# Electronic Supplementary Material (ESI) for Chemical Science
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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
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#  data retrieval see:
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#  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.
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data_ww

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 N O2'
_chemical_formula_weight         265.30

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   P212121

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

_cell_length_a                   6.4122(19)
_cell_length_b                   12.077(4)
_cell_length_c                   16.676(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1291.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    3033
_cell_measurement_theta_min      3.3737
_cell_measurement_theta_max      25.3328

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9823
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
SSaturn70 CCD (4x4 bin mode) with MicroMax-007
;
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8665
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2272
_reflns_number_gt                2084
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RIGAKU CrystalClear'
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0358P)^2^+0.3542P] where P=(Fo^2^+2Fc^2^)/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   1.7(18)
_refine_ls_number_reflns         2272
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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
O1 O 0.5523(3) -0.18108(14) 0.48511(10) 0.0251(4) Uani 1 1 d . . .
O2 O -0.1197(3) -0.13387(14) 0.72644(10) 0.0259(4) Uani 1 1 d . . .
N1 N 0.7162(3) 0.05242(16) 0.57044(11) 0.0175(5) Uani 1 1 d . . .
C1 C 0.5317(4) 0.01497(19) 0.60387(14) 0.0161(5) Uani 1 1 d . . .
C2 C 0.4443(4) -0.09239(18) 0.60488(13) 0.0162(5) Uani 1 1 d . . .
C3 C 0.2625(4) -0.1064(2) 0.64912(13) 0.0186(5) Uani 1 1 d . . .
H1 H 0.2039 -0.1785 0.6528 0.022 Uiso 1 1 calc R . .
C4 C 0.1611(4) -0.0188(2) 0.68877(14) 0.0186(6) Uani 1 1 d . . .
C5 C 0.2469(4) 0.08732(19) 0.68591(14) 0.0181(5) Uani 1 1 d . . .
H2 H 0.1800 0.1475 0.7120 0.022 Uiso 1 1 calc R . .
C6 C 0.4323(4) 0.10342(19) 0.64407(13) 0.0163(5) Uani 1 1 d . . .
C7 C 0.5608(4) 0.20048(18) 0.63132(13) 0.0163(5) Uani 1 1 d . . .
C8 C 0.5414(4) 0.31139(19) 0.65343(14) 0.0192(5) Uani 1 1 d . . .
H3 H 0.4270 0.3360 0.6849 0.023 Uiso 1 1 calc R . .
C9 C 0.6941(4) 0.3846(2) 0.62802(14) 0.0214(6) Uani 1 1 d . . .
H4 H 0.6821 0.4607 0.6416 0.026 Uiso 1 1 calc R . .
C10 C 0.8653(4) 0.3492(2) 0.58290(14) 0.0224(6) Uani 1 1 d . . .
H5 H 0.9673 0.4016 0.5667 0.027 Uiso 1 1 calc R . .
C11 C 0.8892(4) 0.2391(2) 0.56145(15) 0.0204(6) Uani 1 1 d . . .
H6 H 1.0065 0.2145 0.5316 0.025 Uiso 1 1 calc R . .
C12 C 0.7331(4) 0.16599(19) 0.58563(14) 0.0172(5) Uani 1 1 d . . .
C13 C 0.8672(4) -0.0108(2) 0.52421(14) 0.0213(6) Uani 1 1 d . . .
H7 H 0.8898 -0.0828 0.5498 0.032 Uiso 1 1 calc R . .
H8 H 0.9993 0.0299 0.5219 0.032 Uiso 1 1 calc R . .
H9 H 0.8141 -0.0220 0.4697 0.032 Uiso 1 1 calc R . .
C14 C 0.5283(4) -0.1884(2) 0.55771(15) 0.0196(5) Uani 1 1 d . . .
C15 C 0.5802(4) -0.29098(19) 0.60338(15) 0.0246(6) Uani 1 1 d . . .
H10 H 0.6311 -0.3478 0.5663 0.037 Uiso 1 1 calc R . .
H11 H 0.4551 -0.3181 0.6308 0.037 Uiso 1 1 calc R . .
H12 H 0.6886 -0.2744 0.6431 0.037 Uiso 1 1 calc R . .
C16 C -0.0368(4) -0.0431(2) 0.73126(14) 0.0195(5) Uani 1 1 d . . .
C17 C -0.1349(4) 0.0476(2) 0.78135(15) 0.0229(6) Uani 1 1 d . . .
H13 H -0.2634 0.0198 0.8060 0.034 Uiso 1 1 calc R . .
H14 H -0.1675 0.1111 0.7471 0.034 Uiso 1 1 calc R . .
H15 H -0.0373 0.0704 0.8234 0.034 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0247(10) 0.0301(10) 0.0205(10) -0.0035(8) 0.0000(9) 0.0008(8)
O2 0.0230(10) 0.0274(10) 0.0273(10) -0.0032(8) 0.0031(8) -0.0075(9)
N1 0.0147(10) 0.0191(11) 0.0186(11) -0.0018(8) 0.0010(9) 0.0007(8)
C1 0.0142(12) 0.0203(13) 0.0138(12) 0.0015(10) -0.0004(10) 0.0007(10)
C2 0.0152(12) 0.0191(13) 0.0144(12) 0.0002(10) 0.0007(11) 0.0019(10)
C3 0.0204(13) 0.0173(13) 0.0180(13) 0.0014(10) -0.0026(11) -0.0011(11)
C4 0.0164(13) 0.0226(14) 0.0169(13) 0.0010(11) -0.0003(10) -0.0009(11)
C5 0.0136(12) 0.0235(14) 0.0171(13) 0.0009(10) -0.0014(10) 0.0035(11)
C6 0.0155(12) 0.0197(12) 0.0137(12) 0.0006(10) -0.0035(11) 0.0000(11)
C7 0.0151(12) 0.0198(13) 0.0142(12) 0.0011(10) -0.0016(11) 0.0005(10)
C8 0.0198(13) 0.0224(14) 0.0153(12) 0.0009(10) -0.0002(11) 0.0031(11)
C9 0.0256(14) 0.0176(13) 0.0211(13) 0.0002(11) -0.0026(11) -0.0006(11)
C10 0.0237(13) 0.0241(15) 0.0193(13) 0.0051(11) -0.0021(11) -0.0055(11)
C11 0.0187(13) 0.0264(14) 0.0163(13) 0.0032(11) -0.0002(11) 0.0010(11)
C12 0.0184(12) 0.0174(13) 0.0159(12) 0.0003(10) -0.0007(10) 0.0002(10)
C13 0.0160(12) 0.0260(14) 0.0218(14) -0.0014(11) 0.0032(11) 0.0041(11)
C14 0.0141(12) 0.0230(14) 0.0218(14) -0.0015(11) -0.0027(11) -0.0026(10)
C15 0.0284(15) 0.0195(13) 0.0258(14) -0.0032(11) 0.0006(12) -0.0001(11)
C16 0.0184(13) 0.0250(14) 0.0152(13) 0.0008(11) -0.0033(11) 0.0000(11)
C17 0.0219(14) 0.0252(14) 0.0215(14) -0.0015(11) 0.0039(12) 0.0003(11)

_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 C14 1.224(3) . ?
O2 C16 1.221(3) . ?
N1 C1 1.384(3) . ?
N1 C12 1.399(3) . ?
N1 C13 1.454(3) . ?
C1 C2 1.413(3) . ?
C1 C6 1.413(3) . ?
C2 C3 1.390(3) . ?
C2 C14 1.501(3) . ?
C3 C4 1.406(3) . ?
C3 H1 0.9500 . ?
C4 C5 1.396(3) . ?
C4 C16 1.483(3) . ?
C5 C6 1.392(3) . ?
C5 H2 0.9500 . ?
C6 C7 1.448(3) . ?
C7 C8 1.395(3) . ?
C7 C12 1.406(3) . ?
C8 C9 1.385(3) . ?
C8 H3 0.9500 . ?
C9 C10 1.398(4) . ?
C9 H4 0.9500 . ?
C10 C11 1.385(3) . ?
C10 H5 0.9500 . ?
C11 C12 1.394(3) . ?
C11 H6 0.9500 . ?
C13 H7 0.9800 . ?
C13 H8 0.9800 . ?
C13 H9 0.9800 . ?
C14 C15 1.492(3) . ?
C15 H10 0.9800 . ?
C15 H11 0.9800 . ?
C15 H12 0.9800 . ?
C16 C17 1.514(3) . ?
C17 H13 0.9800 . ?
C17 H14 0.9800 . ?
C17 H15 0.9800 . ?

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 C12 108.3(2) . . ?
C1 N1 C13 127.7(2) . . ?
C12 N1 C13 124.0(2) . . ?
N1 C1 C2 130.1(2) . . ?
N1 C1 C6 109.3(2) . . ?
C2 C1 C6 120.6(2) . . ?
C3 C2 C1 116.8(2) . . ?
C3 C2 C14 119.0(2) . . ?
C1 C2 C14 124.1(2) . . ?
C2 C3 C4 123.1(2) . . ?
C2 C3 H1 118.5 . . ?
C4 C3 H1 118.5 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 C16 122.4(2) . . ?
C3 C4 C16 118.1(2) . . ?
C6 C5 C4 118.8(2) . . ?
C6 C5 H2 120.6 . . ?
C4 C5 H2 120.6 . . ?
C5 C6 C1 121.2(2) . . ?
C5 C6 C7 132.2(2) . . ?
C1 C6 C7 106.60(19) . . ?
C8 C7 C12 119.9(2) . . ?
C8 C7 C6 133.4(2) . . ?
C12 C7 C6 106.67(19) . . ?
C9 C8 C7 117.9(2) . . ?
C9 C8 H3 121.0 . . ?
C7 C8 H3 121.0 . . ?
C8 C9 C10 121.7(2) . . ?
C8 C9 H4 119.2 . . ?
C10 C9 H4 119.2 . . ?
C11 C10 C9 121.3(2) . . ?
C11 C10 H5 119.4 . . ?
C9 C10 H5 119.4 . . ?
C10 C11 C12 117.0(2) . . ?
C10 C11 H6 121.5 . . ?
C12 C11 H6 121.5 . . ?
C11 C12 N1 128.6(2) . . ?
C11 C12 C7 122.2(2) . . ?
N1 C12 C7 109.1(2) . . ?
N1 C13 H7 109.5 . . ?
N1 C13 H8 109.5 . . ?
H7 C13 H8 109.5 . . ?
N1 C13 H9 109.5 . . ?
H7 C13 H9 109.5 . . ?
H8 C13 H9 109.5 . . ?
O1 C14 C15 122.5(2) . . ?
O1 C14 C2 120.5(2) . . ?
C15 C14 C2 117.0(2) . . ?
C14 C15 H10 109.5 . . ?
C14 C15 H11 109.5 . . ?
H10 C15 H11 109.5 . . ?
C14 C15 H12 109.5 . . ?
H10 C15 H12 109.5 . . ?
H11 C15 H12 109.5 . . ?
O2 C16 C4 121.2(2) . . ?
O2 C16 C17 120.3(2) . . ?
C4 C16 C17 118.4(2) . . ?
C16 C17 H13 109.5 . . ?
C16 C17 H14 109.5 . . ?
H13 C17 H14 109.5 . . ?
C16 C17 H15 109.5 . . ?
H13 C17 H15 109.5 . . ?
H14 C17 H15 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C1 C2 -180.0(2) . . . . ?
C13 N1 C1 C2 2.4(4) . . . . ?
C12 N1 C1 C6 -2.6(2) . . . . ?
C13 N1 C1 C6 179.8(2) . . . . ?
N1 C1 C2 C3 175.0(2) . . . . ?
C6 C1 C2 C3 -2.1(3) . . . . ?
N1 C1 C2 C14 -8.7(4) . . . . ?
C6 C1 C2 C14 174.1(2) . . . . ?
C1 C2 C3 C4 2.8(3) . . . . ?
C14 C2 C3 C4 -173.6(2) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C2 C3 C4 C16 177.5(2) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C16 C4 C5 C6 -179.4(2) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 C7 -178.6(2) . . . . ?
N1 C1 C6 C5 -177.41(19) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
N1 C1 C6 C7 2.3(3) . . . . ?
C2 C1 C6 C7 -180.0(2) . . . . ?
C5 C6 C7 C8 -2.8(4) . . . . ?
C1 C6 C7 C8 177.6(2) . . . . ?
C5 C6 C7 C12 178.5(2) . . . . ?
C1 C6 C7 C12 -1.2(3) . . . . ?
C12 C7 C8 C9 0.9(3) . . . . ?
C6 C7 C8 C9 -177.7(2) . . . . ?
C7 C8 C9 C10 -1.2(4) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
C10 C11 C12 N1 178.3(2) . . . . ?
C10 C11 C12 C7 -1.4(3) . . . . ?
C1 N1 C12 C11 -177.9(2) . . . . ?
C13 N1 C12 C11 -0.2(4) . . . . ?
C1 N1 C12 C7 1.8(2) . . . . ?
C13 N1 C12 C7 179.6(2) . . . . ?
C8 C7 C12 C11 0.4(3) . . . . ?
C6 C7 C12 C11 179.4(2) . . . . ?
C8 C7 C12 N1 -179.3(2) . . . . ?
C6 C7 C12 N1 -0.4(3) . . . . ?
C3 C2 C14 O1 121.4(3) . . . . ?
C1 C2 C14 O1 -54.7(3) . . . . ?
C3 C2 C14 C15 -58.7(3) . . . . ?
C1 C2 C14 C15 125.2(3) . . . . ?
C5 C4 C16 O2 172.7(2) . . . . ?
C3 C4 C16 O2 -6.3(3) . . . . ?
C5 C4 C16 C17 -7.4(3) . . . . ?
C3 C4 C16 C17 173.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 940718'