# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_60928work1p31c
_database_code_depnum_ccdc_archive 'CCDC 1522062'
_audit_update_record             
;
2017-01-09 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H14 N6, 3(C5 H11 N O)'
_chemical_formula_sum            'C38 H47 N9 O3'
_chemical_formula_weight         677.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   P3(1)c

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

_cell_length_a                   18.5004(4)
_cell_length_b                   18.5004(4)
_cell_length_c                   9.6325(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2855.17(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    3497
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      68.32

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          10.2
_exptl_crystal_size_mid          2.2
_exptl_crystal_size_min          2.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.788
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             724
_exptl_absorpt_coefficient_mu    0.414
_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      170(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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 ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27233
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         68.32
_reflns_number_total             3479
_reflns_number_gt                3316
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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. 
;
# SQUEEZE RESULTS
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.014 1192 361 ' '
_platon_squeeze_details          
;
;

_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)+(0.1427P)²+0.1480P] 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_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_number_reflns         3479
_refine_ls_number_parameters     152
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1790
_refine_ls_wR_factor_gt          0.1758
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.122
_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 0.3333 0.6667 0.8460(3) 0.0289(6) Uani 1 3 d S . .
H1 H 0.3333 0.6667 0.9498 0.035 Uiso 1 3 calc SR . .
C2 C 0.3333 0.6667 0.5760(3) 0.0291(6) Uani 1 3 d S . .
H2 H 0.3333 0.6667 0.4722 0.035 Uiso 1 3 calc SR . .
C3 C 0.24966(11) 0.60234(10) 0.78619(17) 0.0275(4) Uani 1 1 d . . .
C4 C 0.18047(12) 0.54767(12) 0.86058(18) 0.0332(4) Uani 1 1 d . . .
H4 H 0.1804 0.5473 0.9592 0.040 Uiso 1 1 calc R . .
C5 C 0.11007(12) 0.49256(13) 0.7840(2) 0.0361(4) Uani 1 1 d . . .
C6 C -0.01076(13) 0.39728(15) 0.7114(3) 0.0470(5) Uani 1 1 d . . .
H6 H -0.0672 0.3532 0.7115 0.056 Uiso 1 1 calc R . .
C7 C 0.24996(11) 0.60246(10) 0.63791(17) 0.0279(4) Uani 1 1 d . . .
C8 C 0.17980(12) 0.54741(11) 0.56200(18) 0.0320(4) Uani 1 1 d . . .
H8 H 0.1795 0.5474 0.4634 0.038 Uiso 1 1 calc R . .
C9 C 0.11001(13) 0.49227(13) 0.6389(2) 0.0368(4) Uani 1 1 d . . .
C11 C 0.71946(14) 0.24088(14) 0.7122(3) 0.0504(5) Uani 1 1 d . . .
H11 H 0.6704 0.2452 0.7087 0.060 Uiso 1 1 calc R . .
C12 C 0.6214(4) 0.0939(3) 0.7198(11) 0.170(3) Uani 1 1 d DU . .
H12A H 0.6059 0.0744 0.8167 0.204 Uiso 1 1 calc R . .
H12B H 0.5823 0.1117 0.6854 0.204 Uiso 1 1 calc R . .
C13 C 0.7573(8) 0.1464(9) 0.9891(16) 0.268(7) Uani 1 1 d DU . .
H13A H 0.8094 0.1488 1.0176 0.401 Uiso 1 1 calc R . .
H13B H 0.7102 0.0903 1.0066 0.401 Uiso 1 1 calc R . .
H13C H 0.7498 0.1873 1.0423 0.401 Uiso 1 1 calc R . .
C14 C 0.7615(10) 0.1669(12) 0.8294(15) 0.270(8) Uani 1 1 d DU . .
H14A H 0.8088 0.2249 0.8257 0.323 Uiso 1 1 calc R . .
H14B H 0.7838 0.1326 0.7899 0.323 Uiso 1 1 calc R . .
C15 C 0.6138(7) 0.0244(7) 0.6330(14) 0.253(6) Uani 1 1 d DU . .
H15A H 0.5562 -0.0221 0.6364 0.380 Uiso 1 1 calc R . .
H15B H 0.6516 0.0059 0.6683 0.380 Uiso 1 1 calc R . .
H15C H 0.6287 0.0435 0.5369 0.380 Uiso 1 1 calc R . .
N1 N 0.03148(11) 0.43032(12) 0.8260(2) 0.0430(4) Uani 1 1 d . . .
H1A H 0.0137 0.4160 0.9118 0.052 Uiso 1 1 calc R . .
N2 N 0.03164(12) 0.43032(12) 0.5961(2) 0.0444(5) Uani 1 1 d . . .
N3 N 0.7083(2) 0.1665(2) 0.7167(10) 0.184(4) Uani 1 1 d D . .
O1 O 0.78523(10) 0.30624(10) 0.71188(19) 0.0522(4) Uani 1 1 d . . .

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
C1 0.0368(9) 0.0368(9) 0.0130(11) 0.000 0.000 0.0184(5)
C2 0.0353(9) 0.0353(9) 0.0167(12) 0.000 0.000 0.0177(5)
C3 0.0350(9) 0.0322(8) 0.0184(8) 0.0008(6) 0.0002(6) 0.0191(7)
C4 0.0400(10) 0.0416(9) 0.0216(8) 0.0010(7) 0.0015(7) 0.0231(8)
C5 0.0346(10) 0.0421(10) 0.0307(9) 0.0060(7) 0.0044(7) 0.0185(8)
C6 0.0302(9) 0.0480(12) 0.0539(11) 0.0016(10) 0.0000(10) 0.0129(8)
C7 0.0353(9) 0.0330(8) 0.0189(8) -0.0012(6) -0.0009(6) 0.0197(8)
C8 0.0375(9) 0.0372(9) 0.0219(8) -0.0024(6) -0.0039(7) 0.0191(8)
C9 0.0379(10) 0.0421(10) 0.0306(9) -0.0055(7) -0.0040(7) 0.0202(9)
C11 0.0422(11) 0.0514(13) 0.0556(13) -0.0012(11) -0.0012(11) 0.0220(11)
C12 0.095(3) 0.0412(18) 0.358(11) 0.006(3) 0.019(5) 0.022(2)
C13 0.260(13) 0.201(11) 0.348(16) 0.025(11) -0.044(12) 0.121(10)
C14 0.229(13) 0.253(13) 0.282(14) 0.001(12) -0.026(10) 0.087(10)
C15 0.148(8) 0.160(8) 0.399(17) -0.015(9) 0.010(9) 0.038(6)
N1 0.0356(9) 0.0482(10) 0.0381(10) 0.0071(7) 0.0080(7) 0.0156(8)
N2 0.0383(9) 0.0476(10) 0.0414(10) -0.0038(7) -0.0037(7) 0.0170(8)
N3 0.059(2) 0.0419(16) 0.442(11) 0.011(3) 0.002(4) 0.0182(14)
O1 0.0499(9) 0.0458(9) 0.0496(9) 0.0003(7) -0.0003(7) 0.0156(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
C1 C3 1.5172(19) 3_565 ?
C1 C3 1.5172(19) . ?
C1 C3 1.5172(19) 2_665 ?
C2 C7 1.521(2) 3_565 ?
C2 C7 1.521(2) . ?
C2 C7 1.521(2) 2_665 ?
C3 C4 1.371(3) . ?
C3 C7 1.428(2) . ?
C4 C5 1.397(3) . ?
C5 N1 1.389(3) . ?
C5 C9 1.397(3) . ?
C6 N1 1.314(3) . ?
C6 N2 1.320(3) . ?
C7 C8 1.391(2) . ?
C8 C9 1.393(3) . ?
C9 N2 1.387(3) . ?
C11 O1 1.213(3) . ?
C11 N3 1.286(4) . ?
C12 C15 1.480(7) . ?
C12 N3 1.492(6) . ?
C13 C14 1.577(9) . ?
C14 N3 1.464(9) . ?

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
C3 C1 C3 106.50(12) 3_565 . ?
C3 C1 C3 106.50(12) 3_565 2_665 ?
C3 C1 C3 106.50(12) . 2_665 ?
C7 C2 C7 105.64(13) 3_565 . ?
C7 C2 C7 105.64(13) 3_565 2_665 ?
C7 C2 C7 105.64(13) . 2_665 ?
C4 C3 C7 121.68(16) . . ?
C4 C3 C1 126.18(17) . . ?
C7 C3 C1 112.12(16) . . ?
C3 C4 C5 116.61(17) . . ?
N1 C5 C9 106.87(18) . . ?
N1 C5 C4 131.14(18) . . ?
C9 C5 C4 121.99(18) . . ?
N1 C6 N2 114.46(19) . . ?
C8 C7 C3 121.54(16) . . ?
C8 C7 C2 125.20(17) . . ?
C3 C7 C2 113.25(16) . . ?
C7 C8 C9 116.15(17) . . ?
N2 C9 C8 130.58(18) . . ?
N2 C9 C5 107.38(18) . . ?
C8 C9 C5 122.03(18) . . ?
O1 C11 N3 127.7(3) . . ?
C15 C12 N3 111.3(7) . . ?
N3 C14 C13 140.4(14) . . ?
C6 N1 C5 105.84(18) . . ?
C6 N2 C9 105.44(19) . . ?
C11 N3 C14 105.8(10) . . ?
C11 N3 C12 119.2(4) . . ?
C14 N3 C12 114.1(9) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        68.32
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.060
