# Electronic Supplementary Material (ESI) for Organic .
# 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_ccc



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C30 H30 N6'

_chemical_formula_weight         474.60



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                   25.257(13)

_cell_length_b                   7.226(4)

_cell_length_c                   14.807(8)

_cell_angle_alpha                90.00

_cell_angle_beta                 106.999(6)

_cell_angle_gamma                90.00

_cell_volume                     2584(2)

_cell_formula_units_Z            4

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    3124

_cell_measurement_theta_min      2.88

_cell_measurement_theta_max      21.86



_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.33

_exptl_crystal_size_mid          0.25

_exptl_crystal_size_min          0.11

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.220

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             1008

_exptl_absorpt_coefficient_mu    0.075

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9758

_exptl_absorpt_correction_T_max  0.9919

_exptl_absorpt_process_details   sadabs



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      296(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  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            4741

_diffrn_reflns_av_R_equivalents  0.0000

_diffrn_reflns_av_sigmaI/netI    0.0462

_diffrn_reflns_limit_h_min       -30

_diffrn_reflns_limit_h_max       30

_diffrn_reflns_limit_k_min       -8

_diffrn_reflns_limit_k_max       8

_diffrn_reflns_limit_l_min       -17

_diffrn_reflns_limit_l_max       17

_diffrn_reflns_theta_min         2.53

_diffrn_reflns_theta_max         25.50

_reflns_number_total             4741

_reflns_number_gt                3188

_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.

;



_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)+(0.0682P)²+0.3364P] 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     SHELXL

_refine_ls_extinction_coef       0.0037(8)

_refine_ls_extinction_expression 
Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

_refine_ls_number_reflns         4741

_refine_ls_number_parameters     333

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0849

_refine_ls_R_factor_gt           0.0519

_refine_ls_wR_factor_ref         0.1477

_refine_ls_wR_factor_gt          0.1307

_refine_ls_goodness_of_fit_ref   1.045

_refine_ls_restrained_S_all      1.045

_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


































































C1 C 0.87887(17) 0.2349(5) 0.0809(4) 0.0536(13) Uani 1 1 d . . .
C2 C 0.86026(15) 0.0760(7) 0.1145(3) 0.0729(14) Uani 1 1 d . . .
H2 H 0.8801 -0.0338 0.1194 0.088 Uiso 1 1 calc R . .
C3 C 0.81203(18) 0.0822(8) 0.1405(4) 0.0892(17) Uani 1 1 d . . .
H3 H 0.7991 -0.0253 0.1614 0.107 Uiso 1 1 calc R . .
C4 C 0.7829(2) 0.2434(8) 0.1362(5) 0.090(2) Uani 1 1 d . . .
H4 H 0.7511 0.2462 0.1557 0.108 Uiso 1 1 calc R . .
C5 C 0.80116(16) 0.4006(8) 0.1029(4) 0.0917(18) Uani 1 1 d . . .
H5 H 0.7813 0.5101 0.0989 0.110 Uiso 1 1 calc R . .
C6 C 0.84931(13) 0.3976(6) 0.0749(4) 0.0713(14) Uani 1 1 d . . .
H6 H 0.8615 0.5046 0.0523 0.086 Uiso 1 1 calc R . .
C7 C 0.93237(18) 0.2313(5) 0.0557(4) 0.0496(12) Uani 1 1 d . . .
C8 C 0.93600(17) 0.2729(5) -0.0353(4) 0.0452(12) Uani 1 1 d . . .
C9 C 0.98639(18) 0.2728(5) -0.0527(4) 0.0474(12) Uani 1 1 d . . .
C10 C 1.02596(12) 0.1894(5) 0.1116(3) 0.0475(10) Uani 1 1 d . . .
C11 C 1.07974(13) 0.1583(5) 0.1679(3) 0.0610(12) Uani 1 1 d . . .
H11 H 1.0908 0.1251 0.2313 0.073 Uiso 1 1 calc R . .
C12 C 1.11345(13) 0.1863(6) 0.1111(3) 0.0576(11) Uani 1 1 d . . .
C13 C 1.17564(13) 0.1741(7) 0.1352(3) 0.0823(15) Uani 1 1 d . . .
H13A H 1.1855 0.1010 0.0884 0.123 Uiso 1 1 calc R . .
H13B H 1.1902 0.1173 0.1961 0.123 Uiso 1 1 calc R . .
H13C H 1.1908 0.2962 0.1365 0.123 Uiso 1 1 calc R . .
C14 C 0.99867(16) 0.3111(6) -0.1430(3) 0.0631(11) Uani 1 1 d . . .
H14A H 0.9688 0.3809 -0.1839 0.095 Uiso 1 1 calc R . .
H14B H 1.0027 0.1963 -0.1730 0.095 Uiso 1 1 calc R . .
H14C H 1.0324 0.3809 -0.1307 0.095 Uiso 1 1 calc R . .
C15 C 0.88512(15) 0.3108(6) -0.1173(3) 0.0610(11) Uani 1 1 d . . .
H15A H 0.8880 0.4314 -0.1426 0.092 Uiso 1 1 calc R . .
H15B H 0.8528 0.3059 -0.0958 0.092 Uiso 1 1 calc R . .
H15C H 0.8822 0.2192 -0.1654 0.092 Uiso 1 1 calc R . .
C16 C 0.61844(17) 0.2674(5) 0.6986(4) 0.0505(12) Uani 1 1 d . . .
C17 C 0.63948(15) 0.4234(7) 0.7500(3) 0.0687(13) Uani 1 1 d . . .
H17 H 0.6214 0.5363 0.7346 0.082 Uiso 1 1 calc R . .
C18 C 0.68783(17) 0.4117(8) 0.8250(4) 0.0845(16) Uani 1 1 d . . .
H18 H 0.7020 0.5170 0.8598 0.101 Uiso 1 1 calc R . .
C19 C 0.7146(2) 0.2457(9) 0.8476(5) 0.086(2) Uani 1 1 d . . .
H19 H 0.7472 0.2390 0.8972 0.104 Uiso 1 1 calc R . .
C20 C 0.69401(15) 0.0932(8) 0.7987(4) 0.0818(16) Uani 1 1 d . . .
H20 H 0.7119 -0.0196 0.8154 0.098 Uiso 1 1 calc R . .
C21 C 0.64647(14) 0.1020(6) 0.7240(3) 0.0676(13) Uani 1 1 d . . .
H21 H 0.6330 -0.0048 0.6900 0.081 Uiso 1 1 calc R . .
C22 C 0.56526(16) 0.2723(5) 0.6220(4) 0.0419(10) Uani 1 1 d . . .
C23 C 0.56304(17) 0.2289(5) 0.5264(4) 0.0447(11) Uani 1 1 d . . .
C24 C 0.51200(18) 0.2300(5) 0.4609(4) 0.0450(11) Uani 1 1 d . . .
C25 C 0.47185(13) 0.3126(5) 0.5838(3) 0.0460(9) Uani 1 1 d . . .
C26 C 0.41879(13) 0.3431(5) 0.5891(3) 0.0547(10) Uani 1 1 d . . .
H26 H 0.4081 0.3752 0.6420 0.066 Uiso 1 1 calc R . .
C27 C 0.38526(13) 0.3152(5) 0.4980(3) 0.0555(11) Uani 1 1 d . . .
C28 C 0.32343(13) 0.3259(6) 0.4635(4) 0.0807(15) Uani 1 1 d . . .
H28A H 0.3113 0.3107 0.3962 0.121 Uiso 1 1 calc R . .
H28B H 0.3115 0.4442 0.4798 0.121 Uiso 1 1 calc R . .
H28C H 0.3079 0.2296 0.4925 0.121 Uiso 1 1 calc R . .
C29 C 0.50175(17) 0.1912(6) 0.3590(3) 0.0643(12) Uani 1 1 d . . .
H29A H 0.4871 0.0685 0.3452 0.096 Uiso 1 1 calc R . .
H29B H 0.5359 0.2010 0.3431 0.096 Uiso 1 1 calc R . .
H29C H 0.4756 0.2792 0.3226 0.096 Uiso 1 1 calc R . .
C30 C 0.61490(14) 0.1909(6) 0.4981(3) 0.0594(11) Uani 1 1 d . . .
H30A H 0.6228 0.0608 0.5032 0.089 Uiso 1 1 calc R . .
H30B H 0.6454 0.2578 0.5390 0.089 Uiso 1 1 calc R . .
H30C H 0.6094 0.2301 0.4340 0.089 Uiso 1 1 calc R . .
N1 N 1.08530(13) 0.2316(4) 0.0218(3) 0.0519(11) Uani 1 1 d . . .
N2 N 1.03183(13) 0.2329(4) 0.0238(3) 0.0457(10) Uani 1 1 d . . .
N3 N 0.97591(11) 0.1863(4) 0.1279(2) 0.0515(9) Uani 1 1 d . . .
N4 N 0.41373(13) 0.2700(4) 0.4372(3) 0.0558(12) Uani 1 1 d . . .
N5 N 0.46777(13) 0.2673(4) 0.4921(3) 0.0438(10) Uani 1 1 d . . .
N6 N 0.52183(10) 0.3183(4) 0.6501(2) 0.0504(9) Uani 1 1 d . . .






_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 C6 1.381(5) . ?
C1 C2 1.387(6) . ?
C1 C7 1.503(7) . ?
C2 C3 1.382(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N3 1.330(5) . ?
C7 C8 1.410(7) . ?
C8 C9 1.370(7) . ?
C8 C15 1.513(6) . ?
C9 N2 1.386(6) . ?
C9 C14 1.485(7) . ?
C10 N3 1.354(4) . ?
C10 N2 1.387(6) . ?
C10 C11 1.389(4) . ?
C11 C12 1.375(5) . ?
C11 H11 0.9300 . ?
C12 N1 1.346(6) . ?
C12 C13 1.508(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.377(6) . ?
C16 C21 1.384(6) . ?
C16 C22 1.483(6) . ?
C17 C18 1.393(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.337(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 N6 1.324(5) . ?
C22 C23 1.435(7) . ?
C23 C24 1.368(6) . ?
C23 C30 1.513(6) . ?
C24 N5 1.355(6) . ?
C24 C29 1.482(6) . ?
C25 N6 1.354(4) . ?
C25 N5 1.371(6) . ?
C25 C26 1.383(5) . ?
C26 C27 1.382(5) . ?
C26 H26 0.9300 . ?
C27 N4 1.345(6) . ?
C27 C28 1.497(4) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
N1 N2 1.359(5) . ?
N4 N5 1.369(4) . ?



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






















































































































C6 C1 C2 119.6(5) . . ?
C6 C1 C7 120.5(4) . . ?
C2 C1 C7 119.9(4) . . ?
C3 C2 C1 119.5(5) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 121.3(6) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.2(6) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 120.5(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.8(5) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
N3 C7 C8 123.4(5) . . ?
N3 C7 C1 113.4(5) . . ?
C8 C7 C1 123.2(5) . . ?
C9 C8 C7 120.2(5) . . ?
C9 C8 C15 117.9(5) . . ?
C7 C8 C15 121.9(5) . . ?
C8 C9 N2 116.1(5) . . ?
C8 C9 C14 128.3(5) . . ?
N2 C9 C14 115.7(4) . . ?
N3 C10 N2 122.1(3) . . ?
N3 C10 C11 133.7(4) . . ?
N2 C10 C11 104.2(3) . . ?
C12 C11 C10 106.3(4) . . ?
C12 C11 H11 126.8 . . ?
C10 C11 H11 126.8 . . ?
N1 C12 C11 113.1(3) . . ?
N1 C12 C13 117.5(4) . . ?
C11 C12 C13 129.4(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 118.2(4) . . ?
C17 C16 C22 121.3(4) . . ?
C21 C16 C22 120.4(4) . . ?
C16 C17 C18 119.9(5) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 120.2(5) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 120.2(5) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.5(5) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 121.0(5) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
N6 C22 C23 124.6(4) . . ?
N6 C22 C16 114.5(4) . . ?
C23 C22 C16 121.0(5) . . ?
C24 C23 C22 117.1(5) . . ?
C24 C23 C30 121.2(5) . . ?
C22 C23 C30 121.7(4) . . ?
N5 C24 C23 117.4(5) . . ?
N5 C24 C29 118.0(4) . . ?
C23 C24 C29 124.7(5) . . ?
N6 C25 N5 120.6(3) . . ?
N6 C25 C26 131.9(4) . . ?
N5 C25 C26 107.5(3) . . ?
C27 C26 C25 104.4(3) . . ?
C27 C26 H26 127.8 . . ?
C25 C26 H26 127.8 . . ?
N4 C27 C26 113.2(3) . . ?
N4 C27 C28 119.6(4) . . ?
C26 C27 C28 127.3(4) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C24 C29 H29A 109.5 . . ?
C24 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C24 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C23 C30 H30A 109.5 . . ?
C23 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C23 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C12 N1 N2 102.9(4) . . ?
N1 N2 C9 125.1(5) . . ?
N1 N2 C10 113.4(4) . . ?
C9 N2 C10 121.5(4) . . ?
C7 N3 C10 116.7(4) . . ?
C27 N4 N5 104.0(4) . . ?
C24 N5 N4 125.4(5) . . ?
C24 N5 C25 123.7(4) . . ?
N4 N5 C25 110.9(4) . . ?
C22 N6 C25 116.6(3) . . ?



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
















































































C6 C1 C2 C3 0.7(7) . . . . ?
C7 C1 C2 C3 177.7(5) . . . . ?
C1 C2 C3 C4 -1.7(8) . . . . ?
C2 C3 C4 C5 1.8(9) . . . . ?
C3 C4 C5 C6 -0.9(9) . . . . ?
C2 C1 C6 C5 0.1(7) . . . . ?
C7 C1 C6 C5 -176.9(5) . . . . ?
C4 C5 C6 C1 0.0(8) . . . . ?
C6 C1 C7 N3 117.3(5) . . . . ?
C2 C1 C7 N3 -59.7(6) . . . . ?
C6 C1 C7 C8 -62.3(6) . . . . ?
C2 C1 C7 C8 120.7(5) . . . . ?
N3 C7 C8 C9 -1.7(6) . . . . ?
C1 C7 C8 C9 177.9(3) . . . . ?
N3 C7 C8 C15 175.7(4) . . . . ?
C1 C7 C8 C15 -4.7(5) . . . . ?
C7 C8 C9 N2 -0.9(5) . . . . ?
C15 C8 C9 N2 -178.4(3) . . . . ?
C7 C8 C9 C14 179.5(4) . . . . ?
C15 C8 C9 C14 2.0(6) . . . . ?
N3 C10 C11 C12 -178.6(4) . . . . ?
N2 C10 C11 C12 0.5(4) . . . . ?
C10 C11 C12 N1 -0.6(5) . . . . ?
C10 C11 C12 C13 179.1(4) . . . . ?
C21 C16 C17 C18 0.2(7) . . . . ?
C22 C16 C17 C18 176.2(5) . . . . ?
C16 C17 C18 C19 0.2(8) . . . . ?
C17 C18 C19 C20 -1.0(10) . . . . ?
C18 C19 C20 C21 1.4(9) . . . . ?
C19 C20 C21 C16 -1.0(8) . . . . ?
C17 C16 C21 C20 0.2(7) . . . . ?
C22 C16 C21 C20 -175.9(5) . . . . ?
C17 C16 C22 N6 -61.3(6) . . . . ?
C21 C16 C22 N6 114.6(5) . . . . ?
C17 C16 C22 C23 118.9(5) . . . . ?
C21 C16 C22 C23 -65.2(6) . . . . ?
N6 C22 C23 C24 -2.2(5) . . . . ?
C16 C22 C23 C24 177.6(3) . . . . ?
N6 C22 C23 C30 175.5(4) . . . . ?
C16 C22 C23 C30 -4.7(5) . . . . ?
C22 C23 C24 N5 -1.6(5) . . . . ?
C30 C23 C24 N5 -179.3(3) . . . . ?
C22 C23 C24 C29 179.2(4) . . . . ?
C30 C23 C24 C29 1.5(6) . . . . ?
N6 C25 C26 C27 -179.5(4) . . . . ?
N5 C25 C26 C27 -0.5(4) . . . . ?
C25 C26 C27 N4 0.0(5) . . . . ?
C25 C26 C27 C28 178.5(4) . . . . ?
C11 C12 N1 N2 0.4(4) . . . . ?
C13 C12 N1 N2 -179.3(3) . . . . ?
C12 N1 N2 C9 179.9(3) . . . . ?
C12 N1 N2 C10 -0.1(4) . . . . ?
C8 C9 N2 N1 -177.8(3) . . . . ?
C14 C9 N2 N1 1.9(5) . . . . ?
C8 C9 N2 C10 2.2(5) . . . . ?
C14 C9 N2 C10 -178.2(3) . . . . ?
N3 C10 N2 N1 179.0(3) . . . . ?
C11 C10 N2 N1 -0.3(4) . . . . ?
N3 C10 N2 C9 -1.0(6) . . . . ?
C11 C10 N2 C9 179.7(3) . . . . ?
C8 C7 N3 C10 2.8(6) . . . . ?
C1 C7 N3 C10 -176.8(3) . . . . ?
N2 C10 N3 C7 -1.5(6) . . . . ?
C11 C10 N3 C7 177.5(4) . . . . ?
C26 C27 N4 N5 0.6(4) . . . . ?
C28 C27 N4 N5 -178.1(3) . . . . ?
C23 C24 N5 N4 -178.4(3) . . . . ?
C29 C24 N5 N4 0.9(5) . . . . ?
C23 C24 N5 C25 3.4(5) . . . . ?
C29 C24 N5 C25 -177.3(3) . . . . ?
C27 N4 N5 C24 -179.3(3) . . . . ?
C27 N4 N5 C25 -0.9(4) . . . . ?
N6 C25 N5 C24 -1.5(6) . . . . ?
C26 C25 N5 C24 179.3(3) . . . . ?
N6 C25 N5 N4 -180.0(3) . . . . ?
C26 C25 N5 N4 0.9(4) . . . . ?
C23 C22 N6 C25 4.1(6) . . . . ?
C16 C22 N6 C25 -175.7(3) . . . . ?
N5 C25 N6 C22 -2.2(5) . . . . ?
C26 C25 N6 C22 176.7(4) . . . . ?



_diffrn_measured_fraction_theta_max 0.986

_diffrn_reflns_theta_full        25.50

_diffrn_measured_fraction_theta_full 0.986

_refine_diff_density_max         0.141

_refine_diff_density_min         -0.159

_refine_diff_density_rms         0.033

_database_code_depnum_ccdc_archive 'CCDC 975574'
#######################################################################
#
#                 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_ddd


_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C15 H15 N3'

_chemical_formula_weight         237.30



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)/n



loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   5.784(3)

_cell_length_b                   16.411(9)

_cell_length_c                   13.211(7)

_cell_angle_alpha                90.00

_cell_angle_beta                 92.703(7)

_cell_angle_gamma                90.00

_cell_volume                     1252.6(12)

_cell_formula_units_Z            4

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    1039

_cell_measurement_theta_min      2.48

_cell_measurement_theta_max      22.06



_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.39

_exptl_crystal_size_mid          0.11

_exptl_crystal_size_min          0.09

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.258

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             504

_exptl_absorpt_coefficient_mu    0.077

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9706

_exptl_absorpt_correction_T_max  0.9931

_exptl_absorpt_process_details   sadabs



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      296(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  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            7574

_diffrn_reflns_av_R_equivalents  0.0495

_diffrn_reflns_av_sigmaI/netI    0.0493

_diffrn_reflns_limit_h_min       -6

_diffrn_reflns_limit_h_max       6

_diffrn_reflns_limit_k_min       -19

_diffrn_reflns_limit_k_max       19

_diffrn_reflns_limit_l_min       -15

_diffrn_reflns_limit_l_max       15

_diffrn_reflns_theta_min         2.48

_diffrn_reflns_theta_max         25.50

_reflns_number_total             2284

_reflns_number_gt                1554

_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.

;



_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)+(0.0547P)²+0.1324P] 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_number_reflns         2284

_refine_ls_number_parameters     165

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0804

_refine_ls_R_factor_gt           0.0484

_refine_ls_wR_factor_ref         0.1257

_refine_ls_wR_factor_gt          0.1084

_refine_ls_goodness_of_fit_ref   1.033

_refine_ls_restrained_S_all      1.033

_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




































C1 C -0.1257(3) 0.66005(12) 0.82721(16) 0.0413(5) Uani 1 1 d . . .
C2 C -0.0591(4) 0.59791(12) 0.89351(16) 0.0462(6) Uani 1 1 d . . .
H2 H -0.1291 0.5472 0.8997 0.055 Uiso 1 1 calc R . .
C3 C 0.1321(3) 0.62687(12) 0.94823(15) 0.0388(5) Uani 1 1 d . . .
C4 C 0.4494(4) 0.63745(13) 1.05770(15) 0.0423(5) Uani 1 1 d . . .
C5 C 0.4914(3) 0.71958(12) 1.02619(14) 0.0369(5) Uani 1 1 d . . .
C6 C 0.3463(3) 0.75373(11) 0.95263(14) 0.0337(5) Uani 1 1 d . . .
C7 C 0.3612(3) 0.83875(11) 0.91391(15) 0.0354(5) Uani 1 1 d . . .
C8 C 0.5508(3) 0.86441(13) 0.86131(16) 0.0454(6) Uani 1 1 d . . .
H8 H 0.6700 0.8281 0.8493 0.054 Uiso 1 1 calc R . .
C9 C 0.5624(4) 0.94390(13) 0.82687(17) 0.0513(6) Uani 1 1 d . . .
H9 H 0.6885 0.9604 0.7909 0.062 Uiso 1 1 calc R . .
C10 C 0.3896(4) 0.99861(13) 0.84519(17) 0.0494(6) Uani 1 1 d . . .
H10 H 0.3989 1.0520 0.8221 0.059 Uiso 1 1 calc R . .
C11 C 0.2022(4) 0.97375(13) 0.89812(16) 0.0496(6) Uani 1 1 d . . .
H11 H 0.0856 1.0107 0.9115 0.060 Uiso 1 1 calc R . .
C12 C 0.1873(3) 0.89422(12) 0.93132(16) 0.0437(5) Uani 1 1 d . . .
H12 H 0.0588 0.8777 0.9658 0.052 Uiso 1 1 calc R . .
C13 C -0.3217(4) 0.66073(14) 0.74917(18) 0.0571(6) Uani 1 1 d . . .
H13A H -0.3250 0.7121 0.7144 0.086 Uiso 0.50 1 calc PR . .
H13B H -0.4650 0.6529 0.7816 0.086 Uiso 0.50 1 calc PR . .
H13C H -0.3008 0.6176 0.7014 0.086 Uiso 0.50 1 calc PR . .
H13D H -0.4022 0.6096 0.7505 0.086 Uiso 0.50 1 calc PR . .
H13E H -0.2622 0.6689 0.6833 0.086 Uiso 0.50 1 calc PR . .
H13F H -0.4264 0.7041 0.7636 0.086 Uiso 0.50 1 calc PR . .
C14 C 0.6061(4) 0.59786(14) 1.13674(17) 0.0595(7) Uani 1 1 d . . .
H14A H 0.5620 0.5419 1.1444 0.089 Uiso 1 1 calc R . .
H14B H 0.5937 0.6258 1.2001 0.089 Uiso 1 1 calc R . .
H14C H 0.7630 0.6006 1.1163 0.089 Uiso 1 1 calc R . .
C15 C 0.6893(4) 0.76701(14) 1.07616(16) 0.0493(6) Uani 1 1 d . . .
H15A H 0.6801 0.8229 1.0547 0.074 Uiso 1 1 calc R . .
H15B H 0.8335 0.7441 1.0571 0.074 Uiso 1 1 calc R . .
H15C H 0.6799 0.7643 1.1484 0.074 Uiso 1 1 calc R . .
N1 N 0.2741(3) 0.59297(10) 1.02138(13) 0.0458(5) Uani 1 1 d . . .
N2 N 0.1685(3) 0.70523(9) 0.91328(12) 0.0350(4) Uani 1 1 d . . .
N3 N 0.0110(3) 0.72670(10) 0.83767(12) 0.0396(4) Uani 1 1 d . . .






_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 N3 1.353(2) . ?
C1 C2 1.387(3) . ?
C1 C13 1.496(3) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 N1 1.358(2) . ?
C3 N2 1.386(2) . ?
C4 N1 1.321(3) . ?
C4 C5 1.435(3) . ?
C4 C14 1.498(3) . ?
C5 C6 1.373(3) . ?
C5 C15 1.510(3) . ?
C6 N2 1.382(2) . ?
C6 C7 1.490(3) . ?
C7 C12 1.384(3) . ?
C7 C8 1.391(3) . ?
C8 C9 1.384(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 H13D 0.9600 . ?
C13 H13E 0.9600 . ?
C13 H13F 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N2 N3 1.366(2) . ?



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










































































N3 C1 C2 112.73(18) . . ?
N3 C1 C13 118.99(18) . . ?
C2 C1 C13 128.29(19) . . ?
C3 C2 C1 105.67(18) . . ?
C3 C2 H2 127.2 . . ?
C1 C2 H2 127.2 . . ?
N1 C3 C2 132.55(19) . . ?
N1 C3 N2 121.42(17) . . ?
C2 C3 N2 106.03(17) . . ?
N1 C4 C5 123.46(18) . . ?
N1 C4 C14 116.25(19) . . ?
C5 C4 C14 120.29(19) . . ?
C6 C5 C4 118.86(17) . . ?
C6 C5 C15 121.61(18) . . ?
C4 C5 C15 119.52(17) . . ?
C5 C6 N2 116.75(17) . . ?
C5 C6 C7 125.58(17) . . ?
N2 C6 C7 117.66(16) . . ?
C12 C7 C8 118.71(19) . . ?
C12 C7 C6 120.29(18) . . ?
C8 C7 C6 120.99(18) . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.5(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C13 H13D 109.5 . . ?
H13A C13 H13D 141.1 . . ?
H13B C13 H13D 56.3 . . ?
H13C C13 H13D 56.3 . . ?
C1 C13 H13E 109.5 . . ?
H13A C13 H13E 56.3 . . ?
H13B C13 H13E 141.1 . . ?
H13C C13 H13E 56.3 . . ?
H13D C13 H13E 109.5 . . ?
C1 C13 H13F 109.5 . . ?
H13A C13 H13F 56.3 . . ?
H13B C13 H13F 56.3 . . ?
H13C C13 H13F 141.1 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 N1 C3 117.41(18) . . ?
N3 N2 C6 125.82(16) . . ?
N3 N2 C3 112.12(15) . . ?
C6 N2 C3 122.06(16) . . ?
C1 N3 N2 103.45(15) . . ?



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








































N3 C1 C2 C3 -0.6(2) . . . . ?
C13 C1 C2 C3 179.0(2) . . . . ?
C1 C2 C3 N1 -178.0(2) . . . . ?
C1 C2 C3 N2 0.9(2) . . . . ?
N1 C4 C5 C6 -1.7(3) . . . . ?
C14 C4 C5 C6 179.14(19) . . . . ?
N1 C4 C5 C15 176.81(19) . . . . ?
C14 C4 C5 C15 -2.4(3) . . . . ?
C4 C5 C6 N2 -0.5(3) . . . . ?
C15 C5 C6 N2 -178.92(17) . . . . ?
C4 C5 C6 C7 177.93(18) . . . . ?
C15 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C12 -113.7(2) . . . . ?
N2 C6 C7 C12 64.7(2) . . . . ?
C5 C6 C7 C8 65.2(3) . . . . ?
N2 C6 C7 C8 -116.4(2) . . . . ?
C12 C7 C8 C9 -0.4(3) . . . . ?
C6 C7 C8 C9 -179.35(19) . . . . ?
C7 C8 C9 C10 0.9(3) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C7 1.3(3) . . . . ?
C8 C7 C12 C11 -0.7(3) . . . . ?
C6 C7 C12 C11 178.27(18) . . . . ?
C5 C4 N1 C3 2.0(3) . . . . ?
C14 C4 N1 C3 -178.74(19) . . . . ?
C2 C3 N1 C4 178.5(2) . . . . ?
N2 C3 N1 C4 -0.3(3) . . . . ?
C5 C6 N2 N3 -177.74(16) . . . . ?
C7 C6 N2 N3 3.7(3) . . . . ?
C5 C6 N2 C3 2.1(3) . . . . ?
C7 C6 N2 C3 -176.40(17) . . . . ?
N1 C3 N2 N3 178.07(17) . . . . ?
C2 C3 N2 N3 -1.0(2) . . . . ?
N1 C3 N2 C6 -1.8(3) . . . . ?
C2 C3 N2 C6 179.11(17) . . . . ?
C2 C1 N3 N2 0.0(2) . . . . ?
C13 C1 N3 N2 -179.67(17) . . . . ?
C6 N2 N3 C1 -179.51(17) . . . . ?
C3 N2 N3 C1 0.6(2) . . . . ?



_diffrn_measured_fraction_theta_max 0.985

_diffrn_reflns_theta_full        25.50

_diffrn_measured_fraction_theta_full 0.985

_refine_diff_density_max         0.161

_refine_diff_density_min         -0.165

_refine_diff_density_rms         0.039

_database_code_depnum_ccdc_archive 'CCDC 975575'
