.78(15) . . . . ?
N1 C1 C2 C8 102.91(11) . . . . ?
N2 C2 C3 O2 -40.57(17) . . . . ?
C1 C2 C3 O2 -161.76(11) . . . . ?
C8 C2 C3 O2 83.92(14) . . . . ?
N2 C2 C3 C4 141.81(11) . . . . ?
C1 C2 C3 C4 20.61(12) . . . . ?
C8 C2 C3 C4 -93.70(11) . . . . ?
C11 N1 C4 C3 -176.43(10) . . . . ?
C1 N1 C4 C3 12.98(13) . . . . ?
C11 N1 C4 C5 -51.44(14) . . . . ?
C1 N1 C4 C5 137.97(11) . . . . ?
O2 C3 C4 N1 161.96(12) . . . . ?
C2 C3 C4 N1 -20.48(12) . . . . ?
O2 C3 C4 C5 38.50(18) . . . . ?
C2 C3 C4 C5 -143.93(10) . . . . ?
N1 C4 C5 C6 -60.53(14) . . . . ?
C3 C4 C5 C6 56.56(15) . . . . ?
N1 C4 C5 C7 173.87(10) . . . . ?
C3 C4 C5 C7 -69.04(14) . . . . ?
N2 C2 C8 C9 65.77(14) . . . . ?
C3 C2 C8 C9 -59.59(14) . . . . ?
C1 C2 C8 C9 -170.97(11) . . . . ?
C2 C8 C9 C10 110.85(16) . . . . ?
C1 N1 C11 O3 143.78(12) . . . . ?
C4 N1 C11 O3 -25.69(17) . . . . ?
C1 N1 C11 C12 -39.47(17) . . . . ?
C4 N1 C11 C12 151.06(11) . . . . ?
O3 C11 C12 C17 146.48(13) . . . . ?
N1 C11 C12 C17 -30.17(17) . . . . ?
O3 C11 C12 C13 -29.63(18) . . . . ?
N1 C11 C12 C13 153.72(11) . . . . ?
C17 C12 C13 C14 2.81(19) . . . . ?
C11 C12 C13 C14 178.99(12) . . . . ?
C12 C13 C14 C15 -2.1(2) . . . . ?
C13 C14 C15 C16 -0.4(2) . . . . ?
C14 C15 C16 C17 2.3(2) . . . . ?
C13 C12 C17 C16 -0.95(18) . . . . ?
C11 C12 C17 C16 -176.96(11) . . . . ?
C15 C16 C17 C12 -1.60(19) . . . . ?
C2 N2 C18 O4 -2.12(17) . . . . ?
C2 N2 C18 C19 175.62(10) . . . . ?
O4 C18 C19 C20 152.10(12) . . . . ?
N2 C18 C19 C20 -25.61(17) . . . . ?
O4 C18 C19 C24 -21.99(17) . . . . ?
N2 C18 C19 C24 160.30(11) . . . . ?
C24 C19 C20 C21 0.78(18) . . . . ?
C18 C19 C20 C21 -173.20(12) . . . . ?
C19 C20 C21 C22 0.0(2) . . . . ?
C20 C21 C22 C23 -1.0(2) . . . . ?
C21 C22 C23 C24 1.1(2) . . . . ?
C20 C19 C24 C23 -0.64(18) . . . . ?
C18 C19 C24 C23 173.58(11) . . . . ?
C22 C23 C24 C19 -0.31(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.036