# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_cu_5771g
_database_code_depnum_ccdc_archive 'CCDC 1915249'
loop_
_audit_author_name
_audit_author_address
'Gregor Schnakenburg'
;University of Bonn
Germany
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-08-19 downloaded from the CCDC.
;
_audit_creation_date             2018-11-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_chemical_name_common            ?
_chemical_name_systematic        JK-494
_chemical_formula_moiety         'C19 H23 N3 O'
_chemical_formula_sum            'C19 H23 N3 O'
_chemical_formula_weight         309.40
_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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'

_cell_length_a                   6.1589(2)
_cell_length_b                   10.7744(3)
_cell_length_c                   13.0636(4)
_cell_angle_alpha                104.0900(10)
_cell_angle_beta                 93.6580(10)
_cell_angle_gamma                95.6470(10)
_cell_volume                     833.25(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.48
_cell_measurement_theta_min      3.50
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5754
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1617 before and 0.0866 after correction.
The Ratio of minimum to maximum transmission is 0.7635.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            33750
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         67.50
_diffrn_reflns_theta_min         3.50
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'Bruker Photon100 detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                5492
_reflns_number_total             5817
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXH-1997 (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.0120(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5817
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0498P)²+0.1455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0936
_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, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6), C2'(H2'), C6'(H6')
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,
 H10B), C11(H11A,H11B), C4'(H4'A,H4'B), C5'(H5'A,H5'B), C7'(H7'A,H7'B),
 C8'(H8'A,H8'B), C9'(H9'A,H9'B), C10'(H10C,H10D), C11'(H11C,H11D)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), N1'(H1'),
 C13'(H13'), C15'(H15'), C16'(H16'), C17'(H17'), C18'(H18'), C19'(H19')
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O O 0.3321(2) 0.40209(13) 0.55861(11) 0.0309(3) Uani 1 d . . .
N1 N 0.6755(3) 0.49600(15) 0.61788(12) 0.0260(4) Uani 1 d . . .
H1 H 0.6639 0.5427 0.5716 0.031 Uiso 1 calc . . R
N2 N 0.7066(2) 0.35036(14) 0.76244(12) 0.0214(3) Uani 1 d . . .
N3 N 1.0522(2) 0.42372(14) 0.82170(12) 0.0224(3) Uani 1 d . . .
C1 C 0.4992(3) 0.41556(17) 0.62051(15) 0.0241(4) Uani 1 d . . .
C2 C 0.8864(3) 0.51741(16) 0.68152(14) 0.0218(4) Uani 1 d . . .
H2 H 1.0017 0.4928 0.6323 0.026 Uiso 1 calc . . R
C3 C 0.8847(3) 0.43282(17) 0.75672(14) 0.0213(4) Uani 1 d . . .
C4 C 0.4955(3) 0.33765(18) 0.70175(16) 0.0256(4) Uani 1 d . . .
H4A H 0.3839 0.3659 0.7510 0.031 Uiso 1 calc . . R
H4B H 0.4518 0.2458 0.6655 0.031 Uiso 1 calc . . R
C5 C 0.9450(3) 0.65992(16) 0.74011(14) 0.0250(4) Uani 1 d . . .
H5A H 0.8223 0.6882 0.7820 0.030 Uiso 1 calc . . R
H5B H 1.0754 0.6676 0.7906 0.030 Uiso 1 calc . . R
C6 C 0.9925(3) 0.75162(17) 0.66943(15) 0.0263(4) Uani 1 d . . .
H6 H 0.8728 0.7329 0.6105 0.032 Uiso 1 calc . . R
C7 C 1.2110(4) 0.7352(2) 0.6213(2) 0.0446(6) Uani 1 d . . .
H7A H 1.2053 0.6466 0.5758 0.054 Uiso 1 calc . . R
H7B H 1.3295 0.7470 0.6789 0.054 Uiso 1 calc . . R
C8 C 1.2635(6) 0.8320(2) 0.5553(2) 0.0661(9) Uani 1 d . . .
H8A H 1.4092 0.8213 0.5286 0.079 Uiso 1 calc . . R
H8B H 1.1535 0.8145 0.4933 0.079 Uiso 1 calc . . R
C9 C 1.2629(5) 0.9695(2) 0.6204(2) 0.0538(7) Uani 1 d . . .
H9A H 1.3836 0.9901 0.6779 0.065 Uiso 1 calc . . R
H9B H 1.2886 1.0296 0.5747 0.065 Uiso 1 calc . . R
C10 C 1.0484(5) 0.9878(2) 0.66777(19) 0.0455(6) Uani 1 d . . .
H10A H 0.9300 0.9768 0.6103 0.055 Uiso 1 calc . . R
H10B H 1.0560 1.0765 0.7133 0.055 Uiso 1 calc . . R
C11 C 0.9947(4) 0.89128(18) 0.73365(16) 0.0332(5) Uani 1 d . . .
H11A H 0.8495 0.9031 0.7605 0.040 Uiso 1 calc . . R
H11B H 1.1048 0.9087 0.7956 0.040 Uiso 1 calc . . R
C12 C 0.9780(3) 0.32872(17) 0.87044(14) 0.0215(4) Uani 1 d . . .
C13 C 0.7641(3) 0.28306(17) 0.83487(14) 0.0227(4) Uani 1 d . . .
H13 H 0.6744 0.2184 0.8559 0.027 Uiso 1 calc . . R
C14 C 1.1275(3) 0.28598(17) 0.94382(14) 0.0218(4) Uani 1 d . . .
C15 C 1.3128(3) 0.36817(18) 0.99559(15) 0.0253(4) Uani 1 d . . .
H15 H 1.3335 0.4540 0.9881 0.030 Uiso 1 calc . . R
C16 C 1.4667(3) 0.3266(2) 1.05762(15) 0.0279(4) Uani 1 d . . .
H16 H 1.5930 0.3832 1.0912 0.033 Uiso 1 calc . . R
C17 C 1.4363(4) 0.20226(19) 1.07067(15) 0.0299(4) Uani 1 d . . .
H17 H 1.5420 0.1729 1.1126 0.036 Uiso 1 calc . . R
C18 C 1.2497(4) 0.12111(19) 1.02187(16) 0.0334(5) Uani 1 d . . .
H18 H 1.2264 0.0365 1.0318 0.040 Uiso 1 calc . . R
C19 C 1.0978(3) 0.16226(18) 0.95918(16) 0.0289(4) Uani 1 d . . .
H19 H 0.9713 0.1054 0.9261 0.035 Uiso 1 calc . . R
O' O 0.6290(2) 0.61686(13) 0.44616(10) 0.0290(3) Uani 1 d . . .
N1' N 0.3150(3) 0.49410(14) 0.36566(12) 0.0239(3) Uani 1 d . . .
H1' H 0.2980 0.4646 0.4222 0.029 Uiso 1 calc . . R
N2' N 0.2918(3) 0.63666(15) 0.21993(12) 0.0227(3) Uani 1 d . . .
N3' N -0.0472(2) 0.55508(14) 0.15601(12) 0.0220(3) Uani 1 d . . .
C1' C 0.4848(3) 0.58406(17) 0.37116(15) 0.0239(4) Uani 1 d . . .
C2' C 0.1543(3) 0.44026(16) 0.27300(14) 0.0217(4) Uani 1 d . . .
H2' H 0.2140 0.3671 0.2247 0.026 Uiso 1 calc . . R
C3' C 0.1263(3) 0.54283(16) 0.21534(14) 0.0214(4) Uani 1 d . . .
C4' C 0.5030(3) 0.64773(19) 0.28084(16) 0.0257(4) Uani 1 d . . .
H4'A H 0.5587 0.7399 0.3093 0.031 Uiso 1 calc . . R
H4'B H 0.6094 0.6071 0.2335 0.031 Uiso 1 calc . . R
C5' C -0.0636(3) 0.38978(18) 0.30572(15) 0.0241(4) Uani 1 d . . .
H5'A H -0.1688 0.3613 0.2417 0.029 Uiso 1 calc . . R
H5'B H -0.1206 0.4623 0.3545 0.029 Uiso 1 calc . . R
C6' C -0.0598(3) 0.27842(17) 0.35959(14) 0.0226(4) Uani 1 d . . .
H6' H 0.0285 0.3116 0.4296 0.027 Uiso 1 calc . . R
C7' C 0.0420(4) 0.16372(19) 0.29685(17) 0.0342(5) Uani 1 d . . .
H7'A H 0.1963 0.1913 0.2880 0.041 Uiso 1 calc . . R
H7'B H -0.0378 0.1322 0.2255 0.041 Uiso 1 calc . . R
C8' C 0.0339(4) 0.0540(2) 0.3528(2) 0.0446(6) Uani 1 d . . .
H8'A H 0.0930 -0.0208 0.3080 0.054 Uiso 1 calc . . R
H8'B H 0.1277 0.0825 0.4206 0.054 Uiso 1 calc . . R
C9' C -0.1987(5) 0.0130(2) 0.3747(2) 0.0460(6) Uani 1 d . . .
H9'A H -0.2886 -0.0257 0.3067 0.055 Uiso 1 calc . . R
H9'B H -0.1963 -0.0532 0.4156 0.055 Uiso 1 calc . . R
C10' C -0.3009(4) 0.1268(2) 0.43644(18) 0.0417(6) Uani 1 d . . .
H10C H -0.2215 0.1588 0.5079 0.050 Uiso 1 calc . . R
H10D H -0.4551 0.0990 0.4452 0.050 Uiso 1 calc . . R
C11' C -0.2930(3) 0.2349(2) 0.38033(17) 0.0324(5) Uani 1 d . . .
H11C H -0.3551 0.3092 0.4242 0.039 Uiso 1 calc . . R
H11D H -0.3849 0.2053 0.3120 0.039 Uiso 1 calc . . R
C12' C 0.0103(3) 0.66441(17) 0.12088(15) 0.0232(4) Uani 1 d . . .
C13' C 0.2207(3) 0.71564(17) 0.15988(15) 0.0239(4) Uani 1 d . . .
H13' H 0.3004 0.7901 0.1479 0.029 Uiso 1 calc . . R
C14' C -0.1488(3) 0.71292(18) 0.05633(15) 0.0236(4) Uani 1 d . . .
C15' C -0.3120(3) 0.62846(18) -0.01193(15) 0.0254(4) Uani 1 d . . .
H15' H -0.3147 0.5383 -0.0196 0.031 Uiso 1 calc . . R
C16' C -0.4698(3) 0.67369(19) -0.06865(16) 0.0292(4) Uani 1 d . . .
H16' H -0.5807 0.6148 -0.1142 0.035 Uiso 1 calc . . R
C17' C -0.4668(3) 0.8053(2) -0.05916(16) 0.0325(5) Uani 1 d . . .
H17' H -0.5766 0.8367 -0.0972 0.039 Uiso 1 calc . . R
C18' C -0.3028(4) 0.88982(19) 0.00604(18) 0.0362(5) Uani 1 d . . .
H18' H -0.2975 0.9796 0.0112 0.043 Uiso 1 calc . . R
C19' C -0.1457(4) 0.84480(19) 0.06412(17) 0.0317(4) Uani 1 d . . .
H19' H -0.0351 0.9041 0.1096 0.038 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
O C1 1.241(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.329(2) . ?
N1 C2 1.463(2) . ?
N2 C3 1.360(2) . ?
N2 C4 1.455(2) . ?
N2 C13 1.374(2) . ?
N3 C3 1.320(2) . ?
N3 C12 1.387(2) . ?
C1 C4 1.505(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.494(2) . ?
C2 C5 1.535(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.528(2) . ?
C6 H6 1.0000 . ?
C6 C7 1.529(3) . ?
C6 C11 1.532(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.531(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.519(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.504(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.529(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.370(3) . ?
C12 C14 1.471(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.398(3) . ?
C14 C19 1.392(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.379(3) . ?
C19 H19 0.9500 . ?
O' C1' 1.238(2) . ?
N1' H1' 0.8800 . ?
N1' C1' 1.340(2) . ?
N1' C2' 1.474(2) . ?
N2' C3' 1.351(2) . ?
N2' C4' 1.459(2) . ?
N2' C13' 1.373(2) . ?
N3' C3' 1.316(2) . ?
N3' C12' 1.388(2) . ?
C1' C4' 1.507(3) . ?
C2' H2' 1.0000 . ?
C2' C3' 1.498(2) . ?
C2' C5' 1.524(3) . ?
C4' H4'A 0.9900 . ?
C4' H4'B 0.9900 . ?
C5' H5'A 0.9900 . ?
C5' H5'B 0.9900 . ?
C5' C6' 1.533(2) . ?
C6' H6' 1.0000 . ?
C6' C7' 1.522(3) . ?
C6' C11' 1.528(3) . ?
C7' H7'A 0.9900 . ?
C7' H7'B 0.9900 . ?
C7' C8' 1.533(3) . ?
C8' H8'A 0.9900 . ?
C8' H8'B 0.9900 . ?
C8' C9' 1.523(3) . ?
C9' H9'A 0.9900 . ?
C9' H9'B 0.9900 . ?
C9' C10' 1.512(4) . ?
C10' H10C 0.9900 . ?
C10' H10D 0.9900 . ?
C10' C11' 1.519(3) . ?
C11' H11C 0.9900 . ?
C11' H11D 0.9900 . ?
C12' C13' 1.372(3) . ?
C12' C14' 1.468(3) . ?
C13' H13' 0.9500 . ?
C14' C15' 1.394(3) . ?
C14' C19' 1.398(3) . ?
C15' H15' 0.9500 . ?
C15' C16' 1.381(3) . ?
C16' H16' 0.9500 . ?
C16' C17' 1.391(3) . ?
C17' H17' 0.9500 . ?
C17' C18' 1.381(3) . ?
C18' H18' 0.9500 . ?
C18' C19' 1.387(3) . ?
C19' H19' 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
C1 N1 H1 115.6 . . ?
C1 N1 C2 128.80(15) . . ?
C2 N1 H1 115.6 . . ?
C3 N2 C4 125.23(15) . . ?
C3 N2 C13 107.48(15) . . ?
C13 N2 C4 127.29(15) . . ?
C3 N3 C12 105.17(15) . . ?
O C1 N1 122.61(17) . . ?
O C1 C4 117.33(17) . . ?
N1 C1 C4 120.06(17) . . ?
N1 C2 H2 107.9 . . ?
N1 C2 C3 110.29(15) . . ?
N1 C2 C5 111.36(14) . . ?
C3 C2 H2 107.9 . . ?
C3 C2 C5 111.40(14) . . ?
C5 C2 H2 107.9 . . ?
N2 C3 C2 122.57(16) . . ?
N3 C3 N2 111.62(15) . . ?
N3 C3 C2 125.77(16) . . ?
N2 C4 C1 112.68(15) . . ?
N2 C4 H4A 109.1 . . ?
N2 C4 H4B 109.1 . . ?
C1 C4 H4A 109.1 . . ?
C1 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C2 C5 H5A 108.4 . . ?
C2 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C6 C5 C2 115.35(15) . . ?
C6 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
C5 C6 H6 108.5 . . ?
C5 C6 C7 112.03(16) . . ?
C5 C6 C11 109.80(15) . . ?
C7 C6 H6 108.5 . . ?
C7 C6 C11 109.40(17) . . ?
C11 C6 H6 108.5 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C6 C7 C8 111.8(2) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 C7 111.2(2) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.1(2) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C9 C10 C11 111.33(19) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C6 C11 H11A 109.2 . . ?
C6 C11 H11B 109.2 . . ?
C10 C11 C6 112.16(17) . . ?
C10 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N3 C12 C14 120.47(16) . . ?
C13 C12 N3 110.15(16) . . ?
C13 C12 C14 129.29(17) . . ?
N2 C13 H13 127.2 . . ?
C12 C13 N2 105.58(16) . . ?
C12 C13 H13 127.2 . . ?
C15 C14 C12 119.80(16) . . ?
C19 C14 C12 121.95(17) . . ?
C19 C14 C15 118.15(17) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.08(18) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 119.99(19) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.31(18) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.61(18) . . ?
C19 C18 H18 119.7 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.83(19) . . ?
C18 C19 H19 119.6 . . ?
C1' N1' H1' 117.2 . . ?
C1' N1' C2' 125.57(15) . . ?
C2' N1' H1' 117.2 . . ?
C3' N2' C4' 123.85(15) . . ?
C3' N2' C13' 107.52(15) . . ?
C13' N2' C4' 128.63(15) . . ?
C3' N3' C12' 105.09(15) . . ?
O' C1' N1' 123.43(17) . . ?
O' C1' C4' 118.18(17) . . ?
N1' C1' C4' 118.39(16) . . ?
N1' C2' H2' 108.5 . . ?
N1' C2' C3' 108.41(14) . . ?
N1' C2' C5' 111.42(15) . . ?
C3' C2' H2' 108.5 . . ?
C3' C2' C5' 111.31(15) . . ?
C5' C2' H2' 108.5 . . ?
N2' C3' C2' 120.33(16) . . ?
N3' C3' N2' 112.00(15) . . ?
N3' C3' C2' 127.68(16) . . ?
N2' C4' C1' 111.54(16) . . ?
N2' C4' H4'A 109.3 . . ?
N2' C4' H4'B 109.3 . . ?
C1' C4' H4'A 109.3 . . ?
C1' C4' H4'B 109.3 . . ?
H4'A C4' H4'B 108.0 . . ?
C2' C5' H5'A 108.2 . . ?
C2' C5' H5'B 108.2 . . ?
C2' C5' C6' 116.51(15) . . ?
H5'A C5' H5'B 107.3 . . ?
C6' C5' H5'A 108.2 . . ?
C6' C5' H5'B 108.2 . . ?
C5' C6' H6' 107.9 . . ?
C7' C6' C5' 113.83(15) . . ?
C7' C6' H6' 107.9 . . ?
C7' C6' C11' 109.79(15) . . ?
C11' C6' C5' 109.30(15) . . ?
C11' C6' H6' 107.9 . . ?
C6' C7' H7'A 109.4 . . ?
C6' C7' H7'B 109.4 . . ?
C6' C7' C8' 111.34(17) . . ?
H7'A C7' H7'B 108.0 . . ?
C8' C7' H7'A 109.4 . . ?
C8' C7' H7'B 109.4 . . ?
C7' C8' H8'A 109.3 . . ?
C7' C8' H8'B 109.3 . . ?
H8'A C8' H8'B 107.9 . . ?
C9' C8' C7' 111.72(19) . . ?
C9' C8' H8'A 109.3 . . ?
C9' C8' H8'B 109.3 . . ?
C8' C9' H9'A 109.5 . . ?
C8' C9' H9'B 109.5 . . ?
H9'A C9' H9'B 108.0 . . ?
C10' C9' C8' 110.90(18) . . ?
C10' C9' H9'A 109.5 . . ?
C10' C9' H9'B 109.5 . . ?
C9' C10' H10C 109.4 . . ?
C9' C10' H10D 109.4 . . ?
C9' C10' C11' 111.26(19) . . ?
H10C C10' H10D 108.0 . . ?
C11' C10' H10C 109.4 . . ?
C11' C10' H10D 109.4 . . ?
C6' C11' H11C 109.2 . . ?
C6' C11' H11D 109.2 . . ?
C10' C11' C6' 112.16(17) . . ?
C10' C11' H11C 109.2 . . ?
C10' C11' H11D 109.2 . . ?
H11C C11' H11D 107.9 . . ?
N3' C12' C14' 120.78(16) . . ?
C13' C12' N3' 109.89(16) . . ?
C13' C12' C14' 129.26(17) . . ?
N2' C13' H13' 127.2 . . ?
C12' C13' N2' 105.50(16) . . ?
C12' C13' H13' 127.2 . . ?
C15' C14' C12' 120.60(16) . . ?
C15' C14' C19' 118.23(17) . . ?
C19' C14' C12' 121.13(17) . . ?
C14' C15' H15' 119.5 . . ?
C16' C15' C14' 121.08(17) . . ?
C16' C15' H15' 119.5 . . ?
C15' C16' H16' 119.9 . . ?
C15' C16' C17' 120.16(19) . . ?
C17' C16' H16' 119.9 . . ?
C16' C17' H17' 120.3 . . ?
C18' C17' C16' 119.40(18) . . ?
C18' C17' H17' 120.3 . . ?
C17' C18' H18' 119.7 . . ?
C17' C18' C19' 120.55(18) . . ?
C19' C18' H18' 119.7 . . ?
C14' C19' H19' 119.7 . . ?
C18' C19' C14' 120.55(19) . . ?
C18' C19' H19' 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'

