# Electronic Supplementary Material (ESI) for ChemComm.
# 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 N2'
_chemical_formula_weight         270.32

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   P21/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                   12.2021(6)
_cell_length_b                   11.4270(6)
_cell_length_c                   10.8496(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.451(2)
_cell_angle_gamma                90.00
_cell_volume                     1492.26(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5752
_cell_measurement_theta_min      2.329
_cell_measurement_theta_max      26.289

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9536
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13606
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2618
_reflns_number_gt                2059
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


_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)+(0.0456P)²+0.3154P] 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       0.0109(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2618
_refine_ls_number_parameters     191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.75591(11) 0.35331(12) 0.98915(14) 0.0493(4) Uani 1 1 d . . .
C2 C 0.76021(13) 0.45114(13) 0.91445(15) 0.0580(4) Uani 1 1 d . . .
H2 H 0.7194 0.4523 0.8342 0.070 Uiso 1 1 calc R . .
C3 C 0.82369(13) 0.54609(13) 0.95715(16) 0.0596(4) Uani 1 1 d . . .
H3 H 0.8251 0.6113 0.9062 0.072 Uiso 1 1 calc R . .
C4 C 0.88575(11) 0.54535(12) 1.07582(15) 0.0538(4) Uani 1 1 d . . .
C5 C 0.88391(13) 0.44708(13) 1.14943(15) 0.0580(4) Uani 1 1 d . . .
H5 H 0.9268 0.4451 1.2286 0.070 Uiso 1 1 calc R . .
C6 C 0.81961(12) 0.35223(13) 1.10731(15) 0.0560(4) Uani 1 1 d . . .
H6 H 0.8188 0.2869 1.1583 0.067 Uiso 1 1 calc R . .
C7 C 0.95089(13) 0.64538(14) 1.12080(17) 0.0646(4) Uani 1 1 d . . .
C8 C 0.71531(11) 0.14311(12) 0.99194(14) 0.0495(4) Uani 1 1 d . . .
C9 C 0.81946(13) 0.09690(14) 0.99109(17) 0.0658(5) Uani 1 1 d . . .
H9 H 0.8726 0.1402 0.9586 0.079 Uiso 1 1 calc R . .
C10 C 0.84481(15) -0.01365(15) 1.03854(19) 0.0720(5) Uani 1 1 d . . .
H10 H 0.9158 -0.0437 1.0395 0.086 Uiso 1 1 calc R . .
C11 C 0.76711(15) -0.07935(14) 1.08397(16) 0.0647(4) Uani 1 1 d . . .
H11 H 0.7845 -0.1542 1.1148 0.078 Uiso 1 1 calc R . .
C12 C 0.66390(14) -0.03423(14) 1.08371(15) 0.0621(4) Uani 1 1 d . . .
H12 H 0.6105 -0.0790 1.1140 0.075 Uiso 1 1 calc R . .
C13 C 0.63736(12) 0.07690(14) 1.03913(14) 0.0549(4) Uani 1 1 d . . .
H13 H 0.5669 0.1072 1.0409 0.066 Uiso 1 1 calc R . .
C14 C 0.58426(12) 0.27695(12) 0.86834(13) 0.0486(4) Uani 1 1 d . . .
C15 C 0.54894(14) 0.20685(16) 0.76664(15) 0.0656(5) Uani 1 1 d . . .
H15 H 0.5944 0.1473 0.7456 0.079 Uiso 1 1 calc R . .
C16 C 0.44503(17) 0.2255(2) 0.69541(16) 0.0806(6) Uani 1 1 d U . .
H16 H 0.4212 0.1782 0.6264 0.097 Uiso 1 1 calc R . .
C17 C 0.37734(16) 0.3125(2) 0.72555(19) 0.0803(6) Uani 1 1 d U . .
H17 H 0.3077 0.3243 0.6776 0.096 Uiso 1 1 calc R . .
C18 C 0.41247(15) 0.38152(17) 0.8258(2) 0.0788(6) Uani 1 1 d . . .
H18 H 0.3669 0.4411 0.8465 0.095 Uiso 1 1 calc R . .
C19 C 0.51494(13) 0.36398(14) 0.89689(17) 0.0642(4) Uani 1 1 d . . .
H19 H 0.5379 0.4118 0.9656 0.077 Uiso 1 1 calc R . .
N1 N 0.68891(10) 0.25781(10) 0.94459(13) 0.0578(4) Uani 1 1 d . . .
N2 N 1.00114(14) 0.72622(14) 1.15660(18) 0.0893(5) 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 0.0448(7) 0.0394(7) 0.0601(9) 0.0012(6) -0.0019(6) 0.0003(6)
C2 0.0604(9) 0.0501(9) 0.0575(9) 0.0066(7) -0.0084(7) -0.0039(7)
C3 0.0595(9) 0.0445(8) 0.0713(10) 0.0118(7) 0.0000(8) -0.0038(7)
C4 0.0454(8) 0.0417(8) 0.0710(10) -0.0009(7) 0.0000(7) -0.0018(6)
C5 0.0564(9) 0.0517(9) 0.0596(9) 0.0017(7) -0.0092(7) -0.0035(7)
C6 0.0567(9) 0.0442(8) 0.0622(9) 0.0099(7) -0.0044(7) -0.0036(7)
C7 0.0576(9) 0.0481(9) 0.0840(12) -0.0007(8) -0.0009(8) -0.0038(8)
C8 0.0483(8) 0.0391(7) 0.0579(9) -0.0025(6) -0.0001(6) -0.0027(6)
C9 0.0526(9) 0.0507(9) 0.0958(13) 0.0102(9) 0.0170(8) -0.0001(7)
C10 0.0592(10) 0.0531(9) 0.1032(14) 0.0073(9) 0.0116(9) 0.0101(8)
C11 0.0755(11) 0.0453(8) 0.0683(10) 0.0078(8) -0.0029(8) -0.0004(8)
C12 0.0666(10) 0.0583(10) 0.0593(10) 0.0099(8) 0.0044(8) -0.0139(8)
C13 0.0469(8) 0.0570(9) 0.0593(9) -0.0024(7) 0.0042(7) -0.0022(7)
C14 0.0478(8) 0.0441(8) 0.0510(8) 0.0035(6) -0.0005(6) -0.0054(6)
C15 0.0631(10) 0.0743(11) 0.0599(10) -0.0132(9) 0.0109(8) -0.0135(8)
C16 0.0765(13) 0.1149(16) 0.0461(9) -0.0038(10) -0.0024(9) -0.0371(12)
C17 0.0587(11) 0.0999(15) 0.0750(12) 0.0363(12) -0.0109(9) -0.0125(11)
C18 0.0572(10) 0.0679(11) 0.1055(15) 0.0165(11) -0.0043(10) 0.0060(9)
C19 0.0609(10) 0.0541(9) 0.0728(11) -0.0040(8) -0.0034(8) 0.0035(8)
N1 0.0512(7) 0.0382(6) 0.0766(9) 0.0013(6) -0.0112(6) -0.0026(5)
N2 0.0858(11) 0.0595(9) 0.1146(13) -0.0076(9) -0.0073(9) -0.0200(8)

_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 1.386(2) . ?
C1 C2 1.387(2) . ?
C1 N1 1.4012(18) . ?
C2 C3 1.369(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(2) . ?
C4 C7 1.431(2) . ?
C5 C6 1.372(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.141(2) . ?
C8 C9 1.378(2) . ?
C8 C13 1.378(2) . ?
C8 N1 1.4253(18) . ?
C9 C10 1.380(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.360(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.374(2) . ?
C14 C15 1.374(2) . ?
C14 N1 1.4198(18) . ?
C15 C16 1.389(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.367(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.354(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

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 118.60(13) . . ?
C6 C1 N1 121.27(13) . . ?
C2 C1 N1 120.14(13) . . ?
C3 C2 C1 120.97(14) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.22(14) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.04(13) . . ?
C5 C4 C7 120.88(14) . . ?
C3 C4 C7 120.08(14) . . ?
C6 C5 C4 120.85(14) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 120.29(14) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
N2 C7 C4 178.79(19) . . ?
C9 C8 C13 119.07(14) . . ?
C9 C8 N1 120.28(13) . . ?
C13 C8 N1 120.65(13) . . ?
C8 C9 C10 119.92(15) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.82(16) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 119.28(15) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 120.93(15) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C12 119.96(14) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C19 C14 C15 118.65(14) . . ?
C19 C14 N1 120.55(13) . . ?
C15 C14 N1 120.77(14) . . ?
C14 C15 C16 119.66(17) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.72(17) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 119.46(17) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.37(19) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 121.13(17) . . ?
C18 C19 H19 119.4 . . ?
C14 C19 H19 119.4 . . ?
C1 N1 C14 119.94(11) . . ?
C1 N1 C8 120.49(11) . . ?
C14 N1 C8 118.69(11) . . ?

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 -1.6(2) . . . . ?
N1 C1 C2 C3 178.86(14) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
C2 C3 C4 C7 -179.18(15) . . . . ?
C3 C4 C5 C6 -1.6(2) . . . . ?
C7 C4 C5 C6 178.59(15) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C2 C1 C6 C5 1.0(2) . . . . ?
N1 C1 C6 C5 -179.46(14) . . . . ?
C5 C4 C7 N2 -114(10) . . . . ?
C3 C4 C7 N2 66(10) . . . . ?
C13 C8 C9 C10 -0.8(3) . . . . ?
N1 C8 C9 C10 179.18(16) . . . . ?
C8 C9 C10 C11 1.5(3) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C9 C8 C13 C12 -0.5(2) . . . . ?
N1 C8 C13 C12 179.51(14) . . . . ?
C11 C12 C13 C8 1.2(2) . . . . ?
C19 C14 C15 C16 0.1(2) . . . . ?
N1 C14 C15 C16 178.35(15) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C17 C18 C19 C14 0.2(3) . . . . ?
C15 C14 C19 C18 -0.2(2) . . . . ?
N1 C14 C19 C18 -178.38(16) . . . . ?
C6 C1 N1 C14 143.51(15) . . . . ?
C2 C1 N1 C14 -37.0(2) . . . . ?
C6 C1 N1 C8 -25.6(2) . . . . ?
C2 C1 N1 C8 153.89(15) . . . . ?
C19 C14 N1 C1 -42.6(2) . . . . ?
C15 C14 N1 C1 139.23(16) . . . . ?
C19 C14 N1 C8 126.73(16) . . . . ?
C15 C14 N1 C8 -51.5(2) . . . . ?
C9 C8 N1 C1 -53.6(2) . . . . ?
C13 C8 N1 C1 126.40(16) . . . . ?
C9 C8 N1 C14 137.15(16) . . . . ?
C13 C8 N1 C14 -42.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.028
_database_code_depnum_ccdc_archive 'CCDC 963776'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H12 N4'
_chemical_formula_sum            'C21 H12 N4'
_chemical_formula_weight         320.35

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           ORTHORHOMBIC
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   8.1650(4)
_cell_length_b                   11.6360(5)
_cell_length_c                   17.5650(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1668.81(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2883
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      26.6

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9632
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7581
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1466
_reflns_number_gt                1164
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


_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)+(0.0442P)²+0.2539P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0171(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1466
_refine_ls_number_parameters     117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 -0.05770(15) 0.07647(10) 0.68481(7) 0.0413(3) Uani 1 1 d . . .
C2 C 0.00332(16) -0.03104(9) 0.66495(7) 0.0457(3) Uani 1 1 d . . .
H2 H 0.0872 -0.0636 0.6936 0.055 Uiso 1 1 calc R . .
C3 C -0.05892(16) -0.08968(10) 0.60350(7) 0.0482(4) Uani 1 1 d . . .
H3 H -0.0183 -0.1621 0.5913 0.058 Uiso 1 1 calc R . .
C4 C -0.18192(17) -0.04141(11) 0.55960(7) 0.0476(4) Uani 1 1 d . . .
C5 C -0.23938(17) 0.06768(11) 0.57739(8) 0.0518(4) Uani 1 1 d . . .
H5 H -0.3197 0.1016 0.5473 0.062 Uiso 1 1 calc R . .
C6 C -0.17810(16) 0.12562(10) 0.63921(7) 0.0476(3) Uani 1 1 d . . .
H6 H -0.2175 0.1986 0.6507 0.057 Uiso 1 1 calc R . .
C7 C 0.0000 0.25785(13) 0.7500 0.0421(4) Uani 1 2 d S . .
C8 C -0.06581(17) 0.31740(11) 0.81079(8) 0.0515(4) Uani 1 1 d . . .
H8 H -0.1116 0.2775 0.8515 0.062 Uiso 1 1 calc R . .
C9 C -0.06362(17) 0.43565(11) 0.81121(8) 0.0558(4) Uani 1 1 d . . .
H9 H -0.1051 0.4756 0.8528 0.067 Uiso 1 1 calc R . .
C10 C 0.0000 0.49495(14) 0.7500 0.0527(5) Uani 1 2 d S . .
C11 C 0.0000 0.61867(16) 0.7500 0.0706(7) Uani 1 2 d S . .
C12 C -0.2532(2) -0.10495(12) 0.49799(9) 0.0611(4) Uani 1 1 d . . .
N1 N 0.0000 0.13548(11) 0.7500 0.0461(4) Uani 1 2 d S . .
N3 N 0.0000 0.71619(15) 0.7500 0.1007(9) Uani 1 2 d S . .
N4 N -0.3132(2) -0.15614(12) 0.45011(8) 0.0886(5) 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 0.0473(7) 0.0303(6) 0.0461(7) 0.0018(5) 0.0010(6) -0.0028(5)
C2 0.0503(7) 0.0344(6) 0.0524(8) -0.0001(6) -0.0054(6) 0.0046(5)
C3 0.0601(8) 0.0336(6) 0.0509(8) -0.0038(6) 0.0037(7) 0.0015(6)
C4 0.0564(8) 0.0424(7) 0.0439(7) 0.0014(6) -0.0007(6) -0.0075(6)
C5 0.0550(8) 0.0462(8) 0.0542(8) 0.0059(6) -0.0097(7) 0.0007(6)
C6 0.0518(7) 0.0349(7) 0.0561(8) 0.0007(6) -0.0028(7) 0.0048(5)
C7 0.0475(10) 0.0276(8) 0.0512(11) 0.000 -0.0032(8) 0.000
C8 0.0606(8) 0.0384(7) 0.0554(8) 0.0002(6) 0.0047(7) 0.0006(6)
C9 0.0656(9) 0.0382(7) 0.0637(9) -0.0105(6) -0.0041(7) 0.0082(6)
C10 0.0601(12) 0.0292(9) 0.0688(13) 0.000 -0.0208(10) 0.000
C11 0.0944(17) 0.0351(11) 0.0824(16) 0.000 -0.0384(13) 0.000
C12 0.0779(11) 0.0526(8) 0.0528(9) -0.0006(7) -0.0087(8) -0.0070(7)
N1 0.0637(10) 0.0265(7) 0.0480(9) 0.000 -0.0086(7) 0.000
N3 0.162(2) 0.0319(10) 0.1083(17) 0.000 -0.0592(16) 0.000
N4 0.1182(13) 0.0751(10) 0.0724(10) -0.0129(8) -0.0272(9) -0.0105(9)

_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 C2 1.3910(16) . ?
C1 C6 1.3910(17) . ?
C1 N1 1.4159(13) . ?
C2 C3 1.3743(18) . ?
C2 H2 0.9300 . ?
C3 C4 1.3852(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.3889(19) . ?
C4 C12 1.4341(19) . ?
C5 C6 1.3726(18) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.3817(15) 4_556 ?
C7 C8 1.3817(15) . ?
C7 N1 1.424(2) . ?
C8 C9 1.3761(19) . ?
C8 H8 0.9300 . ?
C9 C10 1.3791(16) . ?
C9 H9 0.9300 . ?
C10 C9 1.3790(16) 4_556 ?
C10 C11 1.440(2) . ?
C11 N3 1.135(2) . ?
C12 N4 1.1412(18) . ?
N1 C1 1.4159(13) 4_556 ?

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
C2 C1 C6 118.59(12) . . ?
C2 C1 N1 121.32(11) . . ?
C6 C1 N1 120.09(11) . . ?
C3 C2 C1 120.73(12) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.26(11) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 119.36(12) . . ?
C3 C4 C12 120.35(12) . . ?
C5 C4 C12 120.25(13) . . ?
C6 C5 C4 120.25(13) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.74(12) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C8 C7 C8 119.80(16) 4_556 . ?
C8 C7 N1 120.10(8) 4_556 . ?
C8 C7 N1 120.10(8) . . ?
C9 C8 C7 120.03(13) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.07(14) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C9 119.96(17) 4_556 . ?
C9 C10 C11 120.02(8) 4_556 . ?
C9 C10 C11 120.02(8) . . ?
N3 C11 C10 180.000(1) . . ?
N4 C12 C4 178.29(18) . . ?
C1 N1 C1 121.98(13) . 4_556 ?
C1 N1 C7 119.01(7) . . ?
C1 N1 C7 119.01(7) 4_556 . ?

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 -2.77(19) . . . . ?
N1 C1 C2 C3 177.05(11) . . . . ?
C1 C2 C3 C4 1.1(2) . . . . ?
C2 C3 C4 C5 1.3(2) . . . . ?
C2 C3 C4 C12 -176.60(12) . . . . ?
C3 C4 C5 C6 -1.9(2) . . . . ?
C12 C4 C5 C6 175.99(13) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C2 C1 C6 C5 2.16(19) . . . . ?
N1 C1 C6 C5 -177.67(11) . . . . ?
C8 C7 C8 C9 -0.92(9) 4_556 . . . ?
N1 C7 C8 C9 179.07(9) . . . . ?
C7 C8 C9 C10 1.85(19) . . . . ?
C8 C9 C10 C9 -0.93(9) . . . 4_556 ?
C8 C9 C10 C11 179.07(9) . . . . ?
C9 C10 C11 N3 0(81) 4_556 . . . ?
C9 C10 C11 N3 0(76) . . . . ?
C3 C4 C12 N4 101(6) . . . . ?
C5 C4 C12 N4 -77(6) . . . . ?
C2 C1 N1 C1 -29.96(9) . . . 4_556 ?
C6 C1 N1 C1 149.86(13) . . . 4_556 ?
C2 C1 N1 C7 150.04(9) . . . . ?
C6 C1 N1 C7 -30.14(13) . . . . ?
C8 C7 N1 C1 -49.08(9) 4_556 . . . ?
C8 C7 N1 C1 130.92(9) . . . . ?
C8 C7 N1 C1 130.92(9) 4_556 . . 4_556 ?
C8 C7 N1 C1 -49.08(9) . . . 4_556 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 963777'
