# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_an225

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35

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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_int_tables_number      4

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

_cell_length_a                   6.508(1)
_cell_length_b                   25.907(3)
_cell_length_c                   9.1340(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.33(1)
_cell_angle_gamma                90.00
_cell_volume                     1519.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    198(2)
_cell_measurement_reflns_used    379
_cell_measurement_theta_min      4.183
_cell_measurement_theta_max      18.317

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9582
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_process_details   
'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)'
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      198(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       φ
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17349
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         25.40
_reflns_number_total             5336
_reflns_number_gt                3958
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1999)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg, 1992)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  
'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia 1999), PLATON (Spek 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)'

_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)+(0.0410P)²+0.1807P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.9(10)
_refine_ls_number_reflns         5336
_refine_ls_number_parameters     413
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.0904
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
C1A C 0.6548(4) 0.06271(10) 0.0118(3) 0.0306(6) Uani 1 1 d . . .
H1A H 0.7693 0.0757 -0.0295 0.037 Uiso 1 1 calc R . .
C2A C 0.6000(4) 0.01100(10) 0.0005(3) 0.0322(6) Uani 1 1 d . . .
C3A C 0.4318(4) -0.00933(10) 0.0619(3) 0.0325(6) Uani 1 1 d . . .
C4A C 0.3180(4) 0.02352(10) 0.1355(3) 0.0327(6) Uani 1 1 d . . .
H4A H 0.2055 0.0102 0.1786 0.039 Uiso 1 1 calc R . .
C4AA C 0.3646(4) 0.07607(9) 0.1482(3) 0.0271(6) Uani 1 1 d . . .
C4AB C 0.2682(4) 0.11999(9) 0.2049(3) 0.0285(6) Uani 1 1 d . . .
C5A C 0.0887(4) 0.12662(10) 0.2696(3) 0.0344(6) Uani 1 1 d . . .
H5A H 0.0079 0.0976 0.2885 0.041 Uiso 1 1 calc R . .
C6A C 0.0301(4) 0.17555(10) 0.3057(3) 0.0329(6) Uani 1 1 d . . .
H6A H -0.0927 0.1804 0.3478 0.039 Uiso 1 1 calc R . .
C7A C 0.1517(4) 0.21784(10) 0.2802(3) 0.0317(6) Uani 1 1 d . . .
C8A C 0.3343(4) 0.21340(9) 0.2189(3) 0.0283(6) Uani 1 1 d . . .
C8AA C 0.3852(4) 0.16371(9) 0.1781(2) 0.0284(6) Uani 1 1 d . . .
N9A N 0.5467(3) 0.14760(8) 0.1074(2) 0.0301(5) Uani 1 1 d . . .
C9AA C 0.5345(4) 0.09460(9) 0.0861(3) 0.0284(6) Uani 1 1 d . . .
O10A O 0.7026(3) -0.02493(6) -0.07139(19) 0.0382(5) Uani 1 1 d . . .
C10A C 0.8543(4) -0.00582(11) -0.1546(3) 0.0440(7) Uani 1 1 d . . .
H10A H 0.7884 0.0187 -0.2295 0.066 Uiso 1 1 calc R . .
H10B H 0.9129 -0.0347 -0.2038 0.066 Uiso 1 1 calc R . .
H10C H 0.9659 0.0116 -0.0877 0.066 Uiso 1 1 calc R . .
C11A C 0.3732(5) -0.06554(10) 0.0383(3) 0.0466(7) Uani 1 1 d . . .
H11A H 0.3126 -0.0711 -0.0659 0.070 Uiso 1 1 calc R . .
H11B H 0.2712 -0.0749 0.1017 0.070 Uiso 1 1 calc R . .
H11C H 0.4978 -0.0870 0.0637 0.070 Uiso 1 1 calc R . .
O12A O 0.0906(3) 0.26458(6) 0.32949(18) 0.0368(5) Uani 1 1 d . . .
C12A C 0.1600(4) 0.31111(10) 0.2623(3) 0.0387(7) Uani 1 1 d . . .
C13A C 0.1344(5) 0.35296(12) 0.3732(4) 0.0549(8) Uani 1 1 d . . .
H13A H -0.0117 0.3547 0.3868 0.082 Uiso 1 1 calc R . .
H13B H 0.1764 0.3862 0.3363 0.082 Uiso 1 1 calc R . .
H13C H 0.2219 0.3451 0.4683 0.082 Uiso 1 1 calc R . .
C14A C 0.0172(5) 0.32019(12) 0.1150(3) 0.0556(8) Uani 1 1 d . . .
H14A H 0.0254 0.2906 0.0494 0.083 Uiso 1 1 calc R . .
H14B H 0.0610 0.3515 0.0683 0.083 Uiso 1 1 calc R . .
H14C H -0.1264 0.3243 0.1327 0.083 Uiso 1 1 calc R . .
C15A C 0.3811(4) 0.30515(10) 0.2384(3) 0.0404(7) Uani 1 1 d . . .
H15A H 0.4672 0.3349 0.2411 0.049 Uiso 1 1 calc R . .
C16A C 0.4591(4) 0.25952(10) 0.2138(3) 0.0378(7) Uani 1 1 d . . .
H16A H 0.5970 0.2569 0.1927 0.045 Uiso 1 1 calc R . .
C1B C -0.1175(4) -0.00083(9) 0.4044(3) 0.0300(6) Uani 1 1 d . . .
H1B H -0.2333 -0.0083 0.3298 0.036 Uiso 1 1 calc R . .
C2B C 0.0564(4) -0.03247(10) 0.4280(3) 0.0330(6) Uani 1 1 d . . .
C3B C 0.2313(4) -0.02172(10) 0.5353(3) 0.0361(6) Uani 1 1 d . . .
C4B C 0.2284(4) 0.02165(10) 0.6219(3) 0.0358(7) Uani 1 1 d . . .
H4B H 0.3455 0.0294 0.6951 0.043 Uiso 1 1 calc R . .
C4BA C 0.0557(4) 0.05444(9) 0.6036(3) 0.0295(6) Uani 1 1 d . . .
C4BB C 0.0006(4) 0.09963(10) 0.6804(3) 0.0312(6) Uani 1 1 d . . .
C5B C 0.0951(4) 0.12744(10) 0.8030(3) 0.0361(7) Uani 1 1 d . . .
H5B H 0.2309 0.1183 0.8510 0.043 Uiso 1 1 calc R . .
C6B C -0.0084(4) 0.16836(10) 0.8551(3) 0.0380(7) Uani 1 1 d . . .
H6B H 0.0556 0.1871 0.9398 0.046 Uiso 1 1 calc R . .
C7B C -0.2054(4) 0.18220(9) 0.7841(3) 0.0333(7) Uani 1 1 d . . .
C8B C -0.3094(4) 0.15542(10) 0.6605(3) 0.0307(6) Uani 1 1 d . . .
C8BA C -0.2019(4) 0.11374(9) 0.6129(3) 0.0295(6) Uani 1 1 d . . .
N9B N -0.2673(3) 0.07896(8) 0.4992(2) 0.0319(5) Uani 1 1 d . . .
C9BA C -0.1146(4) 0.04231(9) 0.4947(3) 0.0301(6) Uani 1 1 d . . .
O10B O 0.0746(3) -0.07667(7) 0.34855(19) 0.0414(5) Uani 1 1 d . . .
C10B C -0.1028(4) -0.09216(11) 0.2454(3) 0.0461(7) Uani 1 1 d . . .
H10D H -0.2237 -0.0950 0.2964 0.069 Uiso 1 1 calc R . .
H10E H -0.0756 -0.1257 0.2028 0.069 Uiso 1 1 calc R . .
H10F H -0.1312 -0.0664 0.1660 0.069 Uiso 1 1 calc R . .
C11B C 0.4149(4) -0.05799(11) 0.5542(3) 0.0516(8) Uani 1 1 d . . .
H11D H 0.5148 -0.0477 0.6415 0.077 Uiso 1 1 calc R . .
H11E H 0.4822 -0.0565 0.4658 0.077 Uiso 1 1 calc R . .
H11F H 0.3670 -0.0933 0.5677 0.077 Uiso 1 1 calc R . .
O12B O -0.3050(3) 0.22188(7) 0.84328(18) 0.0402(5) Uani 1 1 d . . .
C12B C -0.4458(4) 0.25223(10) 0.7362(3) 0.0429(7) Uani 1 1 d . . .
C13B C -0.5691(5) 0.28426(13) 0.8303(4) 0.0657(10) Uani 1 1 d . . .
H13D H -0.6450 0.2613 0.8882 0.099 Uiso 1 1 calc R . .
H13E H -0.6683 0.3061 0.7659 0.099 Uiso 1 1 calc R . .
H13F H -0.4738 0.3061 0.8978 0.099 Uiso 1 1 calc R . .
C14B C -0.3143(5) 0.28584(12) 0.6502(4) 0.0676(10) Uani 1 1 d . . .
H14D H -0.2236 0.3081 0.7194 0.101 Uiso 1 1 calc R . .
H14E H -0.4059 0.3073 0.5790 0.101 Uiso 1 1 calc R . .
H14F H -0.2290 0.2638 0.5969 0.101 Uiso 1 1 calc R . .
C15B C -0.5843(4) 0.21736(11) 0.6349(3) 0.0419(7) Uani 1 1 d . . .
H15B H -0.7221 0.2280 0.5961 0.050 Uiso 1 1 calc R . .
C16B C -0.5174(4) 0.17166(10) 0.5983(3) 0.0355(6) Uani 1 1 d . . .
H16B H -0.6052 0.1498 0.5319 0.043 Uiso 1 1 calc R . .
H9A H 0.621(4) 0.1673(10) 0.067(3) 0.034(8) Uiso 1 1 d . . .
H9B H -0.380(4) 0.0814(9) 0.442(3) 0.035(8) Uiso 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
C1A C2A 1.386(3) . ?
C1A C9AA 1.389(3) . ?
C1A H1A 0.9500 . ?
C2A O10A 1.373(3) . ?
C2A C3A 1.410(4) . ?
C3A C4A 1.373(4) . ?
C3A C11A 1.512(3) . ?
C4A C4AA 1.396(3) . ?
C4A H4A 0.9500 . ?
C4AA C9AA 1.407(3) . ?
C4AA C4AB 1.436(3) . ?
C4AB C5A 1.403(3) . ?
C4AB C8AA 1.408(3) . ?
C5A C6A 1.379(4) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.393(3) . ?
C6A H6A 0.9500 . ?
C7A O12A 1.373(3) . ?
C7A C8A 1.398(3) . ?
C8A C8AA 1.395(3) . ?
C8A C16A 1.450(3) . ?
C8AA N9A 1.384(3) . ?
N9A C9AA 1.387(3) . ?
N9A H9A 0.83(3) . ?
O10A C10A 1.429(3) . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
O12A C12A 1.457(3) . ?
C12A C15A 1.498(4) . ?
C12A C13A 1.511(4) . ?
C12A C14A 1.524(4) . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C15A C16A 1.320(4) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C1B C2B 1.386(3) . ?
C1B C9BA 1.388(3) . ?
C1B H1B 0.9500 . ?
C2B O10B 1.371(3) . ?
C2B C3B 1.404(4) . ?
C3B C4B 1.376(4) . ?
C3B C11B 1.508(4) . ?
C4B C4BA 1.397(4) . ?
C4B H4B 0.9500 . ?
C4BA C9BA 1.399(3) . ?
C4BA C4BB 1.440(3) . ?
C4BB C5B 1.389(3) . ?
C4BB C8BA 1.410(3) . ?
C5B C6B 1.382(4) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.387(4) . ?
C6B H6B 0.9500 . ?
C7B O12B 1.372(3) . ?
C7B C8B 1.402(3) . ?
C8B C8BA 1.394(3) . ?
C8B C16B 1.443(3) . ?
C8BA N9B 1.389(3) . ?
N9B C9BA 1.380(3) . ?
N9B H9B 0.83(2) . ?
O10B C10B 1.425(3) . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
O12B C12B 1.457(3) . ?
C12B C15B 1.488(4) . ?
C12B C13B 1.515(4) . ?
C12B C14B 1.525(4) . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C15B C16B 1.323(4) . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?

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
C2A C1A C9AA 116.9(2) . . ?
C2A C1A H1A 121.5 . . ?
C9AA C1A H1A 121.5 . . ?
O10A C2A C1A 123.4(2) . . ?
O10A C2A C3A 114.0(2) . . ?
C1A C2A C3A 122.6(2) . . ?
C4A C3A C2A 118.6(2) . . ?
C4A C3A C11A 121.5(2) . . ?
C2A C3A C11A 119.8(2) . . ?
C3A C4A C4AA 121.2(2) . . ?
C3A C4A H4A 119.4 . . ?
C4AA C4A H4A 119.4 . . ?
C4A C4AA C9AA 118.3(2) . . ?
C4A C4AA C4AB 134.5(2) . . ?
C9AA C4AA C4AB 107.0(2) . . ?
C5A C4AB C8AA 119.0(2) . . ?
C5A C4AB C4AA 133.7(2) . . ?
C8AA C4AB C4AA 107.1(2) . . ?
C6A C5A C4AB 119.6(2) . . ?
C6A C5A H5A 120.2 . . ?
C4AB C5A H5A 120.2 . . ?
C5A C6A C7A 119.8(2) . . ?
C5A C6A H6A 120.1 . . ?
C7A C6A H6A 120.1 . . ?
O12A C7A C6A 115.8(2) . . ?
O12A C7A C8A 120.9(2) . . ?
C6A C7A C8A 123.0(2) . . ?
C8AA C8A C7A 115.9(2) . . ?
C8AA C8A C16A 126.4(2) . . ?
C7A C8A C16A 117.5(2) . . ?
N9A C8AA C8A 129.4(2) . . ?
N9A C8AA C4AB 108.1(2) . . ?
C8A C8AA C4AB 122.5(2) . . ?
C8AA N9A C9AA 109.5(2) . . ?
C8AA N9A H9A 124.3(18) . . ?
C9AA N9A H9A 124.8(18) . . ?
N9A C9AA C1A 129.3(2) . . ?
N9A C9AA C4AA 108.2(2) . . ?
C1A C9AA C4AA 122.4(2) . . ?
C2A O10A C10A 116.83(19) . . ?
O10A C10A H10A 109.5 . . ?
O10A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
O10A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C3A C11A H11A 109.5 . . ?
C3A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C3A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C7A O12A C12A 117.72(18) . . ?
O12A C12A C15A 110.3(2) . . ?
O12A C12A C13A 103.6(2) . . ?
C15A C12A C13A 112.6(2) . . ?
O12A C12A C14A 108.2(2) . . ?
C15A C12A C14A 110.5(2) . . ?
C13A C12A C14A 111.3(2) . . ?
C12A C13A H13A 109.5 . . ?
C12A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C12A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C12A C14A H14A 109.5 . . ?
C12A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C12A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C16A C15A C12A 121.5(2) . . ?
C16A C15A H15A 119.3 . . ?
C12A C15A H15A 119.3 . . ?
C15A C16A C8A 120.0(2) . . ?
C15A C16A H16A 120.0 . . ?
C8A C16A H16A 120.0 . . ?
C2B C1B C9BA 116.9(2) . . ?
C2B C1B H1B 121.6 . . ?
C9BA C1B H1B 121.6 . . ?
O10B C2B C1B 123.4(2) . . ?
O10B C2B C3B 113.9(2) . . ?
C1B C2B C3B 122.7(2) . . ?
C4B C3B C2B 118.6(2) . . ?
C4B C3B C11B 121.8(2) . . ?
C2B C3B C11B 119.6(2) . . ?
C3B C4B C4BA 120.9(2) . . ?
C3B C4B H4B 119.6 . . ?
C4BA C4B H4B 119.6 . . ?
C4B C4BA C9BA 118.5(2) . . ?
C4B C4BA C4BB 134.0(2) . . ?
C9BA C4BA C4BB 107.3(2) . . ?
C5B C4BB C8BA 118.6(2) . . ?
C5B C4BB C4BA 134.6(2) . . ?
C8BA C4BB C4BA 106.7(2) . . ?
C6B C5B C4BB 119.9(2) . . ?
C6B C5B H5B 120.0 . . ?
C4BB C5B H5B 120.0 . . ?
C5B C6B C7B 120.2(2) . . ?
C5B C6B H6B 119.9 . . ?
C7B C6B H6B 119.9 . . ?
O12B C7B C6B 118.0(2) . . ?
O12B C7B C8B 119.4(2) . . ?
C6B C7B C8B 122.5(2) . . ?
C8BA C8B C7B 115.7(2) . . ?
C8BA C8B C16B 126.1(2) . . ?
C7B C8B C16B 118.2(2) . . ?
N9B C8BA C8B 128.9(2) . . ?
N9B C8BA C4BB 108.1(2) . . ?
C8B C8BA C4BB 123.0(2) . . ?
C9BA N9B C8BA 109.5(2) . . ?
C9BA N9B H9B 127.0(17) . . ?
C8BA N9B H9B 123.5(17) . . ?
N9B C9BA C1B 129.1(2) . . ?
N9B C9BA C4BA 108.4(2) . . ?
C1B C9BA C4BA 122.4(2) . . ?
C2B O10B C10B 117.1(2) . . ?
O10B C10B H10D 109.5 . . ?
O10B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
O10B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C3B C11B H11D 109.5 . . ?
C3B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C3B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C7B O12B C12B 115.21(17) . . ?
O12B C12B C15B 110.0(2) . . ?
O12B C12B C13B 104.4(2) . . ?
C15B C12B C13B 111.3(3) . . ?
O12B C12B C14B 108.0(2) . . ?
C15B C12B C14B 111.1(2) . . ?
C13B C12B C14B 111.9(3) . . ?
C12B C13B H13D 109.5 . . ?
C12B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C12B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C12B C14B H14D 109.5 . . ?
C12B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C12B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C16B C15B C12B 120.6(3) . . ?
C16B C15B H15B 119.7 . . ?
C12B C15B H15B 119.7 . . ?
C15B C16B C8B 119.2(2) . . ?
C15B C16B H16B 120.4 . . ?
C8B C16B H16B 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9AA C1A C2A O10A 179.1(2) . . . . ?
C9AA C1A C2A C3A -0.6(3) . . . . ?
O10A C2A C3A C4A -179.6(2) . . . . ?
C1A C2A C3A C4A 0.1(4) . . . . ?
O10A C2A C3A C11A -3.1(3) . . . . ?
C1A C2A C3A C11A 176.7(2) . . . . ?
C2A C3A C4A C4AA 0.9(4) . . . . ?
C11A C3A C4A C4AA -175.6(2) . . . . ?
C3A C4A C4AA C9AA -1.3(3) . . . . ?
C3A C4A C4AA C4AB 173.7(2) . . . . ?
C4A C4AA C4AB C5A 0.0(4) . . . . ?
C9AA C4AA C4AB C5A 175.4(2) . . . . ?
C4A C4AA C4AB C8AA -176.6(3) . . . . ?
C9AA C4AA C4AB C8AA -1.2(2) . . . . ?
C8AA C4AB C5A C6A 0.0(3) . . . . ?
C4AA C4AB C5A C6A -176.2(2) . . . . ?
C4AB C5A C6A C7A -1.2(4) . . . . ?
C5A C6A C7A O12A -175.3(2) . . . . ?
C5A C6A C7A C8A -0.1(4) . . . . ?
O12A C7A C8A C8AA 177.5(2) . . . . ?
C6A C7A C8A C8AA 2.6(3) . . . . ?
O12A C7A C8A C16A 1.9(3) . . . . ?
C6A C7A C8A C16A -173.1(2) . . . . ?
C7A C8A C8AA N9A 175.7(2) . . . . ?
C16A C8A C8AA N9A -9.1(4) . . . . ?
C7A C8A C8AA C4AB -3.8(3) . . . . ?
C16A C8A C8AA C4AB 171.4(2) . . . . ?
C5A C4AB C8AA N9A -176.94(19) . . . . ?
C4AA C4AB C8AA N9A 0.2(2) . . . . ?
C5A C4AB C8AA C8A 2.6(3) . . . . ?
C4AA C4AB C8AA C8A 179.8(2) . . . . ?
C8A C8AA N9A C9AA -178.6(2) . . . . ?
C4AB C8AA N9A C9AA 0.9(2) . . . . ?
C8AA N9A C9AA C1A 175.3(2) . . . . ?
C8AA N9A C9AA C4AA -1.6(2) . . . . ?
C2A C1A C9AA N9A -176.4(2) . . . . ?
C2A C1A C9AA C4AA 0.1(3) . . . . ?
C4A C4AA C9AA N9A 178.0(2) . . . . ?
C4AB C4AA C9AA N9A 1.7(2) . . . . ?
C4A C4AA C9AA C1A 0.8(3) . . . . ?
C4AB C4AA C9AA C1A -175.5(2) . . . . ?
C1A C2A O10A C10A -8.7(3) . . . . ?
C3A C2A O10A C10A 171.1(2) . . . . ?
C6A C7A O12A C12A -158.5(2) . . . . ?
C8A C7A O12A C12A 26.2(3) . . . . ?
C7A O12A C12A C15A -40.0(3) . . . . ?
C7A O12A C12A C13A -160.7(2) . . . . ?
C7A O12A C12A C14A 81.0(3) . . . . ?
O12A C12A C15A C16A 29.6(3) . . . . ?
C13A C12A C15A C16A 144.8(3) . . . . ?
C14A C12A C15A C16A -90.1(3) . . . . ?
C12A C15A C16A C8A -4.0(4) . . . . ?
C8AA C8A C16A C15A 171.7(3) . . . . ?
C7A C8A C16A C15A -13.1(3) . . . . ?
C9BA C1B C2B O10B 179.2(2) . . . . ?
C9BA C1B C2B C3B -1.3(3) . . . . ?
O10B C2B C3B C4B -179.6(2) . . . . ?
C1B C2B C3B C4B 0.9(4) . . . . ?
O10B C2B C3B C11B -0.4(3) . . . . ?
C1B C2B C3B C11B -179.9(2) . . . . ?
C2B C3B C4B C4BA -0.1(4) . . . . ?
C11B C3B C4B C4BA -179.3(2) . . . . ?
C3B C4B C4BA C9BA -0.2(3) . . . . ?
C3B C4B C4BA C4BB 175.4(3) . . . . ?
C4B C4BA C4BB C5B -1.3(5) . . . . ?
C9BA C4BA C4BB C5B 174.6(3) . . . . ?
C4B C4BA C4BB C8BA -176.8(3) . . . . ?
C9BA C4BA C4BB C8BA -0.9(3) . . . . ?
C8BA C4BB C5B C6B -0.8(4) . . . . ?
C4BA C4BB C5B C6B -175.9(3) . . . . ?
C4BB C5B C6B C7B -0.9(4) . . . . ?
C5B C6B C7B O12B 177.6(2) . . . . ?
C5B C6B C7B C8B 1.3(4) . . . . ?
O12B C7B C8B C8BA -176.3(2) . . . . ?
C6B C7B C8B C8BA 0.0(3) . . . . ?
O12B C7B C8B C16B 1.3(3) . . . . ?
C6B C7B C8B C16B 177.6(2) . . . . ?
C7B C8B C8BA N9B 176.9(2) . . . . ?
C16B C8B C8BA N9B -0.5(4) . . . . ?
C7B C8B C8BA C4BB -1.7(3) . . . . ?
C16B C8B C8BA C4BB -179.1(2) . . . . ?
C5B C4BB C8BA N9B -176.7(2) . . . . ?
C4BA C4BB C8BA N9B -0.4(3) . . . . ?
C5B C4BB C8BA C8B 2.2(4) . . . . ?
C4BA C4BB C8BA C8B 178.5(2) . . . . ?
C8B C8BA N9B C9BA -177.2(2) . . . . ?
C4BB C8BA N9B C9BA 1.5(3) . . . . ?
C8BA N9B C9BA C1B 176.6(2) . . . . ?
C8BA N9B C9BA C4BA -2.1(3) . . . . ?
C2B C1B C9BA N9B -177.5(2) . . . . ?
C2B C1B C9BA C4BA 1.0(3) . . . . ?
C4B C4BA C9BA N9B 178.5(2) . . . . ?
C4BB C4BA C9BA N9B 1.8(3) . . . . ?
C4B C4BA C9BA C1B -0.3(3) . . . . ?
C4BB C4BA C9BA C1B -176.9(2) . . . . ?
C1B C2B O10B C10B -5.1(3) . . . . ?
C3B C2B O10B C10B 175.4(2) . . . . ?
C6B C7B O12B C12B 149.2(2) . . . . ?
C8B C7B O12B C12B -34.3(3) . . . . ?
C7B O12B C12B C15B 48.1(3) . . . . ?
C7B O12B C12B C13B 167.5(2) . . . . ?
C7B O12B C12B C14B -73.3(3) . . . . ?
O12B C12B C15B C16B -32.2(3) . . . . ?
C13B C12B C15B C16B -147.3(3) . . . . ?
C14B C12B C15B C16B 87.3(3) . . . . ?
C12B C15B C16B C8B 1.4(4) . . . . ?
C8BA C8B C16B C15B -166.9(3) . . . . ?
C7B C8B C16B C15B 15.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.040
_chemical_compound_source        synthesis

_database_code_depnum_ccdc_archive 'CCDC 959119'
#######################################################################
#
#                 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_an227

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35

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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_int_tables_number      4

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

_cell_length_a                   6.763(1)
_cell_length_b                   8.187(1)
_cell_length_c                   13.881(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.33(1)
_cell_angle_gamma                90.00
_cell_volume                     768.37(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    198(2)
_cell_measurement_reflns_used    886
_cell_measurement_theta_min      4.134
_cell_measurement_theta_max      21.804

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9719
_exptl_absorpt_correction_T_max  0.9862
_exptl_absorpt_process_details   
'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)'
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      198(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       φ
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12481
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2940
_reflns_number_gt                2458
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1999)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg, 1992)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  
'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia 1999), PLATON (Spek 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)'

_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)+(0.0483P)²+0.1314P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(12)
_refine_ls_number_reflns         2940
_refine_ls_number_parameters     207
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.9332(3) 0.0210(2) 0.28575(13) 0.0253(4) Uani 1 1 d . . .
C2 C 1.1104(3) 0.0894(2) 0.31921(12) 0.0272(4) Uani 1 1 d . . .
O2 O 1.18109(19) 0.05355(16) 0.41054(9) 0.0318(3) Uani 1 1 d . . .
C3 C 1.2169(3) 0.2071(2) 0.26730(13) 0.0302(5) Uani 1 1 d . . .
C4 C 1.1444(3) 0.2534(2) 0.17768(14) 0.0303(5) Uani 1 1 d . . .
H4 H 1.2133 0.3330 0.1417 0.036 Uiso 1 1 calc R . .
C4A C 0.9708(3) 0.1845(2) 0.13932(13) 0.0264(4) Uani 1 1 d . . .
C4B C 0.8589(3) 0.2041(2) 0.04996(13) 0.0264(4) Uani 1 1 d . . .
C5 C 0.8833(3) 0.2972(2) -0.03330(14) 0.0302(4) Uani 1 1 d . . .
H5 H 0.9933 0.3686 -0.0383 0.036 Uiso 1 1 calc R . .
C6 C 0.7467(3) 0.2846(2) -0.10807(13) 0.0302(4) Uani 1 1 d . . .
H6 H 0.7633 0.3470 -0.1650 0.036 Uiso 1 1 calc R . .
C7 C 0.5831(3) 0.1802(2) -0.10060(13) 0.0284(4) Uani 1 1 d . . .
O7 O 0.45558(19) 0.18113(18) -0.17999(9) 0.0334(3) Uani 1 1 d . . .
C8 C 0.5521(3) 0.0864(2) -0.01962(13) 0.0271(4) Uani 1 1 d . . .
H8 H 0.4408 0.0162 -0.0148 0.032 Uiso 1 1 calc R . .
C8A C 0.6933(3) 0.1006(2) 0.05469(13) 0.0258(4) Uani 1 1 d . . .
N9 N 0.6986(2) 0.0211(2) 0.14286(11) 0.0286(4) Uani 1 1 d . . .
C9A C 0.8679(3) 0.0704(2) 0.19425(13) 0.0254(4) Uani 1 1 d . . .
C10 C 0.8256(3) -0.0867(2) 0.34943(13) 0.0297(4) Uani 1 1 d . . .
H10 H 0.6930 -0.1169 0.3339 0.036 Uiso 1 1 calc R . .
C11 C 0.9136(3) -0.1423(2) 0.42924(14) 0.0318(5) Uani 1 1 d . . .
H11 H 0.8405 -0.2070 0.4727 0.038 Uiso 1 1 calc R . .
C12 C 1.1273(3) -0.1047(3) 0.45228(14) 0.0320(5) Uani 1 1 d . . .
C13 C 1.1648(3) -0.0835(3) 0.55979(15) 0.0402(5) Uani 1 1 d . . .
H13A H 1.2978 -0.0391 0.5712 0.060 Uiso 1 1 calc R . .
H13B H 1.1540 -0.1897 0.5919 0.060 Uiso 1 1 calc R . .
H13C H 1.0667 -0.0082 0.5857 0.060 Uiso 1 1 calc R . .
C14 C 1.2633(3) -0.2347(3) 0.41136(17) 0.0464(6) Uani 1 1 d . . .
H14A H 1.2389 -0.2441 0.3417 0.070 Uiso 1 1 calc R . .
H14B H 1.2369 -0.3399 0.4422 0.070 Uiso 1 1 calc R . .
H14C H 1.4014 -0.2036 0.4239 0.070 Uiso 1 1 calc R . .
C15 C 1.4021(3) 0.2824(3) 0.31166(15) 0.0427(6) Uani 1 1 d . . .
H15A H 1.4531 0.3659 0.2682 0.064 Uiso 1 1 calc R . .
H15B H 1.5023 0.1974 0.3220 0.064 Uiso 1 1 calc R . .
H15C H 1.3707 0.3327 0.3735 0.064 Uiso 1 1 calc R . .
C16 C 0.2786(3) 0.0853(3) -0.17422(15) 0.0389(5) Uani 1 1 d . . .
H16A H 0.3137 -0.0303 -0.1676 0.058 Uiso 1 1 calc R . .
H16B H 0.1976 0.1009 -0.2330 0.058 Uiso 1 1 calc R . .
H16C H 0.2037 0.1200 -0.1182 0.058 Uiso 1 1 calc R . .
H9 H 0.614(3) -0.055(3) 0.1595(16) 0.044(7) Uiso 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
C1 C2 1.393(3) . ?
C1 C9A 1.395(3) . ?
C1 C10 1.455(3) . ?
C2 O2 1.376(2) . ?
C2 C3 1.411(3) . ?
O2 C12 1.469(2) . ?
C3 C4 1.380(3) . ?
C3 C15 1.514(3) . ?
C4 C4A 1.397(3) . ?
C4 H4 0.9500 . ?
C4A C9A 1.401(3) . ?
C4A C4B 1.447(3) . ?
C4B C5 1.397(3) . ?
C4B C8A 1.407(3) . ?
C5 C6 1.377(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.404(3) . ?
C6 H6 0.9500 . ?
C7 O7 1.384(2) . ?
C7 C8 1.381(3) . ?
O7 C16 1.435(3) . ?
C8 C8A 1.394(3) . ?
C8 H8 0.9500 . ?
C8A N9 1.386(2) . ?
N9 C9A 1.395(2) . ?
N9 H9 0.88(3) . ?
C10 C11 1.326(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.504(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.518(3) . ?
C12 C14 1.525(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9A 116.01(16) . . ?
C2 C1 C10 118.66(16) . . ?
C9A C1 C10 125.21(17) . . ?
O2 C2 C1 119.95(16) . . ?
O2 C2 C3 116.46(16) . . ?
C1 C2 C3 123.36(16) . . ?
C2 O2 C12 117.88(14) . . ?
C4 C3 C2 118.27(17) . . ?
C4 C3 C15 121.85(18) . . ?
C2 C3 C15 119.85(17) . . ?
C3 C4 C4A 120.69(17) . . ?
C3 C4 H4 119.7 . . ?
C4A C4 H4 119.7 . . ?
C4 C4A C9A 119.05(16) . . ?
C4 C4A C4B 134.43(17) . . ?
C9A C4A C4B 106.51(16) . . ?
C5 C4B C8A 118.45(17) . . ?
C5 C4B C4A 134.45(18) . . ?
C8A C4B C4A 107.10(15) . . ?
C6 C5 C4B 119.52(18) . . ?
C6 C5 H5 120.2 . . ?
C4B C5 H5 120.2 . . ?
C5 C6 C7 120.37(17) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
O7 C7 C8 123.19(17) . . ?
O7 C7 C6 114.55(16) . . ?
C8 C7 C6 122.25(17) . . ?
C7 O7 C16 117.25(15) . . ?
C7 C8 C8A 116.18(17) . . ?
C7 C8 H8 121.9 . . ?
C8A C8 H8 121.9 . . ?
N9 C8A C8 128.14(17) . . ?
N9 C8A C4B 108.63(16) . . ?
C8 C8A C4B 123.23(16) . . ?
C8A N9 C9A 108.67(16) . . ?
C8A N9 H9 124.2(15) . . ?
C9A N9 H9 126.9(15) . . ?
N9 C9A C1 128.35(17) . . ?
N9 C9A C4A 109.08(16) . . ?
C1 C9A C4A 122.57(17) . . ?
C11 C10 C1 119.61(18) . . ?
C11 C10 H10 120.2 . . ?
C1 C10 H10 120.2 . . ?
C10 C11 C12 121.20(18) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
O2 C12 C11 110.01(16) . . ?
O2 C12 C13 104.47(17) . . ?
C11 C12 C13 111.72(17) . . ?
O2 C12 C14 108.15(15) . . ?
C11 C12 C14 111.27(18) . . ?
C13 C12 C14 110.95(18) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O7 C16 H16A 109.5 . . ?
O7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A C1 C2 O2 176.92(16) . . . . ?
C10 C1 C2 O2 0.6(3) . . . . ?
C9A C1 C2 C3 2.6(3) . . . . ?
C10 C1 C2 C3 -173.77(17) . . . . ?
C1 C2 O2 C12 28.0(2) . . . . ?
C3 C2 O2 C12 -157.26(16) . . . . ?
O2 C2 C3 C4 -176.33(17) . . . . ?
C1 C2 C3 C4 -1.8(3) . . . . ?
O2 C2 C3 C15 1.9(3) . . . . ?
C1 C2 C3 C15 176.41(19) . . . . ?
C2 C3 C4 C4A -0.4(3) . . . . ?
C15 C3 C4 C4A -178.60(19) . . . . ?
C3 C4 C4A C9A 1.7(3) . . . . ?
C3 C4 C4A C4B -179.4(2) . . . . ?
C4 C4A C4B C5 1.6(4) . . . . ?
C9A C4A C4B C5 -179.4(2) . . . . ?
C4 C4A C4B C8A -179.2(2) . . . . ?
C9A C4A C4B C8A -0.2(2) . . . . ?
C8A C4B C5 C6 -0.4(3) . . . . ?
C4A C4B C5 C6 178.8(2) . . . . ?
C4B C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 O7 178.92(17) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C8 C7 O7 C16 3.2(3) . . . . ?
C6 C7 O7 C16 -175.93(17) . . . . ?
O7 C7 C8 C8A -179.28(17) . . . . ?
C6 C7 C8 C8A -0.2(3) . . . . ?
C7 C8 C8A N9 -179.82(18) . . . . ?
C7 C8 C8A C4B 0.4(3) . . . . ?
C5 C4B C8A N9 -179.91(17) . . . . ?
C4A C4B C8A N9 0.7(2) . . . . ?
C5 C4B C8A C8 -0.1(3) . . . . ?
C4A C4B C8A C8 -179.45(17) . . . . ?
C8 C8A N9 C9A 179.18(18) . . . . ?
C4B C8A N9 C9A -1.0(2) . . . . ?
C8A N9 C9A C1 -179.57(18) . . . . ?
C8A N9 C9A C4A 0.9(2) . . . . ?
C2 C1 C9A N9 179.28(18) . . . . ?
C10 C1 C9A N9 -4.6(3) . . . . ?
C2 C1 C9A C4A -1.2(3) . . . . ?
C10 C1 C9A C4A 174.85(19) . . . . ?
C4 C4A C9A N9 178.75(17) . . . . ?
C4B C4A C9A N9 -0.4(2) . . . . ?
C4 C4A C9A C1 -0.8(3) . . . . ?
C4B C4A C9A C1 180.00(17) . . . . ?
C2 C1 C10 C11 -12.9(3) . . . . ?
C9A C1 C10 C11 171.15(19) . . . . ?
C1 C10 C11 C12 -3.9(3) . . . . ?
C2 O2 C12 C11 -41.3(2) . . . . ?
C2 O2 C12 C13 -161.37(15) . . . . ?
C2 O2 C12 C14 80.4(2) . . . . ?
C10 C11 C12 O2 29.6(3) . . . . ?
C10 C11 C12 C13 145.1(2) . . . . ?
C10 C11 C12 C14 -90.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.039
_chemical_compound_source        synthesis

_database_code_depnum_ccdc_archive 'CCDC 959120'
