# 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_1aL
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H24 N4'
_chemical_formula_iupac          ?
_chemical_formula_weight         512.59

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0514(11)
_cell_length_b                   12.8065(11)
_cell_length_c                   12.8890(15)
_cell_angle_alpha                98.1810(10)
_cell_angle_beta                 107.1510(10)
_cell_angle_gamma                103.6240(10)
_cell_volume                     1350.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    90.0(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536

_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      90.0(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            7702
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.941
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             5844
_reflns_number_gt                4180
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_gt          0.0617
_refine_ls_wR_factor_ref         0.0660
_refine_ls_goodness_of_fit_ref   1.322
_refine_ls_restrained_S_all      1.322
_refine_ls_number_reflns         5844
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.250
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0061(4)

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 SMART APEXII'
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

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 1.02505(16) 0.78769(10) 0.86899(11) 0.0167(3) Uani d . . . 1 . .
N N3 0.73880(16) 0.99384(10) 0.77267(10) 0.0177(3) Uani d . . . 1 . .
N N4 0.74512(15) 1.11971(9) 0.91156(10) 0.0182(3) Uani d . . . 1 . .
N N2 0.79812(15) 0.79627(9) 0.74864(10) 0.0174(3) Uani d . . . 1 . .
C C5 0.88830(19) 0.81831(11) 0.85578(12) 0.0164(4) Uani d . . . 1 . .
C C6 1.02511(19) 0.74425(11) 0.76358(12) 0.0171(4) Uani d . . . 1 . .
C C7 0.76347(19) 0.94103(11) 0.95635(12) 0.0177(4) Uani d . . . 1 . .
C C8 0.74643(18) 1.01619(11) 0.88025(12) 0.0171(4) Uani d . . . 1 . .
C C9 0.81617(19) 0.72194(11) 0.56747(12) 0.0169(4) Uani d . . . 1 . .
C C10 0.83957(18) 0.85722(11) 0.95026(12) 0.0166(4) Uani d . . . 1 . .
C C11 0.6167(2) 1.14186(12) 0.44294(13) 0.0235(4) Uani d . . . 1 . .
H H11 0.5617 1.1866 0.4036 0.028 Uiso calc U . R 1 . .
C C12 0.86392(19) 0.80112(12) 1.03664(12) 0.0200(4) Uani d . . . 1 . .
H H12 0.9193 0.7468 1.0348 0.024 Uiso calc U . R 1 . .
C C13 1.3089(2) 0.73662(12) 0.83258(13) 0.0223(4) Uani d . . . 1 . .
H H13 1.3292 0.7918 0.8969 0.027 Uiso calc U . R 1 . .
C C14 0.88346(19) 0.75101(11) 0.69050(12) 0.0172(4) Uani d . . . 1 . .
C C15 1.1311(2) 0.61927(12) 0.65703(13) 0.0218(4) Uani d . . . 1 . .
H H15 1.0277 0.5924 0.6003 0.026 Uiso calc U . R 1 . .
C C16 0.7822(2) 1.01405(12) 0.55880(13) 0.0224(4) Uani d . . . 1 . .
H H16 0.8406 0.971 0.5984 0.027 Uiso calc U . R 1 . .
C C17 0.73833(19) 1.16477(12) 0.81918(12) 0.0187(4) Uani d . . . 1 . .
C C18 1.15629(19) 0.70096(12) 0.75058(13) 0.0176(4) Uani d . . . 1 . .
C C19 1.4050(2) 0.61377(12) 0.72861(13) 0.0258(4) Uani d . . . 1 . .
H H19 1.4895 0.5845 0.7211 0.031 Uiso calc U . R 1 . .
C C20 1.2543(2) 0.57738(12) 0.64626(13) 0.0243(4) Uani d . . . 1 . .
H H20 1.2355 0.523 0.5816 0.029 Uiso calc U . R 1 . .
C C41 0.8457(2) 1.34883(12) 0.78106(13) 0.0258(4) Uani d . . . 1 . .
H H41 0.897 1.3159 0.7365 0.031 Uiso calc U . R 1 . .
C C22 0.6502(2) 0.67475(11) 0.51281(12) 0.0211(4) Uani d . . . 1 . .
H H22 0.5811 0.6577 0.5549 0.025 Uiso calc U . R 1 . .
C C23 0.70730(19) 0.96008(12) 1.04578(12) 0.0215(4) Uani d . . . 1 . .
H H23 0.6533 1.015 1.0498 0.026 Uiso calc U . R 1 . .
C C24 0.8093(2) 0.82288(13) 1.12434(13) 0.0260(4) Uani d . . . 1 . .
H H24 0.8276 0.7839 1.1821 0.031 Uiso calc U . R 1 . .
C C25 0.6802(2) 1.33431(12) 0.89647(13) 0.0254(4) Uani d . . . 1 . .
H H25 0.6175 1.2916 0.9316 0.031 Uiso calc U . R 1 . .
C C26 0.73302(19) 1.08667(12) 0.73098(12) 0.0184(4) Uani d . . . 1 . .
C C27 0.8495(2) 0.72466(12) 0.38928(13) 0.0271(4) Uani d . . . 1 . .
H H27 0.9181 0.742 0.347 0.033 Uiso calc U . R 1 . .
C C28 0.71858(19) 1.08410(11) 0.61401(12) 0.0191(4) Uani d . . . 1 . .
C C29 0.7283(2) 0.90114(12) 1.12807(13) 0.0270(4) Uani d . . . 1 . .
H H29 0.6872 0.9145 1.1869 0.032 Uiso calc U . R 1 . .
C C30 0.75293(19) 1.28372(12) 0.83066(12) 0.0195(4) Uani d . . . 1 . .
C C31 0.63494(19) 1.14760(11) 0.55437(12) 0.0213(4) Uani d . . . 1 . .
H H31 0.5901 1.1952 0.5906 0.026 Uiso calc U . R 1 . .
C C32 0.9148(2) 0.74664(12) 0.50420(13) 0.0224(4) Uani d . . . 1 . .
H H32 1.0281 0.7789 0.5403 0.027 Uiso calc U . R 1 . .
C C33 1.4315(2) 0.69347(12) 0.82228(14) 0.0258(4) Uani d . . . 1 . .
H H33 1.5344 0.7186 0.8796 0.031 Uiso calc U . R 1 . .
C C34 0.6849(2) 0.67760(12) 0.33537(13) 0.0270(4) Uani d . . . 1 . .
H H34 0.6405 0.6626 0.2563 0.032 Uiso calc U . R 1 . .
C C35 0.6788(2) 1.07084(12) 0.38897(13) 0.0249(4) Uani d . . . 1 . .
H H35 0.6649 1.0663 0.3123 0.03 Uiso calc U . R 1 . .
C C36 0.5854(2) 0.65253(12) 0.39743(13) 0.0244(4) Uani d . . . 1 . .
H H36 0.4723 0.62 0.3608 0.029 Uiso calc U . R 1 . .
C C37 0.8636(2) 1.46096(12) 0.79617(14) 0.0320(5) Uani d . . . 1 . .
H H37 0.9275 1.5046 0.7623 0.038 Uiso calc U . R 1 . .
C C38 0.7610(2) 1.00651(12) 0.44632(13) 0.0256(4) Uani d . . . 1 . .
H H38 0.8027 0.9574 0.409 0.031 Uiso calc U . R 1 . .
C C39 0.7893(2) 1.50946(13) 0.86001(14) 0.0350(5) Uani d . . . 1 . .
H H39 0.8003 1.5861 0.869 0.042 Uiso calc U . R 1 . .
C C40 0.6991(2) 1.44694(13) 0.91085(14) 0.0327(5) Uani d . . . 1 . .
H H40 0.6495 1.4809 0.956 0.039 Uiso calc U . R 1 . .
H H2 1.113(2) 0.8049(12) 0.9384(13) 0.046(6) Uiso d . . . 1 . .
H H1 0.733(2) 0.9240(12) 0.7346(13) 0.039(5) Uiso d . . . 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 C5 . 1.356(2) ?
N1 C6 . 1.3931(18) ?
N1 H2 . 0.964(17) ?
N3 C8 . 1.3530(18) ?
N3 C26 . 1.3782(17) ?
N3 H1 . 0.939(15) ?
N4 C8 . 1.3336(17) ?
N4 C17 . 1.3869(17) ?
N2 C5 . 1.3300(18) ?
N2 C14 . 1.3866(19) ?
C5 C10 . 1.474(2) ?
C6 C14 . 1.379(2) ?
C6 C18 . 1.465(2) ?
C7 C23 . 1.404(2) ?
C7 C10 . 1.410(2) ?
C7 C8 . 1.470(2) ?
C9 C32 . 1.390(2) ?
C9 C22 . 1.395(2) ?
C9 C14 . 1.476(2) ?
C10 C12 . 1.4006(19) ?
C11 C35 . 1.385(2) ?
C11 C31 . 1.3856(19) ?
C11 H11 . 0.95 ?
C12 C24 . 1.380(2) ?
C12 H12 . 0.95 ?
C13 C33 . 1.382(2) ?
C13 C18 . 1.392(2) ?
C13 H13 . 0.95 ?
C15 C20 . 1.380(2) ?
C15 C18 . 1.4025(19) ?
C15 H15 . 0.95 ?
C16 C38 . 1.391(2) ?
C16 C28 . 1.395(2) ?
C16 H16 . 0.95 ?
C17 C26 . 1.3844(19) ?
C17 C30 . 1.4797(19) ?
C19 C20 . 1.382(2) ?
C19 C33 . 1.386(2) ?
C19 H19 . 0.95 ?
C20 H20 . 0.95 ?
C41 C37 . 1.385(2) ?
C41 C30 . 1.395(2) ?
C41 H41 . 0.95 ?
C22 C36 . 1.387(2) ?
C22 H22 . 0.95 ?
C23 C29 . 1.381(2) ?
C23 H23 . 0.95 ?
C24 C29 . 1.378(2) ?
C24 H24 . 0.95 ?
C25 C40 . 1.390(2) ?
C25 C30 . 1.395(2) ?
C25 H25 . 0.95 ?
C26 C28 . 1.469(2) ?
C27 C32 . 1.382(2) ?
C27 C34 . 1.383(2) ?
C27 H27 . 0.95 ?
C28 C31 . 1.397(2) ?
C29 H29 . 0.95 ?
C31 H31 . 0.95 ?
C32 H32 . 0.95 ?
C33 H33 . 0.95 ?
C34 C36 . 1.384(2) ?
C34 H34 . 0.95 ?
C35 C38 . 1.384(2) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?
C37 C39 . 1.376(2) ?
C37 H37 . 0.95 ?
C38 H38 . 0.95 ?
C39 C40 . 1.376(2) ?
C39 H39 . 0.95 ?
C40 H40 . 0.95 ?

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
C5 N1 C6 . . 107.99(13) ?
C5 N1 H2 . . 124.7(10) ?
C6 N1 H2 . . 126.6(11) ?
C8 N3 C26 . . 108.92(13) ?
C8 N3 H1 . . 123.1(9) ?
C26 N3 H1 . . 127.9(9) ?
C8 N4 C17 . . 105.71(12) ?
C5 N2 C14 . . 105.67(13) ?
N2 C5 N1 . . 111.23(14) ?
N2 C5 C10 . . 125.39(15) ?
N1 C5 C10 . . 122.93(14) ?
C14 C6 N1 . . 104.83(14) ?
C14 C6 C18 . . 134.26(14) ?
N1 C6 C18 . . 120.88(14) ?
C23 C7 C10 . . 118.27(14) ?
C23 C7 C8 . . 116.22(14) ?
C10 C7 C8 . . 125.39(14) ?
N4 C8 N3 . . 110.64(13) ?
N4 C8 C7 . . 123.34(13) ?
N3 C8 C7 . . 125.93(13) ?
C32 C9 C22 . . 118.78(14) ?
C32 C9 C14 . . 120.92(14) ?
C22 C9 C14 . . 120.20(14) ?
C12 C10 C7 . . 118.70(14) ?
C12 C10 C5 . . 116.20(14) ?
C7 C10 C5 . . 125.00(14) ?
C35 C11 C31 . . 119.97(15) ?
C35 C11 H11 . . 120.0 ?
C31 C11 H11 . . 120.0 ?
C24 C12 C10 . . 121.57(16) ?
C24 C12 H12 . . 119.2 ?
C10 C12 H12 . . 119.2 ?
C33 C13 C18 . . 121.35(15) ?
C33 C13 H13 . . 119.3 ?
C18 C13 H13 . . 119.3 ?
C6 C14 N2 . . 110.28(13) ?
C6 C14 C9 . . 131.28(15) ?
N2 C14 C9 . . 118.42(14) ?
C20 C15 C18 . . 120.93(16) ?
C20 C15 H15 . . 119.5 ?
C18 C15 H15 . . 119.5 ?
C38 C16 C28 . . 120.72(15) ?
C38 C16 H16 . . 119.6 ?
C28 C16 H16 . . 119.6 ?
C26 C17 N4 . . 110.04(12) ?
C26 C17 C30 . . 130.70(14) ?
N4 C17 C30 . . 118.97(13) ?
C13 C18 C15 . . 117.59(15) ?
C13 C18 C6 . . 121.16(14) ?
C15 C18 C6 . . 121.21(15) ?
C20 C19 C33 . . 119.23(16) ?
C20 C19 H19 . . 120.4 ?
C33 C19 H19 . . 120.4 ?
C15 C20 C19 . . 120.62(15) ?
C15 C20 H20 . . 119.7 ?
C19 C20 H20 . . 119.7 ?
C37 C41 C30 . . 120.58(16) ?
C37 C41 H41 . . 119.7 ?
C30 C41 H41 . . 119.7 ?
C36 C22 C9 . . 120.43(15) ?
C36 C22 H22 . . 119.8 ?
C9 C22 H22 . . 119.8 ?
C29 C23 C7 . . 121.80(16) ?
C29 C23 H23 . . 119.1 ?
C7 C23 H23 . . 119.1 ?
C29 C24 C12 . . 119.95(15) ?
C29 C24 H24 . . 120.0 ?
C12 C24 H24 . . 120.0 ?
C40 C25 C30 . . 120.31(16) ?
C40 C25 H25 . . 119.8 ?
C30 C25 H25 . . 119.8 ?
N3 C26 C17 . . 104.69(13) ?
N3 C26 C28 . . 120.33(13) ?
C17 C26 C28 . . 134.95(14) ?
C32 C27 C34 . . 120.52(16) ?
C32 C27 H27 . . 119.7 ?
C34 C27 H27 . . 119.7 ?
C16 C28 C31 . . 118.60(14) ?
C16 C28 C26 . . 120.39(14) ?
C31 C28 C26 . . 120.94(14) ?
C24 C29 C23 . . 119.61(15) ?
C24 C29 H29 . . 120.2 ?
C23 C29 H29 . . 120.2 ?
C25 C30 C41 . . 118.52(14) ?
C25 C30 C17 . . 120.24(14) ?
C41 C30 C17 . . 121.17(15) ?
C11 C31 C28 . . 120.70(15) ?
C11 C31 H31 . . 119.7 ?
C28 C31 H31 . . 119.7 ?
C27 C32 C9 . . 120.53(16) ?
C27 C32 H32 . . 119.7 ?
C9 C32 H32 . . 119.7 ?
C13 C33 C19 . . 120.27(16) ?
C13 C33 H33 . . 119.9 ?
C19 C33 H33 . . 119.9 ?
C27 C34 C36 . . 119.51(15) ?
C27 C34 H34 . . 120.2 ?
C36 C34 H34 . . 120.2 ?
C38 C35 C11 . . 120.25(15) ?
C38 C35 H35 . . 119.9 ?
C11 C35 H35 . . 119.9 ?
C34 C36 C22 . . 120.23(16) ?
C34 C36 H36 . . 119.9 ?
C22 C36 H36 . . 119.9 ?
C39 C37 C41 . . 120.27(17) ?
C39 C37 H37 . . 119.9 ?
C41 C37 H37 . . 119.9 ?
C35 C38 C16 . . 119.74(16) ?
C35 C38 H38 . . 120.1 ?
C16 C38 H38 . . 120.1 ?
C37 C39 C40 . . 120.04(15) ?
C37 C39 H39 . . 120.0 ?
C40 C39 H39 . . 120.0 ?
C39 C40 C25 . . 120.28(17) ?
C39 C40 H40 . . 119.9 ?
C25 C40 H40 . . 119.9 ?

_database_code_depnum_ccdc_archive 'CCDC 999576'
#######################################################################
#
#                 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_1a
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H24 N4'
_chemical_formula_iupac          ?
_chemical_formula_weight         512.59
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   15.8279(16)
_cell_length_b                   14.7391(15)
_cell_length_c                   11.5440(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2693.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    90.0(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072

_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      90.0(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            13236
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         25.95
_diffrn_reflns_theta_full        25.95
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
;

_reflns_number_total             4290
_reflns_number_gt                3580
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0890
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_number_reflns         4290
_refine_ls_number_parameters     362
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0432P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.189
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0098(10)
_refine_ls_abs_structure_details 
;
;
_refine_ls_abs_structure_Flack   -0.3(10)

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 SMART APEXII'
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

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 N4 0.08541(14) 0.30729(16) 0.6139(2) 0.0231(6) Uani d . . . 1 . .
N N1 0.26703(14) 0.53896(15) 0.6656(2) 0.0211(5) Uani d . . . 1 . .
N N2 0.14510(14) 0.56946(16) 0.7803(2) 0.0202(5) Uani d . . . 1 . .
C C4 0.19832(16) 0.67892(19) 0.9159(2) 0.0205(6) Uani d . . . 1 . .
C C5 0.16728(17) 0.35416(19) 0.7676(3) 0.0210(6) Uani d . . . 1 . .
N N3 0.15703(14) 0.42363(15) 0.6879(2) 0.0201(5) Uani d . . . 1 . .
C C7 0.28382(16) 0.60029(19) 0.7416(2) 0.0188(6) Uani d . . . 1 . .
C C8 0.12915(17) 0.54480(19) 0.5680(2) 0.0198(6) Uani d . . . 1 . .
C C9 0.15800(19) 0.6455(2) 1.0149(3) 0.0301(7) Uani d . . . 1 . .
H H9 0.1408 0.5838 1.0189 0.036 Uiso calc U . R 1 . .
C C10 0.1629(2) 0.3453(2) 0.9816(3) 0.0293(7) Uani d . . . 1 . .
H H10 0.1081 0.3194 0.9755 0.035 Uiso calc U . R 1 . .
C C11 0.1978(2) 0.3609(2) 1.0900(3) 0.0352(8) Uani d . . . 1 . .
H H11 0.1669 0.3451 1.1576 0.042 Uiso calc U . R 1 . .
C C12 0.36796(15) 0.64305(18) 0.7478(3) 0.0196(6) Uani d . . . 1 . .
C C13 0.28841(19) 0.4044(2) 0.8934(3) 0.0273(7) Uani d . . . 1 . .
H H13 0.3205 0.4184 0.8261 0.033 Uiso calc U . R 1 . .
C C14 0.48193(18) 0.7145(2) 0.8515(3) 0.0258(7) Uani d . . . 1 . .
H H14 0.506 0.7355 0.9219 0.031 Uiso calc U . R 1 . .
C C15 0.10707(16) 0.3925(2) 0.6000(2) 0.0209(6) Uani d . . . 1 . .
C C16 0.17638(17) 0.52019(18) 0.6794(3) 0.0204(6) Uani d . . . 1 . .
C C17 0.20749(17) 0.36749(19) 0.8816(2) 0.0216(7) Uani d . . . 1 . .
C C18 0.40261(17) 0.6743(2) 0.8522(3) 0.0227(7) Uani d . . . 1 . .
H H18 0.3721 0.668 0.9226 0.027 Uiso calc U . R 1 . .
C C19 0.04405(18) 0.4748(2) 0.4193(3) 0.0262(7) Uani d . . . 1 . .
H H19 0.0176 0.4231 0.3862 0.031 Uiso calc U . R 1 . .
C C20 0.52577(17) 0.7240(2) 0.7493(3) 0.0286(7) Uani d . . . 1 . .
H H20 0.5795 0.7527 0.7496 0.034 Uiso calc U . R 1 . .
C C21 0.20628(19) 0.8265(2) 1.0035(3) 0.0350(8) Uani d . . . 1 . .
H H21 0.2218 0.8887 0.9995 0.042 Uiso calc U . R 1 . .
C C22 0.07775(18) 0.6350(2) 0.4135(3) 0.0269(7) Uani d . . . 1 . .
H H22 0.0731 0.692 0.3756 0.032 Uiso calc U . R 1 . .
C C23 0.2768(2) 0.3991(2) 1.1004(3) 0.0378(8) Uani d . . . 1 . .
H H23 0.2999 0.4105 1.1749 0.045 Uiso calc U . R 1 . .
C C24 0.11590(17) 0.18864(19) 0.7608(3) 0.0238(6) Uani d . . . 1 . .
C C25 0.49255(18) 0.6924(2) 0.6463(3) 0.0281(7) Uani d . . . 1 . .
H H25 0.5236 0.6985 0.5764 0.034 Uiso calc U . R 1 . .
C C26 0.22334(18) 0.7693(2) 0.9111(3) 0.0258(7) Uani d . . . 1 . .
H H26 0.252 0.7918 0.8447 0.031 Uiso calc U . R 1 . .
C C27 0.04455(19) 0.1373(2) 0.7334(3) 0.0352(8) Uani d . . . 1 . .
H H27 0.0015 0.1627 0.6861 0.042 Uiso calc U . R 1 . .
C C28 0.41396(17) 0.65177(18) 0.6456(2) 0.0215(6) Uani d . . . 1 . .
H H28 0.3911 0.6296 0.5749 0.026 Uiso calc U . R 1 . .
C C29 0.0983(2) 0.0110(2) 0.8425(3) 0.0337(8) Uani d . . . 1 . .
H H29 0.0915 -0.0486 0.8723 0.04 Uiso calc U . R 1 . .
C C30 0.12435(17) 0.6279(2) 0.5155(3) 0.0237(7) Uani d . . . 1 . .
H H30 0.152 0.6793 0.5476 0.028 Uiso calc U . R 1 . .
C C31 0.12337(16) 0.2821(2) 0.7178(2) 0.0226(7) Uani d . . . 1 . .
C C32 0.20757(17) 0.61786(19) 0.8158(2) 0.0185(6) Uani d . . . 1 . .
C C33 0.08978(16) 0.4681(2) 0.5211(2) 0.0221(7) Uani d . . . 1 . .
C C34 0.17896(19) 0.1479(2) 0.8264(3) 0.0276(7) Uani d . . . 1 . .
H H34 0.2288 0.1811 0.844 0.033 Uiso calc U . R 1 . .
C C35 0.03799(18) 0.5594(2) 0.3669(3) 0.0284(7) Uani d . . . 1 . .
H H35 0.006 0.5656 0.2977 0.034 Uiso calc U . R 1 . .
C C36 0.16721(19) 0.7936(3) 1.1003(3) 0.0456(10) Uani d . . . 1 . .
H H36 0.1563 0.8329 1.1637 0.055 Uiso calc U . R 1 . .
C C37 0.3223(2) 0.4208(2) 1.0018(3) 0.0332(8) Uani d . . . 1 . .
H H37 0.3769 0.447 1.0086 0.04 Uiso calc U . R 1 . .
C C38 0.0359(2) 0.0496(2) 0.7745(3) 0.0398(9) Uani d . . . 1 . .
H H38 -0.0132 0.0157 0.7559 0.048 Uiso calc U . R 1 . .
C C39 0.1706(2) 0.0600(2) 0.8665(3) 0.0317(8) Uani d . . . 1 . .
H H39 0.2147 0.0332 0.9107 0.038 Uiso calc U . R 1 . .
C C40 0.1435(2) 0.7037(3) 1.1068(3) 0.0454(10) Uani d . . . 1 . .
H H40 0.1169 0.6816 1.175 0.054 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
N4 C15 . 1.312(4) ?
N4 C31 . 1.391(3) ?
N1 C7 . 1.287(4) ?
N1 C16 . 1.470(3) ?
N2 C32 . 1.286(3) ?
N2 C16 . 1.459(4) ?
C4 C26 . 1.391(4) ?
C4 C9 . 1.398(4) ?
C4 C32 . 1.473(4) ?
C5 N3 . 1.386(4) ?
C5 C31 . 1.393(4) ?
C5 C17 . 1.475(4) ?
N3 C15 . 1.365(3) ?
N3 C16 . 1.459(3) ?
C7 C12 . 1.475(4) ?
C7 C32 . 1.503(4) ?
C8 C30 . 1.369(4) ?
C8 C33 . 1.400(4) ?
C8 C16 . 1.531(4) ?
C9 C40 . 1.384(5) ?
C9 H9 . 0.95 ?
C10 C11 . 1.387(4) ?
C10 C17 . 1.393(4) ?
C10 H10 . 0.95 ?
C11 C23 . 1.376(4) ?
C11 H11 . 0.95 ?
C12 C28 . 1.393(4) ?
C12 C18 . 1.402(4) ?
C13 C37 . 1.383(4) ?
C13 C17 . 1.398(4) ?
C13 H13 . 0.95 ?
C14 C20 . 1.376(4) ?
C14 C18 . 1.388(4) ?
C14 H14 . 0.95 ?
C15 C33 . 1.465(4) ?
C18 H18 . 0.95 ?
C19 C33 . 1.384(4) ?
C19 C35 . 1.389(4) ?
C19 H19 . 0.95 ?
C20 C25 . 1.381(4) ?
C20 H20 . 0.95 ?
C21 C36 . 1.367(5) ?
C21 C26 . 1.386(4) ?
C21 H21 . 0.95 ?
C22 C35 . 1.388(4) ?
C22 C30 . 1.393(4) ?
C22 H22 . 0.95 ?
C23 C37 . 1.385(5) ?
C23 H23 . 0.95 ?
C24 C34 . 1.389(4) ?
C24 C27 . 1.396(4) ?
C24 C31 . 1.469(4) ?
C25 C28 . 1.381(4) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?
C27 C38 . 1.383(5) ?
C27 H27 . 0.95 ?
C28 H28 . 0.95 ?
C29 C39 . 1.381(4) ?
C29 C38 . 1.383(5) ?
C29 H29 . 0.95 ?
C30 H30 . 0.95 ?
C34 C39 . 1.382(4) ?
C34 H34 . 0.95 ?
C35 H35 . 0.95 ?
C36 C40 . 1.379(5) ?
C36 H36 . 0.95 ?
C37 H37 . 0.95 ?
C38 H38 . 0.95 ?
C39 H39 . 0.95 ?
C40 H40 . 0.95 ?

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
C15 N4 C31 . . 104.3(2) ?
C7 N1 C16 . . 105.1(2) ?
C32 N2 C16 . . 105.6(2) ?
C26 C4 C9 . . 120.0(3) ?
C26 C4 C32 . . 121.7(3) ?
C9 C4 C32 . . 118.1(3) ?
N3 C5 C31 . . 103.4(2) ?
N3 C5 C17 . . 123.0(2) ?
C31 C5 C17 . . 133.2(3) ?
C15 N3 C5 . . 108.2(2) ?
C15 N3 C16 . . 113.5(2) ?
C5 N3 C16 . . 137.8(2) ?
N1 C7 C12 . . 121.3(2) ?
N1 C7 C32 . . 110.1(2) ?
C12 C7 C32 . . 128.6(2) ?
C30 C8 C33 . . 121.8(3) ?
C30 C8 C16 . . 127.7(3) ?
C33 C8 C16 . . 110.6(2) ?
C40 C9 C4 . . 119.0(3) ?
C40 C9 H9 . . 120.5 ?
C4 C9 H9 . . 120.5 ?
C11 C10 C17 . . 120.5(3) ?
C11 C10 H10 . . 119.8 ?
C17 C10 H10 . . 119.8 ?
C23 C11 C10 . . 120.6(3) ?
C23 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C28 C12 C18 . . 119.6(2) ?
C28 C12 C7 . . 118.0(2) ?
C18 C12 C7 . . 122.4(2) ?
C37 C13 C17 . . 120.8(3) ?
C37 C13 H13 . . 119.6 ?
C17 C13 H13 . . 119.6 ?
C20 C14 C18 . . 120.3(3) ?
C20 C14 H14 . . 119.8 ?
C18 C14 H14 . . 119.8 ?
N4 C15 N3 . . 112.5(2) ?
N4 C15 C33 . . 139.0(3) ?
N3 C15 C33 . . 108.4(2) ?
N2 C16 N3 . . 111.1(2) ?
N2 C16 N1 . . 108.9(2) ?
N3 C16 N1 . . 113.3(2) ?
N2 C16 C8 . . 112.8(2) ?
N3 C16 C8 . . 100.6(2) ?
N1 C16 C8 . . 110.0(2) ?
C10 C17 C13 . . 118.4(3) ?
C10 C17 C5 . . 119.3(2) ?
C13 C17 C5 . . 122.3(3) ?
C14 C18 C12 . . 119.3(3) ?
C14 C18 H18 . . 120.4 ?
C12 C18 H18 . . 120.4 ?
C33 C19 C35 . . 118.1(3) ?
C33 C19 H19 . . 121.0 ?
C35 C19 H19 . . 121.0 ?
C14 C20 C25 . . 120.8(2) ?
C14 C20 H20 . . 119.6 ?
C25 C20 H20 . . 119.6 ?
C36 C21 C26 . . 120.1(3) ?
C36 C21 H21 . . 119.9 ?
C26 C21 H21 . . 119.9 ?
C35 C22 C30 . . 120.5(3) ?
C35 C22 H22 . . 119.7 ?
C30 C22 H22 . . 119.7 ?
C11 C23 C37 . . 119.7(3) ?
C11 C23 H23 . . 120.1 ?
C37 C23 H23 . . 120.1 ?
C34 C24 C27 . . 118.0(3) ?
C34 C24 C31 . . 122.1(3) ?
C27 C24 C31 . . 119.8(3) ?
C28 C25 C20 . . 119.7(3) ?
C28 C25 H25 . . 120.2 ?
C20 C25 H25 . . 120.2 ?
C21 C26 C4 . . 119.7(3) ?
C21 C26 H26 . . 120.1 ?
C4 C26 H26 . . 120.1 ?
C38 C27 C24 . . 120.6(3) ?
C38 C27 H27 . . 119.7 ?
C24 C27 H27 . . 119.7 ?
C25 C28 C12 . . 120.4(3) ?
C25 C28 H28 . . 119.8 ?
C12 C28 H28 . . 119.8 ?
C39 C29 C38 . . 119.4(3) ?
C39 C29 H29 . . 120.3 ?
C38 C29 H29 . . 120.3 ?
C8 C30 C22 . . 118.1(3) ?
C8 C30 H30 . . 121.0 ?
C22 C30 H30 . . 121.0 ?
N4 C31 C5 . . 111.6(3) ?
N4 C31 C24 . . 120.4(3) ?
C5 C31 C24 . . 128.0(3) ?
N2 C32 C4 . . 120.8(2) ?
N2 C32 C7 . . 109.9(2) ?
C4 C32 C7 . . 129.3(2) ?
C19 C33 C8 . . 120.2(3) ?
C19 C33 C15 . . 132.9(3) ?
C8 C33 C15 . . 106.8(2) ?
C39 C34 C24 . . 121.3(3) ?
C39 C34 H34 . . 119.4 ?
C24 C34 H34 . . 119.4 ?
C22 C35 C19 . . 121.3(3) ?
C22 C35 H35 . . 119.3 ?
C19 C35 H35 . . 119.3 ?
C21 C36 C40 . . 120.6(3) ?
C21 C36 H36 . . 119.7 ?
C40 C36 H36 . . 119.7 ?
C13 C37 C23 . . 120.1(3) ?
C13 C37 H37 . . 120.0 ?
C23 C37 H37 . . 120.0 ?
C29 C38 C27 . . 120.6(3) ?
C29 C38 H38 . . 119.7 ?
C27 C38 H38 . . 119.7 ?
C29 C39 C34 . . 120.1(3) ?
C29 C39 H39 . . 119.9 ?
C34 C39 H39 . . 119.9 ?
C36 C40 C9 . . 120.6(3) ?
C36 C40 H40 . . 119.7 ?
C9 C40 H40 . . 119.7 ?

_database_code_depnum_ccdc_archive 'CCDC 999577'
