# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c
_database_code_depnum_ccdc_archive 'CCDC 1037574'
_audit_update_record             
;
2014-12-04 deposited with the CCDC.
2015-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 N O'
_chemical_formula_weight         271.30

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           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                   8.3956(6)
_cell_length_b                   21.0394(13)
_cell_length_c                   8.2906(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.859(7)
_cell_angle_gamma                90.00
_cell_volume                     1408.70(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1819
_cell_measurement_theta_min      3.8320
_cell_measurement_theta_max      27.7650

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6770
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         29.17
_reflns_number_total             3104
_reflns_number_gt                2241
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0575P)²+0.1567P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.043(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3104
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.009
_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
N1 N -0.01244(14) 0.61904(5) 0.49860(14) 0.0463(3) Uani 1 1 d . . .
C19 C 0.15502(17) 0.63584(6) 0.53398(17) 0.0466(3) Uani 1 1 d . . .
C18 C -0.08567(16) 0.58459(6) 0.60600(16) 0.0440(3) Uani 1 1 d . . .
C17 C -0.09582(17) 0.64519(6) 0.34346(16) 0.0449(3) Uani 1 1 d . . .
C16 C 0.17890(18) 0.67177(6) 0.40020(19) 0.0501(4) Uani 1 1 d . . .
C15 C -0.18892(17) 0.53331(7) 0.54541(18) 0.0512(4) Uani 1 1 d . . .
H15A H -0.2099 0.5212 0.4336 0.061 Uiso 1 1 calc R . .
C14 C -0.05342(17) 0.60196(7) 0.77334(17) 0.0491(3) Uani 1 1 d . . .
H14A H 0.0151 0.6364 0.8140 0.059 Uiso 1 1 calc R . .
C13 C -0.22713(18) 0.51738(7) 0.81902(19) 0.0523(4) Uani 1 1 d . A .
C12 C -0.12288(18) 0.56816(7) 0.87886(17) 0.0519(4) Uani 1 1 d . . .
H12A H -0.0996 0.5795 0.9913 0.062 Uiso 1 1 calc R . .
C11 C 0.01904(18) 0.67857(6) 0.28003(18) 0.0487(4) Uani 1 1 d . . .
C10 C -0.26011(18) 0.50040(7) 0.6516(2) 0.0552(4) Uani 1 1 d . . .
H10A H -0.3308 0.4665 0.6107 0.066 Uiso 1 1 calc R . .
C9 C -0.26316(19) 0.64346(7) 0.25888(18) 0.0530(4) Uani 1 1 d . . .
H9A H -0.3382 0.6211 0.3014 0.064 Uiso 1 1 calc R . .
C8 C -0.0365(2) 0.71087(7) 0.12848(19) 0.0618(4) Uani 1 1 d . . .
H8A H 0.0375 0.7332 0.0843 0.074 Uiso 1 1 calc R . .
C7 C 0.28632(18) 0.61925(7) 0.6703(2) 0.0565(4) Uani 1 1 d . . .
H7A H 0.2696 0.5954 0.7588 0.068 Uiso 1 1 calc R . .
C6 C 0.4685(2) 0.67520(9) 0.5385(3) 0.0742(5) Uani 1 1 d . . .
H6A H 0.5752 0.6881 0.5416 0.089 Uiso 1 1 calc R . .
C5 C 0.4425(2) 0.63949(8) 0.6693(2) 0.0673(5) Uani 1 1 d . . .
H5A H 0.5325 0.6289 0.7587 0.081 Uiso 1 1 calc R . .
C4 C -0.3137(2) 0.67615(8) 0.1098(2) 0.0636(4) Uani 1 1 d . . .
H4A H -0.4253 0.6761 0.0512 0.076 Uiso 1 1 calc R . .
C3 C -0.2025(2) 0.70922(8) 0.0449(2) 0.0680(5) Uani 1 1 d . . .
H3A H -0.2405 0.7306 -0.0565 0.082 Uiso 1 1 calc R . .
C2 C 0.3387(2) 0.69178(8) 0.4045(2) 0.0667(5) Uani 1 1 d . . .
H2A H 0.3569 0.7161 0.3175 0.080 Uiso 1 1 calc R . .
C1 C -0.3026(2) 0.48360(10) 0.9362(3) 0.0758(5) Uani 1 1 d . . .
O1 O -0.3896(3) 0.43942(10) 0.9040(2) 0.1061(9) Uani 0.784(4) 1 d P A 1
O1' O -0.2914(9) 0.4931(4) 1.0652(8) 0.101(3) Uani 0.216(4) 1 d P A 2

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 0.0461(6) 0.0499(7) 0.0458(6) 0.0029(5) 0.0173(5) -0.0054(5)
C19 0.0484(8) 0.0416(7) 0.0541(8) -0.0068(6) 0.0212(6) -0.0057(6)
C18 0.0443(7) 0.0429(7) 0.0484(7) 0.0024(6) 0.0190(6) 0.0005(6)
C17 0.0539(8) 0.0405(7) 0.0440(7) -0.0010(6) 0.0193(6) 0.0012(6)
C16 0.0578(8) 0.0400(7) 0.0602(8) -0.0070(6) 0.0292(7) -0.0064(6)
C15 0.0566(8) 0.0491(8) 0.0510(8) -0.0045(6) 0.0198(6) -0.0058(6)
C14 0.0524(8) 0.0487(8) 0.0487(8) -0.0027(6) 0.0179(6) -0.0055(6)
C13 0.0526(8) 0.0509(8) 0.0592(8) 0.0104(7) 0.0252(7) 0.0043(7)
C12 0.0562(8) 0.0567(9) 0.0459(7) 0.0033(6) 0.0191(6) 0.0037(7)
C11 0.0648(9) 0.0364(7) 0.0529(8) -0.0015(6) 0.0297(7) -0.0015(6)
C10 0.0558(8) 0.0455(8) 0.0684(10) -0.0006(7) 0.0238(7) -0.0087(6)
C9 0.0569(9) 0.0530(9) 0.0517(8) -0.0010(7) 0.0195(7) 0.0026(7)
C8 0.0898(12) 0.0436(8) 0.0612(9) 0.0048(7) 0.0363(9) -0.0014(8)
C7 0.0521(8) 0.0571(9) 0.0600(9) -0.0053(7) 0.0150(7) -0.0033(7)
C6 0.0544(10) 0.0756(12) 0.0994(14) -0.0222(10) 0.0328(10) -0.0183(8)
C5 0.0503(9) 0.0695(11) 0.0804(11) -0.0170(9) 0.0149(8) -0.0046(8)
C4 0.0723(10) 0.0622(10) 0.0546(9) 0.0026(8) 0.0144(8) 0.0146(8)
C3 0.0955(14) 0.0553(9) 0.0542(9) 0.0108(7) 0.0218(9) 0.0148(9)
C2 0.0714(11) 0.0555(10) 0.0865(12) -0.0084(8) 0.0441(10) -0.0164(8)
C1 0.0767(12) 0.0774(13) 0.0841(14) 0.0169(11) 0.0404(10) -0.0049(10)
O1 0.1223(16) 0.1081(16) 0.1005(15) 0.0065(11) 0.0519(12) -0.0566(13)
O1' 0.132(6) 0.122(6) 0.069(5) 0.029(4) 0.059(4) 0.022(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
N1 C17 1.3982(17) . ?
N1 C19 1.4009(17) . ?
N1 C18 1.4126(17) . ?
C19 C7 1.391(2) . ?
C19 C16 1.401(2) . ?
C18 C15 1.3891(19) . ?
C18 C14 1.3879(18) . ?
C17 C9 1.389(2) . ?
C17 C11 1.4060(19) . ?
C16 C2 1.398(2) . ?
C16 C11 1.443(2) . ?
C15 C10 1.378(2) . ?
C14 C12 1.3747(19) . ?
C13 C12 1.384(2) . ?
C13 C10 1.386(2) . ?
C13 C1 1.479(2) . ?
C11 C8 1.392(2) . ?
C9 C4 1.376(2) . ?
C8 C3 1.377(2) . ?
C7 C5 1.381(2) . ?
C6 C2 1.371(3) . ?
C6 C5 1.385(3) . ?
C4 C3 1.386(2) . ?
C1 O1' 1.067(6) . ?
C1 O1 1.167(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
C17 N1 C19 108.35(11) . . ?
C17 N1 C18 125.95(11) . . ?
C19 N1 C18 125.61(11) . . ?
C7 C19 N1 129.35(13) . . ?
C7 C19 C16 121.73(13) . . ?
N1 C19 C16 108.84(12) . . ?
C15 C18 C14 119.87(13) . . ?
C15 C18 N1 120.44(12) . . ?
C14 C18 N1 119.69(12) . . ?
C9 C17 N1 129.59(13) . . ?
C9 C17 C11 121.80(13) . . ?
N1 C17 C11 108.57(12) . . ?
C2 C16 C19 119.10(15) . . ?
C2 C16 C11 133.87(15) . . ?
C19 C16 C11 107.02(12) . . ?
C10 C15 C18 119.72(13) . . ?
C12 C14 C18 119.94(13) . . ?
C12 C13 C10 119.44(13) . . ?
C12 C13 C1 118.55(15) . . ?
C10 C13 C1 121.99(16) . . ?
C14 C12 C13 120.52(13) . . ?
C8 C11 C17 119.13(14) . . ?
C8 C11 C16 133.64(14) . . ?
C17 C11 C16 107.20(12) . . ?
C15 C10 C13 120.50(13) . . ?
C4 C9 C17 117.48(14) . . ?
C3 C8 C11 119.01(15) . . ?
C5 C7 C19 117.41(15) . . ?
C2 C6 C5 120.79(16) . . ?
C7 C5 C6 121.71(17) . . ?
C9 C4 C3 121.64(16) . . ?
C8 C3 C4 120.94(15) . . ?
C6 C2 C16 119.26(16) . . ?
O1' C1 O1 104.9(5) . . ?
O1' C1 C13 129.2(5) . . ?
O1 C1 C13 125.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.816
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.034
