# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_dead
_database_code_depnum_ccdc_archive 'CCDC 2017969'
loop_
_audit_author_name
_audit_author_address
'V. Ramkumar '
;Department of Chemistry, IIT Madras, Chennai 
India
;
_audit_update_record             
;
2020-07-21 deposited with the CCDC.	2020-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H32 O8'
_chemical_formula_sum            'C28 H32 O8'
_chemical_formula_weight         496.53

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

_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_H-M_alt        'I -4'
_space_group_name_Hall           'I -4'

_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'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'

_cell_length_a                   31.5358(10)
_cell_length_b                   31.5358(10)
_cell_length_c                   5.2684(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5239.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4535
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      21.58

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             2112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14835
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         0.913
_diffrn_reflns_theta_max         24.785
_diffrn_reflns_theta_full        24.785
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.934
_reflns_number_total             4221
_reflns_number_gt                2393
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_max     0.924
_reflns_Friedel_fraction_full    0.924

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1025P)²] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0013(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 806 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.6(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4221
_refine_ls_number_parameters     330
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1715
_refine_ls_wR_factor_gt          0.1360
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_restrained_S_all      0.940
_refine_ls_shift/su_max          0.055
_refine_ls_shift/su_mean         0.005

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 0.4415(3) 0.2960(3) 0.903(2) 0.138(4) Uani 1 1 d . . . . .
H1A H 0.4221 0.2784 0.8108 0.207 Uiso 1 1 calc R U . . .
H1B H 0.4497 0.2821 1.0572 0.207 Uiso 1 1 calc R U . . .
H1C H 0.4662 0.3011 0.8007 0.207 Uiso 1 1 calc R U . . .
C2 C 0.4217(3) 0.3352(3) 0.9611(17) 0.111(3) Uani 1 1 d . . . . .
H2A H 0.4424 0.3580 0.9574 0.133 Uiso 1 1 calc R U . . .
H2B H 0.4093 0.3341 1.1295 0.133 Uiso 1 1 calc R U . . .
C3 C 0.37515(17) 0.3823(2) 0.7440(11) 0.0637(14) Uani 1 1 d . . . . .
C4 C 0.34344(15) 0.38527(16) 0.5370(10) 0.0569(13) Uani 1 1 d . . . . .
C5 C 0.32326(17) 0.34555(17) 0.4432(12) 0.0636(14) Uani 1 1 d . . . . .
H5A H 0.3095 0.3316 0.5852 0.076 Uiso 1 1 calc R U . . .
H5B H 0.3454 0.3267 0.3827 0.076 Uiso 1 1 calc R U . . .
C6 C 0.29126(16) 0.35111(16) 0.2349(10) 0.0588(13) Uani 1 1 d . . . . .
C7 C 0.27422(19) 0.31096(18) 0.1315(12) 0.0667(15) Uani 1 1 d . . . . .
H7 H 0.2938 0.2924 0.0601 0.080 Uiso 1 1 calc R U . . .
C8 C 0.2345(2) 0.29881(17) 0.1300(12) 0.0689(15) Uani 1 1 d . . . . .
H8 H 0.2286 0.2725 0.0579 0.083 Uiso 1 1 calc R U . . .
C9 C 0.19815(16) 0.32291(17) 0.2319(12) 0.0646(15) Uani 1 1 d . . . . .
C10 C 0.17389(19) 0.29997(18) 0.4339(13) 0.0729(16) Uani 1 1 d . . . . .
H10A H 0.1928 0.2949 0.5759 0.088 Uiso 1 1 calc R U . . .
H10B H 0.1654 0.2726 0.3675 0.088 Uiso 1 1 calc R U . . .
C11 C 0.13509(19) 0.32209(18) 0.5314(11) 0.0684(15) Uani 1 1 d . . . . .
C12 C 0.12414(18) 0.36074(19) 0.4492(11) 0.0657(14) Uani 1 1 d . . . . .
C13 C 0.14878(19) 0.38413(18) 0.2538(13) 0.0718(15) Uani 1 1 d . . . . .
H13A H 0.1584 0.4106 0.3273 0.086 Uiso 1 1 calc R U . . .
H13B H 0.1299 0.3911 0.1145 0.086 Uiso 1 1 calc R U . . .
C14 C 0.18671(18) 0.36094(18) 0.1479(11) 0.0628(14) Uani 1 1 d . . . . .
C15 C 0.2092(2) 0.38421(18) -0.0555(11) 0.0710(16) Uani 1 1 d . . . . .
H15 H 0.1933 0.3912 -0.1981 0.085 Uiso 1 1 calc R U . . .
C16 C 0.24900(19) 0.39609(18) -0.0575(11) 0.0643(14) Uani 1 1 d . . . . .
H16 H 0.2585 0.4103 -0.2015 0.077 Uiso 1 1 calc R U . . .
C17 C 0.28017(16) 0.38914(17) 0.1459(11) 0.0584(13) Uani 1 1 d . . . . .
C18 C 0.30028(17) 0.42921(17) 0.2413(11) 0.0626(13) Uani 1 1 d . . . . .
H18A H 0.3135 0.4436 0.0992 0.075 Uiso 1 1 calc R U . . .
H18B H 0.2781 0.4476 0.3061 0.075 Uiso 1 1 calc R U . . .
C19 C 0.33275(15) 0.42326(17) 0.4442(10) 0.0547(12) Uani 1 1 d . . . . .
C20 C 0.34949(19) 0.46422(18) 0.5464(11) 0.0639(15) Uani 1 1 d . . . . .
C21 C 0.4039(2) 0.5152(2) 0.5357(14) 0.0845(18) Uani 1 1 d . . . . .
H21A H 0.3808 0.5348 0.5685 0.101 Uiso 1 1 calc R U . . .
H21B H 0.4211 0.5270 0.4003 0.101 Uiso 1 1 calc R U . . .
C22 C 0.4297(2) 0.5111(2) 0.7644(15) 0.094(2) Uani 1 1 d . . . . .
H22A H 0.4127 0.4996 0.8993 0.141 Uiso 1 1 calc R U . . .
H22B H 0.4403 0.5384 0.8131 0.141 Uiso 1 1 calc R U . . .
H22C H 0.4531 0.4924 0.7311 0.141 Uiso 1 1 calc R U . . .
C23 C 0.0038(4) 0.3019(4) 0.935(3) 0.193(6) Uani 1 1 d . . . . .
H23A H -0.0001 0.3311 0.8884 0.290 Uiso 1 1 calc R U . . .
H23B H -0.0118 0.2960 1.0870 0.290 Uiso 1 1 calc R U . . .
H23C H -0.0063 0.2840 0.8000 0.290 Uiso 1 1 calc R U . . .
C24 C 0.0484(4) 0.2938(4) 0.978(2) 0.157(4) Uani 1 1 d . . . . .
H24A H 0.0535 0.2635 0.9788 0.188 Uiso 1 1 calc R U . . .
H24B H 0.0566 0.3051 1.1417 0.188 Uiso 1 1 calc R U . . .
C25 C 0.1118(2) 0.2988(2) 0.7319(14) 0.0859(19) Uani 1 1 d . . . . .
C26 C -0.0121(4) 0.4111(6) 0.295(3) 0.237(9) Uani 1 1 d D . . . .
H26A H 0.0044 0.4151 0.1436 0.356 Uiso 1 1 calc R U . . .
H26B H -0.0295 0.4356 0.3229 0.356 Uiso 1 1 calc R U . . .
H26C H -0.0297 0.3865 0.2757 0.356 Uiso 1 1 calc R U . . .
C27 C 0.0173(3) 0.4050(5) 0.519(2) 0.168(5) Uani 1 1 d D . . . .
H27A H 0.0262 0.4321 0.5875 0.202 Uiso 1 1 calc R U . . .
H27B H 0.0033 0.3890 0.6524 0.202 Uiso 1 1 calc R U . . .
C28 C 0.0881(2) 0.3853(2) 0.5522(13) 0.0790(18) Uani 1 1 d . . . . .
O1 O 0.38877(15) 0.34283(15) 0.7720(10) 0.0964(16) Uani 1 1 d . . . . .
O2 O 0.38787(15) 0.41113(15) 0.8671(8) 0.0844(12) Uani 1 1 d . . . . .
O3 O 0.12603(19) 0.2686(2) 0.8398(14) 0.131(2) Uani 1 1 d . . . . .
O4 O 0.0743(2) 0.3137(2) 0.7774(13) 0.124(2) Uani 1 1 d . . . . .
O5 O 0.32807(15) 0.48672(14) 0.6812(10) 0.0912(14) Uani 1 1 d . . . . .
O6 O 0.38664(13) 0.47476(13) 0.4547(8) 0.0728(11) Uani 1 1 d . . . . .
O7 O 0.0915(2) 0.4096(2) 0.7232(12) 0.126(2) Uani 1 1 d . . . . .
O8 O 0.05334(15) 0.3817(2) 0.4203(9) 0.1098(18) 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 C2 1.418(11) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.459(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O2 1.186(7) . ?
C3 O1 1.326(7) . ?
C3 C4 1.482(8) . ?
C4 C19 1.337(7) . ?
C4 C5 1.490(8) . ?
C5 C6 1.501(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C17 1.334(7) . ?
C6 C7 1.479(8) . ?
C7 C8 1.311(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.475(8) . ?
C8 H8 0.9300 . ?
C9 C14 1.328(8) . ?
C9 C10 1.497(9) . ?
C10 C11 1.499(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.339(8) . ?
C11 C25 1.482(10) . ?
C12 C28 1.479(9) . ?
C12 C13 1.486(9) . ?
C13 C14 1.509(9) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.480(9) . ?
C15 C16 1.310(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.471(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.501(8) . ?
C18 C19 1.492(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.496(8) . ?
C20 O5 1.210(7) . ?
C20 O6 1.310(7) . ?
C21 O6 1.452(7) . ?
C21 C22 1.460(10) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.447(16) . ?
C23 H23A 0.9676 . ?
C23 H23B 0.9675 . ?
C23 H23C 0.9676 . ?
C24 O4 1.474(11) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 O3 1.196(8) . ?
C25 O4 1.296(9) . ?
C26 C27 1.514(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 O8 1.450(10) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 O7 1.189(8) . ?
C28 O8 1.302(8) . ?

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 H1A 109.4 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 O1 108.0(7) . . ?
C1 C2 H2A 110.0 . . ?
O1 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
O1 C2 H2B 110.2 . . ?
H2A C2 H2B 108.4 . . ?
O2 C3 O1 123.3(5) . . ?
O2 C3 C4 125.7(5) . . ?
O1 C3 C4 111.0(5) . . ?
C19 C4 C3 119.7(5) . . ?
C19 C4 C5 121.6(5) . . ?
C3 C4 C5 118.7(5) . . ?
C4 C5 C6 115.6(4) . . ?
C4 C5 H5A 108.4 . . ?
C6 C5 H5A 108.4 . . ?
C4 C5 H5B 108.4 . . ?
C6 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C17 C6 C7 123.0(5) . . ?
C17 C6 C5 122.5(5) . . ?
C7 C6 C5 114.4(5) . . ?
C8 C7 C6 126.8(5) . . ?
C8 C7 H7 116.6 . . ?
C6 C7 H7 116.6 . . ?
C7 C8 C9 126.1(5) . . ?
C7 C8 H8 116.9 . . ?
C9 C8 H8 117.0 . . ?
C14 C9 C8 123.7(6) . . ?
C14 C9 C10 122.3(5) . . ?
C8 C9 C10 114.0(5) . . ?
C9 C10 C11 115.8(5) . . ?
C9 C10 H10A 108.3 . . ?
C11 C10 H10A 108.4 . . ?
C9 C10 H10B 108.3 . . ?
C11 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C12 C11 C25 123.7(6) . . ?
C12 C11 C10 121.5(5) . . ?
C25 C11 C10 114.7(5) . . ?
C11 C12 C28 123.8(6) . . ?
C11 C12 C13 122.8(5) . . ?
C28 C12 C13 113.3(5) . . ?
C12 C13 C14 115.5(5) . . ?
C12 C13 H13A 108.4 . . ?
C14 C13 H13A 108.4 . . ?
C12 C13 H13B 108.4 . . ?
C14 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C9 C14 C15 124.0(5) . . ?
C9 C14 C13 122.0(5) . . ?
C15 C14 C13 114.0(5) . . ?
C16 C15 C14 127.3(5) . . ?
C16 C15 H15 116.3 . . ?
C14 C15 H15 116.3 . . ?
C15 C16 C17 126.3(6) . . ?
C15 C16 H16 116.9 . . ?
C17 C16 H16 116.8 . . ?
C6 C17 C16 124.4(5) . . ?
C6 C17 C18 121.9(5) . . ?
C16 C17 C18 113.7(4) . . ?
C19 C18 C17 115.1(4) . . ?
C19 C18 H18A 108.5 . . ?
C17 C18 H18A 108.5 . . ?
C19 C18 H18B 108.5 . . ?
C17 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C4 C19 C18 123.2(5) . . ?
C4 C19 C20 123.6(5) . . ?
C18 C19 C20 113.0(4) . . ?
O5 C20 O6 124.5(5) . . ?
O5 C20 C19 121.4(5) . . ?
O6 C20 C19 113.7(5) . . ?
O6 C21 C22 111.8(6) . . ?
O6 C21 H21A 109.2 . . ?
C22 C21 H21A 109.2 . . ?
O6 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.4 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 H23A 110.2 . . ?
C24 C23 H23B 110.1 . . ?
H23A C23 H23B 108.7 . . ?
C24 C23 H23C 110.4 . . ?
H23A C23 H23C 108.7 . . ?
H23B C23 H23C 108.6 . . ?
C23 C24 O4 110.6(11) . . ?
C23 C24 H24A 109.5 . . ?
O4 C24 H24A 109.5 . . ?
C23 C24 H24B 109.7 . . ?
O4 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
O3 C25 O4 123.0(7) . . ?
O3 C25 C11 123.2(7) . . ?
O4 C25 C11 113.8(6) . . ?
C27 C26 H26A 109.4 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C27 C26 H26C 109.6 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O8 C27 C26 105.3(7) . . ?
O8 C27 H27A 110.7 . . ?
C26 C27 H27A 110.8 . . ?
O8 C27 H27B 110.7 . . ?
C26 C27 H27B 110.6 . . ?
H27A C27 H27B 108.8 . . ?
O7 C28 O8 122.5(6) . . ?
O7 C28 C12 123.1(7) . . ?
O8 C28 C12 113.9(6) . . ?
C3 O1 C2 117.5(5) . . ?
C25 O4 C24 118.9(8) . . ?
C20 O6 C21 116.7(5) . . ?
C28 O8 C27 115.1(6) . . ?

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
O2 C3 C4 C19 12.6(9) . . . . ?
O1 C3 C4 C19 -165.9(5) . . . . ?
O2 C3 C4 C5 -165.6(6) . . . . ?
O1 C3 C4 C5 16.0(7) . . . . ?
C19 C4 C5 C6 1.5(8) . . . . ?
C3 C4 C5 C6 179.5(5) . . . . ?
C4 C5 C6 C17 -2.7(8) . . . . ?
C4 C5 C6 C7 175.4(5) . . . . ?
C17 C6 C7 C8 -61.8(9) . . . . ?
C5 C6 C7 C8 120.1(7) . . . . ?
C6 C7 C8 C9 0.0(11) . . . . ?
C7 C8 C9 C14 60.7(9) . . . . ?
C7 C8 C9 C10 -121.5(7) . . . . ?
C14 C9 C10 C11 1.5(8) . . . . ?
C8 C9 C10 C11 -176.3(5) . . . . ?
C9 C10 C11 C12 -2.7(8) . . . . ?
C9 C10 C11 C25 -179.7(5) . . . . ?
C25 C11 C12 C28 1.4(9) . . . . ?
C10 C11 C12 C28 -175.4(6) . . . . ?
C25 C11 C12 C13 177.9(5) . . . . ?
C10 C11 C12 C13 1.2(8) . . . . ?
C11 C12 C13 C14 1.5(8) . . . . ?
C28 C12 C13 C14 178.3(5) . . . . ?
C8 C9 C14 C15 -0.9(9) . . . . ?
C10 C9 C14 C15 -178.5(5) . . . . ?
C8 C9 C14 C13 178.7(5) . . . . ?
C10 C9 C14 C13 1.1(8) . . . . ?
C12 C13 C14 C9 -2.6(8) . . . . ?
C12 C13 C14 C15 177.0(5) . . . . ?
C9 C14 C15 C16 -59.1(9) . . . . ?
C13 C14 C15 C16 121.3(7) . . . . ?
C14 C15 C16 C17 -0.7(10) . . . . ?
C7 C6 C17 C16 2.1(8) . . . . ?
C5 C6 C17 C16 -180.0(5) . . . . ?
C7 C6 C17 C18 -175.5(5) . . . . ?
C5 C6 C17 C18 2.5(8) . . . . ?
C15 C16 C17 C6 58.9(8) . . . . ?
C15 C16 C17 C18 -123.3(6) . . . . ?
C6 C17 C18 C19 -1.0(7) . . . . ?
C16 C17 C18 C19 -178.8(5) . . . . ?
C3 C4 C19 C18 -178.2(5) . . . . ?
C5 C4 C19 C18 -0.1(8) . . . . ?
C3 C4 C19 C20 -3.2(8) . . . . ?
C5 C4 C19 C20 174.9(5) . . . . ?
C17 C18 C19 C4 -0.2(7) . . . . ?
C17 C18 C19 C20 -175.7(5) . . . . ?
C4 C19 C20 O5 -103.3(7) . . . . ?
C18 C19 C20 O5 72.2(7) . . . . ?
C4 C19 C20 O6 83.6(6) . . . . ?
C18 C19 C20 O6 -101.0(5) . . . . ?
C12 C11 C25 O3 -164.6(7) . . . . ?
C10 C11 C25 O3 12.3(10) . . . . ?
C12 C11 C25 O4 16.3(9) . . . . ?
C10 C11 C25 O4 -166.8(6) . . . . ?
C11 C12 C28 O7 91.3(9) . . . . ?
C13 C12 C28 O7 -85.6(8) . . . . ?
C11 C12 C28 O8 -96.4(7) . . . . ?
C13 C12 C28 O8 86.8(7) . . . . ?
O2 C3 O1 C2 -1.3(10) . . . . ?
C4 C3 O1 C2 177.1(6) . . . . ?
C1 C2 O1 C3 -160.3(8) . . . . ?
O3 C25 O4 C24 2.4(13) . . . . ?
C11 C25 O4 C24 -178.5(7) . . . . ?
C23 C24 O4 C25 -156.6(10) . . . . ?
O5 C20 O6 C21 4.1(8) . . . . ?
C19 C20 O6 C21 177.0(5) . . . . ?
C22 C21 O6 C20 90.3(7) . . . . ?
O7 C28 O8 C27 -8.5(12) . . . . ?
C12 C28 O8 C27 179.1(8) . . . . ?
C26 C27 O8 C28 157.7(11) . . . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_IMDPH
_database_code_depnum_ccdc_archive 'CCDC 2017970'
loop_
_audit_author_name
_audit_author_address
'Sudhadevi Antharjanam'
;SAIF, IIT MADRAS
India
;
_audit_update_record             
;
2020-07-22 deposited with the CCDC.	2020-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C34 H30 N2 O6), H2O'

_chemical_formula_sum            'C68 H62 N4 O13'
_chemical_formula_weight         1143.21

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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   21.741(4)
_cell_length_b                   13.765(2)
_cell_length_c                   21.012(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6288.0(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5667
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      25.30

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_F_000             2408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6545
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'



_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11691
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.696
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_full        24.989
_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 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             2645
_reflns_number_gt                2302
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_max     0.918
_reflns_Friedel_fraction_full    0.918

_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'



_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)+(0.1150P)²+6.3671P] 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_abs_structure_details 
;
 Flack x determined using 963 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2645
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1820
_refine_ls_wR_factor_gt          0.1733
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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 0.3125(2) 0.0295(4) 0.1233(3) 0.0541(12) Uani 1 1 d . . . . .
H1 H 0.2801 0.0569 0.1460 0.065 Uiso 1 1 calc R U . . .
C2 C 0.3094(2) 0.0266(4) 0.0592(3) 0.0653(15) Uani 1 1 d . . . . .
H2 H 0.2754 0.0517 0.0381 0.078 Uiso 1 1 calc R U . . .
C3 C 0.3581(2) -0.0146(4) 0.0247(3) 0.0580(13) Uani 1 1 d . . . . .
C4 C 0.4092(2) -0.0497(4) 0.0566(2) 0.0563(13) Uani 1 1 d . . . . .
H4 H 0.4422 -0.0752 0.0339 0.068 Uiso 1 1 calc R U . . .
C5 C 0.4111(2) -0.0467(3) 0.1223(2) 0.0498(11) Uani 1 1 d . . . . .
H5 H 0.4451 -0.0713 0.1438 0.060 Uiso 1 1 calc R U . . .
C6 C 0.36252(18) -0.0073(3) 0.1561(2) 0.0429(10) Uani 1 1 d . . . . .
C7 C 0.3196(2) -0.0464(3) 0.2616(2) 0.0504(11) Uani 1 1 d . . . . .
C8 C 0.4055(2) 0.0507(3) 0.2584(2) 0.0509(11) Uani 1 1 d . . . . .
C9 C 0.3885(2) 0.0443(4) 0.3281(2) 0.0568(12) Uani 1 1 d . . . . .
H9 H 0.4220 0.0149 0.3525 0.068 Uiso 1 1 calc R U . . .
C10 C 0.3750(2) 0.1482(4) 0.3525(2) 0.0579(12) Uani 1 1 d . . . . .
H10A H 0.3694 0.1470 0.3983 0.070 Uiso 1 1 calc R U . . .
H10B H 0.4096 0.1902 0.3430 0.070 Uiso 1 1 calc R U . . .
C11 C 0.3183(2) 0.1868(3) 0.3213(2) 0.0484(11) Uani 1 1 d . . . . .
C12 C 0.2679(2) 0.1297(3) 0.3218(2) 0.0496(11) Uani 1 1 d . . . . .
C13 C 0.2743(3) 0.0333(4) 0.3556(3) 0.0622(14) Uani 1 1 d . . . . .
H13A H 0.2379 -0.0058 0.3484 0.075 Uiso 1 1 calc R U . . .
H13B H 0.2785 0.0439 0.4010 0.075 Uiso 1 1 calc R U . . .
C14 C 0.3316(2) -0.0202(3) 0.3300(2) 0.0553(12) Uani 1 1 d . . . . .
H14 H 0.3396 -0.0789 0.3551 0.066 Uiso 1 1 calc R U . . .
C15 C 0.3996(4) -0.0523(8) -0.0769(3) 0.103(3) Uani 1 1 d . . . . .
H15A H 0.4369 -0.0169 -0.0690 0.155 Uiso 1 1 calc R U . . .
H15B H 0.3889 -0.0468 -0.1211 0.155 Uiso 1 1 calc R U . . .
H15C H 0.4056 -0.1194 -0.0663 0.155 Uiso 1 1 calc R U . . .
C16 C 0.3242(2) 0.2771(3) 0.2842(3) 0.0534(12) Uani 1 1 d . . . . .
H16 H 0.3574 0.2800 0.2563 0.064 Uiso 1 1 calc R U . . .
C17 C 0.2883(2) 0.3542(3) 0.2856(2) 0.0540(12) Uani 1 1 d . . . . .
H17 H 0.3006 0.4056 0.2599 0.065 Uiso 1 1 calc R U . . .
N1 N 0.36407(15) -0.0042(3) 0.22362(18) 0.0433(9) Uani 1 1 d . . . . .
O1 O 0.3514(2) -0.0132(4) -0.0390(2) 0.0885(14) Uani 1 1 d . . . . .
O2 O 0.27717(19) -0.0928(3) 0.2409(2) 0.0756(12) Uani 1 1 d . . . . .
O3 O 0.44672(19) 0.0979(3) 0.2347(2) 0.0790(13) Uani 1 1 d . . . . .
O4 O 0.2899(14) 0.2253(19) 0.5032(8) 0.131(10) Uani 0.25 1 d . . P A -1


_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 1.348(8) . ?
C1 C6 1.384(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.403(7) . ?
C2 H2 0.9300 . ?
C3 O1 1.347(7) . ?
C3 C4 1.384(7) . ?
C4 C5 1.381(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(6) . ?
C5 H5 0.9300 . ?
C6 N1 1.419(6) . ?
C7 O2 1.203(6) . ?
C7 N1 1.382(6) . ?
C7 C14 1.505(7) . ?
C8 O3 1.213(6) . ?
C8 N1 1.384(6) . ?
C8 C9 1.513(7) . ?
C9 C14 1.524(8) . ?
C9 C10 1.547(7) . ?
C9 H9 0.9800 . ?
C10 C11 1.495(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.347(7) . ?
C11 C16 1.473(7) . ?
C12 C17 1.456(7) 14 ?
C12 C13 1.511(7) . ?
C13 C14 1.543(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14 0.9800 . ?
C15 O1 1.422(8) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.319(7) . ?
C16 H16 0.9300 . ?
C17 C12 1.456(7) 14 ?
C17 H17 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
C2 C1 C6 121.7(4) . . ?
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C1 C2 C3 119.4(5) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
O1 C3 C4 125.0(5) . . ?
O1 C3 C2 115.2(4) . . ?
C4 C3 C2 119.8(5) . . ?
C5 C4 C3 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.2(4) . . ?
C1 C6 N1 120.4(4) . . ?
C5 C6 N1 120.5(4) . . ?
O2 C7 N1 123.5(5) . . ?
O2 C7 C14 127.2(4) . . ?
N1 C7 C14 109.2(4) . . ?
O3 C8 N1 123.8(5) . . ?
O3 C8 C9 127.5(5) . . ?
N1 C8 C9 108.7(4) . . ?
C8 C9 C14 105.0(4) . . ?
C8 C9 C10 108.3(4) . . ?
C14 C9 C10 112.1(4) . . ?
C8 C9 H9 110.4 . . ?
C14 C9 H9 110.4 . . ?
C10 C9 H9 110.4 . . ?
C11 C10 C9 109.8(4) . . ?
C11 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C16 124.6(4) . . ?
C12 C11 C10 117.4(4) . . ?
C16 C11 C10 117.3(4) . . ?
C11 C12 C17 126.1(4) . 14 ?
C11 C12 C13 116.2(4) . . ?
C17 C12 C13 117.1(4) 14 . ?
C12 C13 C14 109.3(4) . . ?
C12 C13 H13A 109.8 . . ?
C14 C13 H13A 109.8 . . ?
C12 C13 H13B 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
C7 C14 C9 104.8(4) . . ?
C7 C14 C13 107.9(4) . . ?
C9 C14 C13 112.7(4) . . ?
C7 C14 H14 110.5 . . ?
C9 C14 H14 110.5 . . ?
C13 C14 H14 110.5 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C11 127.9(5) . . ?
C17 C16 H16 116.0 . . ?
C11 C16 H16 116.0 . . ?
C16 C17 C12 129.2(4) . 14 ?
C16 C17 H17 115.4 . . ?
C12 C17 H17 115.4 14 . ?
C7 N1 C8 112.4(4) . . ?
C7 N1 C6 123.2(4) . . ?
C8 N1 C6 124.0(4) . . ?
C3 O1 C15 118.1(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
C6 C1 C2 C3 0.0(9) . . . . ?
C1 C2 C3 O1 -179.3(6) . . . . ?
C1 C2 C3 C4 -1.5(8) . . . . ?
O1 C3 C4 C5 179.6(6) . . . . ?
C2 C3 C4 C5 2.0(8) . . . . ?
C3 C4 C5 C6 -1.1(8) . . . . ?
C2 C1 C6 C5 1.0(7) . . . . ?
C2 C1 C6 N1 -179.3(5) . . . . ?
C4 C5 C6 C1 -0.4(7) . . . . ?
C4 C5 C6 N1 179.9(4) . . . . ?
O3 C8 C9 C14 177.0(5) . . . . ?
N1 C8 C9 C14 -0.5(5) . . . . ?
O3 C8 C9 C10 57.1(7) . . . . ?
N1 C8 C9 C10 -120.5(4) . . . . ?
C8 C9 C10 C11 67.0(5) . . . . ?
C14 C9 C10 C11 -48.4(5) . . . . ?
C9 C10 C11 C12 49.7(6) . . . . ?
C9 C10 C11 C16 -121.1(5) . . . . ?
C16 C11 C12 C17 0.9(7) . . . 14 ?
C10 C11 C12 C17 -169.2(4) . . . 14 ?
C16 C11 C12 C13 171.6(4) . . . . ?
C10 C11 C12 C13 1.6(6) . . . . ?
C11 C12 C13 C14 -51.8(6) . . . . ?
C17 C12 C13 C14 119.8(5) 14 . . . ?
O2 C7 C14 C9 -176.2(5) . . . . ?
N1 C7 C14 C9 0.8(5) . . . . ?
O2 C7 C14 C13 -56.0(6) . . . . ?
N1 C7 C14 C13 121.1(4) . . . . ?
C8 C9 C14 C7 -0.2(5) . . . . ?
C10 C9 C14 C7 117.2(4) . . . . ?
C8 C9 C14 C13 -117.2(4) . . . . ?
C10 C9 C14 C13 0.2(6) . . . . ?
C12 C13 C14 C7 -66.6(5) . . . . ?
C12 C13 C14 C9 48.5(6) . . . . ?
C12 C11 C16 C17 56.3(7) . . . . ?
C10 C11 C16 C17 -133.6(5) . . . . ?
C11 C16 C17 C12 -2.7(9) . . . 14 ?
O2 C7 N1 C8 175.9(5) . . . . ?
C14 C7 N1 C8 -1.3(5) . . . . ?
O2 C7 N1 C6 3.3(7) . . . . ?
C14 C7 N1 C6 -173.9(3) . . . . ?
O3 C8 N1 C7 -176.5(5) . . . . ?
C9 C8 N1 C7 1.1(5) . . . . ?
O3 C8 N1 C6 -3.9(7) . . . . ?
C9 C8 N1 C6 173.7(4) . . . . ?
C1 C6 N1 C7 57.7(6) . . . . ?
C5 C6 N1 C7 -122.6(5) . . . . ?
C1 C6 N1 C8 -114.1(5) . . . . ?
C5 C6 N1 C8 65.6(5) . . . . ?
C4 C3 O1 C15 1.2(10) . . . . ?
C2 C3 O1 C15 178.9(7) . . . . ?

_refine_diff_density_max         0.631
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.090

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2017972'
loop_
_audit_author_name
_audit_author_address
'Sudhadevi Antharjanam'
;SAIF, IIT MADRAS
India
;
_audit_update_record             
;
2020-07-22 deposited with the CCDC.	2020-08-11 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         'C32 H26 N2 O4'
_chemical_formula_sum            'C32 H26 N2 O4'
_chemical_formula_weight         502.55

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           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                   13.8872(4)
_cell_length_b                   9.9072(3)
_cell_length_c                   19.4383(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.026(2)
_cell_angle_gamma                90
_cell_volume                     2674.38(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    4940
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      22.34

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4516
_exptl_absorpt_correction_T_max  0.7419
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_absorpt_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 axs kappa apex2 Diffractometer'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22953
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.095
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5837
_reflns_number_gt                3264
_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, 2004)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXT-2014/3 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_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)+(0.0720P)²+0.3419P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0054(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5837
_refine_ls_number_parameters     344
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1655
_refine_ls_wR_factor_gt          0.1333
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.015
_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 0.53948(19) 0.6159(3) 0.15257(15) 0.0783(8) Uani 1 1 d . . . . .
H1 H 0.573838 0.613303 0.193630 0.094 Uiso 1 1 calc R U . . .
C2 C 0.4586(2) 0.5344(3) 0.14378(19) 0.0924(10) Uani 1 1 d . . . . .
H2 H 0.438742 0.477007 0.178855 0.111 Uiso 1 1 calc R U . . .
C3 C 0.4090(2) 0.5395(3) 0.0834(2) 0.0885(10) Uani 1 1 d . . . . .
H3 H 0.355102 0.485041 0.077367 0.106 Uiso 1 1 calc R U . . .
C4 C 0.43711(18) 0.6226(3) 0.03207(17) 0.0841(9) Uani 1 1 d . . . . .
H4 H 0.402699 0.624734 -0.008973 0.101 Uiso 1 1 calc R U . . .
C5 C 0.51658(16) 0.7042(3) 0.04037(14) 0.0668(7) Uani 1 1 d . . . . .
H5 H 0.535405 0.762187 0.005254 0.080 Uiso 1 1 calc R U . . .
C6 C 0.56798(15) 0.6995(2) 0.10081(12) 0.0561(6) Uani 1 1 d . . . . .
C7 C 0.65284(17) 0.8987(3) 0.14939(13) 0.0658(7) Uani 1 1 d . . . . .
C8 C 0.75007(17) 0.9634(2) 0.14276(12) 0.0616(6) Uani 1 1 d . . . . .
H8 H 0.742617 1.050479 0.119424 0.074 Uiso 1 1 calc R U . . .
C9 C 0.80727(16) 0.8686(2) 0.09605(12) 0.0599(6) Uani 1 1 d . . . . .
H9 H 0.825614 0.917943 0.054383 0.072 Uiso 1 1 calc R U . . .
C10 C 0.73796(16) 0.7595(3) 0.07660(12) 0.0586(6) Uani 1 1 d . . . . .
C11 C 0.89835(15) 0.8125(2) 0.12964(12) 0.0619(6) Uani 1 1 d . . . . .
H11A H 0.919667 0.733762 0.104220 0.074 Uiso 1 1 calc R U . . .
H11B H 0.948912 0.879891 0.127111 0.074 Uiso 1 1 calc R U . . .
C12 C 0.88263(13) 0.7738(2) 0.20421(12) 0.0495(5) Uani 1 1 d . . . . .
C13 C 0.83250(14) 0.8580(2) 0.24418(12) 0.0481(5) Uani 1 1 d . . . . .
C14 C 0.79491(17) 0.9876(2) 0.21322(12) 0.0591(6) Uani 1 1 d . . . . .
H14A H 0.847394 1.051605 0.208856 0.071 Uiso 1 1 calc R U . . .
H14B H 0.747051 1.026458 0.243664 0.071 Uiso 1 1 calc R U . . .
C15 C 0.81980(14) 0.8435(2) 0.31867(12) 0.0513(5) Uani 1 1 d . . . . .
H15 H 0.838705 0.916915 0.345259 0.062 Uiso 1 1 calc R U . . .
C16 C 0.78468(15) 0.7386(2) 0.35282(11) 0.0511(5) Uani 1 1 d . . . . .
H16 H 0.782819 0.746443 0.400481 0.061 Uiso 1 1 calc R U . . .
C17 C 0.74834(14) 0.6114(2) 0.32377(10) 0.0458(5) Uani 1 1 d . . . . .
C18 C 0.79718(14) 0.5289(2) 0.28219(11) 0.0477(5) Uani 1 1 d . . . . .
C19 C 0.89772(15) 0.5484(2) 0.26031(11) 0.0540(6) Uani 1 1 d . . . . .
H19 H 0.940440 0.479268 0.271052 0.065 Uiso 1 1 calc R U . . .
C20 C 0.93393(14) 0.6523(2) 0.22736(12) 0.0553(6) Uani 1 1 d . . . . .
H20 H 0.999427 0.648654 0.217587 0.066 Uiso 1 1 calc R U . . .
C21 C 0.74955(17) 0.3990(2) 0.26033(12) 0.0591(6) Uani 1 1 d . . . . .
H21A H 0.796722 0.341013 0.238438 0.071 Uiso 1 1 calc R U . . .
H21B H 0.699424 0.418531 0.227006 0.071 Uiso 1 1 calc R U . . .
C22 C 0.70570(15) 0.3259(2) 0.32214(11) 0.0519(5) Uani 1 1 d . . . . .
H22 H 0.662501 0.254534 0.305813 0.062 Uiso 1 1 calc R U . . .
C23 C 0.65051(14) 0.4197(2) 0.37073(11) 0.0493(5) Uani 1 1 d . . . . .
H23 H 0.584023 0.387628 0.374997 0.059 Uiso 1 1 calc R U . . .
C24 C 0.64967(15) 0.5677(2) 0.34751(12) 0.0547(6) Uani 1 1 d . . . . .
H24A H 0.603946 0.578775 0.310192 0.066 Uiso 1 1 calc R U . . .
H24B H 0.629138 0.624492 0.385408 0.066 Uiso 1 1 calc R U . . .
C25 C 0.70033(14) 0.4050(2) 0.43898(12) 0.0490(5) Uani 1 1 d . . . . .
C26 C 0.78388(16) 0.2644(2) 0.36569(12) 0.0519(5) Uani 1 1 d . . . . .
C27 C 0.83631(14) 0.2708(2) 0.48828(12) 0.0511(5) Uani 1 1 d D . . . .
C28 C 0.91126(15) 0.3491(2) 0.50880(13) 0.0624(6) Uani 1 1 d D . . . .
H28 H 0.923719 0.430136 0.486390 0.075 Uiso 1 1 calc R U . . .
C29 C 0.96873(18) 0.3089(3) 0.56255(16) 0.0793(8) Uani 1 1 d D . . . .
H29 H 1.020324 0.362689 0.575959 0.095 Uiso 1 1 calc R U . . .
C30 C 0.95114(19) 0.1923(3) 0.59609(16) 0.0895(9) Uani 1 1 d D . . . .
H30 H 0.989678 0.166487 0.632962 0.107 Uiso 1 1 calc R U . . .
C31 C 0.8773(2) 0.1134(3) 0.5758(2) 0.1234(15) Uani 1 1 d D . . . .
H31 H 0.864899 0.032903 0.598758 0.148 Uiso 1 1 calc R U . . .
C32 C 0.8200(2) 0.1518(3) 0.52095(18) 0.1038(12) Uani 1 1 d D . . . .
H32 H 0.770204 0.095883 0.506403 0.125 Uiso 1 1 calc R U . . .
N1 N 0.65097(12) 0.78309(18) 0.10942(9) 0.0558(5) Uani 1 1 d . . . . .
N2 N 0.77498(11) 0.31255(16) 0.43261(9) 0.0472(4) Uani 1 1 d . . . . .
O1 O 0.58581(13) 0.9365(2) 0.18323(11) 0.0996(7) Uani 1 1 d . . . . .
O2 O 0.75196(12) 0.66504(19) 0.03874(11) 0.0847(6) Uani 1 1 d . . . . .
O3 O 0.84591(13) 0.18662(17) 0.34804(10) 0.0775(5) Uani 1 1 d . . . . .
O4 O 0.68137(12) 0.46374(17) 0.49159(9) 0.0715(5) 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 C6 1.362(3) . ?
C1 C2 1.393(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.351(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.429(3) . ?
C7 O1 1.200(3) . ?
C7 N1 1.384(3) . ?
C7 C8 1.500(3) . ?
C8 C14 1.523(3) . ?
C8 C9 1.529(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.496(3) . ?
C9 C11 1.528(3) . ?
C9 H9 0.9800 . ?
C10 O2 1.206(3) . ?
C10 N1 1.386(3) . ?
C11 C12 1.515(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.336(3) . ?
C12 C20 1.469(3) . ?
C13 C15 1.466(3) . ?
C13 C14 1.511(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.326(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.471(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.335(3) . ?
C17 C24 1.509(3) . ?
C18 C19 1.473(3) . ?
C18 C21 1.508(3) . ?
C19 C20 1.313(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.530(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C26 1.505(3) . ?
C22 C23 1.531(3) . ?
C22 H22 0.9800 . ?
C23 C25 1.503(3) . ?
C23 C24 1.534(3) . ?
C23 H23 0.9800 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 O4 1.206(3) . ?
C25 N2 1.389(3) . ?
C26 O3 1.206(3) . ?
C26 N2 1.391(3) . ?
C27 C28 1.357(3) . ?
C27 C32 1.359(3) . ?
C27 N2 1.438(3) . ?
C28 C29 1.373(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.349(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.348(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.384(4) . ?
C31 H31 0.9300 . ?
C32 H32 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
C6 C1 C2 119.7(3) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C1 C6 C5 120.1(2) . . ?
C1 C6 N1 120.0(2) . . ?
C5 C6 N1 119.9(2) . . ?
O1 C7 N1 123.5(2) . . ?
O1 C7 C8 127.8(2) . . ?
N1 C7 C8 108.8(2) . . ?
C7 C8 C14 110.9(2) . . ?
C7 C8 C9 104.85(19) . . ?
C14 C8 C9 114.71(19) . . ?
C7 C8 H8 108.7 . . ?
C14 C8 H8 108.7 . . ?
C9 C8 H8 108.7 . . ?
C10 C9 C11 112.21(19) . . ?
C10 C9 C8 105.05(18) . . ?
C11 C9 C8 113.6(2) . . ?
C10 C9 H9 108.6 . . ?
C11 C9 H9 108.6 . . ?
C8 C9 H9 108.6 . . ?
O2 C10 N1 123.5(2) . . ?
O2 C10 C9 127.7(2) . . ?
N1 C10 C9 108.8(2) . . ?
C12 C11 C9 112.41(17) . . ?
C12 C11 H11A 109.1 . . ?
C9 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C9 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C20 125.9(2) . . ?
C13 C12 C11 118.24(19) . . ?
C20 C12 C11 115.51(19) . . ?
C12 C13 C15 125.18(19) . . ?
C12 C13 C14 118.6(2) . . ?
C15 C13 C14 115.80(19) . . ?
C13 C14 C8 111.46(18) . . ?
C13 C14 H14A 109.3 . . ?
C8 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C8 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C13 128.0(2) . . ?
C16 C15 H15 116.0 . . ?
C13 C15 H15 116.0 . . ?
C15 C16 C17 127.3(2) . . ?
C15 C16 H16 116.4 . . ?
C17 C16 H16 116.4 . . ?
C18 C17 C16 125.67(18) . . ?
C18 C17 C24 118.10(18) . . ?
C16 C17 C24 116.09(18) . . ?
C17 C18 C19 125.20(19) . . ?
C17 C18 C21 118.05(18) . . ?
C19 C18 C21 116.54(18) . . ?
C20 C19 C18 127.41(19) . . ?
C20 C19 H19 116.3 . . ?
C18 C19 H19 116.3 . . ?
C19 C20 C12 127.30(19) . . ?
C19 C20 H20 116.3 . . ?
C12 C20 H20 116.3 . . ?
C18 C21 C22 110.94(18) . . ?
C18 C21 H21A 109.5 . . ?
C22 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 108.0 . . ?
C26 C22 C21 110.26(18) . . ?
C26 C22 C23 105.07(18) . . ?
C21 C22 C23 113.38(17) . . ?
C26 C22 H22 109.3 . . ?
C21 C22 H22 109.3 . . ?
C23 C22 H22 109.3 . . ?
C25 C23 C22 104.82(17) . . ?
C25 C23 C24 110.82(18) . . ?
C22 C23 C24 113.72(17) . . ?
C25 C23 H23 109.1 . . ?
C22 C23 H23 109.1 . . ?
C24 C23 H23 109.1 . . ?
C17 C24 C23 110.92(17) . . ?
C17 C24 H24A 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C17 C24 H24B 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 108.0 . . ?
O4 C25 N2 123.9(2) . . ?
O4 C25 C23 127.0(2) . . ?
N2 C25 C23 109.16(19) . . ?
O3 C26 N2 123.3(2) . . ?
O3 C26 C22 127.9(2) . . ?
N2 C26 C22 108.81(18) . . ?
C28 C27 C32 119.1(2) . . ?
C28 C27 N2 120.73(19) . . ?
C32 C27 N2 120.18(19) . . ?
C27 C28 C29 120.2(2) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C30 C29 C28 120.7(2) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C31 C30 C29 119.5(3) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C30 C31 C32 120.2(3) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C27 C32 C31 120.2(2) . . ?
C27 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C7 N1 C10 112.4(2) . . ?
C7 N1 C6 124.08(18) . . ?
C10 N1 C6 123.44(18) . . ?
C25 N2 C26 112.10(18) . . ?
C25 N2 C27 124.37(18) . . ?
C26 N2 C27 123.53(17) . . ?

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 -0.1(4) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
C2 C1 C6 N1 -179.8(2) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C4 C5 C6 N1 179.5(2) . . . . ?
O1 C7 C8 C14 53.0(3) . . . . ?
N1 C7 C8 C14 -126.6(2) . . . . ?
O1 C7 C8 C9 177.4(3) . . . . ?
N1 C7 C8 C9 -2.2(3) . . . . ?
C7 C8 C9 C10 2.4(2) . . . . ?
C14 C8 C9 C10 124.4(2) . . . . ?
C7 C8 C9 C11 -120.6(2) . . . . ?
C14 C8 C9 C11 1.4(3) . . . . ?
C11 C9 C10 O2 -58.3(3) . . . . ?
C8 C9 C10 O2 177.9(2) . . . . ?
C11 C9 C10 N1 122.0(2) . . . . ?
C8 C9 C10 N1 -1.9(2) . . . . ?
C10 C9 C11 C12 -78.0(3) . . . . ?
C8 C9 C11 C12 41.0(3) . . . . ?
C9 C11 C12 C13 -43.5(3) . . . . ?
C9 C11 C12 C20 142.95(19) . . . . ?
C20 C12 C13 C15 -0.1(3) . . . . ?
C11 C12 C13 C15 -172.89(19) . . . . ?
C20 C12 C13 C14 172.29(19) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 C8 44.4(3) . . . . ?
C15 C13 C14 C8 -142.4(2) . . . . ?
C7 C8 C14 C13 75.5(2) . . . . ?
C9 C8 C14 C13 -43.0(3) . . . . ?
C12 C13 C15 C16 -55.9(3) . . . . ?
C14 C13 C15 C16 131.5(2) . . . . ?
C13 C15 C16 C17 -1.0(4) . . . . ?
C15 C16 C17 C18 55.8(3) . . . . ?
C15 C16 C17 C24 -128.6(2) . . . . ?
C16 C17 C18 C19 2.6(3) . . . . ?
C24 C17 C18 C19 -173.0(2) . . . . ?
C16 C17 C18 C21 177.0(2) . . . . ?
C24 C17 C18 C21 1.4(3) . . . . ?
C17 C18 C19 C20 -58.4(4) . . . . ?
C21 C18 C19 C20 127.1(3) . . . . ?
C18 C19 C20 C12 -0.3(4) . . . . ?
C13 C12 C20 C19 57.2(3) . . . . ?
C11 C12 C20 C19 -129.8(2) . . . . ?
C17 C18 C21 C22 -47.6(3) . . . . ?
C19 C18 C21 C22 127.4(2) . . . . ?
C18 C21 C22 C26 -73.2(2) . . . . ?
C18 C21 C22 C23 44.3(2) . . . . ?
C26 C22 C23 C25 -0.33(19) . . . . ?
C21 C22 C23 C25 -120.80(19) . . . . ?
C26 C22 C23 C24 120.85(18) . . . . ?
C21 C22 C23 C24 0.4(2) . . . . ?
C18 C17 C24 C23 45.3(3) . . . . ?
C16 C17 C24 C23 -130.7(2) . . . . ?
C25 C23 C24 C17 73.6(2) . . . . ?
C22 C23 C24 C17 -44.2(2) . . . . ?
C22 C23 C25 O4 178.2(2) . . . . ?
C24 C23 C25 O4 55.1(3) . . . . ?
C22 C23 C25 N2 -0.9(2) . . . . ?
C24 C23 C25 N2 -123.95(17) . . . . ?
C21 C22 C26 O3 -55.6(3) . . . . ?
C23 C22 C26 O3 -178.1(2) . . . . ?
C21 C22 C26 N2 123.95(18) . . . . ?
C23 C22 C26 N2 1.4(2) . . . . ?
C32 C27 C28 C29 -1.0(4) . . . . ?
N2 C27 C28 C29 179.3(2) . . . . ?
C27 C28 C29 C30 -0.7(4) . . . . ?
C28 C29 C30 C31 1.1(5) . . . . ?
C29 C30 C31 C32 0.0(6) . . . . ?
C28 C27 C32 C31 2.1(5) . . . . ?
N2 C27 C32 C31 -178.1(3) . . . . ?
C30 C31 C32 C27 -1.6(6) . . . . ?
O1 C7 N1 C10 -178.5(2) . . . . ?
C8 C7 N1 C10 1.1(3) . . . . ?
O1 C7 N1 C6 3.5(4) . . . . ?
C8 C7 N1 C6 -176.8(2) . . . . ?
O2 C10 N1 C7 -179.3(2) . . . . ?
C9 C10 N1 C7 0.5(3) . . . . ?
O2 C10 N1 C6 -1.3(4) . . . . ?
C9 C10 N1 C6 178.5(2) . . . . ?
C1 C6 N1 C7 -74.9(3) . . . . ?
C5 C6 N1 C7 104.6(3) . . . . ?
C1 C6 N1 C10 107.3(3) . . . . ?
C5 C6 N1 C10 -73.1(3) . . . . ?
O4 C25 N2 C26 -177.22(19) . . . . ?
C23 C25 N2 C26 1.9(2) . . . . ?
O4 C25 N2 C27 2.7(3) . . . . ?
C23 C25 N2 C27 -178.13(16) . . . . ?
O3 C26 N2 C25 177.47(19) . . . . ?
C22 C26 N2 C25 -2.1(2) . . . . ?
O3 C26 N2 C27 -2.5(3) . . . . ?
C22 C26 N2 C27 177.91(16) . . . . ?
C28 C27 N2 C25 -80.3(3) . . . . ?
C32 C27 N2 C25 99.9(3) . . . . ?
C28 C27 N2 C26 99.6(2) . . . . ?
C32 C27 N2 C26 -80.1(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
C8 H8 O4 0.98 2.63 3.172(3) 115.1 4_575 yes
C9 H9 O4 0.98 2.62 3.152(3) 114.2 4_575 yes

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.037

