# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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.
#
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#  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_cd213329

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H21 N O2'
_chemical_formula_weight         403.46

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)/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                   13.6381(14)
_cell_length_b                   10.0676(11)
_cell_length_c                   15.0801(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.542(2)
_cell_angle_gamma                90.00
_cell_volume                     2069.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3286
_cell_measurement_theta_min      4.865
_cell_measurement_theta_max      51.228

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.121
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.10650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12052
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4067
_reflns_number_gt                3129
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0702P)²+0.1429P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4067
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1343
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.91069(9) 0.76251(12) -0.06214(8) 0.0470(3) Uani 1 1 d . . .
O1 O 1.06345(9) 0.68774(11) 0.08896(8) 0.0583(3) Uani 1 1 d . . .
O2 O 0.84577(11) 1.29757(12) 0.13704(8) 0.0700(4) Uani 1 1 d . . .
C1 C 0.93517(11) 0.84409(15) 0.09586(10) 0.0439(4) Uani 1 1 d . . .
C2 C 0.91660(11) 0.95425(14) 0.14832(10) 0.0447(4) Uani 1 1 d . . .
H2 H 0.9346 0.9505 0.2082 0.054 Uiso 1 1 calc R . .
C3 C 0.87250(11) 1.06976(15) 0.11619(10) 0.0447(4) Uani 1 1 d . . .
C4 C 0.84833(11) 1.07867(15) 0.02612(10) 0.0456(4) Uani 1 1 d . . .
H4 H 0.8214 1.1566 0.0030 0.055 Uiso 1 1 calc R . .
C5 C 0.86428(10) 0.97218(14) -0.02872(9) 0.0425(3) Uani 1 1 d . . .
C6 C 0.90552(10) 0.85232(14) 0.00565(9) 0.0428(4) Uani 1 1 d . . .
C7 C 0.88040(11) 0.82370(15) -0.14098(10) 0.0446(4) Uani 1 1 d . . .
C8 C 0.85012(10) 0.95343(14) -0.12280(10) 0.0432(4) Uani 1 1 d . . .
C9 C 0.82066(11) 1.03525(16) -0.19246(10) 0.0502(4) Uani 1 1 d . . .
H9 H 0.7992 1.1213 -0.1817 0.060 Uiso 1 1 calc R . .
C10 C 0.82361(12) 0.98728(18) -0.27764(10) 0.0560(4) Uani 1 1 d . . .
H10 H 0.8043 1.0424 -0.3244 0.067 Uiso 1 1 calc R . .
C11 C 0.85462(12) 0.85871(19) -0.29612(10) 0.0555(4) Uani 1 1 d . . .
C12 C 0.88212(12) 0.77477(17) -0.22693(10) 0.0524(4) Uani 1 1 d . . .
H12 H 0.9013 0.6878 -0.2379 0.063 Uiso 1 1 calc R . .
C13 C 1.00036(11) 0.73809(15) 0.13378(10) 0.0457(4) Uani 1 1 d . . .
C14 C 0.99197(11) 0.69988(14) 0.22850(10) 0.0447(4) Uani 1 1 d . . .
C15 C 1.07323(12) 0.64488(17) 0.27223(11) 0.0538(4) Uani 1 1 d . . .
H15 H 1.1307 0.6313 0.2417 0.065 Uiso 1 1 calc R . .
C16 C 1.06941(13) 0.61045(19) 0.36010(12) 0.0642(5) Uani 1 1 d . . .
H16 H 1.1243 0.5742 0.3889 0.077 Uiso 1 1 calc R . .
C17 C 0.98478(14) 0.6294(2) 0.40553(12) 0.0680(5) Uani 1 1 d . . .
H17 H 0.9827 0.6067 0.4652 0.082 Uiso 1 1 calc R . .
C18 C 0.90317(13) 0.68170(19) 0.36335(12) 0.0649(5) Uani 1 1 d . . .
H18 H 0.8458 0.6940 0.3942 0.078 Uiso 1 1 calc R . .
C19 C 0.90669(12) 0.71595(17) 0.27505(11) 0.0542(4) Uani 1 1 d . . .
H19 H 0.8511 0.7503 0.2463 0.065 Uiso 1 1 calc R . .
C20 C 0.85565(11) 1.18872(16) 0.17175(11) 0.0492(4) Uani 1 1 d . . .
C21 C 0.84577(11) 1.17892(16) 0.26996(10) 0.0475(4) Uani 1 1 d . . .
C22 C 0.80788(12) 1.06792(17) 0.31138(11) 0.0552(4) Uani 1 1 d . . .
H22 H 0.7936 0.9919 0.2785 0.066 Uiso 1 1 calc R . .
C23 C 0.79139(15) 1.0698(2) 0.40098(12) 0.0680(5) Uani 1 1 d . . .
H23 H 0.7665 0.9949 0.4286 0.082 Uiso 1 1 calc R . .
C24 C 0.81161(16) 1.1823(2) 0.44975(13) 0.0739(6) Uani 1 1 d . . .
H24 H 0.8012 1.1830 0.5104 0.089 Uiso 1 1 calc R . .
C25 C 0.84709(15) 1.2933(2) 0.40906(13) 0.0704(5) Uani 1 1 d . . .
H25 H 0.8594 1.3698 0.4420 0.084 Uiso 1 1 calc R . .
C26 C 0.86461(12) 1.29216(18) 0.31990(11) 0.0568(4) Uani 1 1 d . . .
H26 H 0.8892 1.3677 0.2928 0.068 Uiso 1 1 calc R . .
C27 C 0.93259(13) 0.62096(16) -0.05692(11) 0.0579(4) Uani 1 1 d . . .
H27A H 1.0018 0.6075 -0.0629 0.087 Uiso 1 1 calc R . .
H27B H 0.8976 0.5751 -0.1037 0.087 Uiso 1 1 calc R . .
H27C H 0.9128 0.5871 -0.0006 0.087 Uiso 1 1 calc R . .
C28 C 0.86006(18) 0.8123(2) -0.39098(12) 0.0801(6) Uani 1 1 d . . .
H28A H 0.9119 0.8587 -0.4197 0.120 Uiso 1 1 calc R . .
H28B H 0.7988 0.8302 -0.4216 0.120 Uiso 1 1 calc R . .
H28C H 0.8729 0.7186 -0.3920 0.120 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
N1 C6 1.3679(19) . ?
N1 C7 1.3919(19) . ?
N1 C27 1.458(2) . ?
O1 C13 1.2188(18) . ?
O2 C20 1.2203(19) . ?
C1 C2 1.389(2) . ?
C1 C6 1.411(2) . ?
C1 C13 1.493(2) . ?
C2 C3 1.390(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(2) . ?
C3 C20 1.483(2) . ?
C4 C5 1.375(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.423(2) . ?
C5 C8 1.439(2) . ?
C7 C12 1.387(2) . ?
C7 C8 1.399(2) . ?
C8 C9 1.386(2) . ?
C9 C10 1.374(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.392(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(2) . ?
C11 C28 1.509(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.487(2) . ?
C14 C19 1.384(2) . ?
C14 C15 1.389(2) . ?
C15 C16 1.372(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.494(2) . ?
C21 C26 1.387(2) . ?
C21 C22 1.387(2) . ?
C22 C23 1.376(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.374(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.372(2) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C7 109.01(12) . . ?
C6 N1 C27 128.35(13) . . ?
C7 N1 C27 122.31(13) . . ?
C2 C1 C6 116.75(13) . . ?
C2 C1 C13 117.92(13) . . ?
C6 C1 C13 124.29(13) . . ?
C3 C2 C1 123.57(14) . . ?
C3 C2 H2 118.2 . . ?
C1 C2 H2 118.2 . . ?
C2 C3 C4 118.87(14) . . ?
C2 C3 C20 123.42(14) . . ?
C4 C3 C20 117.58(13) . . ?
C5 C4 C3 119.97(13) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.63(13) . . ?
C4 C5 C8 132.54(13) . . ?
C6 C5 C8 106.80(12) . . ?
N1 C6 C1 131.48(13) . . ?
N1 C6 C5 108.43(12) . . ?
C1 C6 C5 120.07(13) . . ?
C12 C7 N1 128.96(14) . . ?
C12 C7 C8 121.80(14) . . ?
N1 C7 C8 109.16(13) . . ?
C9 C8 C7 119.17(14) . . ?
C9 C8 C5 134.25(14) . . ?
C7 C8 C5 106.44(13) . . ?
C10 C9 C8 118.98(15) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 122.05(15) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C12 C11 C10 119.58(15) . . ?
C12 C11 C28 120.38(17) . . ?
C10 C11 C28 120.03(16) . . ?
C11 C12 C7 118.39(16) . . ?
C11 C12 H12 120.8 . . ?
C7 C12 H12 120.8 . . ?
O1 C13 C14 119.92(13) . . ?
O1 C13 C1 120.46(14) . . ?
C14 C13 C1 119.51(13) . . ?
C19 C14 C15 118.45(14) . . ?
C19 C14 C13 122.98(13) . . ?
C15 C14 C13 118.57(14) . . ?
C16 C15 C14 120.56(16) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 120.12(16) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.33(16) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C19 119.69(17) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C14 120.83(15) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
O2 C20 C3 119.99(15) . . ?
O2 C20 C21 118.21(14) . . ?
C3 C20 C21 121.74(13) . . ?
C26 C21 C22 118.93(15) . . ?
C26 C21 C20 117.63(15) . . ?
C22 C21 C20 122.98(14) . . ?
C23 C22 C21 120.25(16) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.10(18) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 120.05(18) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.35(18) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.30(17) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
N1 C27 H27A 109.5 . . ?
N1 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N1 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C11 C28 H28A 109.5 . . ?
C11 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C11 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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 -0.9(2) . . . . ?
C13 C1 C2 C3 167.94(14) . . . . ?
C1 C2 C3 C4 -2.3(2) . . . . ?
C1 C2 C3 C20 -177.99(14) . . . . ?
C2 C3 C4 C5 2.8(2) . . . . ?
C20 C3 C4 C5 178.71(13) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C3 C4 C5 C8 -177.69(15) . . . . ?
C7 N1 C6 C1 -174.02(15) . . . . ?
C27 N1 C6 C1 12.6(3) . . . . ?
C7 N1 C6 C5 4.17(17) . . . . ?
C27 N1 C6 C5 -169.18(15) . . . . ?
C2 C1 C6 N1 -178.31(15) . . . . ?
C13 C1 C6 N1 13.6(3) . . . . ?
C2 C1 C6 C5 3.7(2) . . . . ?
C13 C1 C6 C5 -164.42(14) . . . . ?
C4 C5 C6 N1 178.30(13) . . . . ?
C8 C5 C6 N1 -3.53(16) . . . . ?
C4 C5 C6 C1 -3.3(2) . . . . ?
C8 C5 C6 C1 174.91(13) . . . . ?
C6 N1 C7 C12 173.54(15) . . . . ?
C27 N1 C7 C12 -12.6(2) . . . . ?
C6 N1 C7 C8 -3.21(17) . . . . ?
C27 N1 C7 C8 170.63(14) . . . . ?
C12 C7 C8 C9 0.3(2) . . . . ?
N1 C7 C8 C9 177.28(13) . . . . ?
C12 C7 C8 C5 -176.08(14) . . . . ?
N1 C7 C8 C5 0.95(16) . . . . ?
C4 C5 C8 C9 3.9(3) . . . . ?
C6 C5 C8 C9 -173.98(16) . . . . ?
C4 C5 C8 C7 179.42(16) . . . . ?
C6 C5 C8 C7 1.55(16) . . . . ?
C7 C8 C9 C10 -1.1(2) . . . . ?
C5 C8 C9 C10 174.00(15) . . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C9 C10 C11 C28 -177.77(16) . . . . ?
C10 C11 C12 C7 -1.8(2) . . . . ?
C28 C11 C12 C7 176.96(16) . . . . ?
N1 C7 C12 C11 -175.17(15) . . . . ?
C8 C7 C12 C11 1.2(2) . . . . ?
C2 C1 C13 O1 -136.51(16) . . . . ?
C6 C1 C13 O1 31.5(2) . . . . ?
C2 C1 C13 C14 39.8(2) . . . . ?
C6 C1 C13 C14 -152.27(14) . . . . ?
O1 C13 C14 C19 -157.93(16) . . . . ?
C1 C13 C14 C19 25.8(2) . . . . ?
O1 C13 C14 C15 21.7(2) . . . . ?
C1 C13 C14 C15 -154.57(14) . . . . ?
C19 C14 C15 C16 -1.6(2) . . . . ?
C13 C14 C15 C16 178.77(16) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C17 C18 C19 C14 -0.8(3) . . . . ?
C15 C14 C19 C18 1.8(2) . . . . ?
C13 C14 C19 C18 -178.56(16) . . . . ?
C2 C3 C20 O2 157.31(16) . . . . ?
C4 C3 C20 O2 -18.4(2) . . . . ?
C2 C3 C20 C21 -25.5(2) . . . . ?
C4 C3 C20 C21 158.78(14) . . . . ?
O2 C20 C21 C26 -24.9(2) . . . . ?
C3 C20 C21 C26 157.80(14) . . . . ?
O2 C20 C21 C22 147.19(16) . . . . ?
C3 C20 C21 C22 -30.1(2) . . . . ?
C26 C21 C22 C23 -1.4(2) . . . . ?
C20 C21 C22 C23 -173.41(16) . . . . ?
C21 C22 C23 C24 0.6(3) . . . . ?
C22 C23 C24 C25 0.8(3) . . . . ?
C23 C24 C25 C26 -1.4(3) . . . . ?
C24 C25 C26 C21 0.5(3) . . . . ?
C22 C21 C26 C25 0.8(3) . . . . ?
C20 C21 C26 C25 173.29(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.077
_database_code_depnum_ccdc_archive 'CCDC 973030'
#######################################################################
#
#                 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_cd213449

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H19 N O'
_chemical_formula_weight         361.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.8997(14)
_cell_length_b                   9.2955(15)
_cell_length_c                   11.9387(19)
_cell_angle_alpha                79.341(3)
_cell_angle_beta                 78.262(3)
_cell_angle_gamma                83.259(3)
_cell_volume                     947.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2770
_cell_measurement_theta_min      5.222
_cell_measurement_theta_max      56.680

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.123
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.59495
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5740
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3700
_reflns_number_gt                3044
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0931P)²+0.0557P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3700
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1431
_refine_ls_wR_factor_gt          0.1344
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.002
_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 0.39692(14) 0.25784(14) 0.56252(10) 0.0494(3) Uani 1 1 d . . .
O1 O 1.03764(13) 0.48567(12) 0.30788(10) 0.0642(3) Uani 1 1 d . . .
C1 C 0.40718(16) 0.29748(15) 0.66694(12) 0.0452(3) Uani 1 1 d . . .
C2 C 0.30085(18) 0.28700(17) 0.77071(13) 0.0537(4) Uani 1 1 d . . .
H2 H 0.2038 0.2555 0.7761 0.064 Uiso 1 1 calc R . .
C3 C 0.3442(2) 0.32477(18) 0.86468(13) 0.0588(4) Uani 1 1 d . . .
H3 H 0.2762 0.3158 0.9354 0.071 Uiso 1 1 calc R . .
C4 C 0.4874(2) 0.37620(18) 0.85682(13) 0.0600(4) Uani 1 1 d . . .
H4 H 0.5126 0.4020 0.9219 0.072 Uiso 1 1 calc R . .
C5 C 0.59233(18) 0.38936(16) 0.75376(12) 0.0509(4) Uani 1 1 d . . .
H5 H 0.6877 0.4241 0.7486 0.061 Uiso 1 1 calc R . .
C6 C 0.55202(16) 0.34939(14) 0.65742(11) 0.0429(3) Uani 1 1 d . . .
C7 C 0.63371(16) 0.33957(14) 0.54102(11) 0.0414(3) Uani 1 1 d . . .
C8 C 0.53469(15) 0.27992(14) 0.48669(11) 0.0433(3) Uani 1 1 d . . .
C9 C 0.58093(16) 0.24901(15) 0.37437(11) 0.0457(3) Uani 1 1 d . . .
H9 H 0.5135 0.2110 0.3395 0.055 Uiso 1 1 calc R . .
C10 C 0.72901(15) 0.27568(14) 0.31504(11) 0.0418(3) Uani 1 1 d . . .
C11 C 0.82811(16) 0.33855(14) 0.36861(11) 0.0419(3) Uani 1 1 d . . .
C12 C 0.77888(16) 0.37147(14) 0.48039(11) 0.0432(3) Uani 1 1 d . . .
H12 H 0.8437 0.4148 0.5140 0.052 Uiso 1 1 calc R . .
C13 C 0.77714(15) 0.24302(15) 0.19465(11) 0.0422(3) Uani 1 1 d . . .
C14 C 0.74561(18) 0.11134(16) 0.16809(13) 0.0518(4) Uani 1 1 d . . .
H14 H 0.6959 0.0426 0.2264 0.062 Uiso 1 1 calc R . .
C15 C 0.7874(2) 0.08145(19) 0.05568(14) 0.0641(4) Uani 1 1 d . . .
H15 H 0.7662 -0.0073 0.0394 0.077 Uiso 1 1 calc R . .
C16 C 0.8598(2) 0.1820(2) -0.03138(14) 0.0644(4) Uani 1 1 d . . .
H16 H 0.8880 0.1616 -0.1065 0.077 Uiso 1 1 calc R . .
C17 C 0.8904(2) 0.31319(19) -0.00709(13) 0.0600(4) Uani 1 1 d . . .
H17 H 0.9385 0.3822 -0.0661 0.072 Uiso 1 1 calc R . .
C18 C 0.84996(17) 0.34296(16) 0.10523(12) 0.0507(4) Uani 1 1 d . . .
H18 H 0.8721 0.4318 0.1208 0.061 Uiso 1 1 calc R . .
C19 C 0.99017(16) 0.36608(15) 0.31385(11) 0.0448(3) Uani 1 1 d . . .
C20 C 1.09878(15) 0.24117(15) 0.27554(11) 0.0433(3) Uani 1 1 d . . .
C21 C 1.07258(18) 0.09669(16) 0.32396(14) 0.0542(4) Uani 1 1 d . . .
H21 H 0.9821 0.0754 0.3763 0.065 Uiso 1 1 calc R . .
C22 C 1.1815(2) -0.01576(18) 0.29423(16) 0.0667(5) Uani 1 1 d . . .
H22 H 1.1645 -0.1125 0.3277 0.080 Uiso 1 1 calc R . .
C23 C 1.3144(2) 0.0143(2) 0.21577(16) 0.0686(5) Uani 1 1 d . . .
H23 H 1.3870 -0.0618 0.1962 0.082 Uiso 1 1 calc R . .
C24 C 1.34004(19) 0.1570(2) 0.16610(14) 0.0615(4) Uani 1 1 d . . .
H24 H 1.4292 0.1773 0.1119 0.074 Uiso 1 1 calc R . .
C25 C 1.23359(17) 0.27048(17) 0.19654(12) 0.0513(4) Uani 1 1 d . . .
H25 H 1.2524 0.3670 0.1639 0.062 Uiso 1 1 calc R . .
C26 C 0.2638(2) 0.2047(2) 0.53699(15) 0.0727(5) Uani 1 1 d . . .
H26A H 0.2498 0.2492 0.4602 0.109 Uiso 1 1 calc R . .
H26B H 0.1742 0.2296 0.5921 0.109 Uiso 1 1 calc R . .
H26C H 0.2787 0.0999 0.5417 0.109 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
N1 C8 1.3797(17) . ?
N1 C1 1.3865(18) . ?
N1 C26 1.443(2) . ?
O1 C19 1.2198(16) . ?
C1 C2 1.393(2) . ?
C1 C6 1.405(2) . ?
C2 C3 1.373(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3953(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.4451(18) . ?
C7 C12 1.3824(19) . ?
C7 C8 1.4089(18) . ?
C8 C9 1.3929(18) . ?
C9 C10 1.3899(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.4203(19) . ?
C10 C13 1.4906(18) . ?
C11 C12 1.3958(18) . ?
C11 C19 1.4880(19) . ?
C12 H12 0.9300 . ?
C13 C18 1.384(2) . ?
C13 C14 1.3921(19) . ?
C14 C15 1.388(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.498(2) . ?
C20 C25 1.3872(19) . ?
C20 C21 1.387(2) . ?
C21 C22 1.385(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.372(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.374(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.382(2) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 108.47(11) . . ?
C8 N1 C26 125.82(12) . . ?
C1 N1 C26 125.71(13) . . ?
N1 C1 C2 129.38(14) . . ?
N1 C1 C6 109.28(12) . . ?
C2 C1 C6 121.30(13) . . ?
C3 C2 C1 117.70(15) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 121.72(14) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 120.91(15) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 118.48(15) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 119.86(13) . . ?
C5 C6 C7 133.57(13) . . ?
C1 C6 C7 106.45(11) . . ?
C12 C7 C8 119.20(12) . . ?
C12 C7 C6 134.22(12) . . ?
C8 C7 C6 106.56(12) . . ?
N1 C8 C9 129.21(12) . . ?
N1 C8 C7 109.21(11) . . ?
C9 C8 C7 121.57(12) . . ?
C10 C9 C8 119.25(12) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 119.34(12) . . ?
C9 C10 C13 118.85(11) . . ?
C11 C10 C13 121.76(12) . . ?
C12 C11 C10 120.64(13) . . ?
C12 C11 C19 116.03(11) . . ?
C10 C11 C19 123.26(12) . . ?
C7 C12 C11 119.93(12) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C18 C13 C14 117.78(12) . . ?
C18 C13 C10 121.70(12) . . ?
C14 C13 C10 120.50(12) . . ?
C15 C14 C13 120.80(14) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 120.35(15) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.70(14) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 120.13(14) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 121.25(13) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
O1 C19 C11 120.69(13) . . ?
O1 C19 C20 119.98(13) . . ?
C11 C19 C20 119.10(11) . . ?
C25 C20 C21 119.19(14) . . ?
C25 C20 C19 119.53(12) . . ?
C21 C20 C19 121.11(13) . . ?
C22 C21 C20 119.83(15) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C23 C22 C21 120.54(16) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 119.95(16) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C25 120.11(16) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C20 120.37(14) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?
N1 C26 H26A 109.5 . . ?
N1 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N1 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C8 N1 C1 C2 -176.18(14) . . . . ?
C26 N1 C1 C2 4.7(3) . . . . ?
C8 N1 C1 C6 1.53(15) . . . . ?
C26 N1 C1 C6 -177.58(15) . . . . ?
N1 C1 C2 C3 175.44(14) . . . . ?
C6 C1 C2 C3 -2.0(2) . . . . ?
C1 C2 C3 C4 1.9(2) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C4 C5 C6 C7 -175.29(14) . . . . ?
N1 C1 C6 C5 -176.90(12) . . . . ?
C2 C1 C6 C5 1.0(2) . . . . ?
N1 C1 C6 C7 -0.36(15) . . . . ?
C2 C1 C6 C7 177.57(13) . . . . ?
C5 C6 C7 C12 -3.2(3) . . . . ?
C1 C6 C7 C12 -179.03(14) . . . . ?
C5 C6 C7 C8 174.95(15) . . . . ?
C1 C6 C7 C8 -0.91(14) . . . . ?
C1 N1 C8 C9 176.50(14) . . . . ?
C26 N1 C8 C9 -4.4(2) . . . . ?
C1 N1 C8 C7 -2.12(15) . . . . ?
C26 N1 C8 C7 176.99(15) . . . . ?
C12 C7 C8 N1 -179.68(11) . . . . ?
C6 C7 C8 N1 1.87(15) . . . . ?
C12 C7 C8 C9 1.6(2) . . . . ?
C6 C7 C8 C9 -176.87(12) . . . . ?
N1 C8 C9 C10 -177.54(13) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
C8 C9 C10 C11 -2.2(2) . . . . ?
C8 C9 C10 C13 -179.67(12) . . . . ?
C9 C10 C11 C12 1.0(2) . . . . ?
C13 C10 C11 C12 178.39(11) . . . . ?
C9 C10 C11 C19 177.70(12) . . . . ?
C13 C10 C11 C19 -4.9(2) . . . . ?
C8 C7 C12 C11 -2.79(19) . . . . ?
C6 C7 C12 C11 175.15(13) . . . . ?
C10 C11 C12 C7 1.6(2) . . . . ?
C19 C11 C12 C7 -175.41(12) . . . . ?
C9 C10 C13 C18 132.31(14) . . . . ?
C11 C10 C13 C18 -45.1(2) . . . . ?
C9 C10 C13 C14 -45.76(19) . . . . ?
C11 C10 C13 C14 136.80(15) . . . . ?
C18 C13 C14 C15 0.6(2) . . . . ?
C10 C13 C14 C15 178.73(14) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C14 C13 C18 C17 -0.1(2) . . . . ?
C10 C13 C18 C17 -178.19(14) . . . . ?
C16 C17 C18 C13 -0.6(2) . . . . ?
C12 C11 C19 O1 -53.07(18) . . . . ?
C10 C11 C19 O1 130.05(15) . . . . ?
C12 C11 C19 C20 121.50(13) . . . . ?
C10 C11 C19 C20 -55.38(18) . . . . ?
O1 C19 C20 C25 -23.68(19) . . . . ?
C11 C19 C20 C25 161.72(12) . . . . ?
O1 C19 C20 C21 151.56(14) . . . . ?
C11 C19 C20 C21 -23.04(19) . . . . ?
C25 C20 C21 C22 0.8(2) . . . . ?
C19 C20 C21 C22 -174.41(13) . . . . ?
C20 C21 C22 C23 -1.0(2) . . . . ?
C21 C22 C23 C24 0.0(3) . . . . ?
C22 C23 C24 C25 1.1(3) . . . . ?
C23 C24 C25 C20 -1.3(2) . . . . ?
C21 C20 C25 C24 0.3(2) . . . . ?
C19 C20 C25 C24 175.64(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.068
_database_code_depnum_ccdc_archive 'CCDC 973031'
