# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_khd545h
_database_code_depnum_ccdc_archive 'CCDC 1889811'
_audit_update_record             
;
2019-01-09 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H23 N O6'
_chemical_formula_sum            'C23 H23 N O6'
_chemical_formula_weight         409.42

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.7557(18)
_cell_length_b                   14.297(3)
_cell_length_c                   16.454(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2059.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3569
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      24.99

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.096
_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            6186
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_av_sigmaI/netI    0.1415
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3569
_reflns_number_gt                1807
_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)+(0.0651P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3569
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1376
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1513
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_restrained_S_all      0.883
_refine_ls_shift/su_max          0.001
_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 0.0518(4) 0.3619(3) 0.1360(2) 0.0541(11) Uani 1 1 d . . .
O2 O 0.2904(5) 0.4546(3) 0.4045(3) 0.0758(13) Uani 1 1 d . . .
O3 O 0.2298(4) 0.3336(2) 0.3240(2) 0.0556(11) Uani 1 1 d . . .
O4 O 0.2786(4) 0.7693(2) 0.0743(2) 0.0542(10) Uani 1 1 d . . .
O5 O 0.1305(5) 0.8965(3) 0.0824(3) 0.0986(18) Uani 1 1 d . . .
O6 O 0.3600(5) 0.8981(3) 0.0255(3) 0.0696(12) Uani 1 1 d . . .
N1 N 0.1338(4) 0.5596(3) 0.1644(2) 0.0406(10) Uani 1 1 d . . .
C1 C 0.1776(6) 0.3893(4) 0.1529(3) 0.0415(12) Uani 1 1 d . . .
C2 C 0.2091(5) 0.4814(3) 0.2021(3) 0.0367(12) Uani 1 1 d . . .
C3 C 0.3849(6) 0.4819(4) 0.2044(3) 0.0393(13) Uani 1 1 d . . .
C4 C 0.4890(6) 0.5430(4) 0.2391(4) 0.0561(16) Uani 1 1 d . . .
H4 H 0.4567 0.5966 0.2663 0.067 Uiso 1 1 calc R . .
C5 C 0.6468(6) 0.5213(5) 0.2318(4) 0.0682(19) Uani 1 1 d . . .
H5 H 0.7172 0.5613 0.2559 0.082 Uiso 1 1 calc R . .
C6 C 0.6993(6) 0.4463(5) 0.1923(4) 0.0645(17) Uani 1 1 d . . .
H6 H 0.8041 0.4361 0.1893 0.077 Uiso 1 1 calc R . .
C7 C 0.5967(6) 0.3815(5) 0.1543(4) 0.0534(15) Uani 1 1 d . . .
C8 C 0.4402(6) 0.4032(4) 0.1639(3) 0.0414(13) Uani 1 1 d . . .
C9 C 0.3257(5) 0.3458(4) 0.1306(3) 0.0401(13) Uani 1 1 d . . .
C10 C 0.3633(7) 0.2670(4) 0.0889(3) 0.0571(16) Uani 1 1 d . . .
H10 H 0.2879 0.2283 0.0675 0.069 Uiso 1 1 calc R . .
C11 C 0.5193(8) 0.2455(5) 0.0788(4) 0.0671(19) Uani 1 1 d . . .
H11 H 0.5468 0.1923 0.0498 0.081 Uiso 1 1 calc R . .
C12 C 0.6305(8) 0.3011(5) 0.1106(4) 0.0690(19) Uani 1 1 d . . .
H12 H 0.7323 0.2847 0.1027 0.083 Uiso 1 1 calc R . .
C13 C 0.1363(6) 0.4813(3) 0.2873(3) 0.0371(12) Uani 1 1 d . . .
H13 H 0.0336 0.4544 0.2834 0.045 Uiso 1 1 calc R . .
C14 C 0.2267(6) 0.4254(4) 0.3471(3) 0.0454(14) Uani 1 1 d . . .
C15 C 0.3240(9) 0.2709(5) 0.3701(4) 0.093(2) Uani 1 1 d . . .
H15A H 0.4273 0.2746 0.3509 0.139 Uiso 1 1 calc R . .
H15B H 0.2870 0.2081 0.3638 0.139 Uiso 1 1 calc R . .
H15C H 0.3205 0.2881 0.4265 0.139 Uiso 1 1 calc R . .
C16 C 0.1219(6) 0.5854(3) 0.3079(3) 0.0406(12) Uani 1 1 d . . .
H16 H 0.2235 0.6083 0.3229 0.049 Uiso 1 1 calc R . .
C17 C 0.0147(6) 0.6079(4) 0.3768(3) 0.0595(17) Uani 1 1 d . . .
H17A H 0.0060 0.6745 0.3823 0.089 Uiso 1 1 calc R . .
H17B H 0.0538 0.5817 0.4263 0.089 Uiso 1 1 calc R . .
H17C H -0.0841 0.5818 0.3655 0.089 Uiso 1 1 calc R . .
C18 C 0.0805(5) 0.6278(4) 0.2267(3) 0.0450(14) Uani 1 1 d . . .
H18 H -0.0309 0.6326 0.2233 0.054 Uiso 1 1 calc R . .
C19 C 0.1488(6) 0.7205(3) 0.2027(3) 0.0504(15) Uani 1 1 d . . .
H19A H 0.2481 0.7296 0.2277 0.060 Uiso 1 1 calc R . .
H19B H 0.0824 0.7720 0.2178 0.060 Uiso 1 1 calc R . .
C20 C 0.1623(6) 0.7120(4) 0.1110(3) 0.0480(14) Uani 1 1 d . . .
H20 H 0.0632 0.7233 0.0851 0.058 Uiso 1 1 calc R . .
C21 C 0.2104(7) 0.6107(3) 0.0998(3) 0.0546(15) Uani 1 1 d . . .
H21A H 0.1788 0.5877 0.0469 0.066 Uiso 1 1 calc R . .
H21B H 0.3203 0.6044 0.1044 0.066 Uiso 1 1 calc R . .
C23 C 0.2425(7) 0.8594(4) 0.0629(4) 0.0527(15) Uani 1 1 d . . .
C24 C 0.3521(9) 0.9955(4) 0.0090(4) 0.087(2) Uani 1 1 d . . .
H24A H 0.2575 1.0094 -0.0179 0.131 Uiso 1 1 calc R . .
H24B H 0.4359 1.0131 -0.0254 0.131 Uiso 1 1 calc R . .
H24C H 0.3577 1.0297 0.0591 0.131 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.202(5) . ?
O2 C14 1.175(6) . ?
O3 C14 1.366(6) . ?
O3 C15 1.435(6) . ?
O4 C23 1.340(6) . ?
O4 C20 1.439(6) . ?
O5 C23 1.161(6) . ?
O6 C23 1.320(6) . ?
O6 C24 1.421(7) . ?
N1 C2 1.438(6) . ?
N1 C21 1.453(6) . ?
N1 C18 1.490(6) . ?
C1 C9 1.484(7) . ?
C1 C2 1.571(7) . ?
C2 C3 1.540(7) . ?
C2 C13 1.540(7) . ?
C3 C4 1.387(7) . ?
C3 C8 1.394(7) . ?
C4 C5 1.421(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.335(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.435(8) . ?
C6 H6 0.9300 . ?
C7 C12 1.387(8) . ?
C7 C8 1.414(7) . ?
C8 C9 1.407(7) . ?
C9 C10 1.359(7) . ?
C10 C11 1.410(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.362(9) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.494(7) . ?
C13 C16 1.531(6) . ?
C13 H13 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.506(6) . ?
C16 C18 1.511(7) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.507(7) . ?
C18 H18 0.9800 . ?
C19 C20 1.518(7) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.520(7) . ?
C20 H20 0.9800 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C14 O3 C15 117.7(5) . . ?
C23 O4 C20 116.0(4) . . ?
C23 O6 C24 117.5(5) . . ?
C2 N1 C21 119.6(4) . . ?
C2 N1 C18 110.8(4) . . ?
C21 N1 C18 108.6(4) . . ?
O1 C1 C9 127.4(5) . . ?
O1 C1 C2 123.6(4) . . ?
C9 C1 C2 109.0(4) . . ?
N1 C2 C3 117.8(4) . . ?
N1 C2 C13 101.8(4) . . ?
C3 C2 C13 113.0(4) . . ?
N1 C2 C1 110.4(4) . . ?
C3 C2 C1 101.0(4) . . ?
C13 C2 C1 113.3(4) . . ?
C4 C3 C8 118.5(5) . . ?
C4 C3 C2 132.1(5) . . ?
C8 C3 C2 109.4(4) . . ?
C3 C4 C5 117.8(6) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C6 C5 C4 123.5(6) . . ?
C6 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C5 C6 C7 121.0(6) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C12 C7 C8 116.6(6) . . ?
C12 C7 C6 128.8(6) . . ?
C8 C7 C6 114.6(6) . . ?
C3 C8 C9 114.2(4) . . ?
C3 C8 C7 124.6(5) . . ?
C9 C8 C7 121.2(5) . . ?
C10 C9 C8 120.6(5) . . ?
C10 C9 C1 133.1(5) . . ?
C8 C9 C1 106.3(4) . . ?
C9 C10 C11 118.3(6) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C12 C11 C10 121.4(6) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C7 122.0(6) . . ?
C11 C12 H12 119.0 . . ?
C7 C12 H12 119.0 . . ?
C14 C13 C16 114.7(4) . . ?
C14 C13 C2 112.4(4) . . ?
C16 C13 C2 103.5(4) . . ?
C14 C13 H13 108.7 . . ?
C16 C13 H13 108.7 . . ?
C2 C13 H13 108.7 . . ?
O2 C14 O3 123.8(5) . . ?
O2 C14 C13 126.2(5) . . ?
O3 C14 C13 110.0(5) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C18 115.5(4) . . ?
C17 C16 C13 115.2(4) . . ?
C18 C16 C13 102.4(4) . . ?
C17 C16 H16 107.8 . . ?
C18 C16 H16 107.8 . . ?
C13 C16 H16 107.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 C19 105.7(4) . . ?
N1 C18 C16 105.7(4) . . ?
C19 C18 C16 119.3(5) . . ?
N1 C18 H18 108.5 . . ?
C19 C18 H18 108.5 . . ?
C16 C18 H18 108.5 . . ?
C18 C19 C20 102.7(4) . . ?
C18 C19 H19A 111.2 . . ?
C20 C19 H19A 111.2 . . ?
C18 C19 H19B 111.2 . . ?
C20 C19 H19B 111.2 . . ?
H19A C19 H19B 109.1 . . ?
O4 C20 C19 115.2(4) . . ?
O4 C20 C21 107.2(4) . . ?
C19 C20 C21 102.7(4) . . ?
O4 C20 H20 110.5 . . ?
C19 C20 H20 110.5 . . ?
C21 C20 H20 110.5 . . ?
N1 C21 C20 105.2(4) . . ?
N1 C21 H21A 110.7 . . ?
C20 C21 H21A 110.7 . . ?
N1 C21 H21B 110.7 . . ?
C20 C21 H21B 110.7 . . ?
H21A C21 H21B 108.8 . . ?
O5 C23 O6 126.6(6) . . ?
O5 C23 O4 126.9(5) . . ?
O6 C23 O4 106.5(5) . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C21 N1 C2 C3 28.6(6) . . . . ?
C18 N1 C2 C3 -98.9(5) . . . . ?
C21 N1 C2 C13 152.7(4) . . . . ?
C18 N1 C2 C13 25.3(5) . . . . ?
C21 N1 C2 C1 -86.7(5) . . . . ?
C18 N1 C2 C1 145.8(4) . . . . ?
O1 C1 C2 N1 -53.9(6) . . . . ?
C9 C1 C2 N1 124.8(4) . . . . ?
O1 C1 C2 C3 -179.3(5) . . . . ?
C9 C1 C2 C3 -0.6(5) . . . . ?
O1 C1 C2 C13 59.5(6) . . . . ?
C9 C1 C2 C13 -121.7(4) . . . . ?
N1 C2 C3 C4 60.5(8) . . . . ?
C13 C2 C3 C4 -57.8(7) . . . . ?
C1 C2 C3 C4 -179.2(6) . . . . ?
N1 C2 C3 C8 -120.6(5) . . . . ?
C13 C2 C3 C8 121.1(4) . . . . ?
C1 C2 C3 C8 -0.3(5) . . . . ?
C8 C3 C4 C5 -0.6(8) . . . . ?
C2 C3 C4 C5 178.2(5) . . . . ?
C3 C4 C5 C6 1.3(10) . . . . ?
C4 C5 C6 C7 -0.5(10) . . . . ?
C5 C6 C7 C12 179.5(6) . . . . ?
C5 C6 C7 C8 -1.0(9) . . . . ?
C4 C3 C8 C9 -179.8(5) . . . . ?
C2 C3 C8 C9 1.1(6) . . . . ?
C4 C3 C8 C7 -1.0(8) . . . . ?
C2 C3 C8 C7 180.0(5) . . . . ?
C12 C7 C8 C3 -178.7(5) . . . . ?
C6 C7 C8 C3 1.8(8) . . . . ?
C12 C7 C8 C9 0.1(8) . . . . ?
C6 C7 C8 C9 -179.5(5) . . . . ?
C3 C8 C9 C10 179.5(5) . . . . ?
C7 C8 C9 C10 0.6(8) . . . . ?
C3 C8 C9 C1 -1.5(6) . . . . ?
C7 C8 C9 C1 179.7(5) . . . . ?
O1 C1 C9 C10 -1.3(9) . . . . ?
C2 C1 C9 C10 -179.9(5) . . . . ?
O1 C1 C9 C8 179.9(5) . . . . ?
C2 C1 C9 C8 1.2(5) . . . . ?
C8 C9 C10 C11 -1.0(8) . . . . ?
C1 C9 C10 C11 -179.8(5) . . . . ?
C9 C10 C11 C12 0.7(9) . . . . ?
C10 C11 C12 C7 -0.1(9) . . . . ?
C8 C7 C12 C11 -0.4(9) . . . . ?
C6 C7 C12 C11 179.2(6) . . . . ?
N1 C2 C13 C14 -162.8(4) . . . . ?
C3 C2 C13 C14 -35.5(6) . . . . ?
C1 C2 C13 C14 78.7(5) . . . . ?
N1 C2 C13 C16 -38.5(5) . . . . ?
C3 C2 C13 C16 88.8(5) . . . . ?
C1 C2 C13 C16 -157.0(4) . . . . ?
C15 O3 C14 O2 -3.8(8) . . . . ?
C15 O3 C14 C13 174.2(5) . . . . ?
C16 C13 C14 O2 -3.3(8) . . . . ?
C2 C13 C14 O2 114.6(6) . . . . ?
C16 C13 C14 O3 178.8(4) . . . . ?
C2 C13 C14 O3 -63.3(5) . . . . ?
C14 C13 C16 C17 -73.9(6) . . . . ?
C2 C13 C16 C17 163.3(4) . . . . ?
C14 C13 C16 C18 160.0(4) . . . . ?
C2 C13 C16 C18 37.2(5) . . . . ?
C2 N1 C18 C19 125.2(4) . . . . ?
C21 N1 C18 C19 -8.1(5) . . . . ?
C2 N1 C18 C16 -2.2(5) . . . . ?
C21 N1 C18 C16 -135.6(4) . . . . ?
C17 C16 C18 N1 -147.9(4) . . . . ?
C13 C16 C18 N1 -22.0(5) . . . . ?
C17 C16 C18 C19 93.3(6) . . . . ?
C13 C16 C18 C19 -140.7(4) . . . . ?
N1 C18 C19 C20 29.0(5) . . . . ?
C16 C18 C19 C20 147.8(4) . . . . ?
C23 O4 C20 C19 -79.8(6) . . . . ?
C23 O4 C20 C21 166.7(5) . . . . ?
C18 C19 C20 O4 -154.6(4) . . . . ?
C18 C19 C20 C21 -38.5(5) . . . . ?
C2 N1 C21 C20 -144.8(4) . . . . ?
C18 N1 C21 C20 -16.3(5) . . . . ?
O4 C20 C21 N1 155.9(4) . . . . ?
C19 C20 C21 N1 34.1(6) . . . . ?
C24 O6 C23 O5 2.0(10) . . . . ?
C24 O6 C23 O4 -177.7(5) . . . . ?
C20 O4 C23 O5 3.3(9) . . . . ?
C20 O4 C23 O6 -177.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_khc580h
_database_code_depnum_ccdc_archive 'CCDC 1889813'
_audit_update_record             
;
2019-01-09 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H26 N2 O4'
_chemical_formula_sum            'C28 H26 N2 O4'
_chemical_formula_weight         454.51

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.1876(16)
_cell_length_b                   14.121(3)
_cell_length_c                   19.915(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2302.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6053
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      29.15

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.088
_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      120(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            10660
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_av_sigmaI/netI    0.1469
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         29.15
_reflns_number_total             6053
_reflns_number_gt                3714
_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)+(0.0438P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration syn
_refine_ls_number_reflns         6053
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1373
_refine_ls_R_factor_gt           0.0795
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
C13 C 0.5183(4) 0.3700(3) 0.62135(19) 0.0277(8) Uani 1 1 d . . .
H13A H 0.4924 0.4114 0.5833 0.042 Uiso 1 1 calc R . .
H13B H 0.5566 0.4085 0.6592 0.042 Uiso 1 1 calc R . .
H13C H 0.4202 0.3350 0.6347 0.042 Uiso 1 1 calc R . .
O4 O 0.8347(3) -0.06030(17) 0.74746(12) 0.0298(6) Uani 1 1 d . . .
O3 O 0.8864(3) 0.09455(17) 0.75256(12) 0.0247(6) Uani 1 1 d . . .
O2 O 0.8333(3) 0.06782(18) 0.54373(11) 0.0259(6) Uani 1 1 d . . .
N2 N 0.8409(4) 0.0174(2) 0.65056(13) 0.0189(6) Uani 1 1 d . . .
O1 O 0.7939(3) 0.32383(17) 0.74425(13) 0.0273(6) Uani 1 1 d . . .
C25 C 1.0421(4) -0.3864(2) 0.58648(16) 0.0206(7) Uani 1 1 d . . .
H25 H 1.0960 -0.4354 0.6104 0.025 Uiso 1 1 calc R . .
C17 C 0.8545(4) 0.1911(2) 0.62688(16) 0.0176(7) Uani 1 1 d . . .
H17 H 0.9321 0.1939 0.6656 0.021 Uiso 1 1 calc R . .
C9 C 0.4891(4) 0.1535(2) 0.72242(16) 0.0180(7) Uani 1 1 d . . .
C11 C 0.6981(4) 0.2646(2) 0.72548(16) 0.0188(7) Uani 1 1 d . . .
C23 C 0.9707(4) -0.2208(2) 0.57557(16) 0.0164(7) Uani 1 1 d . . .
C10 C 0.5427(4) 0.1587(2) 0.65525(16) 0.0157(7) Uani 1 1 d . . .
C22 C 0.9820(4) -0.1204(2) 0.60023(16) 0.0189(7) Uani 1 1 d . . .
H22A H 1.0150 -0.0793 0.5623 0.023 Uiso 1 1 calc R . .
H22B H 1.0687 -0.1167 0.6348 0.023 Uiso 1 1 calc R . .
C21 C 0.8232(4) -0.0822(2) 0.63006(16) 0.0200(7) Uani 1 1 d . . .
H21 H 0.7315 -0.0892 0.5973 0.024 Uiso 1 1 calc R . .
N1 N 0.6457(3) 0.3034(2) 0.60183(14) 0.0202(6) Uani 1 1 d . . .
C15 C 0.9124(4) 0.2608(3) 0.57203(16) 0.0194(7) Uani 1 1 d . . .
H15 H 0.8923 0.2326 0.5267 0.023 Uiso 1 1 calc R . .
C19 C 0.8573(4) 0.0256(2) 0.72003(16) 0.0196(7) Uani 1 1 d . . .
C1 C 0.4637(4) 0.1072(3) 0.60737(17) 0.0223(8) Uani 1 1 d . . .
H1 H 0.4954 0.1112 0.5616 0.027 Uiso 1 1 calc R . .
C18 C 0.8438(4) 0.0897(2) 0.60221(16) 0.0181(7) Uani 1 1 d . . .
C4 C 0.3609(4) 0.0945(3) 0.74320(18) 0.0241(8) Uani 1 1 d . . .
C28 C 0.8868(4) -0.2424(3) 0.51671(15) 0.0193(7) Uani 1 1 d . . .
H28 H 0.8329 -0.1936 0.4925 0.023 Uiso 1 1 calc R . .
C24 C 1.0459(4) -0.2942(2) 0.61082(16) 0.0195(7) Uani 1 1 d . . .
H24 H 1.1003 -0.2810 0.6519 0.023 Uiso 1 1 calc R . .
C2 C 0.3328(5) 0.0475(3) 0.62746(19) 0.0273(8) Uani 1 1 d . . .
H2 H 0.2773 0.0117 0.5941 0.033 Uiso 1 1 calc R . .
C7 C 0.5342(4) 0.2151(3) 0.83259(16) 0.0268(9) Uani 1 1 d . . .
H7 H 0.5910 0.2551 0.8630 0.032 Uiso 1 1 calc R . .
C14 C 0.8010(4) 0.3460(3) 0.58196(18) 0.0235(8) Uani 1 1 d . . .
H14A H 0.8435 0.3884 0.6176 0.028 Uiso 1 1 calc R . .
H14B H 0.7893 0.3826 0.5398 0.028 Uiso 1 1 calc R . .
C26 C 0.9605(5) -0.4069(3) 0.52781(17) 0.0245(8) Uani 1 1 d . . .
H26 H 0.9583 -0.4699 0.5111 0.029 Uiso 1 1 calc R . .
C27 C 0.8816(5) -0.3352(3) 0.49332(16) 0.0236(8) Uani 1 1 d . . .
H27 H 0.8234 -0.3494 0.4533 0.028 Uiso 1 1 calc R . .
C12 C 0.6827(4) 0.2286(2) 0.65042(15) 0.0164(7) Uani 1 1 d . . .
C3 C 0.2836(4) 0.0395(3) 0.6928(2) 0.0265(9) Uani 1 1 d . . .
H3 H 0.1979 -0.0027 0.7044 0.032 Uiso 1 1 calc R . .
C5 C 0.3214(5) 0.0981(3) 0.81224(19) 0.0312(9) Uani 1 1 d . . .
H5 H 0.2351 0.0600 0.8291 0.037 Uiso 1 1 calc R . .
C8 C 0.5745(4) 0.2137(3) 0.76588(16) 0.0208(8) Uani 1 1 d . . .
C20 C 0.7780(5) -0.1270(3) 0.69734(19) 0.0350(10) Uani 1 1 d . . .
H20A H 0.6585 -0.1362 0.7008 0.042 Uiso 1 1 calc R . .
H20B H 0.8327 -0.1891 0.7028 0.042 Uiso 1 1 calc R . .
C6 C 0.4066(5) 0.1560(3) 0.85519(19) 0.0324(10) Uani 1 1 d . . .
H6 H 0.3788 0.1563 0.9015 0.039 Uiso 1 1 calc R . .
C16 C 1.0938(4) 0.2849(3) 0.57937(19) 0.0305(9) Uani 1 1 d . . .
H16A H 1.1136 0.3119 0.6240 0.046 Uiso 1 1 calc R . .
H16B H 1.1250 0.3309 0.5449 0.046 Uiso 1 1 calc R . .
H16C H 1.1590 0.2271 0.5740 0.046 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C13 N1 1.458(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O4 C19 1.343(4) . ?
O4 C20 1.449(4) . ?
O3 C19 1.194(4) . ?
O2 C18 1.208(4) . ?
N2 C19 1.395(4) . ?
N2 C18 1.404(4) . ?
N2 C21 1.472(4) . ?
O1 C11 1.206(4) . ?
C25 C26 1.377(5) . ?
C25 C24 1.389(5) . ?
C25 H25 0.9500 . ?
C17 C18 1.516(5) . ?
C17 C15 1.545(5) . ?
C17 C12 1.574(5) . ?
C17 H17 1.0000 . ?
C9 C8 1.400(5) . ?
C9 C4 1.404(5) . ?
C9 C10 1.410(5) . ?
C11 C8 1.480(5) . ?
C11 C12 1.584(4) . ?
C23 C28 1.393(4) . ?
C23 C24 1.395(5) . ?
C23 C22 1.503(5) . ?
C10 C1 1.362(5) . ?
C10 C12 1.516(5) . ?
C22 C21 1.528(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C21 C20 1.527(5) . ?
C21 H21 1.0000 . ?
N1 C14 1.462(4) . ?
N1 C12 1.464(4) . ?
C15 C14 1.523(5) . ?
C15 C16 1.531(5) . ?
C15 H15 1.0000 . ?
C1 C2 1.421(5) . ?
C1 H1 0.9500 . ?
C4 C5 1.413(5) . ?
C4 C3 1.417(5) . ?
C28 C27 1.391(5) . ?
C28 H28 0.9500 . ?
C24 H24 0.9500 . ?
C2 C3 1.367(5) . ?
C2 H2 0.9500 . ?
C7 C8 1.369(5) . ?
C7 C6 1.411(6) . ?
C7 H7 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C26 C27 1.384(5) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C3 H3 0.9500 . ?
C5 C6 1.374(6) . ?
C5 H5 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C6 H6 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 O4 C20 110.6(3) . . ?
C19 N2 C18 128.2(3) . . ?
C19 N2 C21 111.3(3) . . ?
C18 N2 C21 120.4(3) . . ?
C26 C25 C24 120.3(3) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C18 C17 C15 113.0(3) . . ?
C18 C17 C12 111.3(3) . . ?
C15 C17 C12 105.7(3) . . ?
C18 C17 H17 108.9 . . ?
C15 C17 H17 108.9 . . ?
C12 C17 H17 108.9 . . ?
C8 C9 C4 123.5(3) . . ?
C8 C9 C10 113.6(3) . . ?
C4 C9 C10 122.9(3) . . ?
O1 C11 C8 127.8(3) . . ?
O1 C11 C12 124.5(3) . . ?
C8 C11 C12 107.6(3) . . ?
C28 C23 C24 118.6(3) . . ?
C28 C23 C22 120.8(3) . . ?
C24 C23 C22 120.6(3) . . ?
C1 C10 C9 119.3(3) . . ?
C1 C10 C12 131.5(3) . . ?
C9 C10 C12 109.2(3) . . ?
C23 C22 C21 114.1(3) . . ?
C23 C22 H22A 108.7 . . ?
C21 C22 H22A 108.7 . . ?
C23 C22 H22B 108.7 . . ?
C21 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
N2 C21 C20 100.2(3) . . ?
N2 C21 C22 111.2(3) . . ?
C20 C21 C22 113.6(3) . . ?
N2 C21 H21 110.5 . . ?
C20 C21 H21 110.5 . . ?
C22 C21 H21 110.5 . . ?
C13 N1 C14 115.4(3) . . ?
C13 N1 C12 115.9(3) . . ?
C14 N1 C12 107.2(3) . . ?
C14 C15 C16 113.2(3) . . ?
C14 C15 C17 103.2(3) . . ?
C16 C15 C17 111.8(3) . . ?
C14 C15 H15 109.5 . . ?
C16 C15 H15 109.5 . . ?
C17 C15 H15 109.5 . . ?
O3 C19 O4 122.9(3) . . ?
O3 C19 N2 128.7(3) . . ?
O4 C19 N2 108.4(3) . . ?
C10 C1 C2 118.5(3) . . ?
C10 C1 H1 120.7 . . ?
C2 C1 H1 120.7 . . ?
O2 C18 N2 118.3(3) . . ?
O2 C18 C17 123.9(3) . . ?
N2 C18 C17 117.8(3) . . ?
C9 C4 C5 115.9(3) . . ?
C9 C4 C3 116.8(3) . . ?
C5 C4 C3 127.3(4) . . ?
C27 C28 C23 120.2(3) . . ?
C27 C28 H28 119.9 . . ?
C23 C28 H28 119.9 . . ?
C25 C24 C23 120.7(3) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C3 C2 C1 122.6(3) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C8 C7 C6 118.6(4) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
N1 C14 C15 103.3(3) . . ?
N1 C14 H14A 111.1 . . ?
C15 C14 H14A 111.1 . . ?
N1 C14 H14B 111.1 . . ?
C15 C14 H14B 111.1 . . ?
H14A C14 H14B 109.1 . . ?
C25 C26 C27 119.6(3) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C26 C27 C28 120.6(3) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
N1 C12 C10 110.8(3) . . ?
N1 C12 C17 103.3(3) . . ?
C10 C12 C17 118.4(3) . . ?
N1 C12 C11 114.1(3) . . ?
C10 C12 C11 102.1(3) . . ?
C17 C12 C11 108.5(3) . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 C11 133.2(3) . . ?
C9 C8 C11 107.5(3) . . ?
O4 C20 C21 104.9(3) . . ?
O4 C20 H20A 110.8 . . ?
C21 C20 H20A 110.8 . . ?
O4 C20 H20B 110.8 . . ?
C21 C20 H20B 110.8 . . ?
H20A C20 H20B 108.8 . . ?
C5 C6 C7 122.0(3) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C8 C9 C10 C1 -176.6(3) . . . . ?
C4 C9 C10 C1 2.6(5) . . . . ?
C8 C9 C10 C12 1.0(4) . . . . ?
C4 C9 C10 C12 -179.8(3) . . . . ?
C28 C23 C22 C21 73.4(4) . . . . ?
C24 C23 C22 C21 -107.4(4) . . . . ?
C19 N2 C21 C20 17.0(4) . . . . ?
C18 N2 C21 C20 -164.5(3) . . . . ?
C19 N2 C21 C22 -103.4(3) . . . . ?
C18 N2 C21 C22 75.0(4) . . . . ?
C23 C22 C21 N2 -177.6(3) . . . . ?
C23 C22 C21 C20 70.3(4) . . . . ?
C18 C17 C15 C14 137.9(3) . . . . ?
C12 C17 C15 C14 16.0(3) . . . . ?
C18 C17 C15 C16 -100.2(4) . . . . ?
C12 C17 C15 C16 137.9(3) . . . . ?
C20 O4 C19 O3 171.6(3) . . . . ?
C20 O4 C19 N2 -8.5(4) . . . . ?
C18 N2 C19 O3 -4.8(6) . . . . ?
C21 N2 C19 O3 173.6(3) . . . . ?
C18 N2 C19 O4 175.4(3) . . . . ?
C21 N2 C19 O4 -6.3(4) . . . . ?
C9 C10 C1 C2 -2.1(5) . . . . ?
C12 C10 C1 C2 -179.1(3) . . . . ?
C19 N2 C18 O2 177.4(3) . . . . ?
C21 N2 C18 O2 -0.8(5) . . . . ?
C19 N2 C18 C17 -4.6(5) . . . . ?
C21 N2 C18 C17 177.2(3) . . . . ?
C15 C17 C18 O2 -20.7(5) . . . . ?
C12 C17 C18 O2 98.0(4) . . . . ?
C15 C17 C18 N2 161.3(3) . . . . ?
C12 C17 C18 N2 -80.0(3) . . . . ?
C8 C9 C4 C5 -0.5(5) . . . . ?
C10 C9 C4 C5 -179.6(3) . . . . ?
C8 C9 C4 C3 178.3(3) . . . . ?
C10 C9 C4 C3 -0.8(5) . . . . ?
C24 C23 C28 C27 -1.3(5) . . . . ?
C22 C23 C28 C27 178.0(3) . . . . ?
C26 C25 C24 C23 -1.5(5) . . . . ?
C28 C23 C24 C25 2.2(5) . . . . ?
C22 C23 C24 C25 -177.0(3) . . . . ?
C10 C1 C2 C3 -0.2(5) . . . . ?
C13 N1 C14 C15 174.2(3) . . . . ?
C12 N1 C14 C15 43.3(3) . . . . ?
C16 C15 C14 N1 -156.3(3) . . . . ?
C17 C15 C14 N1 -35.3(3) . . . . ?
C24 C25 C26 C27 -0.3(5) . . . . ?
C25 C26 C27 C28 1.3(5) . . . . ?
C23 C28 C27 C26 -0.5(5) . . . . ?
C13 N1 C12 C10 69.6(4) . . . . ?
C14 N1 C12 C10 -159.8(3) . . . . ?
C13 N1 C12 C17 -162.6(3) . . . . ?
C14 N1 C12 C17 -32.1(3) . . . . ?
C13 N1 C12 C11 -45.0(4) . . . . ?
C14 N1 C12 C11 85.6(3) . . . . ?
C1 C10 C12 N1 54.0(5) . . . . ?
C9 C10 C12 N1 -123.2(3) . . . . ?
C1 C10 C12 C17 -65.0(5) . . . . ?
C9 C10 C12 C17 117.7(3) . . . . ?
C1 C10 C12 C11 175.9(4) . . . . ?
C9 C10 C12 C11 -1.3(3) . . . . ?
C18 C17 C12 N1 -114.2(3) . . . . ?
C15 C17 C12 N1 8.8(3) . . . . ?
C18 C17 C12 C10 8.7(4) . . . . ?
C15 C17 C12 C10 131.7(3) . . . . ?
C18 C17 C12 C11 124.3(3) . . . . ?
C15 C17 C12 C11 -112.7(3) . . . . ?
O1 C11 C12 N1 -58.6(4) . . . . ?
C8 C11 C12 N1 120.7(3) . . . . ?
O1 C11 C12 C10 -178.1(3) . . . . ?
C8 C11 C12 C10 1.1(3) . . . . ?
O1 C11 C12 C17 56.1(4) . . . . ?
C8 C11 C12 C17 -124.6(3) . . . . ?
C1 C2 C3 C4 2.0(6) . . . . ?
C9 C4 C3 C2 -1.5(5) . . . . ?
C5 C4 C3 C2 177.2(4) . . . . ?
C9 C4 C5 C6 -0.5(5) . . . . ?
C3 C4 C5 C6 -179.2(4) . . . . ?
C6 C7 C8 C9 -0.4(5) . . . . ?
C6 C7 C8 C11 -179.9(4) . . . . ?
C4 C9 C8 C7 0.9(5) . . . . ?
C10 C9 C8 C7 -179.9(3) . . . . ?
C4 C9 C8 C11 -179.4(3) . . . . ?
C10 C9 C8 C11 -0.2(4) . . . . ?
O1 C11 C8 C7 -1.8(6) . . . . ?
C12 C11 C8 C7 178.9(4) . . . . ?
O1 C11 C8 C9 178.6(3) . . . . ?
C12 C11 C8 C9 -0.6(3) . . . . ?
C19 O4 C20 C21 19.2(4) . . . . ?
N2 C21 C20 O4 -20.7(4) . . . . ?
C22 C21 C20 O4 97.9(3) . . . . ?
C4 C5 C6 C7 1.0(6) . . . . ?
C8 C7 C6 C5 -0.5(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.15
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_khc646h
_database_code_depnum_ccdc_archive 'CCDC 1889812'
_audit_update_record             
;
2019-01-09 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H28 N2 O4'
_chemical_formula_sum            'C30 H28 N2 O4'
_chemical_formula_weight         480.54

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.5232(17)
_cell_length_b                   13.562(3)
_cell_length_c                   21.283(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2460.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6612
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      29.17

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    0.086
_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      120(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            11669
_diffrn_reflns_av_R_equivalents  0.1352
_diffrn_reflns_av_sigmaI/netI    0.1831
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         29.17
_reflns_number_total             6612
_reflns_number_gt                3314
_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)+(0.0517P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_chemical_absolute_configuration syn
_refine_ls_number_reflns         6612
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1896
_refine_ls_R_factor_gt           0.0968
_refine_ls_wR_factor_ref         0.1779
_refine_ls_wR_factor_gt          0.1485
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.2982(4) 0.1919(2) 0.73986(13) 0.0350(7) Uani 1 1 d . . .
O2 O 0.2824(4) 0.4401(2) 0.93441(13) 0.0350(8) Uani 1 1 d . . .
O3 O 0.3706(4) 0.4135(3) 0.74146(14) 0.0443(9) Uani 1 1 d . . .
O4 O 0.3650(4) 0.5781(2) 0.74769(13) 0.0379(8) Uani 1 1 d . . .
N1 N 0.1184(4) 0.1854(3) 0.85805(17) 0.0334(9) Uani 1 1 d . . .
N2 N 0.3366(4) 0.4947(3) 0.83682(15) 0.0281(8) Uani 1 1 d . . .
C1 C 0.1915(5) 0.2433(3) 0.75682(19) 0.0271(9) Uani 1 1 d . . .
C2 C 0.0628(5) 0.2860(3) 0.71890(19) 0.0289(10) Uani 1 1 d . . .
C3 C 0.0247(6) 0.2770(4) 0.6560(2) 0.0451(13) Uani 1 1 d . . .
H3 H 0.0837 0.2358 0.6287 0.054 Uiso 1 1 calc R . .
C4 C -0.1047(7) 0.3311(5) 0.6341(3) 0.065(2) Uani 1 1 d . . .
H4 H -0.1333 0.3254 0.5911 0.079 Uiso 1 1 calc R . .
C5 C -0.1921(7) 0.3922(4) 0.6724(3) 0.0611(18) Uani 1 1 d . . .
H5 H -0.2793 0.4268 0.6554 0.073 Uiso 1 1 calc R . .
C6 C -0.1538(5) 0.4040(4) 0.7362(3) 0.0451(13) Uani 1 1 d . . .
C7 C -0.0264(5) 0.3479(3) 0.7579(2) 0.0304(10) Uani 1 1 d . . .
C8 C -0.2273(6) 0.4652(4) 0.7817(3) 0.0587(17) Uani 1 1 d . . .
H8 H -0.3144 0.5049 0.7702 0.070 Uiso 1 1 calc R . .
C9 C -0.1724(6) 0.4667(4) 0.8419(3) 0.0624(18) Uani 1 1 d . . .
H9 H -0.2228 0.5085 0.8715 0.075 Uiso 1 1 calc R . .
C10 C -0.0465(5) 0.4101(4) 0.8618(3) 0.0491(14) Uani 1 1 d . . .
H10 H -0.0126 0.4132 0.9043 0.059 Uiso 1 1 calc R . .
C11 C 0.0290(5) 0.3495(3) 0.8199(2) 0.0321(11) Uani 1 1 d . . .
C12 C 0.1625(5) 0.2777(3) 0.82656(19) 0.0270(10) Uani 1 1 d . . .
C13 C -0.0131(7) 0.1842(5) 0.9017(3) 0.0627(17) Uani 1 1 d . . .
H13A H -0.1148 0.1855 0.8792 0.075 Uiso 1 1 calc R . .
H13B H -0.0082 0.2403 0.9314 0.075 Uiso 1 1 calc R . .
C14 C 0.0120(7) 0.0870(5) 0.9349(3) 0.0640(17) Uani 1 1 d . . .
H14A H -0.0456 0.0849 0.9752 0.077 Uiso 1 1 calc R . .
H14B H -0.0217 0.0310 0.9083 0.077 Uiso 1 1 calc R . .
C15 C 0.1872(7) 0.0856(4) 0.9454(2) 0.0526(15) Uani 1 1 d . . .
H15A H 0.2279 0.0172 0.9438 0.063 Uiso 1 1 calc R . .
H15B H 0.2139 0.1146 0.9867 0.063 Uiso 1 1 calc R . .
C16 C 0.2567(5) 0.1477(4) 0.8918(2) 0.0341(11) Uani 1 1 d . . .
H16 H 0.3206 0.1049 0.8634 0.041 Uiso 1 1 calc R . .
C17 C 0.3515(5) 0.2392(3) 0.9108(2) 0.0340(11) Uani 1 1 d . . .
H17 H 0.3070 0.2665 0.9507 0.041 Uiso 1 1 calc R . .
C18 C 0.5250(6) 0.2176(4) 0.9207(3) 0.0547(16) Uani 1 1 d . . .
H18A H 0.5807 0.2792 0.9298 0.082 Uiso 1 1 calc R . .
H18B H 0.5686 0.1877 0.8826 0.082 Uiso 1 1 calc R . .
H18C H 0.5376 0.1720 0.9560 0.082 Uiso 1 1 calc R . .
C19 C 0.3201(5) 0.3119(3) 0.85775(19) 0.0299(10) Uani 1 1 d . . .
H19 H 0.4061 0.3058 0.8261 0.036 Uiso 1 1 calc R . .
C20 C 0.3128(5) 0.4188(4) 0.88015(19) 0.0296(10) Uani 1 1 d . . .
C21 C 0.3584(5) 0.4873(4) 0.7723(2) 0.0324(11) Uani 1 1 d . . .
C22 C 0.3250(5) 0.6511(3) 0.79469(19) 0.0332(11) Uani 1 1 d . . .
H22A H 0.2175 0.6764 0.7877 0.040 Uiso 1 1 calc R . .
H22B H 0.3993 0.7071 0.7931 0.040 Uiso 1 1 calc R . .
C23 C 0.3358(5) 0.5985(3) 0.85801(19) 0.0278(10) Uani 1 1 d . . .
H23 H 0.2407 0.6124 0.8841 0.033 Uiso 1 1 calc R . .
C24 C 0.4852(5) 0.6226(3) 0.8946(2) 0.0296(10) Uani 1 1 d . . .
H24A H 0.4983 0.5733 0.9286 0.036 Uiso 1 1 calc R . .
H24B H 0.5763 0.6164 0.8660 0.036 Uiso 1 1 calc R . .
C25 C 0.4864(5) 0.7252(3) 0.9236(2) 0.0261(10) Uani 1 1 d . . .
C26 C 0.5724(5) 0.8005(4) 0.8955(2) 0.0331(11) Uani 1 1 d . . .
H26 H 0.6274 0.7879 0.8575 0.040 Uiso 1 1 calc R . .
C27 C 0.5790(6) 0.8931(4) 0.9221(2) 0.0414(12) Uani 1 1 d . . .
H27 H 0.6384 0.9438 0.9025 0.050 Uiso 1 1 calc R . .
C28 C 0.4992(6) 0.9119(4) 0.9771(2) 0.0414(12) Uani 1 1 d . . .
H28 H 0.5065 0.9749 0.9965 0.050 Uiso 1 1 calc R . .
C29 C 0.4091(7) 0.8391(4) 1.0039(2) 0.0455(13) Uani 1 1 d . . .
H29 H 0.3510 0.8531 1.0409 0.055 Uiso 1 1 calc R . .
C30 C 0.4019(5) 0.7457(4) 0.97762(19) 0.0326(11) Uani 1 1 d . . .
H30 H 0.3392 0.6960 0.9966 0.039 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.201(5) . ?
O2 C20 1.218(5) . ?
O3 C21 1.201(6) . ?
O4 C21 1.339(6) . ?
O4 C22 1.448(5) . ?
N1 C13 1.455(6) . ?
N1 C12 1.468(5) . ?
N1 C16 1.472(5) . ?
N2 C21 1.390(5) . ?
N2 C20 1.397(6) . ?
N2 C23 1.478(6) . ?
C1 C2 1.480(6) . ?
C1 C12 1.576(6) . ?
C2 C3 1.383(6) . ?
C2 C7 1.403(6) . ?
C3 C4 1.404(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.407(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.403(6) . ?
C6 C8 1.420(8) . ?
C7 C11 1.402(6) . ?
C8 C9 1.365(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.373(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.505(6) . ?
C12 C19 1.568(6) . ?
C13 C14 1.510(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.510(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.536(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.536(7) . ?
C16 H16 1.0000 . ?
C17 C18 1.522(7) . ?
C17 C19 1.523(6) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.528(6) . ?
C19 H19 1.0000 . ?
C22 C23 1.528(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.529(6) . ?
C23 H23 1.0000 . ?
C24 C25 1.522(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C30 1.385(6) . ?
C25 C26 1.392(6) . ?
C26 C27 1.378(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.378(7) . ?
C27 H27 0.9500 . ?
C28 C29 1.374(8) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(7) . ?
C29 H29 0.9500 . ?
C30 H30 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
C21 O4 C22 110.4(3) . . ?
C13 N1 C12 119.9(4) . . ?
C13 N1 C16 107.5(4) . . ?
C12 N1 C16 108.3(3) . . ?
C21 N2 C20 128.2(4) . . ?
C21 N2 C23 111.8(4) . . ?
C20 N2 C23 120.0(3) . . ?
O1 C1 C2 128.6(4) . . ?
O1 C1 C12 125.0(4) . . ?
C2 C1 C12 106.3(3) . . ?
C3 C2 C7 119.9(5) . . ?
C3 C2 C1 131.8(5) . . ?
C7 C2 C1 108.3(3) . . ?
C2 C3 C4 117.4(5) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C5 C4 C3 122.7(5) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C4 C5 C6 120.9(5) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 115.8(5) . . ?
C7 C6 C8 115.7(5) . . ?
C5 C6 C8 128.5(5) . . ?
C11 C7 C2 112.6(4) . . ?
C11 C7 C6 124.1(5) . . ?
C2 C7 C6 123.3(4) . . ?
C9 C8 C6 119.9(5) . . ?
C9 C8 H8 120.1 . . ?
C6 C8 H8 120.1 . . ?
C8 C9 C10 122.9(5) . . ?
C8 C9 H9 118.5 . . ?
C10 C9 H9 118.5 . . ?
C11 C10 C9 119.7(5) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C7 117.6(4) . . ?
C10 C11 C12 132.9(4) . . ?
C7 C11 C12 109.5(4) . . ?
N1 C12 C11 113.7(3) . . ?
N1 C12 C19 106.1(3) . . ?
C11 C12 C19 119.7(3) . . ?
N1 C12 C1 102.6(3) . . ?
C11 C12 C1 102.8(3) . . ?
C19 C12 C1 110.6(3) . . ?
N1 C13 C14 101.5(4) . . ?
N1 C13 H13A 111.5 . . ?
C14 C13 H13A 111.5 . . ?
N1 C13 H13B 111.5 . . ?
C14 C13 H13B 111.5 . . ?
H13A C13 H13B 109.3 . . ?
C15 C14 C13 102.8(5) . . ?
C15 C14 H14A 111.2 . . ?
C13 C14 H14A 111.2 . . ?
C15 C14 H14B 111.2 . . ?
C13 C14 H14B 111.2 . . ?
H14A C14 H14B 109.1 . . ?
C14 C15 C16 105.3(4) . . ?
C14 C15 H15A 110.7 . . ?
C16 C15 H15A 110.7 . . ?
C14 C15 H15B 110.7 . . ?
C16 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
N1 C16 C15 104.2(4) . . ?
N1 C16 C17 105.6(4) . . ?
C15 C16 C17 116.8(4) . . ?
N1 C16 H16 110.0 . . ?
C15 C16 H16 110.0 . . ?
C17 C16 H16 110.0 . . ?
C18 C17 C19 113.4(4) . . ?
C18 C17 C16 113.1(4) . . ?
C19 C17 C16 103.6(3) . . ?
C18 C17 H17 108.8 . . ?
C19 C17 H17 108.8 . . ?
C16 C17 H17 108.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 C20 112.9(3) . . ?
C17 C19 C12 105.9(4) . . ?
C20 C19 C12 112.2(3) . . ?
C17 C19 H19 108.6 . . ?
C20 C19 H19 108.6 . . ?
C12 C19 H19 108.6 . . ?
O2 C20 N2 118.9(4) . . ?
O2 C20 C19 121.9(4) . . ?
N2 C20 C19 119.2(3) . . ?
O3 C21 O4 123.3(4) . . ?
O3 C21 N2 127.7(5) . . ?
O4 C21 N2 109.0(4) . . ?
O4 C22 C23 106.0(3) . . ?
O4 C22 H22A 110.5 . . ?
C23 C22 H22A 110.5 . . ?
O4 C22 H22B 110.5 . . ?
C23 C22 H22B 110.5 . . ?
H22A C22 H22B 108.7 . . ?
N2 C23 C22 100.1(3) . . ?
N2 C23 C24 110.8(3) . . ?
C22 C23 C24 113.6(4) . . ?
N2 C23 H23 110.6 . . ?
C22 C23 H23 110.6 . . ?
C24 C23 H23 110.6 . . ?
C25 C24 C23 114.0(3) . . ?
C25 C24 H24A 108.7 . . ?
C23 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
C23 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C30 C25 C26 118.9(4) . . ?
C30 C25 C24 121.1(4) . . ?
C26 C25 C24 120.0(4) . . ?
C27 C26 C25 120.9(4) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C28 C27 C26 119.8(5) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C29 C28 C27 119.7(5) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C28 C29 C30 120.9(5) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 H29 119.5 . . ?
C25 C30 C29 119.7(5) . . ?
C25 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?

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
O1 C1 C2 C3 2.8(8) . . . . ?
C12 C1 C2 C3 -176.7(5) . . . . ?
O1 C1 C2 C7 -174.9(4) . . . . ?
C12 C1 C2 C7 5.6(4) . . . . ?
C7 C2 C3 C4 -0.3(7) . . . . ?
C1 C2 C3 C4 -177.9(4) . . . . ?
C2 C3 C4 C5 0.6(8) . . . . ?
C3 C4 C5 C6 0.6(9) . . . . ?
C4 C5 C6 C7 -1.9(7) . . . . ?
C4 C5 C6 C8 178.2(5) . . . . ?
C3 C2 C7 C11 -179.3(4) . . . . ?
C1 C2 C7 C11 -1.2(5) . . . . ?
C3 C2 C7 C6 -1.1(7) . . . . ?
C1 C2 C7 C6 177.0(4) . . . . ?
C5 C6 C7 C11 -179.9(4) . . . . ?
C8 C6 C7 C11 0.1(7) . . . . ?
C5 C6 C7 C2 2.2(7) . . . . ?
C8 C6 C7 C2 -177.9(4) . . . . ?
C7 C6 C8 C9 0.2(7) . . . . ?
C5 C6 C8 C9 -179.9(5) . . . . ?
C6 C8 C9 C10 -0.4(9) . . . . ?
C8 C9 C10 C11 0.3(9) . . . . ?
C9 C10 C11 C7 -0.1(8) . . . . ?
C9 C10 C11 C12 -177.5(5) . . . . ?
C2 C7 C11 C10 178.0(4) . . . . ?
C6 C7 C11 C10 -0.1(7) . . . . ?
C2 C7 C11 C12 -3.9(5) . . . . ?
C6 C7 C11 C12 177.9(4) . . . . ?
C13 N1 C12 C11 -25.9(6) . . . . ?
C16 N1 C12 C11 -149.6(4) . . . . ?
C13 N1 C12 C19 107.8(5) . . . . ?
C16 N1 C12 C19 -16.0(4) . . . . ?
C13 N1 C12 C1 -136.1(4) . . . . ?
C16 N1 C12 C1 100.1(4) . . . . ?
C10 C11 C12 N1 74.5(7) . . . . ?
C7 C11 C12 N1 -103.1(4) . . . . ?
C10 C11 C12 C19 -52.4(7) . . . . ?
C7 C11 C12 C19 130.0(4) . . . . ?
C10 C11 C12 C1 -175.5(5) . . . . ?
C7 C11 C12 C1 6.9(5) . . . . ?
O1 C1 C12 N1 -68.8(5) . . . . ?
C2 C1 C12 N1 110.7(4) . . . . ?
O1 C1 C12 C11 173.0(4) . . . . ?
C2 C1 C12 C11 -7.5(4) . . . . ?
O1 C1 C12 C19 44.0(5) . . . . ?
C2 C1 C12 C19 -136.4(4) . . . . ?
C12 N1 C13 C14 -165.2(4) . . . . ?
C16 N1 C13 C14 -41.0(6) . . . . ?
N1 C13 C14 C15 41.9(6) . . . . ?
C13 C14 C15 C16 -28.2(6) . . . . ?
C13 N1 C16 C15 23.2(5) . . . . ?
C12 N1 C16 C15 154.1(4) . . . . ?
C13 N1 C16 C17 -100.4(4) . . . . ?
C12 N1 C16 C17 30.5(4) . . . . ?
C14 C15 C16 N1 4.0(5) . . . . ?
C14 C15 C16 C17 120.0(5) . . . . ?
N1 C16 C17 C18 -155.5(4) . . . . ?
C15 C16 C17 C18 89.3(5) . . . . ?
N1 C16 C17 C19 -32.3(4) . . . . ?
C15 C16 C17 C19 -147.5(4) . . . . ?
C18 C17 C19 C20 -91.6(5) . . . . ?
C16 C17 C19 C20 145.4(4) . . . . ?
C18 C17 C19 C12 145.2(4) . . . . ?
C16 C17 C19 C12 22.2(4) . . . . ?
N1 C12 C19 C17 -4.7(4) . . . . ?
C11 C12 C19 C17 125.6(4) . . . . ?
C1 C12 C19 C17 -115.2(4) . . . . ?
N1 C12 C19 C20 -128.3(4) . . . . ?
C11 C12 C19 C20 2.0(5) . . . . ?
C1 C12 C19 C20 121.2(4) . . . . ?
C21 N2 C20 O2 -173.7(4) . . . . ?
C23 N2 C20 O2 4.3(6) . . . . ?
C21 N2 C20 C19 4.2(6) . . . . ?
C23 N2 C20 C19 -177.8(4) . . . . ?
C17 C19 C20 O2 -23.1(6) . . . . ?
C12 C19 C20 O2 96.5(5) . . . . ?
C17 C19 C20 N2 159.1(4) . . . . ?
C12 C19 C20 N2 -81.4(5) . . . . ?
C22 O4 C21 O3 172.1(4) . . . . ?
C22 O4 C21 N2 -8.2(5) . . . . ?
C20 N2 C21 O3 -5.0(7) . . . . ?
C23 N2 C21 O3 176.8(4) . . . . ?
C20 N2 C21 O4 175.3(4) . . . . ?
C23 N2 C21 O4 -2.9(5) . . . . ?
C21 O4 C22 C23 15.5(4) . . . . ?
C21 N2 C23 C22 11.6(4) . . . . ?
C20 N2 C23 C22 -166.7(4) . . . . ?
C21 N2 C23 C24 -108.6(4) . . . . ?
C20 N2 C23 C24 73.1(5) . . . . ?
O4 C22 C23 N2 -15.6(4) . . . . ?
O4 C22 C23 C24 102.6(4) . . . . ?
N2 C23 C24 C25 -174.3(4) . . . . ?
C22 C23 C24 C25 73.9(5) . . . . ?
C23 C24 C25 C30 76.9(5) . . . . ?
C23 C24 C25 C26 -102.6(5) . . . . ?
C30 C25 C26 C27 2.5(7) . . . . ?
C24 C25 C26 C27 -177.9(4) . . . . ?
C25 C26 C27 C28 -0.2(7) . . . . ?
C26 C27 C28 C29 -2.3(7) . . . . ?
C27 C28 C29 C30 2.4(7) . . . . ?
C26 C25 C30 C29 -2.4(6) . . . . ?
C24 C25 C30 C29 178.0(4) . . . . ?
C28 C29 C30 C25 0.0(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        29.17
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.054
