# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2004


data_global

_journal_coden_Cambridge         440

loop_
_publ_author_name
'Angel Vidal'
'Delia Bautista'
'Maria-Mar Ortin'

_publ_contact_author_name        'Prof Angel Vidal'
_publ_contact_author_address     
;
Dep. Quimica Organica
Universidad de Murcia
Fac. Quimica
Campus Espinardo
Murcia
30100
SPAIN
;

_publ_contact_author_email       VIDAL@UM.ES

_publ_requested_journal          'New Journal of Chemistry'

_publ_section_title              
;
Persistent radical effect in the intramolecular
addition of benzylic radicals onto ketenimines: selective cross-coupling
of (alpha)-(indol-2-yl)benzyl radicals with the 1-cyano-1-methylethyl
radical
;

data_17
_database_code_depnum_ccdc_archive 'CCDC 223156'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H28 N2'
_chemical_formula_weight         440.56

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           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   10.1741(8)
_cell_length_b                   10.6139(9)
_cell_length_c                   11.3542(9)
_cell_angle_alpha                97.4250(10)
_cell_angle_beta                 90.1360(10)
_cell_angle_gamma                110.4370(10)
_cell_volume                     1137.81(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7642
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      18.05

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       \W-scan
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12460
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         26.37
_reflns_number_total             4621
_reflns_number_gt                4142
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0618P)^2^+0.2737P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    'NH free, rigid methyls, others riding'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4621
_refine_ls_number_parameters     313
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1065
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.020
_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
N1 N 0.84549(9) 0.07981(9) 0.29163(8) 0.0163(2) Uani 1 1 d . . .
N2 N 0.93718(10) 0.22105(10) 0.48425(8) 0.0185(2) Uani 1 1 d . . .
H2 H 1.0190(17) 0.2071(15) 0.4890(13) 0.033(4) Uiso 1 1 d . . .
C1 C 0.84692(12) -0.02909(11) 0.10850(10) 0.0191(2) Uani 1 1 d . . .
H1 H 0.8565 -0.0466 0.0254 0.023 Uiso 1 1 calc R . .
C2 C 0.80718(11) -0.12673(11) 0.19035(10) 0.0179(2) Uani 1 1 d . . .
C3 C 0.76908(11) -0.26860(11) 0.17724(11) 0.0198(2) Uani 1 1 d . . .
H3 H 0.7675 -0.3187 0.1012 0.024 Uiso 1 1 calc R . .
C4 C 0.73411(11) -0.33420(11) 0.27581(11) 0.0210(2) Uani 1 1 d . . .
H4 H 0.7069 -0.4303 0.2669 0.025 Uiso 1 1 calc R . .
C5 C 0.73793(12) -0.26201(12) 0.38907(11) 0.0212(2) Uani 1 1 d . . .
H5 H 0.7147 -0.3101 0.4556 0.025 Uiso 1 1 calc R . .
C6 C 0.77492(11) -0.12199(11) 0.40604(10) 0.0191(2) Uani 1 1 d . . .
H6 H 0.7781 -0.0731 0.4829 0.023 Uiso 1 1 calc R . .
C7 C 0.80739(11) -0.05559(11) 0.30540(10) 0.0167(2) Uani 1 1 d . . .
C8 C 0.86815(11) 0.09393(11) 0.17422(10) 0.0176(2) Uani 1 1 d . . .
C9 C 0.90493(12) 0.23928(11) 0.15526(10) 0.0178(2) Uani 1 1 d . . .
C10 C 1.01897(12) 0.27952(12) 0.06458(10) 0.0211(2) Uani 1 1 d . . .
H10A H 1.0947 0.2469 0.0828 0.025 Uiso 1 1 calc R . .
H10B H 1.0568 0.3786 0.0687 0.025 Uiso 1 1 calc R . .
H10C H 0.9781 0.2387 -0.0156 0.025 Uiso 1 1 calc R . .
C11 C 0.95844(11) 0.31353(11) 0.28803(10) 0.0174(2) Uani 1 1 d . . .
C12 C 0.93927(12) 0.45043(11) 0.31310(10) 0.0202(2) Uani 1 1 d . . .
H12A H 0.9690 0.4897 0.3960 0.024 Uiso 1 1 calc R . .
H12B H 0.8401 0.4380 0.2993 0.024 Uiso 1 1 calc R . .
H12C H 0.9963 0.5117 0.2601 0.024 Uiso 1 1 calc R . .
C13 C 0.86681(11) 0.20942(11) 0.36968(10) 0.0166(2) Uani 1 1 d . . .
C14 C 0.72193(12) 0.21737(12) 0.40630(10) 0.0201(2) Uani 1 1 d . . .
H14A H 0.7202 0.3097 0.4043 0.024 Uiso 1 1 calc R . .
H14B H 0.6447 0.1514 0.3528 0.024 Uiso 1 1 calc R . .
C15 C 0.70937(12) 0.18256(11) 0.53074(10) 0.0190(2) Uani 1 1 d . . .
C16 C 0.59707(12) 0.15502(12) 0.60363(11) 0.0238(3) Uani 1 1 d . . .
H16 H 0.5074 0.1503 0.5749 0.029 Uiso 1 1 calc R . .
C17 C 0.61749(13) 0.13434(13) 0.72001(11) 0.0283(3) Uani 1 1 d . . .
H17 H 0.5414 0.1157 0.7713 0.034 Uiso 1 1 calc R . .
C18 C 0.74883(14) 0.14093(13) 0.76122(11) 0.0272(3) Uani 1 1 d . . .
H18 H 0.7612 0.1270 0.8409 0.033 Uiso 1 1 calc R . .
C19 C 0.86277(12) 0.16744(12) 0.68846(10) 0.0221(2) Uani 1 1 d . . .
H19 H 0.9521 0.1710 0.7168 0.026 Uiso 1 1 calc R . .
C20 C 0.84066(12) 0.18855(11) 0.57277(10) 0.0176(2) Uani 1 1 d . . .
C21 C 0.77290(12) 0.26162(11) 0.10864(10) 0.0191(2) Uani 1 1 d D . .
C22 C 0.63902(12) 0.16384(12) 0.10945(10) 0.0218(2) Uani 1 1 d D . .
H22 H 0.6277 0.0840 0.1440 0.026 Uiso 1 1 calc R . .
C23 C 0.52196(13) 0.18090(13) 0.06075(11) 0.0268(3) Uani 1 1 d D . .
H23 H 0.4316 0.1136 0.0633 0.032 Uiso 1 1 calc R . .
C24 C 0.53642(14) 0.29545(13) 0.00866(12) 0.0299(3) Uani 1 1 d D . .
H24 H 0.4565 0.3069 -0.0252 0.036 Uiso 1 1 calc R . .
C25 C 0.66828(14) 0.39324(13) 0.00627(11) 0.0284(3) Uani 1 1 d D . .
H25 H 0.6790 0.4718 -0.0299 0.034 Uiso 1 1 calc R . .
C26 C 0.78507(13) 0.37733(12) 0.05640(10) 0.0240(3) Uani 1 1 d D . .
H26 H 0.8747 0.4461 0.0552 0.029 Uiso 1 1 calc R . .
C31 C 1.11530(11) 0.33034(11) 0.30632(10) 0.0185(2) Uani 1 1 d D . .
C32 C 1.16089(12) 0.21853(12) 0.29687(10) 0.0205(2) Uani 1 1 d D . .
H32 H 1.0930 0.1293 0.2853 0.025 Uiso 1 1 calc R . .
C33 C 1.30236(13) 0.23551(13) 0.30403(11) 0.0243(3) Uani 1 1 d D . .
H33 H 1.3300 0.1582 0.2967 0.029 Uiso 1 1 calc R . .
C34 C 1.40357(13) 0.36464(14) 0.32177(12) 0.0299(3) Uani 1 1 d D . .
H34 H 1.5005 0.3765 0.3254 0.036 Uiso 1 1 calc R . .
C35 C 1.36149(13) 0.47583(13) 0.33403(13) 0.0322(3) Uani 1 1 d D . .
H35 H 1.4300 0.5647 0.3476 0.039 Uiso 1 1 calc R . .
C36 C 1.21966(13) 0.45891(12) 0.32673(11) 0.0252(3) Uani 1 1 d D . .
H36 H 1.1931 0.5369 0.3359 0.030 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0168(5) 0.0153(5) 0.0162(5) 0.0024(3) 0.0007(3) 0.0048(4)
N2 0.0162(5) 0.0238(5) 0.0163(5) 0.0027(4) 0.0004(4) 0.0082(4)
C1 0.0213(6) 0.0178(5) 0.0176(5) 0.0016(4) 0.0012(4) 0.0066(4)
C2 0.0139(5) 0.0176(5) 0.0218(6) 0.0024(4) -0.0005(4) 0.0051(4)
C3 0.0160(5) 0.0172(5) 0.0254(6) 0.0006(4) -0.0006(4) 0.0059(4)
C4 0.0147(5) 0.0156(5) 0.0332(6) 0.0054(4) 0.0007(4) 0.0053(4)
C5 0.0157(5) 0.0214(6) 0.0278(6) 0.0104(5) 0.0017(4) 0.0057(4)
C6 0.0153(5) 0.0210(6) 0.0210(6) 0.0047(4) 0.0012(4) 0.0059(4)
C7 0.0128(5) 0.0158(5) 0.0219(6) 0.0038(4) 0.0000(4) 0.0050(4)
C8 0.0170(5) 0.0183(5) 0.0176(5) 0.0035(4) 0.0011(4) 0.0058(4)
C9 0.0204(5) 0.0154(5) 0.0170(5) 0.0019(4) 0.0009(4) 0.0056(4)
C10 0.0238(6) 0.0204(6) 0.0188(6) 0.0046(4) 0.0033(4) 0.0070(5)
C11 0.0188(5) 0.0163(5) 0.0168(5) 0.0023(4) 0.0008(4) 0.0059(4)
C12 0.0233(6) 0.0164(5) 0.0207(6) -0.0001(4) -0.0016(4) 0.0077(4)
C13 0.0166(5) 0.0159(5) 0.0171(5) 0.0012(4) -0.0002(4) 0.0060(4)
C14 0.0173(5) 0.0238(6) 0.0200(6) 0.0017(4) 0.0008(4) 0.0089(5)
C15 0.0189(5) 0.0164(5) 0.0196(6) -0.0017(4) 0.0002(4) 0.0053(4)
C16 0.0190(6) 0.0223(6) 0.0270(6) -0.0027(5) 0.0032(5) 0.0054(5)
C17 0.0272(6) 0.0266(6) 0.0243(6) 0.0004(5) 0.0113(5) 0.0022(5)
C18 0.0331(7) 0.0252(6) 0.0168(6) 0.0020(5) 0.0018(5) 0.0026(5)
C19 0.0229(6) 0.0208(6) 0.0195(6) 0.0013(4) -0.0020(4) 0.0046(5)
C20 0.0184(5) 0.0134(5) 0.0186(6) -0.0010(4) 0.0013(4) 0.0038(4)
C21 0.0232(6) 0.0190(5) 0.0150(5) -0.0009(4) -0.0009(4) 0.0084(5)
C22 0.0246(6) 0.0221(6) 0.0176(6) 0.0010(4) 0.0003(4) 0.0074(5)
C23 0.0224(6) 0.0302(7) 0.0242(6) -0.0038(5) -0.0024(5) 0.0074(5)
C24 0.0311(7) 0.0337(7) 0.0274(7) -0.0062(5) -0.0100(5) 0.0183(6)
C25 0.0392(7) 0.0223(6) 0.0259(6) -0.0013(5) -0.0088(5) 0.0152(6)
C26 0.0287(6) 0.0193(6) 0.0222(6) 0.0007(4) -0.0031(5) 0.0071(5)
C31 0.0188(6) 0.0200(5) 0.0162(5) 0.0036(4) 0.0018(4) 0.0059(4)
C32 0.0208(6) 0.0195(6) 0.0205(6) 0.0044(4) 0.0029(4) 0.0054(5)
C33 0.0233(6) 0.0266(6) 0.0256(6) 0.0066(5) 0.0054(5) 0.0112(5)
C34 0.0168(6) 0.0340(7) 0.0388(8) 0.0107(6) 0.0043(5) 0.0067(5)
C35 0.0209(6) 0.0241(6) 0.0459(8) 0.0083(6) 0.0006(5) -0.0003(5)
C36 0.0237(6) 0.0200(6) 0.0307(7) 0.0048(5) 0.0005(5) 0.0057(5)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C8 1.3717(14) . ?
N1 C7 1.3819(14) . ?
N1 C13 1.4834(14) . ?
N2 C20 1.3969(14) . ?
N2 C13 1.4534(14) . ?
C1 C8 1.3634(16) . ?
C1 C2 1.4350(16) . ?
C2 C3 1.4050(15) . ?
C2 C7 1.4215(16) . ?
C3 C4 1.3763(17) . ?
C4 C5 1.4024(17) . ?
C5 C6 1.3865(16) . ?
C6 C7 1.3996(16) . ?
C8 C9 1.4998(15) . ?
C9 C10 1.5369(15) . ?
C9 C21 1.5467(15) . ?
C9 C11 1.6060(15) . ?
C11 C12 1.5238(15) . ?
C11 C31 1.5529(15) . ?
C11 C13 1.5808(15) . ?
C13 C14 1.5600(15) . ?
C14 C15 1.5006(16) . ?
C15 C16 1.3820(16) . ?
C15 C20 1.3950(16) . ?
C16 C17 1.3938(18) . ?
C17 C18 1.3902(19) . ?
C18 C19 1.3937(17) . ?
C19 C20 1.3914(16) . ?
C21 C22 1.3956(16) . ?
C21 C26 1.3993(16) . ?
C22 C23 1.3894(17) . ?
C23 C24 1.3824(19) . ?
C24 C25 1.3831(19) . ?
C25 C26 1.3878(17) . ?
C31 C36 1.3959(16) . ?
C31 C32 1.4096(16) . ?
C32 C33 1.3876(16) . ?
C33 C34 1.3861(18) . ?
C34 C35 1.3807(19) . ?
C35 C36 1.3914(18) . ?

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
C8 N1 C7 109.39(9) . . ?
C8 N1 C13 113.99(9) . . ?
C7 N1 C13 136.62(9) . . ?
C20 N2 C13 111.19(9) . . ?
C8 C1 C2 106.06(10) . . ?
C3 C2 C7 118.70(10) . . ?
C3 C2 C1 133.50(11) . . ?
C7 C2 C1 107.80(10) . . ?
C4 C3 C2 119.21(11) . . ?
C3 C4 C5 121.30(10) . . ?
C6 C5 C4 121.40(11) . . ?
C5 C6 C7 117.31(11) . . ?
N1 C7 C6 131.68(10) . . ?
N1 C7 C2 106.25(9) . . ?
C6 C7 C2 122.06(10) . . ?
C1 C8 N1 110.50(10) . . ?
C1 C8 C9 138.63(10) . . ?
N1 C8 C9 110.84(9) . . ?
C8 C9 C10 111.70(9) . . ?
C8 C9 C21 109.69(9) . . ?
C10 C9 C21 108.37(9) . . ?
C8 C9 C11 100.02(8) . . ?
C10 C9 C11 113.02(9) . . ?
C21 C9 C11 113.86(9) . . ?
C12 C11 C31 110.71(9) . . ?
C12 C11 C13 111.80(9) . . ?
C31 C11 C13 109.35(9) . . ?
C12 C11 C9 112.43(9) . . ?
C31 C11 C9 108.41(9) . . ?
C13 C11 C9 103.87(8) . . ?
N2 C13 N1 114.01(9) . . ?
N2 C13 C14 102.18(9) . . ?
N1 C13 C14 109.85(8) . . ?
N2 C13 C11 112.81(9) . . ?
N1 C13 C11 99.97(8) . . ?
C14 C13 C11 118.55(9) . . ?
C15 C14 C13 104.04(9) . . ?
C16 C15 C20 120.50(11) . . ?
C16 C15 C14 130.98(11) . . ?
C20 C15 C14 108.44(10) . . ?
C15 C16 C17 118.89(11) . . ?
C18 C17 C16 120.20(11) . . ?
C17 C18 C19 121.57(11) . . ?
C20 C19 C18 117.44(11) . . ?
C19 C20 C15 121.40(11) . . ?
C19 C20 N2 128.77(10) . . ?
C15 C20 N2 109.81(10) . . ?
C22 C21 C26 117.53(11) . . ?
C22 C21 C9 121.62(10) . . ?
C26 C21 C9 120.71(10) . . ?
C23 C22 C21 121.31(11) . . ?
C24 C23 C22 120.25(11) . . ?
C23 C24 C25 119.38(11) . . ?
C24 C25 C26 120.46(12) . . ?
C25 C26 C21 121.06(11) . . ?
C36 C31 C32 116.51(11) . . ?
C36 C31 C11 120.99(10) . . ?
C32 C31 C11 122.40(10) . . ?
C33 C32 C31 121.69(11) . . ?
C34 C33 C32 120.35(11) . . ?
C35 C34 C33 119.07(11) . . ?
C34 C35 C36 120.62(11) . . ?
C35 C36 C31 121.72(11) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.048

#===END

data_10d
_database_code_depnum_ccdc_archive 'CCDC 223157'

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C26 H24 N2'
_chemical_formula_weight         364.47
_chemical_melting_point          ?
_chemical_compound_source        ?

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   P2(1)/n

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

_cell_length_a                   7.6460(10)
_cell_length_b                   21.303(2)
_cell_length_c                   12.5050(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.870(10)
_cell_angle_gamma                90.00
_cell_volume                     1968.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    100
_cell_measurement_theta_min      4.6
_cell_measurement_theta_max      12.3

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       \w-scans
_diffrn_standards_number         3
_diffrn_standards_interval_count 247
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3892
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0706
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.33
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3457
_reflns_number_observed          2172
_reflns_observed_criterion       >2sigma(I)

_computing_data_collection       'Siemens XSCANS'
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'

_refine_special_details          
;
Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^
or flagged by the user for potential systematic errors.  Weighted R-factors
wR and all goodnesses of fit S are based on F^2^, conventional R-factors R
are based on F, with F set to zero for negative F^2^. The observed criterion
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ 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 w=1/[\s^2^(Fo^2^)+(0.0413P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    'H0 free, rigid methyls, others riding'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3457
_refine_ls_number_parameters     260
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_obs          0.0400
_refine_ls_wR_factor_all         0.0882
_refine_ls_wR_factor_obs         0.0804
_refine_ls_goodness_of_fit_all   0.858
_refine_ls_goodness_of_fit_obs   1.010
_refine_ls_restrained_S_all      0.855
_refine_ls_restrained_S_obs      1.005
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N1 N 0.4598(2) 0.10749(7) 0.24151(12) 0.0220(4) Uani 1 d D .
H0 H 0.4015(27) 0.1051(9) 0.2911(16) 0.035(6) Uiso 1 d . .
N2 N 1.0958(2) 0.11059(9) 0.30203(14) 0.0359(4) Uani 1 d . .
C1 C 0.6136(2) 0.14238(8) 0.24756(14) 0.0189(4) Uani 1 d D .
C2 C 0.6501(2) 0.14086(8) 0.14578(14) 0.0216(4) Uani 1 d D .
H2 H 0.7500(2) 0.16028(8) 0.12688(14) 0.026 Uiso 1 calc R .
C3 C 0.6988(2) 0.17731(8) 0.35547(14) 0.0203(4) Uani 1 d . .
C4 C 0.8988(2) 0.19996(9) 0.35732(15) 0.0243(4) Uani 1 d . .
C5 C 1.0110(3) 0.22094(10) 0.4730(2) 0.0323(5) Uani 1 d . .
H5A H 0.9555(9) 0.2583(3) 0.4962(4) 0.039 Uiso 1 calc R .
H5B H 1.1347(5) 0.2308(5) 0.4698(3) 0.039 Uiso 1 calc R .
H5C H 1.0138(13) 0.1870(2) 0.5263(2) 0.039 Uiso 1 calc R .
C6 C 0.9003(3) 0.25565(9) 0.2783(2) 0.0323(5) Uani 1 d . .
H6A H 0.8552(14) 0.29341(15) 0.3071(5) 0.039 Uiso 1 calc R .
H6B H 0.8225(12) 0.2459(2) 0.2048(3) 0.039 Uiso 1 calc R .
H6C H 1.0242(4) 0.2630(3) 0.2727(7) 0.039 Uiso 1 calc R .
C7 C 1.0026(2) 0.14822(9) 0.3231(2) 0.0262(4) Uani 1 d . .
C8 C 0.2750(3) 0.03444(10) -0.20665(15) 0.0345(5) Uani 1 d . .
H8A H 0.1824(12) 0.0636(4) -0.2473(2) 0.041 Uiso 1 calc R .
H8B H 0.2279(15) -0.0085(2) -0.2164(2) 0.041 Uiso 1 calc R .
H8C H 0.3828(4) 0.0375(5) -0.2351(3) 0.041 Uiso 1 calc R .
C11 C 0.3955(2) 0.08409(8) 0.13629(14) 0.0204(4) Uani 1 d D .
C12 C 0.2497(2) 0.04447(8) 0.09299(14) 0.0242(4) Uani 1 d D .
H12 H 0.1756(2) 0.02893(8) 0.13749(14) 0.029 Uiso 1 calc R .
C13 C 0.2177(2) 0.02876(8) -0.01735(15) 0.0252(4) Uani 1 d D .
H13 H 0.1191(2) 0.00170(8) -0.04879(15) 0.030 Uiso 1 calc R .
C14 C 0.3246(2) 0.05113(9) -0.08498(15) 0.0243(4) Uani 1 d D .
C15 C 0.4726(2) 0.08839(8) -0.03917(15) 0.0237(4) Uani 1 d D .
H15 H 0.5481(2) 0.10287(8) -0.08358(15) 0.028 Uiso 1 calc R .
C16 C 0.5111(2) 0.10482(8) 0.07307(14) 0.0202(4) Uani 1 d D .
C21 C 0.5876(2) 0.23715(8) 0.36201(15) 0.0216(4) Uani 1 d D .
C22 C 0.4721(2) 0.26282(9) 0.2680(2) 0.0265(5) Uani 1 d D .
H22 H 0.4542(2) 0.24149(9) 0.1993(2) 0.032 Uiso 1 calc R .
C23 C 0.3823(3) 0.31903(9) 0.2723(2) 0.0336(5) Uani 1 d D .
H23 H 0.3048(3) 0.33594(9) 0.2068(2) 0.040 Uiso 1 calc R .
C24 C 0.4052(3) 0.35022(10) 0.3709(2) 0.0380(5) Uani 1 d D .
H24 H 0.3455(3) 0.38908(10) 0.3737(2) 0.046 Uiso 1 calc R .
C25 C 0.5155(3) 0.32482(9) 0.4664(2) 0.0339(5) Uani 1 d D .
H25 H 0.5290(3) 0.34565(9) 0.5352(2) 0.041 Uiso 1 calc R .
C26 C 0.6062(2) 0.26916(9) 0.4618(2) 0.0268(5) Uani 1 d D .
H26 H 0.6826(2) 0.25235(9) 0.5278(2) 0.032 Uiso 1 calc R .
C31 C 0.6902(2) 0.13167(8) 0.45055(14) 0.0222(4) Uani 1 d D .
C32 C 0.8205(3) 0.08548(9) 0.48935(15) 0.0287(5) Uani 1 d D .
H32 H 0.9244(3) 0.08362(9) 0.46105(15) 0.034 Uiso 1 calc R .
C33 C 0.8011(3) 0.04215(9) 0.5686(2) 0.0360(5) Uani 1 d D .
H33 H 0.8928(3) 0.01167(9) 0.5947(2) 0.043 Uiso 1 calc R .
C34 C 0.6502(3) 0.04291(10) 0.6097(2) 0.0372(5) Uani 1 d D .
H34 H 0.6374(3) 0.01332(10) 0.6641(2) 0.045 Uiso 1 calc R .
C35 C 0.5181(3) 0.08739(10) 0.5707(2) 0.0347(5) Uani 1 d D .
H35 H 0.4124(3) 0.08799(10) 0.5973(2) 0.042 Uiso 1 calc R .
C36 C 0.5386(3) 0.13119(9) 0.49282(15) 0.0269(5) Uani 1 d D .
H36 H 0.4466(3) 0.16171(9) 0.46762(15) 0.032 Uiso 1 calc R .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0201(9) 0.0270(9) 0.0204(9) -0.0025(7) 0.0081(7) -0.0033(7)
N2 0.0260(9) 0.0434(11) 0.0404(11) -0.0035(9) 0.0123(8) 0.0022(9)
C1 0.0161(9) 0.0169(9) 0.0238(10) -0.0005(8) 0.0052(8) 0.0002(8)
C2 0.0180(10) 0.0223(10) 0.0255(10) 0.0000(8) 0.0075(8) -0.0021(8)
C3 0.0175(10) 0.0209(9) 0.0218(10) -0.0016(8) 0.0040(8) -0.0014(8)
C4 0.0188(10) 0.0253(10) 0.0289(11) -0.0057(8) 0.0064(8) -0.0039(8)
C5 0.0232(11) 0.0361(12) 0.0355(12) -0.0101(10) 0.0039(9) -0.0059(9)
C6 0.0280(11) 0.0314(11) 0.0403(12) -0.0040(10) 0.0138(10) -0.0081(9)
C7 0.0181(10) 0.0320(11) 0.0276(11) -0.0024(9) 0.0044(9) -0.0072(9)
C8 0.0355(12) 0.0412(12) 0.0242(11) -0.0025(10) 0.0032(9) 0.0013(11)
C11 0.0195(10) 0.0218(9) 0.0192(10) -0.0007(8) 0.0035(8) 0.0010(8)
C12 0.0196(10) 0.0279(10) 0.0253(10) -0.0007(9) 0.0065(8) -0.0024(9)
C13 0.0188(10) 0.0253(10) 0.0290(11) -0.0046(9) 0.0016(9) -0.0026(9)
C14 0.0238(10) 0.0243(10) 0.0228(10) 0.0011(8) 0.0024(8) 0.0048(9)
C15 0.0232(10) 0.0249(10) 0.0249(10) 0.0040(8) 0.0098(9) 0.0029(9)
C16 0.0194(10) 0.0194(9) 0.0214(10) -0.0002(8) 0.0045(8) 0.0027(8)
C21 0.0183(9) 0.0202(9) 0.0270(10) -0.0002(8) 0.0071(8) -0.0024(8)
C22 0.0256(11) 0.0253(11) 0.0299(11) 0.0014(9) 0.0092(9) 0.0001(9)
C23 0.0270(11) 0.0272(11) 0.0459(13) 0.0070(10) 0.0079(10) 0.0030(10)
C24 0.0297(12) 0.0222(11) 0.065(2) -0.0027(11) 0.0181(11) 0.0027(10)
C25 0.0302(12) 0.0294(11) 0.0467(14) -0.0140(10) 0.0182(11) -0.0040(10)
C26 0.0239(11) 0.0275(11) 0.0302(11) -0.0035(9) 0.0092(9) -0.0026(9)
C31 0.0238(10) 0.0230(10) 0.0178(9) -0.0034(8) 0.0016(8) -0.0027(8)
C32 0.0316(11) 0.0259(10) 0.0274(11) -0.0018(9) 0.0055(9) 0.0014(9)
C33 0.0457(13) 0.0239(11) 0.0331(12) 0.0032(10) 0.0004(11) 0.0032(10)
C34 0.0522(14) 0.0265(12) 0.0294(11) 0.0047(9) 0.0039(11) -0.0109(11)
C35 0.0379(13) 0.0389(13) 0.0273(11) 0.0011(10) 0.0086(10) -0.0118(11)
C36 0.0262(11) 0.0280(11) 0.0245(10) -0.0007(9) 0.0030(9) -0.0040(9)

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

Distance H..N

2.379 (0.020)  H0 - N2_$1

Distance N..N

3.067 (0.002)  N1 - N2_$1

Angle XHY

138.01 ( 1.67)  N1 - H0 - N2_$1

;

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 C11 1.375(2) . ?
N1 C1 1.376(2) . ?
N2 C7 1.147(2) . ?
C1 C2 1.372(2) . ?
C1 C3 1.532(2) . ?
C2 C16 1.432(2) . ?
C3 C21 1.546(2) . ?
C3 C31 1.550(2) . ?
C3 C4 1.598(2) . ?
C4 C7 1.484(3) . ?
C4 C6 1.546(3) . ?
C4 C5 1.546(2) . ?
C8 C14 1.513(2) . ?
C11 C12 1.392(2) . ?
C11 C16 1.400(2) . ?
C12 C13 1.379(2) . ?
C13 C14 1.402(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.402(2) . ?
C21 C22 1.389(2) . ?
C21 C26 1.397(2) . ?
C22 C23 1.389(3) . ?
C23 C24 1.372(3) . ?
C24 C25 1.383(3) . ?
C25 C26 1.382(3) . ?
C31 C36 1.392(3) . ?
C31 C32 1.396(3) . ?
C32 C33 1.389(3) . ?
C33 C34 1.379(3) . ?
C34 C35 1.380(3) . ?
C35 C36 1.386(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
C11 N1 C1 109.8(2) . . ?
C2 C1 N1 108.1(2) . . ?
C2 C1 C3 133.4(2) . . ?
N1 C1 C3 118.34(15) . . ?
C1 C2 C16 107.9(2) . . ?
C1 C3 C21 109.38(14) . . ?
C1 C3 C31 106.18(14) . . ?
C21 C3 C31 110.17(14) . . ?
C1 C3 C4 110.38(14) . . ?
C21 C3 C4 106.70(14) . . ?
C31 C3 C4 114.01(14) . . ?
C7 C4 C6 107.1(2) . . ?
C7 C4 C5 105.95(15) . . ?
C6 C4 C5 106.4(2) . . ?
C7 C4 C3 110.62(15) . . ?
C6 C4 C3 112.73(15) . . ?
C5 C4 C3 113.56(15) . . ?
N2 C7 C4 174.2(2) . . ?
N1 C11 C12 130.3(2) . . ?
N1 C11 C16 107.7(2) . . ?
C12 C11 C16 122.0(2) . . ?
C13 C12 C11 117.1(2) . . ?
C12 C13 C14 122.7(2) . . ?
C15 C14 C13 119.2(2) . . ?
C15 C14 C8 121.3(2) . . ?
C13 C14 C8 119.5(2) . . ?
C14 C15 C16 119.9(2) . . ?
C11 C16 C15 119.0(2) . . ?
C11 C16 C2 106.50(15) . . ?
C15 C16 C2 134.5(2) . . ?
C22 C21 C26 117.5(2) . . ?
C22 C21 C3 121.2(2) . . ?
C26 C21 C3 121.2(2) . . ?
C23 C22 C21 121.3(2) . . ?
C24 C23 C22 120.2(2) . . ?
C23 C24 C25 119.7(2) . . ?
C26 C25 C24 120.1(2) . . ?
C25 C26 C21 121.3(2) . . ?
C36 C31 C32 116.9(2) . . ?
C36 C31 C3 119.9(2) . . ?
C32 C31 C3 122.8(2) . . ?
C33 C32 C31 121.3(2) . . ?
C34 C33 C32 120.7(2) . . ?
C33 C34 C35 118.8(2) . . ?
C34 C35 C36 120.5(2) . . ?
C35 C36 C31 121.8(2) . . ?

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.038

#===END