# 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_I
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C23 H13 N O2'
_chemical_formula_sum            'C23 H13 N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         335.34

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   9.638(6)
_cell_length_b                   7.105(5)
_cell_length_c                   11.862(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.858(11)
_cell_angle_gamma                90
_cell_volume                     808.0(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    836
_cell_measurement_theta_min      2.1654
_cell_measurement_theta_max      23.0076
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       ?
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.6363
_exptl_absorpt_correction_T_max  0.7452

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              'fine focus'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            6011
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         24.17
_diffrn_reflns_theta_full        24.17
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_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.
;

_reflns_number_total             1406
_reflns_number_gt                721
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1835
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_refine_ls_number_reflns         1406
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.007
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.5678(3) 0.25 0.0835(3) 0.0491(9) Uani d S 1 . .
O O1 0.0765(3) 0.25 -0.0254(3) 0.1189(17) Uani d S 1 . .
O O2 0.0314(3) 0.25 0.1896(3) 0.0765(11) Uani d S 1 . .
C C1 0.1502(5) 0.25 0.1671(4) 0.0542(12) Uani d S 1 . .
C C2 0.2701(5) 0.25 0.2535(4) 0.0521(12) Uani d S 1 . .
C C3 0.2474(6) 0.25 0.3675(4) 0.0761(16) Uani d S 1 . .
H H1 0.1565 0.25 0.3874 0.091 Uiso calc SR 1 . .
C C4 0.3560(6) 0.25 0.4500(5) 0.095(2) Uani d S 1 . .
H H2 0.3396 0.25 0.526 0.114 Uiso calc SR 1 . .
C C5 0.4904(6) 0.25 0.4205(4) 0.0921(19) Uani d S 1 . .
H H3 0.5649 0.25 0.4769 0.11 Uiso calc SR 1 . .
C C6 0.5161(5) 0.25 0.3083(4) 0.0687(14) Uani d S 1 . .
H H4 0.6075 0.25 0.2897 0.082 Uiso calc SR 1 . .
C C7 0.4057(4) 0.25 0.2225(4) 0.0500(11) Uani d S 1 . .
C C8 0.4342(4) 0.25 0.1022(3) 0.0449(11) Uani d S 1 . .
C C9 0.3229(4) 0.25 0.0131(3) 0.0446(10) Uani d S 1 . .
C C10 0.1776(5) 0.25 0.0430(4) 0.0576(12) Uiso d S 1 . .
C C11 0.3537(4) 0.25 -0.0980(3) 0.0435(10) Uani d S 1 . .
C C12 0.4955(4) 0.25 -0.1195(3) 0.0447(11) Uani d S 1 . .
C C13 0.5990(4) 0.25 -0.0259(4) 0.0439(10) Uani d S 1 . .
C C14 0.7414(4) 0.25 -0.0441(4) 0.0532(12) Uani d S 1 . .
H H5 0.8097 0.25 0.0172 0.064 Uiso calc SR 1 . .
C C15 0.7783(5) 0.25 -0.1516(4) 0.0564(12) Uani d S 1 . .
H H6 0.8722 0.25 -0.1633 0.068 Uiso calc SR 1 . .
C C16 0.6772(5) 0.25 -0.2446(4) 0.0586(12) Uani d S 1 . .
H H7 0.7042 0.25 -0.3176 0.07 Uiso calc SR 1 . .
C C17 0.5404(5) 0.25 -0.2292(4) 0.0551(12) Uani d S 1 . .
H H8 0.4743 0.25 -0.2921 0.066 Uiso calc SR 1 . .
C C18 0.2439(4) 0.25 -0.1968(3) 0.0472(11) Uani d S 1 . .
C C19 0.1933(4) 0.4172(5) -0.2430(3) 0.0648(10) Uani d . 1 . .
H H9 0.2259 0.5309 -0.2117 0.078 Uiso calc R 1 . .
C C20 0.0934(4) 0.4164(6) -0.3367(3) 0.0778(12) Uani d . 1 . .
H H10 0.0602 0.5295 -0.3684 0.093 Uiso calc R 1 . .
C C21 0.0444(5) 0.25 -0.3817(4) 0.0740(16) Uani d S 1 . .
H H11 -0.023 0.25 -0.4437 0.089 Uiso calc SR 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.036(2) 0.060(2) 0.050(2) 0 -0.0011(17) 0
O1 0.0317(19) 0.269(5) 0.054(2) 0 -0.0048(17) 0
O2 0.041(2) 0.123(3) 0.067(2) 0 0.0142(17) 0
C1 0.040(3) 0.069(3) 0.055(3) 0 0.008(2) 0
C2 0.048(3) 0.065(3) 0.044(3) 0 0.007(2) 0
C3 0.056(3) 0.127(5) 0.046(3) 0 0.008(3) 0
C4 0.063(4) 0.174(6) 0.047(3) 0 0.004(3) 0
C5 0.061(4) 0.168(6) 0.045(3) 0 -0.006(3) 0
C6 0.046(3) 0.109(4) 0.050(3) 0 -0.001(2) 0
C7 0.047(3) 0.059(3) 0.043(3) 0 0.000(2) 0
C8 0.036(3) 0.052(3) 0.045(3) 0 -0.002(2) 0
C9 0.032(2) 0.056(3) 0.045(3) 0 0.001(2) 0
C11 0.035(2) 0.050(2) 0.044(3) 0 -0.003(2) 0
C12 0.040(3) 0.052(3) 0.041(3) 0 -0.001(2) 0
C13 0.032(2) 0.057(3) 0.043(3) 0 0.004(2) 0
C14 0.037(3) 0.072(3) 0.049(3) 0 -0.005(2) 0
C15 0.034(3) 0.081(3) 0.055(3) 0 0.006(2) 0
C16 0.048(3) 0.082(3) 0.047(3) 0 0.006(2) 0
C17 0.042(3) 0.078(3) 0.045(3) 0 0.000(2) 0
C18 0.031(2) 0.068(3) 0.042(3) 0 0.003(2) 0
C19 0.063(2) 0.074(2) 0.056(2) 0.0122(18) -0.0049(18) -0.0002(18)
C20 0.070(3) 0.105(3) 0.057(2) 0.026(2) -0.004(2) 0.013(2)
C21 0.045(3) 0.127(5) 0.047(3) 0 -0.006(2) 0

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C8 . 1.328(5) ?
N1 C13 . 1.361(5) ?
O1 C10 . 1.202(5) ?
O2 C1 . 1.203(5) ?
C1 C2 . 1.464(6) ?
C1 C10 . 1.521(6) ?
C2 C3 . 1.392(6) ?
C2 C7 . 1.393(6) ?
C3 C4 . 1.359(7) ?
C4 C5 . 1.376(7) ?
C5 C6 . 1.378(7) ?
C6 C7 . 1.395(6) ?
C7 C8 . 1.481(6) ?
C8 C9 . 1.427(5) ?
C9 C11 . 1.381(5) ?
C9 C10 . 1.479(6) ?
C11 C12 . 1.415(6) ?
C11 C18 . 1.496(5) ?
C12 C17 . 1.412(6) ?
C12 C13 . 1.415(5) ?
C13 C14 . 1.410(5) ?
C14 C15 . 1.358(6) ?
C15 C16 . 1.396(6) ?
C16 C17 . 1.349(6) ?
C18 C19 . 1.377(4) ?
C18 C19 4_565 1.377(4) ?
C19 C20 . 1.394(5) ?
C20 C21 . 1.362(4) ?
C21 C20 4_565 1.362(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 N1 C13 . . 118.2(4) ?
O2 C1 C2 . . 123.1(4) ?
O2 C1 C10 . . 118.6(4) ?
C2 C1 C10 . . 118.3(4) ?
C3 C2 C7 . . 120.1(4) ?
C3 C2 C1 . . 119.3(4) ?
C7 C2 C1 . . 120.7(4) ?
C4 C3 C2 . . 120.9(5) ?
C3 C4 C5 . . 119.5(5) ?
C4 C5 C6 . . 120.8(5) ?
C5 C6 C7 . . 120.4(5) ?
C6 C7 C2 . . 118.3(4) ?
C6 C7 C8 . . 120.0(4) ?
C2 C7 C8 . . 121.7(4) ?
N1 C8 C9 . . 123.0(4) ?
N1 C8 C7 . . 116.1(4) ?
C9 C8 C7 . . 120.9(4) ?
C11 C9 C8 . . 119.2(4) ?
C11 C9 C10 . . 122.0(4) ?
C8 C9 C10 . . 118.8(4) ?
O1 C10 C9 . . 124.1(4) ?
O1 C10 C1 . . 116.4(4) ?
C9 C10 C1 . . 119.6(4) ?
C9 C11 C12 . . 118.5(4) ?
C9 C11 C18 . . 122.9(4) ?
C12 C11 C18 . . 118.5(4) ?
C17 C12 C11 . . 123.9(4) ?
C17 C12 C13 . . 117.7(4) ?
C11 C12 C13 . . 118.4(4) ?
N1 C13 C14 . . 117.3(4) ?
N1 C13 C12 . . 122.8(4) ?
C14 C13 C12 . . 119.9(4) ?
C15 C14 C13 . . 119.7(4) ?
C14 C15 C16 . . 120.9(4) ?
C17 C16 C15 . . 120.4(4) ?
C16 C17 C12 . . 121.3(4) ?
C19 C18 C19 . 4_565 119.3(4) ?
C19 C18 C11 . . 120.4(2) ?
C19 C18 C11 4_565 . 120.4(2) ?
C18 C19 C20 . . 120.1(3) ?
C21 C20 C19 . . 120.0(4) ?
C20 C21 C20 4_565 . 120.5(5) ?

_database_code_depnum_ccdc_archive 'CCDC 998127'
