# 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_d



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C22 H17 N O'

_chemical_formula_weight         311.37



loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source








C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Orthorhombic

_symmetry_space_group_name_H-M   Pna2(1)



loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   6.3212(16)

_cell_length_b                   7.4318(19)

_cell_length_c                   33.967(9)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     1595.7(7)

_cell_formula_units_Z            4

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    517

_cell_measurement_theta_min      3.28

_cell_measurement_theta_max      21.33



_exptl_crystal_description       block

_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.41

_exptl_crystal_size_mid          0.32

_exptl_crystal_size_min          0.26

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.296

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             656

_exptl_absorpt_coefficient_mu    0.079

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9683

_exptl_absorpt_correction_T_max  0.9797

_exptl_absorpt_process_details   sadabs



_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  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_interval_time  0

_diffrn_standards_decay_%        0

_diffrn_reflns_number            4861

_diffrn_reflns_av_R_equivalents  0.0584

_diffrn_reflns_av_sigmaI/netI    0.0502

_diffrn_reflns_limit_h_min       -6

_diffrn_reflns_limit_h_max       7

_diffrn_reflns_limit_k_min       -9

_diffrn_reflns_limit_k_max       8

_diffrn_reflns_limit_l_min       -13

_diffrn_reflns_limit_l_max       41

_diffrn_reflns_theta_min         2.81

_diffrn_reflns_theta_max         25.50

_reflns_number_total             1796

_reflns_number_gt                1104

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_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)+(0.0443P)²+0.1634P] 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_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   0(3)

_refine_ls_number_reflns         1796

_refine_ls_number_parameters     218

_refine_ls_number_restraints     1

_refine_ls_R_factor_all          0.0939

_refine_ls_R_factor_gt           0.0478

_refine_ls_wR_factor_ref         0.1132

_refine_ls_wR_factor_gt          0.0928

_refine_ls_goodness_of_fit_ref   1.000

_refine_ls_restrained_S_all      1.000

_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









































N1 N 0.5606(5) 1.0325(4) -0.01542(12) 0.0431(9) Uani 1 1 d . . .
O1 O -0.0309(6) 1.0082(4) 0.25376(11) 0.0600(10) Uani 1 1 d . . .
C1 C -0.2165(8) 0.9061(8) 0.26411(17) 0.0811(18) Uani 1 1 d . . .
H1A H -0.3360 0.9510 0.2497 0.122 Uiso 1 1 calc R . .
H1B H -0.2428 0.9176 0.2918 0.122 Uiso 1 1 calc R . .
H1C H -0.1944 0.7817 0.2577 0.122 Uiso 1 1 calc R . .
C2 C 0.0411(7) 0.9993(6) 0.21545(14) 0.0455(13) Uani 1 1 d . . .
C3 C -0.0552(7) 0.9026(6) 0.18614(16) 0.0492(12) Uani 1 1 d . . .
H3 H -0.1768 0.8363 0.1914 0.059 Uiso 1 1 calc R . .
C4 C 0.2124(7) 1.0025(6) 0.13921(14) 0.0385(11) Uani 1 1 d . . .
C5 C 0.3056(7) 1.0975(6) 0.17023(13) 0.0472(13) Uani 1 1 d . . .
H5 H 0.4280 1.1633 0.1654 0.057 Uiso 1 1 calc R . .
C6 C 0.2221(7) 1.0970(6) 0.20764(14) 0.0482(13) Uani 1 1 d . . .
H6 H 0.2873 1.1623 0.2276 0.058 Uiso 1 1 calc R . .
C7 C 0.0308(7) 0.9046(6) 0.14849(14) 0.0480(13) Uani 1 1 d . . .
H7 H -0.0352 0.8384 0.1288 0.058 Uiso 1 1 calc R . .
C8 C 0.1810(7) 0.9582(5) 0.06657(14) 0.0438(13) Uani 1 1 d . . .
H8 H 0.0432 0.9184 0.0706 0.053 Uiso 1 1 calc R . .
C9 C 0.4431(8) 0.9882(6) -0.04640(15) 0.0402(11) Uani 1 1 d . . .
C10 C 0.1383(6) 0.9265(5) -0.00622(14) 0.0465(12) Uani 1 1 d . . .
H10 H -0.0026 0.8925 -0.0037 0.056 Uiso 1 1 calc R . .
C11 C 0.2278(7) 0.9363(6) -0.04235(14) 0.0466(13) Uani 1 1 d . . .
H11 H 0.1482 0.9091 -0.0646 0.056 Uiso 1 1 calc R . .
C12 C 0.2594(7) 0.9679(6) 0.02774(14) 0.0392(11) Uani 1 1 d . . .
C13 C 0.4715(8) 1.0253(7) 0.02090(13) 0.0432(13) Uani 1 1 d . . .
C14 C 0.3008(7) 1.0055(6) 0.09875(15) 0.0384(11) Uani 1 1 d . . .
C15 C 0.5131(7) 1.0625(6) 0.09105(14) 0.0461(13) Uani 1 1 d . . .
H15 H 0.5992 1.0935 0.1122 0.055 Uiso 1 1 calc R . .
C16 C 0.5934(7) 1.0730(5) 0.05418(15) 0.0441(12) Uani 1 1 d . . .
H16 H 0.7317 1.1125 0.0507 0.053 Uiso 1 1 calc R . .
C17 C 0.4617(7) 0.9051(6) -0.11781(14) 0.0481(12) Uani 1 1 d . . .
H17 H 0.3378 0.8391 -0.1148 0.058 Uiso 1 1 calc R . .
C18 C 0.5450(7) 0.9932(6) -0.08566(14) 0.0441(12) Uani 1 1 d . . .
C19 C 0.5575(8) 0.9123(7) -0.15437(15) 0.0572(13) Uani 1 1 d . . .
H19 H 0.4967 0.8530 -0.1757 0.069 Uiso 1 1 calc R . .
C20 C 0.8317(8) 1.0931(7) -0.12725(16) 0.0562(14) Uani 1 1 d . . .
H20 H 0.9579 1.1560 -0.1302 0.067 Uiso 1 1 calc R . .
C21 C 0.7369(7) 1.0874(6) -0.09083(14) 0.0484(13) Uani 1 1 d . . .
H21 H 0.7993 1.1458 -0.0696 0.058 Uiso 1 1 calc R . .
C22 C 0.7452(8) 1.0081(7) -0.15938(16) 0.0576(14) Uani 1 1 d . . .
H22 H 0.8103 1.0145 -0.1839 0.069 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 C9 1.329(6) . ?
N1 C13 1.357(6) . ?
O1 C2 1.380(5) . ?
O1 C1 1.441(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.371(6) . ?
C2 C6 1.381(6) . ?
C3 C7 1.390(6) . ?
C3 H3 0.9300 . ?
C4 C7 1.395(6) . ?
C4 C5 1.399(6) . ?
C4 C14 1.484(5) . ?
C5 C6 1.376(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C14 1.376(6) . ?
C8 C12 1.411(6) . ?
C8 H8 0.9300 . ?
C9 C11 1.421(6) . ?
C9 C18 1.482(6) . ?
C10 C11 1.353(6) . ?
C10 C12 1.418(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.426(5) . ?
C13 C16 1.413(6) . ?
C14 C15 1.431(6) . ?
C15 C16 1.354(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.378(6) . ?
C17 C19 1.383(6) . ?
C17 H17 0.9300 . ?
C18 C21 1.411(6) . ?
C19 C22 1.394(6) . ?
C19 H19 0.9300 . ?
C20 C22 1.374(7) . ?
C20 C21 1.375(6) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag







































































C9 N1 C13 118.6(4) . . ?
C2 O1 C1 118.2(4) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 O1 124.3(4) . . ?
C3 C2 C6 120.3(5) . . ?
O1 C2 C6 115.4(4) . . ?
C2 C3 C7 119.3(4) . . ?
C2 C3 H3 120.4 . . ?
C7 C3 H3 120.4 . . ?
C7 C4 C5 116.1(5) . . ?
C7 C4 C14 121.8(4) . . ?
C5 C4 C14 122.1(4) . . ?
C6 C5 C4 122.2(4) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C2 119.8(5) . . ?
C5 C6 H6 120.1 . . ?
C2 C6 H6 120.1 . . ?
C3 C7 C4 122.4(4) . . ?
C3 C7 H7 118.8 . . ?
C4 C7 H7 118.8 . . ?
C14 C8 C12 122.4(4) . . ?
C14 C8 H8 118.8 . . ?
C12 C8 H8 118.8 . . ?
N1 C9 C11 121.7(5) . . ?
N1 C9 C18 117.6(4) . . ?
C11 C9 C18 120.7(4) . . ?
C11 C10 C12 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C12 C10 H10 120.0 . . ?
C10 C11 C9 120.2(5) . . ?
C10 C11 H11 119.9 . . ?
C9 C11 H11 119.9 . . ?
C8 C12 C10 124.0(4) . . ?
C8 C12 C13 119.9(4) . . ?
C10 C12 C13 116.1(4) . . ?
N1 C13 C16 119.4(4) . . ?
N1 C13 C12 123.4(4) . . ?
C16 C13 C12 117.2(4) . . ?
C8 C14 C15 116.5(4) . . ?
C8 C14 C4 121.6(4) . . ?
C15 C14 C4 121.8(4) . . ?
C16 C15 C14 122.5(4) . . ?
C16 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C15 C16 C13 121.4(4) . . ?
C15 C16 H16 119.3 . . ?
C13 C16 H16 119.3 . . ?
C18 C17 C19 121.7(5) . . ?
C18 C17 H17 119.1 . . ?
C19 C17 H17 119.1 . . ?
C17 C18 C21 117.7(5) . . ?
C17 C18 C9 122.4(4) . . ?
C21 C18 C9 119.9(4) . . ?
C17 C19 C22 120.1(5) . . ?
C17 C19 H19 119.9 . . ?
C22 C19 H19 119.9 . . ?
C22 C20 C21 121.8(5) . . ?
C22 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C20 C21 C18 120.1(5) . . ?
C20 C21 H21 119.9 . . ?
C18 C21 H21 119.9 . . ?
C20 C22 C19 118.5(5) . . ?
C20 C22 H22 120.8 . . ?
C19 C22 H22 120.8 . . ?



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


















































C1 O1 C2 C3 1.6(7) . . . . ?
C1 O1 C2 C6 -178.7(5) . . . . ?
O1 C2 C3 C7 179.5(4) . . . . ?
C6 C2 C3 C7 -0.3(7) . . . . ?
C7 C4 C5 C6 -0.8(7) . . . . ?
C14 C4 C5 C6 179.0(4) . . . . ?
C4 C5 C6 C2 0.4(7) . . . . ?
C3 C2 C6 C5 0.1(7) . . . . ?
O1 C2 C6 C5 -179.6(4) . . . . ?
C2 C3 C7 C4 -0.2(7) . . . . ?
C5 C4 C7 C3 0.7(6) . . . . ?
C14 C4 C7 C3 -179.2(4) . . . . ?
C13 N1 C9 C11 0.8(6) . . . . ?
C13 N1 C9 C18 -178.7(4) . . . . ?
C12 C10 C11 C9 0.0(7) . . . . ?
N1 C9 C11 C10 -1.7(7) . . . . ?
C18 C9 C11 C10 177.8(4) . . . . ?
C14 C8 C12 C10 -177.7(4) . . . . ?
C14 C8 C12 C13 1.2(6) . . . . ?
C11 C10 C12 C8 -178.8(4) . . . . ?
C11 C10 C12 C13 2.3(6) . . . . ?
C9 N1 C13 C16 -179.6(4) . . . . ?
C9 N1 C13 C12 1.7(6) . . . . ?
C8 C12 C13 N1 177.8(5) . . . . ?
C10 C12 C13 N1 -3.3(6) . . . . ?
C8 C12 C13 C16 -0.9(6) . . . . ?
C10 C12 C13 C16 178.0(5) . . . . ?
C12 C8 C14 C15 -1.2(6) . . . . ?
C12 C8 C14 C4 177.1(4) . . . . ?
C7 C4 C14 C8 19.1(7) . . . . ?
C5 C4 C14 C8 -160.7(4) . . . . ?
C7 C4 C14 C15 -162.7(4) . . . . ?
C5 C4 C14 C15 17.5(7) . . . . ?
C8 C14 C15 C16 1.1(7) . . . . ?
C4 C14 C15 C16 -177.2(4) . . . . ?
C14 C15 C16 C13 -0.9(7) . . . . ?
N1 C13 C16 C15 -177.9(4) . . . . ?
C12 C13 C16 C15 0.8(6) . . . . ?
C19 C17 C18 C21 -2.0(7) . . . . ?
C19 C17 C18 C9 179.4(4) . . . . ?
N1 C9 C18 C17 161.7(4) . . . . ?
C11 C9 C18 C17 -17.9(6) . . . . ?
N1 C9 C18 C21 -16.9(6) . . . . ?
C11 C9 C18 C21 163.6(5) . . . . ?
C18 C17 C19 C22 1.0(7) . . . . ?
C22 C20 C21 C18 -0.2(7) . . . . ?
C17 C18 C21 C20 1.6(7) . . . . ?
C9 C18 C21 C20 -179.8(4) . . . . ?
C21 C20 C22 C19 -0.8(7) . . . . ?
C17 C19 C22 C20 0.5(7) . . . . ?



_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        25.50

_diffrn_measured_fraction_theta_full 0.995

_refine_diff_density_max         0.147

_refine_diff_density_min         -0.156

_refine_diff_density_rms         0.037

_database_code_depnum_ccdc_archive 'CCDC 969896'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C25 H17 N'

_chemical_formula_weight         331.40



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'



_symmetry_cell_setting           Orthorhombic

_symmetry_space_group_name_H-M   Pbca



loop_

_symmetry_equiv_pos_as_xyz








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



_cell_length_a                   14.2395(19)

_cell_length_b                   7.5461(10)

_cell_length_c                   32.144(4)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     3454.0(8)

_cell_formula_units_Z            8

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    1374

_cell_measurement_theta_min      2.53

_cell_measurement_theta_max      19.37



_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.41

_exptl_crystal_size_mid          0.32

_exptl_crystal_size_min          0.26

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.275

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             1392

_exptl_absorpt_coefficient_mu    0.074

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9705

_exptl_absorpt_correction_T_max  0.9811

_exptl_absorpt_process_details   sadabs



_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  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_interval_time  0

_diffrn_standards_decay_%        0

_diffrn_reflns_number            19334

_diffrn_reflns_av_R_equivalents  0.0758

_diffrn_reflns_av_sigmaI/netI    0.0496

_diffrn_reflns_limit_h_min       -17

_diffrn_reflns_limit_h_max       17

_diffrn_reflns_limit_k_min       -9

_diffrn_reflns_limit_k_max       9

_diffrn_reflns_limit_l_min       -38

_diffrn_reflns_limit_l_max       38

_diffrn_reflns_theta_min         2.53

_diffrn_reflns_theta_max         25.50

_reflns_number_total             3217

_reflns_number_gt                1607

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_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)+(0.0512P)²+0.5984P] 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         3217

_refine_ls_number_parameters     235

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.1219

_refine_ls_R_factor_gt           0.0498

_refine_ls_wR_factor_ref         0.1364

_refine_ls_wR_factor_gt          0.1021

_refine_ls_goodness_of_fit_ref   0.993

_refine_ls_restrained_S_all      0.993

_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











































N1 N 0.59697(14) 0.0914(2) 0.32073(5) 0.0483(5) Uani 1 1 d . . .
C1 C 0.56306(16) 0.0861(3) 0.14452(7) 0.0476(6) Uani 1 1 d . . .
C2 C 0.59723(16) -0.0679(3) 0.12363(7) 0.0477(6) Uani 1 1 d . . .
C3 C 0.59800(18) -0.0718(4) 0.07947(7) 0.0575(7) Uani 1 1 d . . .
C4 C 0.5626(2) 0.0749(4) 0.05761(8) 0.0720(8) Uani 1 1 d . . .
H4 H 0.5628 0.0735 0.0287 0.086 Uiso 1 1 calc R . .
C5 C 0.5291(2) 0.2243(4) 0.12174(8) 0.0657(8) Uani 1 1 d . . .
H5 H 0.5061 0.3242 0.1353 0.079 Uiso 1 1 calc R . .
C6 C 0.6672(2) -0.3644(4) 0.08127(10) 0.0788(9) Uani 1 1 d . . .
H6 H 0.6913 -0.4624 0.0674 0.095 Uiso 1 1 calc R . .
C7 C 0.5282(2) 0.2183(4) 0.07784(9) 0.0768(9) Uani 1 1 d . . .
H7 H 0.5040 0.3130 0.0628 0.092 Uiso 1 1 calc R . .
C8 C 0.66459(19) -0.3623(4) 0.12457(9) 0.0722(8) Uani 1 1 d . . .
H8 H 0.6861 -0.4598 0.1395 0.087 Uiso 1 1 calc R . .
C9 C 0.63083(17) -0.2184(3) 0.14507(8) 0.0573(7) Uani 1 1 d . . .
H9 H 0.6298 -0.2189 0.1740 0.069 Uiso 1 1 calc R . .
C10 C 0.6346(2) -0.2241(4) 0.05939(9) 0.0710(8) Uani 1 1 d . . .
H10 H 0.6362 -0.2277 0.0305 0.085 Uiso 1 1 calc R . .
C11 C 0.58959(17) 0.0986(3) 0.27812(7) 0.0442(6) Uani 1 1 d . . .
C12 C 0.66249(16) 0.1630(3) 0.25243(7) 0.0451(6) Uani 1 1 d . . .
C13 C 0.50655(17) 0.0373(3) 0.25933(7) 0.0517(7) Uani 1 1 d . . .
H13 H 0.4571 -0.0019 0.2758 0.062 Uiso 1 1 calc R . .
C14 C 0.57027(17) 0.0962(3) 0.19089(7) 0.0467(6) Uani 1 1 d . . .
C15 C 0.65008(17) 0.1603(3) 0.20894(7) 0.0520(7) Uani 1 1 d . . .
H15 H 0.6978 0.2035 0.1920 0.062 Uiso 1 1 calc R . .
C16 C 0.49783(17) 0.0348(3) 0.21694(7) 0.0521(7) Uani 1 1 d . . .
H16 H 0.4428 -0.0084 0.2051 0.063 Uiso 1 1 calc R . .
C17 C 0.74512(18) 0.2227(3) 0.27230(7) 0.0547(7) Uani 1 1 d . . .
H17 H 0.7945 0.2681 0.2566 0.066 Uiso 1 1 calc R . .
C18 C 0.67649(18) 0.1464(3) 0.33797(7) 0.0478(6) Uani 1 1 d . . .
C19 C 0.75229(19) 0.2138(3) 0.31420(7) 0.0554(7) Uani 1 1 d . . .
H19 H 0.8068 0.2517 0.3274 0.067 Uiso 1 1 calc R . .
C20 C 0.68351(18) 0.1326(3) 0.38395(7) 0.0508(7) Uani 1 1 d . . .
C21 C 0.60405(19) 0.1456(3) 0.40862(7) 0.0593(7) Uani 1 1 d . . .
H21 H 0.5457 0.1616 0.3962 0.071 Uiso 1 1 calc R . .
C22 C 0.6104(2) 0.1353(4) 0.45131(8) 0.0714(8) Uani 1 1 d . . .
H22 H 0.5566 0.1460 0.4675 0.086 Uiso 1 1 calc R . .
C23 C 0.7693(2) 0.1048(3) 0.40334(8) 0.0659(8) Uani 1 1 d . . .
H23 H 0.8234 0.0940 0.3874 0.079 Uiso 1 1 calc R . .
C24 C 0.6956(2) 0.1094(4) 0.46999(9) 0.0792(9) Uani 1 1 d . . .
H24 H 0.6997 0.1030 0.4988 0.095 Uiso 1 1 calc R . .
C25 C 0.7750(2) 0.0929(4) 0.44614(8) 0.0781(9) Uani 1 1 d . . .
H25 H 0.8329 0.0737 0.4588 0.094 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 C18 1.327(3) . ?
N1 C11 1.375(3) . ?
C1 C5 1.363(3) . ?
C1 C2 1.428(3) . ?
C1 C14 1.496(3) . ?
C2 C9 1.412(3) . ?
C2 C3 1.420(3) . ?
C3 C4 1.404(4) . ?
C3 C10 1.417(4) . ?
C4 C7 1.354(4) . ?
C4 H4 0.9300 . ?
C5 C7 1.412(3) . ?
C5 H5 0.9300 . ?
C6 C10 1.353(4) . ?
C6 C8 1.392(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.358(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C13 1.406(3) . ?
C11 C12 1.413(3) . ?
C12 C15 1.409(3) . ?
C12 C17 1.413(3) . ?
C13 C16 1.368(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.365(3) . ?
C14 C16 1.407(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C19 1.352(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.417(3) . ?
C18 C20 1.485(3) . ?
C19 H19 0.9300 . ?
C20 C23 1.387(3) . ?
C20 C21 1.385(3) . ?
C21 C22 1.377(3) . ?
C21 H21 0.9300 . ?
C22 C24 1.368(4) . ?
C22 H22 0.9300 . ?
C23 C25 1.381(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.371(4) . ?
C24 H24 0.9300 . ?
C25 H25 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












































































C18 N1 C11 118.0(2) . . ?
C5 C1 C2 119.4(2) . . ?
C5 C1 C14 121.4(2) . . ?
C2 C1 C14 119.1(2) . . ?
C9 C2 C3 118.0(2) . . ?
C9 C2 C1 122.7(2) . . ?
C3 C2 C1 119.3(2) . . ?
C4 C3 C10 122.9(3) . . ?
C4 C3 C2 118.8(3) . . ?
C10 C3 C2 118.3(3) . . ?
C7 C4 C3 121.3(3) . . ?
C7 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C1 C5 C7 121.0(3) . . ?
C1 C5 H5 119.5 . . ?
C7 C5 H5 119.5 . . ?
C10 C6 C8 120.1(3) . . ?
C10 C6 H6 119.9 . . ?
C8 C6 H6 119.9 . . ?
C4 C7 C5 120.2(3) . . ?
C4 C7 H7 119.9 . . ?
C5 C7 H7 119.9 . . ?
C9 C8 C6 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C6 C8 H8 119.9 . . ?
C8 C9 C2 121.7(2) . . ?
C8 C9 H9 119.1 . . ?
C2 C9 H9 119.1 . . ?
C6 C10 C3 121.6(3) . . ?
C6 C10 H10 119.2 . . ?
C3 C10 H10 119.2 . . ?
N1 C11 C13 118.6(2) . . ?
N1 C11 C12 122.7(2) . . ?
C13 C11 C12 118.7(2) . . ?
C15 C12 C17 123.9(2) . . ?
C15 C12 C11 118.9(2) . . ?
C17 C12 C11 117.2(2) . . ?
C16 C13 C11 120.6(2) . . ?
C16 C13 H13 119.7 . . ?
C11 C13 H13 119.7 . . ?
C15 C14 C16 118.3(2) . . ?
C15 C14 C1 119.9(2) . . ?
C16 C14 C1 121.7(2) . . ?
C14 C15 C12 122.1(2) . . ?
C14 C15 H15 118.9 . . ?
C12 C15 H15 118.9 . . ?
C13 C16 C14 121.4(2) . . ?
C13 C16 H16 119.3 . . ?
C14 C16 H16 119.3 . . ?
C19 C17 C12 119.8(2) . . ?
C19 C17 H17 120.1 . . ?
C12 C17 H17 120.1 . . ?
N1 C18 C19 122.5(2) . . ?
N1 C18 C20 116.8(2) . . ?
C19 C18 C20 120.7(2) . . ?
C17 C19 C18 119.8(2) . . ?
C17 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C23 C20 C21 118.2(2) . . ?
C23 C20 C18 121.1(2) . . ?
C21 C20 C18 120.7(2) . . ?
C22 C21 C20 120.8(3) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C24 C22 C21 120.3(3) . . ?
C24 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C25 C23 C20 120.6(3) . . ?
C25 C23 H23 119.7 . . ?
C20 C23 H23 119.7 . . ?
C22 C24 C25 119.9(3) . . ?
C22 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C23 120.1(3) . . ?
C24 C25 H25 119.9 . . ?
C23 C25 H25 119.9 . . ?



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



























































C5 C1 C2 C9 -178.1(2) . . . . ?
C14 C1 C2 C9 5.3(4) . . . . ?
C5 C1 C2 C3 2.0(4) . . . . ?
C14 C1 C2 C3 -174.6(2) . . . . ?
C9 C2 C3 C4 178.4(2) . . . . ?
C1 C2 C3 C4 -1.7(4) . . . . ?
C9 C2 C3 C10 -1.6(4) . . . . ?
C1 C2 C3 C10 178.3(2) . . . . ?
C10 C3 C4 C7 -180.0(3) . . . . ?
C2 C3 C4 C7 0.0(4) . . . . ?
C2 C1 C5 C7 -0.8(4) . . . . ?
C14 C1 C5 C7 175.8(2) . . . . ?
C3 C4 C7 C5 1.3(5) . . . . ?
C1 C5 C7 C4 -0.9(5) . . . . ?
C10 C6 C8 C9 -1.1(4) . . . . ?
C6 C8 C9 C2 0.3(4) . . . . ?
C3 C2 C9 C8 1.1(4) . . . . ?
C1 C2 C9 C8 -178.8(2) . . . . ?
C8 C6 C10 C3 0.6(5) . . . . ?
C4 C3 C10 C6 -179.2(3) . . . . ?
C2 C3 C10 C6 0.8(4) . . . . ?
C18 N1 C11 C13 178.7(2) . . . . ?
C18 N1 C11 C12 -0.5(3) . . . . ?
N1 C11 C12 C15 178.0(2) . . . . ?
C13 C11 C12 C15 -1.2(3) . . . . ?
N1 C11 C12 C17 -0.5(3) . . . . ?
C13 C11 C12 C17 -179.7(2) . . . . ?
N1 C11 C13 C16 -177.1(2) . . . . ?
C12 C11 C13 C16 2.1(4) . . . . ?
C5 C1 C14 C15 -89.5(3) . . . . ?
C2 C1 C14 C15 87.1(3) . . . . ?
C5 C1 C14 C16 93.0(3) . . . . ?
C2 C1 C14 C16 -90.5(3) . . . . ?
C16 C14 C15 C12 1.4(4) . . . . ?
C1 C14 C15 C12 -176.3(2) . . . . ?
C17 C12 C15 C14 177.9(2) . . . . ?
C11 C12 C15 C14 -0.5(4) . . . . ?
C11 C13 C16 C14 -1.2(4) . . . . ?
C15 C14 C16 C13 -0.5(4) . . . . ?
C1 C14 C16 C13 177.1(2) . . . . ?
C15 C12 C17 C19 -177.3(2) . . . . ?
C11 C12 C17 C19 1.1(3) . . . . ?
C11 N1 C18 C19 0.9(3) . . . . ?
C11 N1 C18 C20 -178.38(19) . . . . ?
C12 C17 C19 C18 -0.7(4) . . . . ?
N1 C18 C19 C17 -0.3(4) . . . . ?
C20 C18 C19 C17 178.9(2) . . . . ?
N1 C18 C20 C23 149.5(2) . . . . ?
C19 C18 C20 C23 -29.8(3) . . . . ?
N1 C18 C20 C21 -29.9(3) . . . . ?
C19 C18 C20 C21 150.7(2) . . . . ?
C23 C20 C21 C22 1.5(4) . . . . ?
C18 C20 C21 C22 -179.1(2) . . . . ?
C20 C21 C22 C24 -0.9(4) . . . . ?
C21 C20 C23 C25 -0.8(4) . . . . ?
C18 C20 C23 C25 179.7(2) . . . . ?
C21 C22 C24 C25 -0.3(5) . . . . ?
C22 C24 C25 C23 0.9(5) . . . . ?
C20 C23 C25 C24 -0.3(4) . . . . ?



_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        25.50

_diffrn_measured_fraction_theta_full 0.999

_refine_diff_density_max         0.122

_refine_diff_density_min         -0.179

_refine_diff_density_rms         0.037

_database_code_depnum_ccdc_archive 'CCDC 969897'
#######################################################################
#
#                 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_ddd



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C21 H14 F N'

_chemical_formula_weight         299.33



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'
F F 0.0171 0.0103 '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                   15.95(2)

_cell_length_b                   7.413(10)

_cell_length_c                   6.299(9)

_cell_angle_alpha                90.00

_cell_angle_beta                 94.011(18)

_cell_angle_gamma                90.00

_cell_volume                     742.9(17)

_cell_formula_units_Z            2

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    563

_cell_measurement_theta_min      2.56

_cell_measurement_theta_max      22.15



_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.34

_exptl_crystal_size_mid          0.25

_exptl_crystal_size_min          0.21

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.338

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             312

_exptl_absorpt_coefficient_mu    0.087

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9712

_exptl_absorpt_correction_T_max  0.9821

_exptl_absorpt_process_details   sadabs



_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  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            3442

_diffrn_reflns_av_R_equivalents  0.0512

_diffrn_reflns_av_sigmaI/netI    0.0723

_diffrn_reflns_limit_h_min       -19

_diffrn_reflns_limit_h_max       19

_diffrn_reflns_limit_k_min       -8

_diffrn_reflns_limit_k_max       8

_diffrn_reflns_limit_l_min       -7

_diffrn_reflns_limit_l_max       5

_diffrn_reflns_theta_min         2.56

_diffrn_reflns_theta_max         25.49

_reflns_number_total             1369

_reflns_number_gt                573

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_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)+(0.0502P)²+0.5064P] 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         1369

_refine_ls_number_parameters     112

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.1626

_refine_ls_R_factor_gt           0.0663

_refine_ls_wR_factor_ref         0.1912

_refine_ls_wR_factor_gt          0.1535

_refine_ls_goodness_of_fit_ref   1.048

_refine_ls_restrained_S_all      1.048

_refine_ls_shift/su_max          0.003

_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





















C8 C 0.4206(10) 0.543(2) 0.686(3) 0.0494(18) Uani 0.50 1 d P A 1
H8 H 0.4157 0.5836 0.8243 0.059 Uiso 0.50 1 calc PR A 1
N1 N 0.4037(8) 0.5321(19) 0.657(2) 0.0494(18) Uani 0.50 1 d P A 2
C1 C 0.1008(3) 0.5088(6) 0.7635(8) 0.0731(13) Uani 1 1 d . . .
H1 H 0.0470 0.5147 0.8113 0.088 Uiso 0.50 1 calc PR B 1
F1 F 0.0222(3) 0.4960(8) 0.8229(9) 0.1033(19) Uani 0.50 1 d P C 2
C2 C 0.1645(3) 0.5945(6) 0.8723(7) 0.0723(13) Uani 1 1 d . C .
H2 H 0.1548 0.6574 0.9959 0.087 Uiso 1 1 calc R . .
C3 C 0.2449(3) 0.5891(5) 0.8003(6) 0.0662(12) Uani 1 1 d . . .
H3 H 0.2886 0.6486 0.8766 0.079 Uiso 1 1 calc R C .
C4 C 0.2608(2) 0.4968(5) 0.6174(6) 0.0541(11) Uani 1 1 d . A .
C5 C 0.1938(3) 0.4077(5) 0.5116(6) 0.0615(12) Uani 1 1 d . . .
H5 H 0.2029 0.3426 0.3891 0.074 Uiso 1 1 calc R C .
C6 C 0.1143(3) 0.4130(6) 0.5829(7) 0.0743(14) Uani 1 1 d . C .
H6 H 0.0702 0.3523 0.5095 0.089 Uiso 1 1 calc R . .
C7 C 0.3456(2) 0.4898(5) 0.5387(6) 0.0527(11) Uani 1 1 d . . .
C9 C 0.4921(3) 0.5285(5) 0.6028(6) 0.0574(11) Uani 1 1 d . . .
C10 C 0.5626(3) 0.5737(5) 0.7399(6) 0.0684(13) Uani 1 1 d . . .
H10 H 0.5554 0.6104 0.8787 0.082 Uiso 1 1 calc R . .
C11 C 0.3594(3) 0.4361(5) 0.3298(6) 0.0650(13) Uani 1 1 d . . .
H11 H 0.3135 0.4065 0.2371 0.078 Uiso 1 1 calc R . .






_geom_special_details            
;

 All esds (except the esd in the dihedral angle between two l.s. planes)

 are estimated using the full covariance matrix.  The cell esds are taken

 into account individually in the estimation of esds in distances, angles

 and torsion angles; correlations between esds in cell parameters are only

 used when they are defined by crystal symmetry.  An approximate (isotropic)

 treatment of cell esds is used for estimating esds involving l.s. planes.

;



loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag

























C8 C9 1.292(17) . ?
C8 C7 1.514(15) . ?
C8 H8 0.9300 . ?
N1 C7 1.188(12) . ?
N1 C9 1.473(14) . ?
C1 F1 1.337(6) . ?
C1 C2 1.344(6) . ?
C1 C6 1.371(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.390(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(5) . ?
C4 C7 1.474(5) . ?
C5 C6 1.375(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.407(5) . ?
C9 C9 1.402(7) 3_666 ?
C9 C10 1.410(5) . ?
C10 C11 1.350(5) 3_666 ?
C10 H10 0.9300 . ?
C11 C10 1.350(5) 3_666 ?
C11 H11 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











































C9 C8 C7 114.3(12) . . ?
C9 C8 H8 122.9 . . ?
C7 C8 H8 122.9 . . ?
C7 N1 C9 124.6(11) . . ?
F1 C1 C2 125.5(5) . . ?
F1 C1 C6 113.6(5) . . ?
C2 C1 C6 120.7(4) . . ?
F1 C1 H1 7.2 . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 120.1(4) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 117.2(4) . . ?
C3 C4 C7 121.7(4) . . ?
C5 C4 C7 121.1(4) . . ?
C6 C5 C4 121.8(4) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C1 C6 C5 119.2(4) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N1 C7 C11 119.6(8) . . ?
N1 C7 C4 118.3(8) . . ?
C11 C7 C4 122.1(4) . . ?
N1 C7 C8 1.0(13) . . ?
C11 C7 C8 118.6(7) . . ?
C4 C7 C8 119.3(7) . . ?
C8 C9 C9 128.4(9) . 3_666 ?
C8 C9 C10 114.9(8) . . ?
C9 C9 C10 116.8(5) 3_666 . ?
C8 C9 N1 11.3(11) . . ?
C9 C9 N1 117.1(7) 3_666 . ?
C10 C9 N1 126.2(6) . . ?
C11 C10 C9 120.1(4) 3_666 . ?
C11 C10 H10 119.9 3_666 . ?
C9 C10 H10 119.9 . . ?
C10 C11 C7 121.8(4) 3_666 . ?
C10 C11 H11 119.1 3_666 . ?
C7 C11 H11 119.1 . . ?



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


































F1 C1 C2 C3 176.1(5) . . . . ?
C6 C1 C2 C3 1.1(7) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C3 C4 C5 -1.1(6) . . . . ?
C2 C3 C4 C7 180.0(4) . . . . ?
C3 C4 C5 C6 1.1(6) . . . . ?
C7 C4 C5 C6 -180.0(4) . . . . ?
F1 C1 C6 C5 -176.7(5) . . . . ?
C2 C1 C6 C5 -1.1(7) . . . . ?
C4 C5 C6 C1 0.0(6) . . . . ?
C9 N1 C7 C11 -1.7(16) . . . . ?
C9 N1 C7 C4 178.7(8) . . . . ?
C9 N1 C7 C8 -7(75) . . . . ?
C3 C4 C7 N1 15.6(9) . . . . ?
C5 C4 C7 N1 -163.3(8) . . . . ?
C3 C4 C7 C11 -164.0(4) . . . . ?
C5 C4 C7 C11 17.1(6) . . . . ?
C3 C4 C7 C8 15.5(9) . . . . ?
C5 C4 C7 C8 -163.4(8) . . . . ?
C9 C8 C7 N1 172(77) . . . . ?
C9 C8 C7 C11 -2.0(15) . . . . ?
C9 C8 C7 C4 178.5(8) . . . . ?
C7 C8 C9 C9 0.5(17) . . . 3_666 ?
C7 C8 C9 C10 -178.5(8) . . . . ?
C7 C8 C9 N1 -1(5) . . . . ?
C7 N1 C9 C8 179(8) . . . . ?
C7 N1 C9 C9 0.2(16) . . . 3_666 ?
C7 N1 C9 C10 -178.5(9) . . . . ?
C8 C9 C10 C11 -179.8(9) . . . 3_666 ?
C9 C9 C10 C11 1.1(7) 3_666 . . 3_666 ?
N1 C9 C10 C11 179.7(8) . . . 3_666 ?
N1 C7 C11 C10 1.8(10) . . . 3_666 ?
C4 C7 C11 C10 -178.6(4) . . . 3_666 ?
C8 C7 C11 C10 1.9(9) . . . 3_666 ?



_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        25.49

_diffrn_measured_fraction_theta_full 0.995

_refine_diff_density_max         0.124

_refine_diff_density_min         -0.167

_refine_diff_density_rms         0.038

_database_code_depnum_ccdc_archive 'CCDC 969898'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C29 H23 N O2'

_chemical_formula_weight         417.48



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           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                   12.397(5)

_cell_length_b                   13.109(5)

_cell_length_c                   13.546(5)

_cell_angle_alpha                90.00

_cell_angle_beta                 93.129(5)

_cell_angle_gamma                90.00

_cell_volume                     2198.2(14)

_cell_formula_units_Z            4

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    2243

_cell_measurement_theta_min      2.67

_cell_measurement_theta_max      22.58



_exptl_crystal_description       block

_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.49

_exptl_crystal_size_mid          0.33

_exptl_crystal_size_min          0.30

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.261

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             880

_exptl_absorpt_coefficient_mu    0.079

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9625

_exptl_absorpt_correction_T_max  0.9768

_exptl_absorpt_process_details   sadabs



_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  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            11771

_diffrn_reflns_av_R_equivalents  0.0292

_diffrn_reflns_av_sigmaI/netI    0.0322

_diffrn_reflns_limit_h_min       -14

_diffrn_reflns_limit_h_max       15

_diffrn_reflns_limit_k_min       -15

_diffrn_reflns_limit_k_max       15

_diffrn_reflns_limit_l_min       -13

_diffrn_reflns_limit_l_max       16

_diffrn_reflns_theta_min         2.67

_diffrn_reflns_theta_max         25.50

_reflns_number_total             4014

_reflns_number_gt                2499

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_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)+(0.0569P)²+0.5450P] 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         4014

_refine_ls_number_parameters     291

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0860

_refine_ls_R_factor_gt           0.0494

_refine_ls_wR_factor_ref         0.1421

_refine_ls_wR_factor_gt          0.1221

_refine_ls_goodness_of_fit_ref   1.035

_refine_ls_restrained_S_all      1.035

_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 0.33250(17) 0.51057(18) -0.01114(18) 0.0566(6) Uani 1 1 d . . .
C2 C 0.3839(2) 0.45161(18) -0.08176(19) 0.0653(7) Uani 1 1 d . . .
H2 H 0.3997 0.4796 -0.1424 0.078 Uiso 1 1 calc R . .
C3 C 0.4100(2) 0.3527(2) -0.05971(19) 0.0718(7) Uani 1 1 d . . .
H3 H 0.4417 0.3120 -0.1064 0.086 Uiso 1 1 calc R . .
C4 C 0.38903(16) 0.31214(18) 0.03395(17) 0.0544(6) Uani 1 1 d . . .
C5 C 0.41706(17) 0.21013(18) 0.06261(19) 0.0616(6) Uani 1 1 d . . .
H5 H 0.4470 0.1665 0.0174 0.074 Uiso 1 1 calc R . .
C6 C 0.39997(16) 0.17607(18) 0.15665(17) 0.0544(6) Uani 1 1 d . . .
C7 C 0.35247(17) 0.24428(17) 0.22195(18) 0.0580(6) Uani 1 1 d . . .
H7 H 0.3407 0.2225 0.2858 0.070 Uiso 1 1 calc R . .
C8 C 0.32313(18) 0.34079(18) 0.19501(18) 0.0591(6) Uani 1 1 d . . .
H8 H 0.2905 0.3829 0.2399 0.071 Uiso 1 1 calc R . .
C9 C 0.34159(16) 0.37724(17) 0.10056(18) 0.0537(6) Uani 1 1 d . . .
C10 C 0.42739(17) 0.06914(18) 0.18655(18) 0.0566(6) Uani 1 1 d . . .
C11 C 0.3921(2) -0.0123(2) 0.1281(2) 0.0686(7) Uani 1 1 d . . .
H11 H 0.3511 0.0008 0.0700 0.082 Uiso 1 1 calc R . .
C12 C 0.4157(2) -0.1123(2) 0.1530(2) 0.0800(8) Uani 1 1 d . . .
H12 H 0.3911 -0.1655 0.1123 0.096 Uiso 1 1 calc R . .
C13 C 0.4761(2) -0.1319(2) 0.2390(3) 0.0850(9) Uani 1 1 d . . .
H13 H 0.4919 -0.1990 0.2569 0.102 Uiso 1 1 calc R . .
C14 C 0.5134(2) -0.0535(2) 0.2987(2) 0.0744(8) Uani 1 1 d . . .
H14 H 0.5553 -0.0676 0.3561 0.089 Uiso 1 1 calc R . .
C15 C 0.48856(18) 0.04668(18) 0.27361(19) 0.0613(6) Uani 1 1 d . . .
C16 C 0.5894(3) 0.1126(2) 0.4166(2) 0.1097(12) Uani 1 1 d . . .
H16A H 0.5521 0.0695 0.4607 0.165 Uiso 1 1 calc R . .
H16B H 0.6055 0.1767 0.4482 0.165 Uiso 1 1 calc R . .
H16C H 0.6555 0.0802 0.3998 0.165 Uiso 1 1 calc R . .
C17 C 0.29395(17) 0.61565(16) -0.03585(17) 0.0530(6) Uani 1 1 d . . .
C18 C 0.33703(18) 0.67348(19) -0.10819(19) 0.0631(6) Uani 1 1 d . . .
H18 H 0.3944 0.6477 -0.1420 0.076 Uiso 1 1 calc R . .
C19 C 0.29760(18) 0.76812(18) -0.13163(18) 0.0624(6) Uani 1 1 d . . .
H19 H 0.3288 0.8055 -0.1810 0.075 Uiso 1 1 calc R . .
C20 C 0.21216(16) 0.80988(17) -0.08366(16) 0.0520(6) Uani 1 1 d . . .
C21 C 0.16838(18) 0.75293(16) -0.00897(17) 0.0571(6) Uani 1 1 d . . .
H21 H 0.1114 0.7794 0.0249 0.069 Uiso 1 1 calc R . .
C22 C 0.20886(18) 0.65737(17) 0.01540(18) 0.0589(6) Uani 1 1 d . . .
H22 H 0.1795 0.6204 0.0661 0.071 Uiso 1 1 calc R . .
C23 C 0.17277(18) 0.91399(17) -0.10926(16) 0.0536(6) Uani 1 1 d . . .
C24 C 0.06248(19) 0.93779(17) -0.11966(17) 0.0579(6) Uani 1 1 d . . .
C25 C 0.0291(2) 1.03634(19) -0.14104(19) 0.0720(7) Uani 1 1 d . . .
H25 H -0.0443 1.0514 -0.1470 0.086 Uiso 1 1 calc R . .
C26 C 0.1036(3) 1.1123(2) -0.1535(2) 0.0829(8) Uani 1 1 d . . .
H26 H 0.0803 1.1785 -0.1673 0.099 Uiso 1 1 calc R . .
C27 C 0.2112(3) 1.0913(2) -0.1459(2) 0.0818(8) Uani 1 1 d . . .
H27 H 0.2613 1.1428 -0.1551 0.098 Uiso 1 1 calc R . .
C28 C 0.2458(2) 0.99325(19) -0.12434(18) 0.0674(7) Uani 1 1 d . . .
H28 H 0.3195 0.9795 -0.1197 0.081 Uiso 1 1 calc R . .
C29 C -0.1200(2) 0.8778(2) -0.1239(3) 0.0964(10) Uani 1 1 d . . .
H29A H -0.1412 0.9268 -0.0760 0.145 Uiso 1 1 calc R . .
H29B H -0.1593 0.8155 -0.1160 0.145 Uiso 1 1 calc R . .
H29C H -0.1355 0.9042 -0.1893 0.145 Uiso 1 1 calc R . .
N1 N 0.31139(14) 0.47680(14) 0.07612(15) 0.0547(5) Uani 1 1 d . . .
O1 O 0.52298(14) 0.12932(13) 0.32907(14) 0.0769(5) Uani 1 1 d . . .
O2 O -0.00690(12) 0.85827(12) -0.10992(14) 0.0738(5) Uani 1 1 d . . .






_geom_special_details            
;

 All esds (except the esd in the dihedral angle between two l.s. planes)

 are estimated using the full covariance matrix.  The cell esds are taken

 into account individually in the estimation of esds in distances, angles

 and torsion angles; correlations between esds in cell parameters are only

 used when they are defined by crystal symmetry.  An approximate (isotropic)

 treatment of cell esds is used for estimating esds involving l.s. planes.

;



loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag



























































C1 N1 1.302(3) . ?
C1 C2 1.409(3) . ?
C1 C17 1.490(3) . ?
C2 C3 1.365(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.413(3) . ?
C3 H3 0.9300 . ?
C4 C9 1.395(3) . ?
C4 C5 1.430(3) . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.409(3) . ?
C6 C10 1.493(3) . ?
C7 C8 1.361(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.396(3) . ?
C8 H8 0.9300 . ?
C9 N1 1.393(3) . ?
C10 C11 1.386(3) . ?
C10 C15 1.398(3) . ?
C11 C12 1.381(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(3) . ?
C14 H14 0.9300 . ?
C15 O1 1.373(3) . ?
C16 O1 1.423(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.370(3) . ?
C17 C22 1.405(3) . ?
C18 C19 1.364(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.391(3) . ?
C20 C23 1.484(3) . ?
C21 C22 1.383(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C28 1.400(3) . ?
C23 C24 1.402(3) . ?
C24 O2 1.362(3) . ?
C24 C25 1.383(3) . ?
C25 C26 1.375(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.361(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.381(3) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 O2 1.428(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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
































































































N1 C1 C2 123.4(2) . . ?
N1 C1 C17 116.1(2) . . ?
C2 C1 C17 120.4(2) . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C9 C4 C3 117.1(2) . . ?
C9 C4 C5 120.1(2) . . ?
C3 C4 C5 122.8(2) . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 117.7(2) . . ?
C5 C6 C10 120.7(2) . . ?
C7 C6 C10 121.5(2) . . ?
C8 C7 C6 122.4(2) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C7 C8 C9 120.6(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
N1 C9 C4 122.5(2) . . ?
N1 C9 C8 118.9(2) . . ?
C4 C9 C8 118.6(2) . . ?
C11 C10 C15 117.3(2) . . ?
C11 C10 C6 120.6(2) . . ?
C15 C10 C6 122.1(2) . . ?
C12 C11 C10 122.4(3) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C13 C12 C11 118.9(3) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.1(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
O1 C15 C14 123.7(2) . . ?
O1 C15 C10 115.7(2) . . ?
C14 C15 C10 120.6(3) . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 118.1(2) . . ?
C18 C17 C1 122.6(2) . . ?
C22 C17 C1 119.3(2) . . ?
C19 C18 C17 121.4(2) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 121.6(2) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C19 C20 C21 117.9(2) . . ?
C19 C20 C23 120.3(2) . . ?
C21 C20 C23 121.80(19) . . ?
C22 C21 C20 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C17 120.5(2) . . ?
C21 C22 H22 119.8 . . ?
C17 C22 H22 119.8 . . ?
C28 C23 C24 117.1(2) . . ?
C28 C23 C20 120.6(2) . . ?
C24 C23 C20 122.3(2) . . ?
O2 C24 C25 123.5(2) . . ?
O2 C24 C23 115.94(19) . . ?
C25 C24 C23 120.6(2) . . ?
C26 C25 C24 120.5(3) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C27 C26 C25 120.4(3) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C28 119.8(3) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C27 C28 C23 121.7(3) . . ?
C27 C28 H28 119.1 . . ?
C23 C28 H28 119.1 . . ?
O2 C29 H29A 109.5 . . ?
O2 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O2 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C1 N1 C9 118.0(2) . . ?
C15 O1 C16 118.8(2) . . ?
C24 O2 C29 118.07(19) . . ?



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






































































N1 C1 C2 C3 2.3(4) . . . . ?
C17 C1 C2 C3 -174.5(2) . . . . ?
C1 C2 C3 C4 -2.3(4) . . . . ?
C2 C3 C4 C9 -0.1(3) . . . . ?
C2 C3 C4 C5 -178.3(2) . . . . ?
C9 C4 C5 C6 -1.6(3) . . . . ?
C3 C4 C5 C6 176.6(2) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C4 C5 C6 C10 179.0(2) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C10 C6 C7 C8 -177.5(2) . . . . ?
C6 C7 C8 C9 -1.5(3) . . . . ?
C3 C4 C9 N1 2.6(3) . . . . ?
C5 C4 C9 N1 -179.14(19) . . . . ?
C3 C4 C9 C8 -177.8(2) . . . . ?
C5 C4 C9 C8 0.4(3) . . . . ?
C7 C8 C9 N1 -179.36(19) . . . . ?
C7 C8 C9 C4 1.1(3) . . . . ?
C5 C6 C10 C11 -49.7(3) . . . . ?
C7 C6 C10 C11 128.0(2) . . . . ?
C5 C6 C10 C15 130.5(2) . . . . ?
C7 C6 C10 C15 -51.7(3) . . . . ?
C15 C10 C11 C12 -0.2(3) . . . . ?
C6 C10 C11 C12 180.0(2) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C15 1.2(4) . . . . ?
C13 C14 C15 O1 -179.7(2) . . . . ?
C13 C14 C15 C10 -1.3(4) . . . . ?
C11 C10 C15 O1 179.4(2) . . . . ?
C6 C10 C15 O1 -0.9(3) . . . . ?
C11 C10 C15 C14 0.8(3) . . . . ?
C6 C10 C15 C14 -179.4(2) . . . . ?
N1 C1 C17 C18 158.9(2) . . . . ?
C2 C1 C17 C18 -24.0(3) . . . . ?
N1 C1 C17 C22 -22.2(3) . . . . ?
C2 C1 C17 C22 154.9(2) . . . . ?
C22 C17 C18 C19 -1.3(3) . . . . ?
C1 C17 C18 C19 177.7(2) . . . . ?
C17 C18 C19 C20 -0.2(4) . . . . ?
C18 C19 C20 C21 1.1(3) . . . . ?
C18 C19 C20 C23 178.6(2) . . . . ?
C19 C20 C21 C22 -0.6(3) . . . . ?
C23 C20 C21 C22 -178.0(2) . . . . ?
C20 C21 C22 C17 -0.9(3) . . . . ?
C18 C17 C22 C21 1.8(3) . . . . ?
C1 C17 C22 C21 -177.2(2) . . . . ?
C19 C20 C23 C28 -42.4(3) . . . . ?
C21 C20 C23 C28 135.0(2) . . . . ?
C19 C20 C23 C24 137.5(2) . . . . ?
C21 C20 C23 C24 -45.2(3) . . . . ?
C28 C23 C24 O2 176.6(2) . . . . ?
C20 C23 C24 O2 -3.3(3) . . . . ?
C28 C23 C24 C25 -1.8(3) . . . . ?
C20 C23 C24 C25 178.3(2) . . . . ?
O2 C24 C25 C26 -177.5(2) . . . . ?
C23 C24 C25 C26 0.7(4) . . . . ?
C24 C25 C26 C27 0.6(4) . . . . ?
C25 C26 C27 C28 -0.7(4) . . . . ?
C26 C27 C28 C23 -0.5(4) . . . . ?
C24 C23 C28 C27 1.7(4) . . . . ?
C20 C23 C28 C27 -178.4(2) . . . . ?
C2 C1 N1 C9 0.1(3) . . . . ?
C17 C1 N1 C9 177.11(17) . . . . ?
C4 C9 N1 C1 -2.7(3) . . . . ?
C8 C9 N1 C1 177.8(2) . . . . ?
C14 C15 O1 C16 1.1(4) . . . . ?
C10 C15 O1 C16 -177.4(2) . . . . ?
C25 C24 O2 C29 0.9(4) . . . . ?
C23 C24 O2 C29 -177.4(2) . . . . ?



_diffrn_measured_fraction_theta_max 0.983

_diffrn_reflns_theta_full        25.50

_diffrn_measured_fraction_theta_full 0.983

_refine_diff_density_max         0.308

_refine_diff_density_min         -0.167

_refine_diff_density_rms         0.031

_database_code_depnum_ccdc_archive 'CCDC 969899'
