# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1865986'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2018-11-14 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C36 H36 N6'
_chemical_formula_sum            'C36 H36 N6'
_chemical_formula_iupac          ?
_chemical_formula_weight         552.71

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.0765(6)
_cell_length_b                   13.7569(6)
_cell_length_c                   8.1842(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.4200(10)
_cell_angle_gamma                90
_cell_volume                     1443.13(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8135
_cell_measurement_theta_min      2.1717
_cell_measurement_theta_max      27.4529
_cell_measurement_temperature    113.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'metallic green-blue'
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588

_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      113.(2)

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ImuS

_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            9954
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
;

_reflns_number_total             2643
_reflns_number_gt                2399
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1045
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_number_reflns         2643
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0374P)²+0.7596P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.251
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.30183(10) 0.54354(10) 0.70606(16) 0.0168(3) Uani d . . . 1 . .
C C2 0.30216(10) 0.45334(10) 0.62838(16) 0.0170(3) Uani d . . . 1 . .
C C3 0.22179(11) 0.37618(10) 0.64005(19) 0.0226(3) Uani d . . . 1 . .
H H3A 0.2289 0.3521 0.7557 0.027 Uiso calc U . R 1 . .
H H3B 0.1501 0.4012 0.6011 0.027 Uiso calc U . R 1 . .
C C4 0.24721(11) 0.29753(11) 0.52605(19) 0.0242(3) Uani d . . . 1 . .
H H4A 0.2573 0.2341 0.5842 0.029 Uiso calc U . R 1 . .
H H4B 0.1912 0.2911 0.4257 0.029 Uiso calc U . R 1 . .
C C5 0.34707(10) 0.33251(10) 0.48096(17) 0.0189(3) Uani d . . . 1 . .
C C6 0.48832(11) 0.29810(10) 0.35234(17) 0.0186(3) Uani d . . . 1 . .
C C7 0.54644(11) 0.23472(11) 0.26757(18) 0.0226(3) Uani d . . . 1 . .
H H7 0.5298 0.1689 0.2391 0.027 Uiso calc U . R 1 . .
C C8 0.63037(11) 0.28476(10) 0.23417(18) 0.0208(3) Uani d . . . 1 . .
H H8 0.6813 0.2603 0.1766 0.025 Uiso calc U . R 1 . .
C C9 0.62765(10) 0.38056(10) 0.30150(16) 0.0173(3) Uani d . . . 1 . .
C C10 0.22109(10) 0.56272(10) 0.80897(17) 0.0172(3) Uani d . . . 1 . .
C C11 0.24365(11) 0.54181(10) 0.98034(17) 0.0193(3) Uani d . . . 1 . .
C C12 0.17021(11) 0.56504(10) 1.07608(18) 0.0213(3) Uani d . . . 1 . .
H H12 0.186 0.5522 1.1924 0.026 Uiso calc U . R 1 . .
C C13 0.07420(11) 0.60659(10) 1.00656(18) 0.0201(3) Uani d . . . 1 . .
C C14 0.05283(11) 0.62394(10) 0.83620(18) 0.0199(3) Uani d . . . 1 . .
H H14 -0.0128 0.6509 0.7864 0.024 Uiso calc U . R 1 . .
C C15 0.12433(11) 0.60313(10) 0.73584(17) 0.0186(3) Uani d . . . 1 . .
C C16 0.09875(12) 0.62423(12) 0.55141(18) 0.0265(4) Uani d . . . 1 . .
H H16A 0.0278 0.6504 0.5213 0.04 Uiso calc U . R 1 . .
H H16B 0.1035 0.5641 0.4892 0.04 Uiso calc U . R 1 . .
H H16C 0.1484 0.6719 0.5239 0.04 Uiso calc U . R 1 . .
C C17 -0.00368(12) 0.63196(11) 1.11228(19) 0.0265(3) Uani d . . . 1 . .
H H17A -0.0671 0.6577 1.0413 0.04 Uiso calc U . R 1 . .
H H17B 0.0262 0.6811 1.1947 0.04 Uiso calc U . R 1 . .
H H17C -0.0209 0.5736 1.1699 0.04 Uiso calc U . R 1 . .
C C18 0.34629(11) 0.49565(12) 1.06009(19) 0.0266(4) Uani d . . . 1 . .
H H18A 0.3485 0.4865 1.1795 0.04 Uiso calc U . R 1 . .
H H18B 0.4038 0.5381 1.0447 0.04 Uiso calc U . R 1 . .
H H18C 0.3531 0.4325 1.0078 0.04 Uiso calc U . R 1 . .
N N1 0.39894(9) 0.27431(8) 0.39705(15) 0.0207(3) Uani d . . . 1 . .
N N2 0.37285(8) 0.42371(8) 0.53773(14) 0.0170(3) Uani d . . . 1 . .
N N3 0.54162(8) 0.38477(8) 0.37415(14) 0.0166(3) Uani d . . . 1 . .
H H3 0.5233 0.4356 0.427 0.02 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.395(2) ?
C1 C9 3_666 1.4024(19) ?
C1 C10 . 1.4986(19) ?
C2 N2 . 1.3574(18) ?
C2 C3 . 1.5100(18) ?
C3 C4 . 1.508(2) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.5046(19) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 N1 . 1.3256(18) ?
C5 N2 . 1.3570(18) ?
C6 N1 . 1.3328(18) ?
C6 N3 . 1.3748(18) ?
C6 C7 . 1.424(2) ?
C7 C8 . 1.368(2) ?
C7 H7 . 0.95 ?
C8 C9 . 1.4316(19) ?
C8 H8 . 0.95 ?
C9 N3 . 1.3738(18) ?
C9 C1 3_666 1.4024(19) ?
C10 C15 . 1.4030(19) ?
C10 C11 . 1.4046(19) ?
C11 C12 . 1.391(2) ?
C11 C18 . 1.5112(19) ?
C12 C13 . 1.394(2) ?
C12 H12 . 0.95 ?
C13 C14 . 1.387(2) ?
C13 C17 . 1.502(2) ?
C14 C15 . 1.391(2) ?
C14 H14 . 0.95 ?
C15 C16 . 1.5082(19) ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
N3 H3 . 0.88 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C9 . 3_666 125.51(13) ?
C2 C1 C10 . . 118.62(12) ?
C9 C1 C10 3_666 . 115.87(12) ?
N2 C2 C1 . . 125.47(12) ?
N2 C2 C3 . . 112.41(12) ?
C1 C2 C3 . . 122.12(12) ?
C4 C3 C2 . . 102.93(11) ?
C4 C3 H3A . . 111.2 ?
C2 C3 H3A . . 111.2 ?
C4 C3 H3B . . 111.2 ?
C2 C3 H3B . . 111.2 ?
H3A C3 H3B . . 109.1 ?
C5 C4 C3 . . 103.33(11) ?
C5 C4 H4A . . 111.1 ?
C3 C4 H4A . . 111.1 ?
C5 C4 H4B . . 111.1 ?
C3 C4 H4B . . 111.1 ?
H4A C4 H4B . . 109.1 ?
N1 C5 N2 . . 128.16(12) ?
N1 C5 C4 . . 119.46(12) ?
N2 C5 C4 . . 112.37(12) ?
N1 C6 N3 . . 128.83(13) ?
N1 C6 C7 . . 124.40(13) ?
N3 C6 C7 . . 106.77(12) ?
C8 C7 C6 . . 108.41(12) ?
C8 C7 H7 . . 125.8 ?
C6 C7 H7 . . 125.8 ?
C7 C8 C9 . . 107.72(12) ?
C7 C8 H8 . . 126.1 ?
C9 C8 H8 . . 126.1 ?
N3 C9 C1 . 3_666 126.13(12) ?
N3 C9 C8 . . 106.87(12) ?
C1 C9 C8 3_666 . 126.99(13) ?
C15 C10 C11 . . 120.03(13) ?
C15 C10 C1 . . 120.41(12) ?
C11 C10 C1 . . 119.55(12) ?
C12 C11 C10 . . 118.91(13) ?
C12 C11 C18 . . 120.41(13) ?
C10 C11 C18 . . 120.68(12) ?
C11 C12 C13 . . 122.03(13) ?
C11 C12 H12 . . 119.0 ?
C13 C12 H12 . . 119.0 ?
C14 C13 C12 . . 117.82(13) ?
C14 C13 C17 . . 120.95(13) ?
C12 C13 C17 . . 121.24(13) ?
C13 C14 C15 . . 122.20(13) ?
C13 C14 H14 . . 118.9 ?
C15 C14 H14 . . 118.9 ?
C14 C15 C10 . . 118.98(13) ?
C14 C15 C16 . . 120.64(12) ?
C10 C15 C16 . . 120.38(13) ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C13 C17 H17A . . 109.5 ?
C13 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C13 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C11 C18 H18A . . 109.5 ?
C11 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C11 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C5 N1 C6 . . 124.08(12) ?
C5 N2 C2 . . 108.36(11) ?
C9 N3 C6 . . 110.17(11) ?
C9 N3 H3 . . 124.9 ?
C6 N3 H3 . . 124.9 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 C1 C2 N2 3_666 . . . 2.3(2) ?
C10 C1 C2 N2 . . . . -176.89(12) ?
C9 C1 C2 C3 3_666 . . . -178.72(13) ?
C10 C1 C2 C3 . . . . 2.12(19) ?
N2 C2 C3 C4 . . . . -5.91(15) ?
C1 C2 C3 C4 . . . . 174.97(13) ?
C2 C3 C4 C5 . . . . 7.31(14) ?
C3 C4 C5 N1 . . . . 171.76(13) ?
C3 C4 C5 N2 . . . . -7.27(16) ?
N1 C6 C7 C8 . . . . 176.85(13) ?
N3 C6 C7 C8 . . . . -2.38(16) ?
C6 C7 C8 C9 . . . . 1.35(16) ?
C7 C8 C9 N3 . . . . 0.18(15) ?
C7 C8 C9 C1 . . . 3_666 -179.19(13) ?
C2 C1 C10 C15 . . . . -89.96(16) ?
C9 C1 C10 C15 3_666 . . . 90.79(16) ?
C2 C1 C10 C11 . . . . 91.33(16) ?
C9 C1 C10 C11 3_666 . . . -87.91(16) ?
C15 C10 C11 C12 . . . . -2.3(2) ?
C1 C10 C11 C12 . . . . 176.43(12) ?
C15 C10 C11 C18 . . . . 178.25(13) ?
C1 C10 C11 C18 . . . . -3.0(2) ?
C10 C11 C12 C13 . . . . 1.3(2) ?
C18 C11 C12 C13 . . . . -179.21(13) ?
C11 C12 C13 C14 . . . . 0.5(2) ?
C11 C12 C13 C17 . . . . -179.45(13) ?
C12 C13 C14 C15 . . . . -1.3(2) ?
C17 C13 C14 C15 . . . . 178.59(13) ?
C13 C14 C15 C10 . . . . 0.4(2) ?
C13 C14 C15 C16 . . . . -179.21(13) ?
C11 C10 C15 C14 . . . . 1.5(2) ?
C1 C10 C15 C14 . . . . -177.24(12) ?
C11 C10 C15 C16 . . . . -178.96(13) ?
C1 C10 C15 C16 . . . . 2.3(2) ?
N2 C5 N1 C6 . . . . -0.6(2) ?
C4 C5 N1 C6 . . . . -179.47(13) ?
N3 C6 N1 C5 . . . . -3.3(2) ?
C7 C6 N1 C5 . . . . 177.60(13) ?
N1 C5 N2 C2 . . . . -175.18(14) ?
C4 C5 N2 C2 . . . . 3.75(15) ?
C1 C2 N2 C5 . . . . -179.38(13) ?
C3 C2 N2 C5 . . . . 1.52(15) ?
C1 C9 N3 C6 3_666 . . . 177.66(13) ?
C8 C9 N3 C6 . . . . -1.72(15) ?
N1 C6 N3 C9 . . . . -176.66(13) ?
C7 C6 N3 C9 . . . . 2.53(15) ?



