# 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_dsrp_6

_audit_creation_method           SHELXL-97
_chemical_name_systematic        1
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H31 N7'
_chemical_melting_point          ?

_exptl_crystal_description       Block
_exptl_crystal_colour            White

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         549.67

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   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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                   11.9764(3)
_cell_length_b                   19.8384(5)
_cell_length_c                   12.5324(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.803(2)
_cell_angle_gamma                90.00
_cell_volume                     2744.88(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            34823
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.72
_reflns_number_total             5231
_reflns_number_gt                3514
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1348P)²+2.0807P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5231
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0765
_refine_ls_wR_factor_ref         0.2549
_refine_ls_wR_factor_gt          0.2273
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.222
_refine_ls_shift/su_mean         0.052

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 0.4599(2) 0.88177(13) 0.2915(2) 0.0496(6) Uani 1 1 d . . .
N6 N 0.4662(2) 0.93145(16) 0.1005(2) 0.0605(8) Uani 1 1 d . . .
N4 N 0.7863(2) 0.80019(16) 0.7279(2) 0.0630(8) Uani 1 1 d . . .
N3 N 0.6607(2) 0.80681(15) 0.5418(2) 0.0577(7) Uani 1 1 d . . .
C13 C 0.6179(3) 0.71978(16) 0.6526(3) 0.0529(8) Uani 1 1 d . . .
N5 N 0.3733(3) 1.03269(17) 0.1254(3) 0.0774(10) Uani 1 1 d . . .
H5 H 0.3089 1.0562 0.0913 0.093 Uiso 1 1 calc R . .
C19 C 0.5568(3) 0.79427(18) 0.4322(3) 0.0605(9) Uani 1 1 d . . .
N7 N 0.6655(3) 0.92181(18) 0.1373(3) 0.0757(10) Uani 1 1 d . . .
C18 C 0.5137(3) 0.70321(17) 0.5533(3) 0.0531(8) Uani 1 1 d . . .
C28 C 0.5792(3) 0.95907(18) 0.1441(3) 0.0562(8) Uani 1 1 d . . .
C1 C 0.4831(3) 0.85854(16) 0.3976(3) 0.0503(7) Uani 1 1 d . . .
C10 C 0.8238(3) 0.85417(17) 0.6721(3) 0.0594(9) Uani 1 1 d . . .
C21 C 0.3690(3) 0.95946(18) 0.1321(3) 0.0562(8) Uani 1 1 d . . .
C12 C 0.6913(3) 0.77611(17) 0.6451(3) 0.0548(8) Uani 1 1 d . . .
N2 N 0.4814(3) 0.74338(17) 0.4571(3) 0.0809(11) Uani 1 1 d . . .
H2 H 0.4092 0.7382 0.4058 0.097 Uiso 1 1 calc R . .
C14 C 0.6439(3) 0.6807(2) 0.7536(3) 0.0693(10) Uani 1 1 d . . .
H14 H 0.7109 0.6911 0.8203 0.083 Uiso 1 1 calc R . .
C9 C 0.9201(3) 0.89735(19) 0.7210(4) 0.0741(11) Uani 1 1 d . . .
H9 H 0.9699 0.8948 0.7992 0.089 Uiso 1 1 calc R . .
C2 C 0.4417(3) 0.8900(2) 0.4734(3) 0.0644(9) Uani 1 1 d . . .
H2 H 0.4592 0.8727 0.5471 0.077 Uiso 1 1 calc R . .
C20 C 0.5974(4) 0.7673(2) 0.3401(3) 0.0717(11) Uani 1 1 d . . .
H20A H 0.5279 0.7592 0.2702 0.107 Uiso 0.50 1 calc PR . .
H20B H 0.6409 0.7259 0.3664 0.107 Uiso 0.50 1 calc PR . .
H20C H 0.6493 0.7997 0.3254 0.107 Uiso 0.50 1 calc PR . .
H20D H 0.6842 0.7640 0.3711 0.107 Uiso 0.50 1 calc PR . .
H20E H 0.5711 0.7973 0.2749 0.107 Uiso 0.50 1 calc PR . .
H20F H 0.5628 0.7235 0.3159 0.107 Uiso 0.50 1 calc PR . .
C17 C 0.4435(3) 0.6491(2) 0.5582(4) 0.0711(10) Uani 1 1 d . . .
H17 H 0.3757 0.6374 0.4932 0.085 Uiso 1 1 calc R . .
C11 C 0.7471(3) 0.85872(18) 0.5584(3) 0.0629(9) Uani 1 1 d . . .
C22 C 0.4822(4) 0.86552(19) 0.0670(3) 0.0613(9) Uani 1 1 d . . .
C7 C 0.8628(4) 0.9480(2) 0.5320(4) 0.0847(13) Uani 1 1 d . . .
H7 H 0.8781 0.9795 0.4844 0.102 Uiso 1 1 calc R . .
C29 C 0.5934(4) 1.0288(2) 0.1917(3) 0.0673(10) Uani 1 1 d . . .
C27 C 0.6055(4) 0.8618(2) 0.0890(3) 0.0691(10) Uani 1 1 d . . .
C34 C 0.4900(4) 1.0636(2) 0.1783(3) 0.0675(10) Uani 1 1 d . . .
C4 C 0.3487(3) 0.9724(2) 0.3273(3) 0.0635(9) Uani 1 1 d . . .
H4 H 0.3026 1.0112 0.3013 0.076 Uiso 1 1 calc R . .
C35 C 0.2431(3) 0.9377(3) 0.0515(4) 0.0854(13) Uani 1 1 d . . .
H35A H 0.2368 0.8895 0.0538 0.128 Uiso 0.50 1 calc PR . .
H35B H 0.2289 0.9517 -0.0261 0.128 Uiso 0.50 1 calc PR . .
H35C H 0.1841 0.9581 0.0756 0.128 Uiso 0.50 1 calc PR . .
H35D H 0.1964 0.9767 0.0151 0.128 Uiso 0.50 1 calc PR . .
H35E H 0.2043 0.9145 0.0950 0.128 Uiso 0.50 1 calc PR . .
H35F H 0.2491 0.9081 -0.0067 0.128 Uiso 0.50 1 calc PR . .
C8 C 0.9402(4) 0.9451(2) 0.6487(5) 0.0908(15) Uani 1 1 d . . .
H8 H 1.0049 0.9750 0.6781 0.109 Uiso 1 1 calc R . .
C3 C 0.3742(4) 0.9475(2) 0.4373(3) 0.0721(11) Uani 1 1 d . . .
H3 H 0.3455 0.9698 0.4869 0.087 Uiso 1 1 calc R . .
C6 C 0.7647(4) 0.9057(2) 0.4852(4) 0.0762(11) Uani 1 1 d . . .
H6 H 0.7126 0.9086 0.4077 0.091 Uiso 1 1 calc R . .
C23 C 0.4079(4) 0.8102(3) 0.0231(3) 0.0802(12) Uani 1 1 d . . .
H23 H 0.3260 0.8118 0.0099 0.096 Uiso 1 1 calc R . .
C16 C 0.4727(4) 0.6127(3) 0.6571(4) 0.0926(14) Uani 1 1 d . . .
H16 H 0.4242 0.5764 0.6591 0.111 Uiso 1 1 calc R . .
C31 C 0.7132(6) 1.1245(3) 0.2764(4) 0.1063(18) Uani 1 1 d . . .
H31 H 0.7888 1.1448 0.3101 0.128 Uiso 1 1 calc R . .
C24 C 0.4582(6) 0.7540(2) 0.0000(4) 0.0933(15) Uani 1 1 d . . .
H24 H 0.4093 0.7166 -0.0303 0.112 Uiso 1 1 calc R . .
C33 C 0.4965(5) 1.1303(2) 0.2125(4) 0.0858(13) Uani 1 1 d . . .
H33 H 0.4265 1.1542 0.2031 0.103 Uiso 1 1 calc R . .
C26 C 0.6537(5) 0.8024(3) 0.0646(4) 0.0878(13) Uani 1 1 d . . .
H26 H 0.7358 0.7991 0.0792 0.105 Uiso 1 1 calc R . .
C15 C 0.5720(4) 0.6285(2) 0.7537(4) 0.0900(14) Uani 1 1 d . . .
H15 H 0.5904 0.6028 0.8205 0.108 Uiso 1 1 calc R . .
C25 C 0.5792(7) 0.7503(2) 0.0196(5) 0.0987(16) Uani 1 1 d . . .
H25 H 0.6099 0.7109 0.0013 0.118 Uiso 1 1 calc R . .
C30 C 0.7040(4) 1.0590(3) 0.2418(4) 0.0856(13) Uani 1 1 d . . .
H30 H 0.7738 1.0346 0.2523 0.103 Uiso 1 1 calc R . .
C32 C 0.6089(7) 1.1607(3) 0.2611(4) 0.1044(18) Uani 1 1 d . . .
H32 H 0.6147 1.2056 0.2836 0.125 Uiso 1 1 calc R . .
C5 C 0.3937(3) 0.93772(17) 0.2577(3) 0.0500(7) 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
N1 C1 1.330(4) . ?
N1 C5 1.334(4) . ?
N6 C28 1.362(4) . ?
N6 C22 1.409(5) . ?
N6 C21 1.477(4) . ?
N4 C12 1.298(4) . ?
N4 C10 1.443(5) . ?
N3 C12 1.346(4) . ?
N3 C11 1.417(4) . ?
N3 C19 1.474(4) . ?
C13 C14 1.412(5) . ?
C13 C18 1.418(4) . ?
C13 C12 1.447(5) . ?
N5 C34 1.433(5) . ?
N5 C21 1.457(5) . ?
C19 N2 1.467(5) . ?
C19 C20 1.513(5) . ?
C19 C1 1.516(5) . ?
N7 C28 1.300(4) . ?
N7 C27 1.400(5) . ?
C18 N2 1.371(4) . ?
C18 C17 1.379(5) . ?
C28 C29 1.490(5) . ?
C1 C2 1.380(5) . ?
C10 C9 1.376(5) . ?
C10 C11 1.366(5) . ?
C21 C35 1.516(5) . ?
C21 C5 1.546(4) . ?
C14 C15 1.348(6) . ?
C9 C8 1.395(6) . ?
C2 C3 1.369(5) . ?
C17 C16 1.358(6) . ?
C11 C6 1.380(5) . ?
C22 C23 1.385(6) . ?
C22 C27 1.395(6) . ?
C7 C6 1.377(6) . ?
C7 C8 1.396(7) . ?
C29 C30 1.366(6) . ?
C29 C34 1.370(6) . ?
C27 C26 1.397(6) . ?
C34 C33 1.383(6) . ?
C4 C5 1.373(5) . ?
C4 C3 1.383(5) . ?
C23 C24 1.351(7) . ?
C16 C15 1.365(6) . ?
C31 C30 1.360(8) . ?
C31 C32 1.388(8) . ?
C24 C25 1.374(8) . ?
C33 C32 1.382(8) . ?
C26 C25 1.339(7) . ?

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
C1 N1 C5 118.3(3) . . ?
C28 N6 C22 105.3(3) . . ?
C28 N6 C21 120.3(3) . . ?
C22 N6 C21 129.9(3) . . ?
C12 N4 C10 103.1(3) . . ?
C12 N3 C11 106.0(3) . . ?
C12 N3 C19 129.6(3) . . ?
C11 N3 C19 124.3(3) . . ?
C14 C13 C18 118.2(3) . . ?
C14 C13 C12 123.6(3) . . ?
C18 C13 C12 118.2(3) . . ?
C34 N5 C21 116.8(3) . . ?
N2 C19 N3 106.5(3) . . ?
N2 C19 C20 109.0(3) . . ?
N3 C19 C20 111.5(3) . . ?
N2 C19 C1 107.5(3) . . ?
N3 C19 C1 108.2(3) . . ?
C20 C19 C1 113.8(3) . . ?
C28 N7 C27 103.0(3) . . ?
N2 C18 C17 121.5(3) . . ?
N2 C18 C13 119.3(3) . . ?
C17 C18 C13 119.1(3) . . ?
N7 C28 N6 115.8(3) . . ?
N7 C28 C29 125.7(3) . . ?
N6 C28 C29 118.4(3) . . ?
N1 C1 C2 122.7(3) . . ?
N1 C1 C19 116.7(3) . . ?
C2 C1 C19 120.6(3) . . ?
C9 C10 C11 122.2(4) . . ?
C9 C10 N4 127.6(3) . . ?
C11 C10 N4 110.2(3) . . ?
N5 C21 N6 108.1(3) . . ?
N5 C21 C35 107.1(3) . . ?
N6 C21 C35 113.4(3) . . ?
N5 C21 C5 109.9(3) . . ?
N6 C21 C5 108.0(2) . . ?
C35 C21 C5 110.3(3) . . ?
N4 C12 N3 115.5(3) . . ?
N4 C12 C13 126.7(3) . . ?
N3 C12 C13 117.8(3) . . ?
C18 N2 C19 126.9(3) . . ?
C15 C14 C13 120.2(4) . . ?
C10 C9 C8 117.4(4) . . ?
C1 C2 C3 118.3(3) . . ?
C16 C17 C18 120.6(4) . . ?
C10 C11 C6 121.6(3) . . ?
C10 C11 N3 105.2(3) . . ?
C6 C11 N3 133.1(3) . . ?
C23 C22 N6 135.5(4) . . ?
C23 C22 C27 120.3(4) . . ?
N6 C22 C27 104.2(3) . . ?
C6 C7 C8 122.2(4) . . ?
C30 C29 C34 120.3(4) . . ?
C30 C29 C28 122.1(4) . . ?
C34 C29 C28 117.5(4) . . ?
N7 C27 C26 128.7(4) . . ?
N7 C27 C22 111.5(4) . . ?
C26 C27 C22 119.8(4) . . ?
C33 C34 C29 120.3(4) . . ?
C33 C34 N5 118.7(4) . . ?
C29 C34 N5 120.9(4) . . ?
C5 C4 C3 117.7(3) . . ?
C7 C8 C9 119.8(4) . . ?
C4 C3 C2 120.0(3) . . ?
C7 C6 C11 116.9(4) . . ?
C24 C23 C22 117.9(4) . . ?
C17 C16 C15 120.9(4) . . ?
C30 C31 C32 119.5(5) . . ?
C23 C24 C25 122.1(5) . . ?
C32 C33 C34 118.8(5) . . ?
C25 C26 C27 118.6(5) . . ?
C14 C15 C16 120.9(4) . . ?
C26 C25 C24 121.2(5) . . ?
C29 C30 C31 120.6(5) . . ?
C33 C32 C31 120.4(5) . . ?
N1 C5 C4 123.1(3) . . ?
N1 C5 C21 114.3(3) . . ?
C4 C5 C21 122.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.72
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.054

_database_code_depnum_ccdc_archive 'CCDC 959911'
#######################################################################
#
#                 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_ebhu140

_audit_creation_method           SHELXL-97
_chemical_name_systematic        1'
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H27 Cl2 N7 O2'
_chemical_melting_point          ?

_exptl_crystal_description       Block
_exptl_crystal_colour            White

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         648.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_int_tables_number      15
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_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'
'-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                   15.7933(7)
_cell_length_b                   11.5458(4)
_cell_length_c                   17.1322(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.286(4)
_cell_angle_gamma                90.00
_cell_volume                     3083.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    2.266
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.4797
_exptl_absorpt_correction_T_max  0.8051
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5566
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.77
_diffrn_reflns_theta_max         71.75
_reflns_number_total             2953
_reflns_number_gt                2548
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0759P)²+1.7511P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2953
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1240
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001

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
Cl1 Cl 0.06762(4) 0.34618(5) 0.11170(3) 0.0618(2) Uani 1 1 d . . .
N1 N 0.0000 -0.17851(18) 0.2500 0.0357(4) Uani 1 2 d S . .
N2 N -0.08030(9) -0.04597(13) 0.13134(9) 0.0380(3) Uani 1 1 d . . .
C2 C 0.06595(11) -0.02445(16) 0.10674(10) 0.0386(4) Uani 1 1 d . . .
N3 N -0.02533(11) 0.12660(14) 0.15514(9) 0.0414(4) Uani 1 1 d . . .
C1 C -0.01010(12) 0.01942(15) 0.13234(10) 0.0373(4) Uani 1 1 d . . .
N4 N -0.02350(11) -0.18057(15) 0.05202(9) 0.0455(4) Uani 1 1 d . . .
C16 C -0.03726(11) -0.23854(15) 0.18697(10) 0.0364(4) Uani 1 1 d . . .
C8 C -0.10914(13) 0.13222(17) 0.16963(11) 0.0419(4) Uani 1 1 d . . .
C6 C 0.12396(14) -0.16842(17) 0.02798(12) 0.0473(5) Uani 1 1 d . . .
H6 H 0.1181 -0.2356 -0.0023 0.057 Uiso 1 1 calc R . .
C7 C 0.05556(12) -0.12784(17) 0.06227(10) 0.0403(4) Uani 1 1 d . . .
C13 C -0.14469(12) 0.02247(17) 0.15622(10) 0.0417(4) Uani 1 1 d . . .
C5 C 0.20030(14) -0.10868(19) 0.03913(13) 0.0513(5) Uani 1 1 d . . .
H5 H 0.2453 -0.1351 0.0150 0.062 Uiso 1 1 calc R . .
C17 C -0.03777(14) -0.35842(17) 0.18438(12) 0.0476(5) Uani 1 1 d . . .
H17 H -0.0632 -0.3973 0.1391 0.057 Uiso 1 1 calc R . .
C18 C 0.0000 -0.4190(2) 0.2500 0.0516(7) Uani 1 2 d S . .
H18 H 0.0000 -0.4996 0.2500 0.062 Uiso 1 2 calc SR . .
C3 C 0.14499(12) 0.03290(17) 0.11887(12) 0.0456(4) Uani 1 1 d . . .
H3 H 0.1523 0.0999 0.1494 0.055 Uiso 1 1 calc R . .
C14 C -0.07762(12) -0.17117(16) 0.11263(11) 0.0399(4) Uani 1 1 d . . .
C12 C -0.22935(13) 0.0022(2) 0.16542(13) 0.0519(5) Uani 1 1 d . . .
H12 H -0.2539 -0.0709 0.1576 0.062 Uiso 1 1 calc R . .
C9 C -0.15489(15) 0.22625(19) 0.19117(12) 0.0532(5) Uani 1 1 d . . .
H9 H -0.1301 0.2992 0.1998 0.064 Uiso 1 1 calc R . .
O1 O 0.10388(14) 0.5290(2) -0.02388(14) 0.0857(6) Uani 1 1 d . . .
C10 C -0.23953(16) 0.2057(2) 0.19913(14) 0.0615(6) Uani 1 1 d . . .
H10 H -0.2731 0.2661 0.2129 0.074 Uiso 1 1 calc R . .
C4 C 0.21150(13) -0.01016(19) 0.08555(14) 0.0523(5) Uani 1 1 d . . .
H4 H 0.2645 0.0269 0.0941 0.063 Uiso 1 1 calc R . .
C15 C -0.16592(13) -0.21688(19) 0.07769(13) 0.0514(5) Uani 1 1 d . . .
H15A H -0.1992 -0.2283 0.1192 0.077 Uiso 1 1 calc R . .
H15B H -0.1600 -0.2892 0.0515 0.077 Uiso 1 1 calc R . .
H15C H -0.1943 -0.1619 0.0403 0.077 Uiso 1 1 calc R . .
C11 C -0.27493(15) 0.0950(2) 0.18660(14) 0.0608(6) Uani 1 1 d . . .
H11 H -0.3317 0.0838 0.1929 0.073 Uiso 1 1 calc R . .
H4D H -0.0360(17) -0.239(3) 0.0168(16) 0.076(8) Uiso 1 1 d . . .
H3C H 0.0078(16) 0.184(2) 0.1483(14) 0.055(7) Uiso 1 1 d . . .
H1A H 0.090(4) 0.470(5) 0.025(3) 0.20(2) Uiso 1 1 d . . .
H1B H -0.037(4) 0.418(5) 0.049(4) 0.24(3) Uiso 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
N1 C16 1.337(2) . ?
N1 C16 1.337(2) 2 ?
N2 C1 1.339(2) . ?
N2 C13 1.407(2) . ?
N2 C14 1.483(2) . ?
C2 C3 1.399(3) . ?
C2 C7 1.411(3) . ?
C2 C1 1.436(3) . ?
N3 C1 1.331(2) . ?
N3 C8 1.387(3) . ?
N4 C7 1.375(2) . ?
N4 C14 1.452(3) . ?
C16 C17 1.385(3) . ?
C16 C14 1.540(2) . ?
C8 C9 1.387(3) . ?
C8 C13 1.390(3) . ?
C6 C5 1.375(3) . ?
C6 C7 1.392(3) . ?
C13 C12 1.391(3) . ?
C5 C4 1.383(3) . ?
C17 C18 1.376(2) . ?
C18 C17 1.376(2) 2 ?
C3 C4 1.367(3) . ?
C14 C15 1.520(3) . ?
C12 C11 1.372(3) . ?
C9 C10 1.386(3) . ?
C10 C11 1.397(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
C16 N1 C16 117.6(2) . 2 ?
C1 N2 C13 108.47(15) . . ?
C1 N2 C14 120.00(15) . . ?
C13 N2 C14 131.31(15) . . ?
C3 C2 C7 120.26(18) . . ?
C3 C2 C1 123.93(18) . . ?
C7 C2 C1 115.66(16) . . ?
C1 N3 C8 108.59(16) . . ?
N3 C1 N2 109.84(17) . . ?
N3 C1 C2 128.12(17) . . ?
N2 C1 C2 121.93(17) . . ?
C7 N4 C14 120.20(16) . . ?
N1 C16 C17 122.92(18) . . ?
N1 C16 C14 118.40(16) . . ?
C17 C16 C14 118.61(16) . . ?
C9 C8 N3 129.6(2) . . ?
C9 C8 C13 122.94(19) . . ?
N3 C8 C13 107.42(17) . . ?
C5 C6 C7 119.69(19) . . ?
N4 C7 C6 123.23(18) . . ?
N4 C7 C2 117.89(18) . . ?
C6 C7 C2 118.81(18) . . ?
C8 C13 C12 120.29(19) . . ?
C8 C13 N2 105.64(16) . . ?
C12 C13 N2 134.01(19) . . ?
C6 C5 C4 121.4(2) . . ?
C18 C17 C16 118.85(19) . . ?
C17 C18 C17 118.9(3) 2 . ?
C4 C3 C2 119.55(19) . . ?
N4 C14 N2 105.55(15) . . ?
N4 C14 C15 107.51(16) . . ?
N2 C14 C15 111.54(16) . . ?
N4 C14 C16 109.93(16) . . ?
N2 C14 C16 109.64(14) . . ?
C15 C14 C16 112.41(15) . . ?
C11 C12 C13 117.0(2) . . ?
C10 C9 C8 116.4(2) . . ?
C9 C10 C11 120.7(2) . . ?
C3 C4 C5 120.23(19) . . ?
C12 C11 C10 122.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        71.75
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.044

_database_code_depnum_ccdc_archive 'CCDC 959912'
#######################################################################
#
#                 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_dsrp_5_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H16 N4'
_chemical_formula_sum            'C20 H16 N4'
_chemical_melting_point          ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?

_diffrn_ambient_temperature      153(2)
_chemical_formula_weight         312.37

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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                   6.8611(3)
_cell_length_b                   12.8045(6)
_cell_length_c                   18.2363(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.863(3)
_cell_angle_gamma                90.00
_cell_volume                     1601.27(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29966
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         29.19
_reflns_number_total             4314
_reflns_number_gt                2809
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0770P)²+0.2047P] 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       0.0037(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4314
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1572
_refine_ls_wR_factor_gt          0.1363
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
C20 C 0.3328(2) 0.36915(14) 0.02433(9) 0.0541(4) Uani 1 1 d . . .
H20A H 0.3052 0.4350 0.0011 0.081 Uiso 1 1 calc R . .
H20B H 0.3776 0.3204 -0.0114 0.081 Uiso 1 1 calc R . .
H20C H 0.4319 0.3784 0.0621 0.081 Uiso 1 1 calc R . .
N3 N 0.18840(18) 0.24297(10) 0.11132(6) 0.0418(3) Uani 1 1 d . . .
N2 N 0.06049(19) 0.41178(10) 0.09916(7) 0.0452(3) Uani 1 1 d . . .
H21 H 0.1053 0.4744 0.0969 0.054 Uiso 1 1 calc R . .
N4 N 0.1178(2) 0.14387(10) 0.20907(7) 0.0525(4) Uani 1 1 d . . .
C13 C 0.0647(2) 0.22385(11) 0.16809(8) 0.0432(4) Uani 1 1 d . . .
C5 C 0.0066(2) 0.28729(11) -0.00351(7) 0.0388(3) Uani 1 1 d . . .
C19 C 0.3296(2) 0.16524(12) 0.11440(8) 0.0452(4) Uani 1 1 d . . .
N1 N -0.0765(2) 0.36226(10) -0.04464(7) 0.0524(4) Uani 1 1 d . . .
C6 C 0.1479(2) 0.32711(11) 0.05802(8) 0.0400(3) Uani 1 1 d . . .
C12 C -0.1016(2) 0.29169(13) 0.17753(8) 0.0465(4) Uani 1 1 d . . .
C7 C -0.0979(2) 0.38832(12) 0.14226(8) 0.0449(4) Uani 1 1 d . . .
C14 C 0.2828(3) 0.10574(13) 0.17681(9) 0.0508(4) Uani 1 1 d . . .
C8 C -0.2457(3) 0.46055(15) 0.15521(9) 0.0590(5) Uani 1 1 d . . .
H8 H -0.2422 0.5263 0.1336 0.071 Uiso 1 1 calc R . .
C4 C -0.0286(3) 0.18315(13) -0.01692(9) 0.0563(4) Uani 1 1 d . . .
H4 H 0.0322 0.1322 0.0120 0.068 Uiso 1 1 calc R . .
C1 C -0.1993(3) 0.33320(15) -0.09952(9) 0.0585(5) Uani 1 1 d . . .
H1 H -0.2579 0.3853 -0.1281 0.070 Uiso 1 1 calc R . .
C11 C -0.2574(3) 0.26636(16) 0.22167(10) 0.0623(5) Uani 1 1 d . . .
H11 H -0.2616 0.2014 0.2443 0.075 Uiso 1 1 calc R . .
C2 C -0.2437(3) 0.23181(14) -0.11597(9) 0.0573(5) Uani 1 1 d . . .
H2 H -0.3307 0.2152 -0.1544 0.069 Uiso 1 1 calc R . .
C15 C 0.3992(3) 0.02152(14) 0.19794(11) 0.0633(5) Uani 1 1 d . . .
H14 H 0.3724 -0.0170 0.2397 0.076 Uiso 1 1 calc R . .
C18 C 0.4849(3) 0.13929(15) 0.07173(11) 0.0613(5) Uani 1 1 d . . .
H17 H 0.5137 0.1775 0.0301 0.074 Uiso 1 1 calc R . .
C3 C -0.1559(3) 0.15519(14) -0.07412(10) 0.0655(5) Uani 1 1 d . . .
H3 H -0.1816 0.0852 -0.0840 0.079 Uiso 1 1 calc R . .
C16 C 0.5534(3) -0.00332(15) 0.15622(13) 0.0718(6) Uani 1 1 d . . .
H15 H 0.6321 -0.0597 0.1697 0.086 Uiso 1 1 calc R . .
C9 C -0.3954(3) 0.4350(2) 0.19959(11) 0.0718(6) Uani 1 1 d . . .
H9 H -0.4921 0.4839 0.2083 0.086 Uiso 1 1 calc R . .
C17 C 0.5963(3) 0.05366(17) 0.09377(13) 0.0722(6) Uani 1 1 d . . .
H16 H 0.7018 0.0339 0.0662 0.087 Uiso 1 1 calc R . .
C10 C -0.4048(3) 0.3374(2) 0.23170(11) 0.0741(6) Uani 1 1 d . . .
H10 H -0.5103 0.3199 0.2600 0.089 Uiso 1 1 calc R . .


_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
C20 C6 1.525(2) . ?
N3 C13 1.3817(19) . ?
N3 C19 1.3890(19) . ?
N3 C6 1.4715(18) . ?
N2 C7 1.394(2) . ?
N2 C6 1.4583(19) . ?
N4 C13 1.3123(19) . ?
N4 C14 1.382(2) . ?
C13 C12 1.449(2) . ?
C5 N1 1.3347(19) . ?
C5 C4 1.376(2) . ?
C5 C6 1.5451(19) . ?
C19 C18 1.380(2) . ?
C19 C14 1.415(2) . ?
N1 C1 1.340(2) . ?
C12 C7 1.395(2) . ?
C12 C11 1.397(2) . ?
C7 C8 1.398(2) . ?
C14 C15 1.389(2) . ?
C8 C9 1.368(3) . ?
C4 C3 1.386(2) . ?
C1 C2 1.365(3) . ?
C11 C10 1.377(3) . ?
C2 C3 1.370(3) . ?
C15 C16 1.361(3) . ?
C18 C17 1.388(3) . ?
C16 C17 1.392(3) . ?
C9 C10 1.382(3) . ?

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
C13 N3 C19 106.70(12) . . ?
C13 N3 C6 121.15(12) . . ?
C19 N3 C6 131.91(13) . . ?
C7 N2 C6 118.09(12) . . ?
C13 N4 C14 104.44(13) . . ?
N4 C13 N3 113.52(14) . . ?
N4 C13 C12 127.26(14) . . ?
N3 C13 C12 119.21(13) . . ?
N1 C5 C4 121.85(14) . . ?
N1 C5 C6 114.66(12) . . ?
C4 C5 C6 123.47(13) . . ?
C18 C19 N3 134.43(15) . . ?
C18 C19 C14 121.56(15) . . ?
N3 C19 C14 104.00(14) . . ?
C5 N1 C1 117.83(14) . . ?
N2 C6 N3 106.05(11) . . ?
N2 C6 C20 107.82(12) . . ?
N3 C6 C20 112.49(12) . . ?
N2 C6 C5 111.12(12) . . ?
N3 C6 C5 109.80(11) . . ?
C20 C6 C5 109.51(12) . . ?
C7 C12 C11 119.83(16) . . ?
C7 C12 C13 116.79(14) . . ?
C11 C12 C13 123.34(16) . . ?
N2 C7 C12 118.50(14) . . ?
N2 C7 C8 122.37(16) . . ?
C12 C7 C8 118.98(16) . . ?
N4 C14 C15 128.89(17) . . ?
N4 C14 C19 111.28(14) . . ?
C15 C14 C19 119.83(18) . . ?
C9 C8 C7 120.30(19) . . ?
C5 C4 C3 119.15(16) . . ?
N1 C1 C2 123.97(16) . . ?
C10 C11 C12 120.13(19) . . ?
C1 C2 C3 117.90(16) . . ?
C16 C15 C14 118.48(19) . . ?
C19 C18 C17 117.04(18) . . ?
C2 C3 C4 119.29(16) . . ?
C15 C16 C17 121.58(18) . . ?
C8 C9 C10 120.9(2) . . ?
C18 C17 C16 121.5(2) . . ?
C11 C10 C9 119.77(19) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.19
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.036

_database_code_depnum_ccdc_archive 'CCDC 959913'
