# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_khc1233-2h
_database_code_depnum_ccdc_archive 'CCDC 1540349'
_audit_update_record             
;
2017-03-25 deposited with the CCDC.
2017-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H31 N3 O3'
_chemical_formula_sum            'C25 H31 N3 O3'
_chemical_formula_weight         421.53

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7851(18)
_cell_length_b                   10.557(2)
_cell_length_c                   13.269(3)
_cell_angle_alpha                100.21(3)
_cell_angle_beta                 97.69(3)
_cell_angle_gamma                111.07(3)
_cell_volume                     1103.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3882
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      25.00

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8210
_diffrn_reflns_av_R_equivalents  0.1825
_diffrn_reflns_av_sigmaI/netI    0.2831
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3882
_reflns_number_gt                1236
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0331P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.0073(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3882
_refine_ls_number_parameters     286
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2494
_refine_ls_R_factor_gt           0.0818
_refine_ls_wR_factor_ref         0.1729
_refine_ls_wR_factor_gt          0.1272
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_restrained_S_all      0.814
_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
O2 O 0.4731(5) 0.8121(4) 0.0719(3) 0.0452(11) Uani 1 1 d . . .
O1 O 0.8846(5) 1.1920(4) 0.0812(3) 0.0486(12) Uani 1 1 d . . .
O3 O 0.4345(5) 0.6380(4) 0.1555(4) 0.0564(13) Uani 1 1 d . . .
N1 N 0.8294(6) 0.9896(5) -0.1213(4) 0.0372(13) Uani 1 1 d . . .
N2 N 0.7419(6) 0.9913(5) 0.1310(4) 0.0386(13) Uani 1 1 d . . .
N3 N 0.2327(7) 0.7169(6) 0.1162(5) 0.0536(16) Uani 1 1 d D . .
C1 C 0.7139(9) 0.5292(7) -0.4616(5) 0.072(2) Uani 1 1 d . . .
H1A H 0.6669 0.5437 -0.5260 0.108 Uiso 1 1 calc R . .
H1B H 0.6407 0.4424 -0.4507 0.108 Uiso 1 1 calc R . .
H1C H 0.8208 0.5258 -0.4654 0.108 Uiso 1 1 calc R . .
C2 C 0.7350(8) 0.6482(7) -0.3715(5) 0.0513(19) Uani 1 1 d . . .
C3 C 0.6896(8) 0.6241(6) -0.2798(5) 0.0451(17) Uani 1 1 d . . .
H3 H 0.6405 0.5322 -0.2743 0.054 Uiso 1 1 calc R . .
C4 C 0.7151(8) 0.7355(7) -0.1922(5) 0.0435(17) Uani 1 1 d . . .
C5 C 0.7938(7) 0.8743(7) -0.2010(5) 0.0404(16) Uani 1 1 d . . .
C6 C 0.8317(8) 0.8969(7) -0.2982(5) 0.0498(18) Uani 1 1 d . . .
H6 H 0.8764 0.9876 -0.3067 0.060 Uiso 1 1 calc R . .
C7 C 0.8029(9) 0.7864(8) -0.3793(5) 0.059(2) Uani 1 1 d . . .
H7 H 0.8297 0.8039 -0.4423 0.071 Uiso 1 1 calc R . .
C8 C 0.6635(7) 0.7119(6) -0.0978(5) 0.0413(17) Uani 1 1 d . . .
H8 H 0.6106 0.6221 -0.0890 0.050 Uiso 1 1 calc R . .
C9 C 0.6960(7) 0.8280(6) -0.0209(5) 0.0394(16) Uani 1 1 d . . .
C10 C 0.7825(7) 0.9600(6) -0.0355(5) 0.0333(15) Uani 1 1 d . . .
C11 C 0.8114(8) 1.0660(7) 0.0638(5) 0.0422(16) Uani 1 1 d . . .
C12 C 0.6491(7) 0.8423(6) 0.0866(5) 0.0381(16) Uani 1 1 d . . .
H12 H 0.6829 0.7850 0.1281 0.046 Uiso 1 1 calc R . .
C13 C 0.3818(8) 0.7138(6) 0.1193(5) 0.0391(16) Uani 1 1 d . . .
C14 C 0.1003(8) 0.6252(6) 0.1566(5) 0.0417(16) Uani 1 1 d . . .
H14 H 0.0993 0.5307 0.1392 0.050 Uiso 1 1 calc R . .
C15 C 0.1284(9) 0.6731(7) 0.2753(5) 0.059(2) Uani 1 1 d . . .
H15A H 0.2317 0.6698 0.3086 0.071 Uiso 1 1 calc R . .
H15B H 0.1368 0.7688 0.2948 0.071 Uiso 1 1 calc R . .
C16 C -0.0172(10) 0.5772(8) 0.3109(6) 0.076(2) Uani 1 1 d . . .
H16A H -0.0186 0.4835 0.2948 0.091 Uiso 1 1 calc R . .
H16B H 0.0009 0.6077 0.3865 0.091 Uiso 1 1 calc R . .
C17 C -0.1821(10) 0.5710(8) 0.2636(6) 0.073(2) Uani 1 1 d . . .
H17A H -0.1870 0.6621 0.2838 0.087 Uiso 1 1 calc R . .
H17B H -0.2690 0.5044 0.2879 0.087 Uiso 1 1 calc R . .
C18 C -0.2081(9) 0.5266(7) 0.1464(6) 0.068(2) Uani 1 1 d . . .
H18A H -0.3122 0.5296 0.1142 0.081 Uiso 1 1 calc R . .
H18B H -0.2176 0.4306 0.1267 0.081 Uiso 1 1 calc R . .
C19 C -0.0653(8) 0.6200(7) 0.1048(5) 0.0532(19) Uani 1 1 d . . .
H19A H -0.0842 0.5842 0.0297 0.064 Uiso 1 1 calc R . .
H19B H -0.0635 0.7139 0.1175 0.064 Uiso 1 1 calc R . .
C20 C 0.7449(7) 1.0633(6) 0.2392(5) 0.0390(16) Uani 1 1 d . . .
H20 H 0.8548 1.1404 0.2653 0.047 Uiso 1 1 calc R . .
C21 C 0.7269(9) 0.9702(7) 0.3125(5) 0.0569(19) Uani 1 1 d . . .
H21A H 0.8124 0.9323 0.3121 0.068 Uiso 1 1 calc R . .
H21B H 0.6187 0.8926 0.2895 0.068 Uiso 1 1 calc R . .
C22 C 0.7431(9) 1.0525(7) 0.4257(5) 0.067(2) Uani 1 1 d . . .
H22A H 0.7261 0.9897 0.4722 0.080 Uiso 1 1 calc R . .
H22B H 0.8544 1.1255 0.4511 0.080 Uiso 1 1 calc R . .
C23 C 0.6151(9) 1.1170(7) 0.4262(5) 0.062(2) Uani 1 1 d . . .
H23A H 0.5038 1.0434 0.4061 0.075 Uiso 1 1 calc R . .
H23B H 0.6285 1.1708 0.4965 0.075 Uiso 1 1 calc R . .
C24 C 0.6335(9) 1.2100(7) 0.3524(5) 0.057(2) Uani 1 1 d . . .
H24A H 0.7422 1.2870 0.3749 0.069 Uiso 1 1 calc R . .
H24B H 0.5488 1.2488 0.3531 0.069 Uiso 1 1 calc R . .
C25 C 0.6155(8) 1.1271(6) 0.2398(4) 0.0468(18) Uani 1 1 d . . .
H25A H 0.5043 1.0537 0.2155 0.056 Uiso 1 1 calc R . .
H25B H 0.6308 1.1892 0.1928 0.056 Uiso 1 1 calc R . .
H3A H 0.220(8) 0.772(6) 0.078(4) 0.07(2) Uiso 1 1 d 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
O2 C13 1.373(7) . ?
O2 C12 1.439(6) . ?
O1 C11 1.213(6) . ?
O3 C13 1.195(6) . ?
N1 C10 1.313(7) . ?
N1 C5 1.371(7) . ?
N2 C11 1.356(7) . ?
N2 C12 1.452(6) . ?
N2 C20 1.492(7) . ?
N3 C13 1.318(7) . ?
N3 C14 1.455(7) . ?
N3 H3A 0.86(2) . ?
C1 C2 1.512(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.368(8) . ?
C2 C7 1.392(9) . ?
C3 C4 1.428(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.411(8) . ?
C4 C8 1.421(8) . ?
C5 C6 1.413(8) . ?
C6 C7 1.361(8) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.361(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(8) . ?
C9 C12 1.534(7) . ?
C10 C11 1.495(8) . ?
C12 H12 0.9800 . ?
C14 C19 1.500(8) . ?
C14 C15 1.523(8) . ?
C14 H14 0.9800 . ?
C15 C16 1.512(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.474(10) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.502(9) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.530(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.484(8) . ?
C20 C25 1.517(7) . ?
C20 H20 0.9800 . ?
C21 C22 1.557(8) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.510(8) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.489(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.548(7) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?

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
C13 O2 C12 116.7(5) . . ?
C10 N1 C5 114.1(5) . . ?
C11 N2 C12 115.6(5) . . ?
C11 N2 C20 120.7(5) . . ?
C12 N2 C20 123.2(5) . . ?
C13 N3 C14 125.2(6) . . ?
C13 N3 H3A 110(5) . . ?
C14 N3 H3A 124(5) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 118.0(6) . . ?
C3 C2 C1 121.3(6) . . ?
C7 C2 C1 120.7(6) . . ?
C2 C3 C4 122.1(6) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C8 119.2(5) . . ?
C5 C4 C3 118.1(6) . . ?
C8 C4 C3 122.7(6) . . ?
N1 C5 C4 123.4(5) . . ?
N1 C5 C6 117.7(6) . . ?
C4 C5 C6 118.8(6) . . ?
C7 C6 C5 120.3(6) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 122.5(6) . . ?
C6 C7 H7 118.7 . . ?
C2 C7 H7 118.7 . . ?
C9 C8 C4 116.2(5) . . ?
C9 C8 H8 121.9 . . ?
C4 C8 H8 121.9 . . ?
C8 C9 C10 120.0(5) . . ?
C8 C9 C12 130.4(5) . . ?
C10 C9 C12 109.6(5) . . ?
N1 C10 C9 126.9(5) . . ?
N1 C10 C11 124.8(5) . . ?
C9 C10 C11 108.3(5) . . ?
O1 C11 N2 127.3(6) . . ?
O1 C11 C10 127.3(6) . . ?
N2 C11 C10 105.4(5) . . ?
O2 C12 N2 108.9(4) . . ?
O2 C12 C9 109.0(5) . . ?
N2 C12 C9 100.2(4) . . ?
O2 C12 H12 112.7 . . ?
N2 C12 H12 112.7 . . ?
C9 C12 H12 112.7 . . ?
O3 C13 N3 127.4(6) . . ?
O3 C13 O2 123.0(6) . . ?
N3 C13 O2 109.6(5) . . ?
N3 C14 C19 109.6(5) . . ?
N3 C14 C15 111.5(6) . . ?
C19 C14 C15 110.3(5) . . ?
N3 C14 H14 108.4 . . ?
C19 C14 H14 108.4 . . ?
C15 C14 H14 108.4 . . ?
C16 C15 C14 108.6(6) . . ?
C16 C15 H15A 110.0 . . ?
C14 C15 H15A 110.0 . . ?
C16 C15 H15B 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
C17 C16 C15 115.0(6) . . ?
C17 C16 H16A 108.5 . . ?
C15 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C15 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C16 C17 C18 108.4(6) . . ?
C16 C17 H17A 110.0 . . ?
C18 C17 H17A 110.0 . . ?
C16 C17 H17B 110.0 . . ?
C18 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
C17 C18 C19 112.3(6) . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
C14 C19 C18 111.4(6) . . ?
C14 C19 H19A 109.4 . . ?
C18 C19 H19A 109.4 . . ?
C14 C19 H19B 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C21 C20 N2 112.4(5) . . ?
C21 C20 C25 110.9(5) . . ?
N2 C20 C25 111.9(5) . . ?
C21 C20 H20 107.1 . . ?
N2 C20 H20 107.1 . . ?
C25 C20 H20 107.1 . . ?
C20 C21 C22 110.5(5) . . ?
C20 C21 H21A 109.5 . . ?
C22 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C23 C22 C21 109.9(6) . . ?
C23 C22 H22A 109.7 . . ?
C21 C22 H22A 109.7 . . ?
C23 C22 H22B 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C24 C23 C22 111.0(6) . . ?
C24 C23 H23A 109.4 . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23B 109.4 . . ?
C22 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C23 C24 C25 110.4(5) . . ?
C23 C24 H24A 109.6 . . ?
C25 C24 H24A 109.6 . . ?
C23 C24 H24B 109.6 . . ?
C25 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
C20 C25 C24 109.7(5) . . ?
C20 C25 H25A 109.7 . . ?
C24 C25 H25A 109.7 . . ?
C20 C25 H25B 109.7 . . ?
C24 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?

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
C7 C2 C3 C4 -2.2(9) . . . . ?
C1 C2 C3 C4 177.3(6) . . . . ?
C2 C3 C4 C5 -1.7(9) . . . . ?
C2 C3 C4 C8 177.9(6) . . . . ?
C10 N1 C5 C4 -0.6(8) . . . . ?
C10 N1 C5 C6 176.5(5) . . . . ?
C8 C4 C5 N1 2.5(9) . . . . ?
C3 C4 C5 N1 -178.0(6) . . . . ?
C8 C4 C5 C6 -174.6(6) . . . . ?
C3 C4 C5 C6 4.9(8) . . . . ?
N1 C5 C6 C7 178.3(6) . . . . ?
C4 C5 C6 C7 -4.4(9) . . . . ?
C5 C6 C7 C2 0.5(10) . . . . ?
C3 C2 C7 C6 2.8(10) . . . . ?
C1 C2 C7 C6 -176.6(6) . . . . ?
C5 C4 C8 C9 -0.5(8) . . . . ?
C3 C4 C8 C9 -180.0(6) . . . . ?
C4 C8 C9 C10 -3.1(9) . . . . ?
C4 C8 C9 C12 175.7(6) . . . . ?
C5 N1 C10 C9 -3.4(8) . . . . ?
C5 N1 C10 C11 177.9(6) . . . . ?
C8 C9 C10 N1 5.5(9) . . . . ?
C12 C9 C10 N1 -173.5(5) . . . . ?
C8 C9 C10 C11 -175.7(6) . . . . ?
C12 C9 C10 C11 5.4(7) . . . . ?
C12 N2 C11 O1 174.8(6) . . . . ?
C20 N2 C11 O1 2.0(9) . . . . ?
C12 N2 C11 C10 -6.5(7) . . . . ?
C20 N2 C11 C10 -179.3(5) . . . . ?
N1 C10 C11 O1 -2.1(10) . . . . ?
C9 C10 C11 O1 179.0(6) . . . . ?
N1 C10 C11 N2 179.2(5) . . . . ?
C9 C10 C11 N2 0.3(6) . . . . ?
C13 O2 C12 N2 -123.9(5) . . . . ?
C13 O2 C12 C9 127.7(5) . . . . ?
C11 N2 C12 O2 -105.0(5) . . . . ?
C20 N2 C12 O2 67.6(6) . . . . ?
C11 N2 C12 C9 9.2(6) . . . . ?
C20 N2 C12 C9 -178.2(5) . . . . ?
C8 C9 C12 O2 -73.1(8) . . . . ?
C10 C9 C12 O2 105.7(5) . . . . ?
C8 C9 C12 N2 172.7(6) . . . . ?
C10 C9 C12 N2 -8.5(6) . . . . ?
C14 N3 C13 O3 -0.6(11) . . . . ?
C14 N3 C13 O2 178.5(6) . . . . ?
C12 O2 C13 O3 -12.9(9) . . . . ?
C12 O2 C13 N3 168.0(5) . . . . ?
C13 N3 C14 C19 -158.4(6) . . . . ?
C13 N3 C14 C15 79.1(8) . . . . ?
N3 C14 C15 C16 177.5(5) . . . . ?
C19 C14 C15 C16 55.5(7) . . . . ?
C14 C15 C16 C17 -58.3(8) . . . . ?
C15 C16 C17 C18 57.1(9) . . . . ?
C16 C17 C18 C19 -54.1(8) . . . . ?
N3 C14 C19 C18 -179.0(5) . . . . ?
C15 C14 C19 C18 -55.8(7) . . . . ?
C17 C18 C19 C14 55.8(7) . . . . ?
C11 N2 C20 C21 -157.3(5) . . . . ?
C12 N2 C20 C21 30.5(7) . . . . ?
C11 N2 C20 C25 77.2(7) . . . . ?
C12 N2 C20 C25 -95.1(6) . . . . ?
N2 C20 C21 C22 176.1(5) . . . . ?
C25 C20 C21 C22 -57.8(7) . . . . ?
C20 C21 C22 C23 56.8(8) . . . . ?
C21 C22 C23 C24 -57.1(8) . . . . ?
C22 C23 C24 C25 58.2(8) . . . . ?
C21 C20 C25 C24 58.1(7) . . . . ?
N2 C20 C25 C24 -175.6(5) . . . . ?
C23 C24 C25 C20 -57.8(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_khd392h
_database_code_depnum_ccdc_archive 'CCDC 1540401'
_audit_update_record             
;
2017-03-26 deposited with the CCDC.
2017-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 N2 O2'
_chemical_formula_sum            'C21 H20 N2 O2'
_chemical_formula_weight         332.39

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   15.937(3)
_cell_length_b                   8.9523(18)
_cell_length_c                   12.934(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.46(3)
_cell_angle_gamma                90.00
_cell_volume                     1705.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3006
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      24.99

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8780
_diffrn_reflns_av_R_equivalents  0.0877
_diffrn_reflns_av_sigmaI/netI    0.0818
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3006
_reflns_number_gt                1788
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0560P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.0124(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3006
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_gt          0.1072
_refine_ls_goodness_of_fit_ref   0.858
_refine_ls_restrained_S_all      0.858
_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
O1 O -0.00459(10) 1.0305(2) 0.27980(13) 0.0673(5) Uani 1 1 d . . .
O2 O -0.12892(10) 0.66070(17) 0.04018(14) 0.0566(4) Uani 1 1 d . . .
N1 N 0.13987(11) 0.9049(2) 0.20838(13) 0.0467(5) Uani 1 1 d . . .
N2 N -0.09933(11) 0.90050(19) 0.12681(13) 0.0461(5) Uani 1 1 d . . .
C1 C 0.32952(15) 0.9297(3) 0.30765(18) 0.0648(7) Uani 1 1 d . . .
H1 H 0.2942 0.9844 0.3371 0.078 Uiso 1 1 calc R . .
C2 C 0.42229(18) 0.9364(4) 0.3573(2) 0.0859(9) Uani 1 1 d . . .
H2 H 0.4495 0.9970 0.4196 0.103 Uiso 1 1 calc R . .
C3 C 0.47615(18) 0.8542(4) 0.3158(2) 0.0875(9) Uani 1 1 d . . .
H3 H 0.5390 0.8575 0.3515 0.105 Uiso 1 1 calc R . .
C4 C 0.43711(17) 0.7689(3) 0.2231(2) 0.0742(7) Uani 1 1 d . . .
H4 H 0.4737 0.7145 0.1954 0.089 Uiso 1 1 calc R . .
C5 C 0.34242(15) 0.7615(3) 0.16840(18) 0.0564(6) Uani 1 1 d . . .
C6 C 0.28801(14) 0.8412(3) 0.21344(16) 0.0493(5) Uani 1 1 d . . .
C7 C 0.18993(13) 0.8317(2) 0.15967(15) 0.0441(5) Uani 1 1 d . . .
C8 C 0.15113(15) 0.7453(2) 0.06115(16) 0.0488(5) Uani 1 1 d . . .
C9 C 0.20880(16) 0.6734(3) 0.01509(19) 0.0618(6) Uani 1 1 d . . .
H9 H 0.1833 0.6219 -0.0522 0.074 Uiso 1 1 calc R . .
C10 C 0.30017(17) 0.6793(3) 0.0680(2) 0.0649(7) Uani 1 1 d . . .
H10 H 0.3362 0.6281 0.0378 0.078 Uiso 1 1 calc R . .
C11 C 0.05553(15) 0.7329(2) 0.01193(16) 0.0512(6) Uani 1 1 d . . .
H11 H 0.0273 0.6775 -0.0530 0.061 Uiso 1 1 calc R . .
C12 C 0.00647(14) 0.8041(2) 0.06219(15) 0.0445(5) Uani 1 1 d . . .
C13 C 0.05114(14) 0.8883(2) 0.15786(15) 0.0435(5) Uani 1 1 d . . .
C14 C -0.01710(14) 0.9513(2) 0.19830(16) 0.0466(5) Uani 1 1 d . . .
C15 C -0.09394(13) 0.8036(2) 0.03847(15) 0.0469(5) Uani 1 1 d . . .
H15 H -0.1269 0.8499 -0.0345 0.056 Uiso 1 1 calc R . .
C16 C -0.18377(14) 0.9337(3) 0.14293(17) 0.0508(6) Uani 1 1 d . . .
H16 H -0.1781 1.0350 0.1736 0.061 Uiso 1 1 calc R . .
C17 C -0.19780(16) 0.8296(3) 0.22674(18) 0.0693(7) Uani 1 1 d . . .
H17A H -0.1464 0.8370 0.2975 0.083 Uiso 1 1 calc R . .
H17B H -0.2010 0.7275 0.2003 0.083 Uiso 1 1 calc R . .
C18 C -0.28419(18) 0.8667(4) 0.2445(2) 0.0870(9) Uani 1 1 d . . .
H18A H -0.2941 0.7919 0.2929 0.104 Uiso 1 1 calc R . .
H18B H -0.2769 0.9625 0.2820 0.104 Uiso 1 1 calc R . .
C19 C -0.36618(17) 0.8730(4) 0.1366(2) 0.0806(8) Uani 1 1 d . . .
H19A H -0.3799 0.7734 0.1051 0.097 Uiso 1 1 calc R . .
H19B H -0.4180 0.9080 0.1516 0.097 Uiso 1 1 calc R . .
C20 C -0.35102(17) 0.9747(3) 0.0537(2) 0.0760(8) Uani 1 1 d . . .
H20A H -0.3456 1.0767 0.0808 0.091 Uiso 1 1 calc R . .
H20B H -0.4030 0.9697 -0.0166 0.091 Uiso 1 1 calc R . .
C21 C -0.26561(14) 0.9323(3) 0.03435(18) 0.0600(7) Uani 1 1 d . . .
H21A H -0.2730 0.8335 0.0013 0.072 Uiso 1 1 calc R . .
H21B H -0.2564 1.0024 -0.0176 0.072 Uiso 1 1 calc R . .
H2A H -0.0943(17) 0.616(3) 0.108(2) 0.086(9) 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
O1 C14 1.222(2) . ?
O2 C15 1.399(2) . ?
O2 H2A 0.93(3) . ?
N1 C13 1.320(3) . ?
N1 C7 1.359(3) . ?
N2 C14 1.361(3) . ?
N2 C15 1.463(2) . ?
N2 C16 1.469(3) . ?
C1 C2 1.370(3) . ?
C1 C6 1.390(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.355(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.409(3) . ?
C5 C10 1.419(3) . ?
C6 C7 1.450(3) . ?
C7 C8 1.415(3) . ?
C8 C11 1.414(3) . ?
C8 C9 1.425(3) . ?
C9 C10 1.353(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.352(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(3) . ?
C12 C15 1.510(3) . ?
C13 C14 1.486(3) . ?
C15 H15 0.9800 . ?
C16 C21 1.508(3) . ?
C16 C17 1.510(3) . ?
C16 H16 0.9800 . ?
C17 C18 1.516(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.505(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.494(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.523(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?

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
C15 O2 H2A 108.1(16) . . ?
C13 N1 C7 115.09(17) . . ?
C14 N2 C15 113.58(16) . . ?
C14 N2 C16 122.17(16) . . ?
C15 N2 C16 124.14(16) . . ?
C2 C1 C6 120.2(2) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C1 C2 C3 120.9(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 118.8(2) . . ?
C4 C5 C10 122.0(2) . . ?
C6 C5 C10 119.3(2) . . ?
C1 C6 C5 119.2(2) . . ?
C1 C6 C7 121.2(2) . . ?
C5 C6 C7 119.5(2) . . ?
N1 C7 C8 123.29(18) . . ?
N1 C7 C6 117.74(18) . . ?
C8 C7 C6 118.95(19) . . ?
C11 C8 C7 118.27(19) . . ?
C11 C8 C9 122.17(19) . . ?
C7 C8 C9 119.6(2) . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C5 121.8(2) . . ?
C9 C10 H10 119.1 . . ?
C5 C10 H10 119.1 . . ?
C12 C11 C8 117.93(19) . . ?
C12 C11 H11 121.0 . . ?
C8 C11 H11 121.0 . . ?
C11 C12 C13 119.32(19) . . ?
C11 C12 C15 131.59(19) . . ?
C13 C12 C15 108.96(17) . . ?
N1 C13 C12 126.08(19) . . ?
N1 C13 C14 124.94(17) . . ?
C12 C13 C14 108.91(17) . . ?
O1 C14 N2 125.26(19) . . ?
O1 C14 C13 128.57(18) . . ?
N2 C14 C13 106.15(16) . . ?
O2 C15 N2 112.78(16) . . ?
O2 C15 C12 113.38(17) . . ?
N2 C15 C12 102.33(15) . . ?
O2 C15 H15 109.4 . . ?
N2 C15 H15 109.4 . . ?
C12 C15 H15 109.4 . . ?
N2 C16 C21 112.30(16) . . ?
N2 C16 C17 111.83(18) . . ?
C21 C16 C17 110.55(19) . . ?
N2 C16 H16 107.3 . . ?
C21 C16 H16 107.3 . . ?
C17 C16 H16 107.3 . . ?
C16 C17 C18 111.4(2) . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 C17 112.7(2) . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C20 C19 C18 111.5(2) . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C19 C20 C21 111.5(2) . . ?
C19 C20 H20A 109.3 . . ?
C21 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C16 C21 C20 110.73(18) . . ?
C16 C21 H21A 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?

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
C6 C1 C2 C3 -0.9(4) . . . . ?
C1 C2 C3 C4 1.9(5) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 -1.8(4) . . . . ?
C3 C4 C5 C10 176.6(3) . . . . ?
C2 C1 C6 C5 -1.4(4) . . . . ?
C2 C1 C6 C7 179.8(2) . . . . ?
C4 C5 C6 C1 2.7(3) . . . . ?
C10 C5 C6 C1 -175.8(2) . . . . ?
C4 C5 C6 C7 -178.4(2) . . . . ?
C10 C5 C6 C7 3.1(3) . . . . ?
C13 N1 C7 C8 0.9(3) . . . . ?
C13 N1 C7 C6 -177.88(18) . . . . ?
C1 C6 C7 N1 -4.0(3) . . . . ?
C5 C6 C7 N1 177.16(18) . . . . ?
C1 C6 C7 C8 177.2(2) . . . . ?
C5 C6 C7 C8 -1.6(3) . . . . ?
N1 C7 C8 C11 -0.9(3) . . . . ?
C6 C7 C8 C11 177.82(19) . . . . ?
N1 C7 C8 C9 179.4(2) . . . . ?
C6 C7 C8 C9 -1.9(3) . . . . ?
C11 C8 C9 C10 -175.6(2) . . . . ?
C7 C8 C9 C10 4.0(3) . . . . ?
C8 C9 C10 C5 -2.6(4) . . . . ?
C4 C5 C10 C9 -179.5(2) . . . . ?
C6 C5 C10 C9 -1.0(4) . . . . ?
C7 C8 C11 C12 -0.3(3) . . . . ?
C9 C8 C11 C12 179.4(2) . . . . ?
C8 C11 C12 C13 1.3(3) . . . . ?
C8 C11 C12 C15 -174.0(2) . . . . ?
C7 N1 C13 C12 0.3(3) . . . . ?
C7 N1 C13 C14 176.96(18) . . . . ?
C11 C12 C13 N1 -1.5(3) . . . . ?
C15 C12 C13 N1 174.86(19) . . . . ?
C11 C12 C13 C14 -178.55(18) . . . . ?
C15 C12 C13 C14 -2.2(2) . . . . ?
C15 N2 C14 O1 -178.1(2) . . . . ?
C16 N2 C14 O1 -1.7(3) . . . . ?
C15 N2 C14 C13 0.7(2) . . . . ?
C16 N2 C14 C13 177.03(17) . . . . ?
N1 C13 C14 O1 2.6(4) . . . . ?
C12 C13 C14 O1 179.7(2) . . . . ?
N1 C13 C14 N2 -176.11(19) . . . . ?
C12 C13 C14 N2 1.0(2) . . . . ?
C14 N2 C15 O2 120.26(18) . . . . ?
C16 N2 C15 O2 -56.0(2) . . . . ?
C14 N2 C15 C12 -1.9(2) . . . . ?
C16 N2 C15 C12 -178.19(17) . . . . ?
C11 C12 C15 O2 56.4(3) . . . . ?
C13 C12 C15 O2 -119.29(19) . . . . ?
C11 C12 C15 N2 178.2(2) . . . . ?
C13 C12 C15 N2 2.5(2) . . . . ?
C14 N2 C16 C21 153.2(2) . . . . ?
C15 N2 C16 C21 -30.9(3) . . . . ?
C14 N2 C16 C17 -81.9(3) . . . . ?
C15 N2 C16 C17 94.1(2) . . . . ?
N2 C16 C17 C18 178.9(2) . . . . ?
C21 C16 C17 C18 -55.2(3) . . . . ?
C16 C17 C18 C19 53.2(3) . . . . ?
C17 C18 C19 C20 -52.6(4) . . . . ?
C18 C19 C20 C21 54.3(3) . . . . ?
N2 C16 C21 C20 -177.24(19) . . . . ?
C17 C16 C21 C20 57.1(3) . . . . ?
C19 C20 C21 C16 -57.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.036
