# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013


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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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. 
# 
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#  fide research purposes only. It may contain copyright material 
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#  except for the purpose of generating routine backup copies 
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#  data retrieval see:
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data_H:\Report\2d\2d.CIF
_database_code_depnum_ccdc_archive 'CCDC 917397'
#TrackingRef '16405_web_deposit_cif_file_0_ChunhaoYang_1356398238.20120129.CIF'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H11 N O'
_chemical_formula_weight         245.27
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                   7.7325(3)
_cell_length_b                   8.8630(3)
_cell_length_c                   9.8596(3)
_cell_angle_alpha                82.255(2)
_cell_angle_beta                 68.663(2)
_cell_angle_gamma                78.619(2)
_cell_volume                     615.55(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6169
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      54.87
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6526
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_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            11852
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         31.20
_reflns_number_total             3842
_reflns_number_gt                3285
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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^)+(0.0786P)^2^+0.0000P] 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       0.0039(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns         3842
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1725
_refine_ls_wR_factor_gt          0.1646
_refine_ls_goodness_of_fit_ref   1.634
_refine_ls_restrained_S_all      1.634
_refine_ls_shift/su_max          0.001
_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
O1 O 0.26497(14) 0.90450(10) 1.03027(9) 0.0257(2) Uani 1 1 d . . .
N1 N 0.24589(17) 0.59957(11) 0.53598(12) 0.0249(3) Uani 1 1 d . . .
C1 C 0.16114(18) 1.23874(13) 0.56968(12) 0.0204(3) Uani 1 1 d . . .
H1 H 0.1369 1.3331 0.5205 0.024 Uiso 1 1 calc R . .
C2 C 0.32266(17) 1.20196(12) 0.60512(12) 0.0193(2) Uani 1 1 d . . .
H6 H 0.4080 1.2709 0.5758 0.023 Uiso 1 1 calc R . .
C3 C 0.36111(16) 1.06357(12) 0.68402(12) 0.0172(2) Uani 1 1 d . . .
C4 C 0.23103(16) 0.95998(12) 0.72364(12) 0.0156(2) Uani 1 1 d . . .
C5 C 0.25246(16) 0.81410(12) 0.81134(12) 0.0168(2) Uani 1 1 d . . .
C6 C 0.26089(17) 0.79965(13) 0.96455(13) 0.0184(2) Uani 1 1 d . . .
C7 C 0.25840(16) 0.63338(13) 1.01629(12) 0.0184(2) Uani 1 1 d . . .
C8 C 0.26098(18) 0.55637(14) 1.14704(13) 0.0227(3) Uani 1 1 d . . .
H10 H 0.2655 0.6083 1.2213 0.027 Uiso 1 1 calc R . .
C9 C 0.25665(19) 0.39731(14) 1.16444(13) 0.0244(3) Uani 1 1 d . . .
H2 H 0.2586 0.3428 1.2515 0.029 Uiso 1 1 calc R . .
C10 C 0.24942(18) 0.32017(13) 1.05370(13) 0.0229(3) Uani 1 1 d . . .
H3 H 0.2475 0.2145 1.0673 0.027 Uiso 1 1 calc R . .
C11 C 0.24493(17) 0.39925(13) 0.92112(13) 0.0198(2) Uani 1 1 d . . .
H11 H 0.2386 0.3480 0.8471 0.024 Uiso 1 1 calc R . .
C12 C 0.25018(16) 0.55594(12) 0.90481(12) 0.0169(2) Uani 1 1 d . . .
C13 C 0.24731(16) 0.67063(12) 0.78095(12) 0.0167(2) Uani 1 1 d . . .
C14 C 0.03516(18) 1.13506(13) 0.60738(13) 0.0204(2) Uani 1 1 d . . .
H4 H -0.0723 1.1587 0.5820 0.024 Uiso 1 1 calc R . .
C15 C 0.07101(17) 0.99629(13) 0.68303(12) 0.0190(2) Uani 1 1 d . . .
H5 H -0.0123 0.9261 0.7073 0.023 Uiso 1 1 calc R . .
C16 C 0.53869(18) 1.02909(14) 0.71874(14) 0.0232(3) Uani 1 1 d . . .
H9 H 0.6400 1.0619 0.6363 0.035 Uiso 1 1 calc R . .
H7 H 0.5674 0.9201 0.7404 0.035 Uiso 1 1 calc R . .
H8 H 0.5224 1.0832 0.8017 0.035 Uiso 1 1 calc R . .
C17 C 0.24406(17) 0.63179(12) 0.64555(12) 0.0187(2) Uani 1 1 d . . .
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 0.0330(5) 0.0236(4) 0.0222(5) -0.0065(3) -0.0087(4) -0.0070(4)
N1 0.0364(6) 0.0189(5) 0.0236(5) -0.0003(4) -0.0148(5) -0.0061(4)
C1 0.0279(6) 0.0163(5) 0.0172(5) -0.0009(4) -0.0082(5) -0.0037(4)
C2 0.0233(6) 0.0165(5) 0.0182(5) -0.0021(4) -0.0050(4) -0.0072(4)
C3 0.0173(5) 0.0172(5) 0.0168(5) -0.0041(4) -0.0038(4) -0.0040(4)
C4 0.0167(5) 0.0135(4) 0.0162(5) -0.0029(4) -0.0047(4) -0.0026(4)
C5 0.0164(5) 0.0166(5) 0.0175(5) -0.0014(4) -0.0054(4) -0.0038(4)
C6 0.0174(5) 0.0191(5) 0.0189(5) -0.0031(4) -0.0059(4) -0.0032(4)
C7 0.0181(5) 0.0196(5) 0.0170(5) -0.0025(4) -0.0055(4) -0.0019(4)
C8 0.0234(6) 0.0266(6) 0.0170(6) -0.0023(4) -0.0067(5) -0.0015(5)
C9 0.0253(6) 0.0255(6) 0.0174(6) 0.0040(4) -0.0050(5) -0.0010(5)
C10 0.0228(6) 0.0188(5) 0.0224(6) 0.0041(4) -0.0045(5) -0.0028(4)
C11 0.0210(6) 0.0181(5) 0.0188(6) 0.0006(4) -0.0055(5) -0.0042(4)
C12 0.0158(5) 0.0182(5) 0.0164(5) 0.0004(4) -0.0053(4) -0.0037(4)
C13 0.0179(5) 0.0159(5) 0.0165(5) 0.0000(4) -0.0059(4) -0.0042(4)
C14 0.0214(6) 0.0194(5) 0.0224(6) -0.0020(4) -0.0104(5) -0.0022(4)
C15 0.0189(6) 0.0180(5) 0.0211(6) -0.0012(4) -0.0072(4) -0.0046(4)
C16 0.0200(6) 0.0241(6) 0.0274(6) -0.0022(4) -0.0085(5) -0.0068(5)
C17 0.0239(6) 0.0136(5) 0.0200(6) 0.0017(4) -0.0092(5) -0.0051(4)
_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 C6 1.2137(13) . ?
N1 C17 1.1487(15) . ?
C1 C2 1.3836(18) . ?
C1 C14 1.3890(16) . ?
C1 H1 0.9300 . ?
C2 C3 1.4019(15) . ?
C2 H6 0.9300 . ?
C3 C4 1.4103(14) . ?
C3 C16 1.4981(17) . ?
C4 C15 1.4013(16) . ?
C4 C5 1.4715(15) . ?
C5 C13 1.3563(14) . ?
C5 C6 1.5228(16) . ?
C6 C7 1.4945(15) . ?
C7 C8 1.3800(16) . ?
C7 C12 1.3982(15) . ?
C8 C9 1.4026(16) . ?
C8 H10 0.9300 . ?
C9 C10 1.3868(17) . ?
C9 H2 0.9300 . ?
C10 C11 1.4063(15) . ?
C10 H3 0.9300 . ?
C11 C12 1.3833(14) . ?
C11 H11 0.9300 . ?
C12 C13 1.4837(15) . ?
C13 C17 1.4328(15) . ?
C14 C15 1.3836(15) . ?
C14 H4 0.9300 . ?
C15 H5 0.9300 . ?
C16 H9 0.9600 . ?
C16 H7 0.9600 . ?
C16 H8 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C14 120.16(10) . . ?
C2 C1 H1 119.9 . . ?
C14 C1 H1 119.9 . . ?
C1 C2 C3 121.76(10) . . ?
C1 C2 H6 119.1 . . ?
C3 C2 H6 119.1 . . ?
C2 C3 C4 117.64(11) . . ?
C2 C3 C16 119.56(10) . . ?
C4 C3 C16 122.77(10) . . ?
C15 C4 C3 120.07(10) . . ?
C15 C4 C5 117.35(10) . . ?
C3 C4 C5 122.56(10) . . ?
C13 C5 C4 127.70(10) . . ?
C13 C5 C6 106.61(9) . . ?
C4 C5 C6 125.31(9) . . ?
O1 C6 C7 127.95(11) . . ?
O1 C6 C5 125.90(11) . . ?
C7 C6 C5 106.13(9) . . ?
C8 C7 C12 121.21(10) . . ?
C8 C7 C6 130.95(10) . . ?
C12 C7 C6 107.84(10) . . ?
C7 C8 C9 117.93(11) . . ?
C7 C8 H10 121.0 . . ?
C9 C8 H10 121.0 . . ?
C10 C9 C8 120.94(11) . . ?
C10 C9 H2 119.5 . . ?
C8 C9 H2 119.5 . . ?
C9 C10 C11 121.01(11) . . ?
C9 C10 H3 119.5 . . ?
C11 C10 H3 119.5 . . ?
C12 C11 C10 117.59(11) . . ?
C12 C11 H11 121.2 . . ?
C10 C11 H11 121.2 . . ?
C11 C12 C7 121.32(11) . . ?
C11 C12 C13 130.83(10) . . ?
C7 C12 C13 107.85(9) . . ?
C5 C13 C17 124.92(10) . . ?
C5 C13 C12 111.57(10) . . ?
C17 C13 C12 123.49(9) . . ?
C15 C14 C1 119.37(11) . . ?
C15 C14 H4 120.3 . . ?
C1 C14 H4 120.3 . . ?
C14 C15 C4 120.95(10) . . ?
C14 C15 H5 119.5 . . ?
C4 C15 H5 119.5 . . ?
C3 C16 H9 109.5 . . ?
C3 C16 H7 109.5 . . ?
H9 C16 H7 109.5 . . ?
C3 C16 H8 109.5 . . ?
H9 C16 H8 109.5 . . ?
H7 C16 H8 109.5 . . ?
N1 C17 C13 178.41(14) . . ?
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
C14 C1 C2 C3 -2.46(18) . . . . ?
C1 C2 C3 C4 1.51(17) . . . . ?
C1 C2 C3 C16 179.65(11) . . . . ?
C2 C3 C4 C15 0.58(16) . . . . ?
C16 C3 C4 C15 -177.50(10) . . . . ?
C2 C3 C4 C5 -177.55(10) . . . . ?
C16 C3 C4 C5 4.38(17) . . . . ?
C15 C4 C5 C13 53.30(17) . . . . ?
C3 C4 C5 C13 -128.53(13) . . . . ?
C15 C4 C5 C6 -118.67(12) . . . . ?
C3 C4 C5 C6 59.51(16) . . . . ?
C13 C5 C6 O1 -179.11(12) . . . . ?
C4 C5 C6 O1 -5.74(19) . . . . ?
C13 C5 C6 C7 -0.42(13) . . . . ?
C4 C5 C6 C7 172.95(10) . . . . ?
O1 C6 C7 C8 -0.4(2) . . . . ?
C5 C6 C7 C8 -179.05(12) . . . . ?
O1 C6 C7 C12 178.90(12) . . . . ?
C5 C6 C7 C12 0.25(13) . . . . ?
C12 C7 C8 C9 0.51(18) . . . . ?
C6 C7 C8 C9 179.73(12) . . . . ?
C7 C8 C9 C10 -0.19(19) . . . . ?
C8 C9 C10 C11 -0.44(19) . . . . ?
C9 C10 C11 C12 0.74(18) . . . . ?
C10 C11 C12 C7 -0.42(18) . . . . ?
C10 C11 C12 C13 -179.90(11) . . . . ?
C8 C7 C12 C11 -0.21(18) . . . . ?
C6 C7 C12 C11 -179.59(11) . . . . ?
C8 C7 C12 C13 179.38(11) . . . . ?
C6 C7 C12 C13 0.00(13) . . . . ?
C4 C5 C13 C17 8.7(2) . . . . ?
C6 C5 C13 C17 -178.15(11) . . . . ?
C4 C5 C13 C12 -172.73(11) . . . . ?
C6 C5 C13 C12 0.44(13) . . . . ?
C11 C12 C13 C5 179.25(13) . . . . ?
C7 C12 C13 C5 -0.29(14) . . . . ?
C11 C12 C13 C17 -2.1(2) . . . . ?
C7 C12 C13 C17 178.32(11) . . . . ?
C2 C1 C14 C15 1.25(18) . . . . ?
C1 C14 C15 C4 0.84(18) . . . . ?
C3 C4 C15 C14 -1.75(17) . . . . ?
C5 C4 C15 C14 176.46(10) . . . . ?
C5 C13 C17 N1 97(4) . . . . ?
C12 C13 C17 N1 -81(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        31.20
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.061