# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_luoych_0720
_database_code_depnum_ccdc_archive 'CCDC 1857538'
_audit_update_record             
;
2018-07-23 deposited with the CCDC.
2018-08-21 downloaded from the CCDC.
;
_audit_creation_date             2018-07-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H19 N O5'
_chemical_formula_sum            'C20 H19 N O5'
_chemical_formula_weight         353.36
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   8.2648(2)
_cell_length_b                   10.1169(2)
_cell_length_c                   10.9096(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.079(3)
_cell_angle_gamma                90.00
_cell_volume                     876.51(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2809
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      69.7450
_cell_measurement_theta_min      4.3640
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76697
_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_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3576
_diffrn_reflns_theta_full        66.54
_diffrn_reflns_theta_max         66.54
_diffrn_reflns_theta_min         5.57
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -85.00  -42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000   30.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega  -26.00    1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -74.00  -47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega  -86.00  -43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  150.0000 43

#__ type_ start__ end____ width___ exp.time_
  5 omega   32.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  120.0000 86

#__ type_ start__ end____ width___ exp.time_
  6 omega   48.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   79.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 42

#__ type_ start__ end____ width___ exp.time_
  8 omega   42.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   60.0000 54

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 44

#__ type_ start__ end____ width___ exp.time_
 10 omega   55.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
 11 omega   37.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 75

#__ type_ start__ end____ width___ exp.time_
 13 omega   65.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   40.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 44

#__ type_ start__ end____ width___ exp.time_
 15 omega   49.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 42

#__ type_ start__ end____ width___ exp.time_
 16 omega   61.00  156.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000  -60.0000 95

#__ type_ start__ end____ width___ exp.time_
 17 omega  121.00  162.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   60.0000 41

#__ type_ start__ end____ width___ exp.time_
 18 omega  -79.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -50.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
 19 omega  -81.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -38.0000  -90.0000 100

#__ type_ start__ end____ width___ exp.time_
 20 omega  -79.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -50.0000 -171.0000 94

#__ type_ start__ end____ width___ exp.time_
 21 omega   23.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -30.0000 89

#__ type_ start__ end____ width___ exp.time_
 22 omega  -20.00    5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -19.0000   60.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0417994000
_diffrn_orient_matrix_UB_12      0.0138205000
_diffrn_orient_matrix_UB_13      -0.1460823000
_diffrn_orient_matrix_UB_21      -0.1473548000
_diffrn_orient_matrix_UB_22      0.0927412000
_diffrn_orient_matrix_UB_23      0.0008219000
_diffrn_orient_matrix_UB_31      0.1191062000
_diffrn_orient_matrix_UB_32      0.1199508000
_diffrn_orient_matrix_UB_33      0.0162781000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2242
_reflns_number_total             2269
_reflns_odcompleteness_completeness 97.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(18)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2269
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.067
_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)+(0.0486P)²+0.0687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0747
_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:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.44989(15) 0.12263(14) 0.53766(11) 0.0292(3) Uani 1 d . . .
O2 O 0.10047(19) -0.29261(14) 0.25914(17) 0.0430(4) Uani 1 d . . .
O3 O 0.29903(16) -0.14880(13) 0.24652(12) 0.0294(3) Uani 1 d . . .
O4 O -0.14192(15) 0.00212(13) 0.39305(13) 0.0318(3) Uani 1 d . . .
O5 O -0.15320(17) -0.08832(16) 0.20406(13) 0.0429(4) Uani 1 d . . .
N1 N 0.33247(16) 0.03759(15) 0.49543(13) 0.0210(3) Uani 1 d . . .
C1 C 0.21204(19) 0.04230(17) 0.38749(15) 0.0195(3) Uani 1 d . . .
C2 C 0.1127(2) -0.08517(16) 0.36825(15) 0.0200(3) Uani 1 d . . .
C3 C 0.1553(2) -0.14097(19) 0.50580(16) 0.0255(4) Uani 1 d . . .
H3A H 0.0732 -0.1120 0.5487 0.031 Uiso 1 calc . . R
H3B H 0.1575 -0.2368 0.5050 0.031 Uiso 1 calc . . R
C4 C 0.3294(2) -0.08532(17) 0.57182(15) 0.0220(3) Uani 1 d . . .
H4 H 0.4169 -0.1469 0.5627 0.026 Uiso 1 calc . . R
C5 C 0.17809(19) 0.15795(18) 0.30485(16) 0.0218(3) Uani 1 d . . .
C6 C 0.1128(2) 0.1455(2) 0.17275(18) 0.0305(4) Uani 1 d . . .
H6 H 0.0984 0.0622 0.1352 0.037 Uiso 1 calc . . R
C7 C 0.0695(3) 0.2581(2) 0.0975(2) 0.0390(5) Uani 1 d . . .
H7 H 0.0272 0.2498 0.0095 0.047 Uiso 1 calc . . R
C8 C 0.0890(3) 0.3819(2) 0.1526(2) 0.0420(5) Uani 1 d . . .
H8 H 0.0593 0.4568 0.1020 0.050 Uiso 1 calc . . R
C9 C 0.1529(3) 0.3945(2) 0.2836(2) 0.0400(5) Uani 1 d . . .
H9 H 0.1649 0.4778 0.3210 0.048 Uiso 1 calc . . R
C10 C 0.1984(2) 0.28405(19) 0.35810(19) 0.0290(4) Uani 1 d . . .
H10 H 0.2437 0.2936 0.4457 0.035 Uiso 1 calc . . R
C11 C 0.1674(2) -0.18730(16) 0.28379(17) 0.0233(4) Uani 1 d . . .
C12 C 0.3677(3) -0.2485(2) 0.1779(2) 0.0367(5) Uani 1 d . . .
H12A H 0.2876 -0.2665 0.0973 0.055 Uiso 1 calc . . GR
H12B H 0.3902 -0.3282 0.2275 0.055 Uiso 1 calc . . GR
H12C H 0.4703 -0.2162 0.1638 0.055 Uiso 1 calc . . GR
C13 C -0.0763(2) -0.05949(17) 0.31001(16) 0.0238(4) Uani 1 d . . .
C14 C -0.3199(2) 0.0339(3) 0.3457(3) 0.0506(6) Uani 1 d . . .
H14A H -0.3368 0.0939 0.2752 0.076 Uiso 1 calc . . GR
H14B H -0.3575 0.0744 0.4126 0.076 Uiso 1 calc . . GR
H14C H -0.3829 -0.0456 0.3182 0.076 Uiso 1 calc . . GR
C15 C 0.3562(2) -0.05049(18) 0.71041(15) 0.0232(4) Uani 1 d . . .
C16 C 0.4808(2) -0.1129(2) 0.80444(17) 0.0283(4) Uani 1 d . . .
H16 H 0.5462 -0.1787 0.7824 0.034 Uiso 1 calc . . R
C17 C 0.5079(3) -0.0772(2) 0.93150(18) 0.0371(5) Uani 1 d . . .
H17 H 0.5914 -0.1190 0.9945 0.045 Uiso 1 calc . . R
C18 C 0.4109(2) 0.0204(2) 0.96416(17) 0.0378(5) Uani 1 d . . .
H18 H 0.4302 0.0449 1.0491 0.045 Uiso 1 calc . . R
C19 C 0.2853(2) 0.0817(2) 0.87136(18) 0.0325(4) Uani 1 d . . .
H19 H 0.2192 0.1466 0.8940 0.039 Uiso 1 calc . . R
C20 C 0.2580(2) 0.0466(2) 0.74480(17) 0.0278(4) Uani 1 d . . .
H20 H 0.1735 0.0881 0.6823 0.033 Uiso 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 N1 1.2832(18) . ?
O2 C11 1.196(2) . ?
O3 C11 1.321(2) . ?
O3 C12 1.461(2) . ?
O4 C13 1.333(2) . ?
O4 C14 1.454(2) . ?
O5 C13 1.191(2) . ?
N1 C1 1.316(2) . ?
N1 C4 1.501(2) . ?
C1 C2 1.512(2) . ?
C1 C5 1.456(2) . ?
C2 C3 1.550(2) . ?
C2 C11 1.533(2) . ?
C2 C13 1.537(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.527(2) . ?
C4 H4 0.9800 . ?
C4 C15 1.508(2) . ?
C5 C6 1.398(2) . ?
C5 C10 1.393(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.391(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.379(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.385(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.371(3) . ?
C10 H10 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.388(2) . ?
C15 C20 1.390(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.390(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(3) . ?
C20 H20 0.9300 . ?

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
C11 O3 C12 115.08(15) . . ?
C13 O4 C14 115.11(15) . . ?
O1 N1 C1 127.34(15) . . ?
O1 N1 C4 118.91(13) . . ?
C1 N1 C4 113.72(14) . . ?
N1 C1 C2 109.90(14) . . ?
N1 C1 C5 123.48(16) . . ?
C5 C1 C2 126.54(14) . . ?
C1 C2 C3 101.97(13) . . ?
C1 C2 C11 114.80(13) . . ?
C1 C2 C13 111.33(13) . . ?
C11 C2 C3 108.11(14) . . ?
C11 C2 C13 107.48(13) . . ?
C13 C2 C3 113.20(13) . . ?
C2 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C4 C3 C2 104.71(13) . . ?
C4 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
N1 C4 C3 101.66(13) . . ?
N1 C4 H4 110.1 . . ?
N1 C4 C15 110.04(14) . . ?
C3 C4 H4 110.1 . . ?
C15 C4 C3 114.61(13) . . ?
C15 C4 H4 110.1 . . ?
C6 C5 C1 121.28(16) . . ?
C10 C5 C1 119.84(15) . . ?
C10 C5 C6 118.70(17) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.82(19) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.41(19) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.88(19) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C5 C10 H10 119.4 . . ?
C9 C10 C5 121.16(18) . . ?
C9 C10 H10 119.4 . . ?
O2 C11 O3 124.21(17) . . ?
O2 C11 C2 122.72(16) . . ?
O3 C11 C2 113.01(14) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C13 C2 110.89(14) . . ?
O5 C13 O4 124.48(16) . . ?
O5 C13 C2 124.61(15) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C4 120.48(16) . . ?
C16 C15 C20 119.43(16) . . ?
C20 C15 C4 120.08(15) . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.00(19) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 119.99(18) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.35(18) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.89(18) . . ?
C20 C19 H19 120.1 . . ?
C15 C20 H20 119.8 . . ?
C19 C20 C15 120.34(17) . . ?
C19 C20 H20 119.8 . . ?

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
O1 N1 C1 C2 173.57(14) . . . . ?
O1 N1 C1 C5 -9.4(2) . . . . ?
O1 N1 C4 C3 168.11(14) . . . . ?
O1 N1 C4 C15 46.25(18) . . . . ?
N1 C1 C2 C3 20.22(16) . . . . ?
N1 C1 C2 C11 -96.39(16) . . . . ?
N1 C1 C2 C13 141.22(14) . . . . ?
N1 C1 C5 C6 149.42(16) . . . . ?
N1 C1 C5 C10 -35.5(2) . . . . ?
N1 C4 C15 C16 -127.27(17) . . . . ?
N1 C4 C15 C20 51.5(2) . . . . ?
C1 N1 C4 C3 -13.86(17) . . . . ?
C1 N1 C4 C15 -135.72(14) . . . . ?
C1 C2 C3 C4 -27.80(16) . . . . ?
C1 C2 C11 O2 -179.60(18) . . . . ?
C1 C2 C11 O3 3.1(2) . . . . ?
C1 C2 C13 O4 -68.74(17) . . . . ?
C1 C2 C13 O5 109.9(2) . . . . ?
C1 C5 C6 C7 175.00(16) . . . . ?
C1 C5 C10 C9 -173.98(17) . . . . ?
C2 C1 C5 C6 -34.1(2) . . . . ?
C2 C1 C5 C10 140.97(16) . . . . ?
C2 C3 C4 N1 25.30(16) . . . . ?
C2 C3 C4 C15 143.94(15) . . . . ?
C3 C2 C11 O2 67.4(2) . . . . ?
C3 C2 C11 O3 -109.94(15) . . . . ?
C3 C2 C13 O4 45.44(19) . . . . ?
C3 C2 C13 O5 -135.96(19) . . . . ?
C3 C4 C15 C16 118.93(18) . . . . ?
C3 C4 C15 C20 -62.3(2) . . . . ?
C4 N1 C1 C2 -4.27(18) . . . . ?
C4 N1 C1 C5 172.76(14) . . . . ?
C4 C15 C16 C17 177.99(17) . . . . ?
C4 C15 C20 C19 -178.06(16) . . . . ?
C5 C1 C2 C3 -156.69(15) . . . . ?
C5 C1 C2 C11 86.70(19) . . . . ?
C5 C1 C2 C13 -35.7(2) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C6 C5 C10 C9 1.2(2) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C9 C10 C5 -1.5(3) . . . . ?
C10 C5 C6 C7 -0.1(2) . . . . ?
C11 C2 C3 C4 93.56(16) . . . . ?
C11 C2 C13 O4 164.75(14) . . . . ?
C11 C2 C13 O5 -16.7(2) . . . . ?
C12 O3 C11 O2 -3.8(3) . . . . ?
C12 O3 C11 C2 173.42(15) . . . . ?
C13 C2 C3 C4 -147.50(15) . . . . ?
C13 C2 C11 O2 -55.2(2) . . . . ?
C13 C2 C11 O3 127.54(15) . . . . ?
C14 O4 C13 O5 -0.1(3) . . . . ?
C14 O4 C13 C2 178.53(18) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C15 C20 C19 0.7(3) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C17 C18 C19 C20 -0.9(3) . . . . ?
C18 C19 C20 C15 0.1(3) . . . . ?
C20 C15 C16 C17 -0.8(3) . . . . ?

_olex2_date_sample_data_collection 2018-07-23
_olex2_submission_special_instructions 'No special instructions were received'
