# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 207/494

data_r3296_19_1

_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
  ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
  'C24 H27 N'
_chemical_formula_weight          329.47

loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
  'C'  'C'   0.0181   0.0091
  'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
  'H'  'H'   0.0000   0.0000
  'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
  'N'  'N'   0.0311   0.0180
  'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting            orthorhombic
_symmetry_space_group_name_H-M    P2(1)2(1)2(1)

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

_cell_length_a                    8.6255(3)
_cell_length_b                    9.9353(4)
_cell_length_c                    22.5592(7)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1933.25(12)
_cell_formula_units_Z             4
_cell_measurement_temperature     160(2)
_cell_measurement_reflns_used     68
_cell_measurement_theta_min       21.0
_cell_measurement_theta_max       25.1

_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.32
_exptl_crystal_size_min           0.28
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.132
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              712
_exptl_absorpt_coefficient_mu     0.486
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?

_exptl_special_details
;
  ?
;

_diffrn_ambient_temperature       160(2)
_diffrn_radiation_wavelength      1.54184
_diffrn_radiation_type            CuK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Stoe-Siemens diffractometer'
_diffrn_measurement_method        '\w/\q scans with on-line profile fitting'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          5
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   60
_diffrn_standards_decay_%         0
_diffrn_reflns_number             7381
_diffrn_reflns_av_R_equivalents   0.0325
_diffrn_reflns_av_sigmaI/netI     0.0302
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -27
_diffrn_reflns_limit_l_max        27
_diffrn_reflns_theta_min          3.92
_diffrn_reflns_theta_max          67.53
_reflns_number_total              3266
_reflns_number_gt                 3173
_reflns_threshold_expression      >2sigma(I)

_computing_data_collection        'Stoe DIF4'
_computing_cell_refinement        'Stoe DIF4'
_computing_data_reduction         'local programs'
_computing_structure_solution     'Siemens SHELXTL'
_computing_structure_refinement   'Siemens SHELXTL'
_computing_molecular_graphics     'Siemens SHELXTL'
_computing_publication_material   'SHELXTL and local programs'

_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^)+(0.0442P)^2^+0.2175P] 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     mixed
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.0071(5)
_refine_ls_extinction_expression
  'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_abs_structure_details
  'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    -0.1(6)
_refine_ls_number_reflns          3266
_refine_ls_number_parameters      230
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0322
_refine_ls_R_factor_gt            0.0311
_refine_ls_wR_factor_ref          0.0827
_refine_ls_wR_factor_gt           0.0809
_refine_ls_goodness_of_fit_ref    1.050
_refine_ls_restrained_S_all       1.050
_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
N N 0.52320(13) 0.63563(11) 0.35259(4) 0.0286(2) Uani 1 1 d . . .
C11 C 0.52222(15) 0.48864(13) 0.35579(5) 0.0288(3) Uani 1 1 d . . .
H11 H 0.5461 0.4555 0.3149 0.035 Uiso 1 1 calc R . .
C12 C 0.36546(17) 0.42752(16) 0.37274(7) 0.0418(4) Uani 1 1 d . . .
H12A H 0.2872 0.4541 0.3435 0.063 Uiso 1 1 calc R . .
H12B H 0.3347 0.4602 0.4120 0.063 Uiso 1 1 calc R . .
H12C H 0.3741 0.3292 0.3736 0.063 Uiso 1 1 calc R . .
C13 C 0.65518(16) 0.44183(13) 0.39514(5) 0.0288(3) Uani 1 1 d . . .
C14 C 0.80454(16) 0.43976(15) 0.37212(6) 0.0373(3) Uani 1 1 d . . .
H14 H 0.8209 0.4615 0.3316 0.045 Uiso 1 1 calc R . .
C15 C 0.92992(19) 0.40645(17) 0.40754(8) 0.0481(4) Uani 1 1 d . . .
H15 H 1.0313 0.4046 0.3911 0.058 Uiso 1 1 calc R . .
C16 C 0.9082(2) 0.37580(17) 0.46687(8) 0.0511(4) Uani 1 1 d . . .
H16 H 0.9944 0.3548 0.4914 0.061 Uiso 1 1 calc R . .
C17 C 0.7610(2) 0.37609(15) 0.48995(7) 0.0468(4) Uani 1 1 d . . .
H17 H 0.7453 0.3548 0.5306 0.056 Uiso 1 1 calc R . .
C18 C 0.63503(18) 0.40727(14) 0.45434(6) 0.0360(3) Uani 1 1 d . . .
H18 H 0.5335 0.4050 0.4706 0.043 Uiso 1 1 calc R . .
C21 C 0.48536(15) 0.71349(14) 0.40566(5) 0.0302(3) Uani 1 1 d . . .
H21 H 0.4935 0.6501 0.4399 0.036 Uiso 1 1 calc R . .
C22 C 0.31930(17) 0.76911(16) 0.40639(7) 0.0430(4) Uani 1 1 d . . .
H22A H 0.2454 0.6942 0.4064 0.064 Uiso 1 1 calc R . .
H22B H 0.3024 0.8249 0.3711 0.064 Uiso 1 1 calc R . .
H22C H 0.3041 0.8237 0.4421 0.064 Uiso 1 1 calc R . .
C23 C 0.60911(16) 0.82107(13) 0.41509(5) 0.0307(3) Uani 1 1 d . . .
C24 C 0.58443(19) 0.95766(14) 0.40556(6) 0.0386(3) Uani 1 1 d . . .
H24 H 0.4833 0.9887 0.3960 0.046 Uiso 1 1 calc R . .
C25 C 0.7057(2) 1.04967(15) 0.40985(6) 0.0458(4) Uani 1 1 d . . .
H25 H 0.6868 1.1424 0.4025 0.055 Uiso 1 1 calc R . .
C26 C 0.8523(2) 1.00762(16) 0.42463(6) 0.0439(4) Uani 1 1 d . . .
H26 H 0.9348 1.0707 0.4274 0.053 Uiso 1 1 calc R . .
C27 C 0.87880(19) 0.87227(16) 0.43552(6) 0.0417(4) Uani 1 1 d . . .
H27 H 0.9795 0.8424 0.4463 0.050 Uiso 1 1 calc R . .
C28 C 0.75856(16) 0.78058(14) 0.43064(6) 0.0350(3) Uani 1 1 d . . .
H28 H 0.7783 0.6880 0.4381 0.042 Uiso 1 1 calc R . .
C31 C 0.51371(15) 0.70211(14) 0.29473(5) 0.0304(3) Uani 1 1 d . . .
H31 H 0.5013 0.8003 0.3032 0.036 Uiso 1 1 calc R . .
C32 C 0.37193(17) 0.66172(18) 0.25774(6) 0.0423(4) Uani 1 1 d . . .
H32A H 0.2771 0.6829 0.2798 0.064 Uiso 1 1 calc R . .
H32B H 0.3756 0.5649 0.2496 0.064 Uiso 1 1 calc R . .
H32C H 0.3725 0.7115 0.2202 0.064 Uiso 1 1 calc R . .
C33 C 0.66655(15) 0.68833(13) 0.26152(5) 0.0285(3) Uani 1 1 d . . .
C34 C 0.69300(17) 0.59052(14) 0.21831(5) 0.0347(3) Uani 1 1 d . . .
H34 H 0.6113 0.5315 0.2073 0.042 Uiso 1 1 calc R . .
C35 C 0.83655(18) 0.57803(15) 0.19112(6) 0.0398(3) Uani 1 1 d . . .
H35 H 0.8524 0.5101 0.1621 0.048 Uiso 1 1 calc R . .
C36 C 0.95619(18) 0.66349(16) 0.20590(6) 0.0414(4) Uani 1 1 d . . .
H36 H 1.0546 0.6546 0.1874 0.050 Uiso 1 1 calc R . .
C37 C 0.93116(17) 0.76275(16) 0.24805(6) 0.0401(3) Uani 1 1 d . . .
H37 H 1.0125 0.8230 0.2581 0.048 Uiso 1 1 calc R . .
C38 C 0.78875(16) 0.77452(14) 0.27550(6) 0.0340(3) Uani 1 1 d . . .
H38 H 0.7737 0.8427 0.3045 0.041 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
N 0.0347(6) 0.0267(5) 0.0244(5) -0.0005(4) -0.0003(5) 0.0026(5)
C11 0.0297(7) 0.0280(6) 0.0288(6) -0.0023(5) 0.0012(5) -0.0027(6)
C12 0.0345(8) 0.0464(9) 0.0444(7) 0.0000(7) 0.0012(6) -0.0104(7)
C13 0.0342(7) 0.0197(5) 0.0324(6) -0.0025(5) 0.0002(5) 0.0003(6)
C14 0.0340(8) 0.0359(7) 0.0419(7) -0.0021(6) 0.0032(6) 0.0031(7)
C15 0.0328(8) 0.0477(9) 0.0636(10) -0.0091(8) -0.0058(7) 0.0060(7)
C16 0.0555(10) 0.0419(9) 0.0559(10) -0.0097(7) -0.0228(8) 0.0149(8)
C17 0.0664(11) 0.0375(8) 0.0366(7) -0.0014(6) -0.0106(7) 0.0111(8)
C18 0.0448(8) 0.0294(6) 0.0337(6) 0.0004(5) 0.0027(6) 0.0023(6)
C21 0.0313(7) 0.0326(6) 0.0267(6) -0.0009(5) 0.0025(5) 0.0059(6)
C22 0.0350(8) 0.0476(9) 0.0463(8) -0.0011(7) 0.0051(6) 0.0111(7)
C23 0.0399(7) 0.0305(7) 0.0217(5) -0.0030(5) 0.0014(5) 0.0046(6)
C24 0.0538(9) 0.0329(7) 0.0290(6) -0.0031(5) -0.0019(6) 0.0094(7)
C25 0.0758(12) 0.0288(7) 0.0328(7) -0.0025(6) -0.0016(7) -0.0039(8)
C26 0.0593(10) 0.0423(8) 0.0301(7) -0.0053(6) -0.0011(7) -0.0144(8)
C27 0.0424(9) 0.0490(9) 0.0338(7) -0.0044(6) -0.0046(6) -0.0040(7)
C28 0.0391(8) 0.0327(7) 0.0331(6) -0.0027(5) -0.0044(6) 0.0008(6)
C31 0.0325(7) 0.0308(6) 0.0278(6) 0.0018(5) -0.0041(5) 0.0022(6)
C32 0.0349(8) 0.0557(9) 0.0365(7) 0.0033(7) -0.0094(6) -0.0001(7)
C33 0.0335(7) 0.0289(6) 0.0230(5) 0.0038(5) -0.0045(5) -0.0008(6)
C34 0.0416(8) 0.0326(7) 0.0298(6) -0.0042(5) 0.0001(6) -0.0081(6)
C35 0.0482(9) 0.0375(7) 0.0336(7) -0.0057(6) 0.0069(6) -0.0050(7)
C36 0.0384(8) 0.0485(9) 0.0373(7) -0.0018(6) 0.0058(6) -0.0036(7)
C37 0.0363(7) 0.0450(8) 0.0390(7) -0.0053(6) -0.0008(6) -0.0108(7)
C38 0.0386(8) 0.0332(7) 0.0302(6) -0.0039(5) -0.0030(5) -0.0035(6)

_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
N C21 1.4622(16) . ?
N C11 1.4622(16) . ?
N C31 1.4652(15) . ?
C11 C13 1.5230(18) . ?
C11 C12 1.5307(19) . ?
C13 C14 1.3892(19) . ?
C13 C18 1.3899(18) . ?
C14 C15 1.385(2) . ?
C15 C16 1.386(2) . ?
C16 C17 1.372(3) . ?
C17 C18 1.386(2) . ?
C21 C23 1.5255(19) . ?
C21 C22 1.535(2) . ?
C23 C24 1.3904(19) . ?
C23 C28 1.395(2) . ?
C24 C25 1.392(2) . ?
C25 C26 1.373(2) . ?
C26 C27 1.386(2) . ?
C27 C28 1.385(2) . ?
C31 C33 1.5225(18) . ?
C31 C32 1.5339(18) . ?
C33 C38 1.3942(18) . ?
C33 C34 1.3952(18) . ?
C34 C35 1.387(2) . ?
C35 C36 1.377(2) . ?
C36 C37 1.387(2) . ?
C37 C38 1.381(2) . ?

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
C21 N C11 119.12(10) . . ?
C21 N C31 118.58(10) . . ?
C11 N C31 119.60(10) . . ?
N C11 C13 109.23(10) . . ?
N C11 C12 114.43(12) . . ?
C13 C11 C12 113.48(11) . . ?
C14 C13 C18 118.13(13) . . ?
C14 C13 C11 119.01(11) . . ?
C18 C13 C11 122.78(12) . . ?
C15 C14 C13 120.81(13) . . ?
C14 C15 C16 120.27(15) . . ?
C17 C16 C15 119.43(14) . . ?
C16 C17 C18 120.38(14) . . ?
C17 C18 C13 120.94(14) . . ?
N C21 C23 109.19(10) . . ?
N C21 C22 114.04(11) . . ?
C23 C21 C22 113.52(11) . . ?
C24 C23 C28 117.50(13) . . ?
C24 C23 C21 123.73(13) . . ?
C28 C23 C21 118.65(12) . . ?
C23 C24 C25 121.00(14) . . ?
C26 C25 C24 120.60(14) . . ?
C25 C26 C27 119.33(15) . . ?
C28 C27 C26 120.06(15) . . ?
C27 C28 C23 121.48(13) . . ?
N C31 C33 110.45(10) . . ?
N C31 C32 114.28(11) . . ?
C33 C31 C32 113.52(10) . . ?
C38 C33 C34 117.53(12) . . ?
C38 C33 C31 119.21(11) . . ?
C34 C33 C31 123.23(12) . . ?
C35 C34 C33 121.13(13) . . ?
C36 C35 C34 120.44(13) . . ?
C35 C36 C37 119.19(13) . . ?
C38 C37 C36 120.42(13) . . ?
C37 C38 C33 121.28(12) . . ?

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
C21 N C11 C13 -68.08(15) . . . . ?
C31 N C11 C13 130.78(11) . . . . ?
C21 N C11 C12 60.38(15) . . . . ?
C31 N C11 C12 -100.76(14) . . . . ?
N C11 C13 C14 -78.20(15) . . . . ?
C12 C11 C13 C14 152.81(13) . . . . ?
N C11 C13 C18 98.44(15) . . . . ?
C12 C11 C13 C18 -30.55(18) . . . . ?
C18 C13 C14 C15 -1.1(2) . . . . ?
C11 C13 C14 C15 175.69(13) . . . . ?
C13 C14 C15 C16 -0.6(2) . . . . ?
C14 C15 C16 C17 1.3(2) . . . . ?
C15 C16 C17 C18 -0.3(2) . . . . ?
C16 C17 C18 C13 -1.5(2) . . . . ?
C14 C13 C18 C17 2.2(2) . . . . ?
C11 C13 C18 C17 -174.51(13) . . . . ?
C11 N C21 C23 130.61(12) . . . . ?
C31 N C21 C23 -68.07(14) . . . . ?
C11 N C21 C22 -101.22(14) . . . . ?
C31 N C21 C22 60.10(15) . . . . ?
N C21 C23 C24 107.91(14) . . . . ?
C22 C21 C23 C24 -20.55(18) . . . . ?
N C21 C23 C28 -68.00(14) . . . . ?
C22 C21 C23 C28 163.54(12) . . . . ?
C28 C23 C24 C25 1.73(19) . . . . ?
C21 C23 C24 C25 -174.22(12) . . . . ?
C23 C24 C25 C26 -1.1(2) . . . . ?
C24 C25 C26 C27 -0.2(2) . . . . ?
C25 C26 C27 C28 0.9(2) . . . . ?
C26 C27 C28 C23 -0.3(2) . . . . ?
C24 C23 C28 C27 -1.04(19) . . . . ?
C21 C23 C28 C27 175.12(12) . . . . ?
C21 N C31 C33 125.39(12) . . . . ?
C11 N C31 C33 -73.37(14) . . . . ?
C21 N C31 C32 -105.14(14) . . . . ?
C11 N C31 C32 56.09(15) . . . . ?
N C31 C33 C38 -80.33(15) . . . . ?
C32 C31 C33 C38 149.81(13) . . . . ?
N C31 C33 C34 97.91(14) . . . . ?
C32 C31 C33 C34 -31.96(17) . . . . ?
C38 C33 C34 C35 1.2(2) . . . . ?
C31 C33 C34 C35 -177.07(12) . . . . ?
C33 C34 C35 C36 -0.7(2) . . . . ?
C34 C35 C36 C37 -0.4(2) . . . . ?
C35 C36 C37 C38 0.9(2) . . . . ?
C36 C37 C38 C33 -0.4(2) . . . . ?
C34 C33 C38 C37 -0.6(2) . . . . ?
C31 C33 C38 C37 177.70(12) . . . . ?

_diffrn_measured_fraction_theta_max    0.957
_diffrn_reflns_theta_full              67.53
_diffrn_measured_fraction_theta_full   0.957
_refine_diff_density_max    0.148
_refine_diff_density_min   -0.158
_refine_diff_density_rms    0.035

data_c3amine

_audit_creation_method            SHELXL
_chemical_name_systematic
;
  ?
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum             'C24 H27 N'
_chemical_formula_weight          329.47
_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            Rhombohedral
_symmetry_space_group_name_H-M    R-3

loop_
  _symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-y, x-y, z'
  '-x+y, -x, z'
  'x+2/3, y+1/3, z+1/3'
  '-y+2/3, x-y+1/3, z+1/3'
  '-x+y+2/3, -x+1/3, z+1/3'
  'x+1/3, y+2/3, z+2/3'
  '-y+1/3, x-y+2/3, z+2/3'
  '-x+y+1/3, -x+2/3, z+2/3'
  '-x, -y, -z'
  'y, -x+y, -z'
  'x-y, x, -z'
  '-x+2/3, -y+1/3, -z+1/3'
  'y+2/3, -x+y+1/3, -z+1/3'
  'x-y+2/3, x+1/3, -z+1/3'
  '-x+1/3, -y+2/3, -z+2/3'
  'y+1/3, -x+y+2/3, -z+2/3'
  'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                    11.522(2)
_cell_length_b                    11.522(2)
_cell_length_c                    50.079(9)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 120.00
_cell_volume                      5757.2(20)
_cell_formula_units_Z             12
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     143
_cell_measurement_theta_min       1.75
_cell_measurement_theta_max       27.5

_exptl_crystal_description        'Hexagonal Plates'
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.62
_exptl_crystal_size_mid           0.38
_exptl_crystal_size_min           0.18
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.140
_exptl_crystal_density_method     ?
_exptl_crystal_F_000              2136
_exptl_absorpt_coefficient_mu     0.065
_exptl_absorpt_correction_type    none
_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 SMART Area Detector'
_diffrn_measurement_method        '\w rotation with narrow frames'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             12373
_diffrn_reflns_av_R_equivalents   0.0388
_diffrn_reflns_av_sigmaI/netI     0.0344
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -61
_diffrn_reflns_limit_l_max        65
_diffrn_reflns_theta_min          1.22
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2942
_reflns_number_observed           2024
_reflns_observed_criterion        >2sigma(I)

_computing_data_collection        'SMART (Siemens, 1995b)'
_computing_cell_refinement        'SMART (Siemens, 1995b)'
_computing_data_reduction         'SMART (Siemens, 1995b)'
_computing_structure_solution     'SHELXTL (Siemens, 1995a)'
_computing_structure_refinement   'SHELXTL (Siemens, 1995a)'
_computing_molecular_graphics     'SHELXTL (Siemens, 1995a)'
_computing_publication_material   'SHELXTL (Siemens, 1995a)'

_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^)+(0.0517P)^2^+2.1572P] 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     noref
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2942
_refine_ls_number_parameters      151
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0744
_refine_ls_R_factor_obs           0.0443
_refine_ls_wR_factor_all          0.1156
_refine_ls_wR_factor_obs          0.1012
_refine_ls_goodness_of_fit_all    1.024
_refine_ls_goodness_of_fit_obs    1.093
_refine_ls_restrained_S_all       1.024
_refine_ls_restrained_S_obs       1.093
_refine_ls_shift/esd_max          -0.001
_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 0.0000 0.0000 0.16522(4) 0.0322(4) Uani 1 d S .
C1 C 0.13520(13) 0.02180(14) 0.16023(3) 0.0337(3) Uani 1 d . .
H1A H 0.19676(13) 0.12102(14) 0.16086(3) 0.040 Uiso 1 calc R .
C2 C 0.1567(2) -0.0237(2) 0.13276(3) 0.0461(4) Uani 1 d . .
H2A H 0.1279(2) 0.0158(2) 0.11875(3) 0.069 Uiso 1 calc R .
H2B H 0.1039(2) -0.1216(2) 0.13160(3) 0.069 Uiso 1 calc R .
H2C H 0.2519(2) 0.0057(2) 0.13041(3) 0.069 Uiso 1 calc R .
C3 C 0.17777(13) -0.03585(14) 0.18318(3) 0.0357(3) Uani 1 d . .
C4 C 0.2152(2) 0.0326(2) 0.20731(3) 0.0473(4) Uani 1 d . .
H4A H 0.2091(2) 0.1113(2) 0.20949(3) 0.057 Uiso 1 calc R .
C5 C 0.2613(2) -0.0120(2) 0.22830(3) 0.0622(5) Uani 1 d . .
H17A H 0.2886(2) 0.0373(2) 0.24452(3) 0.075 Uiso 1 calc R .
C6 C 0.2675(2) -0.1283(2) 0.22563(4) 0.0700(6) Uani 1 d . .
H6A H 0.3000(2) -0.1587(2) 0.23989(4) 0.084 Uiso 1 calc R .
C7 C 0.2265(2) -0.1992(2) 0.20227(4) 0.0637(5) Uani 1 d . .
H18A H 0.2277(2) -0.2807(2) 0.20057(4) 0.076 Uiso 1 calc R .
C8 C 0.18327(15) -0.1532(2) 0.18106(3) 0.0481(4) Uani 1 d . .
H8A H 0.15703(15) -0.2026(2) 0.16485(3) 0.058 Uiso 1 calc R .
N2 N 0.3333 0.6667 0.00007(3) 0.0286(4) Uani 1 d S .
C9 C 0.34998(13) 0.79988(12) -0.00537(2) 0.0303(3) Uani 1 d . .
H4A H 0.44804(13) 0.86512(12) -0.00360(2) 0.036 Uiso 1 calc R .
C10 C 0.31018(15) 0.82114(15) -0.03345(3) 0.0393(3) Uani 1 d . .
H10A H 0.35639(15) 0.79691(15) -0.04685(3) 0.059 Uiso 1 calc R .
H10B H 0.33568(15) 0.91546(15) -0.03568(3) 0.059 Uiso 1 calc R .
H10C H 0.21306(15) 0.76461(15) -0.03573(3) 0.059 Uiso 1 calc R .
C11 C 0.28118(12) 0.83593(12) 0.01658(2) 0.0294(3) Uani 1 d . .
C12 C 0.15934(13) 0.83088(13) 0.01292(3) 0.0336(3) Uani 1 d . .
H12A H 0.11457(13) 0.80203(13) -0.00376(3) 0.040 Uiso 1 calc R .
C13 C 0.10167(14) 0.86740(13) 0.03327(3) 0.0390(3) Uani 1 d . .
H13A H 0.01794(14) 0.86274(13) 0.03041(3) 0.047 Uiso 1 calc R .
C14 C 0.1651(2) 0.91009(15) 0.05746(3) 0.0454(4) Uani 1 d . .
H14A H 0.1262(2) 0.93595(15) 0.07128(3) 0.054 Uiso 1 calc R .
C15 C 0.2863(2) 0.9151(2) 0.06150(3) 0.0516(4) Uani 1 d . .
H15A H 0.3308(2) 0.9443(2) 0.07820(3) 0.062 Uiso 1 calc R .
C16 C 0.34284(15) 0.8776(2) 0.04132(3) 0.0420(4) Uani 1 d . .
H16A H 0.42553(15) 0.8804(2) 0.04445(3) 0.050 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 0.0286(6) 0.0286(6) 0.0394(11) 0.000 0.000 0.0143(3)
C1 0.0302(7) 0.0313(7) 0.0390(7) -0.0001(6) 0.0020(6) 0.0149(6)
C2 0.0453(9) 0.0524(9) 0.0442(9) -0.0029(7) 0.0065(7) 0.0271(8)
C3 0.0243(7) 0.0347(7) 0.0453(8) 0.0047(6) 0.0040(6) 0.0128(6)
C4 0.0399(9) 0.0537(10) 0.0443(9) 0.0017(7) -0.0001(7) 0.0204(8)
C5 0.0458(10) 0.0834(14) 0.0468(10) 0.0127(9) -0.0007(7) 0.0243(10)
C6 0.0371(9) 0.0889(15) 0.0773(13) 0.0478(12) 0.0095(9) 0.0266(10)
C7 0.0436(10) 0.0538(11) 0.0967(15) 0.0325(11) 0.0119(10) 0.0265(9)
C8 0.0368(8) 0.0403(9) 0.0677(10) 0.0074(7) 0.0042(7) 0.0196(7)
N2 0.0242(6) 0.0242(6) 0.0374(10) 0.000 0.000 0.0121(3)
C9 0.0268(6) 0.0249(6) 0.0379(7) 0.0024(5) 0.0018(5) 0.0121(5)
C10 0.0452(8) 0.0399(8) 0.0391(8) 0.0070(6) 0.0045(6) 0.0260(7)
C11 0.0280(7) 0.0215(6) 0.0382(7) 0.0029(5) 0.0010(5) 0.0119(5)
C12 0.0280(7) 0.0279(7) 0.0424(8) 0.0009(6) -0.0010(6) 0.0121(6)
C13 0.0307(7) 0.0330(7) 0.0545(9) 0.0025(6) 0.0056(6) 0.0167(6)
C14 0.0508(9) 0.0472(9) 0.0461(8) -0.0020(7) 0.0084(7) 0.0305(8)
C15 0.0598(10) 0.0662(11) 0.0403(8) -0.0119(7) -0.0083(7) 0.0401(9)
C16 0.0405(8) 0.0500(9) 0.0444(8) -0.0049(7) -0.0071(6) 0.0292(7)

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

loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
N1 C1 1.4700(14) 3 ?
N1 C1 1.4700(13) . ?
N1 C1 1.4701(13) 2 ?
C1 C3 1.526(2) . ?
C1 C2 1.535(2) . ?
C3 C4 1.389(2) . ?
C3 C8 1.389(2) . ?
C4 C5 1.387(2) . ?
C5 C6 1.384(3) . ?
C6 C7 1.369(3) . ?
C7 C8 1.386(2) . ?
N2 C9 1.4739(13) . ?
N2 C9 1.4739(13) 2_665 ?
N2 C9 1.4739(13) 3_565 ?
C9 C11 1.529(2) . ?
C9 C10 1.536(2) . ?
C11 C12 1.388(2) . ?
C11 C16 1.389(2) . ?
C12 C13 1.392(2) . ?
C13 C14 1.372(2) . ?
C14 C15 1.383(2) . ?
C15 C16 1.384(2) . ?

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 C1 117.17(5) 3 . ?
C1 N1 C1 117.16(5) 3 2 ?
C1 N1 C1 117.16(5) . 2 ?
N1 C1 C3 109.95(11) . . ?
N1 C1 C2 115.59(12) . . ?
C3 C1 C2 112.61(12) . . ?
C4 C3 C8 117.83(14) . . ?
C4 C3 C1 118.98(13) . . ?
C8 C3 C1 123.18(13) . . ?
C5 C4 C3 121.1(2) . . ?
C6 C5 C4 120.0(2) . . ?
C7 C6 C5 119.4(2) . . ?
C6 C7 C8 120.7(2) . . ?
C7 C8 C3 120.9(2) . . ?
C9 N2 C9 116.65(5) . 2_665 ?
C9 N2 C9 116.66(5) . 3_565 ?
C9 N2 C9 116.66(5) 2_665 3_565 ?
N2 C9 C11 109.55(10) . . ?
N2 C9 C10 116.21(12) . . ?
C11 C9 C10 112.21(11) . . ?
C12 C11 C16 117.68(12) . . ?
C12 C11 C9 122.97(12) . . ?
C16 C11 C9 119.34(12) . . ?
C11 C12 C13 121.07(13) . . ?
C14 C13 C12 120.38(13) . . ?
C13 C14 C15 119.32(13) . . ?
C14 C15 C16 120.21(14) . . ?
C15 C16 C11 121.34(14) . . ?

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
  C1 N1 C1 C3 -77.6(2) 3 . . . ?
  C1 N1 C1 C3 135.28(14) 2 . . . ?
  C1 N1 C1 C2 51.3(2) 3 . . . ?
  C1 N1 C1 C2 -95.87(15) 2 . . . ?
  N1 C1 C3 C4 -74.86(15) . . . . ?
  C2 C1 C3 C4 154.68(13) . . . . ?
  N1 C1 C3 C8 106.25(14) . . . . ?
  C2 C1 C3 C8 -24.2(2) . . . . ?
  C8 C3 C4 C5 2.3(2) . . . . ?
  C1 C3 C4 C5 -176.61(14) . . . . ?
  C3 C4 C5 C6 -1.6(2) . . . . ?
  C4 C5 C6 C7 -0.7(3) . . . . ?
  C5 C6 C7 C8 2.2(3) . . . . ?
  C6 C7 C8 C3 -1.4(2) . . . . ?
  C4 C3 C8 C7 -0.9(2) . . . . ?
  C1 C3 C8 C7 178.03(13) . . . . ?
  C9 N2 C9 C11 75.2(2) 2_665 . . . ?
  C9 N2 C9 C11 -140.31(13) 3_565 . . . ?
  C9 N2 C9 C10 -53.2(2) 2_665 . . . ?
  C9 N2 C9 C10 91.24(14) 3_565 . . . ?
  N2 C9 C11 C12 -104.39(13) . . . . ?
  C10 C9 C11 C12 26.2(2) . . . . ?
  N2 C9 C11 C16 76.53(15) . . . . ?
  C10 C9 C11 C16 -152.84(12) . . . . ?
  C16 C11 C12 C13 0.5(2) . . . . ?
  C9 C11 C12 C13 -178.58(12) . . . . ?
  C11 C12 C13 C14 0.4(2) . . . . ?
  C12 C13 C14 C15 -0.7(2) . . . . ?
  C13 C14 C15 C16 0.1(2) . . . . ?
  C14 C15 C16 C11 0.8(2) . . . . ?
  C12 C11 C16 C15 -1.1(2) . . . . ?
  C9 C11 C16 C15 178.03(13) . . . . ?

_refine_diff_density_max    0.163
_refine_diff_density_min   -0.195
_refine_diff_density_rms    0.036