# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_is_ht2h182
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
6-(4-Methoxyphenyl)-6H-indolo[2,3-b]quinoxaline
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 N3 O'
_chemical_formula_sum            'C21 H15 N3 O'
_chemical_formula_weight         325.36

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.9259(3)
_cell_length_b                   11.0893(6)
_cell_length_c                   12.3340(6)
_cell_angle_alpha                79.323(3)
_cell_angle_beta                 78.333(3)
_cell_angle_gamma                86.450(3)
_cell_volume                     779.78(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1942
_cell_measurement_theta_min      6.854
_cell_measurement_theta_max      45.116

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9632
_exptl_absorpt_correction_T_max  0.9974
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18870
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_sigmaI/netI    0.0993
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         29.00
_reflns_number_total             4102
_reflns_number_gt                2135
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine.
 
 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 > 2σ(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)+(0.0505P)²+0.0944P] 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       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4102
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1439
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1320
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.2420(3) 0.12410(15) 0.09797(14) 0.0232(4) Uani 1 1 d . . .
N2 N 0.0426(3) 0.11353(16) 0.33439(14) 0.0244(4) Uani 1 1 d . . .
N3 N -0.0890(3) 0.25295(15) 0.07153(14) 0.0236(4) Uani 1 1 d . . .
O1 O 0.0226(3) 0.37873(14) -0.39413(12) 0.0331(4) Uani 1 1 d . . .
C1 C 0.0507(3) 0.18081(18) 0.13579(16) 0.0220(5) Uani 1 1 d . . .
C2 C -0.0500(3) 0.17767(18) 0.25291(16) 0.0211(5) Uani 1 1 d . . .
C3 C -0.2580(3) 0.25272(18) 0.25658(17) 0.0232(5) Uani 1 1 d . . .
C4 C -0.2761(4) 0.29687(18) 0.14454(17) 0.0246(5) Uani 1 1 d . . .
C5 C 0.3452(4) 0.05910(18) 0.18257(17) 0.0227(5) Uani 1 1 d . . .
C6 C 0.5573(4) -0.00285(18) 0.15323(18) 0.0248(5) Uani 1 1 d . . .
H6 H 0.6249 -0.0001 0.0761 0.030 Uiso 1 1 calc R . .
C7 C 0.6666(4) -0.06664(18) 0.23379(18) 0.0262(5) Uani 1 1 d . . .
H7 H 0.8109 -0.1066 0.2124 0.031 Uiso 1 1 calc R . .
C8 C 0.5676(4) -0.0739(2) 0.34875(18) 0.0296(5) Uani 1 1 d . . .
H8 H 0.6449 -0.1192 0.4044 0.036 Uiso 1 1 calc R . .
C9 C 0.3605(4) -0.01595(19) 0.38038(18) 0.0271(5) Uani 1 1 d . . .
H9 H 0.2936 -0.0222 0.4579 0.032 Uiso 1 1 calc R . .
C10 C 0.2455(3) 0.05292(18) 0.29887(17) 0.0222(5) Uani 1 1 d . . .
C11 C -0.4584(4) 0.37198(19) 0.11680(19) 0.0289(5) Uani 1 1 d . . .
H11 H -0.4706 0.4000 0.0405 0.035 Uiso 1 1 calc R . .
C12 C -0.6225(4) 0.4050(2) 0.2039(2) 0.0351(6) Uani 1 1 d . . .
H12 H -0.7489 0.4571 0.1872 0.042 Uiso 1 1 calc R . .
C13 C -0.6056(4) 0.3629(2) 0.3160(2) 0.0353(6) Uani 1 1 d . . .
H13 H -0.7194 0.3876 0.3744 0.042 Uiso 1 1 calc R . .
C14 C -0.4257(4) 0.28609(19) 0.34281(18) 0.0284(5) Uani 1 1 d . . .
H14 H -0.4165 0.2564 0.4192 0.034 Uiso 1 1 calc R . .
C15 C -0.0575(4) 0.27980(18) -0.04866(17) 0.0222(5) Uani 1 1 d . . .
C16 C 0.1272(4) 0.34846(19) -0.11196(18) 0.0269(5) Uani 1 1 d . . .
H16 H 0.2380 0.3747 -0.0760 0.032 Uiso 1 1 calc R . .
C17 C 0.1498(4) 0.37858(19) -0.22718(17) 0.0272(5) Uani 1 1 d . . .
H17 H 0.2772 0.4249 -0.2705 0.033 Uiso 1 1 calc R . .
C18 C -0.0129(4) 0.34146(18) -0.27995(17) 0.0232(5) Uani 1 1 d . . .
C19 C -0.1971(4) 0.27274(18) -0.21743(17) 0.0248(5) Uani 1 1 d . . .
H19 H -0.3079 0.2466 -0.2535 0.030 Uiso 1 1 calc R . .
C20 C -0.2185(4) 0.24232(18) -0.10160(17) 0.0250(5) Uani 1 1 d . . .
H20 H -0.3450 0.1953 -0.0583 0.030 Uiso 1 1 calc R . .
C21 C -0.1427(4) 0.3423(2) -0.45119(18) 0.0372(6) Uani 1 1 d . . .
H21A H -0.1340 0.2529 -0.4460 0.056 Uiso 1 1 calc R . .
H21B H -0.1094 0.3818 -0.5305 0.056 Uiso 1 1 calc R . .
H21C H -0.2979 0.3672 -0.4162 0.056 Uiso 1 1 calc R . .


#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.306(3) . ?
N1 C5 1.381(2) . ?
N2 C2 1.314(2) . ?
N2 C10 1.373(3) . ?
N3 C1 1.379(2) . ?
N3 C4 1.403(3) . ?
N3 C15 1.433(2) . ?
O1 C18 1.369(2) . ?
O1 C21 1.433(2) . ?
C1 C2 1.442(3) . ?
C2 C3 1.441(3) . ?
C3 C14 1.389(3) . ?
C3 C4 1.401(3) . ?
C4 C11 1.382(3) . ?
C5 C6 1.408(3) . ?
C5 C10 1.427(3) . ?
C6 C7 1.360(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.410(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.369(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.409(3) . ?
C9 H9 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.397(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C20 1.383(3) . ?
C15 C16 1.387(3) . ?
C16 C17 1.379(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(3) . ?
C19 C20 1.387(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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 113.10(17) . . ?
C2 N2 C10 114.57(17) . . ?
C1 N3 C4 108.15(16) . . ?
C1 N3 C15 127.67(17) . . ?
C4 N3 C15 124.18(17) . . ?
C18 O1 C21 116.93(16) . . ?
N1 C1 N3 126.22(18) . . ?
N1 C1 C2 125.21(19) . . ?
N3 C1 C2 108.57(17) . . ?
N2 C2 C3 130.76(19) . . ?
N2 C2 C1 122.42(19) . . ?
C3 C2 C1 106.81(17) . . ?
C14 C3 C4 119.49(19) . . ?
C14 C3 C2 134.2(2) . . ?
C4 C3 C2 106.35(17) . . ?
C11 C4 C3 121.89(19) . . ?
C11 C4 N3 127.98(19) . . ?
C3 C4 N3 110.13(18) . . ?
N1 C5 C6 118.89(18) . . ?
N1 C5 C10 122.43(18) . . ?
C6 C5 C10 118.67(19) . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.6(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.6(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
N2 C10 C9 118.65(19) . . ?
N2 C10 C5 122.22(18) . . ?
C9 C10 C5 119.13(19) . . ?
C4 C11 C12 117.7(2) . . ?
C4 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
C11 C12 C13 121.1(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C3 119.1(2) . . ?
C13 C14 H14 120.5 . . ?
C3 C14 H14 120.5 . . ?
C20 C15 C16 119.69(19) . . ?
C20 C15 N3 119.77(18) . . ?
C16 C15 N3 120.46(18) . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
O1 C18 C19 124.32(19) . . ?
O1 C18 C17 115.51(18) . . ?
C19 C18 C17 120.16(19) . . ?
C18 C19 C20 119.4(2) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C15 C20 C19 120.60(19) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C5 N1 C1 N3 179.70(19) . . . . ?
C5 N1 C1 C2 -0.5(3) . . . . ?
C4 N3 C1 N1 -179.79(19) . . . . ?
C15 N3 C1 N1 0.9(3) . . . . ?
C4 N3 C1 C2 0.4(2) . . . . ?
C15 N3 C1 C2 -178.88(18) . . . . ?
C10 N2 C2 C3 -179.6(2) . . . . ?
C10 N2 C2 C1 1.7(3) . . . . ?
N1 C1 C2 N2 -1.4(3) . . . . ?
N3 C1 C2 N2 178.46(19) . . . . ?
N1 C1 C2 C3 179.72(19) . . . . ?
N3 C1 C2 C3 -0.5(2) . . . . ?
N2 C2 C3 C14 1.9(4) . . . . ?
C1 C2 C3 C14 -179.3(2) . . . . ?
N2 C2 C3 C4 -178.4(2) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C14 C3 C4 C11 -0.8(3) . . . . ?
C2 C3 C4 C11 179.51(19) . . . . ?
C14 C3 C4 N3 179.57(18) . . . . ?
C2 C3 C4 N3 -0.1(2) . . . . ?
C1 N3 C4 C11 -179.8(2) . . . . ?
C15 N3 C4 C11 -0.5(3) . . . . ?
C1 N3 C4 C3 -0.2(2) . . . . ?
C15 N3 C4 C3 179.13(17) . . . . ?
C1 N1 C5 C6 -177.78(18) . . . . ?
C1 N1 C5 C10 1.8(3) . . . . ?
N1 C5 C6 C7 179.11(18) . . . . ?
C10 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C8 1.1(3) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C7 C8 C9 C10 -0.9(3) . . . . ?
C2 N2 C10 C9 178.52(19) . . . . ?
C2 N2 C10 C5 -0.4(3) . . . . ?
C8 C9 C10 N2 -177.49(19) . . . . ?
C8 C9 C10 C5 1.5(3) . . . . ?
N1 C5 C10 N2 -1.4(3) . . . . ?
C6 C5 C10 N2 178.15(18) . . . . ?
N1 C5 C10 C9 179.61(19) . . . . ?
C6 C5 C10 C9 -0.8(3) . . . . ?
C3 C4 C11 C12 1.3(3) . . . . ?
N3 C4 C11 C12 -179.1(2) . . . . ?
C4 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C13 C14 C3 1.3(3) . . . . ?
C4 C3 C14 C13 -0.5(3) . . . . ?
C2 C3 C14 C13 179.0(2) . . . . ?
C1 N3 C15 C20 117.1(2) . . . . ?
C4 N3 C15 C20 -62.1(3) . . . . ?
C1 N3 C15 C16 -66.2(3) . . . . ?
C4 N3 C15 C16 114.7(2) . . . . ?
C20 C15 C16 C17 -0.2(3) . . . . ?
N3 C15 C16 C17 -176.98(18) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C21 O1 C18 C19 -0.6(3) . . . . ?
C21 O1 C18 C17 -179.80(19) . . . . ?
C16 C17 C18 O1 178.46(18) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
O1 C18 C19 C20 -178.62(18) . . . . ?
C17 C18 C19 C20 0.6(3) . . . . ?
C16 C15 C20 C19 0.0(3) . . . . ?
N3 C15 C20 C19 176.77(17) . . . . ?
C18 C19 C20 C15 -0.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.057
_database_code_depnum_ccdc_archive 'CCDC 997724'
#######################################################################
#
#                 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_is_ht3h053
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
6-(3-Phenylpropyl)-6H-indolo[2,3-b]quinoxaline
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 N3'
_chemical_formula_sum            'C23 H19 N3'
_chemical_formula_weight         337.41

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'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3149(3)
_cell_length_b                   15.0792(8)
_cell_length_c                   16.8977(8)
_cell_angle_alpha                72.116(2)
_cell_angle_beta                 88.582(2)
_cell_angle_gamma                77.750(2)
_cell_volume                     1731.78(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6449
_cell_measurement_theta_min      4.408
_cell_measurement_theta_max      50.154

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.99
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9273
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            44254
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         29.50
_reflns_number_total             9574
_reflns_number_gt                5369
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). The geometry of 
 the disordered parts was constrained to be equal (esd 0.01). The Uij of the 
 atoms a/b of both parts were constrained to be equal.
 
 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 > 2σ(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)+(0.0647P)²+0.1010P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9574
_refine_ls_number_parameters     482
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1450
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.76880(15) 1.11750(9) 0.53939(7) 0.0295(3) Uani 1 1 d . . .
N2 N 0.64164(16) 1.15051(9) 0.36995(7) 0.0305(3) Uani 1 1 d . . .
N3 N 0.68760(16) 0.98155(9) 0.41242(7) 0.0292(3) Uani 1 1 d . . .
C1 C 0.69061(18) 1.06625(10) 0.42552(8) 0.0270(3) Uani 1 1 d . . .
C2 C 0.75366(17) 1.04815(10) 0.51023(8) 0.0262(3) Uani 1 1 d . . .
C3 C 0.78769(18) 0.94617(10) 0.54863(8) 0.0271(3) Uani 1 1 d . . .
C4 C 0.74542(18) 0.90803(10) 0.48674(8) 0.0279(3) Uani 1 1 d . . .
C5 C 0.7627(2) 0.81064(11) 0.50297(9) 0.0337(4) Uani 1 1 d . . .
H5 H 0.7345 0.7851 0.4610 0.040 Uiso 1 1 calc R . .
C6 C 0.8224(2) 0.75221(11) 0.58213(9) 0.0373(4) Uani 1 1 d . . .
H6 H 0.8349 0.6853 0.5946 0.045 Uiso 1 1 calc R . .
C7 C 0.8648(2) 0.78810(12) 0.64437(10) 0.0377(4) Uani 1 1 d . . .
H7 H 0.9049 0.7458 0.6984 0.045 Uiso 1 1 calc R . .
C8 C 0.84896(19) 0.88498(11) 0.62810(9) 0.0328(4) Uani 1 1 d . . .
H8 H 0.8793 0.9096 0.6703 0.039 Uiso 1 1 calc R . .
C9 C 0.65661(19) 1.22363(11) 0.39980(9) 0.0311(3) Uani 1 1 d . . .
C10 C 0.6053(2) 1.31811(11) 0.34619(10) 0.0389(4) Uani 1 1 d . . .
H10 H 0.5597 1.3298 0.2910 0.047 Uiso 1 1 calc R . .
C11 C 0.6208(2) 1.39268(12) 0.37317(10) 0.0451(4) Uani 1 1 d . . .
H11 H 0.5862 1.4560 0.3364 0.054 Uiso 1 1 calc R . .
C12 C 0.6871(2) 1.37725(12) 0.45461(10) 0.0437(4) Uani 1 1 d . . .
H12 H 0.6984 1.4300 0.4723 0.052 Uiso 1 1 calc R . .
C13 C 0.7355(2) 1.28656(11) 0.50860(10) 0.0369(4) Uani 1 1 d . . .
H13 H 0.7793 1.2767 0.5637 0.044 Uiso 1 1 calc R . .
C14 C 0.72078(19) 1.20771(11) 0.48300(9) 0.0303(3) Uani 1 1 d . . .
C15 C 0.61646(19) 0.97427(11) 0.33523(8) 0.0339(4) Uani 1 1 d . . .
H15A H 0.5090 1.0283 0.3124 0.041 Uiso 1 1 calc R . .
H15B H 0.5702 0.9145 0.3478 0.041 Uiso 1 1 calc R . .
C16 C 0.7631(2) 0.97494(11) 0.26922(9) 0.0358(4) Uani 1 1 d . . .
H16A H 0.6994 0.9858 0.2150 0.043 Uiso 1 1 calc R . .
H16B H 0.8248 1.0288 0.2637 0.043 Uiso 1 1 calc R . .
C17 C 0.9114(2) 0.88333(11) 0.28888(9) 0.0381(4) Uani 1 1 d . . .
H17A H 0.9774 0.8734 0.3424 0.046 Uiso 1 1 calc R . .
H17B H 0.8493 0.8292 0.2960 0.046 Uiso 1 1 calc R . .
C18 C 1.0539(2) 0.88270(11) 0.22249(9) 0.0344(4) Uani 1 1 d . . .
C19 C 1.0000(2) 0.89191(12) 0.14166(10) 0.0446(4) Uani 1 1 d . . .
H19 H 0.8713 0.8996 0.1278 0.054 Uiso 1 1 calc R . .
C20 C 1.1296(2) 0.89017(12) 0.08078(10) 0.0450(4) Uani 1 1 d . . .
H20 H 1.0898 0.8971 0.0257 0.054 Uiso 1 1 calc R . .
C21 C 1.3166(2) 0.87831(11) 0.10057(11) 0.0442(4) Uani 1 1 d . . .
H21 H 1.4067 0.8761 0.0594 0.053 Uiso 1 1 calc R . .
C22 C 1.3724(2) 0.86969(12) 0.18013(11) 0.0449(4) Uani 1 1 d . . .
H22 H 1.5013 0.8615 0.1938 0.054 Uiso 1 1 calc R . .
C23 C 1.2421(2) 0.87283(11) 0.24050(10) 0.0395(4) Uani 1 1 d . . .
H23 H 1.2823 0.8682 0.2949 0.047 Uiso 1 1 calc R . .
N4 N 0.79392(15) 0.60009(8) 1.04090(7) 0.0271(3) Uani 1 1 d . . .
N5 N 0.67162(16) 0.62779(9) 0.87178(7) 0.0294(3) Uani 1 1 d . . .
N6 N 0.68422(16) 0.46022(8) 0.92268(7) 0.0287(3) Uani 1 1 d . A .
C24 C 0.70473(18) 0.54545(10) 0.93058(8) 0.0259(3) Uani 1 1 d . . .
C25 C 0.76624(18) 0.53014(10) 1.01524(8) 0.0247(3) Uani 1 1 d . . .
C26 C 0.78237(18) 0.42978(10) 1.05850(8) 0.0262(3) Uani 1 1 d . . .
C27 C 0.73047(18) 0.38980(10) 0.99952(8) 0.0270(3) Uani 1 1 d . . .
C28 C 0.72787(19) 0.29384(11) 1.01997(9) 0.0329(3) Uani 1 1 d . . .
H28 H 0.6936 0.2674 0.9797 0.040 Uiso 1 1 calc R . .
C29 C 0.7770(2) 0.23824(11) 1.10108(10) 0.0368(4) Uani 1 1 d . . .
H29 H 0.7772 0.1721 1.1167 0.044 Uiso 1 1 calc R . .
C30 C 0.8262(2) 0.27612(11) 1.16050(9) 0.0366(4) Uani 1 1 d . . .
H30 H 0.8578 0.2358 1.2160 0.044 Uiso 1 1 calc R . .
C31 C 0.82977(19) 0.37174(11) 1.14007(9) 0.0315(3) Uani 1 1 d . . .
H31 H 0.8640 0.3974 1.1809 0.038 Uiso 1 1 calc R . .
C32 C 0.69884(18) 0.70155(10) 0.89824(8) 0.0280(3) Uani 1 1 d . . .
C33 C 0.6613(2) 0.79447(11) 0.84124(9) 0.0348(4) Uani 1 1 d . . .
H33 H 0.6193 0.8045 0.7858 0.042 Uiso 1 1 calc R . .
C34 C 0.6849(2) 0.86985(11) 0.86508(10) 0.0398(4) Uani 1 1 d . . .
H34 H 0.6607 0.9320 0.8259 0.048 Uiso 1 1 calc R . .
C35 C 0.7447(2) 0.85688(11) 0.94697(10) 0.0414(4) Uani 1 1 d . . .
H35 H 0.7598 0.9102 0.9628 0.050 Uiso 1 1 calc R . .
C36 C 0.7813(2) 0.76787(11) 1.00394(9) 0.0339(4) Uani 1 1 d . . .
H36 H 0.8221 0.7597 1.0592 0.041 Uiso 1 1 calc R . .
C37 C 0.75909(18) 0.68811(10) 0.98154(8) 0.0279(3) Uani 1 1 d . . .
C38 C 0.6093(2) 0.44678(12) 0.84928(9) 0.0346(4) Uani 1 1 d D . .
H38A H 0.5416 0.5093 0.8124 0.042 Uiso 0.8965(19) 1 calc PR A 1
H38B H 0.5180 0.4052 0.8666 0.042 Uiso 0.8965(19) 1 calc PR A 1
H38C H 0.4999 0.4994 0.8258 0.042 Uiso 0.1035(19) 1 d PR A 2
H38D H 0.5656 0.3861 0.8653 0.042 Uiso 0.1035(19) 1 d PR A 2
C39A C 0.7600(2) 0.40243(12) 0.80067(10) 0.0317(4) Uani 0.8965(19) 1 d PD A 1
H39A H 0.8318 0.3412 0.8380 0.038 Uiso 0.8965(19) 1 calc PR A 1
H39B H 0.6999 0.3888 0.7551 0.038 Uiso 0.8965(19) 1 calc PR A 1
C40A C 0.8934(2) 0.46789(12) 0.76404(10) 0.0370(4) Uani 0.8965(19) 1 d PD A 1
H40A H 0.8203 0.5308 0.7302 0.044 Uiso 0.8965(19) 1 calc PR A 1
H40B H 0.9603 0.4776 0.8099 0.044 Uiso 0.8965(19) 1 calc PR A 1
C41A C 1.0346(2) 0.42811(13) 0.71051(10) 0.0314(4) Uani 0.8965(19) 1 d PD A 1
C42A C 0.9841(3) 0.43232(14) 0.63098(10) 0.0380(5) Uani 0.8965(19) 1 d PD A 1
H42A H 0.8589 0.4606 0.6102 0.046 Uiso 0.8965(19) 1 calc PR A 1
C43A C 1.1118(4) 0.3963(2) 0.58104(14) 0.0464(7) Uani 0.8965(19) 1 d PD A 1
H43A H 1.0740 0.3994 0.5267 0.056 Uiso 0.8965(19) 1 calc PR A 1
C44A C 1.2931(4) 0.3560(4) 0.6100(2) 0.0510(6) Uani 0.8965(19) 1 d PD A 1
H44A H 1.3821 0.3324 0.5754 0.061 Uiso 0.8965(19) 1 calc PR A 1
C45A C 1.3456(3) 0.3497(3) 0.6893(2) 0.0519(5) Uani 0.8965(19) 1 d PD A 1
H45A H 1.4710 0.3209 0.7097 0.062 Uiso 0.8965(19) 1 calc PR A 1
C46A C 1.2175(3) 0.38507(14) 0.73985(15) 0.0423(6) Uani 0.8965(19) 1 d PD A 1
H46A H 1.2550 0.3798 0.7948 0.051 Uiso 0.8965(19) 1 calc PR A 1
C39B C 0.7481(16) 0.4638(9) 0.7763(7) 0.0317(4) Uani 0.1035(19) 1 d PD A 2
H39C H 0.6812 0.4760 0.7226 0.038 Uiso 0.1035(19) 1 calc PR A 2
H39D H 0.8009 0.5199 0.7735 0.038 Uiso 0.1035(19) 1 calc PR A 2
C40B C 0.9038(18) 0.3751(9) 0.7930(7) 0.0370(4) Uani 0.1035(19) 1 d PD A 2
H40C H 0.9763 0.3687 0.8439 0.044 Uiso 0.1035(19) 1 calc PR A 2
H40D H 0.8460 0.3190 0.8049 0.044 Uiso 0.1035(19) 1 calc PR A 2
C41B C 1.0382(14) 0.3718(10) 0.7249(6) 0.0314(4) Uani 0.1035(19) 1 d PGD A 2
C42B C 0.9721(19) 0.3826(11) 0.6453(7) 0.0380(5) Uani 0.1035(19) 1 d PGD A 2
H42B H 0.8414 0.3936 0.6337 0.046 Uiso 0.1035(19) 1 calc PR A 2
C43B C 1.097(3) 0.377(2) 0.5828(9) 0.0464(7) Uani 0.1035(19) 1 d PGD A 2
H43B H 1.0520 0.3848 0.5284 0.056 Uiso 0.1035(19) 1 calc PR A 2
C44B C 1.288(3) 0.361(3) 0.5999(15) 0.0510(6) Uani 0.1035(19) 1 d PGD A 2
H44B H 1.3739 0.3578 0.5572 0.061 Uiso 0.1035(19) 1 calc PR A 2
C45B C 1.3546(16) 0.351(3) 0.6794(17) 0.0519(5) Uani 0.1035(19) 1 d PGD A 2
H45B H 1.4853 0.3396 0.6911 0.062 Uiso 0.1035(19) 1 calc PR A 2
C46B C 1.2295(15) 0.3557(16) 0.7420(11) 0.0423(6) Uani 0.1035(19) 1 d PGD A 2
H46B H 1.2747 0.3483 0.7963 0.051 Uiso 0.1035(19) 1 calc PR A 2


#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.3103(17) . ?
N1 C14 1.3782(18) . ?
N2 C1 1.3097(18) . ?
N2 C9 1.3703(18) . ?
N3 C1 1.3663(18) . ?
N3 C4 1.3990(18) . ?
N3 C15 1.4594(17) . ?
C1 C2 1.4406(19) . ?
C2 C3 1.442(2) . ?
C3 C8 1.3960(19) . ?
C3 C4 1.407(2) . ?
C4 C5 1.387(2) . ?
C5 C6 1.378(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.410(2) . ?
C9 C14 1.425(2) . ?
C10 C11 1.363(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.404(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.368(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.409(2) . ?
C13 H13 0.9500 . ?
C15 C16 1.528(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.515(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.513(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C23 1.384(2) . ?
C18 C19 1.388(2) . ?
C19 C20 1.384(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.378(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.374(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
N4 C25 1.3106(17) . ?
N4 C37 1.3726(18) . ?
N5 C24 1.3093(17) . ?
N5 C32 1.3714(18) . ?
N6 C24 1.3711(18) . ?
N6 C27 1.3966(17) . ?
N6 C38 1.4543(17) . ?
C24 C25 1.4447(19) . ?
C25 C26 1.445(2) . ?
C26 C31 1.3927(19) . ?
C26 C27 1.409(2) . ?
C27 C28 1.385(2) . ?
C28 C29 1.379(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.382(2) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C33 1.410(2) . ?
C32 C37 1.4262(19) . ?
C33 C34 1.361(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.404(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.366(2) . ?
C35 H35 0.9500 . ?
C36 C37 1.408(2) . ?
C36 H36 0.9500 . ?
C38 C39A 1.522(2) . ?
C38 C39B 1.572(8) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C38 H38C 0.9900 . ?
C38 H38D 0.9900 . ?
C39A C40A 1.521(2) . ?
C39A H39A 0.9900 . ?
C39A H39B 0.9900 . ?
C40A C41A 1.506(2) . ?
C40A H40A 0.9900 . ?
C40A H40B 0.9900 . ?
C41A C42A 1.381(2) . ?
C41A C46A 1.387(2) . ?
C42A C43A 1.381(3) . ?
C42A H42A 0.9500 . ?
C43A C44A 1.369(3) . ?
C43A H43A 0.9500 . ?
C44A C45A 1.372(3) . ?
C44A H44A 0.9500 . ?
C45A C46A 1.386(3) . ?
C45A H45A 0.9500 . ?
C46A H46A 0.9500 . ?
C39B C40B 1.517(9) . ?
C39B H39C 0.9900 . ?
C39B H39D 0.9900 . ?
C40B C41B 1.500(8) . ?
C40B H40C 0.9900 . ?
C40B H40D 0.9900 . ?
C41B C42B 1.3900 . ?
C41B C46B 1.3900 . ?
C42B C43B 1.3900 . ?
C42B H42B 0.9500 . ?
C43B C44B 1.3900 . ?
C43B H43B 0.9500 . ?
C44B C45B 1.3900 . ?
C44B H44B 0.9500 . ?
C45B C46B 1.3900 . ?
C45B H45B 0.9500 . ?
C46B H46B 0.9500 . ?

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 N1 C14 114.92(12) . . ?
C1 N2 C9 113.15(12) . . ?
C1 N3 C4 108.26(11) . . ?
C1 N3 C15 123.64(12) . . ?
C4 N3 C15 127.83(12) . . ?
N2 C1 N3 125.21(13) . . ?
N2 C1 C2 125.55(13) . . ?
N3 C1 C2 109.24(12) . . ?
N1 C2 C1 121.81(13) . . ?
N1 C2 C3 131.86(12) . . ?
C1 C2 C3 106.33(12) . . ?
C8 C3 C4 119.55(14) . . ?
C8 C3 C2 134.22(14) . . ?
C4 C3 C2 106.22(12) . . ?
C5 C4 N3 128.63(13) . . ?
C5 C4 C3 121.42(13) . . ?
N3 C4 C3 109.95(13) . . ?
C6 C5 C4 117.63(14) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
C5 C6 C7 122.07(15) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C8 C7 C6 120.34(14) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C3 118.99(14) . . ?
C7 C8 H8 120.5 . . ?
C3 C8 H8 120.5 . . ?
N2 C9 C10 118.59(13) . . ?
N2 C9 C14 122.47(13) . . ?
C10 C9 C14 118.94(14) . . ?
C11 C10 C9 120.35(15) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.91(15) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 120.22(15) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.47(15) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
N1 C14 C13 118.83(13) . . ?
N1 C14 C9 122.09(13) . . ?
C13 C14 C9 119.08(14) . . ?
N3 C15 C16 113.33(12) . . ?
N3 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
N3 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C15 113.43(12) . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 113.57(12) . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C23 C18 C19 117.94(14) . . ?
C23 C18 C17 121.02(13) . . ?
C19 C18 C17 121.04(14) . . ?
C20 C19 C18 121.48(16) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C21 C20 C19 119.55(15) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 C21 C20 119.76(15) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.50(16) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 120.75(15) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
C25 N4 C37 114.91(11) . . ?
C24 N5 C32 113.20(12) . . ?
C24 N6 C27 108.49(11) . . ?
C24 N6 C38 125.87(12) . . ?
C27 N6 C38 125.38(12) . . ?
N5 C24 N6 125.97(12) . . ?
N5 C24 C25 125.20(13) . . ?
N6 C24 C25 108.82(12) . . ?
N4 C25 C24 122.00(13) . . ?
N4 C25 C26 131.47(12) . . ?
C24 C25 C26 106.52(12) . . ?
C31 C26 C27 119.30(13) . . ?
C31 C26 C25 134.60(13) . . ?
C27 C26 C25 106.08(12) . . ?
C28 C27 N6 128.05(13) . . ?
C28 C27 C26 121.86(13) . . ?
N6 C27 C26 110.09(12) . . ?
C29 C28 C27 117.36(14) . . ?
C29 C28 H28 121.3 . . ?
C27 C28 H28 121.3 . . ?
C28 C29 C30 121.87(15) . . ?
C28 C29 H29 119.1 . . ?
C30 C29 H29 119.1 . . ?
C31 C30 C29 120.83(14) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C30 C31 C26 118.78(14) . . ?
C30 C31 H31 120.6 . . ?
C26 C31 H31 120.6 . . ?
N5 C32 C33 118.52(13) . . ?
N5 C32 C37 122.54(13) . . ?
C33 C32 C37 118.92(14) . . ?
C34 C33 C32 120.46(14) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 120.78(15) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 H34 119.6 . . ?
C36 C35 C34 120.29(15) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C35 C36 C37 120.58(14) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 H36 119.7 . . ?
N4 C37 C36 118.88(13) . . ?
N4 C37 C32 122.15(13) . . ?
C36 C37 C32 118.96(13) . . ?
N6 C38 C39A 112.97(12) . . ?
N6 C38 C39B 110.8(6) . . ?
C39A C38 C39B 32.8(5) . . ?
N6 C38 H38A 109.0 . . ?
C39A C38 H38A 109.0 . . ?
C39B C38 H38A 79.7 . . ?
N6 C38 H38B 109.0 . . ?
C39A C38 H38B 109.0 . . ?
C39B C38 H38B 134.1 . . ?
H38A C38 H38B 107.8 . . ?
N6 C38 H38C 108.8 . . ?
C39A C38 H38C 126.7 . . ?
C39B C38 H38C 101.5 . . ?
H38A C38 H38C 23.5 . . ?
H38B C38 H38C 86.3 . . ?
N6 C38 H38D 109.6 . . ?
C39A C38 H38D 87.9 . . ?
C39B C38 H38D 117.7 . . ?
H38A C38 H38D 126.7 . . ?
H38B C38 H38D 23.7 . . ?
H38C C38 H38D 107.8 . . ?
C40A C39A C38 111.75(14) . . ?
C40A C39A H39A 109.3 . . ?
C38 C39A H39A 109.3 . . ?
C40A C39A H39B 109.3 . . ?
C38 C39A H39B 109.3 . . ?
H39A C39A H39B 107.9 . . ?
C41A C40A C39A 112.31(14) . . ?
C41A C40A H40A 109.1 . . ?
C39A C40A H40A 109.1 . . ?
C41A C40A H40B 109.1 . . ?
C39A C40A H40B 109.1 . . ?
H40A C40A H40B 107.9 . . ?
C42A C41A C46A 118.16(16) . . ?
C42A C41A C40A 120.66(15) . . ?
C46A C41A C40A 121.17(16) . . ?
C43A C42A C41A 121.40(18) . . ?
C43A C42A H42A 119.3 . . ?
C41A C42A H42A 119.3 . . ?
C44A C43A C42A 119.88(19) . . ?
C44A C43A H43A 120.1 . . ?
C42A C43A H43A 120.1 . . ?
C43A C44A C45A 119.70(18) . . ?
C43A C44A H44A 120.2 . . ?
C45A C44A H44A 120.2 . . ?
C44A C45A C46A 120.58(18) . . ?
C44A C45A H45A 119.7 . . ?
C46A C45A H45A 119.7 . . ?
C45A C46A C41A 120.26(18) . . ?
C45A C46A H46A 119.9 . . ?
C41A C46A H46A 119.9 . . ?
C40B C39B C38 108.1(8) . . ?
C40B C39B H39C 110.1 . . ?
C38 C39B H39C 110.1 . . ?
C40B C39B H39D 110.1 . . ?
C38 C39B H39D 110.1 . . ?
H39C C39B H39D 108.4 . . ?
C41B C40B C39B 116.5(9) . . ?
C41B C40B H40C 108.2 . . ?
C39B C40B H40C 108.2 . . ?
C41B C40B H40D 108.2 . . ?
C39B C40B H40D 108.2 . . ?
H40C C40B H40D 107.3 . . ?
C42B C41B C46B 120.0 . . ?
C42B C41B C40B 120.1(8) . . ?
C46B C41B C40B 119.9(8) . . ?
C43B C42B C41B 120.0 . . ?
C43B C42B H42B 120.0 . . ?
C41B C42B H42B 120.0 . . ?
C42B C43B C44B 120.0 . . ?
C42B C43B H43B 120.0 . . ?
C44B C43B H43B 120.0 . . ?
C43B C44B C45B 120.0 . . ?
C43B C44B H44B 120.0 . . ?
C45B C44B H44B 120.0 . . ?
C46B C45B C44B 120.0 . . ?
C46B C45B H45B 120.0 . . ?
C44B C45B H45B 120.0 . . ?
C45B C46B C41B 120.0 . . ?
C45B C46B H46B 120.0 . . ?
C41B C46B H46B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N2 C1 N3 179.48(12) . . . . ?
C9 N2 C1 C2 0.35(19) . . . . ?
C4 N3 C1 N2 -178.67(12) . . . . ?
C15 N3 C1 N2 -4.3(2) . . . . ?
C4 N3 C1 C2 0.58(14) . . . . ?
C15 N3 C1 C2 174.94(11) . . . . ?
C14 N1 C2 C1 -0.24(18) . . . . ?
C14 N1 C2 C3 -179.24(13) . . . . ?
N2 C1 C2 N1 -0.5(2) . . . . ?
N3 C1 C2 N1 -179.73(11) . . . . ?
N2 C1 C2 C3 178.74(12) . . . . ?
N3 C1 C2 C3 -0.51(14) . . . . ?
N1 C2 C3 C8 -0.7(3) . . . . ?
C1 C2 C3 C8 -179.82(14) . . . . ?
N1 C2 C3 C4 179.35(14) . . . . ?
C1 C2 C3 C4 0.24(14) . . . . ?
C1 N3 C4 C5 179.53(13) . . . . ?
C15 N3 C4 C5 5.5(2) . . . . ?
C1 N3 C4 C3 -0.43(15) . . . . ?
C15 N3 C4 C3 -174.49(12) . . . . ?
C8 C3 C4 C5 0.2(2) . . . . ?
C2 C3 C4 C5 -179.86(12) . . . . ?
C8 C3 C4 N3 -179.85(11) . . . . ?
C2 C3 C4 N3 0.10(14) . . . . ?
N3 C4 C5 C6 -179.73(13) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C6 C7 C8 C3 0.7(2) . . . . ?
C4 C3 C8 C7 -0.7(2) . . . . ?
C2 C3 C8 C7 179.39(14) . . . . ?
C1 N2 C9 C10 -179.10(12) . . . . ?
C1 N2 C9 C14 0.46(18) . . . . ?
N2 C9 C10 C11 -179.05(13) . . . . ?
C14 C9 C10 C11 1.4(2) . . . . ?
C9 C10 C11 C12 -0.2(2) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C2 N1 C14 C13 -179.06(12) . . . . ?
C2 N1 C14 C9 1.02(18) . . . . ?
C12 C13 C14 N1 -179.27(13) . . . . ?
C12 C13 C14 C9 0.6(2) . . . . ?
N2 C9 C14 N1 -1.2(2) . . . . ?
C10 C9 C14 N1 178.35(12) . . . . ?
N2 C9 C14 C13 178.87(12) . . . . ?
C10 C9 C14 C13 -1.6(2) . . . . ?
C1 N3 C15 C16 86.17(16) . . . . ?
C4 N3 C15 C16 -100.61(16) . . . . ?
N3 C15 C16 C17 72.37(17) . . . . ?
C15 C16 C17 C18 178.43(12) . . . . ?
C16 C17 C18 C23 119.26(16) . . . . ?
C16 C17 C18 C19 -60.8(2) . . . . ?
C23 C18 C19 C20 0.8(2) . . . . ?
C17 C18 C19 C20 -179.14(15) . . . . ?
C18 C19 C20 C21 0.5(3) . . . . ?
C19 C20 C21 C22 -0.9(2) . . . . ?
C20 C21 C22 C23 0.0(2) . . . . ?
C21 C22 C23 C18 1.4(2) . . . . ?
C19 C18 C23 C22 -1.7(2) . . . . ?
C17 C18 C23 C22 178.22(15) . . . . ?
C32 N5 C24 N6 178.11(12) . . . . ?
C32 N5 C24 C25 -0.78(18) . . . . ?
C27 N6 C24 N5 -179.06(12) . . . . ?
C38 N6 C24 N5 -4.7(2) . . . . ?
C27 N6 C24 C25 -0.02(14) . . . . ?
C38 N6 C24 C25 174.38(12) . . . . ?
C37 N4 C25 C24 0.34(18) . . . . ?
C37 N4 C25 C26 -178.19(13) . . . . ?
N5 C24 C25 N4 0.3(2) . . . . ?
N6 C24 C25 N4 -178.72(11) . . . . ?
N5 C24 C25 C26 179.18(12) . . . . ?
N6 C24 C25 C26 0.13(14) . . . . ?
N4 C25 C26 C31 0.5(3) . . . . ?
C24 C25 C26 C31 -178.16(14) . . . . ?
N4 C25 C26 C27 178.50(13) . . . . ?
C24 C25 C26 C27 -0.19(14) . . . . ?
C24 N6 C27 C28 179.37(13) . . . . ?
C38 N6 C27 C28 4.9(2) . . . . ?
C24 N6 C27 C26 -0.11(14) . . . . ?
C38 N6 C27 C26 -174.54(12) . . . . ?
C31 C26 C27 C28 -1.0(2) . . . . ?
C25 C26 C27 C28 -179.33(12) . . . . ?
C31 C26 C27 N6 178.53(11) . . . . ?
C25 C26 C27 N6 0.19(14) . . . . ?
N6 C27 C28 C29 -178.96(13) . . . . ?
C26 C27 C28 C29 0.5(2) . . . . ?
C27 C28 C29 C30 0.4(2) . . . . ?
C28 C29 C30 C31 -0.8(2) . . . . ?
C29 C30 C31 C26 0.2(2) . . . . ?
C27 C26 C31 C30 0.62(19) . . . . ?
C25 C26 C31 C30 178.39(14) . . . . ?
C24 N5 C32 C33 -177.83(12) . . . . ?
C24 N5 C32 C37 0.61(18) . . . . ?
N5 C32 C33 C34 179.45(13) . . . . ?
C37 C32 C33 C34 1.0(2) . . . . ?
C32 C33 C34 C35 -0.8(2) . . . . ?
C33 C34 C35 C36 0.4(2) . . . . ?
C34 C35 C36 C37 -0.2(2) . . . . ?
C25 N4 C37 C36 178.69(12) . . . . ?
C25 N4 C37 C32 -0.48(18) . . . . ?
C35 C36 C37 N4 -178.82(12) . . . . ?
C35 C36 C37 C32 0.4(2) . . . . ?
N5 C32 C37 N4 0.0(2) . . . . ?
C33 C32 C37 N4 178.43(12) . . . . ?
N5 C32 C37 C36 -179.16(12) . . . . ?
C33 C32 C37 C36 -0.74(19) . . . . ?
C24 N6 C38 C39A 104.82(16) . . . . ?
C27 N6 C38 C39A -81.70(17) . . . . ?
C24 N6 C38 C39B 69.4(5) . . . . ?
C27 N6 C38 C39B -117.1(5) . . . . ?
N6 C38 C39A C40A -64.88(18) . . . . ?
C39B C38 C39A C40A 28.2(10) . . . . ?
C38 C39A C40A C41A -175.76(13) . . . . ?
C39A C40A C41A C42A 76.7(2) . . . . ?
C39A C40A C41A C46A -102.3(2) . . . . ?
C46A C41A C42A C43A -1.0(3) . . . . ?
C40A C41A C42A C43A 179.93(19) . . . . ?
C41A C42A C43A C44A -0.5(3) . . . . ?
C42A C43A C44A C45A 1.5(3) . . . . ?
C43A C44A C45A C46A -0.9(3) . . . . ?
C44A C45A C46A C41A -0.6(3) . . . . ?
C42A C41A C46A C45A 1.6(3) . . . . ?
C40A C41A C46A C45A -179.4(2) . . . . ?
N6 C38 C39B C40B 78.6(11) . . . . ?
C39A C38 C39B C40B -21.8(7) . . . . ?
C38 C39B C40B C41B 172.4(10) . . . . ?
C39B C40B C41B C42B -55.8(17) . . . . ?
C39B C40B C41B C46B 125.6(15) . . . . ?
C46B C41B C42B C43B 0.0 . . . . ?
C40B C41B C42B C43B -178.6(17) . . . . ?
C41B C42B C43B C44B 0.0 . . . . ?
C42B C43B C44B C45B 0.0 . . . . ?
C43B C44B C45B C46B 0.0 . . . . ?
C44B C45B C46B C41B 0.0 . . . . ?
C42B C41B C46B C45B 0.0 . . . . ?
C40B C41B C46B C45B 178.6(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        29.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.045

#=====================  End of is_ht3h053 =================================

#=====================  End of CIF submission =================================

_database_code_depnum_ccdc_archive 'CCDC 997725'
