# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013


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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
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#  except for the purpose of generating routine backup copies 
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#  data retrieval see:
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data_l-4a
_database_code_depnum_ccdc_archive 'CCDC 867497'
#TrackingRef 'l-4a.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 N7 O10'
_chemical_formula_weight         517.42

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

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

_cell_length_a                   7.1843(7)
_cell_length_b                   11.8503(12)
_cell_length_c                   13.9092(14)
_cell_angle_alpha                114.553(3)
_cell_angle_beta                 95.7160(10)
_cell_angle_gamma                91.176(2)
_cell_volume                     1069.23(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1800
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      26.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.132
_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      150(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 II CCD AREA DETECTOR'
_diffrn_measurement_method       'OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10035
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.82
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3757
_reflns_number_gt                3490
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART APEX II'
_computing_cell_refinement       'BRUKER SMART APEX II'
_computing_data_reduction        'BRUKER AXS SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Version 1.06) and CAMERON'
_computing_publication_material  'SHELXL97 and PARST 95 (Nardelli, 1995)'

_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^)+(0.0487P)^2^+0.4662P] 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       0.052(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3757
_refine_ls_number_parameters     337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
N1 N 0.63363(15) 0.27202(10) 0.46715(9) 0.0186(2) Uani 1 1 d . . .
H1 H 0.5806 0.2199 0.4060 0.022 Uiso 1 1 calc R . .
C1 C 0.65441(19) 0.23587(13) 0.54640(11) 0.0215(3) Uani 1 1 d . . .
H1A H 0.6157 0.1551 0.5340 0.026 Uiso 1 1 calc R . .
C2 C 0.73305(19) 0.31791(13) 0.64650(11) 0.0246(3) Uani 1 1 d . . .
H2 H 0.7455 0.2941 0.7025 0.029 Uiso 1 1 calc R . .
C3 C 0.79310(19) 0.43658(13) 0.66193(11) 0.0243(3) Uani 1 1 d . . .
H3A H 0.8466 0.4934 0.7289 0.029 Uiso 1 1 calc R . .
C4 C 0.77362(19) 0.47091(12) 0.57759(11) 0.0215(3) Uani 1 1 d . . .
H4A H 0.8153 0.5503 0.5876 0.026 Uiso 1 1 calc R . .
C5 C 0.69169(18) 0.38619(12) 0.47832(10) 0.0184(3) Uani 1 1 d . . .
C6 C 0.66070(18) 0.41198(12) 0.38250(10) 0.0184(3) Uani 1 1 d . . .
C7 C 0.72358(18) 0.52377(12) 0.38215(11) 0.0199(3) Uani 1 1 d . . .
H7 H 0.7873 0.5863 0.4432 0.024 Uiso 1 1 calc R . .
C8 C 0.68910(18) 0.54004(12) 0.28857(11) 0.0201(3) Uani 1 1 d . . .
C9 C 0.59176(19) 0.44456(12) 0.19902(11) 0.0208(3) Uani 1 1 d . . .
H9 H 0.5655 0.4530 0.1356 0.025 Uiso 1 1 calc R . .
C10 C 0.53486(18) 0.33602(12) 0.20731(10) 0.0189(3) Uani 1 1 d . . .
N2 N 0.56877(15) 0.31943(10) 0.29654(9) 0.0191(2) Uani 1 1 d . . .
C11 C 0.43364(18) 0.22821(12) 0.11606(10) 0.0191(3) Uani 1 1 d . . .
C12 C 0.4389(2) 0.20260(13) 0.01041(11) 0.0235(3) Uani 1 1 d . . .
H12 H 0.5010 0.2584 -0.0087 0.028 Uiso 1 1 calc R . .
C13 C 0.3504(2) 0.09249(13) -0.06753(11) 0.0251(3) Uani 1 1 d . . .
H13 H 0.3554 0.0739 -0.1391 0.030 Uiso 1 1 calc R . .
C14 C 0.25524(19) 0.01056(13) -0.03924(11) 0.0235(3) Uani 1 1 d . . .
H14 H 0.1957 -0.0631 -0.0910 0.028 Uiso 1 1 calc R . .
C15 C 0.25041(19) 0.04029(13) 0.06729(11) 0.0239(3) Uani 1 1 d . . .
H15 H 0.1865 -0.0132 0.0881 0.029 Uiso 1 1 calc R . .
N3 N 0.33787(16) 0.14632(10) 0.14068(9) 0.0209(3) Uani 1 1 d . . .
H3 H 0.3329 0.1632 0.2067 0.025 Uiso 1 1 calc R . .
C16 C 0.75857(18) 0.65704(12) 0.28500(11) 0.0199(3) Uani 1 1 d . . .
C17 C 0.76738(19) 0.77030(13) 0.37458(11) 0.0217(3) Uani 1 1 d . . .
H17 H 0.7262 0.7738 0.4370 0.026 Uiso 1 1 calc R . .
C18 C 0.83718(19) 0.87653(13) 0.36995(11) 0.0241(3) Uani 1 1 d . . .
H18 H 0.8403 0.9525 0.4288 0.029 Uiso 1 1 calc R . .
N4 N 0.90061(16) 0.87083(11) 0.28112(9) 0.0241(3) Uani 1 1 d . . .
H4 H 0.9459 0.9380 0.2800 0.029 Uiso 1 1 calc R . .
C19 C 0.8961(2) 0.76380(13) 0.19353(11) 0.0254(3) Uani 1 1 d . . .
H19 H 0.9425 0.7629 0.1332 0.031 Uiso 1 1 calc R . .
C20 C 0.8229(2) 0.65566(13) 0.19302(11) 0.0243(3) Uani 1 1 d . . .
H20 H 0.8162 0.5818 0.1317 0.029 Uiso 1 1 calc R . .
N5 N 0.41324(17) -0.02780(11) 0.31603(9) 0.0246(3) Uani 1 1 d . . .
O1 O 0.3719(2) -0.13264(10) 0.24356(10) 0.0457(3) Uani 1 1 d . . .
O2 O 0.34727(16) 0.00582(10) 0.40292(8) 0.0325(3) Uani 1 1 d . . .
O3 O 0.52455(15) 0.04624(9) 0.30167(8) 0.0304(3) Uani 1 1 d . . .
N6 N 0.97814(17) 0.30889(11) 0.07985(10) 0.0279(3) Uani 1 1 d . . .
O4 O 0.88150(19) 0.23428(12) -0.00309(9) 0.0463(3) Uani 1 1 d . . .
O5 O 0.98383(19) 0.29509(12) 0.16318(10) 0.0466(3) Uani 1 1 d . . .
O6 O 1.0677(2) 0.39814(12) 0.07671(12) 0.0602(4) Uani 1 1 d . . .
N7 N 0.08269(16) 0.15980(10) 0.34450(9) 0.0221(3) Uani 1 1 d . . .
O7 O 0.05499(15) 0.06479(9) 0.25644(8) 0.0274(2) Uani 1 1 d . . .
O8 O -0.01538(15) 0.17133(12) 0.41562(9) 0.0381(3) Uani 1 1 d . . .
O9 O 0.21192(15) 0.23858(9) 0.35724(9) 0.0308(3) Uani 1 1 d . . .
O1W O 0.3195(2) 0.58823(14) 0.07463(12) 0.0586(4) Uani 1 1 d . . .
H1W1 H 0.2356 0.5437 0.0855 0.097(11) Uiso 1 1 d R . .
H2W1 H 0.2649 0.6502 0.0712 0.115(12) Uiso 1 1 d 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
N1 0.0196(6) 0.0160(5) 0.0182(5) 0.0051(4) 0.0022(4) -0.0001(4)
C1 0.0218(7) 0.0209(7) 0.0252(7) 0.0124(6) 0.0054(5) 0.0026(5)
C2 0.0247(7) 0.0299(8) 0.0228(7) 0.0147(6) 0.0023(5) 0.0029(6)
C3 0.0233(7) 0.0261(7) 0.0193(7) 0.0060(6) -0.0008(5) 0.0010(6)
C4 0.0214(7) 0.0179(6) 0.0231(7) 0.0072(5) 0.0008(5) -0.0006(5)
C5 0.0163(6) 0.0177(6) 0.0211(7) 0.0076(5) 0.0038(5) 0.0020(5)
C6 0.0168(6) 0.0178(6) 0.0193(6) 0.0064(5) 0.0029(5) 0.0012(5)
C7 0.0191(6) 0.0180(6) 0.0206(6) 0.0064(5) 0.0019(5) -0.0004(5)
C8 0.0184(6) 0.0183(6) 0.0240(7) 0.0087(5) 0.0051(5) 0.0016(5)
C9 0.0217(7) 0.0211(7) 0.0209(7) 0.0099(6) 0.0033(5) 0.0014(5)
C10 0.0180(6) 0.0187(7) 0.0196(6) 0.0073(5) 0.0035(5) 0.0014(5)
N2 0.0192(6) 0.0179(6) 0.0194(6) 0.0070(5) 0.0029(4) 0.0003(4)
C11 0.0178(6) 0.0181(6) 0.0212(7) 0.0081(5) 0.0021(5) 0.0022(5)
C12 0.0255(7) 0.0242(7) 0.0223(7) 0.0111(6) 0.0031(5) 0.0016(6)
C13 0.0265(7) 0.0289(7) 0.0180(7) 0.0080(6) 0.0016(5) 0.0060(6)
C14 0.0206(7) 0.0222(7) 0.0210(7) 0.0032(5) -0.0011(5) 0.0018(5)
C15 0.0237(7) 0.0199(7) 0.0243(7) 0.0058(6) 0.0022(5) -0.0030(5)
N3 0.0247(6) 0.0199(6) 0.0163(5) 0.0059(5) 0.0024(4) -0.0023(5)
C16 0.0176(6) 0.0192(7) 0.0234(7) 0.0101(5) 0.0003(5) 0.0007(5)
C17 0.0212(7) 0.0222(7) 0.0218(7) 0.0097(6) 0.0019(5) -0.0006(5)
C18 0.0247(7) 0.0207(7) 0.0242(7) 0.0076(6) 0.0001(5) -0.0012(5)
N4 0.0259(6) 0.0195(6) 0.0290(6) 0.0132(5) -0.0003(5) -0.0035(5)
C19 0.0287(7) 0.0263(7) 0.0242(7) 0.0133(6) 0.0043(6) 0.0000(6)
C20 0.0294(7) 0.0202(7) 0.0220(7) 0.0078(6) 0.0030(6) 0.0008(6)
N5 0.0308(6) 0.0206(6) 0.0232(6) 0.0101(5) 0.0021(5) 0.0025(5)
O1 0.0693(9) 0.0213(6) 0.0368(7) 0.0020(5) 0.0118(6) -0.0109(5)
O2 0.0439(6) 0.0342(6) 0.0252(5) 0.0168(5) 0.0095(5) 0.0056(5)
O3 0.0348(6) 0.0236(5) 0.0276(5) 0.0050(4) 0.0086(4) -0.0048(4)
N6 0.0275(6) 0.0212(6) 0.0301(7) 0.0060(5) 0.0032(5) 0.0030(5)
O4 0.0550(8) 0.0410(7) 0.0314(6) 0.0068(5) -0.0030(5) -0.0211(6)
O5 0.0578(8) 0.0500(8) 0.0340(7) 0.0204(6) -0.0001(6) 0.0078(6)
O6 0.0798(11) 0.0364(7) 0.0569(9) 0.0154(6) -0.0012(7) -0.0259(7)
N7 0.0223(6) 0.0202(6) 0.0223(6) 0.0076(5) 0.0016(5) 0.0014(5)
O7 0.0389(6) 0.0206(5) 0.0197(5) 0.0062(4) 0.0026(4) -0.0059(4)
O8 0.0290(6) 0.0538(7) 0.0275(6) 0.0115(5) 0.0110(5) 0.0054(5)
O9 0.0333(6) 0.0193(5) 0.0366(6) 0.0100(4) -0.0008(5) -0.0065(4)
O1W 0.0579(9) 0.0528(9) 0.0727(10) 0.0329(8) 0.0100(7) 0.0103(7)

_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
N1 C1 1.3355(17) . ?
N1 C5 1.3482(17) . ?
N1 H1 0.8600 . ?
C1 C2 1.378(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.384(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.3866(19) . ?
C4 H4A 0.9300 . ?
C5 C6 1.4837(18) . ?
C6 N2 1.3385(17) . ?
C6 C7 1.3930(18) . ?
C7 C8 1.3925(19) . ?
C7 H7 0.9300 . ?
C8 C9 1.3941(19) . ?
C8 C16 1.4859(18) . ?
C9 C10 1.3950(18) . ?
C9 H9 0.9300 . ?
C10 N2 1.3353(17) . ?
C10 C11 1.4840(18) . ?
C11 N3 1.3521(17) . ?
C11 C12 1.3761(19) . ?
C12 C13 1.391(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(2) . ?
C14 H14 0.9300 . ?
C15 N3 1.3377(17) . ?
C15 H15 0.9300 . ?
N3 H3 0.8600 . ?
C16 C17 1.3960(19) . ?
C16 C20 1.3970(19) . ?
C17 C18 1.3741(19) . ?
C17 H17 0.9300 . ?
C18 N4 1.3352(18) . ?
C18 H18 0.9300 . ?
N4 C19 1.3417(19) . ?
N4 H4 0.8600 . ?
C19 C20 1.372(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
N5 O1 1.2378(16) . ?
N5 O2 1.2512(15) . ?
N5 O3 1.2641(15) . ?
N6 O5 1.2329(17) . ?
N6 O6 1.2454(17) . ?
N6 O4 1.2498(17) . ?
N7 O8 1.2347(16) . ?
N7 O9 1.2485(15) . ?
N7 O7 1.2664(15) . ?
O1W H1W1 0.8586 . ?
O1W H2W1 0.8559 . ?

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
C1 N1 C5 123.23(11) . . ?
C1 N1 H1 118.4 . . ?
C5 N1 H1 118.4 . . ?
N1 C1 C2 120.15(13) . . ?
N1 C1 H1A 119.9 . . ?
C2 C1 H1A 119.9 . . ?
C1 C2 C3 118.59(13) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 120.08(13) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C5 C4 C3 119.63(12) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
N1 C5 C4 118.28(12) . . ?
N1 C5 C6 116.91(11) . . ?
C4 C5 C6 124.80(12) . . ?
N2 C6 C7 122.72(12) . . ?
N2 C6 C5 114.86(11) . . ?
C7 C6 C5 122.42(11) . . ?
C8 C7 C6 118.65(12) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C7 C8 C9 118.96(12) . . ?
C7 C8 C16 119.88(12) . . ?
C9 C8 C16 121.16(12) . . ?
C8 C9 C10 118.08(12) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 . . ?
N2 C10 C9 123.26(12) . . ?
N2 C10 C11 114.51(11) . . ?
C9 C10 C11 122.22(12) . . ?
C10 N2 C6 118.32(11) . . ?
N3 C11 C12 118.56(12) . . ?
N3 C11 C10 116.04(11) . . ?
C12 C11 C10 125.30(12) . . ?
C11 C12 C13 119.41(13) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 120.35(13) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 118.61(13) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
N3 C15 C14 119.86(13) . . ?
N3 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 N3 C11 123.20(12) . . ?
C15 N3 H3 118.4 . . ?
C11 N3 H3 118.4 . . ?
C17 C16 C20 118.38(12) . . ?
C17 C16 C8 120.83(12) . . ?
C20 C16 C8 120.75(12) . . ?
C18 C17 C16 119.61(13) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
N4 C18 C17 120.13(13) . . ?
N4 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 N4 C19 122.18(12) . . ?
C18 N4 H4 118.9 . . ?
C19 N4 H4 118.9 . . ?
N4 C19 C20 119.99(13) . . ?
N4 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C16 119.68(13) . . ?
C19 C20 H20 120.2 . . ?
C16 C20 H20 120.2 . . ?
O1 N5 O2 121.24(12) . . ?
O1 N5 O3 119.12(12) . . ?
O2 N5 O3 119.64(11) . . ?
O5 N6 O6 120.64(13) . . ?
O5 N6 O4 120.86(13) . . ?
O6 N6 O4 118.51(13) . . ?
O8 N7 O9 121.84(12) . . ?
O8 N7 O7 119.72(12) . . ?
O9 N7 O7 118.44(11) . . ?
H1W1 O1W H2W1 106.4 . . ?

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
C5 N1 C1 C2 2.1(2) . . . . ?
N1 C1 C2 C3 -1.4(2) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C1 N1 C5 C4 -1.32(19) . . . . ?
C1 N1 C5 C6 179.30(11) . . . . ?
C3 C4 C5 N1 -0.16(19) . . . . ?
C3 C4 C5 C6 179.17(12) . . . . ?
N1 C5 C6 N2 3.30(17) . . . . ?
C4 C5 C6 N2 -176.04(12) . . . . ?
N1 C5 C6 C7 -176.36(11) . . . . ?
C4 C5 C6 C7 4.3(2) . . . . ?
N2 C6 C7 C8 0.12(19) . . . . ?
C5 C6 C7 C8 179.75(12) . . . . ?
C6 C7 C8 C9 0.53(19) . . . . ?
C6 C7 C8 C16 -178.49(11) . . . . ?
C7 C8 C9 C10 -0.64(19) . . . . ?
C16 C8 C9 C10 178.37(12) . . . . ?
C8 C9 C10 N2 0.11(19) . . . . ?
C8 C9 C10 C11 -178.84(12) . . . . ?
C9 C10 N2 C6 0.52(19) . . . . ?
C11 C10 N2 C6 179.55(11) . . . . ?
C7 C6 N2 C10 -0.64(19) . . . . ?
C5 C6 N2 C10 179.70(11) . . . . ?
N2 C10 C11 N3 20.32(16) . . . . ?
C9 C10 C11 N3 -160.64(12) . . . . ?
N2 C10 C11 C12 -155.88(13) . . . . ?
C9 C10 C11 C12 23.2(2) . . . . ?
N3 C11 C12 C13 -1.7(2) . . . . ?
C10 C11 C12 C13 174.43(12) . . . . ?
C11 C12 C13 C14 1.2(2) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C14 C15 N3 -0.4(2) . . . . ?
C14 C15 N3 C11 -0.1(2) . . . . ?
C12 C11 N3 C15 1.2(2) . . . . ?
C10 C11 N3 C15 -175.27(12) . . . . ?
C7 C8 C16 C17 -33.73(18) . . . . ?
C9 C8 C16 C17 147.26(13) . . . . ?
C7 C8 C16 C20 143.97(13) . . . . ?
C9 C8 C16 C20 -35.04(19) . . . . ?
C20 C16 C17 C18 0.4(2) . . . . ?
C8 C16 C17 C18 178.16(12) . . . . ?
C16 C17 C18 N4 -1.7(2) . . . . ?
C17 C18 N4 C19 1.2(2) . . . . ?
C18 N4 C19 C20 0.6(2) . . . . ?
N4 C19 C20 C16 -1.9(2) . . . . ?
C17 C16 C20 C19 1.4(2) . . . . ?
C8 C16 C20 C19 -176.38(12) . . . . ?

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
N1 H1 N2 0.86 2.28 2.6575(15) 106.9 .
N3 H3 N2 0.86 2.32 2.6661(15) 104.3 .
N1 H1 O3 0.86 1.97 2.7399(15) 148.9 .
N3 H3 O7 0.86 2.58 3.0855(15) 118.3 .
N3 H3 O9 0.86 2.19 2.9890(16) 155.4 .
N4 H4 O7 0.86 1.84 2.6941(15) 170.6 1_665
O1W H1W1 O6 0.86 2.04 2.871(2) 163.5 1_455
O1W H2W1 O4 0.86 2.19 3.013(2) 159.9 2_665
C1 H1A O2 0.93 2.42 3.2215(17) 144.7 2_656
C1 H1A O2 0.93 2.58 3.2616(18) 130.6 .
C2 H2 O1 0.93 2.49 3.2680(19) 141.7 2_656
C3 H3A O5 0.93 2.53 3.3440(19) 146.2 2_766
C3 H3A O6 0.93 2.47 3.366(2) 162.3 2_766
C4 H4A O9 0.93 2.31 3.1714(17) 153.6 2_666
C13 H13 O3 0.93 2.38 3.2109(17) 149.1 2_655
C15 H15 O7 0.93 2.43 3.0157(17) 121.0 .
C15 H15 O4 0.93 2.40 3.0940(19) 131.4 2_655
C19 H19 O4 0.93 2.32 3.2345(19) 168.1 2_765

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.040