# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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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.
#
data_1

_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           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   8.7226(16)
_cell_length_b                   19.987(4)
_cell_length_c                   9.9442(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.349(3)
_cell_angle_gamma                90.00
_cell_volume                     1579.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9882
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8030
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2783
_reflns_number_gt                1990
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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 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)+(0.0583P)²+0.2895P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2783
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1376
_refine_ls_wR_factor_gt          0.1220
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
O1 O 0.54973(16) 0.23273(6) 0.20973(14) 0.0573(4) Uani 1 1 d . . .
C13 C 0.4208(2) 0.19288(8) 0.2091(2) 0.0480(4) Uani 1 1 d . . .
C16 C 0.1565(2) 0.11223(9) 0.1856(2) 0.0560(5) Uani 1 1 d . . .
C1 C 0.6590(2) 0.26069(9) 0.3440(2) 0.0536(5) Uani 1 1 d . . .
C18 C 0.3675(2) 0.19219(9) 0.3217(2) 0.0550(5) Uani 1 1 d . . .
H18 H 0.4202 0.2188 0.4049 0.066 Uiso 1 1 calc R . .
C14 C 0.3440(3) 0.15392(9) 0.0853(2) 0.0585(5) Uani 1 1 d . . .
H14 H 0.3812 0.1549 0.0101 0.070 Uiso 1 1 calc R . .
O2 O 0.4494(2) 0.41045(7) 0.33421(18) 0.0798(5) Uani 1 1 d . . .
C15 C 0.2120(3) 0.11358(9) 0.0736(2) 0.0619(5) Uani 1 1 d . . .
H15 H 0.1596 0.0870 -0.0097 0.074 Uiso 1 1 calc R . .
C17 C 0.2351(2) 0.15153(10) 0.3092(2) 0.0601(5) Uani 1 1 d . . .
H17 H 0.1982 0.1505 0.3846 0.072 Uiso 1 1 calc R . .
C2 C 0.7815(2) 0.21372(9) 0.4468(2) 0.0558(5) Uani 1 1 d . . .
C8 C 0.6512(3) 0.32583(9) 0.3614(2) 0.0617(5) Uani 1 1 d . . .
H8 H 0.7316 0.3444 0.4472 0.074 Uiso 1 1 calc R . .
C9 C 0.5256(3) 0.37227(10) 0.2562(2) 0.0661(6) Uani 1 1 d . . .
H9 H 0.4389 0.3464 0.1778 0.079 Uiso 1 1 calc R . .
C19 C 0.0204(3) 0.06883(11) 0.1719(3) 0.0705(6) Uani 1 1 d . . .
C3 C 0.8092(3) 0.15137(10) 0.3990(3) 0.0681(6) Uani 1 1 d . . .
H3 H 0.7483 0.1386 0.3014 0.082 Uiso 1 1 calc R . .
C7 C 0.8713(3) 0.23048(11) 0.5939(3) 0.0752(6) Uani 1 1 d . . .
H7 H 0.8513 0.2713 0.6287 0.090 Uiso 1 1 calc R . .
C10 C 0.5995(3) 0.42383(11) 0.1883(3) 0.0823(7) Uani 1 1 d . . .
H10A H 0.7158 0.4335 0.2528 0.099 Uiso 1 1 calc R . .
H10B H 0.5934 0.4089 0.0934 0.099 Uiso 1 1 calc R . .
C4 C 0.9266(3) 0.10839(12) 0.4957(3) 0.0835(7) Uani 1 1 d . . .
H4 H 0.9442 0.0667 0.4627 0.100 Uiso 1 1 calc R . .
C12 C 0.4898(3) 0.48326(11) 0.1717(3) 0.0813(7) Uani 1 1 d . . .
H12A H 0.5477 0.5245 0.1703 0.098 Uiso 1 1 calc R . .
H12B H 0.3867 0.4804 0.0825 0.098 Uiso 1 1 calc R . .
N1 N -0.0875(3) 0.03391(11) 0.1581(3) 0.1014(7) Uani 1 1 d . . .
C11 C 0.4561(4) 0.47872(11) 0.3041(3) 0.0886(8) Uani 1 1 d . . .
H11A H 0.5448 0.5006 0.3867 0.106 Uiso 1 1 calc R . .
H11B H 0.3500 0.5002 0.2871 0.106 Uiso 1 1 calc R . .
C6 C 0.9894(3) 0.18766(14) 0.6891(3) 0.0928(8) Uani 1 1 d . . .
H6 H 1.0502 0.2001 0.7869 0.111 Uiso 1 1 calc R . .
C5 C 1.0183(3) 0.12653(14) 0.6407(4) 0.0905(8) Uani 1 1 d . . .
H5 H 1.0989 0.0977 0.7051 0.109 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 0.0703(8) 0.0559(8) 0.0504(8) -0.0003(6) 0.0298(7) -0.0111(6)
C13 0.0567(10) 0.0423(9) 0.0465(11) 0.0013(8) 0.0227(9) 0.0013(8)
C16 0.0569(11) 0.0499(10) 0.0594(13) -0.0009(9) 0.0223(10) -0.0012(9)
C1 0.0594(10) 0.0516(11) 0.0518(11) -0.0010(9) 0.0249(9) -0.0090(9)
C18 0.0648(11) 0.0529(11) 0.0519(12) -0.0109(8) 0.0287(10) -0.0067(9)
C14 0.0757(12) 0.0569(11) 0.0480(11) -0.0043(9) 0.0307(10) -0.0037(10)
O2 0.0939(11) 0.0730(10) 0.0965(12) 0.0210(8) 0.0633(10) 0.0072(8)
C15 0.0749(13) 0.0552(11) 0.0488(12) -0.0096(9) 0.0185(11) -0.0084(10)
C17 0.0648(12) 0.0647(12) 0.0601(13) -0.0056(10) 0.0351(11) -0.0023(10)
C2 0.0583(10) 0.0518(11) 0.0616(13) 0.0056(9) 0.0290(10) -0.0050(9)
C8 0.0693(12) 0.0519(11) 0.0585(13) 0.0015(9) 0.0209(11) -0.0077(9)
C9 0.0820(14) 0.0528(11) 0.0623(14) 0.0007(10) 0.0287(12) -0.0033(10)
C19 0.0701(13) 0.0645(13) 0.0784(16) -0.0065(11) 0.0322(12) -0.0086(11)
C3 0.0770(13) 0.0627(13) 0.0735(15) 0.0034(11) 0.0401(12) 0.0039(11)
C7 0.0824(14) 0.0656(14) 0.0666(15) 0.0013(11) 0.0196(13) -0.0026(11)
C10 0.1036(17) 0.0814(16) 0.0854(17) 0.0225(13) 0.0627(15) 0.0174(13)
C4 0.0923(17) 0.0692(14) 0.103(2) 0.0190(14) 0.0548(17) 0.0230(13)
C12 0.1066(18) 0.0617(14) 0.0884(18) 0.0124(12) 0.0530(15) -0.0009(12)
N1 0.0924(14) 0.0996(16) 0.119(2) -0.0191(14) 0.0506(14) -0.0368(14)
C11 0.124(2) 0.0611(14) 0.107(2) 0.0078(13) 0.0745(18) 0.0071(14)
C6 0.0882(17) 0.0901(19) 0.0764(18) 0.0143(14) 0.0102(15) 0.0022(14)
C5 0.0768(15) 0.0932(19) 0.098(2) 0.0344(16) 0.0320(16) 0.0216(14)

_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 C13 1.376(2) . ?
O1 C1 1.398(2) . ?
C13 C14 1.375(3) . ?
C13 C18 1.379(3) . ?
C16 C17 1.379(3) . ?
C16 C15 1.386(3) . ?
C16 C19 1.431(3) . ?
C1 C8 1.319(3) . ?
C1 C2 1.473(3) . ?
C18 C17 1.375(3) . ?
C14 C15 1.370(3) . ?
O2 C11 1.403(2) . ?
O2 C9 1.432(2) . ?
C2 C7 1.386(3) . ?
C2 C3 1.390(3) . ?
C8 C9 1.487(3) . ?
C9 C10 1.515(3) . ?
C19 N1 1.134(3) . ?
C3 C4 1.378(3) . ?
C7 C6 1.373(3) . ?
C10 C12 1.491(3) . ?
C4 C5 1.378(4) . ?
C12 C11 1.465(3) . ?
C6 C5 1.374(4) . ?

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
C13 O1 C1 118.03(13) . . ?
C14 C13 O1 115.32(16) . . ?
C14 C13 C18 121.24(17) . . ?
O1 C13 C18 123.42(16) . . ?
C17 C16 C15 119.69(17) . . ?
C17 C16 C19 121.22(19) . . ?
C15 C16 C19 119.09(18) . . ?
C8 C1 O1 117.91(17) . . ?
C8 C1 C2 126.89(18) . . ?
O1 C1 C2 114.98(15) . . ?
C17 C18 C13 118.98(18) . . ?
C15 C14 C13 119.43(18) . . ?
C11 O2 C9 109.46(15) . . ?
C14 C15 C16 120.19(18) . . ?
C18 C17 C16 120.47(18) . . ?
C7 C2 C3 118.39(19) . . ?
C7 C2 C1 120.75(18) . . ?
C3 C2 C1 120.85(19) . . ?
C1 C8 C9 125.95(19) . . ?
O2 C9 C8 108.91(17) . . ?
O2 C9 C10 104.91(16) . . ?
C8 C9 C10 114.36(19) . . ?
N1 C19 C16 178.5(3) . . ?
C4 C3 C2 120.3(2) . . ?
C6 C7 C2 120.9(2) . . ?
C12 C10 C9 102.66(18) . . ?
C3 C4 C5 120.6(2) . . ?
C11 C12 C10 102.05(19) . . ?
O2 C11 C12 107.07(19) . . ?
C7 C6 C5 120.5(3) . . ?
C6 C5 C4 119.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 955471'
