# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_HL
_database_code_depnum_ccdc_archive 'CCDC 1054382'
_audit_update_record             
;
2015-03-16 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 N O'
_chemical_formula_weight         285.33

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           ?
_symmetry_space_group_name_H-M   ?

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                   16.0198(4)
_cell_length_b                   8.2129(2)
_cell_length_c                   11.1102(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.0470(10)
_cell_angle_gamma                90.00
_cell_volume                     1450.72(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    155(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      155(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24393
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         27.64
_reflns_number_total             3366
_reflns_number_gt                2500
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0761P)²+0.4825P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3366
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1664
_refine_ls_wR_factor_gt          0.1494
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 0.42599(9) 0.16716(17) 0.07408(13) 0.0523(4) Uani 1 1 d . . .
O1 O 0.31439(10) 0.29648(19) -0.08557(14) 0.0734(4) Uani 1 1 d . . .
C1 C 0.11119(12) 0.1623(3) -0.0145(2) 0.0691(6) Uani 1 1 d . . .
H1 H 0.0535 0.1770 -0.0441 0.083 Uiso 1 1 calc R . .
C2 C 0.17149(12) 0.2403(3) -0.07015(18) 0.0644(5) Uani 1 1 d . . .
H12 H 0.1553 0.3089 -0.1379 0.077 Uiso 1 1 calc R . .
9C20 C 0.25601(11) 0.2201(2) -0.02840(16) 0.0512(4) Uani 1 1 d . . .
C4 C 0.27945(10) 0.1202(2) 0.07267(15) 0.0477(4) Uani 1 1 d . . .
C5 C 0.36669(10) 0.0971(2) 0.11969(16) 0.0512(4) Uani 1 1 d . . .
H11 H 0.3802 0.0269 0.1872 0.061 Uiso 1 1 calc R . .
C6 C 0.51247(11) 0.1443(2) 0.12140(16) 0.0498(4) Uani 1 1 d . . .
C110 C 0.56948(11) 0.2319(2) 0.06482(16) 0.0521(4) Uani 1 1 d . . .
H10 H 0.5510 0.3023 -0.0009 0.063 Uiso 1 1 calc R . .
C8 C 0.65490(11) 0.2157(2) 0.10544(15) 0.0495(4) Uani 1 1 d . . .
C9 C 0.68216(11) 0.1125(2) 0.20125(15) 0.0486(4) Uani 1 1 d . . .
C10 C 0.77450(10) 0.1211(2) 0.22291(15) 0.0512(4) Uani 1 1 d . . .
C11 C 0.83181(12) 0.0428(3) 0.30740(18) 0.0631(5) Uani 1 1 d . . .
H5 H 0.8134 -0.0332 0.3630 0.076 Uiso 1 1 calc R . .
C12 C 0.91627(13) 0.0781(3) 0.3088(2) 0.0743(6) Uani 1 1 d . . .
H2 H 0.9563 0.0265 0.3666 0.089 Uiso 1 1 calc R . .
C13 C 0.13309(13) 0.0631(3) 0.0838(2) 0.0713(6) Uani 1 1 d . . .
H14 H 0.0908 0.0089 0.1216 0.086 Uiso 1 1 calc R . .
C14 C 0.21642(12) 0.0427(3) 0.12704(18) 0.0628(5) Uani 1 1 d . . .
H13 H 0.2314 -0.0256 0.1953 0.075 Uiso 1 1 calc R . .
C15 C 0.72894(12) 0.2969(2) 0.05694(18) 0.0606(5) Uani 1 1 d . . .
H8 H 0.7322 0.2660 -0.0285 0.073 Uiso 1 1 calc R . .
H9 H 0.7257 0.4169 0.0630 0.073 Uiso 1 1 calc R . .
C16 C 0.80241(12) 0.2300(2) 0.14003(17) 0.0571(5) Uani 1 1 d . . .
C17 C 0.88676(13) 0.2623(3) 0.1430(2) 0.0731(6) Uani 1 1 d . . .
H7 H 0.9059 0.3365 0.0868 0.088 Uiso 1 1 calc R . .
C18 C 0.94304(13) 0.1869(3) 0.2276(2) 0.0770(7) Uani 1 1 d . . .
H6 H 1.0013 0.2099 0.2303 0.092 Uiso 1 1 calc R . .
C19 C 0.62493(12) 0.0255(2) 0.25773(19) 0.0641(5) Uani 1 1 d . . .
H4 H 0.6436 -0.0449 0.3234 0.077 Uiso 1 1 calc R . .
C20 C 0.53943(12) 0.0409(2) 0.21818(19) 0.0632(5) Uani 1 1 d . . .
H3 H 0.4995 -0.0187 0.2570 0.076 Uiso 1 1 calc R . .
H15 H 0.3690(16) 0.267(3) -0.042(2) 0.093(8) Uiso 1 1 d . . .


_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 C5 1.268(2) . ?
N1 C6 1.432(2) . ?
O1 9C20 1.348(2) . ?
O1 H15 0.98(3) . ?
C1 C2 1.368(3) . ?
C1 C13 1.373(3) . ?
C1 H1 0.9500 . ?
C2 9C20 1.387(3) . ?
C2 H12 0.9500 . ?
9C20 C4 1.404(2) . ?
C4 C14 1.392(2) . ?
C4 C5 1.443(2) . ?
C5 H11 0.9500 . ?
C6 C110 1.374(2) . ?
C6 C20 1.396(3) . ?
C110 C8 1.394(2) . ?
C110 H10 0.9500 . ?
C8 C9 1.389(2) . ?
C8 C15 1.516(2) . ?
C9 C19 1.373(2) . ?
C9 C10 1.471(2) . ?
C10 C11 1.388(3) . ?
C10 C16 1.396(3) . ?
C11 C12 1.382(3) . ?
C11 H5 0.9500 . ?
C12 C18 1.375(3) . ?
C12 H2 0.9500 . ?
C13 C14 1.372(3) . ?
C13 H14 0.9500 . ?
C14 H13 0.9500 . ?
C15 C16 1.508(3) . ?
C15 H8 0.9900 . ?
C15 H9 0.9900 . ?
C16 C17 1.373(3) . ?
C17 C18 1.368(3) . ?
C17 H7 0.9500 . ?
C18 H6 0.9500 . ?
C19 C20 1.392(3) . ?
C19 H4 0.9500 . ?
C20 H3 0.9500 . ?

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
C5 N1 C6 122.13(16) . . ?
9C20 O1 H15 106.6(15) . . ?
C2 C1 C13 120.77(18) . . ?
C2 C1 H1 119.6 . . ?
C13 C1 H1 119.6 . . ?
C1 C2 9C20 120.47(19) . . ?
C1 C2 H12 119.8 . . ?
9C20 C2 H12 119.8 . . ?
O1 9C20 C2 119.46(17) . . ?
O1 9C20 C4 121.06(16) . . ?
C2 9C20 C4 119.48(17) . . ?
C14 C4 9C20 118.48(16) . . ?
C14 C4 C5 120.30(16) . . ?
9C20 C4 C5 121.22(16) . . ?
N1 C5 C4 122.37(16) . . ?
N1 C5 H11 118.8 . . ?
C4 C5 H11 118.8 . . ?
C110 C6 C20 120.69(17) . . ?
C110 C6 N1 115.51(15) . . ?
C20 C6 N1 123.80(16) . . ?
C6 C110 C8 118.90(16) . . ?
C6 C110 H10 120.6 . . ?
C8 C110 H10 120.6 . . ?
C9 C8 C110 120.70(16) . . ?
C9 C8 C15 110.78(15) . . ?
C110 C8 C15 128.52(16) . . ?
C19 C9 C8 120.20(16) . . ?
C19 C9 C10 131.65(16) . . ?
C8 C9 C10 108.14(15) . . ?
C11 C10 C16 120.26(17) . . ?
C11 C10 C9 131.07(18) . . ?
C16 C10 C9 108.67(15) . . ?
C12 C11 C10 118.5(2) . . ?
C12 C11 H5 120.8 . . ?
C10 C11 H5 120.8 . . ?
C18 C12 C11 120.8(2) . . ?
C18 C12 H2 119.6 . . ?
C11 C12 H2 119.6 . . ?
C14 C13 C1 119.57(19) . . ?
C14 C13 H14 120.2 . . ?
C1 C13 H14 120.2 . . ?
C13 C14 C4 121.21(19) . . ?
C13 C14 H13 119.4 . . ?
C4 C14 H13 119.4 . . ?
C16 C15 C8 102.01(15) . . ?
C16 C15 H8 111.4 . . ?
C8 C15 H8 111.4 . . ?
C16 C15 H9 111.4 . . ?
C8 C15 H9 111.4 . . ?
H8 C15 H9 109.2 . . ?
C17 C16 C10 120.11(19) . . ?
C17 C16 C15 129.51(19) . . ?
C10 C16 C15 110.37(16) . . ?
C18 C17 C16 119.5(2) . . ?
C18 C17 H7 120.2 . . ?
C16 C17 H7 120.2 . . ?
C17 C18 C12 120.8(2) . . ?
C17 C18 H6 119.6 . . ?
C12 C18 H6 119.6 . . ?
C9 C19 C20 119.63(17) . . ?
C9 C19 H4 120.2 . . ?
C20 C19 H4 120.2 . . ?
C19 C20 C6 119.88(17) . . ?
C19 C20 H3 120.1 . . ?
C6 C20 H3 120.1 . . ?

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
C13 C1 C2 9C20 0.2(3) . . . . ?
C1 C2 9C20 O1 179.18(18) . . . . ?
C1 C2 9C20 C4 -0.8(3) . . . . ?
O1 9C20 C4 C14 -179.18(17) . . . . ?
C2 9C20 C4 C14 0.8(3) . . . . ?
O1 9C20 C4 C5 0.7(3) . . . . ?
C2 9C20 C4 C5 -179.39(16) . . . . ?
C6 N1 C5 C4 179.77(14) . . . . ?
C14 C4 C5 N1 -178.94(17) . . . . ?
9C20 C4 C5 N1 1.2(3) . . . . ?
C5 N1 C6 C110 -178.16(16) . . . . ?
C5 N1 C6 C20 1.9(3) . . . . ?
C20 C6 C110 C8 0.1(3) . . . . ?
N1 C6 C110 C8 -179.77(14) . . . . ?
C6 C110 C8 C9 0.2(2) . . . . ?
C6 C110 C8 C15 179.05(16) . . . . ?
C110 C8 C9 C19 -0.3(3) . . . . ?
C15 C8 C9 C19 -179.41(17) . . . . ?
C110 C8 C9 C10 179.97(15) . . . . ?
C15 C8 C9 C10 0.90(19) . . . . ?
C19 C9 C10 C11 0.2(3) . . . . ?
C8 C9 C10 C11 179.87(18) . . . . ?
C19 C9 C10 C16 -179.52(19) . . . . ?
C8 C9 C10 C16 0.13(19) . . . . ?
C16 C10 C11 C12 1.4(3) . . . . ?
C9 C10 C11 C12 -178.34(18) . . . . ?
C10 C11 C12 C18 -0.7(3) . . . . ?
C2 C1 C13 C14 0.4(3) . . . . ?
C1 C13 C14 C4 -0.4(3) . . . . ?
9C20 C4 C14 C13 -0.2(3) . . . . ?
C5 C4 C14 C13 179.95(18) . . . . ?
C9 C8 C15 C16 -1.48(19) . . . . ?
C110 C8 C15 C16 179.55(17) . . . . ?
C11 C10 C16 C17 -1.1(3) . . . . ?
C9 C10 C16 C17 178.68(17) . . . . ?
C11 C10 C16 C15 179.11(16) . . . . ?
C9 C10 C16 C15 -1.1(2) . . . . ?
C8 C15 C16 C17 -178.2(2) . . . . ?
C8 C15 C16 C10 1.6(2) . . . . ?
C10 C16 C17 C18 0.1(3) . . . . ?
C15 C16 C17 C18 179.8(2) . . . . ?
C16 C17 C18 C12 0.6(3) . . . . ?
C11 C12 C18 C17 -0.3(3) . . . . ?
C8 C9 C19 C20 0.2(3) . . . . ?
C10 C9 C19 C20 179.80(18) . . . . ?
C9 C19 C20 C6 0.1(3) . . . . ?
C110 C6 C20 C19 -0.3(3) . . . . ?
N1 C6 C20 C19 179.61(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.64
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.036
