# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_I
_database_code_depnum_ccdc_archive 'CCDC 1453311'
_audit_update_record             
;
2016-02-15 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C28 H34 N4'
_chemical_formula_sum            'C28 H34 N4'
_chemical_formula_iupac          ?
_chemical_formula_weight         426.59

_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                   7.6659(13)
_cell_length_b                   15.982(3)
_cell_length_c                   9.5235(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.263(8)
_cell_angle_gamma                90
_cell_volume                     1165.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    158
_cell_measurement_theta_min      3.6310
_cell_measurement_theta_max      29.6456
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'dark green'
_exptl_crystal_size_max          0.483
_exptl_crystal_size_mid          0.241
_exptl_crystal_size_min          0.136
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460

_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            25895
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         31.20
_diffrn_reflns_theta_full        31.20
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             3766
_reflns_number_gt                3066
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1251
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_number_reflns         3766
_refine_ls_number_parameters     153
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
w=1/[σ²(Fo²)+(0.0727P)²+0.1751P]
where P=(Fo²+2Fc²)/3
;

_atom_sites_solution_hydrogens   mixed
_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         0.495
_refine_diff_density_min         -0.310
_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 Instrument Service v2013.12.0.0'
_computing_cell_refinement       'APEX2 v2014.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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
N N1 0.25752(10) 0.45189(5) 0.55468(8) 0.01255(17) Uani d . . . 1 . .
H H1 0.358(2) 0.4738(9) 0.5317(16) 0.033(4) Uiso d . . . 1 . .
N N2 0.51231(10) 0.56815(5) 0.68891(8) 0.01276(16) Uani d . . . 1 . .
C C1 0.16022(12) 0.39703(6) 0.47267(10) 0.01281(18) Uani d . . . 1 . .
C C2 0.00563(12) 0.37903(6) 0.54626(10) 0.01405(18) Uani d . . . 1 . .
C C3 0.01375(12) 0.42319(6) 0.67070(10) 0.01424(19) Uani d . . . 1 . .
C C4 0.17376(12) 0.46967(6) 0.67623(10) 0.01319(18) Uani d . . . 1 . .
C C5 0.23706(12) 0.52231(6) 0.78310(10) 0.01488(19) Uani d . . . 1 . .
H H5 0.1643 0.5288 0.8608 0.018 Uiso calc U . R 1 . .
C C6 0.39302(12) 0.56655(6) 0.79048(10) 0.01409(19) Uani d . . . 1 . .
C C7 0.45069(14) 0.61755(6) 0.91838(10) 0.0187(2) Uani d . . . 1 . .
H H7A 0.4827 0.5808 0.999 0.022 Uiso calc U . R 1 . .
H H7B 0.3575 0.6564 0.9459 0.022 Uiso calc U . R 1 . .
C C8 0.61046(13) 0.66567(6) 0.86863(10) 0.01473(19) Uani d . . . 1 . .
C C9 0.64340(12) 0.62073(6) 0.72995(9) 0.01300(18) Uani d . . . 1 . .
C C10 0.79219(12) 0.63592(6) 0.65593(10) 0.01378(18) Uani d . . . 1 . .
H H10 0.873 0.6741 0.6987 0.017 Uiso calc U . R 1 . .
C C11 -0.13976(13) 0.32309(7) 0.49573(11) 0.0194(2) Uani d . . . 1 . .
H H11A -0.2449 0.3566 0.4758 0.029 Uiso calc U . R 1 . .
H H11B -0.1633 0.2816 0.5684 0.029 Uiso calc U . R 1 . .
H H11C -0.1064 0.2944 0.4099 0.029 Uiso calc U . R 1 . .
C C12 -0.12067(13) 0.42320(7) 0.78071(11) 0.0185(2) Uani d . . . 1 . .
H H12A -0.1167 0.3697 0.8311 0.028 Uiso calc U . R 1 . .
H H12B -0.2368 0.4309 0.7359 0.028 Uiso calc U . R 1 . .
H H12C -0.0964 0.469 0.8471 0.028 Uiso calc U . R 1 . .
C C13 0.76717(15) 0.65959(7) 0.97297(11) 0.0218(2) Uani d . . . 1 . .
H H13A 0.867 0.689 0.9349 0.033 Uiso calc U . R 1 . .
H H13B 0.7975 0.6006 0.9884 0.033 Uiso calc U . R 1 . .
H H13C 0.7373 0.6852 1.0624 0.033 Uiso calc U . R 1 . .
C C14 0.56553(14) 0.75771(6) 0.83907(11) 0.0191(2) Uani d . . . 1 . .
H H14A 0.5349 0.7852 0.9267 0.029 Uiso calc U . R 1 . .
H H14B 0.4664 0.7609 0.7711 0.029 Uiso calc U . R 1 . .
H H14C 0.6667 0.7858 0.8005 0.029 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
N1 C1 . 1.3744(12) ?
N1 C4 . 1.3754(12) ?
N1 H1 . 0.879(16) ?
N2 C9 . 1.3556(12) ?
N2 C6 . 1.3573(12) ?
C1 C10 3_666 1.3950(13) ?
C1 C2 . 1.4297(13) ?
C2 C3 . 1.3787(14) ?
C2 C11 . 1.4935(13) ?
C3 C4 . 1.4332(13) ?
C3 C12 . 1.4982(13) ?
C4 C5 . 1.3929(13) ?
C5 C6 . 1.3884(13) ?
C5 H5 . 0.95 ?
C6 C7 . 1.5169(13) ?
C7 C8 . 1.5368(14) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C13 . 1.5316(14) ?
C8 C9 . 1.5331(13) ?
C8 C14 . 1.5343(14) ?
C9 C10 . 1.3858(13) ?
C10 C1 3_666 1.3950(13) ?
C10 H10 . 0.95 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?

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
C1 N1 C4 . . 110.43(8) ?
C1 N1 H1 . . 124.9(10) ?
C4 N1 H1 . . 124.6(10) ?
C9 N2 C6 . . 108.59(8) ?
N1 C1 C10 . 3_666 125.80(8) ?
N1 C1 C2 . . 106.95(8) ?
C10 C1 C2 3_666 . 127.23(9) ?
C3 C2 C1 . . 107.95(8) ?
C3 C2 C11 . . 126.24(9) ?
C1 C2 C11 . . 125.80(9) ?
C2 C3 C4 . . 107.84(8) ?
C2 C3 C12 . . 126.31(9) ?
C4 C3 C12 . . 125.84(9) ?
N1 C4 C5 . . 125.38(8) ?
N1 C4 C3 . . 106.82(8) ?
C5 C4 C3 . . 127.80(9) ?
C6 C5 C4 . . 128.24(9) ?
C6 C5 H5 . . 115.9 ?
C4 C5 H5 . . 115.9 ?
N2 C6 C5 . . 125.21(9) ?
N2 C6 C7 . . 112.27(8) ?
C5 C6 C7 . . 122.50(8) ?
C6 C7 C8 . . 103.41(8) ?
C6 C7 H7A . . 111.1 ?
C8 C7 H7A . . 111.1 ?
C6 C7 H7B . . 111.1 ?
C8 C7 H7B . . 111.1 ?
H7A C7 H7B . . 109.0 ?
C13 C8 C9 . . 112.18(8) ?
C13 C8 C14 . . 110.15(8) ?
C9 C8 C14 . . 109.54(8) ?
C13 C8 C7 . . 112.49(8) ?
C9 C8 C7 . . 101.04(7) ?
C14 C8 C7 . . 111.13(8) ?
N2 C9 C10 . . 125.28(8) ?
N2 C9 C8 . . 113.17(8) ?
C10 C9 C8 . . 121.53(8) ?
C9 C10 C1 . 3_666 129.01(9) ?
C9 C10 H10 . . 115.5 ?
C1 C10 H10 3_666 . 115.5 ?
C2 C11 H11A . . 109.5 ?
C2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C3 C12 H12A . . 109.5 ?
C3 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C3 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C8 C13 H13A . . 109.5 ?
C8 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C8 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C8 C14 H14A . . 109.5 ?
C8 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C8 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?

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
C4 N1 C1 C10 . . . 3_666 -178.31(9) ?
C4 N1 C1 C2 . . . . 0.10(10) ?
N1 C1 C2 C3 . . . . -0.17(10) ?
C10 C1 C2 C3 3_666 . . . 178.21(9) ?
N1 C1 C2 C11 . . . . 179.07(9) ?
C10 C1 C2 C11 3_666 . . . -2.56(16) ?
C1 C2 C3 C4 . . . . 0.17(10) ?
C11 C2 C3 C4 . . . . -179.06(9) ?
C1 C2 C3 C12 . . . . 179.91(9) ?
C11 C2 C3 C12 . . . . 0.68(16) ?
C1 N1 C4 C5 . . . . 179.28(9) ?
C1 N1 C4 C3 . . . . 0.01(10) ?
C2 C3 C4 N1 . . . . -0.11(10) ?
C12 C3 C4 N1 . . . . -179.85(9) ?
C2 C3 C4 C5 . . . . -179.37(9) ?
C12 C3 C4 C5 . . . . 0.89(16) ?
N1 C4 C5 C6 . . . . -0.24(16) ?
C3 C4 C5 C6 . . . . 178.88(9) ?
C9 N2 C6 C5 . . . . 177.22(9) ?
C9 N2 C6 C7 . . . . -4.33(11) ?
C4 C5 C6 N2 . . . . 2.29(16) ?
C4 C5 C6 C7 . . . . -176.01(9) ?
N2 C6 C7 C8 . . . . 10.71(11) ?
C5 C6 C7 C8 . . . . -170.79(9) ?
C6 C7 C8 C13 . . . . -131.41(9) ?
C6 C7 C8 C9 . . . . -11.60(10) ?
C6 C7 C8 C14 . . . . 104.56(9) ?
C6 N2 C9 C10 . . . . 177.33(9) ?
C6 N2 C9 C8 . . . . -4.23(10) ?
C13 C8 C9 N2 . . . . 130.48(9) ?
C14 C8 C9 N2 . . . . -106.87(9) ?
C7 C8 C9 N2 . . . . 10.46(10) ?
C13 C8 C9 C10 . . . . -51.01(12) ?
C14 C8 C9 C10 . . . . 71.64(11) ?
C7 C8 C9 C10 . . . . -171.04(9) ?
N2 C9 C10 C1 . . . 3_666 0.56(16) ?
C8 C9 C10 C1 . . . 3_666 -177.75(9) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N2 . 0.879(16) 2.404(15) 2.9503(12) 120.6(13) ?
N1 H1 N2 3_666 0.879(16) 2.455(16) 2.9867(12) 119.5(12) ?

