# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d373
_database_code_depnum_ccdc_archive 'CCDC 1457776'
_audit_update_record             
;
2016-03-03 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'pyrrole-2,5-diacetic acid phenyl bisamide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 N3 O2'
_chemical_formula_weight         333.38

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc

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

_cell_length_a                   11.6197(3)
_cell_length_b                   9.4493(4)
_cell_length_c                   30.4715(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.932(2)
_cell_angle_gamma                90.00
_cell_volume                     3341.3(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK - An Oxford Diffraction program 
;
_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  KM4CCD
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 8.6479
_diffrn_standards_number         '1 frame'
_diffrn_standards_interval_count '50 frame'
_diffrn_standards_interval_time  '1200 sec'
_diffrn_standards_decay_%        2
_diffrn_reflns_number            17472
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         26.50
_reflns_number_total             3471
_reflns_number_gt                3181
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta 
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta 
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond 1.2'
_computing_publication_material  SHELXTL-97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1002P)²+1.8899P] where P=(Fo²+2Fc²)/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     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(10)
_refine_ls_number_reflns         3471
_refine_ls_number_parameters     451
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1512
_refine_ls_wR_factor_gt          0.1479
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_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
N1A N 0.6167(3) 0.1464(4) 0.15555(13) 0.0185(8) Uani 1 1 d . . .
H1A H 0.6203 0.0602 0.1448 0.022 Uiso 1 1 calc R . .
C2A C 0.6859(3) 0.2433(3) 0.13790(12) 0.0178(7) Uani 1 1 d . . .
O1A O 0.6928(3) 0.3675(2) 0.15074(9) 0.0237(6) Uani 1 1 d . . .
C3A C 0.7581(3) 0.1882(4) 0.10097(12) 0.0204(7) Uani 1 1 d . . .
H3A1 H 0.8357 0.1629 0.1134 0.024 Uiso 1 1 calc R . .
H3A2 H 0.7219 0.1010 0.0887 0.024 Uiso 1 1 calc R . .
C4A C 0.7705(4) 0.2933(4) 0.06435(15) 0.0145(8) Uani 1 1 d . . .
N5A N 0.8688(3) 0.3746(3) 0.06134(11) 0.0163(6) Uani 1 1 d . . .
H5A H 0.9285 0.3735 0.0803 0.020 Uiso 1 1 calc R . .
C6A C 0.8595(4) 0.4575(4) 0.02424(15) 0.0169(9) Uani 1 1 d . . .
C7A C 0.9540(3) 0.5582(4) 0.01278(12) 0.0193(7) Uani 1 1 d . . .
H7A1 H 1.0067 0.5720 0.0390 0.023 Uiso 1 1 calc R . .
H7A2 H 0.9193 0.6512 0.0050 0.023 Uiso 1 1 calc R . .
C8A C 1.0237(3) 0.5070(3) -0.02535(12) 0.0169(7) Uani 1 1 d . . .
O2A O 1.0655(2) 0.3855(2) -0.02574(9) 0.0194(5) Uani 1 1 d . . .
N9A N 1.0385(3) 0.6051(4) -0.05741(13) 0.0176(8) Uani 1 1 d . . .
H9A H 1.0038 0.6875 -0.0555 0.021 Uiso 1 1 calc R . .
C10A C 1.1088(4) 0.5794(5) -0.09455(15) 0.0200(10) Uani 1 1 d . . .
C11A C 1.2025(4) 0.6733(4) -0.09918(16) 0.0193(9) Uani 1 1 d . . .
H11A H 1.2169 0.7487 -0.0790 0.023 Uiso 1 1 calc R . .
C12A C 1.2734(5) 0.6512(6) -0.13455(18) 0.0276(11) Uani 1 1 d . . .
H12A H 1.3383 0.7104 -0.1381 0.033 Uiso 1 1 calc R . .
C13A C 1.2485(4) 0.5436(5) -0.16401(17) 0.0277(11) Uani 1 1 d . . .
H13A H 1.2959 0.5308 -0.1882 0.033 Uiso 1 1 calc R . .
C14A C 1.1563(5) 0.4540(5) -0.15916(16) 0.0279(11) Uani 1 1 d . . .
H14A H 1.1411 0.3801 -0.1798 0.033 Uiso 1 1 calc R . .
C15A C 1.0849(4) 0.4719(5) -0.12376(16) 0.0241(10) Uani 1 1 d . . .
H15A H 1.0212 0.4107 -0.1201 0.029 Uiso 1 1 calc R . .
C16A C 0.5387(4) 0.1663(4) 0.18937(14) 0.0159(9) Uani 1 1 d . . .
C17A C 0.4358(4) 0.0932(4) 0.18816(16) 0.0205(10) Uani 1 1 d . . .
H17A H 0.4179 0.0302 0.1645 0.025 Uiso 1 1 calc R . .
C18A C 0.3583(4) 0.1100(5) 0.22071(16) 0.0228(10) Uani 1 1 d . . .
H18A H 0.2888 0.0569 0.2194 0.027 Uiso 1 1 calc R . .
C19A C 0.3809(4) 0.2047(5) 0.25579(17) 0.0238(10) Uani 1 1 d . . .
H19A H 0.3262 0.2196 0.2775 0.029 Uiso 1 1 calc R . .
C20A C 0.4870(4) 0.2763(5) 0.25765(16) 0.0260(10) Uani 1 1 d . . .
H20A H 0.5050 0.3384 0.2816 0.031 Uiso 1 1 calc R . .
C21A C 0.5662(4) 0.2589(5) 0.22542(15) 0.0211(9) Uani 1 1 d . . .
H21A H 0.6377 0.3078 0.2273 0.025 Uiso 1 1 calc R . .
C22A C 0.7000(3) 0.3218(4) 0.02746(13) 0.0195(7) Uani 1 1 d . . .
H22A H 0.6273 0.2795 0.0202 0.023 Uiso 1 1 calc R . .
C23A C 0.7561(3) 0.4261(4) 0.00223(12) 0.0188(7) Uani 1 1 d . . .
H23A H 0.7275 0.4663 -0.0247 0.023 Uiso 1 1 calc R . .
N1B N 1.0281(3) 1.1065(4) -0.06268(12) 0.0154(8) Uani 1 1 d . . .
H1B H 1.0270 1.1927 -0.0517 0.019 Uiso 1 1 calc R . .
C2B C 0.9588(3) 1.0062(4) -0.04482(12) 0.0183(7) Uani 1 1 d . . .
O1B O 0.9504(3) 0.8819(2) -0.05749(9) 0.0246(6) Uani 1 1 d . . .
C3B C 0.8881(3) 1.0621(3) -0.00760(12) 0.0197(7) Uani 1 1 d . . .
H3B1 H 0.9261 1.1483 0.0047 0.024 Uiso 1 1 calc R . .
H3B2 H 0.8111 1.0901 -0.0200 0.024 Uiso 1 1 calc R . .
C4B C 0.8727(4) 0.9590(4) 0.02922(15) 0.0173(9) Uani 1 1 d . . .
N5B N 0.7764(3) 0.8753(3) 0.03155(11) 0.0160(6) Uani 1 1 d . . .
H5B H 0.7185 0.8738 0.0118 0.019 Uiso 1 1 calc R . .
C6B C 0.7831(4) 0.7939(4) 0.06914(14) 0.0155(9) Uani 1 1 d . . .
C7B C 0.6906(3) 0.6916(4) 0.07989(12) 0.0192(7) Uani 1 1 d . . .
H7B1 H 0.7260 0.5989 0.0875 0.023 Uiso 1 1 calc R . .
H7B2 H 0.6379 0.6780 0.0537 0.023 Uiso 1 1 calc R . .
C8B C 0.6214(3) 0.7427(3) 0.11818(12) 0.0163(7) Uani 1 1 d . . .
O2B O 0.5792(2) 0.8645(2) 0.11849(9) 0.0191(5) Uani 1 1 d . . .
N9B N 0.6071(4) 0.6500(4) 0.15046(13) 0.0199(9) Uani 1 1 d . . .
H9B H 0.6443 0.5692 0.1492 0.024 Uiso 1 1 calc R . .
C10B C 0.5366(4) 0.6710(4) 0.18686(15) 0.0160(9) Uani 1 1 d . . .
C11B C 0.4425(5) 0.5861(5) 0.19359(16) 0.0202(10) Uani 1 1 d . . .
H11B H 0.4238 0.5120 0.1734 0.024 Uiso 1 1 calc R . .
C12B C 0.3748(4) 0.6066(5) 0.22912(17) 0.0251(11) Uani 1 1 d . . .
H12B H 0.3103 0.5469 0.2328 0.030 Uiso 1 1 calc R . .
C13B C 0.4003(5) 0.7144(5) 0.25976(17) 0.0255(10) Uani 1 1 d . . .
H13B H 0.3527 0.7303 0.2837 0.031 Uiso 1 1 calc R . .
C14B C 0.4988(5) 0.7987(5) 0.25383(17) 0.0266(10) Uani 1 1 d . . .
H14B H 0.5193 0.8699 0.2748 0.032 Uiso 1 1 calc R . .
C15B C 0.5664(4) 0.7794(5) 0.21789(16) 0.0221(10) Uani 1 1 d . . .
H15B H 0.6317 0.8379 0.2141 0.027 Uiso 1 1 calc R . .
C16B C 1.1026(4) 1.0801(5) -0.09818(14) 0.0173(9) Uani 1 1 d . . .
C17B C 1.2088(4) 1.1554(5) -0.09551(17) 0.0221(10) Uani 1 1 d . . .
H17B H 1.2271 1.2180 -0.0718 0.027 Uiso 1 1 calc R . .
C18B C 1.2859(4) 1.1344(5) -0.12907(18) 0.0256(11) Uani 1 1 d . . .
H18B H 1.3583 1.1814 -0.1279 0.031 Uiso 1 1 calc R . .
C19B C 1.2561(5) 1.0456(5) -0.16367(18) 0.0289(11) Uani 1 1 d . . .
H19B H 1.3081 1.0334 -0.1864 0.035 Uiso 1 1 calc R . .
C20B C 1.1527(4) 0.9741(5) -0.16598(16) 0.0246(10) Uani 1 1 d . . .
H20B H 1.1344 0.9122 -0.1899 0.030 Uiso 1 1 calc R . .
C21B C 1.0744(4) 0.9929(5) -0.13290(15) 0.0217(9) Uani 1 1 d . . .
H21B H 1.0022 0.9453 -0.1346 0.026 Uiso 1 1 calc R . .
C22B C 0.9449(3) 0.9289(3) 0.06572(12) 0.0182(7) Uani 1 1 d . . .
H22B H 1.0182 0.9698 0.0727 0.022 Uiso 1 1 calc R . .
C23B C 0.8878(3) 0.8241(3) 0.09083(12) 0.0185(7) Uani 1 1 d . . .
H23B H 0.9167 0.7828 0.1176 0.022 Uiso 1 1 calc R . .


_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
N1A C2A 1.349(6) . ?
N1A C16A 1.419(6) . ?
N1A H1A 0.8800 . ?
C2A O1A 1.238(4) . ?
C2A C3A 1.528(4) . ?
C3A C4A 1.506(5) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4A C22A 1.383(6) . ?
C4A N5A 1.385(5) . ?
N5A C6A 1.375(5) . ?
N5A H5A 0.8800 . ?
C6A C23A 1.378(6) . ?
C6A C7A 1.507(5) . ?
C7A C8A 1.529(4) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A O2A 1.247(4) . ?
C8A N9A 1.364(6) . ?
N9A C10A 1.450(6) . ?
N9A H9A 0.8800 . ?
C10A C15A 1.370(6) . ?
C10A C11A 1.417(6) . ?
C11A C12A 1.405(7) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.377(7) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.379(7) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.404(7) . ?
C14A H14A 0.9500 . ?
C15A H15A 0.9500 . ?
C16A C17A 1.379(7) . ?
C16A C21A 1.428(6) . ?
C17A C18A 1.382(7) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.408(7) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.405(7) . ?
C19A H19A 0.9500 . ?
C20A C21A 1.390(7) . ?
C20A H20A 0.9500 . ?
C21A H21A 0.9500 . ?
C22A C23A 1.428(5) . ?
C22A H22A 0.9500 . ?
C23A H23A 0.9500 . ?
N1B C2B 1.375(5) . ?
N1B C16B 1.442(6) . ?
N1B H1B 0.8800 . ?
C2B O1B 1.239(4) . ?
C2B C3B 1.528(4) . ?
C3B C4B 1.504(6) . ?
C3B H3B1 0.9900 . ?
C3B H3B2 0.9900 . ?
C4B N5B 1.375(5) . ?
C4B C22B 1.388(6) . ?
N5B C6B 1.378(5) . ?
N5B H5B 0.8800 . ?
C6B C23B 1.385(6) . ?
C6B C7B 1.495(5) . ?
C7B C8B 1.529(4) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B O2B 1.251(4) . ?
C8B N9B 1.334(6) . ?
N9B C10B 1.426(6) . ?
N9B H9B 0.8800 . ?
C10B C11B 1.380(6) . ?
C10B C15B 1.425(6) . ?
C11B C12B 1.384(7) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.403(7) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.414(7) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.392(7) . ?
C14B H14B 0.9500 . ?
C15B H15B 0.9500 . ?
C16B C21B 1.368(6) . ?
C16B C17B 1.423(6) . ?
C17B C18B 1.408(7) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.378(7) . ?
C18B H18B 0.9500 . ?
C19B C20B 1.378(7) . ?
C19B H19B 0.9500 . ?
C20B C21B 1.403(7) . ?
C20B H20B 0.9500 . ?
C21B H21B 0.9500 . ?
C22B C23B 1.434(5) . ?
C22B H22B 0.9500 . ?
C23B H23B 0.9500 . ?

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
C2A N1A C16A 128.0(4) . . ?
C2A N1A H1A 116.0 . . ?
C16A N1A H1A 116.0 . . ?
O1A C2A N1A 123.2(3) . . ?
O1A C2A C3A 121.8(3) . . ?
N1A C2A C3A 115.0(3) . . ?
C4A C3A C2A 113.5(3) . . ?
C4A C3A H3A1 108.9 . . ?
C2A C3A H3A1 108.9 . . ?
C4A C3A H3A2 108.9 . . ?
C2A C3A H3A2 108.9 . . ?
H3A1 C3A H3A2 107.7 . . ?
C22A C4A N5A 107.1(4) . . ?
C22A C4A C3A 131.0(4) . . ?
N5A C4A C3A 121.7(4) . . ?
C6A N5A C4A 109.9(3) . . ?
C6A N5A H5A 125.1 . . ?
C4A N5A H5A 125.1 . . ?
N5A C6A C23A 107.9(3) . . ?
N5A C6A C7A 121.5(4) . . ?
C23A C6A C7A 130.6(4) . . ?
C6A C7A C8A 113.4(3) . . ?
C6A C7A H7A1 108.9 . . ?
C8A C7A H7A1 108.9 . . ?
C6A C7A H7A2 108.9 . . ?
C8A C7A H7A2 108.9 . . ?
H7A1 C7A H7A2 107.7 . . ?
O2A C8A N9A 123.8(3) . . ?
O2A C8A C7A 121.4(3) . . ?
N9A C8A C7A 114.8(3) . . ?
C8A N9A C10A 122.8(4) . . ?
C8A N9A H9A 118.6 . . ?
C10A N9A H9A 118.6 . . ?
C15A C10A C11A 122.1(4) . . ?
C15A C10A N9A 121.9(4) . . ?
C11A C10A N9A 116.1(4) . . ?
C12A C11A C10A 117.8(4) . . ?
C12A C11A H11A 121.1 . . ?
C10A C11A H11A 121.1 . . ?
C13A C12A C11A 119.9(5) . . ?
C13A C12A H12A 120.1 . . ?
C11A C12A H12A 120.1 . . ?
C12A C13A C14A 121.4(5) . . ?
C12A C13A H13A 119.3 . . ?
C14A C13A H13A 119.3 . . ?
C13A C14A C15A 120.1(5) . . ?
C13A C14A H14A 120.0 . . ?
C15A C14A H14A 120.0 . . ?
C10A C15A C14A 118.7(5) . . ?
C10A C15A H15A 120.6 . . ?
C14A C15A H15A 120.6 . . ?
C17A C16A N1A 119.9(4) . . ?
C17A C16A C21A 119.1(4) . . ?
N1A C16A C21A 120.9(4) . . ?
C16A C17A C18A 121.3(4) . . ?
C16A C17A H17A 119.4 . . ?
C18A C17A H17A 119.4 . . ?
C17A C18A C19A 121.0(5) . . ?
C17A C18A H18A 119.5 . . ?
C19A C18A H18A 119.5 . . ?
C20A C19A C18A 117.8(5) . . ?
C20A C19A H19A 121.1 . . ?
C18A C19A H19A 121.1 . . ?
C21A C20A C19A 121.7(5) . . ?
C21A C20A H20A 119.1 . . ?
C19A C20A H20A 119.1 . . ?
C20A C21A C16A 119.1(5) . . ?
C20A C21A H21A 120.5 . . ?
C16A C21A H21A 120.5 . . ?
C4A C22A C23A 107.7(3) . . ?
C4A C22A H22A 126.1 . . ?
C23A C22A H22A 126.1 . . ?
C6A C23A C22A 107.3(3) . . ?
C6A C23A H23A 126.3 . . ?
C22A C23A H23A 126.3 . . ?
C2B N1B C16B 124.3(4) . . ?
C2B N1B H1B 117.8 . . ?
C16B N1B H1B 117.8 . . ?
O1B C2B N1B 124.7(3) . . ?
O1B C2B C3B 121.5(3) . . ?
N1B C2B C3B 113.8(3) . . ?
C4B C3B C2B 114.7(3) . . ?
C4B C3B H3B1 108.6 . . ?
C2B C3B H3B1 108.6 . . ?
C4B C3B H3B2 108.6 . . ?
C2B C3B H3B2 108.6 . . ?
H3B1 C3B H3B2 107.6 . . ?
N5B C4B C22B 107.5(4) . . ?
N5B C4B C3B 122.7(4) . . ?
C22B C4B C3B 129.9(4) . . ?
C4B N5B C6B 110.7(4) . . ?
C4B N5B H5B 124.7 . . ?
C6B N5B H5B 124.7 . . ?
N5B C6B C23B 107.0(4) . . ?
N5B C6B C7B 122.2(4) . . ?
C23B C6B C7B 130.8(4) . . ?
C6B C7B C8B 112.0(3) . . ?
C6B C7B H7B1 109.2 . . ?
C8B C7B H7B1 109.2 . . ?
C6B C7B H7B2 109.2 . . ?
C8B C7B H7B2 109.2 . . ?
H7B1 C7B H7B2 107.9 . . ?
O2B C8B N9B 122.3(3) . . ?
O2B C8B C7B 121.2(3) . . ?
N9B C8B C7B 116.5(3) . . ?
C8B N9B C10B 125.5(4) . . ?
C8B N9B H9B 117.2 . . ?
C10B N9B H9B 117.2 . . ?
C11B C10B C15B 119.2(4) . . ?
C11B C10B N9B 121.7(4) . . ?
C15B C10B N9B 119.1(4) . . ?
C10B C11B C12B 121.4(4) . . ?
C10B C11B H11B 119.3 . . ?
C12B C11B H11B 119.3 . . ?
C11B C12B C13B 120.9(5) . . ?
C11B C12B H12B 119.5 . . ?
C13B C12B H12B 119.5 . . ?
C12B C13B C14B 117.9(5) . . ?
C12B C13B H13B 121.0 . . ?
C14B C13B H13B 121.0 . . ?
C15B C14B C13B 121.3(5) . . ?
C15B C14B H14B 119.3 . . ?
C13B C14B H14B 119.3 . . ?
C14B C15B C10B 119.2(5) . . ?
C14B C15B H15B 120.4 . . ?
C10B C15B H15B 120.4 . . ?
C21B C16B C17B 121.3(4) . . ?
C21B C16B N1B 123.7(4) . . ?
C17B C16B N1B 115.0(4) . . ?
C18B C17B C16B 118.1(4) . . ?
C18B C17B H17B 121.0 . . ?
C16B C17B H17B 121.0 . . ?
C19B C18B C17B 119.8(5) . . ?
C19B C18B H18B 120.1 . . ?
C17B C18B H18B 120.1 . . ?
C20B C19B C18B 121.5(5) . . ?
C20B C19B H19B 119.3 . . ?
C18B C19B H19B 119.3 . . ?
C19B C20B C21B 119.8(5) . . ?
C19B C20B H20B 120.1 . . ?
C21B C20B H20B 120.1 . . ?
C16B C21B C20B 119.5(4) . . ?
C16B C21B H21B 120.2 . . ?
C20B C21B H21B 120.2 . . ?
C4B C22B C23B 107.0(3) . . ?
C4B C22B H22B 126.5 . . ?
C23B C22B H22B 126.5 . . ?
C6B C23B C22B 107.9(3) . . ?
C6B C23B H23B 126.1 . . ?
C22B C23B H23B 126.1 . . ?

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
C16A N1A C2A O1A 2.4(7) . . . . ?
C16A N1A C2A C3A -178.6(4) . . . . ?
O1A C2A C3A C4A -38.9(5) . . . . ?
N1A C2A C3A C4A 142.1(4) . . . . ?
C2A C3A C4A C22A -85.6(5) . . . . ?
C2A C3A C4A N5A 100.0(4) . . . . ?
C22A C4A N5A C6A 2.3(5) . . . . ?
C3A C4A N5A C6A 177.9(3) . . . . ?
C4A N5A C6A C23A -2.1(5) . . . . ?
C4A N5A C6A C7A 179.4(3) . . . . ?
N5A C6A C7A C8A 105.9(4) . . . . ?
C23A C6A C7A C8A -72.2(5) . . . . ?
C6A C7A C8A O2A -50.6(5) . . . . ?
C6A C7A C8A N9A 131.1(4) . . . . ?
O2A C8A N9A C10A -2.7(7) . . . . ?
C7A C8A N9A C10A 175.6(4) . . . . ?
C8A N9A C10A C15A 60.4(6) . . . . ?
C8A N9A C10A C11A -120.6(5) . . . . ?
C15A C10A C11A C12A -1.5(7) . . . . ?
N9A C10A C11A C12A 179.5(4) . . . . ?
C10A C11A C12A C13A 1.9(7) . . . . ?
C11A C12A C13A C14A -1.4(8) . . . . ?
C12A C13A C14A C15A 0.4(7) . . . . ?
C11A C10A C15A C14A 0.5(7) . . . . ?
N9A C10A C15A C14A 179.5(5) . . . . ?
C13A C14A C15A C10A 0.1(7) . . . . ?
C2A N1A C16A C17A 144.5(5) . . . . ?
C2A N1A C16A C21A -37.0(6) . . . . ?
N1A C16A C17A C18A 179.8(4) . . . . ?
C21A C16A C17A C18A 1.2(6) . . . . ?
C16A C17A C18A C19A 1.3(7) . . . . ?
C17A C18A C19A C20A -2.9(7) . . . . ?
C18A C19A C20A C21A 2.0(7) . . . . ?
C19A C20A C21A C16A 0.4(7) . . . . ?
C17A C16A C21A C20A -2.0(6) . . . . ?
N1A C16A C21A C20A 179.4(5) . . . . ?
N5A C4A C22A C23A -1.7(4) . . . . ?
C3A C4A C22A C23A -176.6(4) . . . . ?
N5A C6A C23A C22A 1.0(4) . . . . ?
C7A C6A C23A C22A 179.3(4) . . . . ?
C4A C22A C23A C6A 0.4(4) . . . . ?
C16B N1B C2B O1B -1.3(7) . . . . ?
C16B N1B C2B C3B -179.8(4) . . . . ?
O1B C2B C3B C4B 37.9(5) . . . . ?
N1B C2B C3B C4B -143.5(4) . . . . ?
C2B C3B C4B N5B -96.2(4) . . . . ?
C2B C3B C4B C22B 84.2(5) . . . . ?
C22B C4B N5B C6B 1.4(5) . . . . ?
C3B C4B N5B C6B -178.3(3) . . . . ?
C4B N5B C6B C23B -1.5(5) . . . . ?
C4B N5B C6B C7B -179.3(3) . . . . ?
N5B C6B C7B C8B -108.5(4) . . . . ?
C23B C6B C7B C8B 74.3(5) . . . . ?
C6B C7B C8B O2B 50.8(5) . . . . ?
C6B C7B C8B N9B -130.4(4) . . . . ?
O2B C8B N9B C10B 5.3(6) . . . . ?
C7B C8B N9B C10B -173.5(4) . . . . ?
C8B N9B C10B C11B 117.1(5) . . . . ?
C8B N9B C10B C15B -65.0(6) . . . . ?
C15B C10B C11B C12B 1.8(7) . . . . ?
N9B C10B C11B C12B 179.7(4) . . . . ?
C10B C11B C12B C13B -0.4(8) . . . . ?
C11B C12B C13B C14B -1.7(7) . . . . ?
C12B C13B C14B C15B 2.4(7) . . . . ?
C13B C14B C15B C10B -1.0(7) . . . . ?
C11B C10B C15B C14B -1.1(6) . . . . ?
N9B C10B C15B C14B -179.0(5) . . . . ?
C2B N1B C16B C21B 37.5(6) . . . . ?
C2B N1B C16B C17B -144.3(4) . . . . ?
C21B C16B C17B C18B -1.8(7) . . . . ?
N1B C16B C17B C18B 179.9(4) . . . . ?
C16B C17B C18B C19B 1.5(7) . . . . ?
C17B C18B C19B C20B -1.1(7) . . . . ?
C18B C19B C20B C21B 1.0(7) . . . . ?
C17B C16B C21B C20B 1.7(6) . . . . ?
N1B C16B C21B C20B 179.8(5) . . . . ?
C19B C20B C21B C16B -1.3(7) . . . . ?
N5B C4B C22B C23B -0.7(4) . . . . ?
C3B C4B C22B C23B 178.9(4) . . . . ?
N5B C6B C23B C22B 1.0(4) . . . . ?
C7B C6B C23B C22B 178.5(4) . . . . ?
C4B C22B C23B C6B -0.2(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
N1A H1A O2B 0.88 2.06 2.917(5) 163.9 1_545
N5A H5A O2B 0.88 2.05 2.929(4) 173.2 3_545
N9A H9A O1B 0.88 1.94 2.808(5) 169.4 .
N1B H1B O2A 0.88 2.03 2.890(4) 166.3 1_565
N5B H5B O2A 0.88 2.07 2.937(4) 169.6 3_455
N9B H9B O1A 0.88 1.99 2.849(5) 166.2 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.070
