# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


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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. 
# 
#  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 
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#  except for the purpose of generating routine backup copies 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
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#  from this site to visualise CIF-encoded structures and 
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data_z
_database_code_depnum_ccdc_archive 'CCDC 888586'
#TrackingRef '12199_web_deposit_cif_file_0_BoChen_1340720439.z.cif'


_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C19 H17 N O2'
_chemical_formula_weight 291.34

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 8.3211(5)
_cell_length_b 9.7981(6)
_cell_length_c 10.1922(6)
_cell_angle_alpha 73.183(2)
_cell_angle_beta 70.006(2)
_cell_angle_gamma 85.591(2)
_cell_volume 747.28(8)
_cell_formula_units_Z 2
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?

_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.31
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.11
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.295
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 308
_exptl_absorpt_coefficient_mu 0.084
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9744
_exptl_absorpt_correction_T_max 0.9908
_exptl_absorpt_process_details ?

_exptl_special_details
;
?
;

_diffrn_ambient_temperature 173(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 ?
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 8766
_diffrn_reflns_av_R_equivalents 0.0222
_diffrn_reflns_av_sigmaI/netI 0.0230
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.22
_diffrn_reflns_theta_max 25.01
_reflns_number_total 2612
_reflns_number_gt 2115
_reflns_threshold_expression >2sigma(I)

_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics ?
_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^)+(0.0431P)^2^+0.2193P] 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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2612
_refine_ls_number_parameters 207
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0494
_refine_ls_R_factor_gt 0.0374
_refine_ls_wR_factor_ref 0.1008
_refine_ls_wR_factor_gt 0.0934
_refine_ls_goodness_of_fit_ref 1.065
_refine_ls_restrained_S_all 1.065
_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
N1 N 0.20027(16) 0.12724(13) 0.76863(14) 0.0333(3) Uani 1 1 d . . .
O1 O 1.35641(14) 0.16667(14) 0.30665(13) 0.0484(3) Uani 1 1 d . . .
O2 O 0.27137(13) 0.36111(10) 0.66387(11) 0.0318(3) Uani 1 1 d . . .
C1 C -0.0298(2) 0.44591(16) 0.84701(16) 0.0312(4) Uani 1 1 d . . .
H1A H 0.0508 0.5167 0.7762 0.037 Uiso 1 1 calc R . .
C2 C -0.1824(2) 0.48541(17) 0.93602(17) 0.0365(4) Uani 1 1 d . . .
H2A H -0.2062 0.5836 0.9256 0.044 Uiso 1 1 calc R . .
C3 C -0.2997(2) 0.38357(18) 1.03936(17) 0.0359(4) Uani 1 1 d . . .
H3A H -0.4044 0.4116 1.0991 0.043 Uiso 1 1 calc R . .
C4 C -0.2650(2) 0.24069(18) 1.05618(17) 0.0364(4) Uani 1 1 d . . .
H4A H -0.3451 0.1704 1.1284 0.044 Uiso 1 1 calc R . .
C5 C -0.11373(19) 0.19993(17) 0.96784(16) 0.0325(4) Uani 1 1 d . . .
H5A H -0.0903 0.1015 0.9794 0.039 Uiso 1 1 calc R . .
C6 C 0.00444(18) 0.30223(15) 0.86208(15) 0.0270(3) Uani 1 1 d . . .
C7 C 0.16174(18) 0.25498(15) 0.76630(15) 0.0267(3) Uani 1 1 d . . .
C8 C 0.36258(19) 0.13167(16) 0.64919(17) 0.0325(4) Uani 1 1 d . . .
H8A H 0.3457 0.0965 0.5729 0.039 Uiso 1 1 calc R . .
H8B H 0.4488 0.0726 0.6855 0.039 Uiso 1 1 calc R . .
C9 C 0.41980(18) 0.29072(15) 0.58911(16) 0.0285(3) Uani 1 1 d . . .
H9A H 0.4420 0.3237 0.4819 0.034 Uiso 1 1 calc R . .
C10 C 0.57523(19) 0.32035(16) 0.62143(16) 0.0302(4) Uani 1 1 d . . .
C11 C 0.74168(19) 0.27854(15) 0.53005(15) 0.0266(3) Uani 1 1 d . . .
C12 C 0.75134(19) 0.19993(16) 0.43334(16) 0.0302(4) Uani 1 1 d . . .
H12A H 0.6491 0.1766 0.4219 0.036 Uiso 1 1 calc R . .
C13 C 0.90655(19) 0.15507(16) 0.35348(16) 0.0310(4) Uani 1 1 d . . .
H13A H 0.9091 0.1007 0.2893 0.037 Uiso 1 1 calc R . .
C14 C 1.05798(19) 0.18896(15) 0.36666(16) 0.0288(3) Uani 1 1 d . . .
C15 C 1.0499(2) 0.27221(17) 0.45874(17) 0.0332(4) Uani 1 1 d . . .
H15A H 1.1527 0.2995 0.4664 0.040 Uiso 1 1 calc R . .
C16 C 0.8958(2) 0.31567(17) 0.53873(16) 0.0317(4) Uani 1 1 d . . .
H16A H 0.8942 0.3719 0.6010 0.038 Uiso 1 1 calc R . .
C17 C 1.2276(2) 0.14082(17) 0.28530(17) 0.0352(4) Uani 1 1 d . . .
C18 C 1.2377(2) 0.0607(2) 0.1780(2) 0.0481(5) Uani 1 1 d . . .
H18A H 1.3569 0.0374 0.1334 0.072 Uiso 1 1 calc R . .
H18B H 1.1943 0.1198 0.1023 0.072 Uiso 1 1 calc R . .
H18C H 1.1683 -0.0275 0.2281 0.072 Uiso 1 1 calc R . .
C19 C 0.5594(3) 0.3721(2) 0.7311(2) 0.0545(5) Uani 1 1 d . . .
H19B H 0.445(3) 0.396(2) 0.790(2) 0.058(6) Uiso 1 1 d . . .
H19A H 0.658(3) 0.388(2) 0.759(2) 0.064(6) Uiso 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
N1 0.0281(7) 0.0285(7) 0.0378(7) -0.0093(6) -0.0045(6) 0.0015(6)
O1 0.0250(6) 0.0699(9) 0.0495(7) -0.0210(7) -0.0088(6) 0.0053(6)
O2 0.0246(6) 0.0252(6) 0.0365(6) -0.0054(5) -0.0021(5) 0.0022(4)
C1 0.0311(8) 0.0307(8) 0.0306(8) -0.0078(6) -0.0097(7) 0.0013(7)
C2 0.0390(9) 0.0310(9) 0.0403(9) -0.0143(7) -0.0124(8) 0.0083(7)
C3 0.0292(9) 0.0456(10) 0.0332(8) -0.0178(7) -0.0065(7) 0.0078(7)
C4 0.0318(9) 0.0384(9) 0.0311(8) -0.0063(7) -0.0030(7) -0.0011(7)
C5 0.0304(8) 0.0304(8) 0.0325(8) -0.0071(7) -0.0070(7) 0.0024(7)
C6 0.0263(8) 0.0299(8) 0.0270(7) -0.0090(6) -0.0114(6) 0.0039(6)
C7 0.0254(8) 0.0256(8) 0.0288(8) -0.0063(6) -0.0099(6) 0.0007(6)
C8 0.0246(8) 0.0299(8) 0.0400(9) -0.0126(7) -0.0054(7) 0.0022(6)
C9 0.0236(8) 0.0290(8) 0.0306(8) -0.0099(6) -0.0058(6) 0.0041(6)
C10 0.0281(8) 0.0282(8) 0.0326(8) -0.0086(6) -0.0077(7) -0.0001(6)
C11 0.0263(8) 0.0233(8) 0.0274(7) -0.0044(6) -0.0078(6) 0.0001(6)
C12 0.0223(8) 0.0340(8) 0.0351(8) -0.0122(7) -0.0082(6) -0.0016(6)
C13 0.0310(8) 0.0294(8) 0.0321(8) -0.0110(6) -0.0076(7) -0.0015(6)
C14 0.0258(8) 0.0275(8) 0.0283(8) -0.0028(6) -0.0074(6) 0.0017(6)
C15 0.0250(8) 0.0405(9) 0.0356(8) -0.0099(7) -0.0125(7) -0.0005(7)
C16 0.0316(9) 0.0347(9) 0.0322(8) -0.0126(7) -0.0124(7) 0.0011(7)
C17 0.0298(9) 0.0353(9) 0.0325(8) -0.0027(7) -0.0066(7) 0.0031(7)
C18 0.0362(10) 0.0571(12) 0.0502(11) -0.0239(9) -0.0083(8) 0.0121(9)
C19 0.0331(11) 0.0840(16) 0.0589(12) -0.0473(12) -0.0083(9) 0.0014(10)

_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
N1 C7 1.2634(19) . ?
N1 C8 1.4704(19) . ?
O1 C17 1.222(2) . ?
O2 C7 1.3674(17) . ?
O2 C9 1.4530(17) . ?
C1 C2 1.388(2) . ?
C1 C6 1.389(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.377(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.380(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.382(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.391(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.475(2) . ?
C8 C9 1.547(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.507(2) . ?
C9 H9A 1.0000 . ?
C10 C19 1.319(2) . ?
C10 C11 1.485(2) . ?
C11 C12 1.395(2) . ?
C11 C16 1.398(2) . ?
C12 C13 1.387(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.394(2) . ?
C14 C17 1.492(2) . ?
C15 C16 1.376(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C18 1.498(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19B 0.99(2) . ?
C19 H19A 0.99(2) . ?

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
C7 N1 C8 106.88(12) . . ?
C7 O2 C9 106.25(10) . . ?
C2 C1 C6 119.60(15) . . ?
C2 C1 H1A 120.2 . . ?
C6 C1 H1A 120.2 . . ?
C3 C2 C1 120.61(15) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C2 C3 C4 119.97(14) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 C5 119.98(15) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 C6 120.36(14) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C1 C6 C5 119.47(14) . . ?
C1 C6 C7 121.60(13) . . ?
C5 C6 C7 118.91(13) . . ?
N1 C7 O2 118.25(13) . . ?
N1 C7 C6 125.89(13) . . ?
O2 C7 C6 115.82(12) . . ?
N1 C8 C9 104.82(11) . . ?
N1 C8 H8A 110.8 . . ?
C9 C8 H8A 110.8 . . ?
N1 C8 H8B 110.8 . . ?
C9 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
O2 C9 C10 110.80(12) . . ?
O2 C9 C8 102.89(11) . . ?
C10 C9 C8 113.04(12) . . ?
O2 C9 H9A 110.0 . . ?
C10 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
C19 C10 C11 123.15(15) . . ?
C19 C10 C9 120.67(15) . . ?
C11 C10 C9 116.05(13) . . ?
C12 C11 C16 117.20(14) . . ?
C12 C11 C10 121.82(13) . . ?
C16 C11 C10 120.98(13) . . ?
C13 C12 C11 121.61(14) . . ?
C13 C12 H12A 119.2 . . ?
C11 C12 H12A 119.2 . . ?
C14 C13 C12 120.49(14) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C13 C14 C15 118.19(14) . . ?
C13 C14 C17 122.47(14) . . ?
C15 C14 C17 119.33(14) . . ?
C16 C15 C14 121.23(14) . . ?
C16 C15 H15A 119.4 . . ?
C14 C15 H15A 119.4 . . ?
C15 C16 C11 121.20(14) . . ?
C15 C16 H16A 119.4 . . ?
C11 C16 H16A 119.4 . . ?
O1 C17 C14 120.03(15) . . ?
O1 C17 C18 120.68(15) . . ?
C14 C17 C18 119.29(14) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19B 120.1(11) . . ?
C10 C19 H19A 123.3(12) . . ?
H19B C19 H19A 116.6(16) . . ?

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
C6 C1 C2 C3 0.3(2) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
C2 C1 C6 C7 177.60(14) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C4 C5 C6 C7 -177.86(14) . . . . ?
C8 N1 C7 O2 -1.18(18) . . . . ?
C8 N1 C7 C6 176.75(13) . . . . ?
C9 O2 C7 N1 -5.19(17) . . . . ?
C9 O2 C7 C6 176.67(12) . . . . ?
C1 C6 C7 N1 -177.24(15) . . . . ?
C5 C6 C7 N1 1.4(2) . . . . ?
C1 C6 C7 O2 0.7(2) . . . . ?
C5 C6 C7 O2 179.34(13) . . . . ?
C7 N1 C8 C9 6.60(16) . . . . ?
C7 O2 C9 C10 -112.56(13) . . . . ?
C7 O2 C9 C8 8.53(14) . . . . ?
N1 C8 C9 O2 -9.17(15) . . . . ?
N1 C8 C9 C10 110.39(14) . . . . ?
O2 C9 C10 C19 15.5(2) . . . . ?
C8 C9 C10 C19 -99.35(19) . . . . ?
O2 C9 C10 C11 -168.55(11) . . . . ?
C8 C9 C10 C11 76.56(16) . . . . ?
C19 C10 C11 C12 167.74(18) . . . . ?
C9 C10 C11 C12 -8.1(2) . . . . ?
C19 C10 C11 C16 -11.7(2) . . . . ?
C9 C10 C11 C16 172.53(13) . . . . ?
C16 C11 C12 C13 2.7(2) . . . . ?
C10 C11 C12 C13 -176.76(14) . . . . ?
C11 C12 C13 C14 -0.7(2) . . . . ?
C12 C13 C14 C15 -1.8(2) . . . . ?
C12 C13 C14 C17 178.80(14) . . . . ?
C13 C14 C15 C16 2.3(2) . . . . ?
C17 C14 C15 C16 -178.24(14) . . . . ?
C14 C15 C16 C11 -0.3(2) . . . . ?
C12 C11 C16 C15 -2.1(2) . . . . ?
C10 C11 C16 C15 177.30(14) . . . . ?
C13 C14 C17 O1 -175.93(15) . . . . ?
C15 C14 C17 O1 4.6(2) . . . . ?
C13 C14 C17 C18 4.0(2) . . . . ?
C15 C14 C17 C18 -175.46(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full 25.01
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max 0.166
_refine_diff_density_min -0.175
_refine_diff_density_rms 0.034