# Electronic Supplementary Material (ESI) for ChemComm.
# 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_a01

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H23 N3 O'
_chemical_formula_sum            'C24 H23 N3 O'
_chemical_formula_weight         369.45

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           Orthorhombic
_symmetry_space_group_name_H-M   'p 21 21 21'
_symmetry_space_group_name_HALL  'P 2ac 2ab'

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                   7.5448(8)
_cell_length_b                   9.2205(10)
_cell_length_c                   28.088(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1954.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9825
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      27.11

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9884
_exptl_absorpt_correction_T_max  0.9907
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15269
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         26.99
_reflns_number_total             4036
_reflns_number_gt                3721
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_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 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)+(0.0560P)²+0.1760P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0051(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.4(13)
_refine_ls_number_reflns         4036
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
O1 O 0.40052(14) 0.44727(10) 0.09755(3) 0.0445(2) Uani 1 1 d . . .
N1 N 0.53824(18) 0.57449(13) 0.15510(4) 0.0444(3) Uani 1 1 d . . .
N2 N 0.43284(17) 1.03454(12) -0.02098(4) 0.0436(3) Uani 1 1 d . . .
N3 N 0.46403(18) 1.59167(13) -0.15912(4) 0.0464(3) Uani 1 1 d . . .
C1 C 0.4204(2) 0.35659(15) 0.13598(5) 0.0412(3) Uani 1 1 d . . .
C2 C 0.3653(2) 0.21531(18) 0.14037(6) 0.0545(4) Uani 1 1 d . . .
H2A H 0.3076 0.1666 0.1159 0.065 Uiso 1 1 calc R . .
C3 C 0.4009(3) 0.15053(18) 0.18345(6) 0.0591(4) Uani 1 1 d . . .
H3A H 0.3660 0.0550 0.1884 0.071 Uiso 1 1 calc R . .
C4 C 0.4877(3) 0.22414(18) 0.21980(6) 0.0568(4) Uani 1 1 d . . .
H4A H 0.5090 0.1768 0.2485 0.068 Uiso 1 1 calc R . .
C5 C 0.5430(2) 0.36569(17) 0.21440(5) 0.0532(4) Uani 1 1 d . . .
H5A H 0.6023 0.4140 0.2387 0.064 Uiso 1 1 calc R . .
C6 C 0.50646(19) 0.43380(15) 0.17110(5) 0.0412(3) Uani 1 1 d . . .
C7 C 0.47437(18) 0.57582(14) 0.11238(5) 0.0378(3) Uani 1 1 d . . .
C8 C 0.46690(18) 0.69596(14) 0.07885(5) 0.0362(3) Uani 1 1 d . . .
C9 C 0.3737(2) 0.68206(15) 0.03632(5) 0.0409(3) Uani 1 1 d . . .
H9A H 0.3164 0.5955 0.0291 0.049 Uiso 1 1 calc R . .
C10 C 0.3663(2) 0.79677(15) 0.00491(5) 0.0421(3) Uani 1 1 d . . .
H10A H 0.3031 0.7864 -0.0233 0.051 Uiso 1 1 calc R . .
C11 C 0.45111(18) 0.92748(15) 0.01435(5) 0.0372(3) Uani 1 1 d . . .
C12 C 0.5462(2) 0.93993(15) 0.05687(5) 0.0425(3) Uani 1 1 d . . .
H12A H 0.6058 1.0257 0.0637 0.051 Uiso 1 1 calc R . .
C13 C 0.5525(2) 0.82652(15) 0.08864(5) 0.0416(3) Uani 1 1 d . . .
H13A H 0.6146 0.8371 0.1170 0.050 Uiso 1 1 calc R . .
C14 C 0.4877(2) 1.16345(15) -0.01522(5) 0.0439(3) Uani 1 1 d . . .
H14A H 0.5404 1.1880 0.0136 0.053 Uiso 1 1 calc R . .
C15 C 0.4718(2) 1.27392(15) -0.05155(5) 0.0401(3) Uani 1 1 d . . .
C16 C 0.5448(2) 1.41164(15) -0.04467(5) 0.0424(3) Uani 1 1 d . . .
H16A H 0.5975 1.4332 -0.0156 0.051 Uiso 1 1 calc R . .
C17 C 0.54136(19) 1.51589(14) -0.07937(5) 0.0404(3) Uani 1 1 d . . .
H17A H 0.5923 1.6059 -0.0734 0.048 Uiso 1 1 calc R . .
C18 C 0.46212(18) 1.48910(14) -0.12381(5) 0.0376(3) Uani 1 1 d . . .
C19 C 0.3814(2) 1.35211(15) -0.13005(5) 0.0441(3) Uani 1 1 d . . .
H19A H 0.3227 1.3319 -0.1584 0.053 Uiso 1 1 calc R . .
C20 C 0.3881(2) 1.24832(15) -0.09513(5) 0.0444(3) Uani 1 1 d . . .
H20A H 0.3357 1.1586 -0.1006 0.053 Uiso 1 1 calc R . .
C21 C 0.3505(2) 1.58183(19) -0.20089(5) 0.0519(4) Uani 1 1 d . . .
H21A H 0.3131 1.6788 -0.2098 0.062 Uiso 1 1 calc R . .
H21B H 0.2451 1.5272 -0.1926 0.062 Uiso 1 1 calc R . .
C22 C 0.4367(3) 1.5112(3) -0.24338(7) 0.0878(7) Uani 1 1 d . . .
H22A H 0.3535 1.5069 -0.2692 0.132 Uiso 1 1 calc R . .
H22B H 0.4735 1.4148 -0.2351 0.132 Uiso 1 1 calc R . .
H22C H 0.5381 1.5670 -0.2529 0.132 Uiso 1 1 calc R . .
C23 C 0.5834(2) 1.71650(16) -0.15745(5) 0.0473(4) Uani 1 1 d . . .
H23A H 0.6221 1.7385 -0.1896 0.057 Uiso 1 1 calc R . .
H23B H 0.6876 1.6903 -0.1391 0.057 Uiso 1 1 calc R . .
C24 C 0.5032(3) 1.85111(17) -0.13609(6) 0.0594(4) Uani 1 1 d . . .
H24A H 0.5896 1.9275 -0.1360 0.089 Uiso 1 1 calc R . .
H24B H 0.4663 1.8313 -0.1040 0.089 Uiso 1 1 calc R . .
H24C H 0.4025 1.8804 -0.1547 0.089 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
O1 C1 1.3736(16) . ?
O1 C7 1.3744(16) . ?
N1 C7 1.2931(18) . ?
N1 C6 1.3938(18) . ?
N2 C14 1.2689(18) . ?
N2 C11 1.4065(17) . ?
N3 C18 1.3705(17) . ?
N3 C21 1.4556(18) . ?
N3 C23 1.4625(19) . ?
C1 C2 1.373(2) . ?
C1 C6 1.379(2) . ?
C2 C3 1.376(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.390(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.378(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.396(2) . ?
C5 H5A 0.9300 . ?
C7 C8 1.4550(18) . ?
C8 C9 1.3921(19) . ?
C8 C13 1.3935(19) . ?
C9 C10 1.3784(19) . ?
C9 H9A 0.9300 . ?
C10 C11 1.3899(19) . ?
C10 H10A 0.9300 . ?
C11 C12 1.3979(19) . ?
C12 C13 1.3756(19) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.4467(19) . ?
C14 H14A 0.9300 . ?
C15 C20 1.397(2) . ?
C15 C16 1.398(2) . ?
C16 C17 1.3693(19) . ?
C16 H16A 0.9300 . ?
C17 C18 1.4058(18) . ?
C17 H17A 0.9300 . ?
C18 C19 1.4130(19) . ?
C19 C20 1.371(2) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C21 C22 1.507(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.506(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C1 O1 C7 104.04(10) . . ?
C7 N1 C6 104.13(12) . . ?
C14 N2 C11 122.38(12) . . ?
C18 N3 C21 122.28(12) . . ?
C18 N3 C23 121.76(11) . . ?
C21 N3 C23 115.95(12) . . ?
C2 C1 O1 127.95(14) . . ?
C2 C1 C6 124.62(14) . . ?
O1 C1 C6 107.42(12) . . ?
C1 C2 C3 115.57(15) . . ?
C1 C2 H2A 122.2 . . ?
C3 C2 H2A 122.2 . . ?
C2 C3 C4 121.74(15) . . ?
C2 C3 H3A 119.1 . . ?
C4 C3 H3A 119.1 . . ?
C5 C4 C3 121.59(15) . . ?
C5 C4 H4A 119.2 . . ?
C3 C4 H4A 119.2 . . ?
C4 C5 C6 117.53(16) . . ?
C4 C5 H5A 121.2 . . ?
C6 C5 H5A 121.2 . . ?
C1 C6 N1 109.31(12) . . ?
C1 C6 C5 118.94(14) . . ?
N1 C6 C5 131.74(14) . . ?
N1 C7 O1 115.09(12) . . ?
N1 C7 C8 128.48(12) . . ?
O1 C7 C8 116.41(11) . . ?
C9 C8 C13 118.88(12) . . ?
C9 C8 C7 120.32(12) . . ?
C13 C8 C7 120.80(12) . . ?
C10 C9 C8 119.92(12) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C9 C10 C11 121.66(12) . . ?
C9 C10 H10A 119.2 . . ?
C11 C10 H10A 119.2 . . ?
C10 C11 C12 118.05(13) . . ?
C10 C11 N2 115.40(11) . . ?
C12 C11 N2 126.54(12) . . ?
C13 C12 C11 120.63(13) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C12 C13 C8 120.84(12) . . ?
C12 C13 H13A 119.6 . . ?
C8 C13 H13A 119.6 . . ?
N2 C14 C15 122.86(13) . . ?
N2 C14 H14A 118.6 . . ?
C15 C14 H14A 118.6 . . ?
C20 C15 C16 116.91(13) . . ?
C20 C15 C14 122.44(13) . . ?
C16 C15 C14 120.63(12) . . ?
C17 C16 C15 122.13(12) . . ?
C17 C16 H16A 118.9 . . ?
C15 C16 H16A 118.9 . . ?
C16 C17 C18 121.12(13) . . ?
C16 C17 H17A 119.4 . . ?
C18 C17 H17A 119.4 . . ?
N3 C18 C17 121.12(12) . . ?
N3 C18 C19 122.12(12) . . ?
C17 C18 C19 116.77(12) . . ?
C20 C19 C18 121.28(13) . . ?
C20 C19 H19A 119.4 . . ?
C18 C19 H19A 119.4 . . ?
C19 C20 C15 121.70(13) . . ?
C19 C20 H20A 119.2 . . ?
C15 C20 H20A 119.2 . . ?
N3 C21 C22 114.26(15) . . ?
N3 C21 H21A 108.7 . . ?
C22 C21 H21A 108.7 . . ?
N3 C21 H21B 108.7 . . ?
C22 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 C24 114.45(14) . . ?
N3 C23 H23A 108.6 . . ?
C24 C23 H23A 108.6 . . ?
N3 C23 H23B 108.6 . . ?
C24 C23 H23B 108.6 . . ?
H23A C23 H23B 107.6 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.028
_database_code_depnum_ccdc_archive 'CCDC 994632'
#######################################################################
#
#                 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 N2 O2'
_chemical_formula_sum            'C20 H14 N2 O2'
_chemical_formula_weight         314.33

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  '
_symmetry_space_group_name_HALL  '-P 2ybc'

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

_cell_length_a                   26.467(5)
_cell_length_b                   4.692(5)
_cell_length_c                   12.387(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 101.332(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1508.3(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2138
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.18

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_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    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9732
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  '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            10120
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         0.78
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2656
_reflns_number_gt                1918
_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)+(0.1000P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2656
_refine_ls_number_parameters     218
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1700
_refine_ls_wR_factor_gt          0.1506
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.147
_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
O1 O 0.66917(6) -0.4685(3) 0.77153(12) 0.0528(5) Uani 1 1 d U . .
N2 N 0.81366(6) 0.4528(4) 0.58704(13) 0.0399(5) Uani 1 1 d . . .
N1 N 0.62979(6) -0.4444(4) 0.59513(13) 0.0391(5) Uani 1 1 d U . .
O2 O 0.85211(7) 0.7324(4) 0.44008(12) 0.0685(6) Uani 1 1 d . . .
H2 H 0.8311 0.6330 0.4633 0.103 Uiso 1 1 calc R . .
C6 C 0.88021(8) 0.8017(4) 0.63408(16) 0.0394(5) Uani 1 1 d . . .
C9 C 0.77769(8) 0.1570(5) 0.72111(17) 0.0442(6) Uani 1 1 d . . .
H9 H 0.8013 0.2298 0.7802 0.053 Uiso 1 1 calc R . .
C8 C 0.77865(7) 0.2508(4) 0.61452(15) 0.0368(5) Uani 1 1 d . . .
C11 C 0.70631(8) -0.1519(4) 0.65266(16) 0.0370(5) Uani 1 1 d . . .
C15 C 0.62750(8) -0.6513(5) 0.75619(17) 0.0415(5) Uani 1 1 d U . .
C1 C 0.88327(9) 0.8601(5) 0.52493(18) 0.0476(6) Uani 1 1 d . . .
C20 C 0.60312(8) -0.6364(5) 0.64838(17) 0.0432(6) Uani 1 1 d . . .
C14 C 0.66810(8) -0.3568(4) 0.67233(16) 0.0390(5) Uani 1 1 d U . .
C13 C 0.74344(8) 0.1347(4) 0.52788(16) 0.0436(6) Uani 1 1 d . . .
H13 H 0.7442 0.1903 0.4561 0.052 Uiso 1 1 calc R . .
C12 C 0.70755(8) -0.0611(5) 0.54637(17) 0.0445(6) Uani 1 1 d . . .
H12 H 0.6838 -0.1336 0.4873 0.053 Uiso 1 1 calc R . .
C7 C 0.84368(8) 0.5963(4) 0.66078(17) 0.0408(5) Uani 1 1 d . . .
H7 H 0.8420 0.5677 0.7343 0.049 Uiso 1 1 calc R . .
C10 C 0.74235(8) -0.0407(4) 0.73948(17) 0.0435(6) Uani 1 1 d . . .
H10 H 0.7424 -0.1016 0.8110 0.052 Uiso 1 1 calc R . .
C4 C 0.94839(9) 1.1393(5) 0.6965(2) 0.0569(7) Uani 1 1 d . . .
H4 H 0.9702 1.2323 0.7537 0.068 Uiso 1 1 calc R . .
C5 C 0.91290(8) 0.9467(5) 0.71829(19) 0.0495(6) Uani 1 1 d . . .
H5 H 0.9105 0.9116 0.7910 0.059 Uiso 1 1 calc R . .
C16 C 0.61057(10) -0.8278(5) 0.8312(2) 0.0587(7) Uani 1 1 d . . .
H16 H 0.6274 -0.8376 0.9044 0.070 Uiso 1 1 calc R . .
C3 C 0.95125(10) 1.1933(6) 0.5886(2) 0.0634(7) Uani 1 1 d . . .
H3 H 0.9752 1.3243 0.5732 0.076 Uiso 1 1 calc R . .
C2 C 0.91939(10) 1.0574(6) 0.5033(2) 0.0639(7) Uani 1 1 d . . .
H2A H 0.9219 1.0969 0.4310 0.077 Uiso 1 1 calc R . .
C18 C 0.54273(10) -0.9727(6) 0.6837(3) 0.0685(8) Uani 1 1 d . . .
H18 H 0.5136 -1.0838 0.6601 0.082 Uiso 1 1 calc R . .
C19 C 0.55978(10) -0.7971(6) 0.6092(2) 0.0668(8) Uani 1 1 d . . .
H19 H 0.5429 -0.7874 0.5360 0.080 Uiso 1 1 calc R . .
C17 C 0.56743(10) -0.9881(6) 0.7910(2) 0.0646(8) Uani 1 1 d . . .
H17 H 0.5548 -1.1104 0.8385 0.078 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
O1 C14 1.331(2) . ?
O1 C15 1.381(3) . ?
N2 C7 1.278(3) . ?
N2 C8 1.413(3) . ?
N1 C14 1.315(2) . ?
N1 C20 1.388(3) . ?
O2 C1 1.343(3) . ?
O2 H2 0.8200 . ?
C6 C5 1.394(3) . ?
C6 C1 1.397(3) . ?
C6 C7 1.449(3) . ?
C9 C10 1.368(3) . ?
C9 C8 1.397(3) . ?
C9 H9 0.9300 . ?
C8 C13 1.387(3) . ?
C11 C12 1.390(3) . ?
C11 C10 1.391(3) . ?
C11 C14 1.450(3) . ?
C15 C20 1.366(3) . ?
C15 C16 1.383(3) . ?
C1 C2 1.394(3) . ?
C20 C19 1.379(3) . ?
C13 C12 1.373(3) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C7 H7 0.9300 . ?
C10 H10 0.9300 . ?
C4 C5 1.368(3) . ?
C4 C3 1.378(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C16 C17 1.376(4) . ?
C16 H16 0.9300 . ?
C3 C2 1.372(4) . ?
C3 H3 0.9300 . ?
C2 H2A 0.9300 . ?
C18 C17 1.364(4) . ?
C18 C19 1.377(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C17 H17 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 O1 C15 104.25(16) . . ?
C7 N2 C8 121.75(18) . . ?
C14 N1 C20 104.39(16) . . ?
C1 O2 H2 109.5 . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 C7 119.84(19) . . ?
C1 C6 C7 121.29(19) . . ?
C10 C9 C8 120.73(19) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C13 C8 C9 118.26(19) . . ?
C13 C8 N2 116.73(17) . . ?
C9 C8 N2 125.00(18) . . ?
C12 C11 C10 118.48(19) . . ?
C12 C11 C14 120.62(18) . . ?
C10 C11 C14 120.91(18) . . ?
C20 C15 O1 108.28(18) . . ?
C20 C15 C16 122.3(2) . . ?
O1 C15 C16 129.4(2) . . ?
O2 C1 C2 119.0(2) . . ?
O2 C1 C6 121.8(2) . . ?
C2 C1 C6 119.2(2) . . ?
C15 C20 C19 121.1(2) . . ?
C15 C20 N1 108.13(18) . . ?
C19 C20 N1 130.8(2) . . ?
N1 C14 O1 114.93(18) . . ?
N1 C14 C11 123.25(18) . . ?
O1 C14 C11 121.81(18) . . ?
C12 C13 C8 121.03(19) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
C13 C12 C11 120.60(19) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
N2 C7 C6 122.44(19) . . ?
N2 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C9 C10 C11 120.88(19) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.6(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C17 C16 C15 116.1(2) . . ?
C17 C16 H16 122.0 . . ?
C15 C16 H16 122.0 . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C17 C18 C19 121.8(3) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C20 116.8(2) . . ?
C18 C19 H19 121.6 . . ?
C20 C19 H19 121.6 . . ?
C18 C17 C16 121.9(2) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 994633'
#######################################################################
#
#                 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H23 N3 O2'
_chemical_formula_sum            'C24 H23 N3 O2'
_chemical_formula_weight         385.45

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

_cell_length_a                   7.516(5)
_cell_length_b                   9.490(5)
_cell_length_c                   27.807(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1983.4(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5252
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      25.31

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_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    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9754
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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  '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            14210
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3485
_reflns_number_gt                3157
_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)+(0.1000P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.0(12)
_refine_ls_number_reflns         3485
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   0.856
_refine_ls_restrained_S_all      0.856
_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
O1 O 0.09391(16) -0.54095(12) 1.09777(4) 0.0458(3) Uani 1 1 d . . .
N3 N 0.03052(19) 0.57263(15) 0.84141(5) 0.0465(3) Uani 1 1 d . . .
N2 N 0.05021(17) 0.03623(14) 0.98167(5) 0.0427(3) Uani 1 1 d . . .
O2 O 0.17545(19) 0.11498(13) 0.89919(5) 0.0613(4) Uani 1 1 d . . .
H2 H 0.1431 0.0591 0.9199 0.092 Uiso 1 1 calc R . .
C18 C 0.0296(2) 0.47458(16) 0.87733(6) 0.0394(4) Uani 1 1 d . . .
C8 C 0.0253(2) -0.29918(16) 1.08010(5) 0.0383(4) Uani 1 1 d . . .
N1 N -0.03480(19) -0.41859(14) 1.15752(5) 0.0453(3) Uani 1 1 d . . .
C15 C 0.0119(2) 0.26828(17) 0.95168(6) 0.0398(4) Uani 1 1 d . . .
C16 C -0.0599(2) 0.40438(17) 0.95701(6) 0.0439(4) Uani 1 1 d . . .
H16 H -0.1144 0.4272 0.9860 0.053 Uiso 1 1 calc R . .
C7 C 0.0235(2) -0.41632(16) 1.11396(6) 0.0397(4) Uani 1 1 d . . .
C12 C 0.1177(2) -0.19807(17) 1.00522(6) 0.0431(4) Uani 1 1 d . . .
H12 H 0.1778 -0.2072 0.9762 0.052 Uiso 1 1 calc R . .
C11 C 0.03436(19) -0.07111(17) 1.01618(5) 0.0390(4) Uani 1 1 d . . .
C14 C -0.0084(2) 0.16339(17) 0.98761(6) 0.0429(4) Uani 1 1 d . . .
H14 H -0.0653 0.1866 1.0162 0.052 Uiso 1 1 calc R . .
C2 C 0.0785(2) -0.63039(18) 1.13623(6) 0.0423(4) Uani 1 1 d . . .
C17 C -0.0538(2) 0.50359(16) 0.92221(6) 0.0424(4) Uani 1 1 d . . .
H17 H -0.1044 0.5916 0.9276 0.051 Uiso 1 1 calc R . .
C13 C 0.1130(2) -0.31035(17) 1.03643(6) 0.0425(4) Uani 1 1 d . . .
H13 H 0.1690 -0.3943 1.0282 0.051 Uiso 1 1 calc R . .
C1 C -0.0018(2) -0.55587(18) 1.17322(5) 0.0424(4) Uani 1 1 d . . .
C9 C -0.0597(2) -0.17241(17) 1.09125(6) 0.0436(4) Uani 1 1 d . . .
H9 H -0.1197 -0.1636 1.1204 0.052 Uiso 1 1 calc R . .
C20 C 0.1006(2) 0.24172(16) 0.90750(6) 0.0412(4) Uani 1 1 d . . .
C19 C 0.1114(2) 0.34213(17) 0.87199(6) 0.0430(4) Uani 1 1 d . . .
H19 H 0.1739 0.3222 0.8439 0.052 Uiso 1 1 calc R . .
C21 C -0.0907(3) 0.69415(18) 0.84177(6) 0.0511(4) Uani 1 1 d . . .
H21A H -0.1967 0.6693 0.8597 0.061 Uiso 1 1 calc R . .
H21B H -0.1267 0.7144 0.8090 0.061 Uiso 1 1 calc R . .
C10 C -0.0562(2) -0.06061(18) 1.05995(6) 0.0448(4) Uani 1 1 d . . .
H10 H -0.1144 0.0227 1.0679 0.054 Uiso 1 1 calc R . .
C3 C 0.1297(3) -0.7686(2) 1.13937(7) 0.0572(5) Uani 1 1 d . . .
H3 H 0.1823 -0.8160 1.1138 0.069 Uiso 1 1 calc R . .
C23 C 0.1436(2) 0.5594(2) 0.79914(6) 0.0546(4) Uani 1 1 d . . .
H23A H 0.2499 0.5075 0.8080 0.066 Uiso 1 1 calc R . .
H23B H 0.1803 0.6528 0.7891 0.066 Uiso 1 1 calc R . .
C6 C -0.0338(3) -0.6228(2) 1.21674(7) 0.0572(5) Uani 1 1 d . . .
H6 H -0.0880 -0.5759 1.2422 0.069 Uiso 1 1 calc R . .
C5 C 0.0180(3) -0.7621(2) 1.22082(7) 0.0606(5) Uani 1 1 d . . .
H5 H -0.0014 -0.8094 1.2496 0.073 Uiso 1 1 calc R . .
C22 C -0.0113(3) 0.82481(19) 0.86329(7) 0.0610(5) Uani 1 1 d . . .
H22A H 0.0126 0.8091 0.8968 0.091 Uiso 1 1 calc R . .
H22B H -0.0934 0.9017 0.8599 0.091 Uiso 1 1 calc R . .
H22C H 0.0976 0.8472 0.8470 0.091 Uiso 1 1 calc R . .
C4 C 0.0980(3) -0.8326(2) 1.18310(7) 0.0611(5) Uani 1 1 d . . .
H4 H 0.1315 -0.9261 1.1873 0.073 Uiso 1 1 calc R . .
C24 C 0.0565(4) 0.4865(3) 0.75728(8) 0.0920(8) Uani 1 1 d . . .
H24A H 0.0208 0.3934 0.7667 0.138 Uiso 1 1 calc R . .
H24B H 0.1392 0.4805 0.7311 0.138 Uiso 1 1 calc R . .
H24C H -0.0462 0.5392 0.7473 0.138 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
O1 C2 1.370(2) . ?
O1 C7 1.372(2) . ?
N3 C18 1.365(2) . ?
N3 C23 1.456(2) . ?
N3 C21 1.470(2) . ?
N2 C14 1.295(2) . ?
N2 C11 1.405(2) . ?
O2 C20 1.348(2) . ?
O2 H2 0.8200 . ?
C18 C19 1.407(2) . ?
C18 C17 1.423(2) . ?
C8 C13 1.386(2) . ?
C8 C9 1.397(2) . ?
C8 C7 1.457(2) . ?
N1 C7 1.288(2) . ?
N1 C1 1.396(2) . ?
C15 C16 1.408(2) . ?
C15 C14 1.419(2) . ?
C15 C20 1.420(2) . ?
C16 C17 1.351(2) . ?
C16 H16 0.9300 . ?
C12 C13 1.375(2) . ?
C12 C11 1.392(2) . ?
C12 H12 0.9300 . ?
C11 C10 1.398(2) . ?
C14 H14 0.9300 . ?
C2 C3 1.370(3) . ?
C2 C1 1.387(2) . ?
C17 H17 0.9300 . ?
C13 H13 0.9300 . ?
C1 C6 1.388(2) . ?
C9 C10 1.373(2) . ?
C9 H9 0.9300 . ?
C20 C19 1.375(2) . ?
C19 H19 0.9300 . ?
C21 C22 1.501(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C10 H10 0.9300 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9300 . ?
C23 C24 1.504(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C6 C5 1.383(3) . ?
C6 H6 0.9300 . ?
C5 C4 1.382(3) . ?
C5 H5 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C4 H4 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C2 O1 C7 104.20(12) . . ?
C18 N3 C23 122.33(14) . . ?
C18 N3 C21 121.79(13) . . ?
C23 N3 C21 115.79(14) . . ?
C14 N2 C11 124.04(14) . . ?
C20 O2 H2 109.5 . . ?
N3 C18 C19 121.97(14) . . ?
N3 C18 C17 120.79(14) . . ?
C19 C18 C17 117.24(14) . . ?
C13 C8 C9 118.54(15) . . ?
C13 C8 C7 120.83(14) . . ?
C9 C8 C7 120.63(14) . . ?
C7 N1 C1 104.43(13) . . ?
C16 C15 C14 121.90(14) . . ?
C16 C15 C20 115.72(14) . . ?
C14 C15 C20 122.36(15) . . ?
C17 C16 C15 123.43(14) . . ?
C17 C16 H16 118.3 . . ?
C15 C16 H16 118.3 . . ?
N1 C7 O1 115.18(14) . . ?
N1 C7 C8 128.58(14) . . ?
O1 C7 C8 116.25(13) . . ?
C13 C12 C11 121.43(14) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C11 C10 118.12(15) . . ?
C12 C11 N2 116.11(14) . . ?
C10 C11 N2 125.76(15) . . ?
N2 C14 C15 121.83(15) . . ?
N2 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C3 C2 O1 128.25(16) . . ?
C3 C2 C1 124.30(17) . . ?
O1 C2 C1 107.45(14) . . ?
C16 C17 C18 120.55(14) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C12 C13 C8 120.41(15) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C2 C1 C6 119.26(17) . . ?
C2 C1 N1 108.73(14) . . ?
C6 C1 N1 132.01(16) . . ?
C10 C9 C8 121.07(15) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
O2 C20 C19 118.08(14) . . ?
O2 C20 C15 120.18(15) . . ?
C19 C20 C15 121.74(14) . . ?
C20 C19 C18 121.17(14) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
N3 C21 C22 113.86(16) . . ?
N3 C21 H21A 108.8 . . ?
C22 C21 H21A 108.8 . . ?
N3 C21 H21B 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C9 C10 C11 120.42(16) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C2 C3 C4 115.41(18) . . ?
C2 C3 H3 122.3 . . ?
C4 C3 H3 122.3 . . ?
N3 C23 C24 114.23(17) . . ?
N3 C23 H23A 108.7 . . ?
C24 C23 H23A 108.7 . . ?
N3 C23 H23B 108.7 . . ?
C24 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C5 C6 C1 117.42(19) . . ?
C5 C6 H6 121.3 . . ?
C1 C6 H6 121.3 . . ?
C4 C5 C6 121.54(18) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C3 C4 C5 122.08(18) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C23 N3 C18 C19 -12.2(2) . . . . ?
C21 N3 C18 C19 164.12(14) . . . . ?
C23 N3 C18 C17 167.19(16) . . . . ?
C21 N3 C18 C17 -16.5(2) . . . . ?
C14 C15 C16 C17 -175.27(16) . . . . ?
C20 C15 C16 C17 2.8(2) . . . . ?
C1 N1 C7 O1 0.28(18) . . . . ?
C1 N1 C7 C8 -179.27(15) . . . . ?
C2 O1 C7 N1 -0.62(18) . . . . ?
C2 O1 C7 C8 178.99(13) . . . . ?
C13 C8 C7 N1 172.08(16) . . . . ?
C9 C8 C7 N1 -7.2(3) . . . . ?
C13 C8 C7 O1 -7.5(2) . . . . ?
C9 C8 C7 O1 173.27(14) . . . . ?
C13 C12 C11 C10 -0.5(2) . . . . ?
C13 C12 C11 N2 179.30(14) . . . . ?
C14 N2 C11 C12 -174.99(14) . . . . ?
C14 N2 C11 C10 4.8(2) . . . . ?
C11 N2 C14 C15 179.64(14) . . . . ?
C16 C15 C14 N2 176.57(15) . . . . ?
C20 C15 C14 N2 -1.4(2) . . . . ?
C7 O1 C2 C3 -179.66(18) . . . . ?
C7 O1 C2 C1 0.68(17) . . . . ?
C15 C16 C17 C18 -0.6(3) . . . . ?
N3 C18 C17 C16 177.60(16) . . . . ?
C19 C18 C17 C16 -3.0(2) . . . . ?
C11 C12 C13 C8 -0.4(2) . . . . ?
C9 C8 C13 C12 0.9(2) . . . . ?
C7 C8 C13 C12 -178.41(14) . . . . ?
C3 C2 C1 C6 0.1(3) . . . . ?
O1 C2 C1 C6 179.81(15) . . . . ?
C3 C2 C1 N1 179.77(16) . . . . ?
O1 C2 C1 N1 -0.55(18) . . . . ?
C7 N1 C1 C2 0.17(18) . . . . ?
C7 N1 C1 C6 179.75(19) . . . . ?
C13 C8 C9 C10 -0.4(2) . . . . ?
C7 C8 C9 C10 178.88(15) . . . . ?
C16 C15 C20 O2 179.30(15) . . . . ?
C14 C15 C20 O2 -2.6(3) . . . . ?
C16 C15 C20 C19 -1.4(2) . . . . ?
C14 C15 C20 C19 176.62(14) . . . . ?
O2 C20 C19 C18 177.18(15) . . . . ?
C15 C20 C19 C18 -2.1(2) . . . . ?
N3 C18 C19 C20 -176.29(15) . . . . ?
C17 C18 C19 C20 4.3(2) . . . . ?
C18 N3 C21 C22 94.4(2) . . . . ?
C23 N3 C21 C22 -88.98(19) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C12 C11 C10 C9 0.9(2) . . . . ?
N2 C11 C10 C9 -178.80(15) . . . . ?
O1 C2 C3 C4 179.72(17) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C18 N3 C23 C24 92.3(2) . . . . ?
C21 N3 C23 C24 -84.2(2) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
N1 C1 C6 C5 -179.20(18) . . . . ?
C1 C6 C5 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C6 C5 C4 C3 -0.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 994634'
