# 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_d

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 N2 O'
_chemical_formula_weight         404.49

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   '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                   13.918(18)
_cell_length_b                   11.138(14)
_cell_length_c                   14.314(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.04(2)
_cell_angle_gamma                90.00
_cell_volume                     2085(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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 Area Detector'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10141
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_av_sigmaI/netI    0.0934
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3674
_reflns_number_gt                1901
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1557P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3674
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1417
_refine_ls_R_factor_gt           0.0819
_refine_ls_wR_factor_ref         0.2617
_refine_ls_wR_factor_gt          0.2291
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_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
C1 C 0.0666(3) 0.2753(3) 0.7329(3) 0.0617(10) Uani 1 1 d . . .
C2 C -0.0297(4) 0.2561(4) 0.6654(3) 0.0837(13) Uani 1 1 d . . .
H2 H -0.0421 0.1889 0.6243 0.100 Uiso 1 1 calc R . .
C3 C -0.1081(4) 0.3352(5) 0.6581(4) 0.0966(16) Uani 1 1 d . . .
H3 H -0.1726 0.3228 0.6109 0.116 Uiso 1 1 calc R . .
C4 C -0.0910(4) 0.4307(5) 0.7195(5) 0.0961(15) Uani 1 1 d . . .
H4 H -0.1444 0.4831 0.7154 0.115 Uiso 1 1 calc R . .
C5 C 0.0014(4) 0.4508(4) 0.7861(4) 0.0875(13) Uani 1 1 d . . .
H5 H 0.0123 0.5162 0.8289 0.105 Uiso 1 1 calc R . .
C6 C 0.0802(3) 0.3750(3) 0.7914(3) 0.0664(10) Uani 1 1 d . . .
C7 C 0.1532(3) 0.1908(3) 0.7452(2) 0.0595(10) Uani 1 1 d . . .
H7A H 0.1316 0.1283 0.6952 0.071 Uiso 1 1 calc R . .
H7B H 0.2096 0.2337 0.7355 0.071 Uiso 1 1 calc R . .
C8 C 0.2858(3) 0.0799(3) 0.8663(3) 0.0638(10) Uani 1 1 d . . .
H8A H 0.2848 0.0298 0.8105 0.077 Uiso 1 1 calc R . .
H8B H 0.2969 0.0277 0.9233 0.077 Uiso 1 1 calc R . .
C9 C 0.3739(3) 0.1651(3) 0.8884(2) 0.0584(9) Uani 1 1 d . . .
C11 C 0.4364(4) 0.3569(4) 0.9146(3) 0.0827(12) Uani 1 1 d . . .
H11 H 0.4242 0.4385 0.9182 0.099 Uiso 1 1 calc R . .
C12 C 0.5338(4) 0.3212(5) 0.9314(3) 0.0886(13) Uani 1 1 d . . .
H12 H 0.5872 0.3763 0.9465 0.106 Uiso 1 1 calc R . .
C13 C 0.5508(4) 0.2007(5) 0.9253(3) 0.0913(14) Uani 1 1 d . . .
H13 H 0.6164 0.1719 0.9359 0.110 Uiso 1 1 calc R . .
C14 C 0.4695(3) 0.1236(4) 0.9034(3) 0.0733(11) Uani 1 1 d . . .
H14 H 0.4801 0.0417 0.8986 0.088 Uiso 1 1 calc R . .
C15 C 0.1102(3) 0.0546(3) 0.8524(2) 0.0561(9) Uani 1 1 d . . .
H15A H 0.1035 -0.0111 0.8061 0.067 Uiso 1 1 calc R . .
H15B H 0.0452 0.0964 0.8324 0.067 Uiso 1 1 calc R . .
C16 C 0.1304(3) 0.0035(3) 0.9533(2) 0.0518(8) Uani 1 1 d . . .
C17 C 0.1215(2) 0.0764(3) 1.0288(2) 0.0532(9) Uani 1 1 d . . .
C18 C 0.1016(3) 0.2024(3) 1.0163(3) 0.0654(10) Uani 1 1 d . . .
H18 H 0.0935 0.2377 0.9552 0.079 Uiso 1 1 calc R . .
C19 C 0.0946(3) 0.2704(4) 1.0903(3) 0.0740(11) Uani 1 1 d . . .
H19 H 0.0821 0.3522 1.0798 0.089 Uiso 1 1 calc R . .
C20 C 0.1056(3) 0.2218(4) 1.1823(3) 0.0835(13) Uani 1 1 d . . .
H20 H 0.0999 0.2706 1.2329 0.100 Uiso 1 1 calc R . .
C21 C 0.1242(3) 0.1051(4) 1.1983(3) 0.0751(11) Uani 1 1 d . . .
H21 H 0.1318 0.0734 1.2606 0.090 Uiso 1 1 calc R . .
C22 C 0.1326(3) 0.0282(3) 1.1232(2) 0.0591(9) Uani 1 1 d . . .
C23 C 0.1516(3) -0.0928(4) 1.1382(3) 0.0650(10) Uani 1 1 d . . .
H23 H 0.1587 -0.1249 1.2002 0.078 Uiso 1 1 calc R . .
C24 C 0.1604(3) -0.1681(3) 1.0659(3) 0.0572(9) Uani 1 1 d . . .
C25 C 0.1784(3) -0.2927(4) 1.0818(3) 0.0742(11) Uani 1 1 d . . .
H25 H 0.1836 -0.3249 1.1432 0.089 Uiso 1 1 calc R . .
C26 C 0.1881(3) -0.3658(4) 1.0113(3) 0.0776(12) Uani 1 1 d . . .
H26 H 0.1993 -0.4475 1.0235 0.093 Uiso 1 1 calc R . .
C27 C 0.1813(3) -0.3181(4) 0.9202(3) 0.0755(11) Uani 1 1 d . . .
H27 H 0.1889 -0.3685 0.8714 0.091 Uiso 1 1 calc R . .
C28 C 0.1638(3) -0.1998(3) 0.9001(3) 0.0654(10) Uani 1 1 d . . .
H28 H 0.1600 -0.1706 0.8380 0.078 Uiso 1 1 calc R . .
C29 C 0.1513(3) -0.1203(3) 0.9712(2) 0.0552(9) Uani 1 1 d . . .
N1 N 0.1872(2) 0.1366(2) 0.84325(18) 0.0526(7) Uani 1 1 d . . .
N2 N 0.3560(3) 0.2812(3) 0.8929(3) 0.0770(10) Uani 1 1 d . . .
O1 O 0.1759(3) 0.4036(2) 0.8598(2) 0.1014(11) Uani 1 1 d . . .
H1 H 0.2200 0.3908 0.8351 0.152 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
C1 C6 1.364(5) . ?
C1 C2 1.374(6) . ?
C1 C7 1.491(5) . ?
C2 C3 1.379(6) . ?
C3 C4 1.348(7) . ?
C4 C5 1.332(7) . ?
C5 C6 1.365(6) . ?
C6 O1 1.392(5) . ?
C7 N1 1.450(4) . ?
C8 N1 1.443(5) . ?
C8 C9 1.495(5) . ?
C9 N2 1.323(5) . ?
C9 C14 1.355(5) . ?
C11 N2 1.349(5) . ?
C11 C12 1.353(6) . ?
C12 C13 1.370(7) . ?
C13 C14 1.369(6) . ?
C15 N1 1.447(4) . ?
C15 C16 1.487(5) . ?
C16 C17 1.390(5) . ?
C16 C29 1.415(5) . ?
C17 C22 1.413(5) . ?
C17 C18 1.430(5) . ?
C18 C19 1.332(5) . ?
C19 C20 1.384(6) . ?
C20 C21 1.329(6) . ?
C21 C22 1.410(5) . ?
C22 C23 1.376(5) . ?
C23 C24 1.371(5) . ?
C24 C25 1.415(5) . ?
C24 C29 1.421(5) . ?
C25 C26 1.339(6) . ?
C26 C27 1.381(6) . ?
C27 C28 1.352(5) . ?
C28 C29 1.404(5) . ?

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 C1 C2 117.1(4) . . ?
C6 C1 C7 120.3(4) . . ?
C2 C1 C7 122.6(4) . . ?
C1 C2 C3 120.7(5) . . ?
C4 C3 C2 119.8(5) . . ?
C5 C4 C3 120.7(5) . . ?
C4 C5 C6 119.8(5) . . ?
C1 C6 C5 122.0(5) . . ?
C1 C6 O1 121.1(4) . . ?
C5 C6 O1 117.0(4) . . ?
N1 C7 C1 111.1(3) . . ?
N1 C8 C9 114.6(3) . . ?
N2 C9 C14 121.0(4) . . ?
N2 C9 C8 118.5(3) . . ?
C14 C9 C8 120.4(4) . . ?
N2 C11 C12 124.0(4) . . ?
C11 C12 C13 117.4(4) . . ?
C14 C13 C12 118.8(4) . . ?
C9 C14 C13 120.9(4) . . ?
N1 C15 C16 115.4(3) . . ?
C17 C16 C29 119.7(3) . . ?
C17 C16 C15 119.6(3) . . ?
C29 C16 C15 120.5(3) . . ?
C16 C17 C22 120.8(3) . . ?
C16 C17 C18 122.7(3) . . ?
C22 C17 C18 116.4(3) . . ?
C19 C18 C17 121.5(4) . . ?
C18 C19 C20 121.3(4) . . ?
C21 C20 C19 119.8(4) . . ?
C20 C21 C22 121.7(4) . . ?
C23 C22 C21 122.6(3) . . ?
C23 C22 C17 118.2(3) . . ?
C21 C22 C17 119.2(3) . . ?
C24 C23 C22 122.9(3) . . ?
C23 C24 C25 122.4(3) . . ?
C23 C24 C29 119.4(3) . . ?
C25 C24 C29 118.3(3) . . ?
C26 C25 C24 122.2(4) . . ?
C25 C26 C27 119.1(4) . . ?
C28 C27 C26 121.6(4) . . ?
C27 C28 C29 121.2(4) . . ?
C28 C29 C16 123.5(3) . . ?
C28 C29 C24 117.6(3) . . ?
C16 C29 C24 118.9(3) . . ?
C8 N1 C15 112.3(3) . . ?
C8 N1 C7 111.9(3) . . ?
C15 N1 C7 110.1(3) . . ?
C9 N2 C11 117.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 966462'
#######################################################################
#
#                 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            'C24 H22 N2 O'
_chemical_formula_weight         354.44

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   '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                   13.197(11)
_cell_length_b                   11.102(9)
_cell_length_c                   14.265(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.786(14)
_cell_angle_gamma                90.00
_cell_volume                     1941(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9809
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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 Area Detector'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9637
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3421
_reflns_number_gt                2061
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0747P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0105(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3421
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1374
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
C1 C 0.0999(2) -0.15129(19) 0.84662(15) 0.0880(7) Uani 1 1 d . . .
H1 H 0.1691 -0.1728 0.8494 0.106 Uiso 1 1 calc R . .
C2 C 0.0198(3) -0.2392(2) 0.82472(18) 0.1088(9) Uani 1 1 d . . .
H2 H 0.0354 -0.3179 0.8123 0.131 Uiso 1 1 calc R . .
C3 C -0.0806(3) -0.2105(2) 0.82146(16) 0.1032(8) Uani 1 1 d . . .
H3 H -0.1338 -0.2699 0.8073 0.124 Uiso 1 1 calc R . .
C4 C -0.10602(19) -0.0907(2) 0.83936(13) 0.0820(6) Uani 1 1 d . . .
C5 C -0.2099(2) -0.0587(3) 0.83756(17) 0.1063(8) Uani 1 1 d . . .
H5 H -0.2645 -0.1167 0.8222 0.128 Uiso 1 1 calc R . .
C6 C -0.2312(2) 0.0549(3) 0.8578(2) 0.1142(9) Uani 1 1 d . . .
H6 H -0.3002 0.0746 0.8567 0.137 Uiso 1 1 calc R . .
C7 C -0.1505(2) 0.1432(2) 0.88054(17) 0.0998(7) Uani 1 1 d . . .
H7 H -0.1661 0.2210 0.8952 0.120 Uiso 1 1 calc R . .
C8 C -0.05009(18) 0.11743(18) 0.88154(13) 0.0764(6) Uani 1 1 d . . .
H8 H 0.0021 0.1780 0.8954 0.092 Uiso 1 1 calc R . .
C9 C -0.02373(16) -0.00083(17) 0.86163(12) 0.0667(5) Uani 1 1 d . . .
C10 C 0.08068(16) -0.03369(16) 0.86428(12) 0.0689(5) Uani 1 1 d . . .
C11 C 0.17098(15) 0.05723(16) 0.88970(13) 0.0750(6) Uani 1 1 d . . .
H11A H 0.1755 0.0994 0.9507 0.090 Uiso 1 1 calc R . .
H11B H 0.2394 0.0150 0.9040 0.090 Uiso 1 1 calc R . .
C12 C 0.16041(16) 0.08926(17) 0.71964(13) 0.0738(5) Uani 1 1 d . . .
H12A H 0.1151 0.0177 0.7063 0.089 Uiso 1 1 calc R . .
H12B H 0.2346 0.0636 0.7321 0.089 Uiso 1 1 calc R . .
C13 C 0.12202(14) 0.16762(17) 0.62705(13) 0.0639(5) Uani 1 1 d . . .
C14 C 0.12800(18) 0.12615(19) 0.53873(15) 0.0894(6) Uani 1 1 d . . .
H14 H 0.1567 0.0502 0.5365 0.107 Uiso 1 1 calc R . .
C15 C 0.09210(19) 0.1957(2) 0.45475(16) 0.0993(7) Uani 1 1 d . . .
H15 H 0.0947 0.1673 0.3944 0.119 Uiso 1 1 calc R . .
C16 C 0.05222(16) 0.3074(2) 0.45956(15) 0.0874(6) Uani 1 1 d . . .
H16 H 0.0283 0.3576 0.4033 0.105 Uiso 1 1 calc R . .
C17 C 0.04846(17) 0.34347(17) 0.54946(15) 0.0835(6) Uani 1 1 d . . .
H17 H 0.0204 0.4195 0.5528 0.100 Uiso 1 1 calc R . .
C18 C 0.24306(14) 0.23891(17) 0.84834(13) 0.0717(5) Uani 1 1 d . . .
H18A H 0.2464 0.2856 0.7921 0.086 Uiso 1 1 calc R . .
H18B H 0.3132 0.1998 0.8808 0.086 Uiso 1 1 calc R . .
C19 C 0.22287(15) 0.32220(16) 0.92224(13) 0.0680(5) Uani 1 1 d . . .
C20 C 0.29191(17) 0.32460(19) 1.02337(15) 0.0845(6) Uani 1 1 d . . .
H20 H 0.3520 0.2735 1.0453 0.101 Uiso 1 1 calc R . .
C21 C 0.2737(2) 0.4007(2) 1.09196(16) 0.0994(7) Uani 1 1 d . . .
H21 H 0.3213 0.4015 1.1591 0.119 Uiso 1 1 calc R . .
C22 C 0.1847(2) 0.4747(2) 1.05984(19) 0.1036(8) Uani 1 1 d . . .
H22 H 0.1712 0.5256 1.1057 0.124 Uiso 1 1 calc R . .
C23 C 0.1156(2) 0.47468(18) 0.96130(19) 0.0937(7) Uani 1 1 d . . .
H23 H 0.0555 0.5258 0.9402 0.112 Uiso 1 1 calc R . .
C24 C 0.13443(17) 0.39890(17) 0.89255(15) 0.0753(5) Uani 1 1 d . . .
N1 N 0.08267(12) 0.27617(14) 0.63315(11) 0.0730(5) Uani 1 1 d . . .
N2 N 0.15799(11) 0.14652(12) 0.80982(10) 0.0627(4) Uani 1 1 d . . .
O1 O 0.06203(11) 0.40573(13) 0.79447(11) 0.0972(5) Uani 1 1 d . . .
H1A H 0.0845 0.3649 0.7583 0.146 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
C1 C10 1.371(3) . ?
C1 C2 1.386(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.347(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.418(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.407(3) . ?
C4 C9 1.421(3) . ?
C5 C6 1.347(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.351(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.414(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.412(3) . ?
C10 C11 1.500(3) . ?
C11 N2 1.472(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.446(2) . ?
C12 C13 1.504(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N1 1.328(2) . ?
C13 C14 1.371(3) . ?
C14 C15 1.354(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.359(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.362(3) . ?
C16 H16 0.9300 . ?
C17 N1 1.337(2) . ?
C17 H17 0.9300 . ?
C18 N2 1.469(2) . ?
C18 C19 1.499(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C24 1.378(3) . ?
C19 C20 1.392(3) . ?
C20 C21 1.379(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.366(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.363(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(3) . ?
C23 H23 0.9300 . ?
C24 O1 1.372(2) . ?
O1 H1A 0.8200 . ?

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
C10 C1 C2 122.3(2) . . ?
C10 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 C9 119.0(2) . . ?
C3 C4 C9 119.1(2) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 120.3(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 120.5(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 123.02(19) . . ?
C10 C9 C4 118.81(19) . . ?
C8 C9 C4 118.2(2) . . ?
C1 C10 C9 119.1(2) . . ?
C1 C10 C11 120.0(2) . . ?
C9 C10 C11 120.83(17) . . ?
N2 C11 C10 114.36(14) . . ?
N2 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
N2 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
N2 C12 C13 114.56(16) . . ?
N2 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
N2 C12 H12B 108.6 . . ?
C13 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
N1 C13 C14 121.49(17) . . ?
N1 C13 C12 118.68(17) . . ?
C14 C13 C12 119.83(18) . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.4(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C17 117.77(19) . . ?
C15 C16 H16 121.1 . . ?
C17 C16 H16 121.1 . . ?
N1 C17 C16 123.9(2) . . ?
N1 C17 H17 118.0 . . ?
C16 C17 H17 118.0 . . ?
N2 C18 C19 112.54(15) . . ?
N2 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
N2 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C24 C19 C20 117.43(19) . . ?
C24 C19 C18 121.09(16) . . ?
C20 C19 C18 121.48(19) . . ?
C21 C20 C19 121.9(2) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C22 C21 C20 119.0(2) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C23 C22 C21 120.6(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 120.3(2) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
O1 C24 C19 122.49(18) . . ?
O1 C24 C23 116.7(2) . . ?
C19 C24 C23 120.8(2) . . ?
C13 N1 C17 117.35(17) . . ?
C12 N2 C18 111.95(15) . . ?
C12 N2 C11 110.98(15) . . ?
C18 N2 C11 109.12(14) . . ?
C24 O1 H1A 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.030
_database_code_depnum_ccdc_archive 'CCDC 966463'
#######################################################################
#
#                 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_yzl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 N3 O'
_chemical_formula_weight         355.43

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   ?

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                   9.929(10)
_cell_length_b                   12.099(12)
_cell_length_c                   16.261(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.512(11)
_cell_angle_gamma                90.00
_cell_volume                     1941(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9827
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12490
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3386
_reflns_number_gt                2267
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0999P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3386
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1533
_refine_ls_wR_factor_gt          0.1410
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_restrained_S_all      0.937
_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
C1 C -0.0128(2) 0.36094(18) 0.77784(13) 0.0653(6) Uani 1 1 d . . .
H1 H 0.0445 0.4164 0.8008 0.078 Uiso 1 1 calc R . .
C2 C -0.1292(2) 0.3391(2) 0.81380(14) 0.0687(7) Uani 1 1 d . . .
H2 H -0.1495 0.3783 0.8600 0.082 Uiso 1 1 calc R . .
C3 C -0.2147(3) 0.2576(2) 0.77942(16) 0.0781(7) Uani 1 1 d . . .
H3 H -0.2944 0.2414 0.8020 0.094 Uiso 1 1 calc R . .
C4 C -0.1810(2) 0.1999(2) 0.71072(15) 0.0684(6) Uani 1 1 d . . .
H4 H -0.2376 0.1444 0.6871 0.082 Uiso 1 1 calc R . .
C5 C -0.0610(2) 0.22616(15) 0.67738(12) 0.0505(5) Uani 1 1 d . . .
C6 C -0.0177(2) 0.16246(15) 0.60425(13) 0.0556(6) Uani 1 1 d . . .
H6A H 0.0239 0.0935 0.6241 0.067 Uiso 1 1 calc R . .
H6B H -0.0975 0.1446 0.5665 0.067 Uiso 1 1 calc R . .
C7 C 0.1527(2) 0.14949(15) 0.50818(11) 0.0492(5) Uani 1 1 d . . .
H7A H 0.1915 0.1929 0.4666 0.059 Uiso 1 1 calc R . .
H7B H 0.0895 0.0973 0.4797 0.059 Uiso 1 1 calc R . .
C8 C 0.26572(18) 0.08570(14) 0.55917(11) 0.0443(5) Uani 1 1 d . . .
C10 C 0.40454(18) -0.07050(14) 0.57283(12) 0.0444(5) Uani 1 1 d . . .
C11 C 0.4409(2) -0.17457(15) 0.54163(14) 0.0556(6) Uani 1 1 d . . .
H11 H 0.3946 -0.2016 0.4928 0.067 Uiso 1 1 calc R . .
C12 C 0.5443(2) -0.23587(17) 0.58308(15) 0.0627(6) Uani 1 1 d . . .
H12 H 0.5681 -0.3034 0.5615 0.075 Uiso 1 1 calc R . .
C13C C 0.6143(2) -0.19728(18) 0.65773(15) 0.0660(6) Uani 1 1 d . . .
H13C H 0.6831 -0.2400 0.6853 0.079 Uiso 1 1 calc R . .
C14 C 0.5821(2) -0.09697(19) 0.69027(14) 0.0643(6) Uani 1 1 d . . .
H14 H 0.6292 -0.0721 0.7395 0.077 Uiso 1 1 calc R . .
C15 C 0.4758(2) -0.03082(16) 0.64826(13) 0.0522(5) Uani 1 1 d . . .
C16 C 0.4366(2) 0.07384(18) 0.67751(13) 0.0638(6) Uani 1 1 d . . .
H16 H 0.4805 0.1028 0.7263 0.077 Uiso 1 1 calc R . .
C17 C 0.3337(2) 0.13193(16) 0.63343(13) 0.0590(6) Uani 1 1 d . . .
H17 H 0.3084 0.2009 0.6518 0.071 Uiso 1 1 calc R . .
C18 C 0.01368(19) 0.31771(14) 0.51034(12) 0.0484(5) Uani 1 1 d . . .
H18A H -0.0455 0.3573 0.5437 0.058 Uiso 1 1 calc R . .
H18B H -0.0411 0.2896 0.4617 0.058 Uiso 1 1 calc R . .
C19 C 0.12001(19) 0.39621(14) 0.48402(12) 0.0474(5) Uani 1 1 d . . .
C20 C 0.2114(2) 0.44978(15) 0.54417(13) 0.0521(5) Uani 1 1 d . . .
C21 C 0.3105(2) 0.52105(17) 0.51994(17) 0.0673(6) Uani 1 1 d . . .
H21 H 0.3702 0.5560 0.5599 0.081 Uiso 1 1 calc R . .
C22 C 0.3201(2) 0.54007(19) 0.43630(18) 0.0742(7) Uani 1 1 d . . .
H22 H 0.3864 0.5876 0.4207 0.089 Uiso 1 1 calc R . .
C23 C 0.2314(3) 0.48844(18) 0.37618(16) 0.0706(7) Uani 1 1 d . . .
H23 H 0.2379 0.5010 0.3203 0.085 Uiso 1 1 calc R . .
C24 C 0.1319(2) 0.41733(16) 0.40051(13) 0.0588(6) Uani 1 1 d . . .
H24 H 0.0722 0.3832 0.3601 0.071 Uiso 1 1 calc R . .
N1 N 0.07828(15) 0.22360(11) 0.55897(9) 0.0453(4) Uani 1 1 d . . .
N2 N 0.02269(17) 0.30620(13) 0.71096(10) 0.0571(5) Uani 1 1 d . . .
N3 N 0.29788(15) -0.01206(11) 0.52963(9) 0.0457(4) Uani 1 1 d . . .
O1 O 0.20694(14) 0.43737(12) 0.62833(9) 0.0682(5) Uani 1 1 d . . .
H1A H 0.1792 0.3753 0.6377 0.102 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
C1 N2 1.354(3) . ?
C1 C2 1.379(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.400(3) . ?
C4 H4 0.9300 . ?
C5 N2 1.351(3) . ?
C5 C6 1.520(3) . ?
C6 N1 1.468(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N1 1.473(2) . ?
C7 C8 1.527(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N3 1.329(2) . ?
C8 C17 1.429(3) . ?
C10 N3 1.395(2) . ?
C10 C11 1.419(3) . ?
C10 C15 1.428(3) . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C12 C13C 1.408(3) . ?
C12 H12 0.9300 . ?
C13C C14 1.376(3) . ?
C13C H13C 0.9300 . ?
C14 C15 1.434(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.422(3) . ?
C16 C17 1.373(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N1 1.489(2) . ?
C18 C19 1.517(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C24 1.400(3) . ?
C19 C20 1.414(3) . ?
C20 O1 1.383(3) . ?
C20 C21 1.397(3) . ?
C21 C22 1.394(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.388(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.400(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
O1 H1A 0.8200 . ?

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
N2 C1 C2 123.6(2) . . ?
N2 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N2 C5 C4 121.2(2) . . ?
N2 C5 C6 117.63(18) . . ?
C4 C5 C6 121.15(19) . . ?
N1 C6 C5 113.24(16) . . ?
N1 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
N1 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
N1 C7 C8 112.81(16) . . ?
N1 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N3 C8 C17 122.96(17) . . ?
N3 C8 C7 116.45(16) . . ?
C17 C8 C7 120.57(16) . . ?
N3 C10 C11 118.62(18) . . ?
N3 C10 C15 122.41(16) . . ?
C11 C10 C15 118.95(18) . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13C 120.7(2) . . ?
C11 C12 H12 119.7 . . ?
C13C C12 H12 119.7 . . ?
C14 C13C C12 120.7(2) . . ?
C14 C13C H13C 119.7 . . ?
C12 C13C H13C 119.7 . . ?
C13C C14 C15 120.0(2) . . ?
C13C C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C10 117.31(18) . . ?
C16 C15 C14 123.5(2) . . ?
C10 C15 C14 119.18(19) . . ?
C17 C16 C15 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C8 119.53(18) . . ?
C16 C17 H17 120.2 . . ?
C8 C17 H17 120.2 . . ?
N1 C18 C19 110.91(16) . . ?
N1 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.0 . . ?
C24 C19 C20 117.98(19) . . ?
C24 C19 C18 121.73(18) . . ?
C20 C19 C18 120.29(19) . . ?
O1 C20 C21 116.67(19) . . ?
O1 C20 C19 123.00(18) . . ?
C21 C20 C19 120.3(2) . . ?
C22 C21 C20 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 119.3(2) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C19 C24 C23 121.7(2) . . ?
C19 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C6 N1 C7 111.69(15) . . ?
C6 N1 C18 112.74(15) . . ?
C7 N1 C18 112.38(15) . . ?
C5 N2 C1 118.11(19) . . ?
C8 N3 C10 117.96(16) . . ?
C20 O1 H1A 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 966464'
