# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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.
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data_z
#TrackingRef 'z.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H27 N O2'
_chemical_formula_weight         373.48

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           Tetragonal
_symmetry_space_group_name_H-M   I4(1)/a

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   38.342(3)
_cell_length_b                   38.342(3)
_cell_length_c                   5.7826(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     8501.1(10)
_cell_formula_units_Z            16
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3200
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9706
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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            46864
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3736
_reflns_number_gt                2736
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0266P)^2^+7.1862P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3736
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
N1 N 0.28043(4) 0.85490(4) 0.3751(3) 0.0344(4) Uani 1 1 d . . .
O1 O 0.27219(4) 0.83453(4) 0.0055(2) 0.0525(4) Uani 1 1 d . . .
O2 O 0.32527(3) 0.85050(4) 0.1365(2) 0.0403(3) Uani 1 1 d . . .
C1 C 0.40880(4) 0.75988(4) 0.5839(3) 0.0306(4) Uani 1 1 d . . .
H1A H 0.4031 0.7494 0.4400 0.037 Uiso 1 1 calc R . .
C2 C 0.43262(5) 0.74382(5) 0.7291(4) 0.0361(5) Uani 1 1 d . . .
H2A H 0.4434 0.7226 0.6838 0.043 Uiso 1 1 calc R . .
C3 C 0.44068(5) 0.75866(5) 0.9390(4) 0.0391(5) Uani 1 1 d . . .
H3A H 0.4570 0.7476 1.0389 0.047 Uiso 1 1 calc R . .
C4 C 0.42510(5) 0.78957(5) 1.0045(3) 0.0379(5) Uani 1 1 d . . .
H4A H 0.4306 0.7997 1.1499 0.045 Uiso 1 1 calc R . .
C5 C 0.40166(5) 0.80578(5) 0.8598(3) 0.0325(4) Uani 1 1 d . . .
H5A H 0.3912 0.8271 0.9058 0.039 Uiso 1 1 calc R . .
C6 C 0.39319(4) 0.79124(4) 0.6471(3) 0.0264(4) Uani 1 1 d . . .
C7 C 0.36689(4) 0.80826(4) 0.4927(3) 0.0284(4) Uani 1 1 d . . .
C8 C 0.37142(4) 0.84565(5) 0.4288(3) 0.0300(4) Uani 1 1 d . . .
C9 C 0.33966(5) 0.86528(5) 0.3487(3) 0.0343(5) Uani 1 1 d . . .
H9A H 0.3465 0.8900 0.3180 0.041 Uiso 1 1 calc R . .
C10 C 0.30927(4) 0.86511(5) 0.5196(3) 0.0356(5) Uani 1 1 d . . .
H10A H 0.3132 0.8481 0.6456 0.043 Uiso 1 1 calc R . .
H10B H 0.3055 0.8885 0.5874 0.043 Uiso 1 1 calc R . .
C11 C 0.29030(5) 0.84555(5) 0.1617(3) 0.0360(5) Uani 1 1 d . . .
C12 C 0.24458(4) 0.85228(5) 0.4567(3) 0.0345(5) Uani 1 1 d . . .
H12A H 0.2443 0.8407 0.6096 0.041 Uiso 1 1 calc R . .
H12B H 0.2309 0.8378 0.3478 0.041 Uiso 1 1 calc R . .
C13 C 0.22798(4) 0.88787(5) 0.4767(3) 0.0301(4) Uani 1 1 d . . .
C14 C 0.23298(5) 0.90785(5) 0.6737(3) 0.0379(5) Uani 1 1 d . . .
H14A H 0.2455 0.8984 0.8008 0.046 Uiso 1 1 calc R . .
C15 C 0.21997(5) 0.94137(6) 0.6875(4) 0.0473(5) Uani 1 1 d . . .
H15A H 0.2239 0.9549 0.8225 0.057 Uiso 1 1 calc R . .
C16 C 0.20138(5) 0.95507(6) 0.5068(4) 0.0501(6) Uani 1 1 d . . .
H16A H 0.1926 0.9782 0.5161 0.060 Uiso 1 1 calc R . .
C17 C 0.19545(5) 0.93543(6) 0.3125(4) 0.0465(6) Uani 1 1 d . . .
H17A H 0.1821 0.9448 0.1887 0.056 Uiso 1 1 calc R . .
C18 C 0.20891(5) 0.90183(5) 0.2963(3) 0.0364(5) Uani 1 1 d . . .
H18A H 0.2050 0.8884 0.1606 0.044 Uiso 1 1 calc R . .
C19 C 0.40226(5) 0.86123(5) 0.4473(3) 0.0370(5) Uani 1 1 d . . .
H19A H 0.4206 0.8466 0.5000 0.044 Uiso 1 1 calc R . .
C20 C 0.41261(6) 0.89814(6) 0.3982(5) 0.0584(7) Uani 1 1 d . . .
H20A H 0.3917 0.9116 0.3523 0.070 Uiso 1 1 calc R . .
H20B H 0.4292 0.8985 0.2670 0.070 Uiso 1 1 calc R . .
C21 C 0.42919(7) 0.91518(6) 0.6037(5) 0.0786(9) Uani 1 1 d . . .
H21A H 0.4356 0.9392 0.5647 0.118 Uiso 1 1 calc R . .
H21B H 0.4502 0.9022 0.6479 0.118 Uiso 1 1 calc R . .
H21C H 0.4127 0.9153 0.7331 0.118 Uiso 1 1 calc R . .
C22 C 0.34061(5) 0.78925(5) 0.4192(3) 0.0339(5) Uani 1 1 d . . .
C23 C 0.31501(5) 0.76939(5) 0.3501(4) 0.0386(5) Uani 1 1 d . . .
C24 C 0.31762(6) 0.74918(6) 0.1278(4) 0.0573(6) Uani 1 1 d . . .
H24A H 0.3405 0.7533 0.0569 0.086 Uiso 1 1 calc R . .
H24B H 0.2992 0.7568 0.0217 0.086 Uiso 1 1 calc R . .
H24C H 0.3149 0.7242 0.1600 0.086 Uiso 1 1 calc R . .
C25 C 0.28147(5) 0.76640(5) 0.4831(4) 0.0472(6) Uani 1 1 d . . .
H25A H 0.2829 0.7807 0.6234 0.071 Uiso 1 1 calc R . .
H25B H 0.2775 0.7420 0.5258 0.071 Uiso 1 1 calc R . .
H25C H 0.2621 0.7746 0.3869 0.071 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0259(8) 0.0394(9) 0.0377(10) -0.0041(8) -0.0004(7) 0.0041(7)
O1 0.0388(8) 0.0841(11) 0.0345(8) -0.0010(8) -0.0093(7) 0.0031(8)
O2 0.0292(7) 0.0625(9) 0.0292(7) 0.0084(7) -0.0003(6) 0.0079(6)
C1 0.0295(10) 0.0279(10) 0.0344(11) 0.0006(8) -0.0003(8) -0.0029(8)
C2 0.0320(10) 0.0248(10) 0.0514(13) 0.0077(9) -0.0018(10) 0.0006(8)
C3 0.0359(11) 0.0381(11) 0.0434(13) 0.0142(10) -0.0110(10) 0.0004(9)
C4 0.0395(11) 0.0434(12) 0.0307(11) 0.0055(9) -0.0059(9) -0.0037(9)
C5 0.0312(10) 0.0349(10) 0.0314(11) -0.0003(9) 0.0011(9) 0.0051(8)
C6 0.0234(9) 0.0281(9) 0.0278(10) 0.0035(8) 0.0020(8) -0.0011(7)
C7 0.0260(9) 0.0316(10) 0.0277(10) -0.0013(8) -0.0004(8) 0.0028(8)
C8 0.0263(10) 0.0337(10) 0.0300(10) 0.0037(8) -0.0010(8) 0.0033(8)
C9 0.0311(10) 0.0366(11) 0.0353(11) 0.0048(9) -0.0024(9) 0.0034(8)
C10 0.0294(10) 0.0367(11) 0.0407(12) -0.0044(9) 0.0006(9) 0.0046(8)
C11 0.0293(11) 0.0449(12) 0.0337(12) 0.0098(10) -0.0038(9) 0.0068(9)
C12 0.0266(10) 0.0364(11) 0.0406(12) 0.0026(9) 0.0042(9) 0.0008(8)
C13 0.0199(9) 0.0372(11) 0.0331(11) 0.0038(9) 0.0060(8) -0.0008(8)
C14 0.0312(10) 0.0466(12) 0.0360(11) 0.0014(10) 0.0052(9) 0.0027(9)
C15 0.0464(13) 0.0480(13) 0.0476(14) -0.0101(11) 0.0120(11) 0.0039(10)
C16 0.0426(12) 0.0409(12) 0.0670(16) 0.0023(12) 0.0197(12) 0.0106(10)
C17 0.0315(11) 0.0538(14) 0.0541(15) 0.0192(12) 0.0035(10) 0.0104(10)
C18 0.0281(10) 0.0461(12) 0.0350(12) 0.0036(9) 0.0023(9) -0.0015(9)
C19 0.0300(10) 0.0371(11) 0.0439(12) 0.0084(9) -0.0031(9) 0.0018(8)
C20 0.0397(12) 0.0476(13) 0.0879(19) 0.0267(13) -0.0150(13) -0.0102(10)
C21 0.0784(19) 0.0414(14) 0.116(2) 0.0014(15) -0.0222(18) -0.0092(13)
C22 0.0345(11) 0.0325(10) 0.0349(11) 0.0022(9) -0.0068(9) 0.0074(9)
C23 0.0390(11) 0.0314(11) 0.0453(12) -0.0007(10) -0.0164(10) 0.0018(9)
C24 0.0602(15) 0.0540(14) 0.0576(15) -0.0138(12) -0.0176(12) -0.0004(11)
C25 0.0384(12) 0.0410(12) 0.0622(15) 0.0031(11) -0.0128(11) -0.0036(9)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.340(2) . ?
N1 C10 1.440(2) . ?
N1 C12 1.456(2) . ?
O1 C11 1.215(2) . ?
O2 C11 1.362(2) . ?
O2 C9 1.460(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.392(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.376(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.376(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.497(2) . ?
C7 C22 1.314(2) . ?
C7 C8 1.491(2) . ?
C8 C19 1.329(2) . ?
C8 C9 1.505(2) . ?
C9 C10 1.528(3) . ?
C9 H9A 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 C13 1.510(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.382(3) . ?
C13 C14 1.386(3) . ?
C14 C15 1.381(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.370(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.372(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.391(3) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C20 1.497(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.498(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.305(3) . ?
C23 C25 1.503(3) . ?
C23 C24 1.504(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C11 N1 C10 112.96(15) . . ?
C11 N1 C12 123.13(16) . . ?
C10 N1 C12 123.74(16) . . ?
C11 O2 C9 109.67(14) . . ?
C2 C1 C6 120.56(18) . . ?
C2 C1 H1A 119.7 . . ?
C6 C1 H1A 119.7 . . ?
C3 C2 C1 119.94(18) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 119.99(18) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C5 C4 C3 120.26(19) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 120.64(17) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 C1 118.61(17) . . ?
C5 C6 C7 120.70(16) . . ?
C1 C6 C7 120.65(16) . . ?
C22 C7 C8 122.86(16) . . ?
C22 C7 C6 117.88(16) . . ?
C8 C7 C6 119.26(15) . . ?
C19 C8 C7 121.07(16) . . ?
C19 C8 C9 121.34(17) . . ?
C7 C8 C9 117.58(15) . . ?
O2 C9 C8 111.75(15) . . ?
O2 C9 C10 104.69(14) . . ?
C8 C9 C10 114.57(16) . . ?
O2 C9 H9A 108.5 . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9A 108.5 . . ?
N1 C10 C9 102.20(15) . . ?
N1 C10 H10A 111.3 . . ?
C9 C10 H10A 111.3 . . ?
N1 C10 H10B 111.3 . . ?
C9 C10 H10B 111.3 . . ?
H10A C10 H10B 109.2 . . ?
O1 C11 N1 128.05(18) . . ?
O1 C11 O2 122.10(18) . . ?
N1 C11 O2 109.84(17) . . ?
N1 C12 C13 111.12(15) . . ?
N1 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
N1 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C18 C13 C14 118.67(17) . . ?
C18 C13 C12 121.00(17) . . ?
C14 C13 C12 120.27(17) . . ?
C15 C14 C13 120.8(2) . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16A 120.0 . . ?
C17 C16 H16A 120.0 . . ?
C16 C17 C18 120.1(2) . . ?
C16 C17 H17A 119.9 . . ?
C18 C17 H17A 119.9 . . ?
C13 C18 C17 120.3(2) . . ?
C13 C18 H18A 119.9 . . ?
C17 C18 H18A 119.9 . . ?
C8 C19 C20 130.20(18) . . ?
C8 C19 H19A 114.9 . . ?
C20 C19 H19A 114.9 . . ?
C19 C20 C21 112.0(2) . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C7 177.90(19) . . ?
C22 C23 C25 122.09(19) . . ?
C22 C23 C24 120.8(2) . . ?
C25 C23 C24 117.07(18) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C6 C1 C2 C3 0.8(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 C7 178.11(17) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
C2 C1 C6 C7 -178.72(16) . . . . ?
C5 C6 C7 C22 -126.27(19) . . . . ?
C1 C6 C7 C22 51.6(2) . . . . ?
C5 C6 C7 C8 53.8(2) . . . . ?
C1 C6 C7 C8 -128.41(18) . . . . ?
C22 C7 C8 C19 -160.31(19) . . . . ?
C6 C7 C8 C19 19.7(3) . . . . ?
C22 C7 C8 C9 21.3(3) . . . . ?
C6 C7 C8 C9 -158.77(16) . . . . ?
C11 O2 C9 C8 130.62(16) . . . . ?
C11 O2 C9 C10 6.06(19) . . . . ?
C19 C8 C9 O2 119.1(2) . . . . ?
C7 C8 C9 O2 -62.5(2) . . . . ?
C19 C8 C9 C10 -122.0(2) . . . . ?
C7 C8 C9 C10 56.4(2) . . . . ?
C11 N1 C10 C9 7.3(2) . . . . ?
C12 N1 C10 C9 -177.35(15) . . . . ?
O2 C9 C10 N1 -7.66(18) . . . . ?
C8 C9 C10 N1 -130.42(17) . . . . ?
C10 N1 C11 O1 176.9(2) . . . . ?
C12 N1 C11 O1 1.5(3) . . . . ?
C10 N1 C11 O2 -3.8(2) . . . . ?
C12 N1 C11 O2 -179.25(15) . . . . ?
C9 O2 C11 O1 177.57(18) . . . . ?
C9 O2 C11 N1 -1.7(2) . . . . ?
C11 N1 C12 C13 -107.5(2) . . . . ?
C10 N1 C12 C13 77.6(2) . . . . ?
N1 C12 C13 C18 93.0(2) . . . . ?
N1 C12 C13 C14 -84.0(2) . . . . ?
C18 C13 C14 C15 -1.7(3) . . . . ?
C12 C13 C14 C15 175.46(17) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C15 C16 C17 C18 -1.4(3) . . . . ?
C14 C13 C18 C17 0.7(3) . . . . ?
C12 C13 C18 C17 -176.37(17) . . . . ?
C16 C17 C18 C13 0.8(3) . . . . ?
C7 C8 C19 C20 -178.7(2) . . . . ?
C9 C8 C19 C20 -0.3(3) . . . . ?
C8 C19 C20 C21 124.0(3) . . . . ?
C8 C7 C22 C23 177(100) . . . . ?
C6 C7 C22 C23 -3(6) . . . . ?
C7 C22 C23 C25 93(6) . . . . ?
C7 C22 C23 C24 -88(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.032


_database_code_depnum_ccdc_archive 'CCDC 833031'
#######################################################################
#
#                 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_z
#TrackingRef 'web_deposit_cif_file_0_JuntaoYe_1357894109.yjt.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 N O2'
_chemical_formula_weight         321.40

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   13.9084(18)
_cell_length_b                   5.9803(8)
_cell_length_c                   22.981(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.356(4)
_cell_angle_gamma                90.00
_cell_volume                     1843.3(4)
_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       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9626
_exptl_absorpt_correction_T_max  0.9941
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20338
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3223
_reflns_number_gt                1918
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1409P)^2^+0.3272P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3223
_refine_ls_number_parameters     254
_refine_ls_number_restraints     165
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.2462
_refine_ls_wR_factor_gt          0.2050
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.131
_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 0.44130(18) 0.6069(4) 0.15953(13) 0.1026(9) Uani 1 1 d . A .
O2 O 0.38490(16) 0.5321(4) 0.24020(12) 0.0871(7) Uani 1 1 d . A .
N1 N 0.38534(18) 0.2613(4) 0.17611(12) 0.0715(7) Uani 1 1 d . A .
C5 C 0.2540(2) 0.3886(5) 0.28206(15) 0.0789(9) Uani 1 1 d D . .
C6 C 0.3493(2) 0.3376(5) 0.26597(14) 0.0755(9) Uani 1 1 d . A .
H6A H 0.3998 0.2929 0.3026 0.091 Uiso 1 1 calc R . .
C7 C 0.3407(2) 0.1563(5) 0.21847(14) 0.0725(8) Uani 1 1 d . . .
H7A H 0.3769 0.0227 0.2355 0.087 Uiso 1 1 calc R A .
H7B H 0.2716 0.1177 0.2000 0.087 Uiso 1 1 calc R . .
C8 C 0.4069(2) 0.4741(5) 0.18789(17) 0.0756(9) Uani 1 1 d . . .
C9 C 0.1641(2) 0.4395(5) 0.23154(14) 0.0733(8) Uani 1 1 d . A .
C10 C 0.0812(3) 0.3055(7) 0.22034(17) 0.0943(11) Uani 1 1 d . . .
H10A H 0.0808 0.1806 0.2444 0.113 Uiso 1 1 calc R A .
C11 C -0.0018(3) 0.3537(8) 0.1737(2) 0.1095(13) Uani 1 1 d . A .
H11A H -0.0576 0.2620 0.1674 0.131 Uiso 1 1 calc R . .
C12 C -0.0034(3) 0.5308(8) 0.13730(18) 0.1016(12) Uani 1 1 d . . .
H12A H -0.0594 0.5610 0.1058 0.122 Uiso 1 1 calc R A .
C13 C 0.0785(3) 0.6647(7) 0.1474(2) 0.1098(13) Uani 1 1 d . A .
H13A H 0.0781 0.7879 0.1226 0.132 Uiso 1 1 calc R . .
C14 C 0.1613(3) 0.6203(6) 0.19345(19) 0.0980(12) Uani 1 1 d . . .
H14A H 0.2167 0.7131 0.1993 0.118 Uiso 1 1 calc R A .
C15 C 0.3957(2) 0.1505(6) 0.12227(16) 0.0854(10) Uani 1 1 d . . .
15A H 0.4308 0.0105 0.1338 0.103 Uiso 1 1 calc R A .
H15B H 0.4364 0.2431 0.1036 0.103 Uiso 1 1 calc R . .
C16 C 0.2988(2) 0.1028(5) 0.07659(14) 0.0710(8) Uani 1 1 d . A .
C17 C 0.2211(3) 0.2536(6) 0.06375(16) 0.0878(10) Uani 1 1 d . . .
H17A H 0.2278 0.3882 0.0847 0.105 Uiso 1 1 calc R A .
C18 C 0.1346(3) 0.2096(7) 0.02094(18) 0.0987(11) Uani 1 1 d . A .
H18A H 0.0831 0.3136 0.0133 0.118 Uiso 1 1 calc R . .
C19 C 0.1231(3) 0.0158(8) -0.01061(17) 0.0967(11) Uani 1 1 d . . .
H19A H 0.0644 -0.0117 -0.0404 0.116 Uiso 1 1 calc R A .
C20 C 0.1973(3) -0.1381(7) 0.00145(17) 0.0979(11) Uani 1 1 d . A .
H20A H 0.1891 -0.2721 -0.0198 0.118 Uiso 1 1 calc R . .
C21 C 0.2843(3) -0.0976(6) 0.04470(16) 0.0883(10) Uani 1 1 d . . .
H21A H 0.3343 -0.2054 0.0529 0.106 Uiso 1 1 calc R A .
C1 C 0.4194(10) 0.046(3) 0.4679(6) 0.199(5) Uani 0.587(11) 1 d PDU A 1
H1A H 0.4133 -0.0987 0.4846 0.298 Uiso 0.587(11) 1 calc PR A 1
H1B H 0.4306 0.1565 0.4993 0.298 Uiso 0.587(11) 1 calc PR A 1
H1C H 0.4746 0.0455 0.4501 0.298 Uiso 0.587(11) 1 calc PR A 1
C2 C 0.3236(6) 0.1013(17) 0.4195(4) 0.113(2) Uani 0.587(11) 1 d PDU A 1
H2A H 0.2670 0.0951 0.4367 0.136 Uiso 0.587(11) 1 calc PR A 1
H2B H 0.3130 -0.0071 0.3870 0.136 Uiso 0.587(11) 1 calc PR A 1
C3 C 0.3328(7) 0.3412(13) 0.3944(4) 0.0923(19) Uani 0.587(11) 1 d PDU A 1
H3A H 0.3334 0.4501 0.4258 0.111 Uiso 0.587(11) 1 calc PR A 1
H3B H 0.3957 0.3531 0.3839 0.111 Uiso 0.587(11) 1 calc PR A 1
C4 C 0.2485(9) 0.3955(17) 0.3396(4) 0.093(2) Uani 0.587(11) 1 d PDU A 1
H4A H 0.1878 0.4371 0.3462 0.112 Uiso 0.587(11) 1 calc PR A 1
C1' C 0.4057(13) -0.077(3) 0.4526(7) 0.159(5) Uani 0.413(11) 1 d PDU A 2
H1'A H 0.4169 -0.2354 0.4548 0.238 Uiso 0.413(11) 1 calc PR A 2
H1'B H 0.3784 -0.0312 0.4850 0.238 Uiso 0.413(11) 1 calc PR A 2
H1'C H 0.4677 -0.0009 0.4560 0.238 Uiso 0.413(11) 1 calc PR A 2
C2' C 0.3323(8) -0.018(2) 0.3921(5) 0.102(3) Uani 0.413(11) 1 d PDU A 2
H2'A H 0.2688 -0.0922 0.3878 0.122 Uiso 0.413(11) 1 calc PR A 2
H2'B H 0.3588 -0.0611 0.3587 0.122 Uiso 0.413(11) 1 calc PR A 2
C3' C 0.3203(12) 0.248(2) 0.3946(7) 0.114(3) Uani 0.413(11) 1 d PDU A 2
H3'A H 0.2950 0.2869 0.4287 0.137 Uiso 0.413(11) 1 calc PR A 2
H3'B H 0.3851 0.3178 0.4003 0.137 Uiso 0.413(11) 1 calc PR A 2
C4' C 0.2490(15) 0.336(3) 0.3363(5) 0.105(3) Uani 0.413(11) 1 d PDU A 2
H4'A H 0.1852 0.3585 0.3409 0.126 Uiso 0.413(11) 1 calc PRU A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0770(15) 0.0849(16) 0.136(2) 0.0327(15) 0.0103(14) -0.0231(12)
O2 0.0728(14) 0.0647(14) 0.1121(18) -0.0067(12) 0.0040(13) -0.0150(10)
N1 0.0676(15) 0.0600(15) 0.0835(17) 0.0058(12) 0.0139(13) -0.0104(11)
C5 0.069(2) 0.077(2) 0.083(2) 0.0015(17) 0.0072(17) 0.0097(15)
C6 0.0691(19) 0.0671(18) 0.080(2) 0.0045(15) 0.0014(15) 0.0010(15)
C7 0.0648(18) 0.0563(16) 0.092(2) 0.0094(15) 0.0125(16) -0.0006(13)
C8 0.0491(16) 0.0627(19) 0.101(2) 0.0135(18) -0.0046(16) -0.0074(13)
C9 0.0653(19) 0.0688(19) 0.081(2) -0.0004(15) 0.0115(15) 0.0077(15)
C10 0.074(2) 0.096(3) 0.105(3) 0.021(2) 0.011(2) -0.0054(19)
C11 0.072(2) 0.121(3) 0.123(3) -0.004(3) 0.004(2) -0.015(2)
C12 0.074(2) 0.124(3) 0.095(3) 0.006(2) 0.001(2) 0.022(2)
C13 0.089(3) 0.101(3) 0.127(3) 0.038(2) 0.007(2) 0.024(2)
C14 0.075(2) 0.074(2) 0.132(3) 0.020(2) 0.003(2) 0.0011(17)
C15 0.063(2) 0.088(2) 0.104(3) 0.004(2) 0.0200(18) 0.0021(16)
C16 0.0662(18) 0.075(2) 0.0712(18) 0.0082(15) 0.0171(15) 0.0022(15)
C17 0.083(2) 0.081(2) 0.091(2) -0.0006(18) 0.008(2) 0.0108(18)
C18 0.083(2) 0.107(3) 0.095(3) 0.004(2) 0.004(2) 0.023(2)
C19 0.082(3) 0.120(3) 0.081(2) 0.005(2) 0.0089(19) -0.008(2)
C20 0.106(3) 0.096(3) 0.084(2) -0.014(2) 0.014(2) -0.010(2)
C21 0.092(3) 0.081(2) 0.091(2) -0.0004(19) 0.023(2) 0.0111(18)
C1 0.199(8) 0.190(8) 0.182(8) 0.025(7) 0.008(6) 0.020(7)
C2 0.104(4) 0.130(5) 0.103(4) 0.046(4) 0.023(3) 0.008(4)
C3 0.101(4) 0.090(4) 0.080(3) -0.010(3) 0.015(3) 0.012(3)
C4 0.097(3) 0.095(4) 0.083(3) -0.010(3) 0.015(3) 0.030(4)
C1' 0.162(7) 0.160(8) 0.152(7) 0.017(7) 0.037(6) 0.002(7)
C2' 0.092(4) 0.124(5) 0.101(5) 0.037(4) 0.044(4) 0.019(4)
C3' 0.109(4) 0.124(5) 0.106(4) 0.000(4) 0.021(4) 0.013(5)
C4' 0.104(4) 0.109(5) 0.096(4) -0.001(4) 0.019(4) 0.023(4)

_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 C8 1.205(4) . ?
O2 C8 1.361(4) . ?
O2 C6 1.451(4) . ?
N1 C8 1.319(4) . ?
N1 C7 1.431(4) . ?
N1 C15 1.444(4) . ?
C5 C4' 1.305(10) . ?
C5 C4 1.345(10) . ?
C5 C9 1.495(4) . ?
C5 C6 1.499(5) . ?
C6 C7 1.521(4) . ?
C6 H6A 0.9800 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C10 1.372(5) . ?
C9 C14 1.385(5) . ?
C10 C11 1.381(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.347(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.360(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.369(5) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C16 1.500(5) . ?
C15 15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.379(4) . ?
C16 C21 1.391(5) . ?
C17 C18 1.363(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.354(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.356(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.369(5) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C1 C2 1.529(9) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.564(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.512(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9300 . ?
C1' C2' 1.533(10) . ?
C1' H1'A 0.9600 . ?
C1' H1'B 0.9600 . ?
C1' H1'C 0.9600 . ?
C2' C3' 1.601(9) . ?
C2' H2'A 0.9700 . ?
C2' H2'B 0.9700 . ?
C3' C4' 1.534(9) . ?
C3' H3'A 0.9700 . ?
C3' H3'B 0.9700 . ?
C4' H4'A 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
C8 O2 C6 109.7(2) . . ?
C8 N1 C7 113.6(3) . . ?
C8 N1 C15 123.4(3) . . ?
C7 N1 C15 122.8(2) . . ?
C4' C5 C4 15.6(10) . . ?
C4' C5 C9 123.1(9) . . ?
C4 C5 C9 120.3(6) . . ?
C4' C5 C6 117.5(9) . . ?
C4 C5 C6 122.2(6) . . ?
C9 C5 C6 117.5(3) . . ?
O2 C6 C5 110.9(2) . . ?
O2 C6 C7 104.4(2) . . ?
C5 C6 C7 114.6(3) . . ?
O2 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N1 C7 C6 102.1(2) . . ?
N1 C7 H7A 111.3 . . ?
C6 C7 H7A 111.3 . . ?
N1 C7 H7B 111.3 . . ?
C6 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
O1 C8 N1 128.8(4) . . ?
O1 C8 O2 121.6(3) . . ?
N1 C8 O2 109.6(3) . . ?
C10 C9 C14 117.1(3) . . ?
C10 C9 C5 121.0(3) . . ?
C14 C9 C5 121.8(3) . . ?
C9 C10 C11 120.8(4) . . ?
C9 C10 H10A 119.6 . . ?
C11 C10 H10A 119.6 . . ?
C12 C11 C10 121.3(4) . . ?
C12 C11 H11A 119.4 . . ?
C10 C11 H11A 119.4 . . ?
C11 C12 C13 118.8(4) . . ?
C11 C12 H12A 120.6 . . ?
C13 C12 H12A 120.6 . . ?
C12 C13 C14 120.8(4) . . ?
C12 C13 H13A 119.6 . . ?
C14 C13 H13A 119.6 . . ?
C13 C14 C9 121.1(4) . . ?
C13 C14 H14A 119.4 . . ?
C9 C14 H14A 119.4 . . ?
N1 C15 C16 114.3(3) . . ?
N1 C15 15A 108.7 . . ?
C16 C15 15A 108.7 . . ?
N1 C15 H15B 108.7 . . ?
C16 C15 H15B 108.7 . . ?
15A C15 H15B 107.6 . . ?
C17 C16 C21 117.0(3) . . ?
C17 C16 C15 122.2(3) . . ?
C21 C16 C15 120.7(3) . . ?
C18 C17 C16 121.3(3) . . ?
C18 C17 H17A 119.3 . . ?
C16 C17 H17A 119.3 . . ?
C19 C18 C17 120.6(4) . . ?
C19 C18 H18A 119.7 . . ?
C17 C18 H18A 119.7 . . ?
C18 C19 C20 119.7(4) . . ?
C18 C19 H19A 120.2 . . ?
C20 C19 H19A 120.2 . . ?
C19 C20 C21 120.5(4) . . ?
C19 C20 H20A 119.8 . . ?
C21 C20 H20A 119.8 . . ?
C20 C21 C16 120.8(3) . . ?
C20 C21 H21A 119.6 . . ?
C16 C21 H21A 119.6 . . ?
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 . . ?
C1 C2 C3 109.0(8) . . ?
C1 C2 H2A 109.9 . . ?
C3 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
C3 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C4 C3 C2 112.5(6) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 125.4(9) . . ?
C5 C4 H4A 117.3 . . ?
C3 C4 H4A 117.3 . . ?
C2' C1' H1'A 109.5 . . ?
C2' C1' H1'B 109.5 . . ?
H1'A C1' H1'B 109.5 . . ?
C2' C1' H1'C 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?
C1' C2' C3' 104.3(9) . . ?
C1' C2' H2'A 110.9 . . ?
C3' C2' H2'A 110.9 . . ?
C1' C2' H2'B 110.9 . . ?
C3' C2' H2'B 110.9 . . ?
H2'A C2' H2'B 108.9 . . ?
C4' C3' C2' 111.2(9) . . ?
C4' C3' H3'A 109.4 . . ?
C2' C3' H3'A 109.4 . . ?
C4' C3' H3'B 109.4 . . ?
C2' C3' H3'B 109.4 . . ?
H3'A C3' H3'B 108.0 . . ?
C5 C4' C3' 136.9(16) . . ?
C5 C4' H4'A 111.5 . . ?
C3' C4' H4'A 111.5 . . ?

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
C8 O2 C6 C5 -130.3(3) . . . . ?
C8 O2 C6 C7 -6.4(3) . . . . ?
C4' C5 C6 O2 -129.6(10) . . . . ?
C4 C5 C6 O2 -112.4(6) . . . . ?
C9 C5 C6 O2 65.8(4) . . . . ?
C4' C5 C6 C7 112.5(10) . . . . ?
C4 C5 C6 C7 129.7(6) . . . . ?
C9 C5 C6 C7 -52.1(4) . . . . ?
C8 N1 C7 C6 -7.0(3) . . . . ?
C15 N1 C7 C6 179.2(3) . . . . ?
O2 C6 C7 N1 7.7(3) . . . . ?
C5 C6 C7 N1 129.2(3) . . . . ?
C7 N1 C8 O1 -177.2(3) . . . . ?
C15 N1 C8 O1 -3.5(5) . . . . ?
C7 N1 C8 O2 3.3(3) . . . . ?
C15 N1 C8 O2 177.0(2) . . . . ?
C6 O2 C8 O1 -177.3(3) . . . . ?
C6 O2 C8 N1 2.3(3) . . . . ?
C4' C5 C9 C10 -46.2(10) . . . . ?
C4 C5 C9 C10 -64.3(7) . . . . ?
C6 C5 C9 C10 117.5(4) . . . . ?
C4' C5 C9 C14 135.0(10) . . . . ?
C4 C5 C9 C14 116.9(6) . . . . ?
C6 C5 C9 C14 -61.3(4) . . . . ?
C14 C9 C10 C11 -1.4(6) . . . . ?
C5 C9 C10 C11 179.8(3) . . . . ?
C9 C10 C11 C12 1.1(6) . . . . ?
C10 C11 C12 C13 -0.6(7) . . . . ?
C11 C12 C13 C14 0.3(7) . . . . ?
C12 C13 C14 C9 -0.7(7) . . . . ?
C10 C9 C14 C13 1.2(6) . . . . ?
C5 C9 C14 C13 180.0(3) . . . . ?
C8 N1 C15 C16 -106.3(3) . . . . ?
C7 N1 C15 C16 66.8(4) . . . . ?
N1 C15 C16 C17 40.4(4) . . . . ?
N1 C15 C16 C21 -140.3(3) . . . . ?
C21 C16 C17 C18 -1.1(5) . . . . ?
C15 C16 C17 C18 178.3(3) . . . . ?
C16 C17 C18 C19 -0.5(6) . . . . ?
C17 C18 C19 C20 1.5(6) . . . . ?
C18 C19 C20 C21 -0.9(6) . . . . ?
C19 C20 C21 C16 -0.8(6) . . . . ?
C17 C16 C21 C20 1.8(5) . . . . ?
C15 C16 C21 C20 -177.6(3) . . . . ?
C1 C2 C3 C4 170.9(10) . . . . ?
C4' C5 C4 C3 73(5) . . . . ?
C9 C5 C4 C3 178.1(6) . . . . ?
C6 C5 C4 C3 -3.8(12) . . . . ?
C2 C3 C4 C5 -101.0(11) . . . . ?
C1' C2' C3' C4' 179.5(13) . . . . ?
C4 C5 C4' C3' -105(6) . . . . ?
C9 C5 C4' C3' 170.3(14) . . . . ?
C6 C5 C4' C3' 7(2) . . . . ?
C2' C3' C4' C5 -82(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.048


_database_code_depnum_ccdc_archive 'CCDC 919207'