# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_km9
_database_code_depnum_ccdc_archive 'CCDC 1820608'
_audit_update_record             
;
2018-01-30 deposited with the CCDC.
2018-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H19 N O9'
_chemical_formula_weight         465.40

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'

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                   9.662(3)
_cell_length_b                   15.701(5)
_cell_length_c                   14.746(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.165(5)
_cell_angle_gamma                90.00
_cell_volume                     2231.1(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    31353
_cell_measurement_theta_min      1.97
_cell_measurement_theta_max      25.30

_exptl_crystal_description       block
_exptl_crystal_colour            transparent
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   'sadabs (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10349
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.30
_reflns_number_total             3967
_reflns_number_gt                2101
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SAINT'

_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 3.1'
_computing_publication_material  ?

_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)+(0.0834P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3967
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1697
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_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 -0.1339(2) 0.23771(15) 0.41417(15) 0.0700(7) Uani 1 1 d . . .
O2 O 0.3921(2) 0.06708(14) -0.08769(15) 0.0670(6) Uani 1 1 d . . .
O3 O -0.2650(2) 0.2539(2) 0.28662(15) 0.0989(10) Uani 1 1 d . . .
H3 H -0.3278 0.2466 0.3204 0.148 Uiso 1 1 calc R . .
O4 O 0.2348(2) 0.06124(14) 0.11003(16) 0.0708(7) Uani 1 1 d . . .
O5 O 0.1179(2) 0.10530(14) -0.01874(16) 0.0723(7) Uani 1 1 d . . .
O6 O 0.5734(2) 0.14809(15) -0.11483(16) 0.0796(8) Uani 1 1 d . . .
O7 O 0.4859(2) 0.33262(15) 0.17394(14) 0.0654(6) Uani 1 1 d . . .
H7 H 0.5479 0.2974 0.1836 0.098 Uiso 1 1 calc R . .
O8 O 0.5348(2) 0.34346(15) -0.12827(16) 0.0740(7) Uani 1 1 d . . .
O9 O 0.63432(18) 0.26672(13) 0.04682(13) 0.0541(6) Uani 1 1 d . . .
H9 H 0.6804 0.2573 0.0033 0.081 Uiso 1 1 calc R . .
N1 N 0.3063(2) 0.24372(15) 0.10775(16) 0.0496(6) Uani 1 1 d . . .
C1 C -0.1440(3) 0.2463(2) 0.3338(2) 0.0540(8) Uani 1 1 d . . .
C2 C -0.0273(3) 0.24949(17) 0.27389(19) 0.0470(7) Uani 1 1 d . . .
C3 C -0.0507(3) 0.25328(18) 0.1803(2) 0.0517(8) Uani 1 1 d . . .
H3A H -0.1411 0.2551 0.1541 0.062 Uiso 1 1 calc R . .
C4 C 0.0588(3) 0.25432(18) 0.1261(2) 0.0535(8) Uani 1 1 d . . .
H4 H 0.0427 0.2577 0.0633 0.064 Uiso 1 1 calc R . .
C5 C 0.1931(3) 0.25029(17) 0.1651(2) 0.0472(7) Uani 1 1 d . . .
C6 C 0.3137(3) 0.18299(18) 0.04296(19) 0.0451(7) Uani 1 1 d . . .
C7 C 0.4188(3) 0.19554(18) -0.01125(19) 0.0456(7) Uani 1 1 d . . .
C8 C 0.4692(3) 0.1367(2) -0.0758(2) 0.0504(8) Uani 1 1 d . . .
C9 C 0.4312(4) 0.0058(2) -0.1537(3) 0.0788(11) Uani 1 1 d . . .
H9A H 0.5207 -0.0189 -0.1347 0.095 Uiso 1 1 calc R . .
H9B H 0.4379 0.0330 -0.2122 0.095 Uiso 1 1 calc R . .
C10 C 0.3236(5) -0.0608(3) -0.1603(3) 0.1189(17) Uani 1 1 d . . .
H10A H 0.3160 -0.0860 -0.1016 0.178 Uiso 1 1 calc R . .
H10B H 0.3485 -0.1038 -0.2024 0.178 Uiso 1 1 calc R . .
H10C H 0.2363 -0.0359 -0.1812 0.178 Uiso 1 1 calc R . .
C11 C 0.1077(3) 0.2480(2) 0.3116(2) 0.0590(9) Uani 1 1 d . . .
H11 H 0.1243 0.2472 0.3745 0.071 Uiso 1 1 calc R . .
C12 C 0.2176(3) 0.2479(2) 0.2580(2) 0.0593(9) Uani 1 1 d . . .
H12 H 0.3080 0.2462 0.2843 0.071 Uiso 1 1 calc R . .
C13 C 0.2103(3) 0.11139(19) 0.0395(2) 0.0527(8) Uani 1 1 d . . .
C14 C 0.1378(5) -0.0095(3) 0.1190(3) 0.1014(14) Uani 1 1 d . . .
H14A H 0.0635 -0.0054 0.0713 0.122 Uiso 1 1 calc R . .
H14B H 0.1860 -0.0629 0.1112 0.122 Uiso 1 1 calc R . .
C15 C 0.0833(7) -0.0095(4) 0.2002(4) 0.190(3) Uani 1 1 d . . .
H15A H 0.1524 -0.0276 0.2463 0.285 Uiso 1 1 calc R . .
H15B H 0.0058 -0.0478 0.1986 0.285 Uiso 1 1 calc R . .
H15C H 0.0528 0.0469 0.2139 0.285 Uiso 1 1 calc R . .
C16 C 0.4933(3) 0.27667(18) 0.01592(19) 0.0454(7) Uani 1 1 d . . .
C17 C 0.4088(3) 0.31216(19) 0.09425(19) 0.0494(8) Uani 1 1 d . . .
C18 C 0.3367(3) 0.39047(19) 0.0550(2) 0.0584(9) Uani 1 1 d . . .
C19 C 0.3732(3) 0.4067(2) -0.0318(2) 0.0599(9) Uani 1 1 d . . .
C20 C 0.4747(3) 0.3438(2) -0.0587(2) 0.0552(8) Uani 1 1 d . . .
C21 C 0.3215(4) 0.4769(2) -0.0812(3) 0.0878(12) Uani 1 1 d . . .
H21 H 0.3470 0.4878 -0.1397 0.105 Uiso 1 1 calc R . .
C22 C 0.2298(5) 0.5298(3) -0.0392(4) 0.1071(16) Uani 1 1 d . . .
H22 H 0.1920 0.5768 -0.0704 0.128 Uiso 1 1 calc R . .
C23 C 0.1948(4) 0.5137(3) 0.0470(4) 0.1044(15) Uani 1 1 d . . .
H23 H 0.1343 0.5506 0.0736 0.125 Uiso 1 1 calc R . .
C24 C 0.2455(4) 0.4451(2) 0.0954(3) 0.0813(11) Uani 1 1 d . . .
H24 H 0.2200 0.4351 0.1541 0.098 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 1.190(3) . ?
O2 C8 1.328(3) . ?
O2 C9 1.438(4) . ?
O3 C1 1.322(3) . ?
O3 H3 0.8200 . ?
O4 C13 1.312(4) . ?
O4 C14 1.466(4) . ?
O5 C13 1.197(3) . ?
O6 C8 1.209(3) . ?
O7 C17 1.382(3) . ?
O7 H7 0.8200 . ?
O8 C20 1.215(3) . ?
O9 C16 1.413(3) . ?
O9 H9 0.8200 . ?
N1 C6 1.355(3) . ?
N1 C5 1.433(3) . ?
N1 C17 1.485(3) . ?
C1 C2 1.482(4) . ?
C2 C11 1.381(4) . ?
C2 C3 1.383(4) . ?
C3 C4 1.372(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C5 C12 1.375(4) . ?
C6 C7 1.352(4) . ?
C6 C13 1.502(4) . ?
C7 C8 1.436(4) . ?
C7 C16 1.503(4) . ?
C9 C10 1.472(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.368(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C14 C15 1.343(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C20 1.525(4) . ?
C16 C17 1.565(4) . ?
C17 C18 1.508(4) . ?
C18 C19 1.375(4) . ?
C18 C24 1.394(4) . ?
C19 C21 1.394(5) . ?
C19 C20 1.465(4) . ?
C21 C22 1.392(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.363(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.363(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 C9 117.9(2) . . ?
C1 O3 H3 109.5 . . ?
C13 O4 C14 116.5(3) . . ?
C17 O7 H7 109.5 . . ?
C16 O9 H9 109.5 . . ?
C6 N1 C5 123.2(2) . . ?
C6 N1 C17 110.2(2) . . ?
C5 N1 C17 124.9(2) . . ?
O1 C1 O3 122.6(3) . . ?
O1 C1 C2 125.9(3) . . ?
O3 C1 C2 111.5(3) . . ?
C11 C2 C3 118.9(3) . . ?
C11 C2 C1 119.8(3) . . ?
C3 C2 C1 121.3(3) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C12 C5 C4 120.3(3) . . ?
C12 C5 N1 120.2(2) . . ?
C4 C5 N1 119.5(3) . . ?
C7 C6 N1 113.3(2) . . ?
C7 C6 C13 128.0(3) . . ?
N1 C6 C13 118.8(2) . . ?
C6 C7 C8 127.1(3) . . ?
C6 C7 C16 109.4(2) . . ?
C8 C7 C16 122.9(2) . . ?
O6 C8 O2 122.5(3) . . ?
O6 C8 C7 123.7(3) . . ?
O2 C8 C7 113.8(2) . . ?
O2 C9 C10 107.5(3) . . ?
O2 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
O2 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C2 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C2 C11 H11 119.4 . . ?
C11 C12 C5 119.4(3) . . ?
C11 C12 H12 120.3 . . ?
C5 C12 H12 120.3 . . ?
O5 C13 O4 127.1(3) . . ?
O5 C13 C6 122.9(3) . . ?
O4 C13 C6 109.9(3) . . ?
C15 C14 O4 112.0(4) . . ?
C15 C14 H14A 109.2 . . ?
O4 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
O4 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O9 C16 C7 115.1(2) . . ?
O9 C16 C20 111.7(2) . . ?
C7 C16 C20 111.4(2) . . ?
O9 C16 C17 110.1(2) . . ?
C7 C16 C17 103.5(2) . . ?
C20 C16 C17 104.2(2) . . ?
O7 C17 N1 112.2(2) . . ?
O7 C17 C18 110.0(2) . . ?
N1 C17 C18 110.3(2) . . ?
O7 C17 C16 115.6(2) . . ?
N1 C17 C16 103.3(2) . . ?
C18 C17 C16 105.0(2) . . ?
C19 C18 C24 119.8(3) . . ?
C19 C18 C17 111.4(3) . . ?
C24 C18 C17 128.8(3) . . ?
C18 C19 C21 121.7(4) . . ?
C18 C19 C20 110.5(3) . . ?
C21 C19 C20 127.7(4) . . ?
O8 C20 C19 127.0(3) . . ?
O8 C20 C16 124.5(3) . . ?
C19 C20 C16 108.5(3) . . ?
C22 C21 C19 117.1(4) . . ?
C22 C21 H21 121.5 . . ?
C19 C21 H21 121.5 . . ?
C23 C22 C21 120.9(4) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 122.1(4) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 H23 119.0 . . ?
C23 C24 C18 118.4(4) . . ?
C23 C24 H24 120.8 . . ?
C18 C24 H24 120.8 . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.30
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.044
