# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_KB454_0m
_database_code_depnum_ccdc_archive 'CCDC 2171885'
loop_
_audit_author_name
_audit_author_address
'Balasubramanian Sridhar'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-05-10 deposited with the CCDC.	2022-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H31 N O4'
_chemical_formula_sum            'C27 H31 N O4'
_chemical_formula_weight         433.53

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0686(7)
_cell_length_b                   10.3684(7)
_cell_length_c                   12.3317(8)
_cell_angle_alpha                72.123(2)
_cell_angle_beta                 80.904(2)
_cell_angle_gamma                87.167(2)
_cell_volume                     1209.80(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    8497
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      29.4

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6384
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23595
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.892
_diffrn_reflns_theta_max         30.548
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             7363
_reflns_number_gt                4567
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+0.3307P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7363
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1382
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.964
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.11199(13) 0.73026(12) 0.38786(12) 0.0367(3) Uani 1 1 d . . . . .
C2 C 0.20193(13) 0.68155(12) 0.29478(11) 0.0366(3) Uani 1 1 d . . . . .
C3 C 0.29196(12) 0.59231(12) 0.34418(11) 0.0332(3) Uani 1 1 d . . . . .
C4 C 0.26605(13) 0.56819(12) 0.47120(11) 0.0343(3) Uani 1 1 d . . . . .
C5 C 0.13617(15) 0.87736(14) 0.37167(14) 0.0478(4) Uani 1 1 d . . . . .
H5 H 0.223477 0.904668 0.369234 0.057 Uiso 1 1 calc R U . . .
C6 C 0.04032(17) 0.96975(15) 0.36073(14) 0.0528(4) Uani 1 1 d . . . . .
H6 H 0.062154 1.058947 0.351656 0.063 Uiso 1 1 calc R U . . .
C7 C -0.09939(17) 0.93582(16) 0.36248(14) 0.0541(4) Uani 1 1 d . . . . .
C8 C -0.12821(15) 0.79312(16) 0.37782(13) 0.0487(3) Uani 1 1 d . . . . .
H8 H -0.215792 0.767719 0.378763 0.058 Uiso 1 1 calc R U . . .
C9 C -0.03262(13) 0.70035(14) 0.39027(12) 0.0415(3) Uani 1 1 d . . . . .
H9 H -0.056403 0.611217 0.401185 0.050 Uiso 1 1 calc R U . . .
C10 C 0.17295(14) 0.72683(15) 0.17471(12) 0.0452(3) Uani 1 1 d . . . . .
C11 C 0.17833(19) 0.86269(18) 0.10912(15) 0.0662(5) Uani 1 1 d . . . . .
H11 H 0.202005 0.928001 0.140095 0.079 Uiso 1 1 calc R U . . .
C12 C 0.1485(2) 0.9008(3) -0.00236(18) 0.0864(7) Uani 1 1 d . . . . .
H12 H 0.153048 0.991699 -0.046079 0.104 Uiso 1 1 calc R U . . .
C13 C 0.1122(2) 0.8057(3) -0.04868(18) 0.0918(8) Uani 1 1 d . . . . .
H13 H 0.092173 0.831936 -0.123489 0.110 Uiso 1 1 calc R U . . .
C14 C 0.1056(2) 0.6718(3) 0.01567(18) 0.0835(6) Uani 1 1 d . . . . .
H14 H 0.080743 0.607253 -0.015670 0.100 Uiso 1 1 calc R U . . .
C15 C 0.13553(18) 0.63183(19) 0.12681(14) 0.0605(4) Uani 1 1 d . . . . .
H15 H 0.130568 0.540699 0.169760 0.073 Uiso 1 1 calc R U . . .
C16 C 0.40630(12) 0.51568(12) 0.29745(10) 0.0330(3) Uani 1 1 d . . . . .
H16 H 0.479306 0.508765 0.342918 0.040 Uiso 1 1 calc R U . . .
C17 C 0.46124(13) 0.58920(13) 0.17026(11) 0.0364(3) Uani 1 1 d . . . . .
C18 C 0.56158(15) 0.70671(14) 0.14080(12) 0.0451(3) Uani 1 1 d . . . . .
C19 C 0.5358(2) 0.79277(18) 0.22271(17) 0.0673(5) Uani 1 1 d . . . . .
H19A H 0.605183 0.859887 0.203095 0.101 Uiso 1 1 calc R U . . .
H19B H 0.536113 0.735752 0.300464 0.101 Uiso 1 1 calc R U . . .
H19C H 0.450041 0.836767 0.216057 0.101 Uiso 1 1 calc R U . . .
C20 C 0.5556(3) 0.7948(2) 0.01789(17) 0.0878(7) Uani 1 1 d . . . . .
H20A H 0.578558 0.741387 -0.033682 0.132 Uiso 1 1 calc R U . . .
H20B H 0.618080 0.868346 -0.002137 0.132 Uiso 1 1 calc R U . . .
H20C H 0.466231 0.830289 0.011828 0.132 Uiso 1 1 calc R U . . .
C21 C 0.70228(17) 0.6442(2) 0.15012(18) 0.0723(5) Uani 1 1 d . . . . .
H21A H 0.720580 0.587692 0.100733 0.108 Uiso 1 1 calc R U . . .
H21B H 0.706173 0.590730 0.228379 0.108 Uiso 1 1 calc R U . . .
H21C H 0.768119 0.715175 0.127099 0.108 Uiso 1 1 calc R U . . .
C22 C 0.36019(13) 0.37020(13) 0.31181(11) 0.0370(3) Uani 1 1 d . . . . .
C23 C 0.46385(14) 0.25552(13) 0.32607(12) 0.0398(3) Uani 1 1 d . . . . .
C24 C 0.50156(18) 0.22247(16) 0.44768(14) 0.0550(4) Uani 1 1 d . . . . .
H24A H 0.571436 0.155271 0.456867 0.082 Uiso 1 1 calc R U . . .
H24B H 0.423986 0.188331 0.503910 0.082 Uiso 1 1 calc R U . . .
H24C H 0.532808 0.303168 0.458208 0.082 Uiso 1 1 calc R U . . .
C25 C 0.40069(19) 0.12990(15) 0.31585(16) 0.0596(4) Uani 1 1 d . . . . .
H25A H 0.370469 0.150920 0.242324 0.089 Uiso 1 1 calc R U . . .
H25B H 0.325583 0.101176 0.376127 0.089 Uiso 1 1 calc R U . . .
H25C H 0.466236 0.058510 0.322681 0.089 Uiso 1 1 calc R U . . .
C26 C 0.59069(16) 0.29567(16) 0.23697(15) 0.0570(4) Uani 1 1 d . . . . .
H26A H 0.566799 0.321382 0.160844 0.085 Uiso 1 1 calc R U . . .
H26B H 0.651588 0.220166 0.246300 0.085 Uiso 1 1 calc R U . . .
H26C H 0.633290 0.370653 0.247844 0.085 Uiso 1 1 calc R U . . .
C27 C 0.10721(16) 0.65987(16) 0.60602(13) 0.0498(4) Uani 1 1 d . . . . .
H27A H 0.137043 0.743472 0.612259 0.075 Uiso 1 1 calc R U . . .
H27B H 0.138665 0.585250 0.664281 0.075 Uiso 1 1 calc R U . . .
H27C H 0.010704 0.658675 0.616265 0.075 Uiso 1 1 calc R U . . .
O1 O 0.32606(10) 0.48972(10) 0.54328(8) 0.0438(2) Uani 1 1 d . . . . .
O2 O -0.18834(15) 1.02113(14) 0.35357(15) 0.0921(5) Uani 1 1 d . . . . .
O3 O 0.42682(11) 0.55203(11) 0.09563(9) 0.0523(3) Uani 1 1 d . . . . .
O4 O 0.24228(10) 0.34878(11) 0.31610(11) 0.0597(3) Uani 1 1 d . . . . .
N1 N 0.16058(11) 0.64806(11) 0.49267(9) 0.0387(3) Uani 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
C1 N1 1.4556(17) . ?
C1 C9 1.4974(18) . ?
C1 C5 1.5033(17) . ?
C1 C2 1.5410(18) . ?
C2 C3 1.3396(18) . ?
C2 C10 1.4813(19) . ?
C3 C4 1.4902(18) . ?
C3 C16 1.5065(17) . ?
C4 O1 1.2225(15) . ?
C4 N1 1.3574(16) . ?
C5 C6 1.318(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.462(2) . ?
C6 H6 0.9300 . ?
C7 O2 1.2206(18) . ?
C7 C8 1.471(2) . ?
C8 C9 1.319(2) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C15 1.388(2) . ?
C10 C11 1.391(2) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.5428(17) . ?
C16 C22 1.5496(17) . ?
C16 H16 0.9800 . ?
C17 O3 1.2031(16) . ?
C17 C18 1.5398(19) . ?
C18 C20 1.519(2) . ?
C18 C19 1.527(2) . ?
C18 C21 1.535(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 O4 1.2085(16) . ?
C22 C23 1.5301(18) . ?
C23 C25 1.5247(19) . ?
C23 C26 1.530(2) . ?
C23 C24 1.537(2) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 N1 1.4555(17) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
N1 C1 C9 111.02(11) . . ?
N1 C1 C5 109.23(11) . . ?
C9 C1 C5 112.65(11) . . ?
N1 C1 C2 101.95(10) . . ?
C9 C1 C2 110.30(11) . . ?
C5 C1 C2 111.20(11) . . ?
C3 C2 C10 130.87(12) . . ?
C3 C2 C1 109.21(11) . . ?
C10 C2 C1 119.72(11) . . ?
C2 C3 C4 109.23(11) . . ?
C2 C3 C16 133.25(12) . . ?
C4 C3 C16 117.52(11) . . ?
O1 C4 N1 126.06(12) . . ?
O1 C4 C3 126.94(12) . . ?
N1 C4 C3 106.99(11) . . ?
C6 C5 C1 123.55(13) . . ?
C6 C5 H5 118.2 . . ?
C1 C5 H5 118.2 . . ?
C5 C6 C7 121.79(13) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
O2 C7 C6 121.76(16) . . ?
O2 C7 C8 121.48(16) . . ?
C6 C7 C8 116.75(13) . . ?
C9 C8 C7 121.46(14) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C1 123.79(13) . . ?
C8 C9 H9 118.1 . . ?
C1 C9 H9 118.1 . . ?
C15 C10 C11 118.69(16) . . ?
C15 C10 C2 119.29(13) . . ?
C11 C10 C2 121.99(15) . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.44(18) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C3 C16 C17 111.94(10) . . ?
C3 C16 C22 109.85(10) . . ?
C17 C16 C22 110.69(10) . . ?
C3 C16 H16 108.1 . . ?
C17 C16 H16 108.1 . . ?
C22 C16 H16 108.1 . . ?
O3 C17 C18 120.99(12) . . ?
O3 C17 C16 119.35(12) . . ?
C18 C17 C16 119.65(11) . . ?
C20 C18 C19 110.02(15) . . ?
C20 C18 C21 109.88(15) . . ?
C19 C18 C21 107.54(15) . . ?
C20 C18 C17 108.36(13) . . ?
C19 C18 C17 113.61(12) . . ?
C21 C18 C17 107.37(12) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C22 C23 121.38(12) . . ?
O4 C22 C16 119.27(12) . . ?
C23 C22 C16 119.29(11) . . ?
C25 C23 C22 109.28(12) . . ?
C25 C23 C26 110.14(13) . . ?
C22 C23 C26 111.79(11) . . ?
C25 C23 C24 108.47(12) . . ?
C22 C23 C24 107.82(11) . . ?
C26 C23 C24 109.25(13) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N1 C27 H27A 109.5 . . ?
N1 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N1 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C4 N1 C1 112.48(10) . . ?
C4 N1 C27 124.60(12) . . ?
C1 N1 C27 122.75(11) . . ?

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
N1 C1 C2 C3 -3.79(13) . . . . ?
C9 C1 C2 C3 -121.77(12) . . . . ?
C5 C1 C2 C3 112.51(13) . . . . ?
N1 C1 C2 C10 171.58(11) . . . . ?
C9 C1 C2 C10 53.61(15) . . . . ?
C5 C1 C2 C10 -72.12(16) . . . . ?
C10 C2 C3 C4 -171.55(13) . . . . ?
C1 C2 C3 C4 3.14(13) . . . . ?
C10 C2 C3 C16 7.6(2) . . . . ?
C1 C2 C3 C16 -177.66(12) . . . . ?
C2 C3 C4 O1 177.52(12) . . . . ?
C16 C3 C4 O1 -1.82(18) . . . . ?
C2 C3 C4 N1 -1.19(14) . . . . ?
C16 C3 C4 N1 179.47(10) . . . . ?
N1 C1 C5 C6 -123.90(16) . . . . ?
C9 C1 C5 C6 0.0(2) . . . . ?
C2 C1 C5 C6 124.36(16) . . . . ?
C1 C5 C6 C7 -0.6(3) . . . . ?
C5 C6 C7 O2 179.21(18) . . . . ?
C5 C6 C7 C8 0.4(2) . . . . ?
O2 C7 C8 C9 -178.31(17) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
C7 C8 C9 C1 -1.2(2) . . . . ?
N1 C1 C9 C8 123.83(15) . . . . ?
C5 C1 C9 C8 1.0(2) . . . . ?
C2 C1 C9 C8 -123.93(15) . . . . ?
C3 C2 C10 C15 58.5(2) . . . . ?
C1 C2 C10 C15 -115.74(15) . . . . ?
C3 C2 C10 C11 -123.39(17) . . . . ?
C1 C2 C10 C11 62.39(19) . . . . ?
C15 C10 C11 C12 -0.9(3) . . . . ?
C2 C10 C11 C12 -179.02(16) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C10 -0.1(3) . . . . ?
C11 C10 C15 C14 0.6(3) . . . . ?
C2 C10 C15 C14 178.82(16) . . . . ?
C2 C3 C16 C17 25.24(19) . . . . ?
C4 C3 C16 C17 -155.62(11) . . . . ?
C2 C3 C16 C22 -98.16(16) . . . . ?
C4 C3 C16 C22 80.98(13) . . . . ?
C3 C16 C17 O3 -99.98(14) . . . . ?
C22 C16 C17 O3 22.94(17) . . . . ?
C3 C16 C17 C18 81.39(14) . . . . ?
C22 C16 C17 C18 -155.69(11) . . . . ?
O3 C17 C18 C20 24.0(2) . . . . ?
C16 C17 C18 C20 -157.41(15) . . . . ?
O3 C17 C18 C19 146.58(15) . . . . ?
C16 C17 C18 C19 -34.81(18) . . . . ?
O3 C17 C18 C21 -94.65(17) . . . . ?
C16 C17 C18 C21 83.96(15) . . . . ?
C3 C16 C22 O4 25.83(17) . . . . ?
C17 C16 C22 O4 -98.30(15) . . . . ?
C3 C16 C22 C23 -151.24(11) . . . . ?
C17 C16 C22 C23 84.63(14) . . . . ?
O4 C22 C23 C25 13.54(19) . . . . ?
C16 C22 C23 C25 -169.45(12) . . . . ?
O4 C22 C23 C26 135.73(15) . . . . ?
C16 C22 C23 C26 -47.26(17) . . . . ?
O4 C22 C23 C24 -104.17(16) . . . . ?
C16 C22 C23 C24 72.85(15) . . . . ?
O1 C4 N1 C1 179.84(12) . . . . ?
C3 C4 N1 C1 -1.43(13) . . . . ?
O1 C4 N1 C27 4.4(2) . . . . ?
C3 C4 N1 C27 -176.85(12) . . . . ?
C9 C1 N1 C4 120.57(12) . . . . ?
C5 C1 N1 C4 -114.62(12) . . . . ?
C2 C1 N1 C4 3.11(13) . . . . ?
C9 C1 N1 C27 -63.92(16) . . . . ?
C5 C1 N1 C27 60.89(16) . . . . ?
C2 C1 N1 C27 178.62(12) . . . . ?

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_KB449_0m
_database_code_depnum_ccdc_archive 'CCDC 2171886'
loop_
_audit_author_name
_audit_author_address
'Balasubramanian Sridhar'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-05-10 deposited with the CCDC.	2022-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 O4'
_chemical_formula_sum            'C26 H20 O4'
_chemical_formula_weight         396.42

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   18.8869(12)
_cell_length_b                   12.5379(18)
_cell_length_c                   9.037(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.986(5)
_cell_angle_gamma                90
_cell_volume                     2107.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6573
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      25.57

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6636
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25169
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.095
_diffrn_reflns_theta_max         30.509
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6186
_reflns_number_gt                3325
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0671P)²+0.5616P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6186
_refine_ls_number_parameters     277
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1743
_refine_ls_wR_factor_gt          0.1381
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.023
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.36585(9) 0.62288(13) 0.94712(19) 0.0407(4) Uani 1 1 d . . . . .
C2 C 0.37948(9) 0.56975(13) 0.8196(2) 0.0417(4) Uani 1 1 d . . . . .
C3 C 0.44971(10) 0.56920(17) 0.7901(2) 0.0556(5) Uani 1 1 d . . . . .
H3 H 0.459879 0.533616 0.705952 0.067 Uiso 1 1 calc R U . . .
C4 C 0.50403(11) 0.62094(18) 0.8847(3) 0.0653(6) Uani 1 1 d . . . . .
H4 H 0.550498 0.619855 0.863565 0.078 Uiso 1 1 calc R U . . .
C5 C 0.49041(11) 0.67430(17) 1.0102(3) 0.0627(6) Uani 1 1 d . . . . .
H5 H 0.527285 0.709766 1.072673 0.075 Uiso 1 1 calc R U . . .
C6 C 0.42184(10) 0.67461(15) 1.0422(2) 0.0529(5) Uani 1 1 d . . . . .
H6 H 0.412567 0.709433 1.127709 0.063 Uiso 1 1 calc R U . . .
C7 C 0.29249(9) 0.62682(13) 0.98329(19) 0.0397(4) Uani 1 1 d . . . . .
C8 C 0.23380(8) 0.57345(12) 0.87985(18) 0.0354(4) Uani 1 1 d . . . . .
C9 C 0.24570(9) 0.52183(12) 0.75542(18) 0.0369(4) Uani 1 1 d . . . . .
C10 C 0.31998(9) 0.51404(13) 0.70991(18) 0.0378(4) Uani 1 1 d . . . . .
C11 C 0.33758(9) 0.39668(14) 0.7050(2) 0.0460(4) Uani 1 1 d . . . . .
H11 H 0.339677 0.357121 0.792724 0.055 Uiso 1 1 calc R U . . .
C12 C 0.35018(10) 0.34700(15) 0.5831(2) 0.0558(5) Uani 1 1 d . . . . .
H12 H 0.360128 0.274316 0.588274 0.067 Uiso 1 1 calc R U . . .
C13 C 0.34900(11) 0.40230(18) 0.4409(2) 0.0583(5) Uani 1 1 d . . . . .
C14 C 0.33234(10) 0.51620(16) 0.4384(2) 0.0530(5) Uani 1 1 d . . . . .
H14 H 0.332090 0.554522 0.350182 0.064 Uiso 1 1 calc R U . . .
C15 C 0.31756(10) 0.56636(14) 0.55886(19) 0.0450(4) Uani 1 1 d . . . . .
H15 H 0.304960 0.638061 0.549495 0.054 Uiso 1 1 calc R U . . .
C16 C 0.18497(9) 0.46499(15) 0.65806(19) 0.0443(4) Uani 1 1 d . . . . .
C17 C 0.15865(12) 0.37037(17) 0.7073(3) 0.0648(6) Uani 1 1 d . . . . .
H17 H 0.181179 0.340273 0.797320 0.078 Uiso 1 1 calc R U . . .
C18 C 0.09960(14) 0.3203(2) 0.6249(3) 0.0835(8) Uani 1 1 d . . . . .
H18 H 0.081900 0.257975 0.660656 0.100 Uiso 1 1 calc R U . . .
C19 C 0.06725(14) 0.3623(3) 0.4911(3) 0.0886(9) Uani 1 1 d . . . . .
H19 H 0.027987 0.327808 0.434719 0.106 Uiso 1 1 calc R U . . .
C20 C 0.09234(13) 0.4549(3) 0.4394(3) 0.0873(9) Uani 1 1 d . . . . .
H20 H 0.069897 0.483488 0.348350 0.105 Uiso 1 1 calc R U . . .
C21 C 0.15157(11) 0.5068(2) 0.5229(2) 0.0653(6) Uani 1 1 d . . . . .
H21 H 0.168489 0.569695 0.487119 0.078 Uiso 1 1 calc R U . . .
C22 C 0.16079(8) 0.57879(14) 0.92045(18) 0.0388(4) Uani 1 1 d . . . . .
C23 C 0.11107(10) 0.65399(15) 0.8540(2) 0.0476(4) Uani 1 1 d . . . . .
C24 C 0.12792(13) 0.73799(18) 0.7495(3) 0.0717(6) Uani 1 1 d . . . . .
H24A H 0.113157 0.714510 0.647719 0.108 Uiso 1 1 calc R U . . .
H24B H 0.178734 0.751394 0.767684 0.108 Uiso 1 1 calc R U . . .
H24C H 0.102761 0.802333 0.765555 0.108 Uiso 1 1 calc R U . . .
C25 C 0.14181(10) 0.50852(16) 1.0294(2) 0.0516(5) Uani 1 1 d . . . . .
C26 C 0.19485(13) 0.4330(2) 1.1157(3) 0.0740(7) Uani 1 1 d . . . . .
H26A H 0.186166 0.362321 1.075813 0.111 Uiso 1 1 calc R U . . .
H26B H 0.189722 0.433529 1.219499 0.111 Uiso 1 1 calc R U . . .
H26C H 0.242714 0.454709 1.107058 0.111 Uiso 1 1 calc R U . . .
O1 O 0.28042(7) 0.67277(11) 1.09602(15) 0.0590(4) Uani 1 1 d . . . . .
O2 O 0.36189(10) 0.35592(15) 0.32887(19) 0.0909(6) Uani 1 1 d . . . . .
O3 O 0.07837(8) 0.50693(15) 1.05966(17) 0.0793(5) Uani 1 1 d . . . . .
O4 O 0.04580(8) 0.65649(14) 0.88128(18) 0.0697(4) Uani 1 1 d D . . . .
H4O H 0.045(2) 0.603(2) 0.958(3) 0.150(14) 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
C1 C2 1.393(2) . ?
C1 C6 1.401(2) . ?
C1 C7 1.479(2) . ?
C2 C3 1.398(2) . ?
C2 C10 1.532(2) . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.226(2) . ?
C7 C8 1.480(2) . ?
C8 C9 1.350(2) . ?
C8 C22 1.489(2) . ?
C9 C16 1.499(2) . ?
C9 C10 1.532(2) . ?
C10 C15 1.508(2) . ?
C10 C11 1.511(2) . ?
C11 C12 1.323(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.457(3) . ?
C12 H12 0.9300 . ?
C13 O2 1.228(2) . ?
C13 C14 1.462(3) . ?
C14 C15 1.328(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.378(3) . ?
C16 C17 1.389(3) . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.363(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.366(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.397(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.391(2) . ?
C22 C25 1.413(2) . ?
C23 O4 1.298(2) . ?
C23 C24 1.486(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O3 1.275(2) . ?
C25 C26 1.496(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
O4 H4O 0.966(18) . ?

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
C2 C1 C6 120.05(16) . . ?
C2 C1 C7 120.90(15) . . ?
C6 C1 C7 119.05(16) . . ?
C1 C2 C3 118.55(16) . . ?
C1 C2 C10 122.22(15) . . ?
C3 C2 C10 119.22(16) . . ?
C4 C3 C2 120.55(19) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.90(19) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.42(18) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 120.52(19) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
O1 C7 C1 121.06(15) . . ?
O1 C7 C8 120.70(15) . . ?
C1 C7 C8 118.23(14) . . ?
C9 C8 C7 121.89(14) . . ?
C9 C8 C22 121.48(14) . . ?
C7 C8 C22 116.63(14) . . ?
C8 C9 C16 119.73(14) . . ?
C8 C9 C10 123.15(14) . . ?
C16 C9 C10 117.07(13) . . ?
C15 C10 C11 111.68(14) . . ?
C15 C10 C9 109.26(13) . . ?
C11 C10 C9 106.63(13) . . ?
C15 C10 C2 106.92(13) . . ?
C11 C10 C2 108.82(14) . . ?
C9 C10 C2 113.60(13) . . ?
C12 C11 C10 123.72(17) . . ?
C12 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C11 C12 C13 122.22(18) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
O2 C13 C12 121.8(2) . . ?
O2 C13 C14 121.5(2) . . ?
C12 C13 C14 116.69(16) . . ?
C15 C14 C13 121.68(18) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C10 123.94(17) . . ?
C14 C15 H15 118.0 . . ?
C10 C15 H15 118.0 . . ?
C21 C16 C17 118.34(19) . . ?
C21 C16 C9 121.72(18) . . ?
C17 C16 C9 119.85(17) . . ?
C18 C17 C16 121.1(2) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 120.3(2) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 120.2(2) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C25 119.30(16) . . ?
C23 C22 C8 120.60(15) . . ?
C25 C22 C8 120.10(15) . . ?
O4 C23 C22 121.78(17) . . ?
O4 C23 C24 114.74(17) . . ?
C22 C23 C24 123.48(17) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3 C25 C22 121.39(18) . . ?
O3 C25 C26 116.60(18) . . ?
C22 C25 C26 122.01(17) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 O4 H4O 105(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
C6 C1 C2 C3 0.3(3) . . . . ?
C7 C1 C2 C3 179.51(16) . . . . ?
C6 C1 C2 C10 -178.60(16) . . . . ?
C7 C1 C2 C10 0.6(2) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C10 C2 C3 C4 178.35(17) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C7 C1 C6 C5 -178.69(17) . . . . ?
C2 C1 C7 O1 179.42(16) . . . . ?
C6 C1 C7 O1 -1.3(2) . . . . ?
C2 C1 C7 C8 -0.4(2) . . . . ?
C6 C1 C7 C8 178.84(15) . . . . ?
O1 C7 C8 C9 -179.64(16) . . . . ?
C1 C7 C8 C9 0.2(2) . . . . ?
O1 C7 C8 C22 -0.1(2) . . . . ?
C1 C7 C8 C22 179.75(14) . . . . ?
C7 C8 C9 C16 177.31(15) . . . . ?
C22 C8 C9 C16 -2.2(2) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
C22 C8 C9 C10 -179.74(14) . . . . ?
C8 C9 C10 C15 -118.90(17) . . . . ?
C16 C9 C10 C15 63.53(18) . . . . ?
C8 C9 C10 C11 120.25(17) . . . . ?
C16 C9 C10 C11 -57.32(18) . . . . ?
C8 C9 C10 C2 0.4(2) . . . . ?
C16 C9 C10 C2 -177.18(14) . . . . ?
C1 C2 C10 C15 120.00(17) . . . . ?
C3 C2 C10 C15 -58.9(2) . . . . ?
C1 C2 C10 C11 -119.22(17) . . . . ?
C3 C2 C10 C11 61.9(2) . . . . ?
C1 C2 C10 C9 -0.6(2) . . . . ?
C3 C2 C10 C9 -179.47(15) . . . . ?
C15 C10 C11 C12 0.8(2) . . . . ?
C9 C10 C11 C12 120.14(18) . . . . ?
C2 C10 C11 C12 -116.96(19) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C11 C12 C13 O2 178.8(2) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
O2 C13 C14 C15 179.2(2) . . . . ?
C12 C13 C14 C15 -1.3(3) . . . . ?
C13 C14 C15 C10 3.2(3) . . . . ?
C11 C10 C15 C14 -2.9(2) . . . . ?
C9 C10 C15 C14 -120.59(19) . . . . ?
C2 C10 C15 C14 116.08(19) . . . . ?
C8 C9 C16 C21 104.0(2) . . . . ?
C10 C9 C16 C21 -78.3(2) . . . . ?
C8 C9 C16 C17 -72.6(2) . . . . ?
C10 C9 C16 C17 105.04(19) . . . . ?
C21 C16 C17 C18 -1.3(3) . . . . ?
C9 C16 C17 C18 175.4(2) . . . . ?
C16 C17 C18 C19 1.6(4) . . . . ?
C17 C18 C19 C20 -1.2(4) . . . . ?
C18 C19 C20 C21 0.4(4) . . . . ?
C17 C16 C21 C20 0.6(3) . . . . ?
C9 C16 C21 C20 -176.10(19) . . . . ?
C19 C20 C21 C16 -0.1(4) . . . . ?
C9 C8 C22 C23 -82.0(2) . . . . ?
C7 C8 C22 C23 98.48(19) . . . . ?
C9 C8 C22 C25 99.3(2) . . . . ?
C7 C8 C22 C25 -80.3(2) . . . . ?
C25 C22 C23 O4 -5.1(3) . . . . ?
C8 C22 C23 O4 176.13(16) . . . . ?
C25 C22 C23 C24 173.98(18) . . . . ?
C8 C22 C23 C24 -4.8(3) . . . . ?
C23 C22 C25 O3 5.5(3) . . . . ?
C8 C22 C25 O3 -175.67(17) . . . . ?
C23 C22 C25 C26 -174.02(19) . . . . ?
C8 C22 C25 C26 4.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4O O3 0.966(18) 1.58(2) 2.480(2) 153(3) . yes

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_KB486_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2171887'
loop_
_audit_author_name
_audit_author_address
'Balasubramanian Sridhar'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-05-10 deposited with the CCDC.	2022-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 N O4'
_chemical_formula_sum            'C21 H19 N O4'
_chemical_formula_weight         349.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.7602(18)
_cell_length_b                   10.600(2)
_cell_length_c                   10.571(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.369(6)
_cell_angle_gamma                90
_cell_volume                     914.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6250
_cell_measurement_theta_min      2.4965
_cell_measurement_theta_max      22.688

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4235
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18725
_diffrn_reflns_av_unetI/netI     0.0853
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.497
_diffrn_reflns_theta_max         30.593
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5491
_reflns_number_gt                2933
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_max     0.962
_reflns_Friedel_fraction_full    0.995

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0729P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1073 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5491
_refine_ls_number_parameters     242
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1511
_refine_ls_wR_factor_gt          0.1244
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.987
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8738(4) 0.2937(3) 0.9966(3) 0.0600(8) Uani 1 1 d . . . . .
C2 C 0.8706(4) 0.4305(3) 1.0019(3) 0.0599(8) Uani 1 1 d . . . . .
H2 H 0.925966 0.471253 1.083699 0.072 Uiso 1 1 calc R U . . .
C3 C 0.7908(4) 0.4980(3) 0.8932(3) 0.0542(7) Uani 1 1 d . . . . .
H3 H 0.799514 0.585429 0.899817 0.065 Uiso 1 1 calc R U . . .
C4 C 0.6870(3) 0.4418(3) 0.7599(2) 0.0448(7) Uani 1 1 d . . . . .
C5 C 0.7084(4) 0.3011(3) 0.7564(3) 0.0527(7) Uani 1 1 d . . . . .
H5 H 0.660664 0.259409 0.673869 0.063 Uiso 1 1 calc R U . . .
C6 C 0.7913(4) 0.2346(3) 0.8645(3) 0.0589(8) Uani 1 1 d . . . . .
H6 H 0.797667 0.147502 0.856625 0.071 Uiso 1 1 calc R U . . .
C7 C 0.5052(3) 0.4695(3) 0.7259(2) 0.0455(6) Uani 1 1 d . . . . .
C8 C 0.4434(3) 0.5315(3) 0.6084(2) 0.0472(7) Uani 1 1 d . . . . .
C9 C 0.5794(4) 0.5539(3) 0.5566(3) 0.0530(8) Uani 1 1 d . . . . .
C10 C 0.8774(4) 0.5091(4) 0.6379(4) 0.0664(8) Uani 1 1 d . . . . .
H10A H 0.868075 0.542846 0.551091 0.100 Uiso 1 1 calc R U . . .
H10B H 0.923426 0.425827 0.647797 0.100 Uiso 1 1 calc R U . . .
H10C H 0.947277 0.562456 0.708689 0.100 Uiso 1 1 calc R U . . .
C11 C 0.4212(3) 0.4250(3) 0.8166(3) 0.0512(7) Uani 1 1 d . . . . .
C12 C 0.4484(5) 0.4864(4) 0.9401(4) 0.0747(10) Uani 1 1 d . . . . .
H12 H 0.515093 0.557555 0.962389 0.090 Uiso 1 1 calc R U . . .
C13 C 0.3781(6) 0.4435(4) 1.0293(4) 0.0829(12) Uani 1 1 d . . . . .
H13 H 0.399724 0.483324 1.112407 0.100 Uiso 1 1 calc R U . . .
C14 C 0.2759(5) 0.3412(5) 0.9937(5) 0.0897(14) Uani 1 1 d . . . . .
H14 H 0.224233 0.313800 1.051491 0.108 Uiso 1 1 calc R U . . .
C15 C 0.2486(5) 0.2786(5) 0.8739(5) 0.0976(15) Uani 1 1 d . . . . .
H15 H 0.180353 0.208346 0.851687 0.117 Uiso 1 1 calc R U . . .
C16 C 0.3229(5) 0.3202(4) 0.7860(3) 0.0801(12) Uani 1 1 d . . . . .
H16 H 0.305967 0.276606 0.705687 0.096 Uiso 1 1 calc R U . . .
C17 C 0.2740(4) 0.5743(3) 0.5323(3) 0.0511(7) Uani 1 1 d . . . . .
C18 C 0.2125(4) 0.6848(3) 0.5668(3) 0.0586(8) Uani 1 1 d . . . . .
C19 C 0.1748(4) 0.5038(4) 0.4172(3) 0.0602(8) Uani 1 1 d . . . . .
C20 C 0.2342(5) 0.3863(4) 0.3761(3) 0.0818(11) Uani 1 1 d . . . . .
H20A H 0.142936 0.339909 0.315096 0.123 Uiso 1 1 calc R U . . .
H20B H 0.289583 0.336020 0.455139 0.123 Uiso 1 1 calc R U . . .
H20C H 0.308860 0.406468 0.331415 0.123 Uiso 1 1 calc R U . . .
C21 C 0.3050(6) 0.7671(4) 0.6811(4) 0.0882(12) Uani 1 1 d . . . . .
H21A H 0.265046 0.851960 0.661947 0.132 Uiso 1 1 calc R U . . .
H21B H 0.419122 0.764816 0.693706 0.132 Uiso 1 1 calc R U . . .
H21C H 0.291045 0.738111 0.762302 0.132 Uiso 1 1 calc R U . . .
N1 N 0.7160(3) 0.5032(3) 0.6469(2) 0.0543(6) Uani 1 1 d . . . . .
O1 O 0.9460(4) 0.2314(3) 1.0983(3) 0.0979(9) Uani 1 1 d . . . . .
O2 O 0.5678(3) 0.6081(3) 0.4513(2) 0.0769(8) Uani 1 1 d . . . . .
O3 O 0.0648(3) 0.7232(3) 0.4957(3) 0.0747(7) Uani 1 1 d D . . . .
H3O H 0.039(6) 0.658(4) 0.424(4) 0.123(18) Uiso 1 1 d D . . . .
O4 O 0.0304(3) 0.5413(3) 0.3458(2) 0.0781(8) Uani 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
C1 O1 1.223(4) . ?
C1 C2 1.451(5) . ?
C1 C6 1.459(4) . ?
C2 C3 1.317(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.495(4) . ?
C3 H3 0.9300 . ?
C4 N1 1.461(4) . ?
C4 C5 1.505(4) . ?
C4 C7 1.528(4) . ?
C5 C6 1.314(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.333(4) . ?
C7 C11 1.483(4) . ?
C8 C17 1.478(4) . ?
C8 C9 1.501(4) . ?
C9 O2 1.223(3) . ?
C9 N1 1.342(4) . ?
C10 N1 1.452(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C16 1.370(5) . ?
C11 C12 1.399(4) . ?
C12 C13 1.378(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.392(5) . ?
C17 C19 1.422(4) . ?
C18 O3 1.303(4) . ?
C18 C21 1.471(5) . ?
C19 O4 1.277(4) . ?
C19 C20 1.475(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
O3 H3O 0.98(3) . ?

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
O1 C1 C2 121.1(3) . . ?
O1 C1 C6 121.7(3) . . ?
C2 C1 C6 117.1(3) . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 123.5(3) . . ?
C2 C3 H3 118.2 . . ?
C4 C3 H3 118.2 . . ?
N1 C4 C3 111.4(2) . . ?
N1 C4 C5 111.1(2) . . ?
C3 C4 C5 112.4(2) . . ?
N1 C4 C7 101.5(2) . . ?
C3 C4 C7 111.7(2) . . ?
C5 C4 C7 108.2(2) . . ?
C6 C5 C4 123.0(2) . . ?
C6 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C5 C6 C1 121.7(3) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
C8 C7 C11 129.1(3) . . ?
C8 C7 C4 110.4(2) . . ?
C11 C7 C4 120.5(2) . . ?
C7 C8 C17 130.1(3) . . ?
C7 C8 C9 108.1(2) . . ?
C17 C8 C9 121.7(2) . . ?
O2 C9 N1 126.4(3) . . ?
O2 C9 C8 126.3(3) . . ?
N1 C9 C8 107.3(2) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 118.4(3) . . ?
C16 C11 C7 121.5(3) . . ?
C12 C11 C7 120.0(3) . . ?
C13 C12 C11 121.2(4) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C14 C13 C12 119.0(4) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 121.0(4) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C16 119.9(4) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 120.5(4) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C19 119.5(3) . . ?
C18 C17 C8 121.5(3) . . ?
C19 C17 C8 118.9(3) . . ?
O3 C18 C17 120.6(3) . . ?
O3 C18 C21 115.0(3) . . ?
C17 C18 C21 124.3(3) . . ?
O4 C19 C17 120.5(3) . . ?
O4 C19 C20 117.9(3) . . ?
C17 C19 C20 121.6(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C9 N1 C10 124.9(3) . . ?
C9 N1 C4 112.6(2) . . ?
C10 N1 C4 122.5(2) . . ?
C18 O3 H3O 97(3) . . ?

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 -178.9(3) . . . . ?
C6 C1 C2 C3 2.8(5) . . . . ?
C1 C2 C3 C4 5.1(5) . . . . ?
C2 C3 C4 N1 -135.9(3) . . . . ?
C2 C3 C4 C5 -10.5(4) . . . . ?
C2 C3 C4 C7 111.4(3) . . . . ?
N1 C4 C5 C6 134.4(3) . . . . ?
C3 C4 C5 C6 8.8(4) . . . . ?
C7 C4 C5 C6 -115.0(3) . . . . ?
C4 C5 C6 C1 -1.9(5) . . . . ?
O1 C1 C6 C5 177.3(3) . . . . ?
C2 C1 C6 C5 -4.4(5) . . . . ?
N1 C4 C7 C8 2.6(3) . . . . ?
C3 C4 C7 C8 121.4(3) . . . . ?
C5 C4 C7 C8 -114.4(3) . . . . ?
N1 C4 C7 C11 -179.2(2) . . . . ?
C3 C4 C7 C11 -60.4(3) . . . . ?
C5 C4 C7 C11 63.8(3) . . . . ?
C11 C7 C8 C17 -0.4(5) . . . . ?
C4 C7 C8 C17 177.6(3) . . . . ?
C11 C7 C8 C9 -179.8(3) . . . . ?
C4 C7 C8 C9 -1.7(3) . . . . ?
C7 C8 C9 O2 179.9(3) . . . . ?
C17 C8 C9 O2 0.5(5) . . . . ?
C7 C8 C9 N1 0.1(3) . . . . ?
C17 C8 C9 N1 -179.3(3) . . . . ?
C8 C7 C11 C16 76.3(4) . . . . ?
C4 C7 C11 C16 -101.5(4) . . . . ?
C8 C7 C11 C12 -107.1(4) . . . . ?
C4 C7 C11 C12 75.1(4) . . . . ?
C16 C11 C12 C13 -0.2(5) . . . . ?
C7 C11 C12 C13 -176.9(3) . . . . ?
C11 C12 C13 C14 -2.1(6) . . . . ?
C12 C13 C14 C15 2.7(6) . . . . ?
C13 C14 C15 C16 -1.1(7) . . . . ?
C12 C11 C16 C15 1.9(5) . . . . ?
C7 C11 C16 C15 178.5(4) . . . . ?
C14 C15 C16 C11 -1.3(7) . . . . ?
C7 C8 C17 C18 81.0(4) . . . . ?
C9 C8 C17 C18 -99.7(3) . . . . ?
C7 C8 C17 C19 -102.1(4) . . . . ?
C9 C8 C17 C19 77.2(4) . . . . ?
C19 C17 C18 O3 0.7(5) . . . . ?
C8 C17 C18 O3 177.6(3) . . . . ?
C19 C17 C18 C21 -178.3(3) . . . . ?
C8 C17 C18 C21 -1.4(5) . . . . ?
C18 C17 C19 O4 0.0(5) . . . . ?
C8 C17 C19 O4 -176.9(3) . . . . ?
C18 C17 C19 C20 179.9(3) . . . . ?
C8 C17 C19 C20 2.9(5) . . . . ?
O2 C9 N1 C10 3.0(5) . . . . ?
C8 C9 N1 C10 -177.2(3) . . . . ?
O2 C9 N1 C4 -178.2(3) . . . . ?
C8 C9 N1 C4 1.6(3) . . . . ?
C3 C4 N1 C9 -121.5(3) . . . . ?
C5 C4 N1 C9 112.4(3) . . . . ?
C7 C4 N1 C9 -2.5(3) . . . . ?
C3 C4 N1 C10 57.4(4) . . . . ?
C5 C4 N1 C10 -68.8(4) . . . . ?
C7 C4 N1 C10 176.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3O O4 0.98(3) 1.48(3) 2.444(4) 165(5) . yes

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.048

