# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_liuy1031
_database_code_depnum_ccdc_archive 'CCDC 1434481'
_audit_update_record             
;
2015-10-31 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;
_audit_creation_date             2013-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H17 N O2'
_chemical_formula_sum            'C19 H17 N O2'
_chemical_formula_weight         291.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.9806(5)
_cell_length_b                   8.6168(2)
_cell_length_c                   20.4475(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.426(3)
_cell_angle_gamma                90.00
_cell_volume                     2959.57(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4221
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6710
_cell_measurement_theta_min      5.2550
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.3400
_exptl_crystal_size_mid          0.1200
_exptl_crystal_size_min          0.0800
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8182
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         70.05
_diffrn_reflns_theta_min         5.27
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9355
_diffrn_measured_fraction_theta_max 0.9938
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   27.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -22.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000    0.0000 46

#__ type_ start__ end____ width___ exp.time_
  3 omega  -52.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
  4 omega   34.00  124.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -150.0000 90

#__ type_ start__ end____ width___ exp.time_
  5 omega   39.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -30.0000 64

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000   60.0000 93

#__ type_ start__ end____ width___ exp.time_
  7 omega   34.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  150.0000 66

#__ type_ start__ end____ width___ exp.time_
  8 omega   42.00   74.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
  9 omega   46.00   72.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   96.00  166.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   94.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  -90.0000 56

#__ type_ start__ end____ width___ exp.time_
 12 omega   52.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
 13 omega  104.00  130.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   50.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000 -150.0000 43

#__ type_ start__ end____ width___ exp.time_
 15 omega   41.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -180.0000 63

#__ type_ start__ end____ width___ exp.time_
 16 omega   90.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   61.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000    0.0000 32

#__ type_ start__ end____ width___ exp.time_
 18 omega   71.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
 19 omega  131.00  157.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   39.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000    0.0000 52

#__ type_ start__ end____ width___ exp.time_
 21 omega   82.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega  111.00  137.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   69.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega  121.00  147.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   86.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
 26 omega   71.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -120.0000 37

#__ type_ start__ end____ width___ exp.time_
 27 omega   45.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -107.0000   67.0000 68

#__ type_ start__ end____ width___ exp.time_
 28 omega  134.00  162.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
 29 omega   86.00  112.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   40.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -91.0000  -30.0000 73

#__ type_ start__ end____ width___ exp.time_
 31 omega   50.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 32 omega   97.00  147.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -80.0000   60.1860 50

#__ type_ start__ end____ width___ exp.time_
 33 omega  102.00  132.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
 34 omega   46.00   72.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -80.0000   60.1860 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0818971000
_diffrn_orient_matrix_UB_12      -0.0763350000
_diffrn_orient_matrix_UB_13      -0.0006349000
_diffrn_orient_matrix_UB_21      0.0411157000
_diffrn_orient_matrix_UB_22      0.1556192000
_diffrn_orient_matrix_UB_23      0.0203052000
_diffrn_orient_matrix_UB_31      0.0032304000
_diffrn_orient_matrix_UB_32      -0.0436939000
_diffrn_orient_matrix_UB_33      0.0734287000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2526
_reflns_number_total             2808
_reflns_odcompleteness_completeness 93.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0639
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1264P)²+0.8583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1709
_refine_ls_wR_factor_ref         0.1780
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C14(H14), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.22785(7) 0.99205(12) 0.35835(6) 0.0345(3) Uani 1 1 d . . .
O2 O 0.38926(10) 0.69511(16) 0.36929(7) 0.0536(4) Uani 1 1 d . . .
N1 N 0.36828(8) 0.73102(15) 0.47646(7) 0.0356(4) Uani 1 1 d . . .
C1 C 0.37615(9) 0.77946(19) 0.41420(8) 0.0352(4) Uani 1 1 d . . .
C2 C 0.36897(9) 0.95870(18) 0.41232(7) 0.0308(4) Uani 1 1 d . . .
C3 C 0.35056(9) 0.99373(16) 0.48102(7) 0.0281(4) Uani 1 1 d . . .
C4 C 0.33387(10) 1.13132(19) 0.51046(8) 0.0364(4) Uani 1 1 d . . .
H4 H 0.3329 1.2243 0.4872 0.044 Uiso 1 1 calc R . .
C5 C 0.31835(12) 1.1292(2) 0.57570(9) 0.0447(5) Uani 1 1 d . . .
H5 H 0.3076 1.2215 0.5963 0.054 Uiso 1 1 calc R . .
C6 C 0.31897(12) 0.9909(2) 0.60978(9) 0.0456(5) Uani 1 1 d . . .
H6 H 0.3084 0.9915 0.6532 0.055 Uiso 1 1 calc R . .
C7 C 0.33499(11) 0.8505(2) 0.58072(9) 0.0419(4) Uani 1 1 d . . .
H7 H 0.3352 0.7574 0.6037 0.050 Uiso 1 1 calc R . .
C8 C 0.35061(9) 0.85535(18) 0.51623(8) 0.0313(4) Uani 1 1 d . . .
C9 C 0.37226(12) 0.5698(2) 0.49699(10) 0.0465(5) Uani 1 1 d . . .
H9A H 0.4118 0.5583 0.5353 0.070 Uiso 1 1 calc R . .
H9B H 0.3862 0.5065 0.4618 0.070 Uiso 1 1 calc R . .
H9C H 0.3214 0.5380 0.5075 0.070 Uiso 1 1 calc R . .
C10 C 0.45145(10) 1.0261(2) 0.39861(9) 0.0367(4) Uani 1 1 d . . .
H10 H 0.4964 0.9729 0.4248 0.044 Uiso 1 1 calc R . .
C11 C 0.45628(11) 1.0190(2) 0.32387(10) 0.0444(5) Uani 1 1 d . . .
H11A H 0.5103 1.0333 0.3149 0.053 Uiso 1 1 calc R . .
H11B H 0.4352 0.9223 0.3044 0.053 Uiso 1 1 calc R . .
C12 C 0.40273(12) 1.1581(2) 0.29963(9) 0.0462(5) Uani 1 1 d . . .
H12 H 0.4091 1.1946 0.2553 0.055 Uiso 1 1 calc R . .
C13 C 0.31874(10) 1.1090(2) 0.30642(8) 0.0388(4) Uani 1 1 d . . .
C14 C 0.24160(12) 1.1439(2) 0.27173(9) 0.0446(5) Uani 1 1 d . . .
H14 H 0.2301 1.2053 0.2341 0.054 Uiso 1 1 calc R . .
C15 C 0.18857(11) 1.0705(2) 0.30421(8) 0.0415(4) Uani 1 1 d . . .
C16 C 0.30741(9) 1.01709(18) 0.35769(8) 0.0317(4) Uani 1 1 d . . .
C17 C 0.45501(10) 1.2003(2) 0.40956(10) 0.0434(4) Uani 1 1 d . . .
H17 H 0.4732 1.2478 0.4498 0.052 Uiso 1 1 calc R . .
C18 C 0.42878(12) 1.2755(2) 0.35440(11) 0.0486(5) Uani 1 1 d . . .
H18 H 0.4265 1.3828 0.3497 0.058 Uiso 1 1 calc R . .
C19 C 0.10026(12) 1.0631(3) 0.29475(11) 0.0580(6) Uani 1 1 d . . .
H19A H 0.0836 0.9566 0.2942 0.087 Uiso 1 1 calc R . .
H19B H 0.0793 1.1113 0.2535 0.087 Uiso 1 1 calc R . .
H19C H 0.0808 1.1165 0.3304 0.087 Uiso 1 1 calc R . .


_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 C15 1.382(2) . ?
O1 C16 1.3701(19) . ?
O2 C1 1.217(2) . ?
N1 C1 1.365(2) . ?
N1 C8 1.404(2) . ?
N1 C9 1.450(2) . ?
C1 C2 1.549(2) . ?
C2 C3 1.514(2) . ?
C2 C10 1.579(2) . ?
C2 C16 1.501(2) . ?
C3 C4 1.378(2) . ?
C3 C8 1.393(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.397(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.392(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.383(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9800 . ?
C10 C11 1.544(2) . ?
C10 C17 1.517(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.542(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.513(2) . ?
C12 C18 1.526(3) . ?
C13 C14 1.427(2) . ?
C13 C16 1.350(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.352(3) . ?
C15 C19 1.485(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.320(3) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C16 O1 C15 106.02(13) . . ?
C1 N1 C8 111.43(13) . . ?
C1 N1 C9 123.81(15) . . ?
C8 N1 C9 124.63(15) . . ?
O2 C1 N1 125.10(16) . . ?
O2 C1 C2 126.80(15) . . ?
N1 C1 C2 108.06(13) . . ?
C1 C2 C10 107.62(13) . . ?
C3 C2 C1 101.65(12) . . ?
C3 C2 C10 113.62(12) . . ?
C16 C2 C1 113.36(12) . . ?
C16 C2 C3 114.08(13) . . ?
C16 C2 C10 106.49(13) . . ?
C4 C3 C2 131.36(14) . . ?
C4 C3 C8 119.69(15) . . ?
C8 C3 C2 108.94(13) . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.06(15) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.31(16) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.49(17) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 121.4 . . ?
C8 C7 C6 117.24(16) . . ?
C8 C7 H7 121.4 . . ?
C3 C8 N1 109.74(14) . . ?
C7 C8 N1 128.06(15) . . ?
C7 C8 C3 122.20(15) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 H10 111.8 . . ?
C11 C10 C2 109.78(13) . . ?
C11 C10 H10 111.8 . . ?
C17 C10 C2 110.79(13) . . ?
C17 C10 H10 111.8 . . ?
C17 C10 C11 100.29(14) . . ?
C10 C11 H11A 111.8 . . ?
C10 C11 H11B 111.8 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 C10 99.97(14) . . ?
C12 C11 H11A 111.8 . . ?
C12 C11 H11B 111.8 . . ?
C11 C12 H12 114.0 . . ?
C13 C12 C11 105.82(15) . . ?
C13 C12 H12 114.0 . . ?
C13 C12 C18 107.07(15) . . ?
C18 C12 C11 100.69(16) . . ?
C18 C12 H12 114.0 . . ?
C14 C13 C12 134.76(17) . . ?
C16 C13 C12 118.61(15) . . ?
C16 C13 C14 106.53(15) . . ?
C13 C14 H14 126.7 . . ?
C15 C14 C13 106.62(15) . . ?
C15 C14 H14 126.7 . . ?
O1 C15 C19 116.29(17) . . ?
C14 C15 O1 110.14(15) . . ?
C14 C15 C19 133.53(18) . . ?
O1 C16 C2 121.35(14) . . ?
C13 C16 O1 110.68(14) . . ?
C13 C16 C2 127.71(15) . . ?
C10 C17 H17 124.5 . . ?
C18 C17 C10 110.98(17) . . ?
C18 C17 H17 124.5 . . ?
C12 C18 H18 125.5 . . ?
C17 C18 C12 109.10(17) . . ?
C17 C18 H18 125.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
O2 C1 C2 C3 178.55(17) . . . . ?
O2 C1 C2 C10 -61.8(2) . . . . ?
O2 C1 C2 C16 55.7(2) . . . . ?
N1 C1 C2 C3 -3.80(16) . . . . ?
N1 C1 C2 C10 115.85(14) . . . . ?
N1 C1 C2 C16 -126.67(14) . . . . ?
C1 N1 C8 C3 -3.17(18) . . . . ?
C1 N1 C8 C7 176.82(16) . . . . ?
C1 C2 C3 C4 -176.83(16) . . . . ?
C1 C2 C3 C8 1.95(15) . . . . ?
C1 C2 C10 C11 81.49(16) . . . . ?
C1 C2 C10 C17 -168.66(14) . . . . ?
C1 C2 C16 O1 68.34(18) . . . . ?
C1 C2 C16 C13 -118.10(18) . . . . ?
C2 C3 C4 C5 179.58(16) . . . . ?
C2 C3 C8 N1 0.48(17) . . . . ?
C2 C3 C8 C7 -179.51(14) . . . . ?
C2 C10 C11 C12 76.77(17) . . . . ?
C2 C10 C17 C18 -90.54(18) . . . . ?
C3 C2 C10 C11 -166.79(13) . . . . ?
C3 C2 C10 C17 -56.94(18) . . . . ?
C3 C2 C16 O1 -47.37(19) . . . . ?
C3 C2 C16 C13 126.18(18) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C3 C8 N1 179.43(14) . . . . ?
C4 C3 C8 C7 -0.6(2) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 N1 179.99(16) . . . . ?
C6 C7 C8 C3 0.0(2) . . . . ?
C8 N1 C1 O2 -177.89(16) . . . . ?
C8 N1 C1 C2 4.40(17) . . . . ?
C8 C3 C4 C5 0.9(2) . . . . ?
C9 N1 C1 O2 -1.9(3) . . . . ?
C9 N1 C1 C2 -179.60(15) . . . . ?
C9 N1 C8 C3 -179.14(15) . . . . ?
C9 N1 C8 C7 0.9(3) . . . . ?
C10 C2 C3 C4 67.9(2) . . . . ?
C10 C2 C3 C8 -113.35(14) . . . . ?
C10 C2 C16 O1 -173.52(13) . . . . ?
C10 C2 C16 C13 0.0(2) . . . . ?
C10 C11 C12 C13 -70.62(17) . . . . ?
C10 C11 C12 C18 40.73(16) . . . . ?
C10 C17 C18 C12 1.1(2) . . . . ?
C11 C10 C17 C18 25.36(19) . . . . ?
C11 C12 C13 C14 -149.2(2) . . . . ?
C11 C12 C13 C16 35.0(2) . . . . ?
C11 C12 C18 C17 -27.19(19) . . . . ?
C12 C13 C14 C15 -176.3(2) . . . . ?
C12 C13 C16 O1 176.36(14) . . . . ?
C12 C13 C16 C2 2.2(3) . . . . ?
C13 C12 C18 C17 83.19(19) . . . . ?
C13 C14 C15 O1 0.8(2) . . . . ?
C13 C14 C15 C19 178.2(2) . . . . ?
C14 C13 C16 O1 -0.5(2) . . . . ?
C14 C13 C16 C2 -174.65(15) . . . . ?
C15 O1 C16 C2 175.54(14) . . . . ?
C15 O1 C16 C13 0.99(18) . . . . ?
C16 O1 C15 C14 -1.08(19) . . . . ?
C16 O1 C15 C19 -178.98(16) . . . . ?
C16 C2 C3 C4 -54.5(2) . . . . ?
C16 C2 C3 C8 124.33(14) . . . . ?
C16 C2 C10 C11 -40.36(17) . . . . ?
C16 C2 C10 C17 69.48(16) . . . . ?
C16 C13 C14 C15 -0.1(2) . . . . ?
C17 C10 C11 C12 -39.89(16) . . . . ?
C18 C12 C13 C14 104.0(2) . . . . ?
C18 C12 C13 C16 -71.8(2) . . . . ?

