# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Guang-Xiang Liu'
_publ_contact_author_email       LIUGX@LIVE.COM

_publ_section_title              
;
A Series of Novel Ion-pair Complexes Based on TCNQ:
Syntheses, Crystal Structures and Properties
;
loop_
_publ_author_name
'Guang-Xiang Liu'
'Xiao-Ming Ren'
'Wei-Yin Sum'
'Heng Xu'

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

data_TQ1
_database_code_depnum_ccdc_archive 'CCDC 674961'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 Cl N, 1.5(C12 H4 N4)'
_chemical_formula_sum            'C30 H17 Cl N7'
_chemical_formula_weight         510.96

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'
Cl Cl 0.1484 0.1585 '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           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.666(2)
_cell_length_b                   11.987(3)
_cell_length_c                   13.808(4)
_cell_angle_alpha                82.236(4)
_cell_angle_beta                 88.974(4)
_cell_angle_gamma                86.329(4)
_cell_volume                     1254.6(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2129
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      26.94

_exptl_crystal_description       block
_exptl_crystal_colour            'dark green'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             526
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9531
_exptl_absorpt_correction_T_max  0.9779
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 Smart Aepex CCD area detector'
_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            6207
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4333
_reflns_number_gt                3135
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART, 1998.'
_computing_cell_refinement       'SAINT-PLUS, Ver. 6.0, 1997'
_computing_data_reduction        'SAINT-PLUS, Ver. 6.0, 1997'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP, Ver. 6.10, Bruker AXS Inc., 2000.'
_computing_publication_material  'SHELXTL-Bruker AXS Inc., 1998.'

_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)+(0.1281P)²+0.0000P] 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         4333
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.1942
_refine_ls_wR_factor_gt          0.1744
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0881(4) 0.65882(19) -0.01261(18) 0.0441(6) Uani 1 1 d . . .
C2 C 1.1676(4) 0.6314(2) -0.0979(2) 0.0505(7) Uani 1 1 d . . .
H2 H 1.2880 0.6339 -0.1062 0.061 Uiso 1 1 calc R . .
C3 C 1.0679(4) 0.6006(2) -0.1697(2) 0.0567(8) Uani 1 1 d . . .
H3 H 1.1204 0.5825 -0.2273 0.068 Uiso 1 1 calc R . .
C4 C 0.8904(4) 0.5962(2) -0.15713(19) 0.0549(7) Uani 1 1 d . . .
H4 H 0.8241 0.5742 -0.2062 0.066 Uiso 1 1 calc R . .
C5 C 0.8091(4) 0.6237(2) -0.0738(2) 0.0507(7) Uani 1 1 d . . .
H5 H 0.6886 0.6204 -0.0666 0.061 Uiso 1 1 calc R . .
C6 C 0.9084(3) 0.65727(19) 0.00164(17) 0.0413(6) Uani 1 1 d . . .
C7 C 0.8194(4) 0.6905(2) 0.09214(19) 0.0528(7) Uani 1 1 d . . .
H7A H 0.7007 0.6664 0.0956 0.063 Uiso 1 1 calc R . .
H7B H 0.8810 0.6531 0.1495 0.063 Uiso 1 1 calc R . .
C8 C 0.7443(3) 0.8844(2) 0.01519(19) 0.0532(7) Uani 1 1 d . . .
H8 H 0.6982 0.8539 -0.0365 0.064 Uiso 1 1 calc R . .
C9 C 0.7390(4) 0.9984(2) 0.0134(2) 0.0592(8) Uani 1 1 d . . .
H9 H 0.6913 1.0460 -0.0396 0.071 Uiso 1 1 calc R . .
C10 C 0.8050(4) 1.0425(2) 0.0913(2) 0.0570(8) Uani 1 1 d . . .
H10 H 0.8028 1.1202 0.0909 0.068 Uiso 1 1 calc R . .
C11 C 0.8735(4) 0.9722(2) 0.1687(2) 0.0567(7) Uani 1 1 d . . .
H11 H 0.9168 1.0012 0.2220 0.068 Uiso 1 1 calc R . .
C12 C 0.8780(4) 0.8581(2) 0.16706(18) 0.0526(7) Uani 1 1 d . . .
H12 H 0.9250 0.8096 0.2197 0.063 Uiso 1 1 calc R . .
C13 C 0.4291(3) 0.1910(2) 0.25867(19) 0.0456(6) Uani 1 1 d . . .
C14 C 0.1624(3) 0.1876(2) 0.35037(17) 0.0456(6) Uani 1 1 d . . .
C15 C 0.3395(3) 0.2148(2) 0.34531(16) 0.0395(6) Uani 1 1 d . . .
C16 C 0.4199(3) 0.26609(19) 0.41654(16) 0.0362(5) Uani 1 1 d . . .
C17 C 0.5993(3) 0.29058(19) 0.41000(16) 0.0368(6) Uani 1 1 d . . .
H17 H 0.6656 0.2725 0.3566 0.044 Uiso 1 1 calc R . .
C18 C 0.6757(3) 0.3398(2) 0.47997(16) 0.0376(6) Uani 1 1 d . . .
H18 H 0.7933 0.3546 0.4737 0.045 Uiso 1 1 calc R . .
C19 C 0.5791(3) 0.36923(19) 0.56258(16) 0.0365(5) Uani 1 1 d . . .
C20 C 0.3987(3) 0.3460(2) 0.56869(17) 0.0407(6) Uani 1 1 d . . .
H20 H 0.3323 0.3659 0.6214 0.049 Uiso 1 1 calc R . .
C21 C 0.3211(3) 0.2955(2) 0.49956(17) 0.0399(6) Uani 1 1 d . . .
H21 H 0.2038 0.2802 0.5062 0.048 Uiso 1 1 calc R . .
C22 C 0.6553(3) 0.4209(2) 0.63521(17) 0.0413(6) Uani 1 1 d . . .
C23 C 0.8374(4) 0.4399(3) 0.6347(2) 0.0577(8) Uani 1 1 d . . .
C24 C 0.5559(3) 0.4560(2) 0.71500(18) 0.0454(6) Uani 1 1 d . . .
C25 C 0.8509(3) 0.1333(2) 0.62442(16) 0.0396(6) Uani 1 1 d . . .
C26 C 0.5938(3) 0.1351(2) 0.72517(17) 0.0399(6) Uani 1 1 d . . .
C27 C 0.6731(3) 0.10744(18) 0.63770(15) 0.0329(5) Uani 1 1 d . . .
C28 C 0.5875(3) 0.05275(17) 0.56941(15) 0.0303(5) Uani 1 1 d . . .
C29 C 0.6746(3) 0.02323(18) 0.48440(15) 0.0316(5) Uani 1 1 d . . .
H29 H 0.7911 0.0391 0.4739 0.038 Uiso 1 1 calc R . .
C30 C 0.4081(3) 0.02780(18) 0.58232(16) 0.0319(5) Uani 1 1 d . . .
H30 H 0.3471 0.0468 0.6372 0.038 Uiso 1 1 calc R . .
Cl1 Cl 1.21862(10) 0.69733(6) 0.07759(5) 0.0646(3) Uani 1 1 d . . .
N1 N 0.8160(3) 0.81544(17) 0.09136(14) 0.0435(5) Uani 1 1 d . . .
N2 N 0.4940(3) 0.1729(2) 0.18676(18) 0.0655(7) Uani 1 1 d . . .
N3 N 0.0194(3) 0.1643(2) 0.35071(19) 0.0700(7) Uani 1 1 d . . .
N4 N 0.9814(4) 0.4542(3) 0.6384(2) 0.0990(12) Uani 1 1 d . . .
N5 N 0.4796(3) 0.4858(2) 0.77945(18) 0.0628(7) Uani 1 1 d . . .
N6 N 0.9944(3) 0.1551(2) 0.61541(16) 0.0581(6) Uani 1 1 d . . .
N7 N 0.5321(3) 0.1592(2) 0.79679(15) 0.0587(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
C1 C2 1.386(4) . ?
C1 C6 1.389(4) . ?
C1 Cl1 1.739(3) . ?
C2 C3 1.366(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.417(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.502(3) . ?
C7 N1 1.495(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.349(3) . ?
C8 C9 1.362(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.359(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(4) . ?
C11 H11 0.9300 . ?
C12 N1 1.331(3) . ?
C12 H12 0.9300 . ?
C13 N2 1.143(3) . ?
C13 C15 1.422(3) . ?
C14 N3 1.148(3) . ?
C14 C15 1.415(3) . ?
C15 C16 1.400(3) . ?
C16 C17 1.423(3) . ?
C16 C21 1.434(3) . ?
C17 C18 1.358(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.421(3) . ?
C18 H18 0.9300 . ?
C19 C22 1.402(3) . ?
C19 C20 1.427(3) . ?
C20 C21 1.362(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C24 1.423(3) . ?
C22 C23 1.429(4) . ?
C23 N4 1.131(4) . ?
C24 N5 1.142(3) . ?
C25 N6 1.148(3) . ?
C25 C27 1.421(3) . ?
C26 N7 1.153(3) . ?
C26 C27 1.412(3) . ?
C27 C28 1.412(3) . ?
C28 C29 1.415(3) . ?
C28 C30 1.429(3) . ?
C29 C30 1.359(3) 2_656 ?
C29 H29 0.9300 . ?
C30 C29 1.359(3) 2_656 ?
C30 H30 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.7(2) . . ?
C2 C1 Cl1 118.5(2) . . ?
C6 C1 Cl1 119.8(2) . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 117.3(2) . . ?
C1 C6 C7 122.4(2) . . ?
C5 C6 C7 120.2(2) . . ?
N1 C7 C6 110.51(19) . . ?
N1 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
N1 C8 C9 120.5(3) . . ?
N1 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 119.1(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.1(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
N1 C12 C11 121.1(2) . . ?
N1 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
N2 C13 C15 176.8(3) . . ?
N3 C14 C15 177.2(3) . . ?
C16 C15 C14 123.6(2) . . ?
C16 C15 C13 121.9(2) . . ?
C14 C15 C13 114.5(2) . . ?
C15 C16 C17 122.2(2) . . ?
C15 C16 C21 120.0(2) . . ?
C17 C16 C21 117.9(2) . . ?
C18 C17 C16 121.5(2) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 121.1(2) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C22 C19 C18 122.0(2) . . ?
C22 C19 C20 120.5(2) . . ?
C18 C19 C20 117.5(2) . . ?
C21 C20 C19 121.9(2) . . ?
C21 C20 H20 119.0 . . ?
C19 C20 H20 119.0 . . ?
C20 C21 C16 120.1(2) . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
C19 C22 C24 121.9(2) . . ?
C19 C22 C23 122.3(2) . . ?
C24 C22 C23 115.9(2) . . ?
N4 C23 C22 177.2(3) . . ?
N5 C24 C22 178.3(3) . . ?
N6 C25 C27 178.6(2) . . ?
N7 C26 C27 178.4(2) . . ?
C28 C27 C26 123.5(2) . . ?
C28 C27 C25 121.19(19) . . ?
C26 C27 C25 115.27(19) . . ?
C27 C28 C29 121.36(19) . . ?
C27 C28 C30 121.1(2) . . ?
C29 C28 C30 117.47(19) . . ?
C30 C29 C28 121.5(2) 2_656 . ?
C30 C29 H29 119.2 2_656 . ?
C28 C29 H29 119.2 . . ?
C29 C30 C28 121.0(2) 2_656 . ?
C29 C30 H30 119.5 2_656 . ?
C28 C30 H30 119.5 . . ?
C12 N1 C8 120.3(2) . . ?
C12 N1 C7 120.1(2) . . ?
C8 N1 C7 119.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.8(4) . . . . ?
Cl1 C1 C2 C3 179.84(19) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C2 C1 C6 C5 1.5(4) . . . . ?
Cl1 C1 C6 C5 -179.17(17) . . . . ?
C2 C1 C6 C7 -177.9(2) . . . . ?
Cl1 C1 C6 C7 1.5(3) . . . . ?
C4 C5 C6 C1 -1.0(4) . . . . ?
C4 C5 C6 C7 178.4(2) . . . . ?
C1 C6 C7 N1 73.1(3) . . . . ?
C5 C6 C7 N1 -106.2(3) . . . . ?
N1 C8 C9 C10 -1.1(4) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
C10 C11 C12 N1 -0.2(4) . . . . ?
N3 C14 C15 C16 174(6) . . . . ?
N3 C14 C15 C13 -3(6) . . . . ?
N2 C13 C15 C16 -145(5) . . . . ?
N2 C13 C15 C14 32(5) . . . . ?
C14 C15 C16 C17 178.9(2) . . . . ?
C13 C15 C16 C17 -4.3(3) . . . . ?
C14 C15 C16 C21 -1.0(3) . . . . ?
C13 C15 C16 C21 175.8(2) . . . . ?
C15 C16 C17 C18 -179.7(2) . . . . ?
C21 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C22 -179.5(2) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C22 C19 C20 C21 -179.7(2) . . . . ?
C18 C19 C20 C21 1.3(3) . . . . ?
C19 C20 C21 C16 -1.2(4) . . . . ?
C15 C16 C21 C20 -179.6(2) . . . . ?
C17 C16 C21 C20 0.4(3) . . . . ?
C18 C19 C22 C24 176.4(2) . . . . ?
C20 C19 C22 C24 -2.5(4) . . . . ?
C18 C19 C22 C23 -4.6(4) . . . . ?
C20 C19 C22 C23 176.4(2) . . . . ?
C19 C22 C23 N4 -145(7) . . . . ?
C24 C22 C23 N4 34(7) . . . . ?
C19 C22 C24 N5 -163(10) . . . . ?
C23 C22 C24 N5 18(10) . . . . ?
N7 C26 C27 C28 -164(10) . . . . ?
N7 C26 C27 C25 19(11) . . . . ?
N6 C25 C27 C28 -179(100) . . . . ?
N6 C25 C27 C26 -2(12) . . . . ?
C26 C27 C28 C29 -177.7(2) . . . . ?
C25 C27 C28 C29 -1.0(3) . . . . ?
C26 C27 C28 C30 4.0(3) . . . . ?
C25 C27 C28 C30 -179.4(2) . . . . ?
C27 C28 C29 C30 -178.9(2) . . . 2_656 ?
C30 C28 C29 C30 -0.5(3) . . . 2_656 ?
C27 C28 C30 C29 178.9(2) . . . 2_656 ?
C29 C28 C30 C29 0.5(3) . . . 2_656 ?
C11 C12 N1 C8 -1.2(4) . . . . ?
C11 C12 N1 C7 -178.9(2) . . . . ?
C9 C8 N1 C12 1.9(4) . . . . ?
C9 C8 N1 C7 179.6(2) . . . . ?
C6 C7 N1 C12 -126.5(3) . . . . ?
C6 C7 N1 C8 55.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         1.012
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.075

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

data_TQ2
_database_code_depnum_ccdc_archive 'CCDC 674962'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H13 Cl N, C12 H4 N4'
_chemical_formula_sum            'C25 H17 Cl N5'
_chemical_formula_weight         422.89

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'
Cl Cl 0.1484 0.1585 '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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   4.1599(15)
_cell_length_b                   25.278(9)
_cell_length_c                   19.840(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.912(5)
_cell_angle_gamma                90.00
_cell_volume                     2086.1(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1573
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      21.08

_exptl_crystal_description       needle
_exptl_crystal_colour            'dark green'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             876
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9295
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 Smart Aepex CCD area detector'
_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            10494
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.30
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3826
_reflns_number_gt                2251
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART, 1998.'
_computing_cell_refinement       'SAINT-PLUS, Ver. 6.0, 1997'
_computing_data_reduction        'SAINT-PLUS, Ver. 6.0, 1997'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP, Ver. 6.10, Bruker AXS Inc., 2000.'
_computing_publication_material  'SHELXTL-Bruker AXS Inc., 1998.'

_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)+(0.0416P)²+0.0000P] 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         3826
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3392(6) 0.42181(9) -0.07090(11) 0.0500(6) Uani 1 1 d . . .
C2 C 0.4338(6) 0.42226(9) -0.00352(11) 0.0534(7) Uani 1 1 d . . .
H2 H 0.3730 0.4498 0.0246 0.064 Uiso 1 1 calc R . .
C3 C 0.6192(6) 0.38124(9) 0.02101(11) 0.0499(6) Uani 1 1 d . . .
H3 H 0.6852 0.3815 0.0660 0.060 Uiso 1 1 calc R . .
C4 C 0.7096(6) 0.33956(9) -0.01972(10) 0.0441(6) Uani 1 1 d . . .
C5 C 0.6076(6) 0.34000(10) -0.08712(11) 0.0529(6) Uani 1 1 d . . .
H5 H 0.6643 0.3122 -0.1153 0.064 Uiso 1 1 calc R . .
C6 C 0.4247(6) 0.38088(10) -0.11244(11) 0.0566(7) Uani 1 1 d . . .
H6 H 0.3592 0.3808 -0.1575 0.068 Uiso 1 1 calc R . .
C7 C 0.9250(6) 0.29597(9) 0.00689(11) 0.0516(6) Uani 1 1 d . . .
H7A H 1.0399 0.2803 -0.0303 0.062 Uiso 1 1 calc R . .
H7B H 1.0826 0.3110 0.0380 0.062 Uiso 1 1 calc R . .
C8 C 0.6207(6) 0.21251(9) 0.00701(11) 0.0513(6) Uani 1 1 d . . .
H8 H 0.6511 0.2106 -0.0393 0.062 Uiso 1 1 calc R . .
C9 C 0.4551(6) 0.17339(9) 0.03928(12) 0.0570(7) Uani 1 1 d . . .
H9 H 0.3727 0.1448 0.0151 0.068 Uiso 1 1 calc R . .
C10 C 0.4111(6) 0.17666(9) 0.10796(12) 0.0567(7) Uani 1 1 d . . .
H10 H 0.2986 0.1501 0.1299 0.068 Uiso 1 1 calc R . .
C11 C 0.5327(6) 0.21906(9) 0.14460(11) 0.0479(6) Uani 1 1 d . . .
C12 C 0.6961(6) 0.25730(8) 0.10968(10) 0.0453(6) Uani 1 1 d . . .
H12 H 0.7789 0.2863 0.1329 0.054 Uiso 1 1 calc R . .
C13 C 0.4934(7) 0.22400(10) 0.21998(11) 0.0708(8) Uani 1 1 d . . .
H13A H 0.5602 0.2586 0.2343 0.106 Uiso 1 1 calc R . .
H13B H 0.6232 0.1978 0.2424 0.106 Uiso 1 1 calc R . .
H13C H 0.2718 0.2187 0.2310 0.106 Uiso 1 1 calc R . .
C14 C 1.1122(6) 0.35695(8) 0.22138(11) 0.0428(6) Uani 1 1 d . . .
C15 C 1.0847(6) 0.32661(9) 0.33625(11) 0.0498(6) Uani 1 1 d . . .
C16 C 0.9983(6) 0.36554(8) 0.28763(9) 0.0417(6) Uani 1 1 d . . .
C17 C 0.8027(5) 0.40974(8) 0.30349(9) 0.0413(6) Uani 1 1 d . . .
C18 C 0.6995(6) 0.41963(8) 0.37029(10) 0.0459(6) Uani 1 1 d . . .
H18 H 0.7599 0.3963 0.4045 0.055 Uiso 1 1 calc R . .
C19 C 0.5153(6) 0.46210(8) 0.38540(10) 0.0493(6) Uani 1 1 d . . .
H19 H 0.4545 0.4675 0.4298 0.059 Uiso 1 1 calc R . .
C20 C 0.4133(6) 0.49844(8) 0.33502(10) 0.0431(6) Uani 1 1 d . . .
C21 C 0.5177(6) 0.48891(8) 0.26838(10) 0.0474(6) Uani 1 1 d . . .
H21 H 0.4582 0.5123 0.2343 0.057 Uiso 1 1 calc R . .
C22 C 0.7031(6) 0.44628(8) 0.25322(10) 0.0462(6) Uani 1 1 d . . .
H22 H 0.7655 0.4410 0.2089 0.055 Uiso 1 1 calc R . .
C23 C 0.2198(6) 0.54304(8) 0.34990(10) 0.0457(6) Uani 1 1 d . . .
C24 C 0.1092(6) 0.55493(9) 0.41603(12) 0.0497(6) Uani 1 1 d . . .
C25 C 0.1216(6) 0.58022(9) 0.30003(11) 0.0477(6) Uani 1 1 d . . .
Cl1 Cl 0.11744(18) 0.47479(3) -0.10296(3) 0.0714(2) Uani 1 1 d . . .
N1 N 0.7395(4) 0.25369(7) 0.04227(8) 0.0426(5) Uani 1 1 d . . .
N2 N 1.2023(5) 0.34973(8) 0.16765(9) 0.0600(6) Uani 1 1 d . . .
N3 N 1.1478(6) 0.29459(9) 0.37559(10) 0.0709(7) Uani 1 1 d . . .
N4 N 0.0168(6) 0.56699(8) 0.46782(10) 0.0680(7) Uani 1 1 d . . .
N5 N 0.0435(6) 0.61151(8) 0.26123(10) 0.0660(6) Uani 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.373(3) . ?
C1 C2 1.388(3) . ?
C1 Cl1 1.741(2) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(3) . ?
C4 C7 1.510(3) . ?
C5 C6 1.373(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.499(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.344(3) . ?
C8 C9 1.370(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(3) . ?
C11 C13 1.512(3) . ?
C12 N1 1.355(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N2 1.150(3) . ?
C14 C16 1.421(3) . ?
C15 N3 1.152(3) . ?
C15 C16 1.420(3) . ?
C16 C17 1.420(3) . ?
C17 C22 1.417(3) . ?
C17 C18 1.422(3) . ?
C18 C19 1.356(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.417(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.419(3) . ?
C20 C23 1.419(3) . ?
C21 C22 1.361(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C25 1.420(3) . ?
C23 C24 1.429(3) . ?
C24 N4 1.144(3) . ?
C25 N5 1.147(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
C6 C1 C2 120.8(2) . . ?
C6 C1 Cl1 120.07(18) . . ?
C2 C1 Cl1 119.10(19) . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 121.5(2) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 118.2(2) . . ?
C3 C4 C7 121.11(19) . . ?
C5 C4 C7 120.7(2) . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 119.6(2) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
N1 C7 C4 112.13(18) . . ?
N1 C7 H7A 109.2 . . ?
C4 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C4 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 C9 119.9(2) . . ?
N1 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 119.6(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 120.7(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 117.3(2) . . ?
C12 C11 C13 120.2(2) . . ?
C10 C11 C13 122.6(2) . . ?
N1 C12 C11 121.6(2) . . ?
N1 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C16 179.4(3) . . ?
N3 C15 C16 178.5(3) . . ?
C15 C16 C17 122.30(19) . . ?
C15 C16 C14 115.97(19) . . ?
C17 C16 C14 121.72(18) . . ?
C22 C17 C16 121.28(18) . . ?
C22 C17 C18 116.89(19) . . ?
C16 C17 C18 121.83(18) . . ?
C19 C18 C17 121.71(19) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C20 121.4(2) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C21 117.0(2) . . ?
C19 C20 C23 122.17(19) . . ?
C21 C20 C23 120.79(19) . . ?
C22 C21 C20 121.54(19) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C17 121.40(19) . . ?
C21 C22 H22 119.3 . . ?
C17 C22 H22 119.3 . . ?
C20 C23 C25 122.60(19) . . ?
C20 C23 C24 123.38(19) . . ?
C25 C23 C24 114.0(2) . . ?
N4 C24 C23 176.5(2) . . ?
N5 C25 C23 177.8(2) . . ?
C8 N1 C12 120.82(19) . . ?
C8 N1 C7 119.74(18) . . ?
C12 N1 C7 119.44(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.9(4) . . . . ?
Cl1 C1 C2 C3 -177.63(18) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 C7 177.3(2) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C7 C4 C5 C6 -176.8(2) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
Cl1 C1 C6 C5 178.14(18) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C3 C4 C7 N1 84.8(3) . . . . ?
C5 C4 C7 N1 -98.0(2) . . . . ?
N1 C8 C9 C10 0.1(4) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C9 C10 C11 C13 -179.3(2) . . . . ?
C10 C11 C12 N1 -0.5(3) . . . . ?
C13 C11 C12 N1 179.1(2) . . . . ?
N3 C15 C16 C17 74(9) . . . . ?
N3 C15 C16 C14 -104(9) . . . . ?
N2 C14 C16 C15 84(30) . . . . ?
N2 C14 C16 C17 -94(30) . . . . ?
C15 C16 C17 C22 -176.0(2) . . . . ?
C14 C16 C17 C22 2.3(3) . . . . ?
C15 C16 C17 C18 4.4(4) . . . . ?
C14 C16 C17 C18 -177.3(2) . . . . ?
C22 C17 C18 C19 -0.2(3) . . . . ?
C16 C17 C18 C19 179.4(2) . . . . ?
C17 C18 C19 C20 0.8(4) . . . . ?
C18 C19 C20 C21 -1.2(3) . . . . ?
C18 C19 C20 C23 179.9(2) . . . . ?
C19 C20 C21 C22 1.1(4) . . . . ?
C23 C20 C21 C22 -179.9(2) . . . . ?
C20 C21 C22 C17 -0.6(4) . . . . ?
C16 C17 C22 C21 -179.5(2) . . . . ?
C18 C17 C22 C21 0.2(3) . . . . ?
C19 C20 C23 C25 178.8(2) . . . . ?
C21 C20 C23 C25 -0.2(4) . . . . ?
C19 C20 C23 C24 -0.6(4) . . . . ?
C21 C20 C23 C24 -179.6(2) . . . . ?
C20 C23 C24 N4 165(5) . . . . ?
C25 C23 C24 N4 -15(5) . . . . ?
C20 C23 C25 N5 -143(7) . . . . ?
C24 C23 C25 N5 37(7) . . . . ?
C9 C8 N1 C12 -0.3(3) . . . . ?
C9 C8 N1 C7 179.1(2) . . . . ?
C11 C12 N1 C8 0.6(3) . . . . ?
C11 C12 N1 C7 -178.8(2) . . . . ?
C4 C7 N1 C8 88.9(2) . . . . ?
C4 C7 N1 C12 -91.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.041

# Attachment 'CEC0801-revised.cif'

data_TQ3
_database_code_depnum_ccdc_archive 'CCDC 674963'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 N2, C12 H4 N4'
_chemical_formula_sum            'C24 H17 N6'
_chemical_formula_weight         389.44

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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.702(4)
_cell_length_b                   8.678(3)
_cell_length_c                   22.271(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.082(15)
_cell_angle_gamma                90.00
_cell_volume                     2080.6(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4476
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.68

_exptl_crystal_description       block
_exptl_crystal_colour            'dark green'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             812
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9816
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 Smart Aepex CCD area detector'
_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            9945
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_sigmaI/netI    0.1190
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3660
_reflns_number_gt                2814
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART, 1998'
_computing_cell_refinement       'SAINT-PLUS, Ver. 6.0, 1997'
_computing_data_reduction        'SAINT-PLUS, Ver. 6.0, 1997'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP, Ver. 6.10, Bruker AXS Inc., 2000'
_computing_publication_material  'SHELXTL-Bruker AXS Inc., 1998'

_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)+(0.0803P)²+0.0000P] 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         3660
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1705
_refine_ls_wR_factor_gt          0.1597
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.18011(11) 1.12991(15) 0.74730(6) 0.1078(9) Uani 1 1 d . . .
H1 H 0.2430 1.1863 0.7786 0.129 Uiso 1 1 calc R . .
C2 C 0.05749(11) 1.18297(15) 0.72425(6) 0.169(2) Uani 1 1 d R . .
H2 H 0.0385 1.2757 0.7392 0.203 Uiso 1 1 d R . .
C3 C -0.03352(11) 1.09681(15) 0.67970(6) 0.191(2) Uani 1 1 d R . .
H3 H -0.1156 1.1295 0.6656 0.229 Uiso 1 1 d R . .
C4 C -0.00843(11) 0.96999(15) 0.65642(6) 0.1603(18) Uani 1 1 d R . .
H4 H -0.0721 0.9153 0.6248 0.192 Uiso 1 1 d R . .
C5 C 0.11208(11) 0.91558(15) 0.67813(6) 0.1081(9) Uani 1 1 d R . .
H5 H 0.1290 0.8239 0.6616 0.130 Uiso 1 1 d R . .
C6 C 0.20727(11) 0.99730(15) 0.72431(6) 0.0644(5) Uani 1 1 d R . .
C7 C 0.33818(16) 0.9378(2) 0.74784(10) 0.0660(5) Uani 1 1 d . . .
H7A H 0.3550 0.9028 0.7107 0.079 Uiso 1 1 calc R . .
H7B H 0.3954 1.0210 0.7687 0.079 Uiso 1 1 calc R . .
C8 C 0.38156(16) 0.6646(2) 0.77971(8) 0.0560(4) Uani 1 1 d . . .
H8 H 0.3860 0.6470 0.7395 0.067 Uiso 1 1 calc R . .
C9 C 0.39724(16) 0.5452(2) 0.82065(8) 0.0558(4) Uani 1 1 d . . .
H9 H 0.4134 0.4476 0.8087 0.067 Uiso 1 1 calc R . .
C10 C 0.38932(13) 0.56699(19) 0.88140(7) 0.0496(4) Uani 1 1 d . . .
C11 C 0.37119(16) 0.7203(2) 0.89698(8) 0.0580(5) Uani 1 1 d . . .
H11 H 0.3687 0.7423 0.9373 0.070 Uiso 1 1 calc R . .
C12 C 0.35744(17) 0.8352(2) 0.85387(8) 0.0581(5) Uani 1 1 d . . .
H12 H 0.3461 0.9355 0.8653 0.070 Uiso 1 1 calc R . .
C13 C 0.33573(14) 1.04385(19) 0.99107(8) 0.0483(4) Uani 1 1 d . . .
C14 C 0.37712(14) 0.87013(18) 1.08221(8) 0.0506(4) Uani 1 1 d . . .
C15 C 0.29072(14) 0.93665(17) 1.02383(7) 0.0456(4) Uani 1 1 d . . .
C16 C 0.16381(13) 0.88763(17) 0.99686(7) 0.0432(4) Uani 1 1 d . . .
C17 C 0.12121(13) 0.76769(18) 1.02515(7) 0.0477(4) Uani 1 1 d . . .
H17 H 0.1771 0.7181 1.0620 0.057 Uiso 1 1 calc R . .
C18 C 0.00000(14) 0.72219(17) 0.99996(8) 0.0488(4) Uani 1 1 d . . .
H18 H -0.0253 0.6428 1.0200 0.059 Uiso 1 1 calc R . .
C19 C -0.08839(13) 0.79410(17) 0.94352(7) 0.0436(4) Uani 1 1 d . . .
C20 C -0.04504(14) 0.91169(19) 0.91419(7) 0.0505(4) Uani 1 1 d . . .
H20 H -0.1004 0.9593 0.8766 0.061 Uiso 1 1 calc R . .
C21 C 0.07663(14) 0.95743(18) 0.93967(7) 0.0495(4) Uani 1 1 d . . .
H21 H 0.1025 1.0354 0.9192 0.059 Uiso 1 1 calc R . .
C22 C -0.21540(14) 0.74820(19) 0.91734(7) 0.0475(4) Uani 1 1 d . . .
C23 C -0.25995(14) 0.63389(19) 0.94732(8) 0.0505(4) Uani 1 1 d . . .
C24 C -0.30110(15) 0.80849(19) 0.85767(8) 0.0529(4) Uani 1 1 d . . .
N1 N 0.35970(12) 0.80861(16) 0.79487(7) 0.0517(4) Uani 1 1 d . . .
N2 N 0.39642(14) 0.45085(17) 0.92135(8) 0.0678(5) Uani 1 1 d . . .
H2A H 0.4062 0.3583 0.9104 0.081 Uiso 1 1 calc R . .
H2B H 0.3912 0.4680 0.9582 0.081 Uiso 1 1 calc R . .
N3 N 0.36892(15) 1.12874(19) 0.96161(8) 0.0671(5) Uani 1 1 d . . .
N4 N 0.44544(14) 0.81610(18) 1.13006(8) 0.0689(5) Uani 1 1 d . . .
N5 N -0.29552(15) 0.54040(18) 0.97272(9) 0.0707(5) Uani 1 1 d . . .
N6 N -0.36923(15) 0.8566(2) 0.80864(8) 0.0707(5) Uani 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3473 . ?
C1 C2 1.3989 . ?
C1 H1 0.9300 . ?
C2 C3 1.3598 . ?
C2 H2 0.9300 . ?
C3 C4 1.2983 . ?
C3 H3 0.9300 . ?
C4 C5 1.3824 . ?
C4 H4 0.9300 . ?
C5 C6 1.3795 . ?
C5 H5 0.9300 . ?
C6 C7 1.503(2) . ?
C7 N1 1.487(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.344(2) . ?
C8 N1 1.345(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.405(3) . ?
C9 H9 0.9300 . ?
C10 N2 1.325(2) . ?
C10 C11 1.412(2) . ?
C11 C12 1.349(2) . ?
C11 H11 0.9300 . ?
C12 N1 1.345(2) . ?
C12 H12 0.9300 . ?
C13 N3 1.151(2) . ?
C13 C15 1.406(2) . ?
C14 N4 1.1519(19) . ?
C14 C15 1.420(2) . ?
C15 C16 1.431(2) . ?
C16 C17 1.405(2) . ?
C16 C21 1.418(2) . ?
C17 C18 1.363(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.421(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.409(2) . ?
C19 C22 1.424(2) . ?
C20 C21 1.369(2) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.405(2) . ?
C22 C24 1.414(2) . ?
C23 N5 1.156(2) . ?
C24 N6 1.149(2) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.2 . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 118.9 . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 121.5 . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.6 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C6 C5 118.7 . . ?
C1 C6 C7 121.40(10) . . ?
C5 C6 C7 119.87(10) . . ?
N1 C7 C6 111.88(14) . . ?
N1 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 N1 122.31(15) . . ?
C9 C8 H8 118.8 . . ?
N1 C8 H8 118.8 . . ?
C8 C9 C10 120.45(16) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
N2 C10 C9 122.28(16) . . ?
N2 C10 C11 121.85(15) . . ?
C9 C10 C11 115.87(16) . . ?
C12 C11 C10 120.61(16) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
N1 C12 C11 121.71(16) . . ?
N1 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
N3 C13 C15 176.88(16) . . ?
N4 C14 C15 178.65(18) . . ?
C13 C15 C14 117.85(14) . . ?
C13 C15 C16 121.14(13) . . ?
C14 C15 C16 120.86(14) . . ?
C17 C16 C21 117.53(13) . . ?
C17 C16 C15 121.61(13) . . ?
C21 C16 C15 120.85(14) . . ?
C18 C17 C16 121.65(14) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 121.05(15) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 117.30(14) . . ?
C20 C19 C22 121.36(13) . . ?
C18 C19 C22 121.34(15) . . ?
C21 C20 C19 121.53(13) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C16 120.91(15) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
C23 C22 C24 116.69(14) . . ?
C23 C22 C19 121.67(14) . . ?
C24 C22 C19 121.53(15) . . ?
N5 C23 C22 179.16(18) . . ?
N6 C24 C22 178.71(19) . . ?
C12 N1 C8 118.93(15) . . ?
C12 N1 C7 119.74(15) . . ?
C8 N1 C7 121.34(15) . . ?
C10 N2 H2A 120.0 . . ?
C10 N2 H2B 120.0 . . ?
H2A N2 H2B 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
C6 C1 C2 C3 1.6 . . . . ?
C1 C2 C3 C4 -2.6 . . . . ?
C2 C3 C4 C5 2.3 . . . . ?
C3 C4 C5 C6 -0.9 . . . . ?
C2 C1 C6 C5 -0.3 . . . . ?
C2 C1 C6 C7 179.65(10) . . . . ?
C4 C5 C6 C1 -0.1 . . . . ?
C4 C5 C6 C7 179.98(10) . . . . ?
C1 C6 C7 N1 103.30(13) . . . . ?
C5 C6 C7 N1 -76.79(15) . . . . ?
N1 C8 C9 C10 1.0(3) . . . . ?
C8 C9 C10 N2 175.66(15) . . . . ?
C8 C9 C10 C11 -3.3(2) . . . . ?
N2 C10 C11 C12 -176.31(16) . . . . ?
C9 C10 C11 C12 2.7(2) . . . . ?
C10 C11 C12 N1 0.4(3) . . . . ?
N3 C13 C15 C14 142(3) . . . . ?
N3 C13 C15 C16 -34(3) . . . . ?
N4 C14 C15 C13 145(7) . . . . ?
N4 C14 C15 C16 -39(8) . . . . ?
C13 C15 C16 C17 172.44(14) . . . . ?
C14 C15 C16 C17 -3.0(2) . . . . ?
C13 C15 C16 C21 -6.6(2) . . . . ?
C14 C15 C16 C21 178.02(14) . . . . ?
C21 C16 C17 C18 -1.8(2) . . . . ?
C15 C16 C17 C18 179.17(15) . . . . ?
C16 C17 C18 C19 0.4(2) . . . . ?
C17 C18 C19 C20 1.2(2) . . . . ?
C17 C18 C19 C22 -179.35(14) . . . . ?
C18 C19 C20 C21 -1.4(2) . . . . ?
C22 C19 C20 C21 179.18(16) . . . . ?
C19 C20 C21 C16 0.0(3) . . . . ?
C17 C16 C21 C20 1.6(2) . . . . ?
C15 C16 C21 C20 -179.35(15) . . . . ?
C20 C19 C22 C23 -178.27(14) . . . . ?
C18 C19 C22 C23 2.3(2) . . . . ?
C20 C19 C22 C24 5.8(2) . . . . ?
C18 C19 C22 C24 -173.63(15) . . . . ?
C24 C22 C23 N5 -153(13) . . . . ?
C19 C22 C23 N5 31(13) . . . . ?
C23 C22 C24 N6 -122(9) . . . . ?
C19 C22 C24 N6 54(9) . . . . ?
C11 C12 N1 C8 -2.9(3) . . . . ?
C11 C12 N1 C7 177.11(16) . . . . ?
C9 C8 N1 C12 2.2(3) . . . . ?
C9 C8 N1 C7 -177.78(15) . . . . ?
C6 C7 N1 C12 -67.3(2) . . . . ?
C6 C7 N1 C8 112.72(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.057

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

data_TQ4
_database_code_depnum_ccdc_archive 'CCDC 674964'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C16 H13 Br N), 2(C12 H4 N4), C2 H3 N'
_chemical_formula_sum            'C58 H37 Br2 N11'
_chemical_formula_weight         1047.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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                   35.313(18)
_cell_length_b                   7.272(4)
_cell_length_c                   22.982(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 124.01(3)
_cell_angle_gamma                90.00
_cell_volume                     4892(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      17.95

_exptl_crystal_description       platelet
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2128
_exptl_absorpt_coefficient_mu    1.709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7262
_exptl_absorpt_correction_T_max  0.9348
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 Smart Aepex CCD area detector'
_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            11529
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0995
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4256
_reflns_number_gt                2525
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART, 1998'
_computing_cell_refinement       'SAINT-PLUS, Ver. 6.0, 1997'
_computing_data_reduction        'SAINT-PLUS, Ver. 6.0, 1997'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP, Ver. 6.10, Bruker AXS Inc., 2000'
_computing_publication_material  'SHELXTL-Bruker AXS Inc., 1998'

_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)+(0.0107P)²+0.0000P] 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         4256
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1968
_refine_ls_R_factor_gt           0.0804
_refine_ls_wR_factor_ref         0.1373
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
Br1 Br 0.21837(3) 0.83030(12) 0.21516(5) 0.1003(4) Uani 1 1 d . . .
C1 C 0.1841(2) 0.6091(9) 0.1923(4) 0.058(2) Uani 1 1 d . . .
C2 C 0.1690(2) 0.5533(11) 0.2325(4) 0.067(2) Uani 1 1 d . . .
H2 H 0.1757 0.6212 0.2715 0.080 Uiso 1 1 calc R . .
C3 C 0.1436(2) 0.3944(11) 0.2144(4) 0.064(2) Uani 1 1 d . . .
H3 H 0.1326 0.3573 0.2411 0.077 Uiso 1 1 calc R . .
C4 C 0.1340(2) 0.2896(9) 0.1583(3) 0.0379(17) Uani 1 1 d . . .
C5 C 0.1498(2) 0.3492(9) 0.1182(3) 0.0463(19) Uani 1 1 d . . .
H5 H 0.1436 0.2797 0.0799 0.056 Uiso 1 1 calc R . .
C6 C 0.1745(2) 0.5098(10) 0.1343(4) 0.061(2) Uani 1 1 d . . .
H6 H 0.1844 0.5503 0.1067 0.073 Uiso 1 1 calc R . .
C7 C 0.1051(2) 0.1194(8) 0.1387(3) 0.0438(18) Uani 1 1 d . . .
H7A H 0.1172 0.0413 0.1796 0.053 Uiso 1 1 calc R . .
H7B H 0.1062 0.0512 0.1034 0.053 Uiso 1 1 calc R . .
C8 C 0.0435(3) 0.1769(9) 0.1555(4) 0.054(2) Uani 1 1 d . . .
H8 H 0.0645 0.1390 0.2014 0.065 Uiso 1 1 calc R . .
C9 C 0.0029(3) 0.2364(9) 0.1391(4) 0.052(2) Uani 1 1 d . . .
H9 H -0.0040 0.2440 0.1726 0.063 Uiso 1 1 calc R . .
C10 C -0.0274(3) 0.2847(9) 0.0720(5) 0.057(2) Uani 1 1 d . . .
H10 H -0.0560 0.3267 0.0590 0.068 Uiso 1 1 calc R . .
C11 C -0.0177(2) 0.2742(8) 0.0203(4) 0.0404(17) Uani 1 1 d . . .
C12 C -0.0498(2) 0.3148(8) -0.0514(4) 0.056(2) Uani 1 1 d . . .
H12 H -0.0789 0.3554 -0.0663 0.068 Uiso 1 1 calc R . .
C13 C -0.0383(3) 0.2948(9) -0.0991(4) 0.056(2) Uani 1 1 d . . .
H13 H -0.0599 0.3211 -0.1462 0.067 Uiso 1 1 calc R . .
C14 C 0.0042(2) 0.2368(8) -0.0787(4) 0.0485(19) Uani 1 1 d . . .
H14 H 0.0113 0.2235 -0.1119 0.058 Uiso 1 1 calc R . .
C15 C 0.0365(2) 0.1983(7) -0.0098(4) 0.0403(17) Uani 1 1 d . . .
H15 H 0.0658 0.1625 0.0045 0.048 Uiso 1 1 calc R . .
C16 C 0.0247(2) 0.2136(7) 0.0398(3) 0.0353(17) Uani 1 1 d . . .
C17 C 0.1333(2) 0.8246(10) 0.3341(4) 0.049(2) Uani 1 1 d . . .
C18 C 0.1245(2) 0.6953(10) 0.4223(4) 0.051(2) Uani 1 1 d . . .
C19 C 0.1529(2) 0.7607(9) 0.4029(3) 0.0423(18) Uani 1 1 d . . .
C20 C 0.2014(2) 0.7562(8) 0.4514(3) 0.0404(17) Uani 1 1 d . . .
C21 C 0.2321(2) 0.8182(8) 0.4332(3) 0.0441(18) Uani 1 1 d . . .
H21 H 0.2201 0.8650 0.3884 0.053 Uiso 1 1 calc R . .
C22 C 0.2221(2) 0.6897(8) 0.5208(3) 0.0414(18) Uani 1 1 d . . .
H22 H 0.2035 0.6501 0.5352 0.050 Uiso 1 1 calc R . .
C23 C 0.1223(3) 0.2556(9) 0.3749(4) 0.051(2) Uani 1 1 d . . .
C24 C 0.1410(2) 0.1300(10) 0.4845(4) 0.046(2) Uani 1 1 d . . .
C25 C 0.1554(2) 0.2027(9) 0.4428(3) 0.0405(17) Uani 1 1 d . . .
C26 C 0.2025(2) 0.2275(8) 0.4720(4) 0.0399(17) Uani 1 1 d . . .
C27 C 0.2185(2) 0.2988(9) 0.4322(3) 0.0434(18) Uani 1 1 d . . .
H27 H 0.1971 0.3326 0.3859 0.052 Uiso 1 1 calc R . .
C28 C 0.2360(2) 0.1794(8) 0.5417(3) 0.0436(17) Uani 1 1 d . . .
H28 H 0.2274 0.1324 0.5703 0.052 Uiso 1 1 calc R . .
C29 C 0.0000 0.5967(16) 0.2500 0.098(5) Uani 1 2 d S . .
C30 C 0.0000 0.7902(19) 0.2500 0.075(4) Uani 1 2 d S . .
N1 N 0.05618(17) 0.1680(6) 0.1105(3) 0.0401(14) Uani 1 1 d . . .
N2 N 0.0000 0.9492(16) 0.2500 0.126(5) Uani 1 2 d S . .
N3 N 0.1177(2) 0.8700(9) 0.2774(3) 0.078(2) Uani 1 1 d . . .
N4 N 0.1007(2) 0.6379(9) 0.4364(3) 0.074(2) Uani 1 1 d . . .
N5 N 0.0944(2) 0.3001(8) 0.3180(3) 0.0668(19) Uani 1 1 d . . .
N6 N 0.12925(19) 0.0773(8) 0.5187(3) 0.0625(19) 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
Br1 C1 1.902(7) . ?
C1 C2 1.361(8) . ?
C1 C6 1.380(8) . ?
C2 C3 1.377(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(7) . ?
C4 C7 1.505(8) . ?
C5 C6 1.379(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.508(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.335(9) . ?
C8 N1 1.338(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.343(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.412(8) . ?
C10 H10 0.9300 . ?
C11 C16 1.372(8) . ?
C11 C12 1.414(8) . ?
C12 C13 1.372(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.419(7) . ?
C15 H15 0.9300 . ?
C16 N1 1.401(7) . ?
C17 N3 1.144(7) . ?
C17 C19 1.404(8) . ?
C18 N4 1.135(8) . ?
C18 C19 1.389(9) . ?
C19 C20 1.428(8) . ?
C20 C22 1.418(7) . ?
C20 C21 1.434(8) . ?
C21 C22 1.351(8) 7_566 ?
C21 H21 0.9300 . ?
C22 C21 1.351(8) 7_566 ?
C22 H22 0.9300 . ?
C23 N5 1.160(8) . ?
C23 C25 1.383(9) . ?
C24 N6 1.141(7) . ?
C24 C25 1.416(8) . ?
C25 C26 1.412(8) . ?
C26 C28 1.402(8) . ?
C26 C27 1.417(8) . ?
C27 C28 1.375(8) 7_556 ?
C27 H27 0.9300 . ?
C28 C27 1.375(8) 7_556 ?
C28 H28 0.9300 . ?
C29 C30 1.407(15) . ?
C30 N2 1.156(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.4(7) . . ?
C2 C1 Br1 119.7(6) . . ?
C6 C1 Br1 119.0(6) . . ?
C1 C2 C3 118.8(7) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 121.9(7) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 118.2(7) . . ?
C3 C4 C7 120.7(6) . . ?
C5 C4 C7 121.1(6) . . ?
C6 C5 C4 121.1(6) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 118.6(7) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
C4 C7 N1 111.0(5) . . ?
C4 C7 H7A 109.4 . . ?
N1 C7 H7A 109.4 . . ?
C4 C7 H7B 109.4 . . ?
N1 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 N1 124.7(7) . . ?
C9 C8 H8 117.7 . . ?
N1 C8 H8 117.7 . . ?
C8 C9 C10 116.6(7) . . ?
C8 C9 H9 121.7 . . ?
C10 C9 H9 121.7 . . ?
C9 C10 C11 122.7(7) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
C16 C11 C10 118.5(7) . . ?
C16 C11 C12 117.8(7) . . ?
C10 C11 C12 123.7(7) . . ?
C13 C12 C11 120.4(7) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 121.2(7) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 120.3(7) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.1(6) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C11 C16 N1 117.9(6) . . ?
C11 C16 C15 121.2(7) . . ?
N1 C16 C15 120.9(6) . . ?
N3 C17 C19 177.2(8) . . ?
N4 C18 C19 177.8(8) . . ?
C18 C19 C17 118.9(6) . . ?
C18 C19 C20 120.5(6) . . ?
C17 C19 C20 120.5(6) . . ?
C22 C20 C19 121.6(6) . . ?
C22 C20 C21 115.9(6) . . ?
C19 C20 C21 122.4(6) . . ?
C22 C21 C20 121.8(6) 7_566 . ?
C22 C21 H21 119.1 7_566 . ?
C20 C21 H21 119.1 . . ?
C21 C22 C20 122.2(6) 7_566 . ?
C21 C22 H22 118.9 7_566 . ?
C20 C22 H22 118.9 . . ?
N5 C23 C25 179.8(9) . . ?
N6 C24 C25 177.7(8) . . ?
C23 C25 C26 122.0(6) . . ?
C23 C25 C24 118.0(6) . . ?
C26 C25 C24 119.9(6) . . ?
C28 C26 C25 121.9(7) . . ?
C28 C26 C27 116.2(6) . . ?
C25 C26 C27 121.9(6) . . ?
C28 C27 C26 123.5(6) 7_556 . ?
C28 C27 H27 118.2 7_556 . ?
C26 C27 H27 118.2 . . ?
C27 C28 C26 120.3(6) 7_556 . ?
C27 C28 H28 119.9 7_556 . ?
C26 C28 H28 119.9 . . ?
N2 C30 C29 180.000(7) . . ?
C8 N1 C16 119.5(6) . . ?
C8 N1 C7 118.5(6) . . ?
C16 N1 C7 121.9(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
C6 C1 C2 C3 -0.1(12) . . . . ?
Br1 C1 C2 C3 178.9(6) . . . . ?
C1 C2 C3 C4 1.4(12) . . . . ?
C2 C3 C4 C5 -1.3(10) . . . . ?
C2 C3 C4 C7 -178.3(7) . . . . ?
C3 C4 C5 C6 -0.1(9) . . . . ?
C7 C4 C5 C6 176.9(6) . . . . ?
C4 C5 C6 C1 1.3(10) . . . . ?
C2 C1 C6 C5 -1.2(11) . . . . ?
Br1 C1 C6 C5 179.7(5) . . . . ?
C3 C4 C7 N1 69.0(7) . . . . ?
C5 C4 C7 N1 -107.9(6) . . . . ?
N1 C8 C9 C10 2.2(10) . . . . ?
C8 C9 C10 C11 0.0(10) . . . . ?
C9 C10 C11 C16 -0.5(9) . . . . ?
C9 C10 C11 C12 176.5(6) . . . . ?
C16 C11 C12 C13 -0.5(9) . . . . ?
C10 C11 C12 C13 -177.5(6) . . . . ?
C11 C12 C13 C14 -0.5(10) . . . . ?
C12 C13 C14 C15 -0.3(10) . . . . ?
C13 C14 C15 C16 2.0(9) . . . . ?
C10 C11 C16 N1 -1.0(8) . . . . ?
C12 C11 C16 N1 -178.1(5) . . . . ?
C10 C11 C16 C15 179.4(5) . . . . ?
C12 C11 C16 C15 2.2(9) . . . . ?
C14 C15 C16 C11 -3.0(9) . . . . ?
C14 C15 C16 N1 177.3(5) . . . . ?
N4 C18 C19 C17 57(24) . . . . ?
N4 C18 C19 C20 -121(23) . . . . ?
N3 C17 C19 C18 -98(18) . . . . ?
N3 C17 C19 C20 79(18) . . . . ?
C18 C19 C20 C22 -1.5(10) . . . . ?
C17 C19 C20 C22 -179.0(6) . . . . ?
C18 C19 C20 C21 178.5(6) . . . . ?
C17 C19 C20 C21 1.0(10) . . . . ?
C22 C20 C21 C22 1.1(10) . . . 7_566 ?
C19 C20 C21 C22 -178.9(6) . . . 7_566 ?
C19 C20 C22 C21 178.9(6) . . . 7_566 ?
C21 C20 C22 C21 -1.2(10) . . . 7_566 ?
N5 C23 C25 C26 -145(100) . . . . ?
N5 C23 C25 C24 32(100) . . . . ?
N6 C24 C25 C23 -85(20) . . . . ?
N6 C24 C25 C26 91(20) . . . . ?
C23 C25 C26 C28 177.9(6) . . . . ?
C24 C25 C26 C28 1.1(9) . . . . ?
C23 C25 C26 C27 -3.6(10) . . . . ?
C24 C25 C26 C27 179.7(6) . . . . ?
C28 C26 C27 C28 0.3(10) . . . 7_556 ?
C25 C26 C27 C28 -178.3(6) . . . 7_556 ?
C25 C26 C28 C27 178.3(6) . . . 7_556 ?
C27 C26 C28 C27 -0.3(10) . . . 7_556 ?
C9 C8 N1 C16 -3.7(10) . . . . ?
C9 C8 N1 C7 172.8(6) . . . . ?
C11 C16 N1 C8 3.0(8) . . . . ?
C15 C16 N1 C8 -177.4(5) . . . . ?
C11 C16 N1 C7 -173.4(5) . . . . ?
C15 C16 N1 C7 6.2(8) . . . . ?
C4 C7 N1 C8 -91.6(7) . . . . ?
C4 C7 N1 C16 84.9(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.926
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.100

#===========END


