# 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 N2 O'
_chemical_formula_weight         340.42

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           ?
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   9.7827(8)
_cell_length_b                   10.0303(4)
_cell_length_c                   10.3019(4)
_cell_angle_alpha                110.382(2)
_cell_angle_beta                 101.227(2)
_cell_angle_gamma                102.845(2)
_cell_volume                     881.95(9)
_cell_formula_units_Z            2
_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          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.992
_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_reflns_number            8516
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.74
_reflns_number_total             3323
_reflns_number_gt                2812
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0798P)²+0.1227P] 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         3323
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1285
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 1.16337(12) 0.24195(12) -0.16828(11) 0.0561(3) Uani 1 1 d . . .
N1 N 1.10232(11) 0.32872(12) 0.04736(12) 0.0390(3) Uani 1 1 d . . .
N2 N 0.69803(13) -0.08827(13) -0.11478(13) 0.0455(3) Uani 1 1 d . . .
C1 C 1.5576(2) 0.89535(19) 0.3331(2) 0.0670(5) Uani 1 1 d . . .
H1A H 1.5201 0.9719 0.3198 0.100 Uiso 1 1 calc R . .
H1B H 1.6376 0.8901 0.2924 0.100 Uiso 1 1 calc R . .
H1C H 1.5916 0.9189 0.4348 0.100 Uiso 1 1 calc R . .
C2 C 1.43769(15) 0.74680(16) 0.25831(16) 0.0464(3) Uani 1 1 d . . .
C3 C 1.46774(15) 0.61570(16) 0.18725(15) 0.0462(3) Uani 1 1 d . . .
H3 H 1.5633 0.6207 0.1849 0.055 Uiso 1 1 calc R . .
C4 C 1.35915(14) 0.47867(16) 0.12024(15) 0.0428(3) Uani 1 1 d . . .
H4 H 1.3821 0.3920 0.0760 0.051 Uiso 1 1 calc R . .
C5 C 1.21533(14) 0.47038(15) 0.11900(14) 0.0383(3) Uani 1 1 d . . .
C6 C 1.08456(14) 0.22544(15) -0.09309(14) 0.0400(3) Uani 1 1 d . . .
C7 C 0.95133(14) 0.09930(14) -0.12773(14) 0.0372(3) Uani 1 1 d . . .
C8 C 0.87514(14) -0.03897(15) -0.24931(14) 0.0394(3) Uani 1 1 d . . .
C9 C 0.74787(15) -0.12822(15) -0.23505(15) 0.0423(3) Uani 1 1 d . . .
C10 C 0.66739(17) -0.26750(17) -0.35123(17) 0.0531(4) Uani 1 1 d . . .
H10 H 0.5846 -0.3280 -0.3441 0.064 Uiso 1 1 calc R . .
C11 C 0.70911(19) -0.31496(19) -0.47403(17) 0.0593(4) Uani 1 1 d . . .
H11 H 0.6549 -0.4077 -0.5492 0.071 Uiso 1 1 calc R . .
C12 C 1.29344(16) 0.73554(16) 0.25680(17) 0.0489(3) Uani 1 1 d . . .
H12 H 1.2710 0.8216 0.3043 0.059 Uiso 1 1 calc R . .
C13 C 1.18246(15) 0.60004(16) 0.18670(16) 0.0459(3) Uani 1 1 d . . .
H13 H 1.0861 0.5957 0.1848 0.055 Uiso 1 1 calc R . .
C14 C 0.91483(17) -0.09041(17) -0.37790(15) 0.0481(3) Uani 1 1 d . . .
H14 H 0.9971 -0.0322 -0.3879 0.058 Uiso 1 1 calc R . .
C15 C 0.83195(19) -0.22628(19) -0.48816(16) 0.0573(4) Uani 1 1 d . . .
H15 H 0.8580 -0.2596 -0.5732 0.069 Uiso 1 1 calc R . .
C16 C 0.77201(14) 0.04152(15) -0.00591(15) 0.0396(3) Uani 1 1 d . . .
C17 C 0.73741(15) 0.09400(16) 0.13536(15) 0.0454(3) Uani 1 1 d . . .
H17A H 0.7803 0.0483 0.1947 0.055 Uiso 1 1 calc R . .
H17B H 0.6318 0.0589 0.1161 0.055 Uiso 1 1 calc R . .
C18 C 0.79333(15) 0.26624(16) 0.22288(14) 0.0424(3) Uani 1 1 d . . .
C19 C 0.94468(14) 0.33987(15) 0.21663(14) 0.0414(3) Uani 1 1 d . . .
H19 H 1.0083 0.4264 0.2945 0.050 Uiso 1 1 calc R . .
C20 C 0.98545(13) 0.27974(14) 0.09917(14) 0.0365(3) Uani 1 1 d . . .
C21 C 0.89741(14) 0.13567(14) -0.01309(14) 0.0370(3) Uani 1 1 d . . .
C22 C 0.68823(17) 0.33530(19) 0.15731(17) 0.0548(4) Uani 1 1 d . . .
H22A H 0.7258 0.4425 0.2069 0.082 Uiso 1 1 calc R . .
H22B H 0.5931 0.3002 0.1678 0.082 Uiso 1 1 calc R . .
H22C H 0.6802 0.3063 0.0563 0.082 Uiso 1 1 calc R . .
C23 C 0.79572(18) 0.30115(19) 0.38039(16) 0.0553(4) Uani 1 1 d . . .
H23A H 0.8588 0.2553 0.4204 0.083 Uiso 1 1 calc R . .
H23B H 0.6981 0.2624 0.3837 0.083 Uiso 1 1 calc R . .
H23C H 0.8318 0.4077 0.4359 0.083 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 C6 1.2193(16) . ?
N1 C6 1.4053(17) . ?
N1 C20 1.4156(16) . ?
N1 C5 1.4281(17) . ?
N2 C16 1.3131(18) . ?
N2 C9 1.3819(18) . ?
C1 C2 1.503(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C12 1.387(2) . ?
C2 C3 1.392(2) . ?
C3 C4 1.378(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3881(18) . ?
C4 H4 0.9300 . ?
C5 C13 1.3866(19) . ?
C6 C7 1.4827(18) . ?
C7 C21 1.3543(18) . ?
C7 C8 1.4194(18) . ?
C8 C14 1.4089(19) . ?
C8 C9 1.428(2) . ?
C9 C10 1.408(2) . ?
C10 C11 1.364(2) . ?
C10 H10 0.9300 . ?
C11 C15 1.393(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.370(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.4040(19) . ?
C16 C17 1.4990(19) . ?
C17 C18 1.549(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.5251(19) . ?
C18 C23 1.5304(19) . ?
C18 C22 1.538(2) . ?
C19 C20 1.3317(18) . ?
C19 H19 0.9300 . ?
C20 C21 1.4361(18) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C6 N1 C20 110.79(10) . . ?
C6 N1 C5 123.36(11) . . ?
C20 N1 C5 125.53(11) . . ?
C16 N2 C9 117.88(12) . . ?
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 . . ?
C12 C2 C3 117.66(13) . . ?
C12 C2 C1 121.34(14) . . ?
C3 C2 C1 120.99(14) . . ?
C4 C3 C2 121.48(13) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.79(13) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C13 C5 C4 119.66(13) . . ?
C13 C5 N1 120.53(12) . . ?
C4 C5 N1 119.81(12) . . ?
O1 C6 N1 125.47(13) . . ?
O1 C6 C7 128.96(13) . . ?
N1 C6 C7 105.55(10) . . ?
C21 C7 C8 118.66(12) . . ?
C21 C7 C6 107.11(11) . . ?
C8 C7 C6 134.22(12) . . ?
C14 C8 C7 125.35(13) . . ?
C14 C8 C9 119.81(13) . . ?
C7 C8 C9 114.83(12) . . ?
N2 C9 C10 117.35(13) . . ?
N2 C9 C8 124.72(12) . . ?
C10 C9 C8 117.93(13) . . ?
C11 C10 C9 120.96(15) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C15 120.80(15) . . ?
C10 C11 H11 119.6 . . ?
C15 C11 H11 119.6 . . ?
C13 C12 C2 121.72(13) . . ?
C13 C12 H12 119.1 . . ?
C2 C12 H12 119.1 . . ?
C12 C13 C5 119.65(13) . . ?
C12 C13 H13 120.2 . . ?
C5 C13 H13 120.2 . . ?
C15 C14 C8 119.88(15) . . ?
C15 C14 H14 120.1 . . ?
C8 C14 H14 120.1 . . ?
C14 C15 C11 120.60(14) . . ?
C14 C15 H15 119.7 . . ?
C11 C15 H15 119.7 . . ?
N2 C16 C21 120.46(13) . . ?
N2 C16 C17 123.59(12) . . ?
C21 C16 C17 115.80(12) . . ?
C16 C17 C18 114.58(11) . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
C18 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C23 110.24(12) . . ?
C19 C18 C22 106.23(12) . . ?
C23 C18 C22 109.41(12) . . ?
C19 C18 C17 113.00(11) . . ?
C23 C18 C17 108.85(12) . . ?
C22 C18 C17 109.04(12) . . ?
C20 C19 C18 119.74(12) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 N1 134.49(12) . . ?
C19 C20 C21 120.65(12) . . ?
N1 C20 C21 104.79(10) . . ?
C7 C21 C16 123.43(12) . . ?
C7 C21 C20 111.66(12) . . ?
C16 C21 C20 124.91(12) . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.74
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.090
_database_code_depnum_ccdc_archive 'CCDC 972997'
#######################################################################
#
#                 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 N3 O3'
_chemical_formula_weight         371.39

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           ?
_symmetry_space_group_name_H-M   'P 21/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                   10.7669(3)
_cell_length_b                   9.7880(3)
_cell_length_c                   17.8714(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.3920(10)
_cell_angle_gamma                90.00
_cell_volume                     1797.30(10)
_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          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   empirical

_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.991
_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_reflns_number            26280
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         28.03
_reflns_number_total             4320
_reflns_number_gt                3148
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1424P)²+0.8333P] 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         4320
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1667
_refine_ls_wR_factor_gt          0.1386
_refine_ls_goodness_of_fit_ref   0.717
_refine_ls_restrained_S_all      0.717
_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 0.62166(16) 0.35658(16) 0.31267(10) 0.0766(5) Uani 1 1 d . . .
N6 N 1.10884(13) 0.24672(14) 0.01000(8) 0.0454(3) Uani 1 1 d . . .
O3 O 1.08955(13) 0.66050(13) 0.19314(8) 0.0563(3) Uani 1 1 d . . .
N1 N 0.91612(13) 0.50658(13) 0.15888(8) 0.0422(3) Uani 1 1 d . . .
O5 O 0.52583(17) 0.53804(18) 0.33342(11) 0.0829(5) Uani 1 1 d . . .
C30 C 0.88591(15) 0.38554(15) 0.11350(9) 0.0388(3) Uani 1 1 d . . .
C1 C 1.43096(18) 0.3982(2) 0.05115(12) 0.0590(5) Uani 1 1 d . . .
H1 H 1.5076 0.3812 0.0388 0.071 Uiso 1 1 calc R . .
C2 C 1.32635(18) 0.31405(19) 0.02210(12) 0.0541(4) Uani 1 1 d . . .
H2 H 1.3321 0.2412 -0.0101 0.065 Uiso 1 1 calc R . .
C3 C 1.20993(16) 0.33692(16) 0.04065(9) 0.0435(4) Uani 1 1 d . . .
C4 C 1.20463(15) 0.44990(16) 0.09056(9) 0.0403(3) Uani 1 1 d . . .
C5 C 1.08715(15) 0.46173(15) 0.11004(9) 0.0389(3) Uani 1 1 d . . .
C32 C 1.03864(16) 0.55843(15) 0.15910(9) 0.0418(3) Uani 1 1 d . . .
C7 C 0.83373(15) 0.57122(16) 0.19707(9) 0.0405(3) Uani 1 1 d . . .
C8 C 0.77005(15) 0.49441(16) 0.23964(9) 0.0415(4) Uani 1 1 d . . .
H8 H 0.7844 0.4010 0.2467 0.050 Uiso 1 1 calc R . .
C9 C 0.68463(16) 0.56171(17) 0.27112(9) 0.0437(4) Uani 1 1 d . . .
N7 N 0.60564(15) 0.47978(17) 0.30894(9) 0.0542(4) Uani 1 1 d . . .
C11 C 0.66505(19) 0.70056(18) 0.26554(11) 0.0532(4) Uani 1 1 d . . .
H11 H 0.6080 0.7428 0.2884 0.064 Uiso 1 1 calc R . .
C12 C 0.7323(2) 0.77523(19) 0.22509(12) 0.0596(5) Uani 1 1 d . . .
H12 H 0.7218 0.8695 0.2212 0.072 Uiso 1 1 calc R . .
C13 C 0.81524(19) 0.71154(17) 0.19013(11) 0.0517(4) Uani 1 1 d . . .
H13 H 0.8587 0.7627 0.1619 0.062 Uiso 1 1 calc R . .
C14 C 0.99337(15) 0.36631(15) 0.08255(9) 0.0385(3) Uani 1 1 d . . .
C15 C 1.00234(15) 0.26145(15) 0.03074(9) 0.0407(3) Uani 1 1 d . . .
C16 C 0.88150(16) 0.17715(16) -0.00104(10) 0.0442(4) Uani 1 1 d . . .
H16A H 0.9059 0.0873 -0.0148 0.053 Uiso 1 1 calc R . .
H16B H 0.8271 0.2196 -0.0486 0.053 Uiso 1 1 calc R . .
C17 C 0.80160(16) 0.16067(16) 0.05742(9) 0.0439(4) Uani 1 1 d . . .
C18 C 0.79182(16) 0.29227(16) 0.10088(10) 0.0438(4) Uani 1 1 d . . .
H18 H 0.7201 0.3075 0.1186 0.053 Uiso 1 1 calc R . .
C19 C 0.66485(19) 0.1106(2) 0.01304(12) 0.0628(5) Uani 1 1 d . . .
H19A H 0.6707 0.0249 -0.0118 0.094 Uiso 1 1 calc R . .
H19B H 0.6228 0.1766 -0.0261 0.094 Uiso 1 1 calc R . .
H19C H 0.6151 0.0990 0.0491 0.094 Uiso 1 1 calc R . .
C20 C 0.8697(2) 0.05540(19) 0.11904(12) 0.0647(5) Uani 1 1 d . . .
H20A H 0.8240 0.0473 0.1574 0.097 Uiso 1 1 calc R . .
H20B H 0.9575 0.0842 0.1442 0.097 Uiso 1 1 calc R . .
H20C H 0.8704 -0.0315 0.0942 0.097 Uiso 1 1 calc R . .
C21 C 1.42485(18) 0.5095(2) 0.09906(11) 0.0567(5) Uani 1 1 d . . .
H21 H 1.4968 0.5662 0.1176 0.068 Uiso 1 1 calc R . .
C22 C 1.31383(16) 0.53553(18) 0.11885(10) 0.0484(4) Uani 1 1 d . . .
H22 H 1.3105 0.6095 0.1509 0.058 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 N7 1.217(2) . ?
N6 C15 1.314(2) . ?
N6 C3 1.381(2) . ?
O3 C32 1.2122(19) . ?
N1 C32 1.412(2) . ?
N1 C30 1.4176(19) . ?
N1 C7 1.4195(19) . ?
O5 N7 1.216(2) . ?
C30 C18 1.332(2) . ?
C30 C14 1.436(2) . ?
C1 C2 1.366(3) . ?
C1 C21 1.399(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.407(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.432(2) . ?
C4 C22 1.409(2) . ?
C4 C5 1.413(2) . ?
C5 C14 1.355(2) . ?
C5 C32 1.487(2) . ?
C7 C8 1.388(2) . ?
C7 C13 1.388(2) . ?
C8 C9 1.380(2) . ?
C8 H8 0.9300 . ?
C9 C11 1.374(2) . ?
C9 N7 1.472(2) . ?
C11 C12 1.376(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.405(2) . ?
C15 C16 1.501(2) . ?
C16 C17 1.548(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.524(2) . ?
C17 C20 1.526(3) . ?
C17 C19 1.529(2) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.368(3) . ?
C21 H21 0.9300 . ?
C22 H22 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
C15 N6 C3 117.94(13) . . ?
C32 N1 C30 110.87(12) . . ?
C32 N1 C7 123.78(13) . . ?
C30 N1 C7 125.32(13) . . ?
C18 C30 N1 134.63(14) . . ?
C18 C30 C14 120.30(14) . . ?
N1 C30 C14 104.86(12) . . ?
C2 C1 C21 121.17(17) . . ?
C2 C1 H1 119.4 . . ?
C21 C1 H1 119.4 . . ?
C1 C2 C3 120.39(18) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
N6 C3 C2 117.18(15) . . ?
N6 C3 C4 124.55(14) . . ?
C2 C3 C4 118.27(16) . . ?
C22 C4 C5 125.10(15) . . ?
C22 C4 C3 119.90(15) . . ?
C5 C4 C3 114.95(14) . . ?
C14 C5 C4 118.61(14) . . ?
C14 C5 C32 107.30(13) . . ?
C4 C5 C32 134.06(14) . . ?
O3 C32 N1 125.41(15) . . ?
O3 C32 C5 129.39(15) . . ?
N1 C32 C5 105.20(12) . . ?
C8 C7 C13 120.26(15) . . ?
C8 C7 N1 120.29(14) . . ?
C13 C7 N1 119.44(14) . . ?
C9 C8 C7 117.61(15) . . ?
C9 C8 H8 121.2 . . ?
C7 C8 H8 121.2 . . ?
C11 C9 C8 123.28(16) . . ?
C11 C9 N7 118.35(15) . . ?
C8 C9 N7 118.29(15) . . ?
O5 N7 O1 123.27(17) . . ?
O5 N7 C9 118.49(17) . . ?
O1 N7 C9 118.23(15) . . ?
C9 C11 C12 118.03(16) . . ?
C9 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C11 C12 C13 120.69(17) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C7 120.04(16) . . ?
C12 C13 H13 120.0 . . ?
C7 C13 H13 120.0 . . ?
C5 C14 C15 123.50(14) . . ?
C5 C14 C30 111.64(13) . . ?
C15 C14 C30 124.86(14) . . ?
N6 C15 C14 120.24(14) . . ?
N6 C15 C16 124.30(14) . . ?
C14 C15 C16 115.36(13) . . ?
C15 C16 C17 113.30(13) . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C20 107.12(14) . . ?
C18 C17 C19 109.42(15) . . ?
C20 C17 C19 109.79(15) . . ?
C18 C17 C16 113.14(13) . . ?
C20 C17 C16 108.26(15) . . ?
C19 C17 C16 109.06(14) . . ?
C30 C18 C17 120.04(14) . . ?
C30 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C1 120.53(17) . . ?
C22 C21 H21 119.7 . . ?
C1 C21 H21 119.7 . . ?
C21 C22 C4 119.74(17) . . ?
C21 C22 H22 120.1 . . ?
C4 C22 H22 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.03
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 972996'
#######################################################################
#
#                 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 N2 O'
_chemical_formula_weight         324.37

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   33.052(6)
_cell_length_b                   7.1765(13)
_cell_length_c                   28.014(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.224(4)
_cell_angle_gamma                90.00
_cell_volume                     6559(2)
_cell_formula_units_Z            16
_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          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2720
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_T_max  0.992
_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_reflns_number            21963
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.25
_diffrn_reflns_theta_max         25.23
_reflns_number_total             5853
_reflns_number_gt                3407
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0916P)²+1.8657P] 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         5853
_refine_ls_number_parameters     455
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1802
_refine_ls_wR_factor_gt          0.1509
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.10839(6) 0.2201(3) 0.94824(7) 0.0767(7) Uani 1 1 d . . .
O2 O 0.85119(6) 0.3260(3) 0.81938(7) 0.0661(6) Uani 1 1 d . . .
N1 N 0.04098(7) 0.2976(3) 0.91809(7) 0.0557(6) Uani 1 1 d . . .
N2 N -0.00312(7) 0.1885(3) 1.06283(8) 0.0522(6) Uani 1 1 d . . .
N3 N 0.78660(6) 0.3130(3) 0.84179(7) 0.0489(6) Uani 1 1 d . . .
N4 N 0.72137(7) 0.2672(3) 0.68415(8) 0.0528(6) Uani 1 1 d . . .
C1 C 0.06157(13) 0.5214(9) 0.72719(13) 0.143(2) Uani 1 1 d . . .
H1A H 0.0397 0.6032 0.7138 0.215 Uiso 1 1 calc R . .
H1B H 0.0612 0.4123 0.7073 0.215 Uiso 1 1 calc R . .
H1C H 0.0873 0.5846 0.7283 0.215 Uiso 1 1 calc R . .
C2 C 0.05607(10) 0.4644(8) 0.77839(13) 0.0885(12) Uani 1 1 d . . .
C3 C 0.05367(10) 0.2774(7) 0.78765(12) 0.0845(12) Uani 1 1 d . . .
C4 C 0.04862(10) 0.2186(6) 0.83569(12) 0.0808(10) Uani 1 1 d . . .
H4 H 0.0472 0.0927 0.8430 0.097 Uiso 1 1 calc R . .
C5 C 0.04595(8) 0.3506(5) 0.87007(9) 0.0587(8) Uani 1 1 d . . .
C6 C 0.07306(9) 0.2388(4) 0.95414(10) 0.0549(7) Uani 1 1 d . . .
C7 C 0.05386(8) 0.2111(3) 0.99814(9) 0.0458(6) Uani 1 1 d . . .
C8 C 0.06789(8) 0.1585(3) 1.04556(9) 0.0442(6) Uani 1 1 d . . .
C9 C 0.10907(9) 0.1141(4) 1.06493(10) 0.0584(8) Uani 1 1 d . . .
H9 H 0.1290 0.1168 1.0449 0.070 Uiso 1 1 calc R . .
C10 C 0.11987(10) 0.0681(4) 1.11209(11) 0.0680(9) Uani 1 1 d . . .
H10 H 0.1470 0.0411 1.1245 0.082 Uiso 1 1 calc R . .
C11 C 0.08987(11) 0.0612(5) 1.14224(11) 0.0726(9) Uani 1 1 d . . .
H11 H 0.0975 0.0283 1.1745 0.087 Uiso 1 1 calc R . .
C12 C 0.05332(12) 0.5885(7) 0.81249(13) 0.1037(14) Uani 1 1 d . . .
H12 H 0.0545 0.7146 0.8052 0.124 Uiso 1 1 calc R . .
C13 C 0.04867(11) 0.5358(6) 0.85892(12) 0.0847(11) Uani 1 1 d . . .
H13 H 0.0474 0.6259 0.8825 0.102 Uiso 1 1 calc R . .
C14 C 0.03733(9) 0.1510(4) 1.07674(9) 0.0480(7) Uani 1 1 d . . .
C15 C -0.01544(8) 0.2406(3) 1.01664(10) 0.0450(6) Uani 1 1 d . . .
C16 C -0.05646(9) 0.2875(4) 0.99606(11) 0.0557(7) Uani 1 1 d . . .
H16 H -0.0773 0.2826 1.0148 0.067 Uiso 1 1 calc R . .
C17 C -0.06494(8) 0.3394(4) 0.94871(11) 0.0560(7) Uani 1 1 d . . .
H17 H -0.0919 0.3688 0.9360 0.067 Uiso 1 1 calc R . .
C18 C -0.03500(8) 0.3514(4) 0.91760(10) 0.0536(7) Uani 1 1 d . . .
H18 H -0.0419 0.3890 0.8856 0.064 Uiso 1 1 calc R . .
C19 C 0.00391(8) 0.3060(4) 0.93650(9) 0.0458(6) Uani 1 1 d . . .
C20 C 0.01320(8) 0.2517(3) 0.98519(9) 0.0417(6) Uani 1 1 d . . .
C21 C 0.05022(10) 0.1011(4) 1.12573(10) 0.0635(8) Uani 1 1 d . . .
H21 H 0.0311 0.0958 1.1467 0.076 Uiso 1 1 calc R . .
C22 C 0.05632(17) 0.1350(8) 0.75100(16) 0.1440(19) Uani 1 1 d . . .
H22A H 0.0493 0.1889 0.7194 0.216 Uiso 1 1 calc R . .
H22B H 0.0376 0.0355 0.7547 0.216 Uiso 1 1 calc R . .
H22C H 0.0838 0.0871 0.7549 0.216 Uiso 1 1 calc R . .
C23 C 0.80527(11) 0.2639(4) 0.61559(11) 0.0677(9) Uani 1 1 d . . .
H23 H 0.8086 0.2542 0.5834 0.081 Uiso 1 1 calc R . .
C24 C 0.76721(10) 0.2567(4) 0.62728(10) 0.0598(8) Uani 1 1 d . . .
H24 H 0.7448 0.2415 0.6029 0.072 Uiso 1 1 calc R . .
C25 C 0.76062(9) 0.2719(4) 0.67581(9) 0.0497(7) Uani 1 1 d . . .
C26 C 0.79651(8) 0.2902(4) 0.71245(9) 0.0471(6) Uani 1 1 d . . .
C27 C 0.78875(8) 0.2987(4) 0.76003(9) 0.0453(6) Uani 1 1 d . . .
C28 C 0.81446(9) 0.3150(4) 0.80874(9) 0.0489(7) Uani 1 1 d . . .
C29 C 0.79827(8) 0.3173(4) 0.89274(9) 0.0474(7) Uani 1 1 d . . .
C30 C 0.78670(9) 0.1726(4) 0.92028(10) 0.0579(8) Uani 1 1 d . . .
H30 H 0.7708 0.0762 0.9050 0.070 Uiso 1 1 calc R . .
C31 C 0.79822(9) 0.1680(5) 0.97022(10) 0.0609(8) Uani 1 1 d . . .
C32 C 0.82221(9) 0.3129(5) 0.99278(9) 0.0590(8) Uani 1 1 d . . .
C33 C 0.83603(11) 0.3130(6) 1.04669(11) 0.0889(11) Uani 1 1 d . . .
H33A H 0.8533 0.4189 1.0556 0.133 Uiso 1 1 calc R . .
H33B H 0.8511 0.2008 1.0560 0.133 Uiso 1 1 calc R . .
H33C H 0.8125 0.3192 1.0628 0.133 Uiso 1 1 calc R . .
C34 C 0.71517(8) 0.2764(4) 0.73047(10) 0.0484(7) Uani 1 1 d . . .
C35 C 0.74886(8) 0.2898(3) 0.76763(9) 0.0437(6) Uani 1 1 d . . .
C36 C 0.83559(9) 0.2975(4) 0.69850(10) 0.0603(8) Uani 1 1 d . . .
H36 H 0.8588 0.3104 0.7219 0.072 Uiso 1 1 calc R . .
C37 C 0.83966(10) 0.2858(5) 0.65137(11) 0.0692(9) Uani 1 1 d . . .
H37 H 0.8656 0.2924 0.6426 0.083 Uiso 1 1 calc R . .
C38 C 0.74615(8) 0.2980(4) 0.81706(9) 0.0458(6) Uani 1 1 d . . .
C39 C 0.70859(9) 0.2931(4) 0.83084(11) 0.0591(8) Uani 1 1 d . . .
H39 H 0.7055 0.2983 0.8632 0.071 Uiso 1 1 calc R . .
C40 C 0.67410(9) 0.2796(4) 0.79338(11) 0.0623(8) Uani 1 1 d . . .
H40 H 0.6483 0.2763 0.8025 0.075 Uiso 1 1 calc R . .
C41 C 0.67602(9) 0.2711(4) 0.74553(11) 0.0607(8) Uani 1 1 d . . .
H41 H 0.6522 0.2621 0.7229 0.073 Uiso 1 1 calc R . .
C42 C 0.83307(8) 0.4563(4) 0.96484(10) 0.0588(8) Uani 1 1 d . . .
H42 H 0.8488 0.5535 0.9799 0.071 Uiso 1 1 calc R . .
C43 C 0.82142(8) 0.4612(4) 0.91508(9) 0.0528(7) Uani 1 1 d . . .
H43 H 0.8291 0.5603 0.8971 0.063 Uiso 1 1 calc R . .
C44 C 0.78549(12) 0.0035(5) 0.99825(11) 0.0910(11) Uani 1 1 d . . .
H44A H 0.7675 -0.0758 0.9768 0.137 Uiso 1 1 calc R . .
H44B H 0.7715 0.0474 1.0236 0.137 Uiso 1 1 calc R . .
H44C H 0.8094 -0.0656 1.0121 0.137 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 C6 1.213(3) . ?
O2 C28 1.205(3) . ?
N1 C19 1.405(3) . ?
N1 C6 1.407(3) . ?
N1 C5 1.433(3) . ?
N2 C15 1.346(3) . ?
N2 C14 1.358(3) . ?
N3 C28 1.406(3) . ?
N3 C38 1.408(3) . ?
N3 C29 1.418(3) . ?
N4 C34 1.348(3) . ?
N4 C25 1.355(4) . ?
C1 C2 1.530(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C12 1.320(5) . ?
C2 C3 1.371(5) . ?
C3 C4 1.446(5) . ?
C3 C22 1.461(5) . ?
C4 C5 1.364(4) . ?
C4 H4 0.9300 . ?
C5 C13 1.371(5) . ?
C6 C7 1.488(4) . ?
C7 C20 1.366(4) . ?
C7 C8 1.387(3) . ?
C8 C9 1.418(4) . ?
C8 C14 1.438(4) . ?
C9 C10 1.353(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.403(4) . ?
C10 H10 0.9300 . ?
C11 C21 1.349(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C21 1.416(4) . ?
C15 C20 1.395(3) . ?
C15 C16 1.426(4) . ?
C16 C17 1.363(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.422(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.350(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.404(4) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.351(4) . ?
C23 C37 1.399(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.415(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.445(4) . ?
C26 C27 1.398(4) . ?
C26 C36 1.409(4) . ?
C27 C35 1.370(4) . ?
C27 C28 1.492(4) . ?
C29 C43 1.375(4) . ?
C29 C30 1.383(4) . ?
C30 C31 1.390(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.396(4) . ?
C31 C44 1.515(4) . ?
C32 C42 1.375(4) . ?
C32 C33 1.506(4) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C35 1.400(4) . ?
C34 C41 1.424(4) . ?
C35 C38 1.403(3) . ?
C36 C37 1.351(4) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C38 C39 1.358(4) . ?
C39 C40 1.424(4) . ?
C39 H39 0.9300 . ?
C40 C41 1.354(4) . ?
C40 H40 0.9300 . ?
C41 H41 0.9300 . ?
C42 C43 1.386(4) . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 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
C19 N1 C6 110.5(2) . . ?
C19 N1 C5 124.9(2) . . ?
C6 N1 C5 124.5(2) . . ?
C15 N2 C14 117.6(2) . . ?
C28 N3 C38 110.3(2) . . ?
C28 N3 C29 124.1(2) . . ?
C38 N3 C29 125.5(2) . . ?
C34 N4 C25 117.5(2) . . ?
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 . . ?
C12 C2 C3 120.7(4) . . ?
C12 C2 C1 122.0(5) . . ?
C3 C2 C1 117.3(4) . . ?
C2 C3 C4 118.7(3) . . ?
C2 C3 C22 122.7(4) . . ?
C4 C3 C22 118.6(5) . . ?
C5 C4 C3 119.0(4) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C13 119.9(3) . . ?
C4 C5 N1 120.6(3) . . ?
C13 C5 N1 119.5(3) . . ?
O1 C6 N1 124.5(3) . . ?
O1 C6 C7 130.2(3) . . ?
N1 C6 C7 105.2(2) . . ?
C20 C7 C8 118.4(2) . . ?
C20 C7 C6 106.5(2) . . ?
C8 C7 C6 135.1(3) . . ?
C7 C8 C9 125.5(2) . . ?
C7 C8 C14 115.6(2) . . ?
C9 C8 C14 118.9(2) . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 119.7(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C21 C11 C10 121.9(3) . . ?
C21 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C2 C12 C13 121.7(4) . . ?
C2 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C5 C13 C12 120.0(4) . . ?
C5 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
N2 C14 C21 117.2(3) . . ?
N2 C14 C8 125.0(2) . . ?
C21 C14 C8 117.8(3) . . ?
N2 C15 C20 119.5(2) . . ?
N2 C15 C16 125.2(2) . . ?
C20 C15 C16 115.4(2) . . ?
C17 C16 C15 119.5(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 123.9(3) . . ?
C16 C17 H17 118.0 . . ?
C18 C17 H17 118.0 . . ?
C19 C18 C17 117.2(3) . . ?
C19 C18 H18 121.4 . . ?
C17 C18 H18 121.4 . . ?
C18 C19 C20 119.6(2) . . ?
C18 C19 N1 134.3(2) . . ?
C20 C19 N1 106.1(2) . . ?
C7 C20 C15 123.9(2) . . ?
C7 C20 C19 111.7(2) . . ?
C15 C20 C19 124.4(2) . . ?
C11 C21 C14 120.7(3) . . ?
C11 C21 H21 119.6 . . ?
C14 C21 H21 119.6 . . ?
C3 C22 H22A 109.5 . . ?
C3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C37 120.8(3) . . ?
C24 C23 H23 119.6 . . ?
C37 C23 H23 119.6 . . ?
C23 C24 C25 121.5(3) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 H24 119.2 . . ?
N4 C25 C24 117.6(3) . . ?
N4 C25 C26 125.4(2) . . ?
C24 C25 C26 117.0(3) . . ?
C27 C26 C36 125.4(2) . . ?
C27 C26 C25 115.2(2) . . ?
C36 C26 C25 119.4(2) . . ?
C35 C27 C26 118.3(2) . . ?
C35 C27 C28 106.4(2) . . ?
C26 C27 C28 135.3(2) . . ?
O2 C28 N3 125.3(2) . . ?
O2 C28 C27 129.4(2) . . ?
N3 C28 C27 105.3(2) . . ?
C43 C29 C30 119.6(2) . . ?
C43 C29 N3 121.1(2) . . ?
C30 C29 N3 119.4(2) . . ?
C29 C30 C31 121.6(3) . . ?
C29 C30 H30 119.2 . . ?
C31 C30 H30 119.2 . . ?
C30 C31 C32 118.8(3) . . ?
C30 C31 C44 119.1(3) . . ?
C32 C31 C44 122.1(3) . . ?
C42 C32 C31 118.7(3) . . ?
C42 C32 C33 120.4(3) . . ?
C31 C32 C33 120.9(3) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N4 C34 C35 119.6(2) . . ?
N4 C34 C41 124.7(3) . . ?
C35 C34 C41 115.7(3) . . ?
C27 C35 C34 123.9(2) . . ?
C27 C35 C38 111.5(2) . . ?
C34 C35 C38 124.6(2) . . ?
C37 C36 C26 120.5(3) . . ?
C37 C36 H36 119.7 . . ?
C26 C36 H36 119.7 . . ?
C36 C37 C23 120.7(3) . . ?
C36 C37 H37 119.7 . . ?
C23 C37 H37 119.7 . . ?
C39 C38 C35 119.0(3) . . ?
C39 C38 N3 134.5(2) . . ?
C35 C38 N3 106.4(2) . . ?
C38 C39 C40 116.9(3) . . ?
C38 C39 H39 121.5 . . ?
C40 C39 H39 121.5 . . ?
C41 C40 C39 125.0(3) . . ?
C41 C40 H40 117.5 . . ?
C39 C40 H40 117.5 . . ?
C40 C41 C34 118.8(3) . . ?
C40 C41 H41 120.6 . . ?
C34 C41 H41 120.6 . . ?
C32 C42 C43 122.4(3) . . ?
C32 C42 H42 118.8 . . ?
C43 C42 H42 118.8 . . ?
C29 C43 C42 118.9(3) . . ?
C29 C43 H43 120.6 . . ?
C42 C43 H43 120.6 . . ?
C31 C44 H44A 109.5 . . ?
C31 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C31 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.23
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.669
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 972998'
#######################################################################
#
#                 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 N2 O2'
_chemical_formula_weight         354.40

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           ?
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   6.0809(4)
_cell_length_b                   13.7871(8)
_cell_length_c                   21.3972(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.743(2)
_cell_angle_gamma                90.00
_cell_volume                     1787.75(19)
_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          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.994
_exptl_absorpt_correction_T_max  0.997
_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_reflns_number            21918
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         24.68
_reflns_number_total             3014
_reflns_number_gt                2258
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0595P)²+0.4185P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3014
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 1.0193(3) 0.68376(12) 0.01178(7) 0.0881(6) Uani 1 1 d . . .
O2 O 1.0064(2) 0.38697(10) 0.27871(6) 0.0631(4) Uani 1 1 d . . .
N1 N 0.8423(2) 0.52816(11) 0.23710(7) 0.0483(4) Uani 1 1 d . . .
N2 N 1.2674(3) 0.52699(11) 0.06881(7) 0.0529(4) Uani 1 1 d . . .
C1 C 0.7506(5) 0.5728(2) 0.46277(11) 0.0896(8) Uani 1 1 d . . .
H1A H 0.7412 0.5080 0.4788 0.134 Uiso 1 1 calc R . .
H1B H 0.6674 0.6159 0.4870 0.134 Uiso 1 1 calc R . .
H1C H 0.9021 0.5930 0.4655 0.134 Uiso 1 1 calc R . .
C2 C 0.6584(4) 0.57517(15) 0.39566(10) 0.0589(5) Uani 1 1 d . . .
C3 C 0.7863(3) 0.54621(13) 0.34829(9) 0.0502(5) Uani 1 1 d . . .
H3 H 0.9282 0.5228 0.3585 0.060 Uiso 1 1 calc R . .
C4 C 0.7057(3) 0.55164(12) 0.28608(9) 0.0461(4) Uani 1 1 d . . .
C5 C 0.9891(3) 0.44891(13) 0.23833(9) 0.0486(5) Uani 1 1 d . . .
C6 C 1.1102(3) 0.45953(12) 0.18121(9) 0.0463(4) Uani 1 1 d . . .
C7 C 1.2927(3) 0.41146(12) 0.15808(8) 0.0464(4) Uani 1 1 d . . .
C8 C 1.3639(3) 0.44903(13) 0.10094(8) 0.0478(5) Uani 1 1 d . . .
C9 C 1.5503(3) 0.40713(14) 0.07653(9) 0.0559(5) Uani 1 1 d . . .
H9 H 1.5969 0.4297 0.0388 0.067 Uiso 1 1 calc R . .
C10 C 1.6623(3) 0.33401(14) 0.10772(10) 0.0599(5) Uani 1 1 d . . .
H10 H 1.7852 0.3070 0.0912 0.072 Uiso 1 1 calc R . .
C11 C 0.4470(4) 0.60892(15) 0.37891(12) 0.0683(6) Uani 1 1 d . . .
H11 H 0.3590 0.6291 0.4100 0.082 Uiso 1 1 calc R . .
C12 C 0.8622(3) 0.58644(13) 0.18339(8) 0.0459(4) Uani 1 1 d . . .
C13 C 1.0259(3) 0.53881(12) 0.14971(8) 0.0450(4) Uani 1 1 d . . .
C14 C 1.1031(3) 0.57119(13) 0.09394(8) 0.0478(5) Uani 1 1 d . . .
C15 C 0.9916(3) 0.65916(15) 0.06472(10) 0.0572(5) Uani 1 1 d . . .
C16 C 0.8501(3) 0.72066(14) 0.10600(9) 0.0527(5) Uani 1 1 d . . .
C17 C 0.7789(3) 0.67173(14) 0.16450(9) 0.0525(5) Uani 1 1 d . . .
H17 H 0.6752 0.7019 0.1876 0.063 Uiso 1 1 calc R . .
C18 C 0.9989(4) 0.80727(16) 0.12768(12) 0.0766(7) Uani 1 1 d . . .
H18A H 0.9204 0.8491 0.1540 0.115 Uiso 1 1 calc R . .
H18B H 1.0387 0.8428 0.0917 0.115 Uiso 1 1 calc R . .
H18C H 1.1300 0.7837 0.1508 0.115 Uiso 1 1 calc R . .
C19 C 0.6460(4) 0.7576(2) 0.06661(11) 0.0826(7) Uani 1 1 d . . .
H19A H 0.5507 0.7040 0.0548 0.124 Uiso 1 1 calc R . .
H19B H 0.6904 0.7888 0.0296 0.124 Uiso 1 1 calc R . .
H19C H 0.5686 0.8031 0.0907 0.124 Uiso 1 1 calc R . .
C20 C 1.5944(4) 0.29922(14) 0.16428(10) 0.0623(6) Uani 1 1 d . . .
H20 H 1.6746 0.2501 0.1854 0.075 Uiso 1 1 calc R . .
C21 C 1.4129(3) 0.33587(13) 0.18899(9) 0.0557(5) Uani 1 1 d . . .
H21 H 1.3683 0.3110 0.2263 0.067 Uiso 1 1 calc R . .
C22 C 0.4933(3) 0.58467(14) 0.27039(10) 0.0560(5) Uani 1 1 d . . .
H22 H 0.4377 0.5876 0.2286 0.067 Uiso 1 1 calc R . .
C23 C 0.3652(4) 0.61309(15) 0.31722(12) 0.0654(6) Uani 1 1 d . . .
H23 H 0.2223 0.6353 0.3070 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 C15 1.208(2) . ?
O2 C5 1.213(2) . ?
N1 C5 1.410(2) . ?
N1 C12 1.416(2) . ?
N1 C4 1.427(2) . ?
N2 C14 1.322(2) . ?
N2 C8 1.380(2) . ?
C1 C2 1.498(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.386(3) . ?
C2 C11 1.386(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C22 1.384(3) . ?
C5 C6 1.485(3) . ?
C6 C13 1.362(2) . ?
C6 C7 1.417(3) . ?
C7 C21 1.406(3) . ?
C7 C8 1.428(3) . ?
C8 C9 1.410(3) . ?
C9 C10 1.360(3) . ?
C9 H9 0.9300 . ?
C10 C20 1.396(3) . ?
C10 H10 0.9300 . ?
C11 C23 1.373(3) . ?
C11 H11 0.9300 . ?
C12 C17 1.330(3) . ?
C12 C13 1.436(2) . ?
C13 C14 1.391(2) . ?
C14 C15 1.501(3) . ?
C15 C16 1.538(3) . ?
C16 C17 1.516(3) . ?
C16 C19 1.529(3) . ?
C16 C18 1.546(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.360(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.376(3) . ?
C22 H22 0.9300 . ?
C23 H23 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
C5 N1 C12 111.02(14) . . ?
C5 N1 C4 124.62(15) . . ?
C12 N1 C4 124.15(15) . . ?
C14 N2 C8 117.43(16) . . ?
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 . . ?
C3 C2 C11 118.2(2) . . ?
C3 C2 C1 120.4(2) . . ?
C11 C2 C1 121.4(2) . . ?
C4 C3 C2 120.86(19) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C22 120.07(17) . . ?
C3 C4 N1 120.88(17) . . ?
C22 C4 N1 118.97(17) . . ?
O2 C5 N1 125.19(17) . . ?
O2 C5 C6 129.47(17) . . ?
N1 C5 C6 105.34(15) . . ?
C13 C6 C7 118.45(17) . . ?
C13 C6 C5 107.12(16) . . ?
C7 C6 C5 134.22(17) . . ?
C21 C7 C6 125.04(17) . . ?
C21 C7 C8 119.28(17) . . ?
C6 C7 C8 115.54(16) . . ?
N2 C8 C9 117.13(17) . . ?
N2 C8 C7 124.24(16) . . ?
C9 C8 C7 118.58(17) . . ?
C10 C9 C8 120.47(19) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C20 120.52(19) . . ?
C9 C10 H10 119.7 . . ?
C20 C10 H10 119.7 . . ?
C23 C11 C2 121.1(2) . . ?
C23 C11 H11 119.4 . . ?
C2 C11 H11 119.4 . . ?
C17 C12 N1 133.84(17) . . ?
C17 C12 C13 120.96(17) . . ?
N1 C12 C13 104.90(15) . . ?
C6 C13 C14 122.82(17) . . ?
C6 C13 C12 111.53(16) . . ?
C14 C13 C12 125.52(16) . . ?
N2 C14 C13 121.40(17) . . ?
N2 C14 C15 122.26(16) . . ?
C13 C14 C15 116.34(16) . . ?
O1 C15 C14 121.65(18) . . ?
O1 C15 C16 120.79(18) . . ?
C14 C15 C16 117.48(16) . . ?
C17 C16 C19 109.20(16) . . ?
C17 C16 C15 116.13(16) . . ?
C19 C16 C15 109.54(17) . . ?
C17 C16 C18 107.21(16) . . ?
C19 C16 C18 109.66(19) . . ?
C15 C16 C18 104.89(17) . . ?
C12 C17 C16 121.10(17) . . ?
C12 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C10 121.16(19) . . ?
C21 C20 H20 119.4 . . ?
C10 C20 H20 119.4 . . ?
C20 C21 C7 119.97(18) . . ?
C20 C21 H21 120.0 . . ?
C7 C21 H21 120.0 . . ?
C23 C22 C4 119.3(2) . . ?
C23 C22 H22 120.3 . . ?
C4 C22 H22 120.3 . . ?
C11 C23 C22 120.4(2) . . ?
C11 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        24.68
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.032
_database_code_depnum_ccdc_archive 'CCDC 972995'
#######################################################################
#
#                 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 Br Cl N2 O2'
_chemical_formula_weight         453.7

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   9.1120(7)
_cell_length_b                   10.6244(8)
_cell_length_c                   11.2803(8)
_cell_angle_alpha                97.211(2)
_cell_angle_beta                 105.469(2)
_cell_angle_gamma                113.356(2)
_cell_volume                     932.65(12)
_cell_formula_units_Z            2
_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          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    2.371
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_T_max  0.789
_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_reflns_number            10841
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         25.42
_reflns_number_total             3380
_reflns_number_gt                2675
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0762P)²+1.7172P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3380
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1496
_refine_ls_wR_factor_gt          0.1336
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.31261(7) 0.00215(6) 0.13691(6) 0.0698(3) Uani 1 1 d . . .
Cl1 Cl 0.82603(17) -0.62926(12) 0.82644(13) 0.0568(3) Uani 1 1 d . . .
O1 O 1.2954(5) 0.4544(3) 0.7906(3) 0.0681(11) Uani 1 1 d . . .
O2 O 0.6469(4) -0.2292(3) 0.4507(3) 0.0522(8) Uani 1 1 d . . .
N1 N 0.8819(4) -0.1204(3) 0.6394(3) 0.0340(7) Uani 1 1 d . . .
C1 C 0.5219(6) 0.1005(5) 0.2785(4) 0.0444(10) Uani 1 1 d . . .
C2 C 0.5810(5) 0.0241(4) 0.3475(4) 0.0401(9) Uani 1 1 d . . .
H2 H 0.5203 -0.0743 0.3262 0.048 Uiso 1 1 calc R . .
C3 C 0.7348(5) 0.0952(4) 0.4512(4) 0.0344(9) Uani 1 1 d . . .
C4 C 0.8091(5) 0.0265(4) 0.5300(4) 0.0331(8) Uani 1 1 d . . .
C5 C 0.7611(5) -0.1231(4) 0.5295(4) 0.0351(9) Uani 1 1 d . . .
C6 C 0.8700(5) -0.2446(4) 0.6825(3) 0.0301(8) Uani 1 1 d . . .
C7 C 1.0147(5) -0.2534(4) 0.7490(4) 0.0362(9) Uani 1 1 d . . .
H7 H 1.1214 -0.1793 0.7643 0.043 Uiso 1 1 calc R . .
C8 C 1.0027(6) -0.3714(4) 0.7932(4) 0.0408(10) Uani 1 1 d . . .
H8 H 1.1006 -0.3769 0.8386 0.049 Uiso 1 1 calc R . .
C9 C 0.8438(5) -0.4810(4) 0.7693(4) 0.0360(9) Uani 1 1 d . . .
C10 C 0.6112(6) 0.2502(5) 0.3079(4) 0.0451(10) Uani 1 1 d . . .
H10 H 0.5690 0.3001 0.2582 0.054 Uiso 1 1 calc R . .
C11 C 0.7587(6) 0.3206(4) 0.4092(4) 0.0422(10) Uani 1 1 d . . .
H11 H 0.8162 0.4192 0.4292 0.051 Uiso 1 1 calc R . .
C12 C 0.8266(5) 0.2471(4) 0.4847(4) 0.0356(9) Uani 1 1 d . . .
N4 N 0.9777(5) 0.3251(3) 0.5839(3) 0.0377(8) Uani 1 1 d . . .
C14 C 1.0386(5) 0.2562(4) 0.6565(4) 0.0345(9) Uani 1 1 d . . .
C15 C 1.2002(6) 0.3299(4) 0.7688(4) 0.0415(10) Uani 1 1 d . . .
C16 C 1.2398(5) 0.2429(4) 0.8616(4) 0.0369(9) Uani 1 1 d . . .
C17 C 1.4305(6) 0.2803(5) 0.9009(5) 0.0542(12) Uani 1 1 d . . .
H17A H 1.4575 0.2310 0.9627 0.081 Uiso 1 1 calc R . .
H17B H 1.4976 0.3808 0.9373 0.081 Uiso 1 1 calc R . .
H17C H 1.4554 0.2522 0.8273 0.081 Uiso 1 1 calc R . .
C18 C 1.2001(7) 0.2906(5) 0.9788(4) 0.0513(11) Uani 1 1 d . . .
H18A H 1.0818 0.2694 0.9536 0.077 Uiso 1 1 calc R . .
H18B H 1.2691 0.3911 1.0148 0.077 Uiso 1 1 calc R . .
H18C H 1.2248 0.2412 1.0411 0.077 Uiso 1 1 calc R . .
C19 C 1.1368(5) 0.0816(4) 0.8134(4) 0.0372(9) Uani 1 1 d . . .
H19 H 1.1671 0.0247 0.8610 0.045 Uiso 1 1 calc R . .
C20 C 1.0049(5) 0.0211(4) 0.7050(4) 0.0309(8) Uani 1 1 d . . .
C21 C 0.6980(6) -0.4758(4) 0.7011(4) 0.0390(9) Uani 1 1 d . . .
H21 H 0.5918 -0.5516 0.6837 0.047 Uiso 1 1 calc R . .
C22 C 0.7107(5) -0.3563(4) 0.6583(4) 0.0379(9) Uani 1 1 d . . .
H22 H 0.6126 -0.3510 0.6134 0.045 Uiso 1 1 calc R . .
C23 C 0.9541(5) 0.1074(4) 0.6306(4) 0.0322(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.912(5) . ?
Cl1 C9 1.741(4) . ?
O1 C15 1.207(5) . ?
O2 C5 1.212(5) . ?
N1 C5 1.410(5) . ?
N1 C20 1.417(5) . ?
N1 C6 1.436(5) . ?
C1 C2 1.354(6) . ?
C1 C10 1.414(6) . ?
C2 C3 1.403(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.419(5) . ?
C3 C12 1.434(5) . ?
C4 C23 1.352(5) . ?
C4 C5 1.471(5) . ?
C6 C7 1.378(6) . ?
C6 C22 1.390(6) . ?
C7 C8 1.382(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.379(6) . ?
C8 H8 0.9300 . ?
C9 C21 1.372(6) . ?
C10 C11 1.357(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.410(6) . ?
C11 H11 0.9300 . ?
C12 N4 1.369(5) . ?
N4 C14 1.322(5) . ?
C14 C23 1.406(5) . ?
C14 C15 1.493(6) . ?
C15 C16 1.544(6) . ?
C16 C19 1.528(5) . ?
C16 C18 1.538(6) . ?
C16 C17 1.541(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.326(6) . ?
C19 H19 0.9300 . ?
C20 C23 1.443(5) . ?
C21 C22 1.388(6) . ?
C21 H21 0.9300 . ?
C22 H22 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
C5 N1 C20 110.6(3) . . ?
C5 N1 C6 123.5(3) . . ?
C20 N1 C6 125.7(3) . . ?
C2 C1 C10 121.8(4) . . ?
C2 C1 Br1 118.8(3) . . ?
C10 C1 Br1 119.4(3) . . ?
C1 C2 C3 119.2(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 124.2(4) . . ?
C2 C3 C12 120.2(4) . . ?
C4 C3 C12 115.6(4) . . ?
C23 C4 C3 118.6(3) . . ?
C23 C4 C5 107.8(3) . . ?
C3 C4 C5 133.6(4) . . ?
O2 C5 N1 125.5(4) . . ?
O2 C5 C4 128.9(4) . . ?
N1 C5 C4 105.6(3) . . ?
C7 C6 C22 119.6(3) . . ?
C7 C6 N1 120.7(3) . . ?
C22 C6 N1 119.7(3) . . ?
C6 C7 C8 120.6(4) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 119.1(4) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C21 C9 C8 121.3(4) . . ?
C21 C9 Cl1 118.9(3) . . ?
C8 C9 Cl1 119.8(3) . . ?
C11 C10 C1 119.6(4) . . ?
C11 C10 H10 120.2 . . ?
C1 C10 H10 120.2 . . ?
C10 C11 C12 121.2(4) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
N4 C12 C11 117.9(4) . . ?
N4 C12 C3 124.1(4) . . ?
C11 C12 C3 117.9(4) . . ?
C14 N4 C12 117.8(3) . . ?
N4 C14 C23 121.2(4) . . ?
N4 C14 C15 122.6(3) . . ?
C23 C14 C15 116.2(4) . . ?
O1 C15 C14 122.1(4) . . ?
O1 C15 C16 120.1(4) . . ?
C14 C15 C16 117.7(3) . . ?
C19 C16 C18 107.5(3) . . ?
C19 C16 C17 108.3(3) . . ?
C18 C16 C17 109.6(4) . . ?
C19 C16 C15 116.6(3) . . ?
C18 C16 C15 105.7(3) . . ?
C17 C16 C15 109.0(4) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C16 121.2(4) . . ?
C20 C19 H19 119.4 . . ?
C16 C19 H19 119.4 . . ?
C19 C20 N1 134.8(4) . . ?
C19 C20 C23 120.3(3) . . ?
N1 C20 C23 104.8(3) . . ?
C9 C21 C22 119.3(4) . . ?
C9 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C21 C22 C6 120.1(4) . . ?
C21 C22 H22 120.0 . . ?
C6 C22 H22 120.0 . . ?
C4 C23 C14 122.6(4) . . ?
C4 C23 C20 111.1(3) . . ?
C14 C23 C20 126.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.42
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.698
_refine_diff_density_min         -1.028
_refine_diff_density_rms         0.080
_database_code_depnum_ccdc_archive 'CCDC 972994'
