# 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_xstr0016
_audit_creation_date             2014-01-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H19 N O'
_chemical_formula_sum            'C24 H19 N O'
_chemical_formula_weight         337.40
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H17 N1 O1'
_chemical_oxdiff_usercomment     'Frank King MW323'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_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                   16.9504(14)
_cell_length_b                   11.2305(10)
_cell_length_c                   9.1731(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.305(10)
_cell_angle_gamma                90
_cell_volume                     1699.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1941
_cell_measurement_temperature    150
_cell_measurement_theta_max      73.4560
_cell_measurement_theta_min      4.7770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2772
_diffrn_reflns_point_group_measured_fraction_full 0.555
_diffrn_reflns_point_group_measured_fraction_max 0.530
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.663
_diffrn_reflns_theta_min         4.764
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 5.2031
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651   38.0000   90.0000 78

#__ type_ start__ end____ width___ exp.time_
  2 omega -123.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -99.0000  150.0000 44

#__ type_ start__ end____ width___ exp.time_
  3 omega   67.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5651 -126.0000 -136.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -47.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000   45.0000   30.0000 60

#__ type_ start__ end____ width___ exp.time_
  5 omega   91.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.9963   45.0000 -120.0000 60

#__ type_ start__ end____ width___ exp.time_
  6 omega   45.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.9963  -95.0000 -180.0000 56

#__ type_ start__ end____ width___ exp.time_
  7 omega   34.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.9963 -125.0000  150.0000 76

#__ type_ start__ end____ width___ exp.time_
  8 omega   25.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.9963  -95.0000  -90.0000 67

#__ type_ start__ end____ width___ exp.time_
  9 omega   33.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.9963  -30.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
 10 omega   54.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.9963  -30.0000   60.0000 36
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0124028000
_diffrn_orient_matrix_UB_12      -0.1350092000
_diffrn_orient_matrix_UB_13      -0.0277236000
_diffrn_orient_matrix_UB_21      -0.0923260000
_diffrn_orient_matrix_UB_22      0.0160847000
_diffrn_orient_matrix_UB_23      -0.0250595000
_diffrn_orient_matrix_UB_31      -0.0062854000
_diffrn_orient_matrix_UB_32      0.0190304000
_diffrn_orient_matrix_UB_33      -0.1684134000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.130
_reflns_Friedel_fraction_full    0.132
_reflns_Friedel_fraction_max     0.122
_reflns_number_gt                1756
_reflns_number_total             1846
_reflns_odcompleteness_completeness 97.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 191 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         1846
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0582
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.049
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0739P)²+2.3398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1438
_refine_ls_wR_factor_ref         0.1464
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2942(2) 0.4770(4) 0.4164(5) 0.0637(12) Uani 1 1 d . . . . .
N1 N 0.3720(2) 0.3180(4) 0.3975(5) 0.0440(10) Uani 1 1 d . . . . .
C1 C 0.3522(2) 0.4324(4) 0.3796(5) 0.0365(10) Uani 1 1 d . . . . .
C2 C 0.4126(3) 0.4927(4) 0.3051(7) 0.0483(13) Uani 1 1 d . . . . .
H2A H 0.3895 0.5042 0.1967 0.058 Uiso 1 1 calc R . . . .
H2B H 0.4293 0.5710 0.3516 0.058 Uiso 1 1 calc R . . . .
C3 C 0.4818(3) 0.4092(4) 0.3305(6) 0.0432(11) Uani 1 1 d . . . . .
H3 H 0.5124 0.4228 0.4362 0.052 Uiso 1 1 calc R . . . .
C4 C 0.5445(2) 0.4183(4) 0.2349(4) 0.0309(9) Uani 1 1 d . . . . .
C5 C 0.5745(3) 0.5306(4) 0.2217(5) 0.0341(9) Uani 1 1 d . . . . .
H5 H 0.5507 0.5964 0.2606 0.041 Uiso 1 1 calc R . . . .
C6 C 0.6386(3) 0.5511(4) 0.1533(5) 0.0402(11) Uani 1 1 d . . . . .
H6 H 0.6581 0.6295 0.1449 0.048 Uiso 1 1 calc R . . . .
C7 C 0.6733(2) 0.4549(5) 0.0979(5) 0.0395(11) Uani 1 1 d . . . . .
H7 H 0.7170 0.4670 0.0506 0.047 Uiso 1 1 calc R . . . .
C8 C 0.6447(2) 0.3416(4) 0.1110(5) 0.0323(9) Uani 1 1 d . . . . .
H8 H 0.6692 0.2763 0.0726 0.039 Uiso 1 1 calc R . . . .
C9 C 0.5806(2) 0.3204(4) 0.1796(4) 0.0287(8) Uani 1 1 d . . . . .
C10 C 0.5549(2) 0.1919(4) 0.1971(5) 0.0292(9) Uani 1 1 d . . . . .
H10 H 0.5909 0.1371 0.1557 0.035 Uiso 1 1 calc R . . . .
C11 C 0.5631(2) 0.1648(3) 0.3611(5) 0.0296(9) Uani 1 1 d . . . . .
C12 C 0.5027(2) 0.2080(4) 0.4295(5) 0.0325(9) Uani 1 1 d . . . . .
C13 C 0.4391(3) 0.2840(4) 0.3302(5) 0.0382(11) Uani 1 1 d . . . . .
C14 C 0.4090(2) 0.2261(4) 0.1761(5) 0.0367(10) Uani 1 1 d . . . . .
C15 C 0.4685(2) 0.1749(4) 0.1117(5) 0.0330(9) Uani 1 1 d . . . . .
C16 C 0.4475(3) 0.1187(4) -0.0258(5) 0.0391(10) Uani 1 1 d . . . . .
H16 H 0.4879 0.0827 -0.0676 0.047 Uiso 1 1 calc R . . . .
C17 C 0.3665(3) 0.1153(5) -0.1022(6) 0.0503(13) Uani 1 1 d . . . . .
H17 H 0.3509 0.0749 -0.1953 0.060 Uiso 1 1 calc R . . . .
C18 C 0.3083(3) 0.1723(6) -0.0404(7) 0.0557(15) Uani 1 1 d . . . . .
H18 H 0.2534 0.1744 -0.0949 0.067 Uiso 1 1 calc R . . . .
C19 C 0.3299(3) 0.2257(5) 0.0997(6) 0.0479(13) Uani 1 1 d . . . . .
H19 H 0.2897 0.2618 0.1421 0.057 Uiso 1 1 calc R . . . .
C20 C 0.6310(2) 0.1073(4) 0.4487(5) 0.0320(9) Uani 1 1 d . . . . .
H20 H 0.6730 0.0801 0.4040 0.038 Uiso 1 1 calc R . . . .
C21 C 0.6372(3) 0.0898(4) 0.6005(5) 0.0390(10) Uani 1 1 d . . . . .
H21 H 0.6828 0.0494 0.6590 0.047 Uiso 1 1 calc R . . . .
C22 C 0.5766(3) 0.1315(4) 0.6674(6) 0.0413(11) Uani 1 1 d . . . . .
H22 H 0.5810 0.1195 0.7715 0.050 Uiso 1 1 calc R . . . .
C23 C 0.5101(3) 0.1905(4) 0.5824(5) 0.0384(10) Uani 1 1 d . . . . .
H23 H 0.4692 0.2193 0.6287 0.046 Uiso 1 1 calc R . . . .
C24 C 0.3192(3) 0.2318(5) 0.4465(7) 0.0552(14) Uani 1 1 d . . . . .
H24A H 0.3183 0.2475 0.5512 0.083 Uiso 1 1 calc GR . . . .
H24B H 0.3397 0.1512 0.4376 0.083 Uiso 1 1 calc GR . . . .
H24C H 0.2642 0.2389 0.3837 0.083 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.220(5) . ?
N1 C1 1.329(6) . ?
N1 C13 1.464(5) . ?
N1 C24 1.457(6) . ?
C1 C2 1.515(7) . ?
C2 C3 1.478(7) . ?
C3 C4 1.528(6) . ?
C3 C13 1.582(6) . ?
C4 C5 1.376(6) . ?
C4 C9 1.408(6) . ?
C5 C6 1.394(6) . ?
C6 C7 1.382(7) . ?
C7 C8 1.377(7) . ?
C8 C9 1.397(5) . ?
C9 C10 1.526(6) . ?
C10 C11 1.510(6) . ?
C10 C15 1.506(6) . ?
C11 C12 1.405(5) . ?
C11 C20 1.401(6) . ?
C12 C13 1.506(6) . ?
C12 C23 1.393(7) . ?
C13 C14 1.533(7) . ?
C14 C15 1.403(6) . ?
C14 C19 1.363(7) . ?
C15 C16 1.382(7) . ?
C16 C17 1.390(7) . ?
C17 C18 1.401(8) . ?
C18 C19 1.388(9) . ?
C20 C21 1.386(6) . ?
C21 C22 1.393(7) . ?
C22 C23 1.383(7) . ?

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
C1 N1 C13 113.5(4) . . ?
C1 N1 C24 121.7(4) . . ?
C24 N1 C13 123.3(4) . . ?
O1 C1 N1 124.0(5) . . ?
O1 C1 C2 127.8(5) . . ?
N1 C1 C2 108.1(3) . . ?
C3 C2 C1 103.8(4) . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 C13 102.5(4) . . ?
C4 C3 C13 115.9(4) . . ?
C5 C4 C3 115.6(4) . . ?
C5 C4 C9 118.9(4) . . ?
C9 C4 C3 124.8(4) . . ?
C4 C5 C6 122.3(4) . . ?
C7 C6 C5 118.6(4) . . ?
C8 C7 C6 120.1(4) . . ?
C7 C8 C9 121.6(4) . . ?
C4 C9 C10 122.9(3) . . ?
C8 C9 C4 118.5(4) . . ?
C8 C9 C10 118.6(4) . . ?
C11 C10 C9 109.4(3) . . ?
C15 C10 C9 109.4(3) . . ?
C15 C10 C11 110.4(3) . . ?
C12 C11 C10 117.8(4) . . ?
C20 C11 C10 122.7(4) . . ?
C20 C11 C12 119.3(4) . . ?
C11 C12 C13 114.8(4) . . ?
C23 C12 C11 119.6(4) . . ?
C23 C12 C13 125.1(4) . . ?
N1 C13 C3 99.6(3) . . ?
N1 C13 C12 114.2(4) . . ?
N1 C13 C14 112.0(4) . . ?
C12 C13 C3 103.8(4) . . ?
C12 C13 C14 110.9(3) . . ?
C14 C13 C3 115.7(4) . . ?
C15 C14 C13 116.3(4) . . ?
C19 C14 C13 123.7(4) . . ?
C19 C14 C15 119.9(5) . . ?
C14 C15 C10 115.9(4) . . ?
C16 C15 C10 123.2(4) . . ?
C16 C15 C14 120.8(4) . . ?
C15 C16 C17 119.4(5) . . ?
C16 C17 C18 119.3(5) . . ?
C19 C18 C17 120.8(5) . . ?
C14 C19 C18 119.7(5) . . ?
C21 C20 C11 120.2(4) . . ?
C20 C21 C22 120.2(4) . . ?
C23 C22 C21 120.0(4) . . ?
C22 C23 C12 120.6(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 162.7(5) . . . . ?
N1 C1 C2 C3 -18.3(6) . . . . ?
N1 C13 C14 C15 -171.1(4) . . . . ?
N1 C13 C14 C19 10.9(6) . . . . ?
C1 N1 C13 C3 24.4(5) . . . . ?
C1 N1 C13 C12 134.4(4) . . . . ?
C1 N1 C13 C14 -98.5(5) . . . . ?
C1 C2 C3 C4 161.9(4) . . . . ?
C1 C2 C3 C13 31.8(5) . . . . ?
C2 C3 C4 C5 48.9(6) . . . . ?
C2 C3 C4 C9 -140.5(5) . . . . ?
C2 C3 C13 N1 -33.7(5) . . . . ?
C2 C3 C13 C12 -151.7(4) . . . . ?
C2 C3 C13 C14 86.5(5) . . . . ?
C3 C4 C5 C6 172.3(4) . . . . ?
C3 C4 C9 C8 -171.4(4) . . . . ?
C3 C4 C9 C10 6.0(6) . . . . ?
C3 C13 C14 C15 75.7(5) . . . . ?
C3 C13 C14 C19 -102.3(5) . . . . ?
C4 C3 C13 N1 -166.2(4) . . . . ?
C4 C3 C13 C12 75.8(5) . . . . ?
C4 C3 C13 C14 -46.0(5) . . . . ?
C4 C5 C6 C7 -0.4(7) . . . . ?
C4 C9 C10 C11 -56.8(5) . . . . ?
C4 C9 C10 C15 64.2(5) . . . . ?
C5 C4 C9 C8 -1.1(6) . . . . ?
C5 C4 C9 C10 176.3(4) . . . . ?
C5 C6 C7 C8 -0.2(7) . . . . ?
C6 C7 C8 C9 0.1(6) . . . . ?
C7 C8 C9 C4 0.5(6) . . . . ?
C7 C8 C9 C10 -177.0(4) . . . . ?
C8 C9 C10 C11 120.6(4) . . . . ?
C8 C9 C10 C15 -118.4(4) . . . . ?
C9 C4 C5 C6 1.1(6) . . . . ?
C9 C10 C11 C12 77.5(4) . . . . ?
C9 C10 C11 C20 -97.3(4) . . . . ?
C9 C10 C15 C14 -73.7(4) . . . . ?
C9 C10 C15 C16 102.7(5) . . . . ?
C10 C11 C12 C13 -3.8(5) . . . . ?
C10 C11 C12 C23 -176.6(4) . . . . ?
C10 C11 C20 C21 176.8(4) . . . . ?
C10 C15 C16 C17 -174.9(4) . . . . ?
C11 C10 C15 C14 46.8(5) . . . . ?
C11 C10 C15 C16 -136.8(4) . . . . ?
C11 C12 C13 N1 173.9(4) . . . . ?
C11 C12 C13 C3 -78.7(4) . . . . ?
C11 C12 C13 C14 46.2(5) . . . . ?
C11 C12 C23 C22 0.3(6) . . . . ?
C11 C20 C21 C22 -1.3(6) . . . . ?
C12 C11 C20 C21 2.1(6) . . . . ?
C12 C13 C14 C15 -42.2(5) . . . . ?
C12 C13 C14 C19 139.8(4) . . . . ?
C13 N1 C1 O1 174.0(5) . . . . ?
C13 N1 C1 C2 -5.1(6) . . . . ?
C13 C3 C4 C5 172.8(4) . . . . ?
C13 C3 C4 C9 -16.6(6) . . . . ?
C13 C12 C23 C22 -171.7(4) . . . . ?
C13 C14 C15 C10 -4.6(5) . . . . ?
C13 C14 C15 C16 178.9(4) . . . . ?
C13 C14 C19 C18 179.2(4) . . . . ?
C14 C15 C16 C17 1.4(7) . . . . ?
C15 C10 C11 C12 -42.8(5) . . . . ?
C15 C10 C11 C20 142.3(4) . . . . ?
C15 C14 C19 C18 1.3(8) . . . . ?
C15 C16 C17 C18 2.0(7) . . . . ?
C16 C17 C18 C19 -3.8(8) . . . . ?
C17 C18 C19 C14 2.1(8) . . . . ?
C19 C14 C15 C10 173.4(4) . . . . ?
C19 C14 C15 C16 -3.1(7) . . . . ?
C20 C11 C12 C13 171.2(4) . . . . ?
C20 C11 C12 C23 -1.6(6) . . . . ?
C20 C21 C22 C23 0.0(6) . . . . ?
C21 C22 C23 C12 0.5(6) . . . . ?
C23 C12 C13 N1 -13.8(6) . . . . ?
C23 C12 C13 C3 93.7(5) . . . . ?
C23 C12 C13 C14 -141.4(4) . . . . ?
C24 N1 C1 O1 7.9(8) . . . . ?
C24 N1 C1 C2 -171.1(5) . . . . ?
C24 N1 C13 C3 -169.9(5) . . . . ?
C24 N1 C13 C12 -59.9(7) . . . . ?
C24 N1 C13 C14 67.3(6) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 958857'
#######################################################################
#
#                 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_xstr0122
_audit_creation_date             2014-01-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H21 N O, 1.67(C2.1)'
_chemical_formula_sum            'C28.50 H21 N O'
_chemical_formula_weight         393.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C28.5 H24 N1 O1'
_chemical_oxdiff_usercomment     'FK 15/54'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9866(3)
_cell_length_b                   9.1620(3)
_cell_length_c                   13.9462(5)
_cell_angle_alpha                93.732(3)
_cell_angle_beta                 95.624(3)
_cell_angle_gamma                115.839(4)
_cell_volume                     1021.00(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10379
_cell_measurement_temperature    150
_cell_measurement_theta_max      73.8870
_cell_measurement_theta_min      5.3830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15767
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.144
_diffrn_reflns_theta_min         5.404
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 5.2031
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -112.00  -58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -57.0000   60.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega  -84.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000  -60.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000   90.0000 42

#__ type_ start__ end____ width___ exp.time_
  4 omega  -36.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega  -95.00  -20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  125.0000 -120.0000 75

#__ type_ start__ end____ width___ exp.time_
  6 omega -115.00  -89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega  -81.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -57.0000 -180.0000 66

#__ type_ start__ end____ width___ exp.time_
  8 omega -111.00  -86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -57.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega  -52.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -57.0000   60.0000 40

#__ type_ start__ end____ width___ exp.time_
 10 omega   29.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5651 -125.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
 11 omega    2.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5651   92.0000 -144.5221 25

#__ type_ start__ end____ width___ exp.time_
 12 omega -139.00  -74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
 13 omega  -55.00  -29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -76.0000  -17.6180 26

#__ type_ start__ end____ width___ exp.time_
 14 omega -139.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  150.0000 60

#__ type_ start__ end____ width___ exp.time_
 15 omega  -53.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -76.0000  -59.8136 25

#__ type_ start__ end____ width___ exp.time_
 16 omega  -59.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   30.0000 31

#__ type_ start__ end____ width___ exp.time_
 17 omega -135.00  -74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000 -125.0000  -90.0000 61

#__ type_ start__ end____ width___ exp.time_
 18 omega  -62.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
 19 omega  -54.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega -129.00 -104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 21 omega  -63.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
 22 omega  -58.00  -29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -75.0000   66.5360 29

#__ type_ start__ end____ width___ exp.time_
 23 omega  -53.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega -138.00 -103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -75.0000   66.5360 35

#__ type_ start__ end____ width___ exp.time_
 25 omega  -56.00  -29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 26 omega -124.00  -98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -76.0000  -59.8136 26

#__ type_ start__ end____ width___ exp.time_
 27 omega -138.00 -101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -76.0000  -17.6180 37

#__ type_ start__ end____ width___ exp.time_
 28 omega   81.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000  120.0000 64

#__ type_ start__ end____ width___ exp.time_
 29 omega   79.00  152.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000  150.0000 73

#__ type_ start__ end____ width___ exp.time_
 30 omega   75.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 31 omega  110.00  171.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713  125.0000  -30.0000 61

#__ type_ start__ end____ width___ exp.time_
 32 omega   34.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713  -45.0000  -90.0000 63

#__ type_ start__ end____ width___ exp.time_
 33 omega   75.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   79.00  156.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000 -120.0000 77

#__ type_ start__ end____ width___ exp.time_
 35 omega   75.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  -90.0000 70

#__ type_ start__ end____ width___ exp.time_
 36 omega   78.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000   60.0000 98

#__ type_ start__ end____ width___ exp.time_
 37 omega   78.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 38 omega   75.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
 39 omega   27.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713  -95.0000  150.0000 83

#__ type_ start__ end____ width___ exp.time_
 40 omega  108.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 41 omega   25.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713  -95.0000  -90.0000 84

#__ type_ start__ end____ width___ exp.time_
 42 omega   76.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
 43 omega   76.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  -60.0000 101

#__ type_ start__ end____ width___ exp.time_
 44 omega   76.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000    0.0000 87

#__ type_ start__ end____ width___ exp.time_
 45 omega   78.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 46 omega   75.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 47 omega   78.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 48 omega   76.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 49 omega   79.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 50 omega   77.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 51 omega  126.00  152.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 52 omega   75.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 53 omega   26.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713  -95.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
 54 omega   34.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713  -45.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
 55 omega   75.00  165.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
 56 omega   76.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   72.0000  -67.8892 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0766559000
_diffrn_orient_matrix_UB_12      -0.1797133000
_diffrn_orient_matrix_UB_13      -0.0451474000
_diffrn_orient_matrix_UB_21      0.1560552000
_diffrn_orient_matrix_UB_22      -0.0135607000
_diffrn_orient_matrix_UB_23      0.0455547000
_diffrn_orient_matrix_UB_31      -0.0823599000
_diffrn_orient_matrix_UB_32      -0.0541897000
_diffrn_orient_matrix_UB_33      0.0915877000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3665
_reflns_number_total             4025
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4025
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0585
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0857P)²+0.7310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1632
_refine_special_details          
'The structure contains a molecule of toluene disordered over the inversion centre. In addition that molecule occupies two orrientations modelled as 60:40 occupancy. The carbon atoms of teh solvent were modelled isotropically and hydrogen atoms were not included in the model for teh solvent.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Others
 Fixed Sof: C31(0.6) C32(0.6) C33(0.6) C34(0.3) C41(0.4) C42(0.4) C43(0.4)
 C44(0.2)
3.a Ternary CH refined with riding coordinates:
 C11(H11), C18(H18), C19(H19)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15),
 C16(H16), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5113(2) 0.03055(18) 0.37422(10) 0.0387(4) Uani 1 1 d . . . . .
N1 N 0.3990(2) 0.1430(2) 0.47567(11) 0.0339(4) Uani 1 1 d . . . . .
H1 H 0.4342 0.1056 0.5232 0.041 Uiso 1 1 calc R . . . .
C1 C 0.4460(2) 0.1225(2) 0.38924(13) 0.0284(4) Uani 1 1 d . . . . .
C2 C 0.2944(2) 0.2225(2) 0.49707(13) 0.0298(4) Uani 1 1 d . . . . .
H2A H 0.3346 0.2824 0.5616 0.036 Uiso 1 1 calc R . . . .
H2B H 0.1812 0.1393 0.4972 0.036 Uiso 1 1 calc R . . . .
C3 C 0.2919(2) 0.3395(2) 0.42479(12) 0.0242(4) Uani 1 1 d . . . . .
H3A H 0.3921 0.4422 0.4413 0.029 Uiso 1 1 calc R . . . .
H3B H 0.1967 0.3615 0.4305 0.029 Uiso 1 1 calc R . . . .
C4 C 0.28224(19) 0.27399(19) 0.31977(11) 0.0198(3) Uani 1 1 d . . . . .
C5 C 0.1203(2) 0.12487(19) 0.27676(12) 0.0207(3) Uani 1 1 d . . . . .
C6 C -0.0243(2) 0.0540(2) 0.31879(13) 0.0272(4) Uani 1 1 d . . . . .
H6 H -0.0282 0.0944 0.3809 0.033 Uiso 1 1 calc R . . . .
C7 C -0.1641(2) -0.0782(2) 0.26750(14) 0.0317(4) Uani 1 1 d . . . . .
H7 H -0.2621 -0.1242 0.2951 0.038 Uiso 1 1 calc R . . . .
C8 C -0.1583(2) -0.1414(2) 0.17619(14) 0.0291(4) Uani 1 1 d . . . . .
H8 H -0.2509 -0.2324 0.1436 0.035 Uiso 1 1 calc R . . . .
C9 C -0.0140(2) -0.0692(2) 0.13245(13) 0.0244(4) Uani 1 1 d . . . . .
H9 H -0.0101 -0.1115 0.0708 0.029 Uiso 1 1 calc R . . . .
C10 C 0.1233(2) 0.06593(19) 0.18181(12) 0.0202(3) Uani 1 1 d . . . . .
C11 C 0.28259(19) 0.16650(19) 0.14169(11) 0.0189(3) Uani 1 1 d . . . . .
H11 H 0.2774 0.1272 0.0738 0.023 Uiso 1 1 calc R . . . .
C12 C 0.31050(18) 0.34234(19) 0.15361(11) 0.0177(3) Uani 1 1 d . . . . .
C13 C 0.34097(19) 0.4450(2) 0.08178(12) 0.0213(3) Uani 1 1 d . . . . .
H13 H 0.3419 0.4063 0.0186 0.026 Uiso 1 1 calc R . . . .
C14 C 0.3703(2) 0.6067(2) 0.10448(13) 0.0257(4) Uani 1 1 d . . . . .
H14 H 0.3907 0.6760 0.0564 0.031 Uiso 1 1 calc R . . . .
C15 C 0.3691(2) 0.6640(2) 0.19868(14) 0.0272(4) Uani 1 1 d . . . . .
H15 H 0.3888 0.7718 0.2136 0.033 Uiso 1 1 calc R . . . .
C16 C 0.3385(2) 0.5608(2) 0.27147(13) 0.0234(4) Uani 1 1 d . . . . .
H16 H 0.3375 0.5997 0.3346 0.028 Uiso 1 1 calc R . . . .
C17 C 0.30954(18) 0.40032(19) 0.24905(11) 0.0184(3) Uani 1 1 d . . . . .
C18 C 0.4304(2) 0.2283(2) 0.31296(11) 0.0205(3) Uani 1 1 d . . . . .
H18 H 0.5328 0.3315 0.3262 0.025 Uiso 1 1 calc R . . . .
C19 C 0.4266(2) 0.15509(19) 0.20879(12) 0.0198(3) Uani 1 1 d . . . . .
H19 H 0.3965 0.0389 0.2106 0.024 Uiso 1 1 calc R . . . .
C20 C 0.5920(2) 0.2312(2) 0.16924(12) 0.0212(3) Uani 1 1 d . . . . .
C21 C 0.6487(2) 0.1293(2) 0.12368(15) 0.0311(4) Uani 1 1 d . . . . .
H21 H 0.5844 0.0167 0.1177 0.037 Uiso 1 1 calc R . . . .
C22 C 0.7992(3) 0.1929(3) 0.08716(17) 0.0400(5) Uani 1 1 d . . . . .
H22 H 0.8351 0.1226 0.0572 0.048 Uiso 1 1 calc R . . . .
C23 C 0.8969(2) 0.3601(3) 0.09478(15) 0.0352(5) Uani 1 1 d . . . . .
H23 H 0.9987 0.4024 0.0710 0.042 Uiso 1 1 calc R . . . .
C24 C 0.8412(2) 0.4631(2) 0.13812(14) 0.0300(4) Uani 1 1 d . . . . .
H24 H 0.9051 0.5757 0.1427 0.036 Uiso 1 1 calc R . . . .
C25 C 0.6896(2) 0.3994(2) 0.17511(13) 0.0258(4) Uani 1 1 d . . . . .
H25 H 0.6533 0.4701 0.2040 0.031 Uiso 1 1 calc R . . . .
C31 C 0.0947(5) 0.5808(6) 0.5747(3) 0.0389(10) Uiso 0.6 1 d . . P A 1
C32 C 0.0037(7) 0.5807(6) 0.4079(4) 0.0589(12) Uiso 0.6 1 d . . P A 1
C33 C 0.1141(9) 0.6690(9) 0.5012(6) 0.0797(17) Uiso 0.6 1 d . . P A 1
C34 C 0.1117(13) 0.7332(12) 0.4400(8) 0.062(2) Uiso 0.3 1 d . . P A 1
C41 C 0.0459(9) 0.5958(8) 0.4534(6) 0.0464(14) Uiso 0.4 1 d . . P B 2
C42 C 0.1348(10) 0.6775(10) 0.5470(7) 0.0565(18) Uiso 0.4 1 d . . P B 2
C43 C 0.0699(9) 0.5417(9) 0.5983(5) 0.0434(17) Uiso 0.4 1 d . . P B 2
C44 C 0.0607(14) 0.6987(13) 0.3557(8) 0.040(2) Uiso 0.2 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.237(2) . ?
N1 C1 1.344(2) . ?
N1 C2 1.458(3) . ?
C1 C18 1.521(2) . ?
C2 C3 1.524(2) . ?
C3 C4 1.526(2) . ?
C4 C5 1.527(2) . ?
C4 C17 1.524(2) . ?
C4 C18 1.570(2) . ?
C5 C6 1.385(2) . ?
C5 C10 1.404(2) . ?
C6 C7 1.393(3) . ?
C7 C8 1.379(3) . ?
C8 C9 1.397(3) . ?
C9 C10 1.386(2) . ?
C10 C11 1.512(2) . ?
C11 C12 1.514(2) . ?
C11 C19 1.567(2) . ?
C12 C13 1.384(2) . ?
C12 C17 1.403(2) . ?
C13 C14 1.395(2) . ?
C14 C15 1.385(3) . ?
C15 C16 1.397(2) . ?
C16 C17 1.385(2) . ?
C18 C19 1.551(2) . ?
C19 C20 1.518(2) . ?
C20 C21 1.392(2) . ?
C20 C25 1.394(2) . ?
C21 C22 1.384(3) . ?
C22 C23 1.385(3) . ?
C23 C24 1.380(3) . ?
C24 C25 1.395(3) . ?
C31 C32 1.407(7) 2_566 ?
C31 C33 1.325(9) . ?
C32 C31 1.407(7) 2_566 ?
C32 C33 1.497(9) . ?
C32 C34 1.321(11) . ?
C33 C34 1.071(12) . ?
C41 C42 1.431(11) . ?
C41 C43 1.335(10) 2_566 ?
C41 C44 1.691(13) . ?
C42 C43 1.402(11) . ?
C43 C41 1.335(10) 2_566 ?

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
C1 N1 C2 126.57(15) . . ?
O1 C1 N1 121.62(16) . . ?
O1 C1 C18 120.74(16) . . ?
N1 C1 C18 117.41(15) . . ?
N1 C2 C3 113.38(15) . . ?
C2 C3 C4 113.30(14) . . ?
C3 C4 C5 116.10(14) . . ?
C3 C4 C18 108.36(13) . . ?
C5 C4 C18 108.01(13) . . ?
C17 C4 C3 113.71(13) . . ?
C17 C4 C5 105.84(12) . . ?
C17 C4 C18 104.04(12) . . ?
C6 C5 C4 127.07(15) . . ?
C6 C5 C10 119.73(15) . . ?
C10 C5 C4 113.06(14) . . ?
C5 C6 C7 119.66(16) . . ?
C8 C7 C6 120.58(17) . . ?
C7 C8 C9 120.22(16) . . ?
C10 C9 C8 119.38(16) . . ?
C5 C10 C11 113.75(14) . . ?
C9 C10 C5 120.29(15) . . ?
C9 C10 C11 125.92(15) . . ?
C10 C11 C12 107.39(13) . . ?
C10 C11 C19 106.13(12) . . ?
C12 C11 C19 107.84(12) . . ?
C13 C12 C11 126.21(15) . . ?
C13 C12 C17 120.31(14) . . ?
C17 C12 C11 113.45(13) . . ?
C12 C13 C14 119.75(16) . . ?
C15 C14 C13 119.98(15) . . ?
C14 C15 C16 120.49(15) . . ?
C17 C16 C15 119.59(16) . . ?
C12 C17 C4 113.48(13) . . ?
C16 C17 C4 126.58(15) . . ?
C16 C17 C12 119.89(15) . . ?
C1 C18 C4 113.83(14) . . ?
C1 C18 C19 112.32(13) . . ?
C19 C18 C4 111.74(12) . . ?
C18 C19 C11 107.69(12) . . ?
C20 C19 C11 112.12(13) . . ?
C20 C19 C18 114.56(13) . . ?
C21 C20 C19 118.92(15) . . ?
C21 C20 C25 117.95(16) . . ?
C25 C20 C19 123.13(15) . . ?
C22 C21 C20 121.08(17) . . ?
C21 C22 C23 120.58(18) . . ?
C24 C23 C22 119.17(17) . . ?
C23 C24 C25 120.36(17) . . ?
C20 C25 C24 120.84(17) . . ?
C33 C31 C32 137.7(5) . 2_566 ?
C31 C32 C33 106.7(5) 2_566 . ?
C34 C32 C31 150.4(7) . 2_566 ?
C34 C32 C33 44.1(5) . . ?
C31 C33 C32 115.5(6) . . ?
C34 C33 C31 172.2(9) . . ?
C34 C33 C32 59.2(7) . . ?
C33 C34 C32 76.7(8) . . ?
C42 C41 C44 121.4(7) . . ?
C43 C41 C42 147.2(7) 2_566 . ?
C43 C41 C44 91.0(8) 2_566 . ?
C43 C42 C41 97.2(6) . . ?
C41 C43 C42 115.4(7) 2_566 . ?

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
O1 C1 C18 C4 153.95(17) . . . . ?
O1 C1 C18 C19 25.7(2) . . . . ?
N1 C1 C18 C4 -31.4(2) . . . . ?
N1 C1 C18 C19 -159.68(16) . . . . ?
N1 C2 C3 C4 41.2(2) . . . . ?
C1 N1 C2 C3 -22.1(3) . . . . ?
C1 C18 C19 C11 134.57(14) . . . . ?
C1 C18 C19 C20 -99.95(16) . . . . ?
C2 N1 C1 O1 -167.80(18) . . . . ?
C2 N1 C1 C18 17.6(3) . . . . ?
C2 C3 C4 C5 66.71(19) . . . . ?
C2 C3 C4 C17 -170.11(14) . . . . ?
C2 C3 C4 C18 -54.97(18) . . . . ?
C3 C4 C5 C6 7.5(2) . . . . ?
C3 C4 C5 C10 -176.85(13) . . . . ?
C3 C4 C17 C12 176.39(13) . . . . ?
C3 C4 C17 C16 -1.0(2) . . . . ?
C3 C4 C18 C1 49.63(18) . . . . ?
C3 C4 C18 C19 178.17(13) . . . . ?
C4 C5 C6 C7 177.21(16) . . . . ?
C4 C5 C10 C9 179.84(14) . . . . ?
C4 C5 C10 C11 -2.33(19) . . . . ?
C4 C18 C19 C11 5.23(17) . . . . ?
C4 C18 C19 C20 130.71(14) . . . . ?
C5 C4 C17 C12 -55.00(17) . . . . ?
C5 C4 C17 C16 127.64(16) . . . . ?
C5 C4 C18 C1 -76.90(17) . . . . ?
C5 C4 C18 C19 51.64(17) . . . . ?
C5 C6 C7 C8 1.5(3) . . . . ?
C5 C10 C11 C12 -52.82(17) . . . . ?
C5 C10 C11 C19 62.33(16) . . . . ?
C6 C5 C10 C9 -4.2(2) . . . . ?
C6 C5 C10 C11 173.66(14) . . . . ?
C6 C7 C8 C9 -2.6(3) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C5 3.1(2) . . . . ?
C8 C9 C10 C11 -174.43(15) . . . . ?
C9 C10 C11 C12 124.87(17) . . . . ?
C9 C10 C11 C19 -119.99(17) . . . . ?
C10 C5 C6 C7 1.8(3) . . . . ?
C10 C11 C12 C13 -128.51(16) . . . . ?
C10 C11 C12 C17 53.84(16) . . . . ?
C10 C11 C19 C18 -60.98(15) . . . . ?
C10 C11 C19 C20 172.10(13) . . . . ?
C11 C12 C13 C14 -177.70(14) . . . . ?
C11 C12 C17 C4 0.54(18) . . . . ?
C11 C12 C17 C16 178.10(14) . . . . ?
C11 C19 C20 C21 -103.16(18) . . . . ?
C11 C19 C20 C25 75.95(19) . . . . ?
C12 C11 C19 C18 53.85(16) . . . . ?
C12 C11 C19 C20 -73.06(16) . . . . ?
C12 C13 C14 C15 0.1(2) . . . . ?
C13 C12 C17 C4 -177.27(13) . . . . ?
C13 C12 C17 C16 0.3(2) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C16 C17 C4 176.94(15) . . . . ?
C15 C16 C17 C12 -0.3(2) . . . . ?
C17 C4 C5 C6 -119.67(18) . . . . ?
C17 C4 C5 C10 55.96(17) . . . . ?
C17 C4 C18 C1 170.94(13) . . . . ?
C17 C4 C18 C19 -60.51(16) . . . . ?
C17 C12 C13 C14 -0.2(2) . . . . ?
C18 C4 C5 C6 129.39(17) . . . . ?
C18 C4 C5 C10 -54.98(17) . . . . ?
C18 C4 C17 C12 58.72(16) . . . . ?
C18 C4 C17 C16 -118.65(17) . . . . ?
C18 C19 C20 C21 133.72(16) . . . . ?
C18 C19 C20 C25 -47.2(2) . . . . ?
C19 C11 C12 C13 117.50(16) . . . . ?
C19 C11 C12 C17 -60.16(17) . . . . ?
C19 C20 C21 C22 -179.47(17) . . . . ?
C19 C20 C25 C24 179.60(15) . . . . ?
C20 C21 C22 C23 -0.3(3) . . . . ?
C21 C20 C25 C24 -1.3(3) . . . . ?
C21 C22 C23 C24 -0.9(3) . . . . ?
C22 C23 C24 C25 1.0(3) . . . . ?
C23 C24 C25 C20 0.1(3) . . . . ?
C25 C20 C21 C22 1.4(3) . . . . ?
C31 C32 C33 C31 -0.4(7) 2_566 . . . ?
C31 C32 C33 C34 -173.9(8) 2_566 . . . ?
C31 C32 C34 C33 11.8(15) 2_566 . . . ?
C32 C31 C33 C32 0.6(10) 2_566 . . . ?
C34 C32 C33 C31 173.5(10) . . . . ?
C41 C42 C43 C41 -3.5(9) . . . 2_566 ?
C43 C41 C42 C43 5.9(14) 2_566 . . . ?
C44 C41 C42 C43 176.2(7) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 984577'
