# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_20240227-pablo_auto
_database_code_depnum_ccdc_archive 'CCDC 2407098'
loop_
_audit_author_name
_audit_author_address
'Sonia Mallet Ladeira'
;Laboratoire de Chimie de Coordination
France
;
_audit_update_record             
;
2024-12-02 deposited with the CCDC.	2025-05-12 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            'C20 H12 O5'
_chemical_formula_weight         332.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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                   12.84670(10)
_cell_length_b                   9.54310(10)
_cell_length_c                   12.05780(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.8450(10)
_cell_angle_gamma                90
_cell_volume                     1472.97(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    18230
_cell_measurement_theta_min      3.4370
_cell_measurement_theta_max      79.2660

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.903
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.48407
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            29806
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.453
_diffrn_reflns_theta_max         79.929
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3189
_reflns_number_gt                2975
_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       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_structure_solution    ?
_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)+(0.0530P)²+0.7336P] 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         3189
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1064
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.16393(10) 0.54986(14) 0.52190(10) 0.0214(3) Uani 1 1 d . . . . .
H1 H 0.116657 0.546122 0.456982 0.026 Uiso 1 1 calc R U . . .
C1' C 0.43338(10) 0.23729(15) 0.36651(10) 0.0217(3) Uani 1 1 d . . . . .
H10 H 0.393055 0.221003 0.298006 0.026 Uiso 1 1 calc R U . . .
C2 C 0.13664(10) 0.62580(14) 0.61258(11) 0.0216(3) Uani 1 1 d . . . . .
H2 H 0.072158 0.674984 0.609212 0.026 Uiso 1 1 calc R U . . .
C2' C 0.53003(10) 0.17479(14) 0.38455(11) 0.0214(3) Uani 1 1 d . . . . .
H2' H 0.555887 0.116257 0.329369 0.026 Uiso 1 1 calc R U . . .
C3 C 0.20497(10) 0.62971(13) 0.70976(10) 0.0188(3) Uani 1 1 d . . . . .
C3' C 0.58958(10) 0.19890(14) 0.48554(10) 0.0184(3) Uani 1 1 d . . . . .
C4 C 0.30008(10) 0.56087(13) 0.71278(10) 0.0188(3) Uani 1 1 d . . . . .
H4 H 0.347020 0.563658 0.777992 0.023 Uiso 1 1 calc R U . . .
C4' C 0.55107(10) 0.28208(13) 0.56670(10) 0.0190(3) Uani 1 1 d . . . . .
H4' H 0.590885 0.296875 0.635734 0.023 Uiso 1 1 calc R U . . .
C5 C 0.32618(10) 0.48746(13) 0.61912(10) 0.0177(3) Uani 1 1 d . . . . .
C5' C 0.45333(10) 0.34373(13) 0.54585(10) 0.0181(3) Uani 1 1 d . . . . .
C6 C 0.25933(10) 0.47808(14) 0.52272(10) 0.0191(3) Uani 1 1 d . . . . .
C6' C 0.39259(10) 0.32436(14) 0.44625(10) 0.0192(3) Uani 1 1 d . . . . .
C7 C 0.28773(10) 0.39331(14) 0.42412(10) 0.0189(3) Uani 1 1 d . . . . .
O1 O 0.17416(7) 0.70128(10) 0.79904(8) 0.0218(2) Uani 1 1 d . . . . .
O2 O 0.42267(7) 0.42494(10) 0.63142(7) 0.0203(2) Uani 1 1 d . . . . .
O3 O 0.68692(7) 0.14301(10) 0.50895(8) 0.0221(2) Uani 1 1 d . . . . .
O4 O 0.29242(7) 0.49003(9) 0.32563(7) 0.0190(2) Uani 1 1 d . . . . .
O5 O 0.21355(7) 0.51585(10) 0.15378(7) 0.0220(2) Uani 1 1 d . . . . .
C8 C 0.20284(10) 0.29279(13) 0.38152(10) 0.0180(3) Uani 1 1 d . . . . .
C9 C 0.16506(11) 0.17600(14) 0.43406(11) 0.0220(3) Uani 1 1 d . . . . .
H9 H 0.192412 0.149572 0.506715 0.026 Uiso 1 1 calc R U . . .
C10 C 0.08600(11) 0.09928(14) 0.37675(11) 0.0238(3) Uani 1 1 d . . . . .
H10A H 0.058610 0.019264 0.411040 0.029 Uiso 1 1 calc R U . . .
C11 C 0.04578(10) 0.13740(15) 0.26942(12) 0.0234(3) Uani 1 1 d . . . . .
H11 H -0.008440 0.083130 0.232145 0.028 Uiso 1 1 calc R U . . .
C12 C 0.08413(10) 0.25331(14) 0.21697(11) 0.0209(3) Uani 1 1 d . . . . .
H12A H 0.057457 0.279700 0.144076 0.025 Uiso 1 1 calc R U . . .
C13 C 0.16340(10) 0.32971(13) 0.27536(10) 0.0180(3) Uani 1 1 d . . . . .
C14 C 0.22183(10) 0.45321(13) 0.24190(10) 0.0176(3) Uani 1 1 d . . . . .
H5 H 0.2202(16) 0.688(2) 0.8566(18) 0.040(5) Uiso 1 1 d . . . . .
H3 H 0.7110(19) 0.104(3) 0.449(2) 0.056(6) Uiso 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 1.3814(18) . ?
C1 C6 1.4033(18) . ?
C1 H1 0.9500 . ?
C1' C2' 1.3781(19) . ?
C1' C6' 1.4051(18) . ?
C1' H10 0.9500 . ?
C2 C3 1.4040(18) . ?
C2 H2 0.9500 . ?
C2' C3' 1.4013(17) . ?
C2' H2' 0.9500 . ?
C3 O1 1.3616(15) . ?
C3 C4 1.3850(18) . ?
C3' O3 1.3668(15) . ?
C3' C4' 1.3836(17) . ?
C4 C5 1.3938(17) . ?
C4 H4 0.9500 . ?
C4' C5' 1.3902(18) . ?
C4' H4' 0.9500 . ?
C5 O2 1.3724(15) . ?
C5 C6 1.3885(17) . ?
C5' O2 1.3745(15) . ?
C5' C6' 1.3882(17) . ?
C6 C7 1.5081(17) . ?
C6' C7 1.5027(18) . ?
C7 O4 1.5093(14) . ?
C7 C8 1.5096(18) . ?
O1 H5 0.88(2) . ?
O3 H3 0.89(3) . ?
O4 C14 1.3455(15) . ?
O5 C14 1.2159(15) . ?
C8 C13 1.3820(17) . ?
C8 C9 1.3896(18) . ?
C9 C10 1.388(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.400(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.3852(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.3940(18) . ?
C12 H12A 0.9500 . ?
C13 C14 1.4719(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 122.03(12) . . ?
C2 C1 H1 119.0 . . ?
C6 C1 H1 119.0 . . ?
C2' C1' C6' 122.07(12) . . ?
C2' C1' H10 119.0 . . ?
C6' C1' H10 119.0 . . ?
C1 C2 C3 119.47(12) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C1' C2' C3' 118.99(12) . . ?
C1' C2' H2' 120.5 . . ?
C3' C2' H2' 120.5 . . ?
O1 C3 C4 122.13(12) . . ?
O1 C3 C2 118.04(11) . . ?
C4 C3 C2 119.82(12) . . ?
O3 C3' C4' 116.96(11) . . ?
O3 C3' C2' 122.56(11) . . ?
C4' C3' C2' 120.48(12) . . ?
C3 C4 C5 119.28(12) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C3' C4' C5' 119.10(11) . . ?
C3' C4' H4' 120.4 . . ?
C5' C4' H4' 120.4 . . ?
O2 C5 C6 123.48(11) . . ?
O2 C5 C4 114.07(11) . . ?
C6 C5 C4 122.45(12) . . ?
O2 C5' C6' 123.28(11) . . ?
O2 C5' C4' 114.50(11) . . ?
C6' C5' C4' 122.22(12) . . ?
C5 C6 C1 116.90(12) . . ?
C5 C6 C7 121.38(11) . . ?
C1 C6 C7 121.71(11) . . ?
C5' C6' C1' 117.12(12) . . ?
C5' C6' C7 121.68(11) . . ?
C1' C6' C7 121.19(11) . . ?
C6' C7 C6 111.59(10) . . ?
C6' C7 O4 108.23(10) . . ?
C6 C7 O4 108.70(10) . . ?
C6' C7 C8 113.15(11) . . ?
C6 C7 C8 113.15(10) . . ?
O4 C7 C8 101.34(9) . . ?
C3 O1 H5 109.4(14) . . ?
C5 O2 C5' 118.52(10) . . ?
C3' O3 H3 111.7(15) . . ?
C14 O4 C7 111.20(9) . . ?
C13 C8 C9 120.79(12) . . ?
C13 C8 C7 110.54(11) . . ?
C9 C8 C7 128.66(11) . . ?
C10 C9 C8 117.72(12) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
C9 C10 C11 121.36(13) . . ?
C9 C10 H10A 119.3 . . ?
C11 C10 H10A 119.3 . . ?
C12 C11 C10 120.77(13) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 117.38(12) . . ?
C11 C12 H12A 121.3 . . ?
C13 C12 H12A 121.3 . . ?
C8 C13 C12 121.97(12) . . ?
C8 C13 C14 107.61(11) . . ?
C12 C13 C14 130.40(12) . . ?
O5 C14 O4 122.07(12) . . ?
O5 C14 C13 128.62(12) . . ?
O4 C14 C13 109.29(10) . . ?

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 -1.3(2) . . . . ?
C6' C1' C2' C3' -0.1(2) . . . . ?
C1 C2 C3 O1 -177.67(12) . . . . ?
C1 C2 C3 C4 1.8(2) . . . . ?
C1' C2' C3' O3 -178.71(12) . . . . ?
C1' C2' C3' C4' 1.2(2) . . . . ?
O1 C3 C4 C5 178.91(11) . . . . ?
C2 C3 C4 C5 -0.54(19) . . . . ?
O3 C3' C4' C5' 178.65(11) . . . . ?
C2' C3' C4' C5' -1.27(19) . . . . ?
C3 C4 C5 O2 179.29(11) . . . . ?
C3 C4 C5 C6 -1.3(2) . . . . ?
C3' C4' C5' O2 -179.59(11) . . . . ?
C3' C4' C5' C6' 0.2(2) . . . . ?
O2 C5 C6 C1 -178.86(11) . . . . ?
C4 C5 C6 C1 1.78(19) . . . . ?
O2 C5 C6 C7 1.8(2) . . . . ?
C4 C5 C6 C7 -177.59(12) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
C2 C1 C6 C7 178.90(12) . . . . ?
O2 C5' C6' C1' -179.35(11) . . . . ?
C4' C5' C6' C1' 0.87(19) . . . . ?
O2 C5' C6' C7 0.7(2) . . . . ?
C4' C5' C6' C7 -179.09(12) . . . . ?
C2' C1' C6' C5' -0.9(2) . . . . ?
C2' C1' C6' C7 179.01(12) . . . . ?
C5' C6' C7 C6 -1.67(17) . . . . ?
C1' C6' C7 C6 178.38(12) . . . . ?
C5' C6' C7 O4 117.90(12) . . . . ?
C1' C6' C7 O4 -62.05(15) . . . . ?
C5' C6' C7 C8 -130.64(13) . . . . ?
C1' C6' C7 C8 49.41(16) . . . . ?
C5 C6 C7 C6' 0.50(17) . . . . ?
C1 C6 C7 C6' -178.84(12) . . . . ?
C5 C6 C7 O4 -118.78(12) . . . . ?
C1 C6 C7 O4 61.88(15) . . . . ?
C5 C6 C7 C8 129.48(13) . . . . ?
C1 C6 C7 C8 -49.86(16) . . . . ?
C6 C5 O2 C5' -2.87(18) . . . . ?
C4 C5 O2 C5' 176.54(11) . . . . ?
C6' C5' O2 C5 1.61(18) . . . . ?
C4' C5' O2 C5 -178.59(11) . . . . ?
C6' C7 O4 C14 120.02(11) . . . . ?
C6 C7 O4 C14 -118.62(11) . . . . ?
C8 C7 O4 C14 0.79(12) . . . . ?
C6' C7 C8 C13 -117.02(12) . . . . ?
C6 C7 C8 C13 114.81(12) . . . . ?
O4 C7 C8 C13 -1.38(13) . . . . ?
C6' C7 C8 C9 62.15(17) . . . . ?
C6 C7 C8 C9 -66.02(17) . . . . ?
O4 C7 C8 C9 177.78(12) . . . . ?
C13 C8 C9 C10 -0.68(19) . . . . ?
C7 C8 C9 C10 -179.77(12) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C10 C11 C12 C13 -0.23(19) . . . . ?
C9 C8 C13 C12 0.61(19) . . . . ?
C7 C8 C13 C12 179.85(11) . . . . ?
C9 C8 C13 C14 -177.78(11) . . . . ?
C7 C8 C13 C14 1.46(14) . . . . ?
C11 C12 C13 C8 -0.14(19) . . . . ?
C11 C12 C13 C14 177.85(12) . . . . ?
C7 O4 C14 O5 -178.74(11) . . . . ?
C7 O4 C14 C13 0.02(13) . . . . ?
C8 C13 C14 O5 177.72(13) . . . . ?
C12 C13 C14 O5 -0.5(2) . . . . ?
C8 C13 C14 O4 -0.93(14) . . . . ?
C12 C13 C14 O4 -179.14(12) . . . . ?

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
C4' H4' O4 0.95 2.55 3.1649(15) 123.0 3_666 yes
O1 H5 O3 0.88(2) 1.98(2) 2.8560(13) 174(2) 2_656 yes
O3 H3 O5 0.89(3) 1.84(3) 2.7168(13) 167(2) 2_645 yes

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.059



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

data_20240305Pablo
_database_code_depnum_ccdc_archive 'CCDC 2407099'
loop_
_audit_author_name
_audit_author_address
'Sonia Mallet Ladeira'
;Laboratoire de Chimie de Coordination
France
;
_audit_update_record             
;
2024-12-02 deposited with the CCDC.	2025-05-12 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            'C22 H15 N O5'
_chemical_formula_weight         373.35

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                   7.379(5)
_cell_length_b                   15.617(10)
_cell_length_c                   14.777(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.00(2)
_cell_angle_gamma                90
_cell_volume                     1693.4(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6719
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      34.82

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            81375
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.903
_diffrn_reflns_theta_max         35.615
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7495
_reflns_number_gt                6262
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0592P)²+0.6426P] 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         7495
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
O4 O 0.29298(8) 0.74029(4) 0.45639(4) 0.01221(11) Uani 1 1 d . . . . .
O1 O 0.15025(10) 0.97493(4) 0.78110(4) 0.01677(12) Uani 1 1 d . . . . .
H1A H 0.183397 0.949739 0.830282 0.025 Uiso 1 1 calc R U . . .
O2 O 0.23299(9) 0.97382(4) 0.47318(4) 0.01487(12) Uani 1 1 d . . . . .
O5 O 0.29061(10) 0.59754(4) 0.44835(4) 0.01645(12) Uani 1 1 d . . . . .
C4' C 0.29600(12) 0.99675(5) 0.32464(5) 0.01315(13) Uani 1 1 d . . . . .
H4' H 0.225235 1.047573 0.324537 0.016 Uiso 1 1 calc R U . . .
C5 C 0.26388(11) 0.93142(5) 0.55429(5) 0.01124(13) Uani 1 1 d . . . . .
C5' C 0.32085(11) 0.94559(5) 0.40157(5) 0.01136(13) Uani 1 1 d . . . . .
C6 C 0.36121(11) 0.85532(5) 0.56408(5) 0.01072(12) Uani 1 1 d . . . . .
C6' C 0.42226(11) 0.87062(5) 0.40428(5) 0.01105(12) Uani 1 1 d . . . . .
C7 C 0.42666(11) 0.81134(5) 0.48362(5) 0.01064(12) Uani 1 1 d . . . . .
C8 C 0.60129(11) 0.76221(5) 0.50561(5) 0.01150(13) Uani 1 1 d . . . . .
C9 C 0.77526(11) 0.79274(6) 0.53226(6) 0.01500(14) Uani 1 1 d . . . . .
H9 H 0.799407 0.852410 0.537136 0.018 Uiso 1 1 calc R U . . .
C10 C 0.91294(12) 0.73264(6) 0.55155(6) 0.01863(16) Uani 1 1 d . . . . .
H10 H 1.033386 0.751758 0.569958 0.022 Uiso 1 1 calc R U . . .
C11 C 0.87835(13) 0.64478(6) 0.54449(6) 0.01979(17) Uani 1 1 d . . . . .
H11 H 0.975193 0.605282 0.558347 0.024 Uiso 1 1 calc R U . . .
C12 C 0.70454(13) 0.61462(5) 0.51755(6) 0.01601(15) Uani 1 1 d . . . . .
H12 H 0.679626 0.555028 0.512463 0.019 Uiso 1 1 calc R U . . .
C13 C 0.56798(11) 0.67537(5) 0.49824(5) 0.01228(13) Uani 1 1 d . . . . .
C14 C 0.37441(12) 0.66290(5) 0.46642(5) 0.01227(13) Uani 1 1 d . . . . .
C15 C 0.09403(13) 1.23614(6) 0.20799(7) 0.01911(16) Uani 1 1 d . . . . .
C16 C 0.00272(14) 1.31780(6) 0.21286(8) 0.02420(19) Uani 1 1 d . . . . .
H16A H -0.032711 1.339120 0.151172 0.036 Uiso 1 1 calc R U . . .
H16B H 0.085329 1.358899 0.245967 0.036 Uiso 1 1 calc R U . . .
H16C H -0.106270 1.310666 0.244752 0.036 Uiso 1 1 calc R U . . .
O3 O 0.35630(11) 1.01834(4) 0.17049(4) 0.01992(14) Uani 1 1 d . . . . .
H3A H 0.297832 1.063336 0.178702 0.030 Uiso 1 1 calc R U . . .
N1 N 0.16918(13) 1.17277(6) 0.20216(7) 0.02501(17) Uani 1 1 d . . . . .
C1 C 0.38542(12) 0.81926(5) 0.65076(5) 0.01318(13) Uani 1 1 d . . . . .
H1 H 0.452280 0.767422 0.659648 0.016 Uiso 1 1 calc R U . . .
C1' C 0.50306(12) 0.84841(5) 0.32623(5) 0.01307(13) Uani 1 1 d . . . . .
H1' H 0.574553 0.797805 0.326461 0.016 Uiso 1 1 calc R U . . .
C2 C 0.31522(12) 0.85664(5) 0.72379(5) 0.01418(14) Uani 1 1 d . . . . .
H2 H 0.332326 0.830367 0.782043 0.017 Uiso 1 1 calc R U . . .
C2' C 0.48154(12) 0.89814(5) 0.24898(5) 0.01461(14) Uani 1 1 d . . . . .
H2' H 0.538049 0.882015 0.196657 0.018 Uiso 1 1 calc R U . . .
C3 C 0.21845(11) 0.93357(5) 0.71188(5) 0.01248(13) Uani 1 1 d . . . . .
C3' C 0.37600(12) 0.97253(5) 0.24799(5) 0.01370(14) Uani 1 1 d . . . . .
C4 C 0.19150(11) 0.97055(5) 0.62665(5) 0.01287(13) Uani 1 1 d . . . . .
H4 H 0.124103 1.022232 0.617710 0.015 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
O4 C14 1.3510(12) . ?
O4 C7 1.5110(12) . ?
O1 C3 1.3507(11) . ?
O1 H1A 0.8400 . ?
O2 C5 1.3674(12) . ?
O2 C5' 1.3703(12) . ?
O5 C14 1.2087(11) . ?
C4' C3' 1.3836(13) . ?
C4' C5' 1.3858(12) . ?
C4' H4' 0.9500 . ?
C5 C4 1.3862(13) . ?
C5 C6 1.3883(13) . ?
C5' C6' 1.3879(13) . ?
C6 C1 1.3935(13) . ?
C6 C7 1.4960(13) . ?
C6' C1' 1.3963(13) . ?
C6' C7 1.4915(13) . ?
C7 C8 1.5057(13) . ?
C8 C13 1.3806(14) . ?
C8 C9 1.3873(14) . ?
C9 C10 1.3906(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.3974(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3851(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3916(13) . ?
C12 H12 0.9500 . ?
C13 C14 1.4693(15) . ?
C15 N1 1.1421(14) . ?
C15 C16 1.4476(15) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O3 C3' 1.3452(12) . ?
O3 H3A 0.8400 . ?
C1 C2 1.3749(13) . ?
C1 H1 0.9500 . ?
C1' C2' 1.3759(13) . ?
C1' H1' 0.9500 . ?
C2 C3 1.3993(13) . ?
C2 H2 0.9500 . ?
C2' C3' 1.3978(13) . ?
C2' H2' 0.9500 . ?
C3 C4 1.3808(13) . ?
C4 H4 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O4 C7 110.94(8) . . ?
C3 O1 H1A 109.5 . . ?
C5 O2 C5' 118.17(7) . . ?
C3' C4' C5' 118.87(8) . . ?
C3' C4' H4' 120.6 . . ?
C5' C4' H4' 120.6 . . ?
O2 C5 C4 114.85(8) . . ?
O2 C5 C6 122.88(7) . . ?
C4 C5 C6 122.27(7) . . ?
O2 C5' C4' 114.54(8) . . ?
O2 C5' C6' 123.12(7) . . ?
C4' C5' C6' 122.32(8) . . ?
C5 C6 C1 117.18(7) . . ?
C5 C6 C7 121.10(7) . . ?
C1 C6 C7 121.60(8) . . ?
C5' C6' C1' 117.46(7) . . ?
C5' C6' C7 120.90(7) . . ?
C1' C6' C7 121.27(8) . . ?
C6' C7 C6 110.95(8) . . ?
C6' C7 C8 115.71(7) . . ?
C6 C7 C8 113.73(7) . . ?
C6' C7 O4 106.65(7) . . ?
C6 C7 O4 107.02(7) . . ?
C8 C7 O4 101.73(7) . . ?
C13 C8 C9 120.79(8) . . ?
C13 C8 C7 110.02(8) . . ?
C9 C8 C7 129.17(8) . . ?
C8 C9 C10 117.43(9) . . ?
C8 C9 H9 121.3 . . ?
C10 C9 H9 121.3 . . ?
C9 C10 C11 121.57(9) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C10 120.78(8) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 117.12(9) . . ?
C11 C12 H12 121.4 . . ?
C13 C12 H12 121.4 . . ?
C8 C13 C12 122.30(9) . . ?
C8 C13 C14 108.33(7) . . ?
C12 C13 C14 129.35(8) . . ?
O5 C14 O4 121.33(9) . . ?
O5 C14 C13 129.82(8) . . ?
O4 C14 C13 108.84(7) . . ?
N1 C15 C16 177.87(11) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3' O3 H3A 109.5 . . ?
C2 C1 C6 121.82(8) . . ?
C2 C1 H1 119.1 . . ?
C6 C1 H1 119.1 . . ?
C2' C1' C6' 121.52(8) . . ?
C2' C1' H1' 119.2 . . ?
C6' C1' H1' 119.2 . . ?
C1 C2 C3 119.67(8) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C1' C2' C3' 119.58(8) . . ?
C1' C2' H2' 120.2 . . ?
C3' C2' H2' 120.2 . . ?
O1 C3 C4 117.46(8) . . ?
O1 C3 C2 122.75(8) . . ?
C4 C3 C2 119.78(7) . . ?
O3 C3' C4' 122.28(8) . . ?
O3 C3' C2' 117.49(8) . . ?
C4' C3' C2' 120.23(7) . . ?
C3 C4 C5 119.26(8) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?

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
C5' O2 C5 C4 171.26(7) . . . . ?
C5' O2 C5 C6 -8.31(12) . . . . ?
C5 O2 C5' C4' -174.13(7) . . . . ?
C5 O2 C5' C6' 7.72(12) . . . . ?
C3' C4' C5' O2 -178.57(7) . . . . ?
C3' C4' C5' C6' -0.41(13) . . . . ?
O2 C5 C6 C1 179.04(8) . . . . ?
C4 C5 C6 C1 -0.50(12) . . . . ?
O2 C5 C6 C7 -4.76(12) . . . . ?
C4 C5 C6 C7 175.71(8) . . . . ?
O2 C5' C6' C1' 179.15(7) . . . . ?
C4' C5' C6' C1' 1.14(12) . . . . ?
O2 C5' C6' C7 5.96(12) . . . . ?
C4' C5' C6' C7 -172.05(8) . . . . ?
C5' C6' C7 C6 -17.12(10) . . . . ?
C1' C6' C7 C6 169.94(7) . . . . ?
C5' C6' C7 C8 -148.62(7) . . . . ?
C1' C6' C7 C8 38.45(10) . . . . ?
C5' C6' C7 O4 99.08(9) . . . . ?
C1' C6' C7 O4 -73.85(10) . . . . ?
C5 C6 C7 C6' 16.59(10) . . . . ?
C1 C6 C7 C6' -167.37(7) . . . . ?
C5 C6 C7 C8 149.10(7) . . . . ?
C1 C6 C7 C8 -34.87(11) . . . . ?
C5 C6 C7 O4 -99.38(9) . . . . ?
C1 C6 C7 O4 76.66(10) . . . . ?
C14 O4 C7 C6' 124.90(7) . . . . ?
C14 O4 C7 C6 -116.30(7) . . . . ?
C14 O4 C7 C8 3.26(7) . . . . ?
C6' C7 C8 C13 -118.97(8) . . . . ?
C6 C7 C8 C13 110.86(8) . . . . ?
O4 C7 C8 C13 -3.84(8) . . . . ?
C6' C7 C8 C9 62.67(11) . . . . ?
C6 C7 C8 C9 -67.50(11) . . . . ?
O4 C7 C8 C9 177.80(8) . . . . ?
C13 C8 C9 C10 -0.38(12) . . . . ?
C7 C8 C9 C10 177.82(8) . . . . ?
C8 C9 C10 C11 0.01(13) . . . . ?
C9 C10 C11 C12 0.23(14) . . . . ?
C10 C11 C12 C13 -0.08(13) . . . . ?
C9 C8 C13 C12 0.54(12) . . . . ?
C7 C8 C13 C12 -177.98(7) . . . . ?
C9 C8 C13 C14 -178.35(7) . . . . ?
C7 C8 C13 C14 3.14(9) . . . . ?
C11 C12 C13 C8 -0.30(12) . . . . ?
C11 C12 C13 C14 178.34(8) . . . . ?
C7 O4 C14 O5 179.89(7) . . . . ?
C7 O4 C14 C13 -1.59(8) . . . . ?
C8 C13 C14 O5 177.37(8) . . . . ?
C12 C13 C14 O5 -1.41(14) . . . . ?
C8 C13 C14 O4 -0.98(9) . . . . ?
C12 C13 C14 O4 -179.76(8) . . . . ?
C5 C6 C1 C2 0.48(12) . . . . ?
C7 C6 C1 C2 -175.70(8) . . . . ?
C5' C6' C1' C2' -0.81(12) . . . . ?
C7 C6' C1' C2' 172.35(8) . . . . ?
C6 C1 C2 C3 -0.81(13) . . . . ?
C6' C1' C2' C3' -0.24(13) . . . . ?
C1 C2 C3 O1 -178.12(8) . . . . ?
C1 C2 C3 C4 1.12(13) . . . . ?
C5' C4' C3' O3 179.22(8) . . . . ?
C5' C4' C3' C2' -0.69(13) . . . . ?
C1' C2' C3' O3 -178.91(8) . . . . ?
C1' C2' C3' C4' 1.00(13) . . . . ?
O1 C3 C4 C5 178.15(8) . . . . ?
C2 C3 C4 C5 -1.13(13) . . . . ?
O2 C5 C4 C3 -178.73(7) . . . . ?
C6 C5 C4 C3 0.84(13) . . . . ?

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
O1 H1A O5 0.84 1.98 2.8153(17) 171.7 4_576 yes
C4' H4' N1 0.95 2.67 3.3695(19) 131.3 . yes
O3 H3A N1 0.84 2.00 2.8420(18) 177.2 . yes

_refine_diff_density_max         0.601
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.061



