# Electronic Supplementary Material (ESI) for ChemComm.
# 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_b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H17 N O2'
_chemical_formula_weight         339.38

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.9830(18)
_cell_length_b                   9.792(2)
_cell_length_c                   11.223(2)
_cell_angle_alpha                73.14(3)
_cell_angle_beta                 87.60(3)
_cell_angle_gamma                66.13(3)
_cell_volume                     860.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9754
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius cad4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            3374
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.38
_reflns_number_total             3158
_reflns_number_gt                2011
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of 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)+(0.1000P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.037(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3158
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1852
_refine_ls_wR_factor_gt          0.1518
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
N N 0.1425(3) 0.7435(3) 0.47463(19) 0.0395(6) Uani 1 1 d . . .
O1 O 0.2076(3) 0.6824(3) 0.78411(18) 0.0600(6) Uani 1 1 d . . .
C1 C 0.0728(3) 0.7581(3) 0.5837(2) 0.0382(6) Uani 1 1 d . . .
C2 C -0.0788(3) 0.7603(3) 0.6093(2) 0.0372(6) Uani 1 1 d . . .
O2 O 0.2368(3) 0.8737(3) 0.63329(18) 0.0565(6) Uani 1 1 d . . .
C3 C -0.1659(3) 0.7399(3) 0.5173(2) 0.0394(6) Uani 1 1 d . . .
C4 C -0.3253(4) 0.7469(4) 0.5313(3) 0.0503(8) Uani 1 1 d . . .
H4A H -0.3777 0.7693 0.6009 0.060 Uiso 1 1 calc R . .
C5 C -0.4031(4) 0.7214(4) 0.4444(3) 0.0568(8) Uani 1 1 d . . .
H5A H -0.5098 0.7303 0.4531 0.068 Uiso 1 1 calc R . .
C6 C -0.3236(4) 0.6820(4) 0.3418(3) 0.0587(9) Uani 1 1 d . . .
H6A H -0.3758 0.6596 0.2849 0.070 Uiso 1 1 calc R . .
C7 C -0.1712(4) 0.6761(3) 0.3243(3) 0.0480(7) Uani 1 1 d . . .
H7A H -0.1195 0.6486 0.2560 0.058 Uiso 1 1 calc R . .
C8 C -0.0895(3) 0.7112(3) 0.4090(2) 0.0387(6) Uani 1 1 d . . .
C9 C 0.0644(3) 0.7210(3) 0.3903(2) 0.0377(6) Uani 1 1 d . . .
C10 C 0.1476(3) 0.7065(3) 0.2740(2) 0.0391(6) Uani 1 1 d . . .
C11 C 0.0641(4) 0.7846(3) 0.1557(2) 0.0461(7) Uani 1 1 d . . .
H11A H -0.0462 0.8509 0.1478 0.055 Uiso 1 1 calc R . .
C12 C 0.1434(4) 0.7647(4) 0.0502(3) 0.0521(8) Uani 1 1 d . . .
H12A H 0.0856 0.8163 -0.0281 0.063 Uiso 1 1 calc R . .
C13 C 0.3068(4) 0.6693(4) 0.0594(3) 0.0509(8) Uani 1 1 d . . .
H13A H 0.3594 0.6554 -0.0121 0.061 Uiso 1 1 calc R . .
C14 C 0.3922(4) 0.5943(3) 0.1755(3) 0.0456(7) Uani 1 1 d . . .
H14A H 0.5033 0.5307 0.1822 0.055 Uiso 1 1 calc R . .
C15 C 0.3140(3) 0.6129(3) 0.2823(2) 0.0420(7) Uani 1 1 d . . .
H15A H 0.3730 0.5624 0.3602 0.050 Uiso 1 1 calc R . .
C16 C 0.1781(3) 0.7659(3) 0.6784(2) 0.0404(6) Uani 1 1 d . . .
C17 C 0.3369(4) 0.8881(4) 0.7223(3) 0.0562(8) Uani 1 1 d . . .
H17A H 0.3742 0.9678 0.6816 0.084 Uiso 1 1 calc R . .
H17B H 0.4293 0.7900 0.7550 0.084 Uiso 1 1 calc R . .
H17C H 0.2738 0.9159 0.7894 0.084 Uiso 1 1 calc R . .
C18 C -0.1527(3) 0.7861(3) 0.7272(2) 0.0401(7) Uani 1 1 d . . .
C19 C -0.1636(4) 0.6644(4) 0.8224(3) 0.0521(8) Uani 1 1 d . . .
H19A H -0.1222 0.5643 0.8139 0.063 Uiso 1 1 calc R . .
C20 C -0.2351(4) 0.6902(4) 0.9295(3) 0.0599(9) Uani 1 1 d . . .
H20A H -0.2419 0.6077 0.9929 0.072 Uiso 1 1 calc R . .
C21 C -0.2965(4) 0.8383(4) 0.9424(3) 0.0605(9) Uani 1 1 d . . .
H21A H -0.3451 0.8559 1.0144 0.073 Uiso 1 1 calc R . .
C22 C -0.2862(4) 0.9593(4) 0.8495(3) 0.0611(9) Uani 1 1 d . . .
H22A H -0.3276 1.0590 0.8588 0.073 Uiso 1 1 calc R . .
C23 C -0.2145(4) 0.9346(3) 0.7416(3) 0.0506(8) Uani 1 1 d . . .
H23A H -0.2077 1.0176 0.6789 0.061 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
N C9 1.318(3) . ?
N C1 1.369(3) . ?
O1 C16 1.198(3) . ?
C1 C2 1.373(4) . ?
C1 C16 1.490(4) . ?
C2 C3 1.425(4) . ?
C2 C18 1.497(3) . ?
O2 C16 1.330(3) . ?
O2 C17 1.443(3) . ?
C3 C4 1.410(4) . ?
C3 C8 1.414(4) . ?
C4 C5 1.358(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.397(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.355(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.419(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.427(4) . ?
C9 C10 1.491(3) . ?
C10 C15 1.391(4) . ?
C10 C11 1.393(4) . ?
C11 C12 1.378(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.373(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.378(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.384(4) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.385(4) . ?
C18 C23 1.387(4) . ?
C19 C20 1.379(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.377(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.364(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.385(4) . ?
C22 H22A 0.9300 . ?
C23 H23A 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 N C1 118.6(2) . . ?
N C1 C2 124.5(2) . . ?
N C1 C16 114.5(2) . . ?
C2 C1 C16 120.9(2) . . ?
C1 C2 C3 117.2(2) . . ?
C1 C2 C18 122.0(2) . . ?
C3 C2 C18 120.8(2) . . ?
C16 O2 C17 115.3(2) . . ?
C4 C3 C8 119.2(2) . . ?
C4 C3 C2 122.0(2) . . ?
C8 C3 C2 118.9(2) . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C6 C7 C8 120.8(3) . . ?
C6 C7 H7A 119.6 . . ?
C8 C7 H7A 119.6 . . ?
C3 C8 C7 118.1(2) . . ?
C3 C8 C9 118.2(2) . . ?
C7 C8 C9 123.7(2) . . ?
N C9 C8 122.3(2) . . ?
N C9 C10 115.6(2) . . ?
C8 C9 C10 122.2(2) . . ?
C15 C10 C11 118.3(2) . . ?
C15 C10 C9 119.6(2) . . ?
C11 C10 C9 122.1(2) . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
C12 C13 C14 119.4(3) . . ?
C12 C13 H13A 120.3 . . ?
C14 C13 H13A 120.3 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C14 C15 C10 120.4(3) . . ?
C14 C15 H15A 119.8 . . ?
C10 C15 H15A 119.8 . . ?
O1 C16 O2 123.6(3) . . ?
O1 C16 C1 123.2(3) . . ?
O2 C16 C1 113.2(2) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 118.8(3) . . ?
C19 C18 C2 121.2(2) . . ?
C23 C18 C2 120.0(2) . . ?
C20 C19 C18 120.7(3) . . ?
C20 C19 H19A 119.6 . . ?
C18 C19 H19A 119.6 . . ?
C21 C20 C19 119.8(3) . . ?
C21 C20 H20A 120.1 . . ?
C19 C20 H20A 120.1 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21A 119.9 . . ?
C20 C21 H21A 119.9 . . ?
C21 C22 C23 120.5(3) . . ?
C21 C22 H22A 119.7 . . ?
C23 C22 H22A 119.7 . . ?
C22 C23 C18 120.0(3) . . ?
C22 C23 H23A 120.0 . . ?
C18 C23 H23A 120.0 . . ?

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
C9 N C1 C2 -4.0(4) . . . . ?
C9 N C1 C16 173.7(2) . . . . ?
N C1 C2 C3 2.5(4) . . . . ?
C16 C1 C2 C3 -175.1(2) . . . . ?
N C1 C2 C18 -176.3(2) . . . . ?
C16 C1 C2 C18 6.1(4) . . . . ?
C1 C2 C3 C4 -177.2(3) . . . . ?
C18 C2 C3 C4 1.6(4) . . . . ?
C1 C2 C3 C8 3.1(4) . . . . ?
C18 C2 C3 C8 -178.2(2) . . . . ?
C8 C3 C4 C5 2.2(4) . . . . ?
C2 C3 C4 C5 -177.6(3) . . . . ?
C3 C4 C5 C6 2.4(5) . . . . ?
C4 C5 C6 C7 -3.2(5) . . . . ?
C5 C6 C7 C8 -0.6(5) . . . . ?
C4 C3 C8 C7 -5.8(4) . . . . ?
C2 C3 C8 C7 174.0(2) . . . . ?
C4 C3 C8 C9 173.4(3) . . . . ?
C2 C3 C8 C9 -6.8(4) . . . . ?
C6 C7 C8 C3 5.1(4) . . . . ?
C6 C7 C8 C9 -174.1(3) . . . . ?
C1 N C9 C8 -0.1(4) . . . . ?
C1 N C9 C10 179.9(2) . . . . ?
C3 C8 C9 N 5.4(4) . . . . ?
C7 C8 C9 N -175.3(3) . . . . ?
C3 C8 C9 C10 -174.6(2) . . . . ?
C7 C8 C9 C10 4.6(4) . . . . ?
N C9 C10 C15 45.1(3) . . . . ?
C8 C9 C10 C15 -134.9(3) . . . . ?
N C9 C10 C11 -134.6(3) . . . . ?
C8 C9 C10 C11 45.4(4) . . . . ?
C15 C10 C11 C12 2.4(4) . . . . ?
C9 C10 C11 C12 -177.9(3) . . . . ?
C10 C11 C12 C13 -1.0(5) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C12 C13 C14 C15 0.9(4) . . . . ?
C13 C14 C15 C10 0.6(4) . . . . ?
C11 C10 C15 C14 -2.2(4) . . . . ?
C9 C10 C15 C14 178.1(2) . . . . ?
C17 O2 C16 O1 -1.8(4) . . . . ?
C17 O2 C16 C1 178.7(2) . . . . ?
N C1 C16 O1 -127.5(3) . . . . ?
C2 C1 C16 O1 50.3(4) . . . . ?
N C1 C16 O2 51.9(3) . . . . ?
C2 C1 C16 O2 -130.2(3) . . . . ?
C1 C2 C18 C19 -106.6(3) . . . . ?
C3 C2 C18 C19 74.7(4) . . . . ?
C1 C2 C18 C23 74.6(4) . . . . ?
C3 C2 C18 C23 -104.1(3) . . . . ?
C23 C18 C19 C20 0.3(4) . . . . ?
C2 C18 C19 C20 -178.5(3) . . . . ?
C18 C19 C20 C21 0.0(5) . . . . ?
C19 C20 C21 C22 -0.2(5) . . . . ?
C20 C21 C22 C23 0.1(5) . . . . ?
C21 C22 C23 C18 0.1(5) . . . . ?
C19 C18 C23 C22 -0.3(4) . . . . ?
C2 C18 C23 C22 178.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 985962'
