# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_100429t
_database_code_depnum_ccdc_archive 'CCDC 1025189'
_audit_update_record             
;
2014-09-19 deposited with the CCDC.
2014-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
  ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H21 N9'
_chemical_formula_weight         327.41

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.429(5)
_cell_length_b                   15.689(9)
_cell_length_c                   13.238(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.668(13)
_cell_angle_gamma                90.00
_cell_volume                     1714.5(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9916
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
  ?
;

_diffrn_ambient_temperature      223(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13278
_diffrn_reflns_av_R_equivalents  0.1480
_diffrn_reflns_av_sigmaI/netI    0.1278
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3002
_reflns_number_gt                1419
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0864P)²+2.0268P] 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     SHELXL
_refine_ls_extinction_coef       0.119(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3002
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1880
_refine_ls_R_factor_gt           0.0986
_refine_ls_wR_factor_ref         0.2671
_refine_ls_wR_factor_gt          0.2218
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_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
N5 N -0.0035(7) 0.4021(3) 0.3814(5) 0.0612(15) Uani 1 1 d . . .
C11 C 0.4177(7) 0.0697(4) 0.2897(4) 0.0512(15) Uani 1 1 d . . .
H11A H 0.3256 0.0318 0.2653 0.061 Uiso 1 1 calc R . .
H11B H 0.4562 0.0906 0.2291 0.061 Uiso 1 1 calc R . .
C5 C 0.4402(6) 0.2232(3) 0.3471(3) 0.0379(13) Uani 1 1 d . . .
C2 C 0.1820(6) 0.2069(3) 0.4499(4) 0.0389(13) Uani 1 1 d . . .
C3 C 0.2630(6) 0.2847(3) 0.4498(4) 0.0396(13) Uani 1 1 d . . .
C9 C 0.4747(7) 0.3788(3) 0.3965(4) 0.0471(15) Uani 1 1 d . . .
H9A H 0.3967 0.4246 0.3996 0.057 Uiso 1 1 calc R . .
H9B H 0.5123 0.3849 0.3315 0.057 Uiso 1 1 calc R . .
N8 N 0.6004(6) 0.2934(3) 0.1376(4) 0.0524(13) Uani 1 1 d . . .
N1 N -0.0057(8) 0.0449(4) 0.3216(7) 0.105(2) Uani 1 1 d . . .
C7 C 0.0448(7) 0.1964(4) 0.5078(5) 0.0555(16) Uani 1 1 d . . .
H7A H -0.0297 0.1524 0.4736 0.067 Uiso 1 1 calc R . .
H7B H -0.0157 0.2500 0.5044 0.067 Uiso 1 1 calc R . .
C1 C 0.2345(6) 0.1368(3) 0.3987(4) 0.0409(13) Uani 1 1 d . . .
C4 C 0.3894(6) 0.2933(3) 0.3968(3) 0.0361(13) Uani 1 1 d . . .
N2 N -0.0342(7) 0.0954(5) 0.2535(6) 0.0714(17) Uani 1 1 d . . .
C13 C 0.1470(7) 0.0522(4) 0.3991(5) 0.0585(17) Uani 1 1 d . . .
H13A H 0.2201 0.0064 0.3871 0.070 Uiso 1 1 calc R . .
H13B H 0.1230 0.0434 0.4677 0.070 Uiso 1 1 calc R . .
N9 N 0.6665(8) 0.3289(4) 0.0855(4) 0.0839(19) Uani 1 1 d . . .
C15 C 0.5792(6) 0.2319(4) 0.2920(4) 0.0487(15) Uani 1 1 d . . .
H15A H 0.6528 0.2771 0.3241 0.058 Uiso 1 1 calc R . .
H15B H 0.6402 0.1784 0.2966 0.058 Uiso 1 1 calc R . .
N6 N -0.1161(8) 0.3886(5) 0.3228(5) 0.096(2) Uani 1 1 d . . .
C10 C 0.6190(7) 0.3892(4) 0.4863(4) 0.0609(17) Uani 1 1 d . . .
H10A H 0.6677 0.4448 0.4823 0.091 Uiso 1 1 calc R . .
H10B H 0.6984 0.3452 0.4826 0.091 Uiso 1 1 calc R . .
H10C H 0.5824 0.3843 0.5510 0.091 Uiso 1 1 calc R . .
C14 C 0.2152(7) 0.3598(4) 0.5070(5) 0.0573(16) Uani 1 1 d . . .
H14A H 0.1523 0.3394 0.5568 0.069 Uiso 1 1 calc R . .
H14B H 0.3135 0.3869 0.5459 0.069 Uiso 1 1 calc R . .
N3 N -0.0758(10) 0.1415(7) 0.1905(7) 0.143(4) Uani 1 1 d . . .
N7 N 0.5132(6) 0.2532(4) 0.1824(4) 0.0770(18) Uani 1 1 d . . .
N4 N 0.1181(7) 0.4251(3) 0.4398(6) 0.092(2) Uani 1 1 d . . .
C8 C 0.1036(8) 0.1718(4) 0.6203(5) 0.073(2) Uani 1 1 d . . .
H8A H 0.0114 0.1656 0.6532 0.110 Uiso 1 1 calc R . .
H8B H 0.1749 0.2160 0.6552 0.110 Uiso 1 1 calc R . .
H8C H 0.1621 0.1183 0.6242 0.110 Uiso 1 1 calc R . .
C6 C 0.3606(6) 0.1450(3) 0.3451(4) 0.0381(13) Uani 1 1 d . . .
C12 C 0.5522(7) 0.0193(4) 0.3573(5) 0.0666(18) Uani 1 1 d . . .
H12A H 0.5840 -0.0276 0.3180 0.100 Uiso 1 1 calc R . .
H12B H 0.5139 -0.0030 0.4164 0.100 Uiso 1 1 calc R . .
H12C H 0.6446 0.0562 0.3808 0.100 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
N5 N6 1.118(7) . ?
N5 N4 1.208(8) . ?
C11 C12 1.518(8) . ?
C11 C6 1.519(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C5 C4 1.393(7) . ?
C5 C6 1.395(7) . ?
C5 C15 1.507(7) . ?
C2 C3 1.399(7) . ?
C2 C1 1.409(7) . ?
C2 C7 1.521(7) . ?
C3 C4 1.396(7) . ?
C3 C14 1.499(7) . ?
C9 C4 1.522(7) . ?
C9 C10 1.528(7) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
N8 N9 1.119(7) . ?
N8 N7 1.211(7) . ?
N1 N2 1.189(8) . ?
N1 C13 1.479(8) . ?
C7 C8 1.521(8) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C1 C6 1.397(7) . ?
C1 C13 1.519(7) . ?
N2 N3 1.105(9) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C15 N7 1.484(7) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C14 N4 1.488(8) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?

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
N6 N5 N4 173.0(7) . . ?
C12 C11 C6 113.1(4) . . ?
C12 C11 H11A 109.0 . . ?
C6 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C6 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C4 C5 C6 120.7(5) . . ?
C4 C5 C15 120.0(5) . . ?
C6 C5 C15 119.3(5) . . ?
C3 C2 C1 118.7(5) . . ?
C3 C2 C7 121.1(5) . . ?
C1 C2 C7 120.2(5) . . ?
C4 C3 C2 120.5(5) . . ?
C4 C3 C14 119.3(5) . . ?
C2 C3 C14 120.3(5) . . ?
C4 C9 C10 113.2(4) . . ?
C4 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C4 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
N9 N8 N7 171.3(6) . . ?
N2 N1 C13 119.2(6) . . ?
C2 C7 C8 113.0(5) . . ?
C2 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C2 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C6 C1 C2 121.1(5) . . ?
C6 C1 C13 120.1(5) . . ?
C2 C1 C13 118.7(5) . . ?
C5 C4 C3 120.0(5) . . ?
C5 C4 C9 120.3(5) . . ?
C3 C4 C9 119.7(5) . . ?
N3 N2 N1 173.3(8) . . ?
N1 C13 C1 114.9(5) . . ?
N1 C13 H13A 108.5 . . ?
C1 C13 H13A 108.5 . . ?
N1 C13 H13B 108.5 . . ?
C1 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
N7 C15 C5 108.6(4) . . ?
N7 C15 H15A 110.0 . . ?
C5 C15 H15A 110.0 . . ?
N7 C15 H15B 110.0 . . ?
C5 C15 H15B 110.0 . . ?
H15A C15 H15B 108.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C14 C3 114.3(5) . . ?
N4 C14 H14A 108.7 . . ?
C3 C14 H14A 108.7 . . ?
N4 C14 H14B 108.7 . . ?
C3 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
N8 N7 C15 116.8(5) . . ?
N5 N4 C14 118.0(5) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C6 C1 118.9(5) . . ?
C5 C6 C11 119.6(5) . . ?
C1 C6 C11 121.4(5) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.083

#-- 


