# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_DEF
_database_code_depnum_ccdc_archive 'CCDC 1056915'
_audit_update_record             
;
2018-04-12 deposited with the CCDC.
2019-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C32 H21 N10 O7'
_chemical_formula_sum            'C32 H21 N10 O7'
_chemical_formula_weight         657.59

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                   10.1382(11)
_cell_length_b                   12.7716(14)
_cell_length_c                   13.5128(14)
_cell_angle_alpha                79.967(2)
_cell_angle_beta                 89.142(2)
_cell_angle_gamma                76.356(2)
_cell_volume                     1673.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4783
_cell_measurement_theta_min      0.997
_cell_measurement_theta_max      0.998

_exptl_crystal_description       rod
_exptl_crystal_colour            coloress
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             678
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.997
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            8458
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         23.31
_reflns_number_total             4783
_reflns_number_gt                3690
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL

_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)+(0.1258P)²+1.7152P] where P=(Fo²+2Fc²)/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_number_reflns         4783
_refine_ls_number_parameters     442
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.2265
_refine_ls_wR_factor_gt          0.2069
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.003
_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 0.97099(16) 0.78345(14) 0.54420(13) 0.0254(5) Uani 1 1 d . . .
C2 C 1.08778(16) 0.90699(14) 0.60471(13) 0.0245(5) Uani 1 1 d . . .
C3 C 0.89753(16) 0.85730(14) 0.69392(13) 0.0239(5) Uani 1 1 d . . .
C4 C 1.00103(16) 0.91351(14) 0.68435(13) 0.0260(5) Uani 1 1 d . . .
H4 H 1.0116 0.9556 0.7320 0.031 Uiso 1 1 calc R . .
C5 C 1.07275(16) 0.84115(14) 0.53568(13) 0.0256(5) Uani 1 1 d . . .
H5 H 1.1320 0.8355 0.4826 0.031 Uiso 1 1 calc R . .
C6 C 0.88193(16) 0.79387(14) 0.62382(13) 0.0256(5) Uani 1 1 d . . .
H6 H 0.8117 0.7579 0.6297 0.031 Uiso 1 1 calc R . .
C7 C 1.20274(16) 0.96310(14) 0.58997(13) 0.0252(5) Uani 1 1 d . . .
C8 C 0.96495(16) 0.71221(14) 0.46776(13) 0.0262(5) Uani 1 1 d . . .
C9 C 0.81365(17) 0.86309(14) 0.78553(13) 0.0281(5) Uani 1 1 d . . .
C10 C 1.31176(18) 1.15344(15) 0.70399(14) 0.0310(5) Uani 1 1 d . . .
H10 H 1.2399 1.1655 0.7474 0.037 Uiso 1 1 calc R . .
C11 C 1.41872(17) 1.21241(15) 0.70552(13) 0.0289(5) Uani 1 1 d . . .
C12 C 1.53665(19) 1.19266(17) 0.65081(14) 0.0389(6) Uani 1 1 d . . .
H12 H 1.5519 1.1395 0.6102 0.047 Uiso 1 1 calc R . .
C13 C 1.40386(19) 1.29193(15) 0.76556(15) 0.0355(6) Uani 1 1 d . . .
H13 H 1.3277 1.3068 0.8047 0.043 Uiso 1 1 calc R . .
C14 C 1.6306(2) 1.25375(18) 0.65821(16) 0.0483(6) Uani 1 1 d . . .
H14 H 1.7090 1.2396 0.6213 0.058 Uiso 1 1 calc R . .
C15 C 1.5045(2) 1.34893(16) 0.76624(17) 0.0443(6) Uani 1 1 d . . .
H15 H 1.4921 1.4031 0.8058 0.053 Uiso 1 1 calc R . .
C16 C 0.77693(18) 0.52180(15) 0.44631(15) 0.0337(5) Uani 1 1 d . . .
H16 H 0.7337 0.5258 0.5072 0.040 Uiso 1 1 calc R . .
C17 C 0.74420(18) 0.45007(15) 0.38154(14) 0.0318(5) Uani 1 1 d . . .
C18 C 0.8165(2) 0.42731(15) 0.29660(15) 0.0371(6) Uani 1 1 d . . .
H18 H 0.8897 0.4578 0.2777 0.045 Uiso 1 1 calc R . .
C19 C 0.6362(2) 0.40187(16) 0.40490(16) 0.0398(6) Uani 1 1 d . . .
H19 H 0.5853 0.4148 0.4613 0.048 Uiso 1 1 calc R . .
C20 C 0.6044(2) 0.33428(16) 0.34376(17) 0.0457(6) Uani 1 1 d . . .
H20 H 0.5315 0.3027 0.3608 0.055 Uiso 1 1 calc R . .
C21 C 0.7773(2) 0.35861(17) 0.24113(16) 0.0467(6) Uani 1 1 d . . .
H21 H 0.8274 0.3433 0.1850 0.056 Uiso 1 1 calc R . .
C22 C 0.47417(16) 0.86999(14) 0.83640(13) 0.0270(5) Uani 1 1 d . . .
H22 H 0.4460 0.8643 0.7728 0.032 Uiso 1 1 calc R . .
C23 C 0.37742(16) 0.87724(14) 0.91844(13) 0.0258(5) Uani 1 1 d . . .
C24 C 0.24321(17) 0.87446(15) 0.89949(14) 0.0294(5) Uani 1 1 d . . .
H24 H 0.2164 0.8656 0.8365 0.035 Uiso 1 1 calc R . .
C25 C 0.41167(17) 0.88913(15) 1.01418(14) 0.0299(5) Uani 1 1 d . . .
H25 H 0.4998 0.8914 1.0301 0.036 Uiso 1 1 calc R . .
C26 C 0.31248(18) 0.89753(15) 1.08512(14) 0.0321(5) Uani 1 1 d . . .
H26 H 0.3366 0.9052 1.1492 0.039 Uiso 1 1 calc R . .
C27 C 0.15107(18) 0.88496(15) 0.97541(14) 0.0320(5) Uani 1 1 d . . .
H27 H 0.0616 0.8847 0.9614 0.038 Uiso 1 1 calc R . .
C28 C 0.7905(2) 0.50396(17) 0.73148(17) 0.0431(6) Uani 1 1 d . . .
C29 C 0.7268(4) 0.5871(3) 0.8783(2) 0.0945(10) Uani 1 1 d U . .
C30 C 0.6252(4) 0.5791(3) 0.9479(3) 0.1258(13) Uani 1 1 d U . .
C31 C 0.8257(3) 0.38397(19) 0.8939(2) 0.0670(8) Uani 1 1 d . . .
C32 C 0.9521(4) 0.3789(3) 0.9539(3) 0.1097(13) Uani 1 1 d U . .
N1 N 1.20825(13) 1.03418(12) 0.65231(11) 0.0273(4) Uani 1 1 d . . .
H1 H 1.1468 1.0472 0.6961 0.033 Uiso 1 1 calc R . .
N2 N 1.31483(13) 1.08545(12) 0.64416(11) 0.0273(4) Uani 1 1 d . . .
N3 N 1.61734(17) 1.33130(15) 0.71416(14) 0.0482(5) Uani 1 1 d . . .
N4 N 0.88090(14) 0.64443(12) 0.48842(11) 0.0299(4) Uani 1 1 d . . .
H4A H 0.8379 0.6419 0.5438 0.036 Uiso 1 1 calc R . .
N5 N 0.86355(15) 0.57876(12) 0.42078(11) 0.0303(4) Uani 1 1 d . . .
N6 N 0.67247(18) 0.31216(14) 0.26200(14) 0.0500(5) Uani 1 1 d . . .
N7 N 0.68027(13) 0.86716(12) 0.77106(11) 0.0278(4) Uani 1 1 d . . .
H7 H 0.6482 0.8670 0.7125 0.033 Uiso 1 1 calc R . .
N8 N 0.59731(14) 0.87156(12) 0.85320(11) 0.0281(4) Uani 1 1 d . . .
N9 N 0.18346(14) 0.89541(12) 1.06765(11) 0.0304(4) Uani 1 1 d . . .
N10 N 0.7769(2) 0.49168(14) 0.83003(14) 0.0531(6) Uani 1 1 d . . .
O1 O 1.28830(11) 0.94334(10) 0.52643(9) 0.0342(4) Uani 1 1 d . . .
O2 O 1.03284(12) 0.71712(10) 0.39189(9) 0.0365(4) Uani 1 1 d . . .
O3 O 0.86479(12) 0.86330(12) 0.86639(9) 0.0411(4) Uani 1 1 d . . .
O4 O 0.75131(15) 0.59196(12) 0.67318(11) 0.0492(4) Uani 1 1 d . . .
O5 O 0.56947(12) 0.88104(11) 0.57641(9) 0.0373(4) Uani 1 1 d . . .
O6 O 1.01006(12) 0.12934(11) 0.78928(10) 0.0403(4) Uani 1 1 d . . .
O7 O 0.22993(19) 0.16266(17) 0.93142(13) 0.0774(6) Uani 1 1 d . . .


_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 C5 1.395(3) . ?
C1 C6 1.398(2) . ?
C1 C8 1.501(3) . ?
C2 C4 1.381(2) . ?
C2 C5 1.392(3) . ?
C2 C7 1.500(3) . ?
C3 C6 1.382(3) . ?
C3 C4 1.397(3) . ?
C3 C9 1.494(2) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.226(2) . ?
C7 N1 1.352(2) . ?
C8 O2 1.227(2) . ?
C8 N4 1.345(2) . ?
C9 O3 1.217(2) . ?
C9 N7 1.357(2) . ?
C10 N2 1.280(3) . ?
C10 C11 1.461(3) . ?
C10 H10 0.9300 . ?
C11 C13 1.387(3) . ?
C11 C12 1.391(3) . ?
C12 C14 1.381(3) . ?
C12 H12 0.9300 . ?
C13 C15 1.387(3) . ?
C13 H13 0.9300 . ?
C14 N3 1.329(3) . ?
C14 H14 0.9300 . ?
C15 N3 1.328(3) . ?
C15 H15 0.9300 . ?
C16 N5 1.274(3) . ?
C16 C17 1.465(3) . ?
C16 H16 0.9300 . ?
C17 C19 1.385(3) . ?
C17 C18 1.389(3) . ?
C18 C21 1.376(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(3) . ?
C19 H19 0.9300 . ?
C20 N6 1.331(3) . ?
C20 H20 0.9300 . ?
C21 N6 1.338(3) . ?
C21 H21 0.9300 . ?
C22 N8 1.278(2) . ?
C22 C23 1.470(2) . ?
C22 H22 0.9300 . ?
C23 C25 1.387(3) . ?
C23 C24 1.398(2) . ?
C24 C27 1.380(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.378(3) . ?
C25 H25 0.9300 . ?
C26 N9 1.340(2) . ?
C26 H26 0.9300 . ?
C27 N9 1.331(3) . ?
C27 H27 0.9300 . ?
C28 O4 1.238(2) . ?
C28 N10 1.322(3) . ?
C29 C30 1.394(6) . ?
C29 N10 1.465(4) . ?
C31 N10 1.470(3) . ?
C31 C32 1.509(5) . ?
N1 N2 1.383(2) . ?
N1 H1 0.8600 . ?
N4 N5 1.382(2) . ?
N4 H4A 0.8600 . ?
N7 N8 1.383(2) . ?
N7 H7 0.8600 . ?

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
C5 C1 C6 118.43(17) . . ?
C5 C1 C8 117.81(15) . . ?
C6 C1 C8 123.76(16) . . ?
C4 C2 C5 118.92(17) . . ?
C4 C2 C7 123.81(17) . . ?
C5 C2 C7 117.21(15) . . ?
C6 C3 C4 120.05(16) . . ?
C6 C3 C9 122.71(16) . . ?
C4 C3 C9 117.10(16) . . ?
C2 C4 C3 120.50(17) . . ?
C2 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C2 C5 C1 121.60(16) . . ?
C2 C5 H5 119.2 . . ?
C1 C5 H5 119.2 . . ?
C3 C6 C1 120.47(17) . . ?
C3 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C7 N1 122.23(17) . . ?
O1 C7 C2 121.56(17) . . ?
N1 C7 C2 116.19(15) . . ?
O2 C8 N4 123.31(18) . . ?
O2 C8 C1 121.14(17) . . ?
N4 C8 C1 115.55(15) . . ?
O3 C9 N7 123.99(16) . . ?
O3 C9 C3 120.79(15) . . ?
N7 C9 C3 115.22(15) . . ?
N2 C10 C11 121.44(16) . . ?
N2 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C13 C11 C12 117.50(19) . . ?
C13 C11 C10 118.75(16) . . ?
C12 C11 C10 123.75(18) . . ?
C14 C12 C11 118.54(19) . . ?
C14 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C15 C13 C11 118.86(18) . . ?
C15 C13 H13 120.6 . . ?
C11 C13 H13 120.6 . . ?
N3 C14 C12 124.85(19) . . ?
N3 C14 H14 117.6 . . ?
C12 C14 H14 117.6 . . ?
N3 C15 C13 124.3(2) . . ?
N3 C15 H15 117.8 . . ?
C13 C15 H15 117.8 . . ?
N5 C16 C17 121.24(18) . . ?
N5 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C19 C17 C18 117.49(19) . . ?
C19 C17 C16 119.27(18) . . ?
C18 C17 C16 123.24(18) . . ?
C21 C18 C17 118.5(2) . . ?
C21 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C17 C19 C20 119.6(2) . . ?
C17 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
N6 C20 C19 123.5(2) . . ?
N6 C20 H20 118.2 . . ?
C19 C20 H20 118.2 . . ?
N6 C21 C18 124.8(2) . . ?
N6 C21 H21 117.6 . . ?
C18 C21 H21 117.6 . . ?
N8 C22 C23 119.46(16) . . ?
N8 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C25 C23 C24 117.76(16) . . ?
C25 C23 C22 123.23(16) . . ?
C24 C23 C22 119.00(16) . . ?
C27 C24 C23 119.12(18) . . ?
C27 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C26 C25 C23 118.61(17) . . ?
C26 C25 H25 120.7 . . ?
C23 C25 H25 120.7 . . ?
N9 C26 C25 124.12(18) . . ?
N9 C26 H26 117.9 . . ?
C25 C26 H26 117.9 . . ?
N9 C27 C24 123.44(17) . . ?
N9 C27 H27 118.3 . . ?
C24 C27 H27 118.3 . . ?
O4 C28 N10 124.0(2) . . ?
C30 C29 N10 116.2(3) . . ?
N10 C31 C32 111.7(2) . . ?
C7 N1 N2 118.56(14) . . ?
C7 N1 H1 120.7 . . ?
N2 N1 H1 120.7 . . ?
C10 N2 N1 115.10(14) . . ?
C15 N3 C14 115.90(19) . . ?
C8 N4 N5 120.12(15) . . ?
C8 N4 H4A 119.9 . . ?
N5 N4 H4A 119.9 . . ?
C16 N5 N4 114.47(15) . . ?
C20 N6 C21 116.1(2) . . ?
C9 N7 N8 118.06(14) . . ?
C9 N7 H7 121.0 . . ?
N8 N7 H7 121.0 . . ?
C22 N8 N7 115.48(15) . . ?
C27 N9 C26 116.94(16) . . ?
C28 N10 C29 120.41(19) . . ?
C28 N10 C31 120.60(19) . . ?
C29 N10 C31 118.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        23.31
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.074
####################################################################### 
# 
# 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_DMSO
_database_code_depnum_ccdc_archive 'CCDC 1056917'
_audit_update_record             
;
2018-04-12 deposited with the CCDC.
2019-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C33 H21 N9 O8 S'
_chemical_formula_sum            'C33 H21 N9 O8 S'
_chemical_formula_weight         703.65

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'
S S 0.1246 0.1234 '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                   11.9851(17)
_cell_length_b                   12.2632(17)
_cell_length_c                   13.7369(19)
_cell_angle_alpha                94.016(2)
_cell_angle_beta                 112.728(2)
_cell_angle_gamma                103.896(2)
_cell_volume                     1777.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6144
_cell_measurement_theta_min      0.991
_cell_measurement_theta_max      0.994

_exptl_crystal_description       rod
_exptl_crystal_colour            coloress
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             724
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            8773
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0648
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6144
_reflns_number_gt                4760
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL

_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)+(0.1588P)²+1.9052P] where P=(Fo²+2Fc²)/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_number_reflns         6144
_refine_ls_number_parameters     460
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0889
_refine_ls_wR_factor_ref         0.2729
_refine_ls_wR_factor_gt          0.2548
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.81800(14) 0.53120(14) 0.77994(12) 0.0267(4) Uani 1 1 d . . .
C2 C 0.59638(14) 0.50569(13) 0.66911(11) 0.0241(4) Uani 1 1 d . . .
C3 C 0.74724(14) 0.69141(13) 0.71835(12) 0.0271(4) Uani 1 1 d . . .
C4 C 0.84411(14) 0.64771(13) 0.77798(12) 0.0268(4) Uani 1 1 d . . .
H4 H 0.9258 0.6960 0.8163 0.032 Uiso 1 1 calc R . .
C5 C 0.69439(14) 0.46152(13) 0.72641(12) 0.0264(4) Uani 1 1 d . . .
H5 H 0.6766 0.3839 0.7288 0.032 Uiso 1 1 calc R . .
C6 C 0.62416(14) 0.62087(13) 0.66458(12) 0.0267(4) Uani 1 1 d . . .
H6 H 0.5600 0.6512 0.6253 0.032 Uiso 1 1 calc R . .
C7 C 0.91624(15) 0.47136(14) 0.83041(13) 0.0319(5) Uani 1 1 d . . .
C8 C 0.46780(14) 0.42354(13) 0.60843(12) 0.0261(4) Uani 1 1 d . . .
C9 C 0.77836(15) 0.81619(14) 0.71140(13) 0.0301(5) Uani 1 1 d . . .
C10 C 1.23742(15) 0.55394(16) 0.99391(14) 0.0354(5) Uani 1 1 d . . .
H10 H 1.2519 0.6325 0.9990 0.042 Uiso 1 1 calc R . .
C11 C 1.34244(15) 0.50717(17) 1.04836(13) 0.0355(5) Uani 1 1 d . . .
C12 C 1.46351(17) 0.5789(2) 1.10370(15) 0.0447(6) Uani 1 1 d . . .
H12 H 1.4804 0.6573 1.1057 0.054 Uiso 1 1 calc R . .
C13 C 1.32446(17) 0.39111(17) 1.04798(14) 0.0418(6) Uani 1 1 d . . .
H13 H 1.2443 0.3397 1.0111 0.050 Uiso 1 1 calc R . .
C14 C 1.42586(18) 0.3529(2) 1.10245(16) 0.0499(6) Uani 1 1 d . . .
H14 H 1.4118 0.2747 1.1012 0.060 Uiso 1 1 calc R . .
C15 C 1.56004(17) 0.5313(2) 1.15658(16) 0.0549(7) Uani 1 1 d . . .
H15 H 1.6412 0.5807 1.1938 0.066 Uiso 1 1 calc R . .
C16 C 0.16257(15) 0.44257(15) 0.47779(13) 0.0317(5) Uani 1 1 d . . .
H16 H 0.1791 0.5199 0.5023 0.038 Uiso 1 1 calc R . .
C17 C 0.03472(15) 0.37598(16) 0.40312(13) 0.0334(5) Uani 1 1 d . . .
C18 C -0.00139(17) 0.25820(18) 0.37442(17) 0.0445(6) Uani 1 1 d . . .
H18 H 0.0550 0.2170 0.4053 0.053 Uiso 1 1 calc R . .
C19 C -0.05412(16) 0.43145(19) 0.35422(15) 0.0423(6) Uani 1 1 d . . .
H19 H -0.0336 0.5106 0.3708 0.051 Uiso 1 1 calc R . .
C20 C -0.17351(18) 0.3689(2) 0.28053(16) 0.0530(7) Uani 1 1 d . . .
H20 H -0.2321 0.4077 0.2486 0.064 Uiso 1 1 calc R . .
C21 C -0.12321(19) 0.2026(2) 0.29874(19) 0.0589(8) Uani 1 1 d . . .
H21 H -0.1459 0.1237 0.2792 0.071 Uiso 1 1 calc R . .
C22 C 0.65380(18) 0.95641(15) 0.49954(15) 0.0421(6) Uani 1 1 d . . .
H22 H 0.6123 0.8924 0.4451 0.051 Uiso 1 1 calc R . .
C23 C 0.64807(17) 1.07019(14) 0.47568(14) 0.0345(5) Uani 1 1 d . . .
C24 C 0.70266(19) 1.16669(16) 0.55536(14) 0.0432(6) Uani 1 1 d . . .
H24 H 0.7449 1.1612 0.6268 0.052 Uiso 1 1 calc R . .
C25 C 0.58672(18) 1.08437(16) 0.37090(15) 0.0414(6) Uani 1 1 d . . .
H25 H 0.5499 1.0221 0.3148 0.050 Uiso 1 1 calc R . .
C26 C 0.69348(19) 1.27046(15) 0.52751(14) 0.0413(6) Uani 1 1 d . . .
H26 H 0.7313 1.3344 0.5820 0.050 Uiso 1 1 calc R . .
C27 C 0.58091(17) 1.19237(15) 0.35065(14) 0.0367(5) Uani 1 1 d . . .
H27 H 0.5380 1.2002 0.2801 0.044 Uiso 1 1 calc R . .
C28 C 0.2583(2) 0.8838(2) 0.15265(18) 0.0582(8) Uani 1 1 d . . .
C29 C 0.1731(4) 0.9953(2) -0.0103(2) 0.0955(13) Uani 1 1 d . . .
C30 C 0.83715(19) 0.80447(18) 0.2390(2) 0.0548(7) Uani 1 1 d . . .
C31 C 0.9787(4) 0.7702(4) 0.3319(3) 0.1250(17) Uani 1 1 d . . .
C32 C 0.9769(8) 0.9096(9) 0.3971(7) 0.257(5) Uani 1 1 d . . .
C33 C 0.8631(2) 0.8335(3) 0.3101(3) 0.0833(11) Uani 1 1 d . . .
N1 N 1.03336(12) 0.53840(12) 0.89501(11) 0.0296(4) Uani 1 1 d . . .
H1 H 1.0490 0.6114 0.9078 0.036 Uiso 1 1 calc R . .
N2 N 1.12757(13) 0.48768(12) 0.94023(11) 0.0334(4) Uani 1 1 d . . .
N3 N 1.54484(15) 0.42178(18) 1.15773(14) 0.0560(6) Uani 1 1 d . . .
N4 N 0.36950(12) 0.46868(12) 0.57522(10) 0.0280(4) Uani 1 1 d . . .
H4A H 0.3804 0.5401 0.5944 0.034 Uiso 1 1 calc R . .
N5 N 0.25145(12) 0.39625(12) 0.50972(11) 0.0291(4) Uani 1 1 d . . .
N6 N -0.20883(15) 0.25555(18) 0.25289(14) 0.0558(6) Uani 1 1 d . . .
N7 N 0.71225(14) 0.83623(11) 0.61193(12) 0.0364(5) Uani 1 1 d . . .
H7 H 0.6679 0.7801 0.5591 0.044 Uiso 1 1 calc R . .
N8 N 0.71668(14) 0.94606(12) 0.59639(12) 0.0351(4) Uani 1 1 d . . .
N9 N 0.63339(13) 1.28578(12) 0.42668(11) 0.0348(4) Uani 1 1 d . . .
O1 O 0.88884(12) 0.36748(11) 0.80974(13) 0.0550(5) Uani 1 1 d . . .
O2 O 0.45379(11) 0.32074(10) 0.58799(10) 0.0352(4) Uani 1 1 d . . .
O3 O 0.85426(12) 0.89052(10) 0.78692(10) 0.0431(4) Uani 1 1 d . . .
O4 O 0.13231(13) 0.77537(12) -0.04705(11) 0.0496(5) Uani 1 1 d . . .
O5 O 0.9582(5) 0.8197(6) 0.2090(5) 0.274(3) Uani 1 1 d . . .
O6 O 0.7889(3) 0.9015(4) 0.2402(4) 0.198(2) Uani 1 1 d . . .
O7 O 0.54175(19) 0.89788(18) 0.12064(16) 0.0839(7) Uani 1 1 d . . .
O8 O 0.54647(15) 0.12182(15) 0.10256(14) 0.0684(6) Uani 1 1 d . . .
S1 S 0.12640(5) 0.86677(5) 0.02792(4) 0.05010(16) Uani 1 1 d . . .


_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 C5 1.388(2) . ?
C1 C4 1.392(2) . ?
C1 C7 1.504(2) . ?
C2 C6 1.383(2) . ?
C2 C5 1.394(2) . ?
C2 C8 1.4928(19) . ?
C3 C6 1.388(2) . ?
C3 C4 1.390(2) . ?
C3 C9 1.505(2) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.220(2) . ?
C7 N1 1.3471(18) . ?
C8 O2 1.228(2) . ?
C8 N4 1.355(2) . ?
C9 O3 1.2144(18) . ?
C9 N7 1.364(2) . ?
C10 N2 1.2607(19) . ?
C10 C11 1.467(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(2) . ?
C11 C13 1.387(3) . ?
C12 C15 1.394(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(3) . ?
C13 H13 0.9300 . ?
C14 N3 1.349(2) . ?
C14 H14 0.9300 . ?
C15 N3 1.313(3) . ?
C15 H15 0.9300 . ?
C16 N5 1.271(2) . ?
C16 C17 1.461(2) . ?
C16 H16 0.9300 . ?
C17 C19 1.381(3) . ?
C17 C18 1.385(3) . ?
C18 C21 1.388(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(2) . ?
C19 H19 0.9300 . ?
C20 N6 1.332(3) . ?
C20 H20 0.9300 . ?
C21 N6 1.322(3) . ?
C21 H21 0.9300 . ?
C22 N8 1.284(2) . ?
C22 C23 1.467(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.386(2) . ?
C23 C25 1.386(3) . ?
C24 C26 1.371(3) . ?
C24 H24 0.9300 . ?
C25 C27 1.385(3) . ?
C25 H25 0.9300 . ?
C26 N9 1.343(2) . ?
C26 H26 0.9300 . ?
C27 N9 1.333(2) . ?
C27 H27 0.9300 . ?
C28 S1 1.782(2) . ?
C29 S1 1.730(3) . ?
C30 C31 1.852(5) . ?
C31 O5 1.782(8) . ?
C32 C33 1.460(8) . ?
C33 O6 1.489(5) . ?
N1 N2 1.377(2) . ?
N1 H1 0.8600 . ?
N4 N5 1.3788(16) . ?
N4 H4A 0.8600 . ?
N7 N8 1.370(2) . ?
N7 H7 0.8600 . ?
O4 S1 1.5016(17) . ?

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
C5 C1 C4 119.33(15) . . ?
C5 C1 C7 115.89(14) . . ?
C4 C1 C7 124.65(13) . . ?
C6 C2 C5 118.89(13) . . ?
C6 C2 C8 123.27(14) . . ?
C5 C2 C8 117.66(14) . . ?
C6 C3 C4 120.63(15) . . ?
C6 C3 C9 120.46(14) . . ?
C4 C3 C9 118.90(13) . . ?
C3 C4 C1 119.50(13) . . ?
C3 C4 H4 120.2 . . ?
C1 C4 H4 120.2 . . ?
C1 C5 C2 121.26(15) . . ?
C1 C5 H5 119.4 . . ?
C2 C5 H5 119.4 . . ?
C2 C6 C3 120.31(15) . . ?
C2 C6 H6 119.8 . . ?
C3 C6 H6 119.8 . . ?
O1 C7 N1 123.38(17) . . ?
O1 C7 C1 120.04(13) . . ?
N1 C7 C1 116.55(14) . . ?
O2 C8 N4 122.45(13) . . ?
O2 C8 C2 120.87(15) . . ?
N4 C8 C2 116.65(14) . . ?
O3 C9 N7 124.06(16) . . ?
O3 C9 C3 123.11(15) . . ?
N7 C9 C3 112.83(12) . . ?
N2 C10 C11 120.06(17) . . ?
N2 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C13 117.59(18) . . ?
C12 C11 C10 120.30(19) . . ?
C13 C11 C10 122.10(15) . . ?
C11 C12 C15 118.5(2) . . ?
C11 C12 H12 120.8 . . ?
C15 C12 H12 120.8 . . ?
C14 C13 C11 119.38(16) . . ?
C14 C13 H13 120.3 . . ?
C11 C13 H13 120.3 . . ?
N3 C14 C13 123.9(2) . . ?
N3 C14 H14 118.0 . . ?
C13 C14 H14 118.0 . . ?
N3 C15 C12 124.86(18) . . ?
N3 C15 H15 117.6 . . ?
C12 C15 H15 117.6 . . ?
N5 C16 C17 120.87(16) . . ?
N5 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C19 C17 C18 117.37(15) . . ?
C19 C17 C16 119.63(17) . . ?
C18 C17 C16 122.93(17) . . ?
C17 C18 C21 118.9(2) . . ?
C17 C18 H18 120.6 . . ?
C21 C18 H18 120.6 . . ?
C20 C19 C17 119.7(2) . . ?
C20 C19 H19 120.2 . . ?
C17 C19 H19 120.2 . . ?
N6 C20 C19 123.2(2) . . ?
N6 C20 H20 118.4 . . ?
C19 C20 H20 118.4 . . ?
N6 C21 C18 123.8(2) . . ?
N6 C21 H21 118.1 . . ?
C18 C21 H21 118.1 . . ?
N8 C22 C23 119.30(15) . . ?
N8 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C24 C23 C25 117.55(17) . . ?
C24 C23 C22 122.09(16) . . ?
C25 C23 C22 120.36(15) . . ?
C26 C24 C23 119.09(16) . . ?
C26 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C27 C25 C23 119.25(16) . . ?
C27 C25 H25 120.4 . . ?
C23 C25 H25 120.4 . . ?
N9 C26 C24 124.25(16) . . ?
N9 C26 H26 117.9 . . ?
C24 C26 H26 117.9 . . ?
N9 C27 C25 123.66(16) . . ?
N9 C27 H27 118.2 . . ?
C25 C27 H27 118.2 . . ?
O5 C31 C30 53.2(2) . . ?
C32 C33 O6 110.1(5) . . ?
C7 N1 N2 118.68(14) . . ?
C7 N1 H1 120.7 . . ?
N2 N1 H1 120.7 . . ?
C10 N2 N1 116.50(15) . . ?
C15 N3 C14 115.79(19) . . ?
C8 N4 N5 117.76(13) . . ?
C8 N4 H4A 121.1 . . ?
N5 N4 H4A 121.1 . . ?
C16 N5 N4 115.76(14) . . ?
C21 N6 C20 117.10(16) . . ?
C9 N7 N8 119.82(13) . . ?
C9 N7 H7 120.1 . . ?
N8 N7 H7 120.1 . . ?
C22 N8 N7 115.21(14) . . ?
C27 N9 C26 116.19(16) . . ?
O4 S1 C29 106.84(15) . . ?
O4 S1 C28 105.90(11) . . ?
C29 S1 C28 100.15(13) . . ?

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
N4 H4A N9 0.86 2.21 3.022(2) 157.0 2_676
N7 H7 O2 0.86 2.06 2.8990(17) 164.8 2_666

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         1.252
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.095
####################################################################### 
# 
# 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_DMF
_database_code_depnum_ccdc_archive 'CCDC 1056916'
_audit_update_record             
;
2018-04-12 deposited with the CCDC.
2019-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C27 H21 N9 O7'
_chemical_formula_sum            'C27 H21 N9 O7'
_chemical_formula_weight         583.53

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                   7.4872(6)
_cell_length_b                   12.4001(10)
_cell_length_c                   17.0797(13)
_cell_angle_alpha                109.166(2)
_cell_angle_beta                 99.619(2)
_cell_angle_gamma                93.273(2)
_cell_volume                     1466.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5692
_cell_measurement_theta_min      0.994
_cell_measurement_theta_max      0.997

_exptl_crystal_description       rod
_exptl_crystal_colour            coloress
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             604
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.994
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            8084
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_sigmaI/netI    0.0929
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         26.07
_reflns_number_total             5692
_reflns_number_gt                3328
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL

_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/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_number_reflns         5692
_refine_ls_number_parameters     406
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.2061
_refine_ls_wR_factor_gt          0.1759
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.004
_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 0.74504(19) 0.35812(11) 0.79998(8) 0.0227(4) Uani 1 1 d . . .
C2 C 0.72456(18) 0.43463(11) 0.94792(8) 0.0214(4) Uani 1 1 d . . .
C3 C 0.57068(19) 0.24644(11) 0.85914(8) 0.0223(4) Uani 1 1 d . . .
C4 C 0.63966(19) 0.25782(12) 0.79110(8) 0.0234(4) Uani 1 1 d . . .
H4 H 0.6149 0.1978 0.7395 0.028 Uiso 1 1 calc R . .
C5 C 0.78571(18) 0.44662(12) 0.87753(8) 0.0235(4) Uani 1 1 d . . .
H5 H 0.8542 0.5146 0.8829 0.028 Uiso 1 1 calc R . .
C6 C 0.61416(19) 0.33482(11) 0.93860(8) 0.0236(4) Uani 1 1 d . . .
H6 H 0.5698 0.3268 0.9844 0.028 Uiso 1 1 calc R . .
C7 C 0.8050(2) 0.38331(12) 0.72807(8) 0.0262(4) Uani 1 1 d . . .
C8 C 0.76399(19) 0.53799(12) 1.02808(8) 0.0237(4) Uani 1 1 d . . .
C9 C 0.4425(2) 0.14089(12) 0.84189(8) 0.0259(4) Uani 1 1 d . . .
C10 C 0.7824(2) 0.23070(13) 0.51536(8) 0.0299(4) Uani 1 1 d . . .
H10 H 0.7403 0.1580 0.5141 0.036 Uiso 1 1 calc R . .
C11 C 0.8063(2) 0.24948(12) 0.43683(8) 0.0266(4) Uani 1 1 d . . .
C12 C 0.9014(3) 0.34907(14) 0.43710(9) 0.0410(5) Uani 1 1 d . . .
H12 H 0.9618 0.4037 0.4879 0.049 Uiso 1 1 calc R . .
C13 C 0.7301(2) 0.16883(13) 0.35816(9) 0.0327(5) Uani 1 1 d . . .
H13 H 0.6708 0.0988 0.3543 0.039 Uiso 1 1 calc R . .
C14 C 0.7423(2) 0.19253(13) 0.28643(9) 0.0340(5) Uani 1 1 d . . .
H14 H 0.6878 0.1377 0.2346 0.041 Uiso 1 1 calc R . .
C15 C 0.9062(2) 0.36689(14) 0.36189(9) 0.0396(5) Uani 1 1 d . . .
H15 H 0.9667 0.4356 0.3639 0.048 Uiso 1 1 calc R . .
C16 C 0.0489(2) 0.08210(12) 0.91026(8) 0.0281(4) Uani 1 1 d . . .
H16 H 0.0313 0.1577 0.9383 0.034 Uiso 1 1 calc R . .
C17 C -0.0863(2) -0.01321(12) 0.90238(8) 0.0278(4) Uani 1 1 d . . .
C18 C -0.2501(2) 0.00939(13) 0.92821(9) 0.0326(5) Uani 1 1 d . . .
H18 H -0.2726 0.0850 0.9524 0.039 Uiso 1 1 calc R . .
C19 C -0.0591(2) -0.12793(13) 0.86947(9) 0.0357(5) Uani 1 1 d . . .
H19 H 0.0501 -0.1472 0.8525 0.043 Uiso 1 1 calc R . .
C20 C -0.3803(2) -0.08058(14) 0.91800(10) 0.0373(5) Uani 1 1 d . . .
H20 H -0.4907 -0.0636 0.9345 0.045 Uiso 1 1 calc R . .
C21 C -0.1934(2) -0.21312(14) 0.86188(10) 0.0415(5) Uani 1 1 d . . .
H21 H -0.1724 -0.2894 0.8395 0.050 Uiso 1 1 calc R . .
C22 C 0.7329(2) 0.59584(13) 1.23819(9) 0.0298(4) Uani 1 1 d . . .
H22 H 0.7002 0.5211 1.2357 0.036 Uiso 1 1 calc R . .
C23 C 0.7476(2) 0.69218(13) 1.31732(8) 0.0291(4) Uani 1 1 d . . .
C24 C 0.8132(2) 0.80366(13) 1.32714(9) 0.0334(5) Uani 1 1 d . . .
H24 H 0.8512 0.8197 1.2826 0.040 Uiso 1 1 calc R . .
C25 C 0.6924(2) 0.67410(15) 1.38493(9) 0.0425(5) Uani 1 1 d . . .
H25 H 0.6488 0.6003 1.3809 0.051 Uiso 1 1 calc R . .
C26 C 0.7012(3) 0.76570(17) 1.45954(10) 0.0503(6) Uani 1 1 d . . .
H26 H 0.6622 0.7512 1.5044 0.060 Uiso 1 1 calc R . .
C27 C 0.8216(2) 0.89029(15) 1.40291(9) 0.0429(5) Uani 1 1 d . . .
H27 H 0.8697 0.9640 1.4089 0.052 Uiso 1 1 calc R . .
N1 N 0.78680(17) 0.29186(10) 0.65424(7) 0.0267(3) Uani 1 1 d . . .
H1 H 0.7559 0.2229 0.6520 0.032 Uiso 1 1 calc R . .
N2 N 0.81937(17) 0.31390(10) 0.58441(7) 0.0271(4) Uani 1 1 d . . .
N3 N 0.82857(18) 0.29068(11) 0.28649(7) 0.0328(4) Uani 1 1 d . . .
N4 N 0.74558(16) 0.52009(10) 1.09969(6) 0.0241(3) Uani 1 1 d . . .
H4A H 0.7221 0.4518 1.1006 0.029 Uiso 1 1 calc R . .
N5 N 0.76573(16) 0.61510(10) 1.17172(7) 0.0260(4) Uani 1 1 d . . .
N6 N 0.7628(2) 0.87326(13) 1.46976(8) 0.0472(5) Uani 1 1 d . . .
N7 N 0.31130(17) 0.15487(10) 0.88935(7) 0.0291(4) Uani 1 1 d . . .
H7 H 0.3040 0.2210 0.9254 0.035 Uiso 1 1 calc R . .
N8 N 0.19005(17) 0.06058(10) 0.87843(7) 0.0289(4) Uani 1 1 d . . .
N9 N -0.35405(19) -0.19077(11) 0.88549(8) 0.0402(4) Uani 1 1 d . . .
O1 O 0.86039(17) 0.48042(9) 0.73395(6) 0.0406(3) Uani 1 1 d . . .
O2 O 0.80633(15) 0.63312(8) 1.02409(6) 0.0334(3) Uani 1 1 d . . .
O3 O 0.45759(15) 0.05023(8) 0.78794(6) 0.0350(3) Uani 1 1 d . . .
O4 O 0.68881(15) 0.31340(9) 0.12850(6) 0.0378(3) Uani 1 1 d . A 1
O5 O 0.26178(18) -0.04150(9) 0.37586(6) 0.0458(4) Uani 1 1 d . B 2
O6 O 0.1944(3) 0.01170(16) 0.31498(11) 0.0303(6) Uani 0.50 1 d P C 3
O7 O 0.3850(4) 0.3731(2) 0.36181(16) 0.0606(8) Uani 0.50 1 d P D 4
O8 O 0.3467(4) 0.4683(2) 0.41476(17) 0.0684(10) Uani 0.50 1 d P E 5
O9 O 0.3878(8) 0.4069(5) 0.4504(3) 0.169(2) Uani 0.50 1 d PU F 6


_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 C4 1.384(2) . ?
C1 C5 1.3871(16) . ?
C1 C7 1.493(2) . ?
C2 C6 1.397(2) . ?
C2 C5 1.404(2) . ?
C2 C8 1.5079(17) . ?
C3 C4 1.392(2) . ?
C3 C6 1.4085(16) . ?
C3 C9 1.493(2) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.2172(18) . ?
C7 N1 1.3714(16) . ?
C8 O2 1.2304(18) . ?
C8 N4 1.3400(19) . ?
C9 O3 1.2227(16) . ?
C9 N7 1.358(2) . ?
C10 N2 1.2614(16) . ?
C10 C11 1.472(2) . ?
C10 H10 0.9300 . ?
C11 C13 1.3883(17) . ?
C11 C12 1.388(2) . ?
C12 C15 1.379(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.366(2) . ?
C13 H13 0.9300 . ?
C14 N3 1.345(2) . ?
C14 H14 0.9300 . ?
C15 N3 1.3331(17) . ?
C15 H15 0.9300 . ?
C16 N8 1.270(2) . ?
C16 C17 1.467(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(2) . ?
C17 C19 1.388(2) . ?
C18 C20 1.385(2) . ?
C18 H18 0.9300 . ?
C19 C21 1.374(2) . ?
C19 H19 0.9300 . ?
C20 N9 1.335(2) . ?
C20 H20 0.9300 . ?
C21 N9 1.347(2) . ?
C21 H21 0.9300 . ?
C22 N5 1.293(2) . ?
C22 C23 1.4631(18) . ?
C22 H22 0.9300 . ?
C23 C25 1.369(2) . ?
C23 C24 1.387(2) . ?
C24 C27 1.373(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.390(2) . ?
C25 H25 0.9300 . ?
C26 N6 1.331(3) . ?
C26 H26 0.9300 . ?
C27 N6 1.363(2) . ?
C27 H27 0.9300 . ?
N1 N2 1.3640(18) . ?
N1 H1 0.8600 . ?
N4 N5 1.3748(14) . ?
N4 H4A 0.8600 . ?
N7 N8 1.3803(17) . ?
N7 H7 0.8600 . ?

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
C4 C1 C5 119.89(14) . . ?
C4 C1 C7 123.72(11) . . ?
C5 C1 C7 116.11(13) . . ?
C6 C2 C5 119.53(11) . . ?
C6 C2 C8 123.00(13) . . ?
C5 C2 C8 117.05(12) . . ?
C4 C3 C6 120.27(13) . . ?
C4 C3 C9 116.84(11) . . ?
C6 C3 C9 122.80(13) . . ?
C1 C4 C3 120.27(11) . . ?
C1 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C1 C5 C2 120.65(13) . . ?
C1 C5 H5 119.7 . . ?
C2 C5 H5 119.7 . . ?
C2 C6 C3 119.28(14) . . ?
C2 C6 H6 120.4 . . ?
C3 C6 H6 120.4 . . ?
O1 C7 N1 122.09(14) . . ?
O1 C7 C1 121.66(12) . . ?
N1 C7 C1 116.19(13) . . ?
O2 C8 N4 123.94(11) . . ?
O2 C8 C2 118.97(13) . . ?
N4 C8 C2 117.07(13) . . ?
O3 C9 N7 124.15(14) . . ?
O3 C9 C3 120.77(14) . . ?
N7 C9 C3 115.08(11) . . ?
N2 C10 C11 119.55(14) . . ?
N2 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C13 C11 C12 116.51(14) . . ?
C13 C11 C10 121.23(14) . . ?
C12 C11 C10 122.24(12) . . ?
C15 C12 C11 119.91(13) . . ?
C15 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C11 119.91(15) . . ?
C14 C13 H13 120.0 . . ?
C11 C13 H13 120.0 . . ?
N3 C14 C13 123.73(12) . . ?
N3 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
N3 C15 C12 123.39(16) . . ?
N3 C15 H15 118.3 . . ?
C12 C15 H15 118.3 . . ?
N8 C16 C17 119.45(13) . . ?
N8 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C19 116.97(14) . . ?
C18 C17 C16 119.97(13) . . ?
C19 C17 C16 123.06(15) . . ?
C17 C18 C20 119.97(14) . . ?
C17 C18 H18 120.0 . . ?
C20 C18 H18 120.0 . . ?
C21 C19 C17 120.08(16) . . ?
C21 C19 H19 120.0 . . ?
C17 C19 H19 120.0 . . ?
N9 C20 C18 122.73(16) . . ?
N9 C20 H20 118.6 . . ?
C18 C20 H20 118.6 . . ?
N9 C21 C19 122.74(15) . . ?
N9 C21 H21 118.6 . . ?
C19 C21 H21 118.6 . . ?
N5 C22 C23 119.66(14) . . ?
N5 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C25 C23 C24 117.46(13) . . ?
C25 C23 C22 119.82(15) . . ?
C24 C23 C22 122.72(15) . . ?
C27 C24 C23 119.71(16) . . ?
C27 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C23 C25 C26 120.16(18) . . ?
C23 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
N6 C26 C25 123.07(18) . . ?
N6 C26 H26 118.5 . . ?
C25 C26 H26 118.5 . . ?
N6 C27 C24 123.06(17) . . ?
N6 C27 H27 118.5 . . ?
C24 C27 H27 118.5 . . ?
N2 N1 C7 117.79(12) . . ?
N2 N1 H1 121.1 . . ?
C7 N1 H1 121.1 . . ?
C10 N2 N1 116.61(13) . . ?
C15 N3 C14 116.43(14) . . ?
C8 N4 N5 117.40(12) . . ?
C8 N4 H4A 121.3 . . ?
N5 N4 H4A 121.3 . . ?
C22 N5 N4 115.90(12) . . ?
C26 N6 C27 116.50(14) . . ?
C9 N7 N8 118.53(11) . . ?
C9 N7 H7 120.7 . . ?
N8 N7 H7 120.7 . . ?
C16 N8 N7 115.84(12) . . ?
C20 N9 C21 117.47(15) . . ?

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
N7 H7 O2 0.86 2.02 2.8320(16) 157.0 2_667

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        26.07
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.086
