# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_xray_0301_2
_database_code_depnum_ccdc_archive 'CCDC 1569863'
_audit_update_record             
;
2017-08-21 deposited with the CCDC.
2018-04-23 downloaded from the CCDC.
;
_audit_creation_date             2017-03-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H22 N2 O6'
_chemical_formula_sum            'C23 H22 N2 O6'
_chemical_formula_weight         422.42
_chemical_absolute_configuration ?
_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 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.6235(6)
_cell_length_b                   13.3554(9)
_cell_length_c                   16.7938(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2158.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1136
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.6150
_cell_measurement_theta_min      3.9050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77856
_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_absorpt_special_details   ?
_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    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5512
_diffrn_reflns_point_group_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.283
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -18.00   20.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000   90.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega  -32.00   12.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -38.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
  3 omega   -9.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000   60.0000 72
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0019870000
_diffrn_orient_matrix_UB_12      -0.0472716000
_diffrn_orient_matrix_UB_13      -0.0192079000
_diffrn_orient_matrix_UB_21      0.0018250000
_diffrn_orient_matrix_UB_22      -0.0241796000
_diffrn_orient_matrix_UB_23      0.0375984000
_diffrn_orient_matrix_UB_31      -0.0736508000
_diffrn_orient_matrix_UB_32      -0.0018846000
_diffrn_orient_matrix_UB_33      0.0004039000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.587
_reflns_Friedel_fraction_full    0.799
_reflns_Friedel_fraction_max     0.773
_reflns_number_gt                2228
_reflns_number_total             3828
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(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         0.170
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 561 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.8(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3828
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0646
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²+0.2773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1635
_refine_special_details          ?
_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:
 C16(H16), C17(H17), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1945(5) -0.3646(4) -0.2298(3) 0.116(2) Uani 1 1 d . . . . .
O2 O 0.2142(5) -0.2103(4) -0.2079(3) 0.1039(17) Uani 1 1 d . . . . .
O3 O -0.3262(4) -0.0952(4) -0.0438(3) 0.0883(14) Uani 1 1 d . . . . .
O4 O -0.1273(4) -0.0141(3) -0.0605(3) 0.0773(12) Uani 1 1 d . . . . .
O5 O -0.0792(4) -0.1881(6) 0.0860(2) 0.132(3) Uani 1 1 d . . . . .
O6 O 0.1080(4) -0.1638(3) 0.0144(2) 0.0711(11) Uani 1 1 d . . . . .
N1 N -0.2781(5) -0.3937(4) -0.3110(3) 0.0718(14) Uani 1 1 d . . . . .
N2 N 0.1599(5) -0.2902(5) -0.1957(3) 0.0657(13) Uani 1 1 d . . . . .
C1 C -0.1999(7) -0.4463(5) -0.2560(3) 0.0712(17) Uani 1 1 d . . . . .
H1 H -0.1954 -0.5157 -0.2530 0.085 Uiso 1 1 calc R . . . .
C2 C -0.1311(6) -0.3828(4) -0.2073(3) 0.0602(15) Uani 1 1 d . . . . .
C3 C -0.1671(5) -0.2851(4) -0.2333(3) 0.0514(13) Uani 1 1 d . . . . .
C4 C -0.1252(5) -0.1935(4) -0.2026(3) 0.0526(13) Uani 1 1 d . . . . .
C5 C -0.1729(6) -0.1082(4) -0.2396(3) 0.0638(15) Uani 1 1 d . . . . .
H5 H -0.1451 -0.0455 -0.2216 0.077 Uiso 1 1 calc R . . . .
C6 C -0.2642(7) -0.1165(5) -0.3048(3) 0.0774(19) Uani 1 1 d . . . . .
H6 H -0.2958 -0.0582 -0.3291 0.093 Uiso 1 1 calc R . . . .
C7 C -0.3087(7) -0.2077(6) -0.3341(3) 0.0735(17) Uani 1 1 d . . . . .
H7 H -0.3703 -0.2115 -0.3767 0.088 Uiso 1 1 calc R . . . .
C8 C -0.2580(6) -0.2931(5) -0.2978(3) 0.0603(14) Uani 1 1 d . . . . .
C9 C -0.3682(7) -0.4358(6) -0.3717(4) 0.089(2) Uani 1 1 d . . . . .
H9A H -0.4622 -0.4117 -0.3633 0.107 Uiso 1 1 calc R . . . .
H9B H -0.3693 -0.5081 -0.3664 0.107 Uiso 1 1 calc R . . . .
C10 C -0.3228(6) -0.4088(5) -0.4549(3) 0.0658(16) Uani 1 1 d . . . . .
C11 C -0.1899(8) -0.4256(6) -0.4782(4) 0.100(2) Uani 1 1 d . . . . .
H11 H -0.1274 -0.4543 -0.4427 0.120 Uiso 1 1 calc R . . . .
C12 C -0.1475(11) -0.4014(7) -0.5520(5) 0.130(3) Uani 1 1 d . . . . .
H12 H -0.0557 -0.4141 -0.5660 0.156 Uiso 1 1 calc R . . . .
C13 C -0.2293(13) -0.3609(7) -0.6046(5) 0.119(3) Uani 1 1 d . . . . .
H13 H -0.1945 -0.3442 -0.6545 0.143 Uiso 1 1 calc R . . . .
C14 C -0.3648(11) -0.3427(6) -0.5874(5) 0.106(3) Uani 1 1 d . . . . .
H14 H -0.4244 -0.3159 -0.6255 0.127 Uiso 1 1 calc R . . . .
C15 C -0.4128(8) -0.3658(6) -0.5100(5) 0.108(3) Uani 1 1 d . . . . .
H15 H -0.5044 -0.3522 -0.4959 0.130 Uiso 1 1 calc R . . . .
C16 C -0.0306(5) -0.1980(4) -0.1296(3) 0.0477(12) Uani 1 1 d . . . . .
H16 H 0.0359 -0.1426 -0.1328 0.057 Uiso 1 1 calc R . . . .
C17 C 0.0506(5) -0.2963(4) -0.1298(3) 0.0543(13) Uani 1 1 d . . . . .
H17 H 0.1003 -0.3007 -0.0790 0.065 Uiso 1 1 calc R . . . .
C18 C -0.0338(6) -0.3930(4) -0.1392(3) 0.0642(15) Uani 1 1 d . . . . .
H18A H 0.0285 -0.4489 -0.1484 0.077 Uiso 1 1 calc R . . . .
H18B H -0.0856 -0.4060 -0.0908 0.077 Uiso 1 1 calc R . . . .
C19 C -0.1118(5) -0.1883(4) -0.0510(3) 0.0533(14) Uani 1 1 d . . . . .
H19 H -0.1699 -0.2478 -0.0437 0.064 Uiso 1 1 calc R . . . .
C20 C -0.2039(6) -0.0958(5) -0.0513(3) 0.0591(14) Uani 1 1 d . . . . .
C21 C -0.2016(8) 0.0815(5) -0.0626(5) 0.111(3) Uani 1 1 d . . . . .
H21A H -0.2637 0.0854 -0.0179 0.167 Uiso 1 1 calc GR . . . .
H21B H -0.2540 0.0861 -0.1111 0.167 Uiso 1 1 calc GR . . . .
H21C H -0.1360 0.1355 -0.0601 0.167 Uiso 1 1 calc GR . . . .
C22 C -0.0135(6) -0.1788(5) 0.0188(3) 0.0619(16) Uani 1 1 d . . . . .
C23 C 0.0079(7) -0.1837(11) 0.1576(4) 0.182(6) Uani 1 1 d . . . . .
H23A H -0.0498 -0.1731 0.2035 0.273 Uiso 1 1 calc GR . . . .
H23B H 0.0729 -0.1295 0.1528 0.273 Uiso 1 1 calc GR . . . .
H23C H 0.0576 -0.2456 0.1635 0.273 Uiso 1 1 calc GR . . . .


_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 N2 1.194(6) . ?
O2 N2 1.205(6) . ?
O3 C20 1.184(6) . ?
O4 C20 1.326(6) . ?
O4 C21 1.463(7) . ?
O5 C22 1.300(6) . ?
O5 C23 1.467(6) . ?
O6 C22 1.189(6) . ?
N1 C1 1.383(7) . ?
N1 C8 1.376(7) . ?
N1 C9 1.451(7) . ?
N2 C17 1.529(7) . ?
C1 H1 0.9300 . ?
C1 C2 1.351(7) . ?
C2 C3 1.419(7) . ?
C2 C18 1.484(7) . ?
C3 C4 1.387(7) . ?
C3 C8 1.396(7) . ?
C4 C5 1.376(7) . ?
C4 C16 1.529(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.408(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.508(8) . ?
C10 C11 1.356(9) . ?
C10 C15 1.391(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.343(9) . ?
C12 H12 0.9300 . ?
C12 C13 1.302(11) . ?
C13 H13 0.9300 . ?
C13 C14 1.358(12) . ?
C14 H14 0.9300 . ?
C14 C15 1.414(11) . ?
C15 H15 0.9300 . ?
C16 H16 0.9800 . ?
C16 C17 1.528(7) . ?
C16 C19 1.539(7) . ?
C17 H17 0.9800 . ?
C17 C18 1.533(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19 0.9800 . ?
C19 C20 1.520(7) . ?
C19 C22 1.513(7) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C20 O4 C21 116.7(5) . . ?
C22 O5 C23 115.5(4) . . ?
C1 N1 C9 126.7(6) . . ?
C8 N1 C1 108.1(5) . . ?
C8 N1 C9 125.1(5) . . ?
O1 N2 O2 122.3(5) . . ?
O1 N2 C17 119.6(6) . . ?
O2 N2 C17 118.0(5) . . ?
N1 C1 H1 124.7 . . ?
C2 C1 N1 110.7(5) . . ?
C2 C1 H1 124.7 . . ?
C1 C2 C3 105.7(5) . . ?
C1 C2 C18 136.0(6) . . ?
C3 C2 C18 118.3(5) . . ?
C4 C3 C2 128.8(5) . . ?
C4 C3 C8 122.5(5) . . ?
C8 C3 C2 108.7(5) . . ?
C3 C4 C16 115.9(4) . . ?
C5 C4 C3 117.8(5) . . ?
C5 C4 C16 126.4(5) . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.6(6) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 118.7 . . ?
C7 C6 C5 122.6(6) . . ?
C7 C6 H6 118.7 . . ?
C6 C7 H7 121.3 . . ?
C8 C7 C6 117.4(5) . . ?
C8 C7 H7 121.3 . . ?
N1 C8 C3 106.8(5) . . ?
N1 C8 C7 133.2(6) . . ?
C7 C8 C3 120.0(6) . . ?
N1 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
N1 C9 C10 112.6(5) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C11 C10 C9 120.1(6) . . ?
C11 C10 C15 117.7(6) . . ?
C15 C10 C9 122.3(7) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.8(8) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 118.6 . . ?
C13 C12 C11 122.8(9) . . ?
C13 C12 H12 118.6 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.7(9) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 121.0 . . ?
C13 C14 C15 118.1(8) . . ?
C15 C14 H14 121.0 . . ?
C10 C15 C14 119.8(8) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C4 C16 H16 108.3 . . ?
C4 C16 C19 112.5(4) . . ?
C17 C16 C4 109.6(4) . . ?
C17 C16 H16 108.3 . . ?
C17 C16 C19 109.6(4) . . ?
C19 C16 H16 108.3 . . ?
N2 C17 H17 107.3 . . ?
N2 C17 C18 109.6(5) . . ?
C16 C17 N2 107.9(4) . . ?
C16 C17 H17 107.3 . . ?
C16 C17 C18 116.9(4) . . ?
C18 C17 H17 107.3 . . ?
C2 C18 C17 109.7(5) . . ?
C2 C18 H18A 109.7 . . ?
C2 C18 H18B 109.7 . . ?
C17 C18 H18A 109.7 . . ?
C17 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C16 C19 H19 109.1 . . ?
C20 C19 C16 111.2(4) . . ?
C20 C19 H19 109.1 . . ?
C22 C19 C16 110.7(4) . . ?
C22 C19 H19 109.1 . . ?
C22 C19 C20 107.4(4) . . ?
O3 C20 O4 124.0(6) . . ?
O3 C20 C19 125.8(6) . . ?
O4 C20 C19 110.2(4) . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O5 C22 C19 111.1(4) . . ?
O6 C22 O5 123.3(5) . . ?
O6 C22 C19 125.5(5) . . ?
O5 C23 H23A 109.5 . . ?
O5 C23 H23B 109.5 . . ?
O5 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O1 N2 C17 C16 -148.7(5) . . . . ?
O1 N2 C17 C18 -20.4(7) . . . . ?
O2 N2 C17 C16 35.7(6) . . . . ?
O2 N2 C17 C18 164.0(5) . . . . ?
N1 C1 C2 C3 -0.3(7) . . . . ?
N1 C1 C2 C18 -179.7(6) . . . . ?
N1 C9 C10 C11 52.2(9) . . . . ?
N1 C9 C10 C15 -127.4(7) . . . . ?
N2 C17 C18 C2 -74.2(5) . . . . ?
C1 N1 C8 C3 -0.5(6) . . . . ?
C1 N1 C8 C7 179.8(6) . . . . ?
C1 N1 C9 C10 -118.5(7) . . . . ?
C1 C2 C3 C4 179.4(5) . . . . ?
C1 C2 C3 C8 0.0(6) . . . . ?
C1 C2 C18 C17 158.2(7) . . . . ?
C2 C3 C4 C5 178.8(5) . . . . ?
C2 C3 C4 C16 -1.9(7) . . . . ?
C2 C3 C8 N1 0.3(6) . . . . ?
C2 C3 C8 C7 -180.0(5) . . . . ?
C3 C2 C18 C17 -21.1(7) . . . . ?
C3 C4 C5 C6 1.7(8) . . . . ?
C3 C4 C16 C17 26.8(6) . . . . ?
C3 C4 C16 C19 -95.4(5) . . . . ?
C4 C3 C8 N1 -179.1(5) . . . . ?
C4 C3 C8 C7 0.6(8) . . . . ?
C4 C5 C6 C7 -0.2(9) . . . . ?
C4 C16 C17 N2 72.0(5) . . . . ?
C4 C16 C17 C18 -52.0(5) . . . . ?
C4 C16 C19 C20 -52.9(6) . . . . ?
C4 C16 C19 C22 -172.2(5) . . . . ?
C5 C4 C16 C17 -154.0(5) . . . . ?
C5 C4 C16 C19 83.8(6) . . . . ?
C5 C6 C7 C8 -1.2(9) . . . . ?
C6 C7 C8 N1 -179.4(6) . . . . ?
C6 C7 C8 C3 0.9(8) . . . . ?
C8 N1 C1 C2 0.5(7) . . . . ?
C8 N1 C9 C10 62.7(8) . . . . ?
C8 C3 C4 C5 -2.0(7) . . . . ?
C8 C3 C4 C16 177.3(4) . . . . ?
C9 N1 C1 C2 -178.4(5) . . . . ?
C9 N1 C8 C3 178.5(5) . . . . ?
C9 N1 C8 C7 -1.2(10) . . . . ?
C9 C10 C11 C12 -179.5(8) . . . . ?
C9 C10 C15 C14 -179.5(7) . . . . ?
C10 C11 C12 C13 0.1(15) . . . . ?
C11 C10 C15 C14 0.9(11) . . . . ?
C11 C12 C13 C14 -1.3(17) . . . . ?
C12 C13 C14 C15 2.2(15) . . . . ?
C13 C14 C15 C10 -2.0(13) . . . . ?
C15 C10 C11 C12 0.0(12) . . . . ?
C16 C4 C5 C6 -177.5(5) . . . . ?
C16 C17 C18 C2 49.0(6) . . . . ?
C16 C19 C20 O3 120.6(6) . . . . ?
C16 C19 C20 O4 -60.0(5) . . . . ?
C16 C19 C22 O5 -168.8(5) . . . . ?
C16 C19 C22 O6 11.9(9) . . . . ?
C17 C16 C19 C20 -175.1(4) . . . . ?
C17 C16 C19 C22 65.6(6) . . . . ?
C18 C2 C3 C4 -1.2(8) . . . . ?
C18 C2 C3 C8 179.5(4) . . . . ?
C19 C16 C17 N2 -164.1(4) . . . . ?
C19 C16 C17 C18 71.9(5) . . . . ?
C20 C19 C22 O5 69.6(7) . . . . ?
C20 C19 C22 O6 -109.7(7) . . . . ?
C21 O4 C20 O3 -1.1(9) . . . . ?
C21 O4 C20 C19 179.6(5) . . . . ?
C22 C19 C20 O3 -118.1(6) . . . . ?
C22 C19 C20 O4 61.3(6) . . . . ?
C23 O5 C22 O6 -2.8(11) . . . . ?
C23 O5 C22 C19 177.9(8) . . . . ?

_olex2_date_sample_data_collection 2017-03-01
_olex2_submission_special_instructions 'No special instructions were received'
