# Electronic Supplementary Material (ESI) for Chemical Science
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_k81i5
#TrackingRef '17614_web_deposit_cif_file_0_JeffreyAube_1360260618.K81I.CIF'


_audit_creation_method           SHELXTL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 N4'
_chemical_formula_weight         242.32

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                   6.9434(14)
_cell_length_b                   18.717(4)
_cell_length_c                   9.893(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.190(2)
_cell_angle_gamma                90.00
_cell_volume                     1280.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      29.16

_exptl_crystal_description       Irregular
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'Bruker SMART APEX 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_%        0.00
_diffrn_reflns_number            5681
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0102
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         29.20
_reflns_number_total             5680
_reflns_number_gt                5091
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0807P)^2^+0.2392P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5693
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1475
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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
N1 N 0.24106(11) 0.52697(4) 0.91350(7) 0.01636(17) Uani 1 1 d . . .
N2 N 0.21914(10) 0.54333(4) 0.78164(7) 0.01562(17) Uani 1 1 d . . .
N3 N 0.23831(11) 0.60863(4) 0.75586(7) 0.01528(17) Uani 1 1 d . . .
N4 N -0.15445(12) 0.60388(5) 0.52836(9) 0.0259(2) Uani 1 1 d . . .
C1 C 0.21376(12) 0.61974(4) 0.60607(8) 0.01387(18) Uani 1 1 d . . .
C2 C 0.26670(13) 0.69773(5) 0.57855(9) 0.01736(18) Uani 1 1 d . . .
H2A H 0.1837(18) 0.7302(7) 0.6233(13) 0.025(3) Uiso 1 1 d . . .
H2B H 0.4019(18) 0.7040(7) 0.6199(12) 0.020(3) Uiso 1 1 d . . .
C3 C 0.25550(15) 0.71387(5) 0.42705(9) 0.0201(2) Uani 1 1 d . . .
H3A H 0.1160(19) 0.7099(7) 0.3871(13) 0.028(3) Uiso 1 1 d . . .
H3B H 0.2958(19) 0.7642(8) 0.4145(14) 0.033(4) Uiso 1 1 d . . .
C4 C 0.38131(13) 0.66276(5) 0.35375(9) 0.0193(2) Uani 1 1 d . . .
H4A H 0.5171(18) 0.6705(7) 0.3851(13) 0.023(3) Uiso 1 1 d . . .
H4B H 0.3726(18) 0.6736(7) 0.2562(13) 0.023(3) Uiso 1 1 d . . .
C5 C 0.32736(13) 0.58532(5) 0.37917(9) 0.01706(19) Uani 1 1 d . . .
H5A H 0.1936(18) 0.5758(6) 0.3381(12) 0.020(3) Uiso 1 1 d . . .
H5B H 0.4144(19) 0.5526(7) 0.3342(13) 0.026(3) Uiso 1 1 d . . .
C6 C 0.33886(12) 0.56860(4) 0.53002(8) 0.01544(18) Uani 1 1 d . . .
H6A H 0.4693(19) 0.5752(7) 0.5689(13) 0.022(3) Uiso 1 1 d . . .
H6B H 0.3015(18) 0.5189(7) 0.5448(13) 0.024(3) Uiso 1 1 d . . .
C7 C 0.00640(13) 0.60941(5) 0.56134(9) 0.01712(19) Uani 1 1 d . . .
C8 C 0.27844(16) 0.58299(5) 1.01403(9) 0.0213(2) Uani 1 1 d . . .
H8A H 0.378(2) 0.6150(9) 0.9853(17) 0.045(4) Uiso 1 1 d . . .
H8B H 0.168(3) 0.6093(9) 1.0236(17) 0.048(4) Uiso 1 1 d . . .
H8C H 0.330(3) 0.5627(9) 1.0955(19) 0.056(5) Uiso 1 1 d . . .
C9 C 0.22947(12) 0.45350(5) 0.94544(9) 0.01527(18) Uani 1 1 d . . .
C10 C 0.23206(14) 0.43123(5) 1.07966(9) 0.0201(2) Uani 1 1 d . . .
H10 H 0.234(2) 0.4660(8) 1.1553(14) 0.034(3) Uiso 1 1 d . . .
C11 C 0.22769(15) 0.35867(6) 1.11022(10) 0.0239(2) Uani 1 1 d . . .
H11 H 0.229(2) 0.3436(8) 1.2020(15) 0.034(4) Uiso 1 1 d . . .
C12 C 0.21864(14) 0.30757(5) 1.00866(10) 0.0226(2) Uani 1 1 d . . .
H12 H 0.2161(19) 0.2575(7) 1.0298(13) 0.026(3) Uiso 1 1 d . . .
C13 C 0.21235(13) 0.33019(5) 0.87487(10) 0.0208(2) Uani 1 1 d . . .
H13 H 0.2026(18) 0.2947(7) 0.8003(13) 0.025(3) Uiso 1 1 d . . .
C14 C 0.21788(13) 0.40208(5) 0.84201(9) 0.01824(19) Uani 1 1 d . . .
H14 H 0.218(2) 0.4180(7) 0.7491(14) 0.028(3) Uiso 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
N1 0.0215(4) 0.0157(4) 0.0118(3) -0.0004(3) 0.0011(3) -0.0004(3)
N2 0.0161(3) 0.0176(3) 0.0132(3) 0.0009(3) 0.0014(3) 0.0006(3)
N3 0.0162(3) 0.0167(4) 0.0128(3) -0.0001(2) 0.0007(3) 0.0004(3)
N4 0.0193(4) 0.0321(5) 0.0257(4) 0.0001(3) -0.0005(3) -0.0006(3)
C1 0.0151(4) 0.0139(4) 0.0124(4) -0.0004(3) -0.0002(3) 0.0001(3)
C2 0.0235(4) 0.0128(4) 0.0159(4) -0.0011(3) 0.0021(3) -0.0011(3)
C3 0.0293(5) 0.0135(4) 0.0177(4) 0.0019(3) 0.0038(3) 0.0017(3)
C4 0.0230(4) 0.0189(4) 0.0165(4) 0.0024(3) 0.0044(3) 0.0012(3)
C5 0.0218(4) 0.0162(4) 0.0134(4) 0.0000(3) 0.0027(3) 0.0034(3)
C6 0.0180(4) 0.0142(4) 0.0142(4) 0.0007(3) 0.0023(3) 0.0031(3)
C7 0.0187(4) 0.0174(4) 0.0153(4) 0.0000(3) 0.0015(3) 0.0010(3)
C8 0.0301(5) 0.0189(4) 0.0146(4) -0.0027(3) 0.0004(3) -0.0021(4)
C9 0.0129(4) 0.0168(4) 0.0162(4) 0.0013(3) 0.0019(3) 0.0004(3)
C10 0.0238(4) 0.0207(4) 0.0159(4) 0.0010(3) 0.0031(3) 0.0006(3)
C11 0.0280(5) 0.0242(5) 0.0199(4) 0.0060(4) 0.0042(4) 0.0001(4)
C12 0.0222(4) 0.0182(4) 0.0276(5) 0.0046(4) 0.0041(3) 0.0000(3)
C13 0.0209(4) 0.0186(4) 0.0231(5) -0.0020(3) 0.0036(3) -0.0007(3)
C14 0.0193(4) 0.0193(4) 0.0163(4) -0.0002(3) 0.0026(3) -0.0002(3)

_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
N1 N2 1.3352(10) . ?
N1 C9 1.4148(11) . ?
N1 C8 1.4524(11) . ?
N2 N3 1.2579(11) . ?
N3 C1 1.4908(11) . ?
N4 C7 1.1396(13) . ?
C1 C7 1.4802(12) . ?
C1 C6 1.5346(11) . ?
C1 C2 1.5357(12) . ?
C2 C3 1.5240(12) . ?
C2 H2A 0.972(13) . ?
C2 H2B 0.996(12) . ?
C3 C4 1.5227(12) . ?
C3 H3A 1.015(13) . ?
C3 H3B 0.995(14) . ?
C4 C5 1.5236(13) . ?
C4 H4A 0.976(13) . ?
C4 H4B 0.983(13) . ?
C5 C6 1.5198(12) . ?
C5 H5A 0.995(12) . ?
C5 H5B 0.993(13) . ?
C6 H6A 0.960(13) . ?
C6 H6B 0.980(13) . ?
C8 H8A 0.975(17) . ?
C8 H8B 0.921(18) . ?
C8 H8C 0.932(19) . ?
C9 C10 1.3903(12) . ?
C9 C14 1.4017(12) . ?
C10 C11 1.3923(13) . ?
C10 H10 0.991(14) . ?
C11 C12 1.3845(14) . ?
C11 H11 0.950(15) . ?
C12 C13 1.3865(14) . ?
C12 H12 0.961(14) . ?
C13 C14 1.3857(13) . ?
C13 H13 0.991(13) . ?
C14 H14 0.966(14) . ?

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
N2 N1 C9 115.94(7) . . ?
N2 N1 C8 120.06(7) . . ?
C9 N1 C8 123.99(7) . . ?
N3 N2 N1 114.59(7) . . ?
N2 N3 C1 109.41(7) . . ?
C7 C1 N3 107.44(7) . . ?
C7 C1 C6 110.51(7) . . ?
N3 C1 C6 112.43(7) . . ?
C7 C1 C2 108.24(7) . . ?
N3 C1 C2 107.53(7) . . ?
C6 C1 C2 110.53(7) . . ?
C3 C2 C1 111.78(7) . . ?
C3 C2 H2A 110.1(8) . . ?
C1 C2 H2A 110.7(8) . . ?
C3 C2 H2B 110.1(7) . . ?
C1 C2 H2B 105.7(7) . . ?
H2A C2 H2B 108.4(10) . . ?
C4 C3 C2 111.31(7) . . ?
C4 C3 H3A 109.7(8) . . ?
C2 C3 H3A 109.3(8) . . ?
C4 C3 H3B 110.9(8) . . ?
C2 C3 H3B 108.7(8) . . ?
H3A C3 H3B 106.8(11) . . ?
C3 C4 C5 111.03(7) . . ?
C3 C4 H4A 109.5(7) . . ?
C5 C4 H4A 109.5(8) . . ?
C3 C4 H4B 110.5(7) . . ?
C5 C4 H4B 111.4(7) . . ?
H4A C4 H4B 104.6(10) . . ?
C6 C5 C4 111.47(7) . . ?
C6 C5 H5A 109.2(7) . . ?
C4 C5 H5A 109.7(7) . . ?
C6 C5 H5B 109.5(7) . . ?
C4 C5 H5B 110.1(8) . . ?
H5A C5 H5B 106.8(10) . . ?
C5 C6 C1 111.80(7) . . ?
C5 C6 H6A 109.3(8) . . ?
C1 C6 H6A 106.2(8) . . ?
C5 C6 H6B 110.6(7) . . ?
C1 C6 H6B 110.4(8) . . ?
H6A C6 H6B 108.4(10) . . ?
N4 C7 C1 177.57(10) . . ?
N1 C8 H8A 109.3(10) . . ?
N1 C8 H8B 110.9(11) . . ?
H8A C8 H8B 108.6(15) . . ?
N1 C8 H8C 109.1(11) . . ?
H8A C8 H8C 106.0(15) . . ?
H8B C8 H8C 112.7(15) . . ?
C10 C9 C14 119.10(8) . . ?
C10 C9 N1 120.57(8) . . ?
C14 C9 N1 120.33(8) . . ?
C9 C10 C11 120.08(9) . . ?
C9 C10 H10 121.5(8) . . ?
C11 C10 H10 118.4(8) . . ?
C12 C11 C10 121.11(9) . . ?
C12 C11 H11 119.0(9) . . ?
C10 C11 H11 119.9(9) . . ?
C11 C12 C13 118.51(9) . . ?
C11 C12 H12 121.1(8) . . ?
C13 C12 H12 120.4(8) . . ?
C14 C13 C12 121.42(9) . . ?
C14 C13 H13 118.6(8) . . ?
C12 C13 H13 120.0(8) . . ?
C13 C14 C9 119.76(8) . . ?
C13 C14 H14 121.6(8) . . ?
C9 C14 H14 118.6(8) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 N2 N3 -177.11(7) . . . . ?
C8 N1 N2 N3 1.63(12) . . . . ?
N1 N2 N3 C1 179.11(7) . . . . ?
N2 N3 C1 C7 71.62(8) . . . . ?
N2 N3 C1 C6 -50.18(9) . . . . ?
N2 N3 C1 C2 -172.06(7) . . . . ?
C7 C1 C2 C3 -66.90(9) . . . . ?
N3 C1 C2 C3 177.32(7) . . . . ?
C6 C1 C2 C3 54.26(10) . . . . ?
C1 C2 C3 C4 -55.44(10) . . . . ?
C2 C3 C4 C5 55.72(10) . . . . ?
C3 C4 C5 C6 -55.80(10) . . . . ?
C4 C5 C6 C1 55.47(10) . . . . ?
C7 C1 C6 C5 65.54(9) . . . . ?
N3 C1 C6 C5 -174.43(7) . . . . ?
C2 C1 C6 C5 -54.26(9) . . . . ?
N3 C1 C7 N4 81(2) . . . . ?
C6 C1 C7 N4 -156(2) . . . . ?
C2 C1 C7 N4 -35(2) . . . . ?
N2 N1 C9 C10 -173.92(8) . . . . ?
C8 N1 C9 C10 7.40(13) . . . . ?
N2 N1 C9 C14 6.96(12) . . . . ?
C8 N1 C9 C14 -171.72(8) . . . . ?
C14 C9 C10 C11 1.47(13) . . . . ?
N1 C9 C10 C11 -177.66(8) . . . . ?
C9 C10 C11 C12 -0.70(15) . . . . ?
C10 C11 C12 C13 -0.53(15) . . . . ?
C11 C12 C13 C14 0.98(14) . . . . ?
C12 C13 C14 C9 -0.21(14) . . . . ?
C10 C9 C14 C13 -1.03(13) . . . . ?
N1 C9 C14 C13 178.10(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.096


_database_code_depnum_ccdc_archive 'CCDC 923835'