# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_l

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 monoclinic
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 N O'
_chemical_formula_weight         273.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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                   12.070(5)
_cell_length_b                   11.426(5)
_cell_length_c                   10.930(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 102.079(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1474.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9850
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12152
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2590
_reflns_number_gt                2207
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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)+(0.0593P)²+0.3314P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2590
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.004

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 0.68932(10) 0.25959(10) 0.45268(12) 0.0563(3) Uani 1 1 d . . .
C1 C 0.71589(11) 0.14333(11) 0.49708(13) 0.0480(3) Uani 1 1 d . . .
C13 C 0.75937(11) 0.35293(12) 0.50175(13) 0.0487(3) Uani 1 1 d . . .
C7 C 0.58222(11) 0.27941(12) 0.37238(13) 0.0490(3) Uani 1 1 d . . .
C6 C 0.63985(13) 0.07908(14) 0.54744(14) 0.0573(4) Uani 1 1 d . . .
H6 H 0.5705 0.1115 0.5533 0.069 Uiso 1 1 calc R . .
O1 O 0.98456(11) 0.72770(11) 0.60157(15) 0.0910(5) Uani 1 1 d . . .
C16 C 0.90102(12) 0.53935(12) 0.59768(15) 0.0562(4) Uani 1 1 d . . .
C5 C 0.66655(14) -0.03355(14) 0.58926(15) 0.0645(4) Uani 1 1 d . . .
H5 H 0.6147 -0.0768 0.6227 0.077 Uiso 1 1 calc R . .
C17 C 0.83190(12) 0.54629(13) 0.47972(16) 0.0591(4) Uani 1 1 d . . .
H17 H 0.8325 0.6138 0.4323 0.071 Uiso 1 1 calc R . .
C14 C 0.82860(12) 0.34618(13) 0.61990(14) 0.0564(4) Uani 1 1 d . . .
H14 H 0.8278 0.2794 0.6683 0.068 Uiso 1 1 calc R . .
C15 C 0.89841(13) 0.43795(13) 0.66563(15) 0.0617(4) Uani 1 1 d . . .
H15 H 0.9452 0.4316 0.7446 0.074 Uiso 1 1 calc R . .
C4 C 0.76867(14) -0.08222(14) 0.58203(15) 0.0632(4) Uani 1 1 d . . .
H4 H 0.7865 -0.1579 0.6110 0.076 Uiso 1 1 calc R . .
C3 C 0.84396(13) -0.01863(13) 0.53196(16) 0.0627(4) Uani 1 1 d . . .
H3 H 0.9134 -0.0514 0.5269 0.075 Uiso 1 1 calc R . .
C12 C 0.51145(13) 0.36579(14) 0.39938(16) 0.0653(4) Uani 1 1 d . . .
H12 H 0.5351 0.4131 0.4692 0.078 Uiso 1 1 calc R . .
C2 C 0.81848(12) 0.09365(13) 0.48865(15) 0.0573(4) Uani 1 1 d . . .
H2 H 0.8702 0.1358 0.4539 0.069 Uiso 1 1 calc R . .
C18 C 0.76244(12) 0.45483(13) 0.43179(14) 0.0567(4) Uani 1 1 d . . .
H18 H 0.7170 0.4607 0.3520 0.068 Uiso 1 1 calc R . .
C8 C 0.54630(14) 0.21010(15) 0.26905(14) 0.0643(4) Uani 1 1 d . . .
H8 H 0.5930 0.1514 0.2493 0.077 Uiso 1 1 calc R . .
C19 C 0.97680(15) 0.63473(15) 0.6494(2) 0.0749(5) Uani 1 1 d . . .
H19 H 1.0237 0.6220 0.7273 0.090 Uiso 1 1 calc R . .
C9 C 0.43960(16) 0.2285(2) 0.19427(15) 0.0791(6) Uani 1 1 d . . .
H9 H 0.4151 0.1817 0.1242 0.095 Uiso 1 1 calc R . .
C10 C 0.37015(15) 0.31451(19) 0.22236(18) 0.0793(6) Uani 1 1 d . . .
H10 H 0.2987 0.3260 0.1720 0.095 Uiso 1 1 calc R . .
C11 C 0.40642(14) 0.38290(17) 0.32438(19) 0.0786(5) Uani 1 1 d . . .
H11 H 0.3597 0.4418 0.3436 0.094 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C13 1.3965(18) . ?
N1 C1 1.4275(18) . ?
N1 C7 1.4205(18) . ?
C1 C6 1.377(2) . ?
C1 C2 1.383(2) . ?
C13 C14 1.386(2) . ?
C13 C18 1.398(2) . ?
C7 C8 1.373(2) . ?
C7 C12 1.377(2) . ?
C6 C5 1.381(2) . ?
C6 H6 0.9300 . ?
O1 C19 1.196(2) . ?
C16 C15 1.380(2) . ?
C16 C17 1.384(2) . ?
C16 C19 1.459(2) . ?
C5 C4 1.369(2) . ?
C5 H5 0.9300 . ?
C17 C18 1.373(2) . ?
C17 H17 0.9300 . ?
C14 C15 1.372(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C4 C3 1.364(2) . ?
C4 H4 0.9300 . ?
C3 C2 1.380(2) . ?
C3 H3 0.9300 . ?
C12 C11 1.372(2) . ?
C12 H12 0.9300 . ?
C2 H2 0.9300 . ?
C18 H18 0.9300 . ?
C8 C9 1.389(2) . ?
C8 H8 0.9300 . ?
C19 H19 0.9300 . ?
C9 C10 1.368(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.357(3) . ?
C10 H10 0.9300 . ?
C11 H11 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
C13 N1 C1 120.34(11) . . ?
C13 N1 C7 121.01(11) . . ?
C1 N1 C7 117.97(11) . . ?
C6 C1 C2 119.27(14) . . ?
C6 C1 N1 120.73(13) . . ?
C2 C1 N1 120.00(13) . . ?
C14 C13 N1 120.93(13) . . ?
C14 C13 C18 118.44(13) . . ?
N1 C13 C18 120.62(13) . . ?
C8 C7 C12 119.10(14) . . ?
C8 C7 N1 120.40(14) . . ?
C12 C7 N1 120.46(13) . . ?
C1 C6 C5 120.02(14) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C15 C16 C17 118.19(13) . . ?
C15 C16 C19 120.11(15) . . ?
C17 C16 C19 121.69(15) . . ?
C4 C5 C6 120.65(15) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C18 C17 C16 120.85(14) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C15 C14 C13 120.10(14) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 121.80(14) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C3 C4 C5 119.34(15) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C3 C2 120.89(15) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C11 C12 C7 120.74(16) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C3 C2 C1 119.83(14) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C17 C18 C13 120.61(14) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C7 C8 C9 119.39(17) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
O1 C19 C16 126.44(18) . . ?
O1 C19 H19 116.8 . . ?
C16 C19 H19 116.8 . . ?
C10 C9 C8 120.86(17) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 119.39(16) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 120.52(18) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?

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
C13 N1 C1 C6 122.28(15) . . . . ?
C7 N1 C1 C6 -48.38(19) . . . . ?
C13 N1 C1 C2 -58.35(19) . . . . ?
C7 N1 C1 C2 130.99(15) . . . . ?
C1 N1 C13 C14 -23.9(2) . . . . ?
C7 N1 C13 C14 146.52(14) . . . . ?
C1 N1 C13 C18 155.18(14) . . . . ?
C7 N1 C13 C18 -34.5(2) . . . . ?
C13 N1 C7 C8 138.91(15) . . . . ?
C1 N1 C7 C8 -50.5(2) . . . . ?
C13 N1 C7 C12 -43.3(2) . . . . ?
C1 N1 C7 C12 127.33(16) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
N1 C1 C6 C5 179.59(13) . . . . ?
C1 C6 C5 C4 0.5(2) . . . . ?
C15 C16 C17 C18 0.2(2) . . . . ?
C19 C16 C17 C18 178.94(15) . . . . ?
N1 C13 C14 C15 178.79(14) . . . . ?
C18 C13 C14 C15 -0.3(2) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C17 C16 C15 C14 -0.9(2) . . . . ?
C19 C16 C15 C14 -179.74(15) . . . . ?
C6 C5 C4 C3 -0.5(2) . . . . ?
C5 C4 C3 C2 0.0(2) . . . . ?
C8 C7 C12 C11 -0.1(2) . . . . ?
N1 C7 C12 C11 -177.91(15) . . . . ?
C4 C3 C2 C1 0.7(2) . . . . ?
C6 C1 C2 C3 -0.8(2) . . . . ?
N1 C1 C2 C3 179.84(13) . . . . ?
C16 C17 C18 C13 0.6(2) . . . . ?
C14 C13 C18 C17 -0.5(2) . . . . ?
N1 C13 C18 C17 -179.55(13) . . . . ?
C12 C7 C8 C9 -0.1(2) . . . . ?
N1 C7 C8 C9 177.79(14) . . . . ?
C15 C16 C19 O1 -177.76(18) . . . . ?
C17 C16 C19 O1 3.5(3) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C7 C12 C11 C10 0.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.026
_database_code_depnum_ccdc_archive 'CCDC 994493'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cao

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 N O3'
_chemical_formula_weight         361.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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                   14.6029(19)
_cell_length_b                   7.8062(10)
_cell_length_c                   17.686(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.7120(10)
_cell_angle_gamma                90.00
_cell_volume                     1997.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8292
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.11

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9766
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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  '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            13696
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3513
_reflns_number_gt                3057
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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)+(0.0767P)²+0.3195P] 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         3513
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
O3 O 0.93004(8) 0.65206(13) 0.87541(6) 0.0612(3) Uani 1 1 d . . .
O1 O 0.43300(8) -0.13352(17) 0.91154(7) 0.0764(4) Uani 1 1 d . . .
N1 N 0.71510(9) 0.10030(15) 0.75417(7) 0.0563(3) Uani 1 1 d . . .
O2 O 0.80498(10) -0.41917(19) 0.49071(8) 0.0894(4) Uani 1 1 d . . .
C6 C 0.64339(10) 0.03351(18) 0.79446(7) 0.0497(3) Uani 1 1 d . . .
C21 C 0.68883(10) -0.12031(18) 0.65776(8) 0.0522(3) Uani 1 1 d . . .
H21 H 0.6301 -0.1390 0.6710 0.063 Uiso 1 1 calc R . .
C14 C 0.76606(10) 0.24759(17) 0.78567(7) 0.0496(3) Uani 1 1 d . . .
C13 C 0.77355(11) 0.39083(18) 0.74104(8) 0.0551(4) Uani 1 1 d . . .
H13 H 0.7421 0.3944 0.6917 0.066 Uiso 1 1 calc R . .
C8 C 0.50582(10) -0.0870(2) 0.87445(8) 0.0556(4) Uani 1 1 d . . .
C9 C 0.80997(11) 0.24555(19) 0.86025(8) 0.0550(4) Uani 1 1 d . . .
H9 H 0.8040 0.1509 0.8912 0.066 Uiso 1 1 calc R . .
C10 C 0.86236(11) 0.38387(19) 0.88846(8) 0.0568(4) Uani 1 1 d . . .
H10 H 0.8910 0.3826 0.9387 0.068 Uiso 1 1 calc R . .
C23 C 0.84309(13) -0.2975(2) 0.52288(8) 0.0656(4) Uani 1 1 d . . .
H23 H 0.9009 -0.2684 0.5102 0.079 Uiso 1 1 calc R . .
C12 C 0.82730(10) 0.52947(18) 0.76882(8) 0.0531(3) Uani 1 1 d . . .
H12 H 0.8327 0.6246 0.7381 0.064 Uiso 1 1 calc R . .
C22 C 0.74496(9) 0.00775(17) 0.69528(7) 0.0479(3) Uani 1 1 d . . .
C4 C 0.58979(10) -0.1695(2) 0.88075(9) 0.0590(4) Uani 1 1 d . . .
H4 H 0.6008 -0.2650 0.9120 0.071 Uiso 1 1 calc R . .
C19 C 0.80663(10) -0.19162(19) 0.58000(7) 0.0518(3) Uani 1 1 d . . .
C17 C 0.83177(10) 0.03686(19) 0.67203(8) 0.0539(4) Uani 1 1 d . . .
H17 H 0.8698 0.1230 0.6950 0.065 Uiso 1 1 calc R . .
C11 C 0.87287(10) 0.52510(17) 0.84272(8) 0.0490(3) Uani 1 1 d . . .
C20 C 0.71926(10) -0.21864(19) 0.60172(8) 0.0531(3) Uani 1 1 d . . .
H20 H 0.6813 -0.3040 0.5780 0.064 Uiso 1 1 calc R . .
C7 C 0.55843(12) 0.1128(2) 0.78764(10) 0.0684(5) Uani 1 1 d . . .
H7 H 0.5474 0.2088 0.7566 0.082 Uiso 1 1 calc R . .
C18 C 0.86089(10) -0.0617(2) 0.61532(8) 0.0557(4) Uani 1 1 d . . .
H18 H 0.9185 -0.0404 0.6003 0.067 Uiso 1 1 calc R . .
C15 C 0.94266(11) 0.80135(19) 0.83147(9) 0.0588(4) Uani 1 1 d . . .
H15A H 0.8839 0.8581 0.8168 0.071 Uiso 1 1 calc R . .
H15B H 0.9683 0.7703 0.7855 0.071 Uiso 1 1 calc R . .
C5 C 0.65796(10) -0.1085(2) 0.83984(9) 0.0573(4) Uani 1 1 d . . .
H5 H 0.7144 -0.1652 0.8434 0.069 Uiso 1 1 calc R . .
C3 C 0.48966(12) 0.0510(2) 0.82644(11) 0.0732(5) Uani 1 1 d . . .
H3 H 0.4319 0.1031 0.8201 0.088 Uiso 1 1 calc R . .
C16 C 1.00751(13) 0.9180(2) 0.87977(11) 0.0756(5) Uani 1 1 d . . .
H16A H 0.9804 0.9515 0.9241 0.113 Uiso 1 1 calc R . .
H16B H 1.0190 1.0181 0.8509 0.113 Uiso 1 1 calc R . .
H16C H 1.0647 0.8594 0.8953 0.113 Uiso 1 1 calc R . .
C2 C 0.44550(13) -0.2686(2) 0.96507(10) 0.0745(5) Uani 1 1 d . . .
H2A H 0.4975 -0.2439 1.0037 0.089 Uiso 1 1 calc R . .
H2B H 0.4581 -0.3746 0.9398 0.089 Uiso 1 1 calc R . .
C1 C 0.35863(15) -0.2860(3) 1.00134(12) 0.0893(6) Uani 1 1 d . . .
H1A H 0.3458 -0.1795 1.0250 0.134 Uiso 1 1 calc R . .
H1B H 0.3666 -0.3747 1.0392 0.134 Uiso 1 1 calc R . .
H1C H 0.3080 -0.3148 0.9630 0.134 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C11 1.3726(17) . ?
O3 C15 1.4264(18) . ?
O1 C8 1.3713(17) . ?
O1 C2 1.412(2) . ?
N1 C22 1.3851(17) . ?
N1 C6 1.4410(17) . ?
N1 C14 1.4404(17) . ?
O2 C23 1.204(2) . ?
C6 C5 1.368(2) . ?
C6 C7 1.377(2) . ?
C21 C20 1.374(2) . ?
C21 C22 1.4020(19) . ?
C21 H21 0.9300 . ?
C14 C13 1.381(2) . ?
C14 C9 1.387(2) . ?
C13 C12 1.387(2) . ?
C13 H13 0.9300 . ?
C8 C4 1.376(2) . ?
C8 C3 1.372(2) . ?
C9 C10 1.378(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9300 . ?
C23 C19 1.460(2) . ?
C23 H23 0.9300 . ?
C12 C11 1.385(2) . ?
C12 H12 0.9300 . ?
C22 C17 1.4027(19) . ?
C4 C5 1.391(2) . ?
C4 H4 0.9300 . ?
C19 C18 1.384(2) . ?
C19 C20 1.397(2) . ?
C17 C18 1.376(2) . ?
C17 H17 0.9300 . ?
C20 H20 0.9300 . ?
C7 C3 1.377(2) . ?
C7 H7 0.9300 . ?
C18 H18 0.9300 . ?
C15 C16 1.496(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C2 C1 1.502(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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 O3 C15 118.44(11) . . ?
C8 O1 C2 118.65(13) . . ?
C22 N1 C6 120.40(11) . . ?
C22 N1 C14 120.58(11) . . ?
C6 N1 C14 118.00(10) . . ?
C5 C6 C7 118.87(13) . . ?
C5 C6 N1 121.14(13) . . ?
C7 C6 N1 120.00(13) . . ?
C20 C21 C22 120.99(13) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C13 C14 C9 119.38(13) . . ?
C13 C14 N1 120.10(12) . . ?
C9 C14 N1 120.50(13) . . ?
C14 C13 C12 120.90(13) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
O1 C8 C4 125.26(14) . . ?
O1 C8 C3 115.07(14) . . ?
C4 C8 C3 119.65(14) . . ?
C10 C9 C14 119.92(13) . . ?
C10 C9 H9 120.0 . . ?
C14 C9 H9 120.0 . . ?
C9 C10 C11 120.72(13) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
O2 C23 C19 125.80(17) . . ?
O2 C23 H23 117.1 . . ?
C19 C23 H23 117.1 . . ?
C13 C12 C11 119.48(13) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
N1 C22 C21 120.32(12) . . ?
N1 C22 C17 121.60(12) . . ?
C21 C22 C17 118.07(12) . . ?
C8 C4 C5 119.34(15) . . ?
C8 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C18 C19 C20 118.39(12) . . ?
C18 C19 C23 119.17(14) . . ?
C20 C19 C23 122.42(14) . . ?
C18 C17 C22 120.21(13) . . ?
C18 C17 H17 119.9 . . ?
C22 C17 H17 119.9 . . ?
O3 C11 C12 124.59(12) . . ?
O3 C11 C10 115.88(12) . . ?
C12 C11 C10 119.52(13) . . ?
C21 C20 C19 120.65(13) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C3 C7 C6 120.49(15) . . ?
C3 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C17 C18 C19 121.64(13) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
O3 C15 C16 107.73(13) . . ?
O3 C15 H15A 110.2 . . ?
C16 C15 H15A 110.2 . . ?
O3 C15 H15B 110.2 . . ?
C16 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?
C6 C5 C4 121.10(14) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C7 C3 C8 120.45(15) . . ?
C7 C3 H3 119.8 . . ?
C8 C3 H3 119.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C2 C1 108.24(16) . . ?
O1 C2 H2A 110.1 . . ?
C1 C2 H2A 110.1 . . ?
O1 C2 H2B 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 N1 C6 C5 67.45(19) . . . . ?
C14 N1 C6 C5 -101.09(16) . . . . ?
C22 N1 C6 C7 -112.53(17) . . . . ?
C14 N1 C6 C7 78.92(18) . . . . ?
C22 N1 C14 C13 64.59(19) . . . . ?
C6 N1 C14 C13 -126.88(15) . . . . ?
C22 N1 C14 C9 -113.75(15) . . . . ?
C6 N1 C14 C9 54.77(18) . . . . ?
C9 C14 C13 C12 2.6(2) . . . . ?
N1 C14 C13 C12 -175.77(13) . . . . ?
C2 O1 C8 C4 5.0(2) . . . . ?
C2 O1 C8 C3 -176.69(16) . . . . ?
C13 C14 C9 C10 -1.6(2) . . . . ?
N1 C14 C9 C10 176.71(13) . . . . ?
C14 C9 C10 C11 -0.9(2) . . . . ?
C14 C13 C12 C11 -1.0(2) . . . . ?
C6 N1 C22 C21 20.6(2) . . . . ?
C14 N1 C22 C21 -171.13(13) . . . . ?
C6 N1 C22 C17 -158.54(14) . . . . ?
C14 N1 C22 C17 9.7(2) . . . . ?
C20 C21 C22 N1 -176.89(13) . . . . ?
C20 C21 C22 C17 2.3(2) . . . . ?
O1 C8 C4 C5 -179.94(15) . . . . ?
C3 C8 C4 C5 1.8(2) . . . . ?
O2 C23 C19 C18 176.27(16) . . . . ?
O2 C23 C19 C20 -2.4(3) . . . . ?
N1 C22 C17 C18 177.50(13) . . . . ?
C21 C22 C17 C18 -1.7(2) . . . . ?
C15 O3 C11 C12 1.3(2) . . . . ?
C15 O3 C11 C10 -179.25(13) . . . . ?
C13 C12 C11 O3 177.88(13) . . . . ?
C13 C12 C11 C10 -1.5(2) . . . . ?
C9 C10 C11 O3 -176.99(13) . . . . ?
C9 C10 C11 C12 2.4(2) . . . . ?
C22 C21 C20 C19 -0.9(2) . . . . ?
C18 C19 C20 C21 -1.1(2) . . . . ?
C23 C19 C20 C21 177.54(14) . . . . ?
C5 C6 C7 C3 0.6(2) . . . . ?
N1 C6 C7 C3 -179.41(16) . . . . ?
C22 C17 C18 C19 -0.3(2) . . . . ?
C20 C19 C18 C17 1.8(2) . . . . ?
C23 C19 C18 C17 -176.95(14) . . . . ?
C11 O3 C15 C16 -179.90(12) . . . . ?
C7 C6 C5 C4 -2.2(2) . . . . ?
N1 C6 C5 C4 177.80(14) . . . . ?
C8 C4 C5 C6 1.0(2) . . . . ?
C6 C7 C3 C8 2.2(3) . . . . ?
O1 C8 C3 C7 178.16(17) . . . . ?
C4 C8 C3 C7 -3.4(3) . . . . ?
C8 O1 C2 C1 176.08(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.082
_database_code_depnum_ccdc_archive 'CCDC 990297'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H15 N3'
_chemical_formula_weight         321.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P21/c

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                   7.036(5)
_cell_length_b                   15.938(11)
_cell_length_c                   16.115(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.219(8)
_cell_angle_gamma                90.00
_cell_volume                     1800(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.071
_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      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12571
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3165
_reflns_number_gt                2352
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3165
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1460
_refine_ls_wR_factor_gt          0.1272
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.002
_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
N3 N 0.28382(19) 0.29577(8) 0.26678(7) 0.0535(4) Uani 1 1 d . . .
C17 C 0.26572(18) 0.45916(9) 0.47121(8) 0.0443(4) Uani 1 1 d . . .
C19 C 0.2903(2) 0.43599(9) 0.32434(9) 0.0491(4) Uani 1 1 d . . .
H19 H 0.3025 0.4581 0.2717 0.059 Uiso 1 1 calc R . .
C20 C 0.25155(19) 0.51094(10) 0.54342(9) 0.0483(4) Uani 1 1 d . . .
H20 H 0.2555 0.4816 0.5934 0.058 Uiso 1 1 calc R . .
C21 C 0.23345(19) 0.59521(9) 0.55124(9) 0.0488(4) Uani 1 1 d . . .
C16 C 0.2628(2) 0.37195(9) 0.48113(9) 0.0488(4) Uani 1 1 d . . .
H16 H 0.2564 0.3500 0.5343 0.059 Uiso 1 1 calc R . .
C14 C 0.28116(19) 0.34880(8) 0.33407(8) 0.0453(4) Uani 1 1 d . . .
C18 C 0.2819(2) 0.48934(9) 0.39023(9) 0.0491(4) Uani 1 1 d . . .
H18 H 0.2870 0.5469 0.3813 0.059 Uiso 1 1 calc R . .
C15 C 0.2690(2) 0.31762(9) 0.41532(9) 0.0495(4) Uani 1 1 d . . .
H15 H 0.2651 0.2600 0.4243 0.059 Uiso 1 1 calc R . .
C24 C 0.2217(2) 0.63211(10) 0.63167(10) 0.0537(4) Uani 1 1 d . . .
C6 C 0.2683(2) 0.32846(9) 0.18285(9) 0.0529(4) Uani 1 1 d . . .
N1 N 0.2126(2) 0.66166(10) 0.69563(10) 0.0712(4) Uani 1 1 d . . .
C22 C 0.2223(2) 0.65410(10) 0.48400(11) 0.0584(4) Uani 1 1 d . . .
C8 C 0.2962(2) 0.20625(10) 0.27690(9) 0.0535(4) Uani 1 1 d . . .
C9 C 0.1417(3) 0.15671(11) 0.25197(12) 0.0714(5) Uani 1 1 d . . .
H9 H 0.0290 0.1808 0.2284 0.086 Uiso 1 1 calc R . .
C1 C 0.0993(3) 0.36357(12) 0.14969(11) 0.0715(5) Uani 1 1 d . . .
H1 H -0.0058 0.3653 0.1807 0.086 Uiso 1 1 calc R . .
N2 N 0.2121(3) 0.70182(10) 0.43080(11) 0.0869(5) Uani 1 1 d . . .
C5 C 0.4225(3) 0.32480(11) 0.13652(10) 0.0657(5) Uani 1 1 d . . .
H5 H 0.5359 0.3003 0.1587 0.079 Uiso 1 1 calc R . .
C11 C 0.3193(3) 0.03437(11) 0.29745(11) 0.0768(6) Uani 1 1 d . . .
H11 H 0.3258 -0.0235 0.3049 0.092 Uiso 1 1 calc R . .
C4 C 0.4088(3) 0.35744(13) 0.05706(11) 0.0793(6) Uani 1 1 d . . .
H4 H 0.5131 0.3549 0.0256 0.095 Uiso 1 1 calc R . .
C13 C 0.4627(3) 0.16950(11) 0.31117(11) 0.0675(5) Uani 1 1 d . . .
H13 H 0.5684 0.2026 0.3273 0.081 Uiso 1 1 calc R . .
C12 C 0.4726(3) 0.08312(11) 0.32161(12) 0.0755(5) Uani 1 1 d . . .
H12 H 0.5846 0.0586 0.3452 0.091 Uiso 1 1 calc R . .
C2 C 0.0875(3) 0.39620(13) 0.06992(12) 0.0848(6) Uani 1 1 d . . .
H2 H -0.0262 0.4201 0.0473 0.102 Uiso 1 1 calc R . .
C10 C 0.1554(3) 0.07053(12) 0.26221(13) 0.0836(6) Uani 1 1 d . . .
H10 H 0.0514 0.0368 0.2448 0.100 Uiso 1 1 calc R . .
C3 C 0.2413(4) 0.39371(12) 0.02408(11) 0.0825(6) Uani 1 1 d . . .
H3 H 0.2328 0.4165 -0.0293 0.099 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C14 1.3763(19) . ?
N3 C8 1.438(2) . ?
N3 C6 1.444(2) . ?
C17 C16 1.400(2) . ?
C17 C18 1.405(2) . ?
C17 C20 1.437(2) . ?
C19 C18 1.366(2) . ?
C19 C14 1.401(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.356(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.430(2) . ?
C21 C24 1.433(2) . ?
C16 C15 1.373(2) . ?
C16 H16 0.9300 . ?
C14 C15 1.410(2) . ?
C18 H18 0.9300 . ?
C15 H15 0.9300 . ?
C24 N1 1.140(2) . ?
C6 C5 1.373(2) . ?
C6 C1 1.377(2) . ?
C22 N2 1.143(2) . ?
C8 C9 1.373(2) . ?
C8 C13 1.379(2) . ?
C9 C10 1.386(3) . ?
C9 H9 0.9300 . ?
C1 C2 1.382(3) . ?
C1 H1 0.9300 . ?
C5 C4 1.377(3) . ?
C5 H5 0.9300 . ?
C11 C12 1.357(3) . ?
C11 C10 1.366(3) . ?
C11 H11 0.9300 . ?
C4 C3 1.375(3) . ?
C4 H4 0.9300 . ?
C13 C12 1.388(3) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C2 C3 1.365(3) . ?
C2 H2 0.9300 . ?
C10 H10 0.9300 . ?
C3 H3 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
C14 N3 C8 121.68(12) . . ?
C14 N3 C6 120.73(13) . . ?
C8 N3 C6 117.56(11) . . ?
C16 C17 C18 116.71(12) . . ?
C16 C17 C20 118.35(13) . . ?
C18 C17 C20 124.95(14) . . ?
C18 C19 C14 121.66(13) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
C21 C20 C17 131.13(14) . . ?
C21 C20 H20 114.4 . . ?
C17 C20 H20 114.4 . . ?
C20 C21 C22 125.36(14) . . ?
C20 C21 C24 120.29(14) . . ?
C22 C21 C24 114.35(14) . . ?
C15 C16 C17 122.43(13) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
N3 C14 C19 121.13(13) . . ?
N3 C14 C15 121.43(13) . . ?
C19 C14 C15 117.44(13) . . ?
C19 C18 C17 121.46(14) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C16 C15 C14 120.25(14) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
N1 C24 C21 179.8(2) . . ?
C5 C6 C1 120.21(16) . . ?
C5 C6 N3 119.84(15) . . ?
C1 C6 N3 119.95(14) . . ?
N2 C22 C21 179.16(19) . . ?
C9 C8 C13 119.57(16) . . ?
C9 C8 N3 119.94(15) . . ?
C13 C8 N3 120.49(15) . . ?
C8 C9 C10 119.37(18) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C6 C1 C2 119.39(17) . . ?
C6 C1 H1 120.3 . . ?
C2 C1 H1 120.3 . . ?
C6 C5 C4 119.82(18) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C12 C11 C10 119.77(18) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C3 C4 C5 120.22(18) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C8 C13 C12 120.08(17) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C11 C12 C13 120.22(18) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C11 C10 C9 120.97(18) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C2 C3 C4 119.77(18) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?

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
C16 C17 C20 C21 -173.24(15) . . . . ?
C18 C17 C20 C21 6.6(2) . . . . ?
C17 C20 C21 C22 0.6(3) . . . . ?
C17 C20 C21 C24 179.88(13) . . . . ?
C18 C17 C16 C15 -2.1(2) . . . . ?
C20 C17 C16 C15 177.71(13) . . . . ?
C8 N3 C14 C19 172.87(14) . . . . ?
C6 N3 C14 C19 -9.0(2) . . . . ?
C8 N3 C14 C15 -7.2(2) . . . . ?
C6 N3 C14 C15 170.90(13) . . . . ?
C18 C19 C14 N3 177.96(13) . . . . ?
C18 C19 C14 C15 -2.0(2) . . . . ?
C14 C19 C18 C17 0.7(2) . . . . ?
C16 C17 C18 C19 1.3(2) . . . . ?
C20 C17 C18 C19 -178.47(13) . . . . ?
C17 C16 C15 C14 0.8(2) . . . . ?
N3 C14 C15 C16 -178.73(14) . . . . ?
C19 C14 C15 C16 1.2(2) . . . . ?
C20 C21 C24 N1 144(100) . . . . ?
C22 C21 C24 N1 -37(87) . . . . ?
C14 N3 C6 C5 111.08(16) . . . . ?
C8 N3 C6 C5 -70.76(18) . . . . ?
C14 N3 C6 C1 -68.56(19) . . . . ?
C8 N3 C6 C1 109.60(18) . . . . ?
C20 C21 C22 N2 152(14) . . . . ?
C24 C21 C22 N2 -27(14) . . . . ?
C14 N3 C8 C9 110.17(17) . . . . ?
C6 N3 C8 C9 -67.97(18) . . . . ?
C14 N3 C8 C13 -70.13(19) . . . . ?
C6 N3 C8 C13 111.72(17) . . . . ?
C13 C8 C9 C10 0.4(3) . . . . ?
N3 C8 C9 C10 -179.87(16) . . . . ?
C5 C6 C1 C2 -1.0(3) . . . . ?
N3 C6 C1 C2 178.66(16) . . . . ?
C1 C6 C5 C4 0.9(2) . . . . ?
N3 C6 C5 C4 -178.75(14) . . . . ?
C6 C5 C4 C3 0.1(3) . . . . ?
C9 C8 C13 C12 -1.1(2) . . . . ?
N3 C8 C13 C12 179.23(14) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C8 C13 C12 C11 0.6(3) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C12 C11 C10 C9 -1.1(3) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C5 C4 C3 C2 -0.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.039
_database_code_depnum_ccdc_archive 'CCDC 990298'
