# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_datam
_database_code_depnum_ccdc_archive 'CCDC 2195956'
loop_
_audit_author_name
_audit_author_address
'Dr. B. Sridhar'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-08-10 deposited with the CCDC.	2023-01-19 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         ?
_chemical_formula_sum            'C24 H18 N2 O5'
_chemical_formula_weight         414.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.1443(5)
_cell_length_b                   9.6794(6)
_cell_length_c                   13.0717(8)
_cell_angle_alpha                81.178(2)
_cell_angle_beta                 89.732(3)
_cell_angle_gamma                83.318(2)
_cell_volume                     1011.27(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    303(2)
_cell_measurement_reflns_used    6140
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      30.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      303(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III-C7'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23684
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.458
_diffrn_reflns_theta_max         30.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6140
_reflns_number_gt                2561
_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       ?
_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)+(0.0708P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6140
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1567
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1751
_refine_ls_wR_factor_gt          0.1315
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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 0.4388(2) 0.15890(18) 0.74730(13) 0.0441(4) Uani 1 1 d . . . . .
C2 C 0.5161(3) 0.0277(2) 0.78985(15) 0.0551(5) Uani 1 1 d . . . . .
H2 H 0.503735 -0.004451 0.859925 0.066 Uiso 1 1 calc R U . . .
C3 C 0.6111(3) -0.0564(2) 0.73029(17) 0.0606(6) Uani 1 1 d . . . . .
H3 H 0.662146 -0.144001 0.760603 0.073 Uiso 1 1 calc R U . . .
C4 C 0.6304(3) -0.0117(2) 0.62729(17) 0.0615(6) Uani 1 1 d . . . . .
H4 H 0.696532 -0.067225 0.587554 0.074 Uiso 1 1 calc R U . . .
C5 C 0.5508(3) 0.1165(2) 0.58280(15) 0.0566(5) Uani 1 1 d . . . . .
H5 H 0.562242 0.145913 0.512246 0.068 Uiso 1 1 calc R U . . .
C6 C 0.4537(2) 0.20350(18) 0.64066(13) 0.0440(4) Uani 1 1 d . . . . .
C7 C 0.3670(2) 0.3395(2) 0.58650(14) 0.0495(5) Uani 1 1 d . . . . .
C8 C 0.2836(3) 0.4688(2) 0.41923(17) 0.0737(7) Uani 1 1 d . . . . .
H8A H 0.350638 0.502981 0.361405 0.088 Uiso 1 1 calc R U . . .
H8B H 0.256202 0.544423 0.459417 0.088 Uiso 1 1 calc R U . . .
C9 C 0.1311(3) 0.4257(3) 0.38052(19) 0.0829(7) Uani 1 1 d . . . . .
H9A H 0.072382 0.503661 0.335962 0.124 Uiso 1 1 calc R U . . .
H9B H 0.062718 0.396121 0.437889 0.124 Uiso 1 1 calc R U . . .
H9C H 0.158643 0.349043 0.342427 0.124 Uiso 1 1 calc R U . . .
C10 C 0.3507(2) 0.25504(18) 0.81810(13) 0.0447(4) Uani 1 1 d . . . . .
H10 H 0.253187 0.307818 0.781016 0.054 Uiso 1 1 calc R U . . .
C11 C 0.2958(3) 0.1748(2) 0.91367(16) 0.0567(5) Uani 1 1 d . . . . .
C12 C 0.4642(2) 0.36111(18) 0.84496(12) 0.0432(4) Uani 1 1 d . . . . .
C13 C 0.4042(2) 0.50124(19) 0.85053(13) 0.0435(4) Uani 1 1 d . . . . .
C14 C 0.5144(2) 0.5941(2) 0.87054(14) 0.0517(5) Uani 1 1 d . . . . .
H14 H 0.475151 0.687705 0.872718 0.062 Uiso 1 1 calc R U . . .
C15 C 0.6807(2) 0.5497(2) 0.88716(15) 0.0565(5) Uani 1 1 d . . . . .
H15 H 0.752623 0.612297 0.901635 0.068 Uiso 1 1 calc R U . . .
C16 C 0.7386(2) 0.4117(2) 0.88205(15) 0.0583(5) Uani 1 1 d . . . . .
H16 H 0.850484 0.380752 0.893113 0.070 Uiso 1 1 calc R U . . .
C17 C 0.6323(2) 0.3192(2) 0.86070(14) 0.0519(5) Uani 1 1 d . . . . .
H17 H 0.673780 0.226571 0.856698 0.062 Uiso 1 1 calc R U . . .
C18 C 0.2248(2) 0.5535(2) 0.84479(14) 0.0493(5) Uani 1 1 d . . . . .
C19 C 0.1735(2) 0.7036(2) 0.79849(14) 0.0493(5) Uani 1 1 d . . . . .
C20 C 0.2226(3) 0.7573(2) 0.70054(16) 0.0631(6) Uani 1 1 d . . . . .
H20 H 0.294127 0.701279 0.663974 0.076 Uiso 1 1 calc R U . . .
C21 C 0.1666(3) 0.8927(2) 0.65675(16) 0.0645(6) Uani 1 1 d . . . . .
H21 H 0.194875 0.927425 0.589485 0.077 Uiso 1 1 calc R U . . .
C22 C 0.0678(2) 0.9758(2) 0.71434(16) 0.0550(5) Uani 1 1 d . . . . .
C23 C 0.0197(3) 0.9272(2) 0.81257(16) 0.0618(6) Uani 1 1 d . . . . .
H23 H -0.045335 0.985768 0.850672 0.074 Uiso 1 1 calc R U . . .
C24 C 0.0706(2) 0.7888(2) 0.85340(15) 0.0594(5) Uani 1 1 d . . . . .
H24 H 0.035182 0.752331 0.918691 0.071 Uiso 1 1 calc R U . . .
N1 N 0.2535(3) 0.1129(2) 0.98909(15) 0.0847(6) Uani 1 1 d . . . . .
N2 N 0.0109(2) 1.12189(19) 0.66849(18) 0.0730(5) Uani 1 1 d . . . . .
O1 O 0.29686(19) 0.43057(14) 0.62838(11) 0.0720(5) Uani 1 1 d . . . . .
O2 O 0.37666(19) 0.34796(14) 0.48420(10) 0.0699(4) Uani 1 1 d . . . . .
O3 O 0.12078(17) 0.47909(14) 0.87948(11) 0.0637(4) Uani 1 1 d . . . . .
O4 O -0.0536(3) 1.20041(17) 0.72485(16) 0.1131(7) Uani 1 1 d . . . . .
O5 O 0.0320(3) 1.15744(18) 0.57711(16) 0.1076(7) 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 1.385(2) . ?
C1 C6 1.404(2) . ?
C1 C10 1.530(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.495(3) . ?
C7 O1 1.196(2) . ?
C7 O2 1.330(2) . ?
C8 O2 1.469(2) . ?
C8 C9 1.471(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.464(3) . ?
C10 C12 1.538(2) . ?
C10 H10 0.9800 . ?
C11 N1 1.146(2) . ?
C12 C17 1.388(2) . ?
C12 C13 1.400(2) . ?
C13 C14 1.394(2) . ?
C13 C18 1.487(3) . ?
C14 C15 1.380(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O3 1.217(2) . ?
C18 C19 1.498(3) . ?
C19 C20 1.381(3) . ?
C19 C24 1.383(2) . ?
C20 C21 1.374(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.375(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.370(3) . ?
C22 N2 1.471(3) . ?
C23 C24 1.380(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
N2 O5 1.209(2) . ?
N2 O4 1.213(2) . ?

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 118.56(15) . . ?
C2 C1 C10 119.53(16) . . ?
C6 C1 C10 121.77(16) . . ?
C3 C2 C1 121.34(19) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 C2 120.34(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.28(18) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 121.73(18) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 118.69(17) . . ?
C5 C6 C7 118.76(17) . . ?
C1 C6 C7 122.54(15) . . ?
O1 C7 O2 123.27(18) . . ?
O1 C7 C6 125.21(17) . . ?
O2 C7 C6 111.53(15) . . ?
O2 C8 C9 109.51(18) . . ?
O2 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
O2 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C1 111.84(15) . . ?
C11 C10 C12 109.46(14) . . ?
C1 C10 C12 110.66(14) . . ?
C11 C10 H10 108.3 . . ?
C1 C10 H10 108.3 . . ?
C12 C10 H10 108.3 . . ?
N1 C11 C10 179.2(2) . . ?
C17 C12 C13 118.49(16) . . ?
C17 C12 C10 119.59(16) . . ?
C13 C12 C10 121.88(16) . . ?
C14 C13 C12 119.23(17) . . ?
C14 C13 C18 117.84(16) . . ?
C12 C13 C18 122.73(16) . . ?
C15 C14 C13 121.28(18) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C14 119.13(18) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C17 C16 C15 120.42(19) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 121.44(18) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
O3 C18 C13 121.75(18) . . ?
O3 C18 C19 119.78(17) . . ?
C13 C18 C19 118.43(17) . . ?
C20 C19 C24 119.35(19) . . ?
C20 C19 C18 121.23(16) . . ?
C24 C19 C18 119.39(17) . . ?
C21 C20 C19 120.51(18) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 118.67(19) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C23 C22 C21 122.37(19) . . ?
C23 C22 N2 118.86(18) . . ?
C21 C22 N2 118.77(19) . . ?
C22 C23 C24 118.13(17) . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
C23 C24 C19 120.85(19) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
O5 N2 O4 123.6(2) . . ?
O5 N2 C22 118.33(19) . . ?
O4 N2 C22 118.0(2) . . ?
C7 O2 C8 118.40(15) . . ?

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 2.4(3) . . . . ?
C10 C1 C2 C3 -173.34(17) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 C6 C7 -178.24(18) . . . . ?
C2 C1 C6 C5 -2.6(3) . . . . ?
C10 C1 C6 C5 173.04(16) . . . . ?
C2 C1 C6 C7 176.38(16) . . . . ?
C10 C1 C6 C7 -8.0(3) . . . . ?
C5 C6 C7 O1 -170.49(19) . . . . ?
C1 C6 C7 O1 10.6(3) . . . . ?
C5 C6 C7 O2 9.6(2) . . . . ?
C1 C6 C7 O2 -169.35(17) . . . . ?
C2 C1 C10 C11 -25.9(2) . . . . ?
C6 C1 C10 C11 158.59(17) . . . . ?
C2 C1 C10 C12 96.47(19) . . . . ?
C6 C1 C10 C12 -79.1(2) . . . . ?
C11 C10 C12 C17 86.69(19) . . . . ?
C1 C10 C12 C17 -37.0(2) . . . . ?
C11 C10 C12 C13 -95.64(19) . . . . ?
C1 C10 C12 C13 140.65(16) . . . . ?
C17 C12 C13 C14 0.6(2) . . . . ?
C10 C12 C13 C14 -177.06(15) . . . . ?
C17 C12 C13 C18 -174.07(16) . . . . ?
C10 C12 C13 C18 8.2(3) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
C18 C13 C14 C15 173.52(17) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C12 -0.8(3) . . . . ?
C13 C12 C17 C16 0.5(3) . . . . ?
C10 C12 C17 C16 178.21(16) . . . . ?
C14 C13 C18 O3 -141.76(18) . . . . ?
C12 C13 C18 O3 33.0(3) . . . . ?
C14 C13 C18 C19 35.9(2) . . . . ?
C12 C13 C18 C19 -149.33(16) . . . . ?
O3 C18 C19 C20 -127.6(2) . . . . ?
C13 C18 C19 C20 54.7(2) . . . . ?
O3 C18 C19 C24 50.2(3) . . . . ?
C13 C18 C19 C24 -127.48(18) . . . . ?
C24 C19 C20 C21 -1.7(3) . . . . ?
C18 C19 C20 C21 176.15(18) . . . . ?
C19 C20 C21 C22 3.3(3) . . . . ?
C20 C21 C22 C23 -1.8(3) . . . . ?
C20 C21 C22 N2 178.55(19) . . . . ?
C21 C22 C23 C24 -1.3(3) . . . . ?
N2 C22 C23 C24 178.33(19) . . . . ?
C22 C23 C24 C19 3.0(3) . . . . ?
C20 C19 C24 C23 -1.5(3) . . . . ?
C18 C19 C24 C23 -179.40(18) . . . . ?
C23 C22 N2 O5 -168.8(2) . . . . ?
C21 C22 N2 O5 10.8(3) . . . . ?
C23 C22 N2 O4 11.8(3) . . . . ?
C21 C22 N2 O4 -168.6(2) . . . . ?
O1 C7 O2 C8 -6.0(3) . . . . ?
C6 C7 O2 C8 173.90(17) . . . . ?
C9 C8 O2 C7 -100.8(2) . . . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.040



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

data_datam_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2195957'
loop_
_audit_author_name
_audit_author_address
'Dr. B. Sridhar'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-08-10 deposited with the CCDC.	2023-01-19 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         ?
_chemical_formula_sum            'C21 H20 N0 O6'
_chemical_formula_weight         368.37

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   24.577(3)
_cell_length_b                   8.2885(10)
_cell_length_c                   18.262(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.819(7)
_cell_angle_gamma                90
_cell_volume                     3641.2(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    303(2)
_cell_measurement_reflns_used    5565
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      30.6

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      303(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III-C7'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32086
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.546
_diffrn_reflns_theta_max         30.582
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5565
_reflns_number_gt                3257
_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       ?
_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)+(0.1170P)²+0.9643P] 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         5565
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.2097
_refine_ls_wR_factor_gt          0.1645
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
O3 O 0.65579(5) 0.86860(14) 0.56678(7) 0.0516(3) Uani 1 1 d . . . . .
O5 O 0.54811(5) 0.45445(17) 0.56123(9) 0.0681(4) Uani 1 1 d . . . . .
O1 O 0.69559(6) 0.56735(17) 0.36108(8) 0.0648(4) Uani 1 1 d . . . . .
O6 O 0.56100(7) 0.96785(18) 0.85118(8) 0.0705(4) Uani 1 1 d . . . . .
O2 O 0.64785(6) 0.43008(16) 0.46688(8) 0.0702(4) Uani 1 1 d . . . . .
O4 O 0.62562(6) 0.34539(16) 0.62790(9) 0.0669(4) Uani 1 1 d . . . . .
C12 C 0.60235(7) 0.4514(2) 0.58902(10) 0.0479(4) Uani 1 1 d . . . . .
C5 C 0.69180(7) 0.9997(2) 0.47504(11) 0.0509(4) Uani 1 1 d . . . . .
H5 H 0.691017 1.094692 0.501926 0.061 Uiso 1 1 calc R U . . .
C1 C 0.67370(7) 0.7083(2) 0.46362(10) 0.0459(4) Uani 1 1 d . . . . .
C10 C 0.63001(7) 0.5950(2) 0.56287(10) 0.0456(4) Uani 1 1 d . . . . .
C6 C 0.67382(7) 0.8548(2) 0.50055(10) 0.0463(4) Uani 1 1 d . . . . .
C9 C 0.63298(6) 0.74108(19) 0.59679(10) 0.0443(4) Uani 1 1 d . . . . .
C11 C 0.65125(7) 0.5654(2) 0.49474(10) 0.0486(4) Uani 1 1 d . . . . .
C4 C 0.71074(7) 0.9992(2) 0.40921(11) 0.0514(4) Uani 1 1 d . . . . .
C15 C 0.61423(7) 0.7926(2) 0.66447(10) 0.0460(4) Uani 1 1 d . . . . .
C18 C 0.57827(8) 0.9027(2) 0.79173(11) 0.0539(4) Uani 1 1 d . . . . .
C3 C 0.71255(8) 0.8541(2) 0.37116(11) 0.0540(4) Uani 1 1 d . . . . .
H3 H 0.726136 0.853876 0.327225 0.065 Uiso 1 1 calc R U . . .
C2 C 0.69474(7) 0.7106(2) 0.39681(10) 0.0498(4) Uani 1 1 d . . . . .
C8 C 0.72920(9) 1.1539(2) 0.37866(13) 0.0648(5) Uani 1 1 d . . . . .
H8A H 0.716321 1.156494 0.325369 0.097 Uiso 1 1 calc R U . . .
H8B H 0.769052 1.159859 0.390323 0.097 Uiso 1 1 calc R U . . .
H8C H 0.714014 1.243908 0.400798 0.097 Uiso 1 1 calc R U . . .
C16 C 0.60718(8) 0.9577(2) 0.67687(11) 0.0561(5) Uani 1 1 d . . . . .
H16 H 0.614814 1.032375 0.642318 0.067 Uiso 1 1 calc R U . . .
C13 C 0.51427(9) 0.3181(3) 0.57793(15) 0.0732(6) Uani 1 1 d . . . . .
H13A H 0.487451 0.287863 0.533330 0.088 Uiso 1 1 calc R U . . .
H13B H 0.537916 0.225815 0.594173 0.088 Uiso 1 1 calc R U . . .
C19 C 0.58667(8) 0.7391(2) 0.78193(11) 0.0586(5) Uani 1 1 d . . . . .
H19 H 0.580345 0.665302 0.817614 0.070 Uiso 1 1 calc R U . . .
C17 C 0.58929(9) 1.0108(2) 0.73884(12) 0.0628(5) Uani 1 1 d . . . . .
H17 H 0.584471 1.120726 0.745496 0.075 Uiso 1 1 calc R U . . .
C20 C 0.60444(8) 0.6865(2) 0.71898(11) 0.0543(4) Uani 1 1 d . . . . .
H20 H 0.609993 0.576694 0.713012 0.065 Uiso 1 1 calc R U . . .
C7 C 0.72067(10) 0.5628(3) 0.29761(12) 0.0688(6) Uani 1 1 d . . . . .
H7A H 0.720360 0.454010 0.279435 0.103 Uiso 1 1 calc R U . . .
H7B H 0.758347 0.600195 0.311425 0.103 Uiso 1 1 calc R U . . .
H7C H 0.700261 0.630944 0.259084 0.103 Uiso 1 1 calc R U . . .
C21 C 0.54760(11) 0.8629(3) 0.90630(14) 0.0782(7) Uani 1 1 d . . . . .
H21A H 0.518068 0.791907 0.883554 0.117 Uiso 1 1 calc R U . . .
H21B H 0.535926 0.925317 0.944597 0.117 Uiso 1 1 calc R U . . .
H21C H 0.579738 0.800331 0.928032 0.117 Uiso 1 1 calc R U . . .
C14 C 0.48565(14) 0.3657(3) 0.6364(2) 0.1074(10) Uani 1 1 d . . . . .
H14A H 0.512423 0.390502 0.681079 0.161 Uiso 1 1 calc R U . . .
H14B H 0.462304 0.278857 0.646223 0.161 Uiso 1 1 calc R U . . .
H14C H 0.463254 0.459163 0.620589 0.161 Uiso 1 1 calc R U . . .


_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
O3 C9 1.3628(19) . ?
O3 C6 1.376(2) . ?
O5 C12 1.326(2) . ?
O5 C13 1.472(2) . ?
O1 C2 1.357(2) . ?
O1 C7 1.420(2) . ?
O6 C18 1.356(2) . ?
O6 C21 1.419(3) . ?
O2 C11 1.227(2) . ?
O4 C12 1.198(2) . ?
C12 C10 1.497(2) . ?
C5 C4 1.375(3) . ?
C5 C6 1.393(2) . ?
C5 H5 0.9300 . ?
C1 C6 1.389(2) . ?
C1 C2 1.420(3) . ?
C1 C11 1.469(2) . ?
C10 C9 1.355(2) . ?
C10 C11 1.465(3) . ?
C9 C15 1.468(3) . ?
C4 C3 1.394(3) . ?
C4 C8 1.504(2) . ?
C15 C20 1.386(2) . ?
C15 C16 1.403(3) . ?
C18 C17 1.384(3) . ?
C18 C19 1.389(3) . ?
C3 C2 1.382(2) . ?
C3 H3 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C16 C17 1.368(3) . ?
C16 H16 0.9300 . ?
C13 C14 1.448(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C19 C20 1.381(3) . ?
C19 H19 0.9300 . ?
C17 H17 0.9300 . ?
C20 H20 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C9 O3 C6 121.47(14) . . ?
C12 O5 C13 118.20(15) . . ?
C2 O1 C7 117.89(15) . . ?
C18 O6 C21 118.68(17) . . ?
O4 C12 O5 124.14(16) . . ?
O4 C12 C10 125.39(16) . . ?
O5 C12 C10 110.43(14) . . ?
C4 C5 C6 118.50(17) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C6 C1 C2 116.13(15) . . ?
C6 C1 C11 118.74(16) . . ?
C2 C1 C11 125.12(16) . . ?
C9 C10 C11 122.85(15) . . ?
C9 C10 C12 123.39(16) . . ?
C11 C10 C12 113.69(15) . . ?
O3 C6 C1 122.06(14) . . ?
O3 C6 C5 113.80(15) . . ?
C1 C6 C5 124.14(16) . . ?
C10 C9 O3 119.83(15) . . ?
C10 C9 C15 130.38(15) . . ?
O3 C9 C15 109.78(14) . . ?
O2 C11 C10 119.96(15) . . ?
O2 C11 C1 125.13(17) . . ?
C10 C11 C1 114.88(15) . . ?
C5 C4 C3 119.29(16) . . ?
C5 C4 C8 120.22(18) . . ?
C3 C4 C8 120.48(17) . . ?
C20 C15 C16 117.23(17) . . ?
C20 C15 C9 123.40(16) . . ?
C16 C15 C9 119.35(16) . . ?
O6 C18 C17 116.06(18) . . ?
O6 C18 C19 124.81(17) . . ?
C17 C18 C19 119.12(18) . . ?
C2 C3 C4 121.93(17) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
O1 C2 C3 123.58(16) . . ?
O1 C2 C1 116.44(15) . . ?
C3 C2 C1 119.98(17) . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C17 C16 C15 121.23(17) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C14 C13 O5 108.9(2) . . ?
C14 C13 H13A 109.9 . . ?
O5 C13 H13A 109.9 . . ?
C14 C13 H13B 109.9 . . ?
O5 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C20 C19 C18 119.75(17) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C16 C17 C18 120.73(18) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C20 C15 121.88(17) . . ?
C19 C20 H20 119.1 . . ?
C15 C20 H20 119.1 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O6 C21 H21A 109.5 . . ?
O6 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O6 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 O5 C12 O4 -1.1(3) . . . . ?
C13 O5 C12 C10 177.04(18) . . . . ?
O4 C12 C10 C9 -97.7(2) . . . . ?
O5 C12 C10 C9 84.2(2) . . . . ?
O4 C12 C10 C11 85.2(2) . . . . ?
O5 C12 C10 C11 -92.87(18) . . . . ?
C9 O3 C6 C1 -4.9(2) . . . . ?
C9 O3 C6 C5 175.09(14) . . . . ?
C2 C1 C6 O3 -178.46(14) . . . . ?
C11 C1 C6 O3 2.8(3) . . . . ?
C2 C1 C6 C5 1.5(3) . . . . ?
C11 C1 C6 C5 -177.23(16) . . . . ?
C4 C5 C6 O3 179.97(15) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C11 C10 C9 O3 1.0(2) . . . . ?
C12 C10 C9 O3 -175.86(15) . . . . ?
C11 C10 C9 C15 -179.93(16) . . . . ?
C12 C10 C9 C15 3.2(3) . . . . ?
C6 O3 C9 C10 2.9(2) . . . . ?
C6 O3 C9 C15 -176.30(14) . . . . ?
C9 C10 C11 O2 179.34(17) . . . . ?
C12 C10 C11 O2 -3.5(2) . . . . ?
C9 C10 C11 C1 -2.8(2) . . . . ?
C12 C10 C11 C1 174.29(14) . . . . ?
C6 C1 C11 O2 178.62(18) . . . . ?
C2 C1 C11 O2 0.0(3) . . . . ?
C6 C1 C11 C10 0.9(2) . . . . ?
C2 C1 C11 C10 -177.70(15) . . . . ?
C6 C5 C4 C3 -1.4(3) . . . . ?
C6 C5 C4 C8 178.47(17) . . . . ?
C10 C9 C15 C20 20.3(3) . . . . ?
O3 C9 C15 C20 -160.59(16) . . . . ?
C10 C9 C15 C16 -161.72(18) . . . . ?
O3 C9 C15 C16 17.4(2) . . . . ?
C21 O6 C18 C17 178.3(2) . . . . ?
C21 O6 C18 C19 -3.3(3) . . . . ?
C5 C4 C3 C2 1.4(3) . . . . ?
C8 C4 C3 C2 -178.53(18) . . . . ?
C7 O1 C2 C3 5.7(3) . . . . ?
C7 O1 C2 C1 -174.80(16) . . . . ?
C4 C3 C2 O1 179.62(17) . . . . ?
C4 C3 C2 C1 0.2(3) . . . . ?
C6 C1 C2 O1 178.95(15) . . . . ?
C11 C1 C2 O1 -2.4(3) . . . . ?
C6 C1 C2 C3 -1.6(3) . . . . ?
C11 C1 C2 C3 177.10(16) . . . . ?
C20 C15 C16 C17 -2.5(3) . . . . ?
C9 C15 C16 C17 179.38(17) . . . . ?
C12 O5 C13 C14 101.9(3) . . . . ?
O6 C18 C19 C20 -179.93(18) . . . . ?
C17 C18 C19 C20 -1.6(3) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
O6 C18 C17 C16 179.72(19) . . . . ?
C19 C18 C17 C16 1.3(3) . . . . ?
C18 C19 C20 C15 -0.1(3) . . . . ?
C16 C15 C20 C19 2.1(3) . . . . ?
C9 C15 C20 C19 -179.82(17) . . . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.040



