# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_3f
_database_code_depnum_ccdc_archive 'CCDC 2026167'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2020-08-30 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 O6'
_chemical_formula_sum            'C14 H12 O6'
_chemical_formula_weight         276.24

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   10.6953(2)
_cell_length_b                   10.0575(2)
_cell_length_c                   11.2520(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.4540(10)
_cell_angle_gamma                90
_cell_volume                     1110.36(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6677
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      32.57

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10. 
;

_exptl_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            12197
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.008
_diffrn_reflns_theta_max         32.579
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4021
_reflns_number_gt                3854
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.993
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.988

_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, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'

_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)+(0.0425P)²+0.2749P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_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 1819 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.2(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4021
_refine_ls_number_parameters     181
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0752
_refine_ls_wR_factor_gt          0.0739
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.67120(15) 0.64091(14) 0.51358(14) 0.0123(2) Uani 1 1 d . . . . .
H1A H 0.7038 0.6991 0.5910 0.015 Uiso 1 1 calc R U . . .
H1B H 0.7491 0.5864 0.5156 0.015 Uiso 1 1 calc R U . . .
O2 O 0.62310(11) 0.72175(10) 0.39879(11) 0.0134(2) Uani 1 1 d . . . . .
C3 C 0.51284(16) 0.80710(14) 0.39023(16) 0.0135(2) Uani 1 1 d . . . . .
H3A H 0.4862 0.8623 0.3111 0.016 Uiso 1 1 calc R U . . .
H3B H 0.5430 0.8674 0.4660 0.016 Uiso 1 1 calc R U . . .
C3A C 0.39176(14) 0.72812(13) 0.38610(13) 0.0103(2) Uani 1 1 d . . . . .
C4 C 0.26265(15) 0.79580(14) 0.38086(14) 0.0127(2) Uani 1 1 d . . . . .
H4 H 0.2539 0.8839 0.4071 0.015 Uiso 1 1 calc R U . . .
C5 C 0.16390(16) 0.70510(15) 0.33148(14) 0.0137(3) Uani 1 1 d . . . . .
H5 H 0.0704 0.7150 0.3163 0.016 Uiso 1 1 calc R U . . .
C6 C 0.23216(14) 0.58283(15) 0.30470(14) 0.0117(2) Uani 1 1 d . . . . .
H6 H 0.1700 0.5210 0.2375 0.014 Uiso 1 1 calc R U . . .
O6 O 0.33788(10) 0.64317(10) 0.27346(10) 0.01103(19) Uani 1 1 d . . . . .
C6A C 0.31648(14) 0.51805(13) 0.43862(13) 0.0100(2) Uani 1 1 d . . . . .
H6A H 0.2614 0.5018 0.4911 0.012 Uiso 1 1 calc R U . . .
C7 C 0.40541(14) 0.39845(13) 0.43729(13) 0.0100(2) Uani 1 1 d . . . . .
H7 H 0.3552 0.3267 0.3751 0.012 Uiso 1 1 calc R U . . .
O7 O 0.51749(10) 0.45492(10) 0.41359(9) 0.00985(18) Uani 1 1 d . . . . .
C7A C 0.47871(15) 0.35101(14) 0.57905(13) 0.0109(2) Uani 1 1 d . . . . .
H7A H 0.4159 0.3448 0.6251 0.013 Uiso 1 1 calc R U . . .
C8 C 0.55768(16) 0.22464(15) 0.58836(14) 0.0139(3) Uani 1 1 d . . . . .
O8 O 0.51663(14) 0.11489(11) 0.55437(12) 0.0199(2) Uani 1 1 d . . . . .
O9 O 0.69698(12) 0.24918(11) 0.64564(11) 0.0150(2) Uani 1 1 d . . . . .
C10 C 0.72207(16) 0.38318(15) 0.67672(15) 0.0152(3) Uani 1 1 d . . . . .
O10 O 0.83617(13) 0.42234(13) 0.72617(14) 0.0246(3) Uani 1 1 d . . . . .
C10A C 0.58958(14) 0.45840(14) 0.63729(13) 0.0115(2) Uani 1 1 d . . . . .
H10A H 0.5812 0.5061 0.7117 0.014 Uiso 1 1 calc R U . . .
C10B C 0.56007(14) 0.55039(13) 0.51828(13) 0.0095(2) Uani 1 1 d . . . . .
C10C C 0.42864(14) 0.62574(14) 0.49882(13) 0.0093(2) Uani 1 1 d . . . . .
H10C H 0.4291 0.6650 0.5806 0.011 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
C1 O2 1.4370(18) . ?
C1 C10B 1.515(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
O2 C3 1.4305(18) . ?
C3 C3A 1.504(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A O6 1.4447(17) . ?
C3A C4 1.519(2) . ?
C3A C10C 1.5576(19) . ?
C4 C5 1.338(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.520(2) . ?
C5 H5 0.9500 . ?
C6 O6 1.4445(17) . ?
C6 C6A 1.5578(19) . ?
C6 H6 1.0000 . ?
C6A C7 1.5372(19) . ?
C6A C10C 1.5569(19) . ?
C6A H6A 1.0000 . ?
C7 O7 1.4439(17) . ?
C7 C7A 1.5464(19) . ?
C7 H7 1.0000 . ?
O7 C10B 1.4457(16) . ?
C7A C8 1.506(2) . ?
C7A C10A 1.544(2) . ?
C7A H7A 1.0000 . ?
C8 O8 1.1932(19) . ?
C8 O9 1.3898(19) . ?
O9 C10 1.3913(19) . ?
C10 O10 1.189(2) . ?
C10 C10A 1.509(2) . ?
C10A C10B 1.553(2) . ?
C10A H10A 1.0000 . ?
C10B C10C 1.5340(19) . ?
C10C H10C 1.0000 . ?

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
O2 C1 C10B 111.49(11) . . ?
O2 C1 H1A 109.3 . . ?
C10B C1 H1A 109.3 . . ?
O2 C1 H1B 109.3 . . ?
C10B C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C3 O2 C1 112.99(11) . . ?
O2 C3 C3A 111.21(11) . . ?
O2 C3 H3A 109.4 . . ?
C3A C3 H3A 109.4 . . ?
O2 C3 H3B 109.4 . . ?
C3A C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O6 C3A C3 112.16(12) . . ?
O6 C3A C4 101.06(11) . . ?
C3 C3A C4 121.51(11) . . ?
O6 C3A C10C 101.93(10) . . ?
C3 C3A C10C 112.83(11) . . ?
C4 C3A C10C 105.04(11) . . ?
C5 C4 C3A 105.41(12) . . ?
C5 C4 H4 127.3 . . ?
C3A C4 H4 127.3 . . ?
C4 C5 C6 105.77(13) . . ?
C4 C5 H5 127.1 . . ?
C6 C5 H5 127.1 . . ?
O6 C6 C5 101.11(12) . . ?
O6 C6 C6A 101.73(10) . . ?
C5 C6 C6A 106.58(11) . . ?
O6 C6 H6 115.2 . . ?
C5 C6 H6 115.2 . . ?
C6A C6 H6 115.2 . . ?
C6 O6 C3A 96.46(10) . . ?
C7 C6A C10C 100.14(10) . . ?
C7 C6A C6 116.11(11) . . ?
C10C C6A C6 100.31(10) . . ?
C7 C6A H6A 112.9 . . ?
C10C C6A H6A 112.9 . . ?
C6 C6A H6A 112.9 . . ?
O7 C7 C6A 104.85(10) . . ?
O7 C7 C7A 101.22(11) . . ?
C6A C7 C7A 107.04(11) . . ?
O7 C7 H7 114.2 . . ?
C6A C7 H7 114.2 . . ?
C7A C7 H7 114.2 . . ?
C7 O7 C10B 97.25(10) . . ?
C8 C7A C10A 104.24(12) . . ?
C8 C7A C7 111.84(12) . . ?
C10A C7A C7 102.14(11) . . ?
C8 C7A H7A 112.6 . . ?
C10A C7A H7A 112.6 . . ?
C7 C7A H7A 112.6 . . ?
O8 C8 O9 120.18(14) . . ?
O8 C8 C7A 129.31(15) . . ?
O9 C8 C7A 110.50(13) . . ?
C8 O9 C10 110.64(12) . . ?
O10 C10 O9 119.86(14) . . ?
O10 C10 C10A 129.82(15) . . ?
O9 C10 C10A 110.31(13) . . ?
C10 C10A C7A 104.29(12) . . ?
C10 C10A C10B 113.39(12) . . ?
C7A C10A C10B 101.11(11) . . ?
C10 C10A H10A 112.4 . . ?
C7A C10A H10A 112.4 . . ?
C10B C10A H10A 112.4 . . ?
O7 C10B C1 111.58(11) . . ?
O7 C10B C10C 103.78(10) . . ?
C1 C10B C10C 112.66(11) . . ?
O7 C10B C10A 101.35(10) . . ?
C1 C10B C10A 119.68(12) . . ?
C10C C10B C10A 106.12(11) . . ?
C10B C10C C6A 102.82(11) . . ?
C10B C10C C3A 111.32(11) . . ?
C6A C10C C3A 101.77(10) . . ?
C10B C10C H10C 113.3 . . ?
C6A C10C H10C 113.3 . . ?
C3A C10C H10C 113.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10B C1 O2 C3 60.84(15) . . . . ?
C1 O2 C3 C3A -60.96(16) . . . . ?
O2 C3 C3A O6 -62.25(15) . . . . ?
O2 C3 C3A C4 178.23(12) . . . . ?
O2 C3 C3A C10C 52.19(16) . . . . ?
O6 C3A C4 C5 33.16(14) . . . . ?
C3 C3A C4 C5 157.96(14) . . . . ?
C10C C3A C4 C5 -72.54(14) . . . . ?
C3A C4 C5 C6 -0.82(15) . . . . ?
C4 C5 C6 O6 -31.77(14) . . . . ?
C4 C5 C6 C6A 74.17(15) . . . . ?
C5 C6 O6 C3A 50.62(12) . . . . ?
C6A C6 O6 C3A -59.12(11) . . . . ?
C3 C3A O6 C6 177.92(11) . . . . ?
C4 C3A O6 C6 -51.19(12) . . . . ?
C10C C3A O6 C6 56.96(12) . . . . ?
O6 C6 C6A C7 -69.33(13) . . . . ?
C5 C6 C6A C7 -174.82(11) . . . . ?
O6 C6 C6A C10C 37.44(12) . . . . ?
C5 C6 C6A C10C -68.05(14) . . . . ?
C10C C6A C7 O7 -33.78(12) . . . . ?
C6 C6A C7 O7 73.09(14) . . . . ?
C10C C6A C7 C7A 73.19(12) . . . . ?
C6 C6A C7 C7A -179.94(11) . . . . ?
C6A C7 O7 C10B 53.93(12) . . . . ?
C7A C7 O7 C10B -57.27(11) . . . . ?
O7 C7 C7A C8 -76.57(13) . . . . ?
C6A C7 C7A C8 173.91(12) . . . . ?
O7 C7 C7A C10A 34.37(12) . . . . ?
C6A C7 C7A C10A -75.15(13) . . . . ?
C10A C7A C8 O8 -179.09(16) . . . . ?
C7 C7A C8 O8 -69.5(2) . . . . ?
C10A C7A C8 O9 0.79(15) . . . . ?
C7 C7A C8 O9 110.40(13) . . . . ?
O8 C8 O9 C10 179.58(14) . . . . ?
C7A C8 O9 C10 -0.31(16) . . . . ?
C8 O9 C10 O10 -179.68(15) . . . . ?
C8 O9 C10 C10A -0.33(16) . . . . ?
O10 C10 C10A C7A -179.93(18) . . . . ?
O9 C10 C10A C7A 0.80(15) . . . . ?
O10 C10 C10A C10B 71.0(2) . . . . ?
O9 C10 C10A C10B -108.27(14) . . . . ?
C8 C7A C10A C10 -0.92(14) . . . . ?
C7 C7A C10A C10 -117.49(12) . . . . ?
C8 C7A C10A C10B 116.95(12) . . . . ?
C7 C7A C10A C10B 0.38(13) . . . . ?
C7 O7 C10B C1 -173.79(11) . . . . ?
C7 O7 C10B C10C -52.22(12) . . . . ?
C7 O7 C10B C10A 57.71(11) . . . . ?
O2 C1 C10B O7 64.29(15) . . . . ?
O2 C1 C10B C10C -51.99(15) . . . . ?
O2 C1 C10B C10A -177.73(11) . . . . ?
C10 C10A C10B O7 76.03(14) . . . . ?
C7A C10A C10B O7 -35.00(13) . . . . ?
C10 C10A C10B C1 -47.08(17) . . . . ?
C7A C10A C10B C1 -158.11(12) . . . . ?
C10 C10A C10B C10C -175.85(11) . . . . ?
C7A C10A C10B C10C 73.12(12) . . . . ?
O7 C10B C10C C6A 31.47(13) . . . . ?
C1 C10B C10C C6A 152.32(11) . . . . ?
C10A C10B C10C C6A -74.91(12) . . . . ?
O7 C10B C10C C3A -76.80(13) . . . . ?
C1 C10B C10C C3A 44.05(15) . . . . ?
C10A C10B C10C C3A 176.83(10) . . . . ?
C7 C6A C10C C10B 1.18(13) . . . . ?
C6 C6A C10C C10B -117.96(11) . . . . ?
C7 C6A C10C C3A 116.54(11) . . . . ?
C6 C6A C10C C3A -2.60(13) . . . . ?
O6 C3A C10C C10B 76.08(13) . . . . ?
C3 C3A C10C C10B -44.41(15) . . . . ?
C4 C3A C10C C10B -178.86(11) . . . . ?
O6 C3A C10C C6A -32.87(13) . . . . ?
C3 C3A C10C C6A -153.35(11) . . . . ?
C4 C3A C10C C6A 72.20(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
C1 H1A O6 0.99 2.54 3.5064(17) 165.5 4_565
C6 H6 O8 1.00 2.47 3.4690(18) 174.0 4_454
C7 H7 O9 1.00 2.58 3.4814(18) 150.5 4_454
C7A H7A O6 1.00 2.15 3.1113(17) 161.5 2_565

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_10c_sq
_database_code_depnum_ccdc_archive 'CCDC 2026171'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2020-08-30 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 N2 O6'
_chemical_formula_sum            'C24 H24 N2 O6'
_chemical_formula_weight         436.45

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                   32.910(4)
_cell_length_b                   5.5297(7)
_cell_length_c                   26.685(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.912(3)
_cell_angle_gamma                90
_cell_volume                     4646.2(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3194
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      22.12

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28546
_diffrn_reflns_av_unetI/netI     0.0924
_diffrn_reflns_av_R_equivalents  0.1058
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.587
_diffrn_reflns_theta_max         26.357
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4692
_reflns_number_gt                2547
_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. 
  
 Structure factors included contributions from the .fab file. 
  
 _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, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'

_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0605P)²+5.09P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4692
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1329
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1667
_refine_ls_wR_factor_gt          0.1332
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.39171(10) 0.5637(6) 0.42355(11) 0.0323(7) Uani 1 1 d . . . . .
H1A H 0.4085 0.4203 0.4196 0.039 Uiso 1 1 calc R U . . .
H1B H 0.3720 0.6036 0.3887 0.039 Uiso 1 1 calc R U . . .
N2 N 0.42003(8) 0.7670(5) 0.44284(9) 0.0328(6) Uani 1 1 d . . . . .
C3 C 0.45015(10) 0.7319(6) 0.49482(11) 0.0328(7) Uani 1 1 d . . . . .
H3A H 0.4675 0.8799 0.5048 0.039 Uiso 1 1 calc R U . . .
H3B H 0.4695 0.5972 0.4931 0.039 Uiso 1 1 calc R U . . .
C3A C 0.42869(10) 0.6759(6) 0.53716(11) 0.0318(7) Uani 1 1 d . . . . .
O4 O 0.40841(7) 0.8961(4) 0.54711(7) 0.0329(5) Uani 1 1 d . . . . .
C5 C 0.37438(10) 0.8327(6) 0.56864(11) 0.0341(8) Uani 1 1 d . . . . .
H5 H 0.3507 0.9506 0.5551 0.041 Uiso 1 1 calc R U . . .
C5A C 0.35878(10) 0.5824(6) 0.54667(11) 0.0318(7) Uani 1 1 d . . . . .
H5A H 0.3553 0.4681 0.5742 0.038 Uiso 1 1 calc R U . . .
C6 C 0.31895(10) 0.5987(6) 0.49940(11) 0.0310(7) Uani 1 1 d . . . . .
H6 H 0.2957 0.6984 0.5060 0.037 Uiso 1 1 calc R U . . .
O6 O 0.33579(7) 0.6972(4) 0.45945(7) 0.0306(5) Uani 1 1 d . . . . .
C6A C 0.30456(10) 0.3469(6) 0.47758(11) 0.0323(7) Uani 1 1 d . . . . .
H6A H 0.3033 0.2295 0.5056 0.039 Uiso 1 1 calc R U . . .
C7 C 0.26372(11) 0.3569(6) 0.43374(11) 0.0334(7) Uani 1 1 d . . . . .
O7 O 0.22931(7) 0.4223(4) 0.43647(8) 0.0403(6) Uani 1 1 d . . . . .
N8 N 0.27134(8) 0.2744(4) 0.38794(9) 0.0325(6) Uani 1 1 d . . . . .
C9 C 0.31457(11) 0.2391(5) 0.39417(11) 0.0332(7) Uani 1 1 d . . . . .
O9 O 0.32896(7) 0.1874(4) 0.35866(8) 0.0421(6) Uani 1 1 d . . . . .
C9A C 0.33882(10) 0.2781(5) 0.45065(11) 0.0315(7) Uani 1 1 d . . . . .
H9A H 0.3551 0.1309 0.4667 0.038 Uiso 1 1 calc R U . . .
C9B C 0.36658(10) 0.5069(5) 0.46122(11) 0.0300(7) Uani 1 1 d . . . . .
C9C C 0.39218(10) 0.4947(6) 0.51993(10) 0.0311(7) Uani 1 1 d . . . . .
H9C H 0.4019 0.3262 0.5308 0.037 Uiso 1 1 calc R U . . .
C10 C 0.43084(11) 0.9274(6) 0.41048(11) 0.0336(7) Uani 1 1 d . . . . .
O10 O 0.45690(7) 1.0867(4) 0.42456(8) 0.0383(6) Uani 1 1 d . . . . .
O11 O 0.40887(7) 0.8870(4) 0.35971(7) 0.0382(6) Uani 1 1 d . . . . .
C11 C 0.41513(12) 1.0699(7) 0.32387(12) 0.0483(9) Uani 1 1 d . . . . .
H11A H 0.3984 1.0287 0.2881 0.072 Uiso 1 1 calc R U . . .
H11B H 0.4453 1.0774 0.3257 0.072 Uiso 1 1 calc R U . . .
H11C H 0.4060 1.2273 0.3335 0.072 Uiso 1 1 calc R U . . .
C12 C 0.46345(10) 0.6055(6) 0.58579(11) 0.0340(7) Uani 1 1 d . . . . .
H12 H 0.4799 0.7339 0.6052 0.041 Uiso 1 1 calc R U . . .
C13 C 0.47344(11) 0.3863(6) 0.60425(13) 0.0452(9) Uani 1 1 d . . . . .
H13A H 0.4580 0.2510 0.5864 0.054 Uiso 1 1 calc R U . . .
H13B H 0.4961 0.3630 0.6354 0.054 Uiso 1 1 calc R U . . .
C14 C 0.38838(11) 0.8471(6) 0.62722(12) 0.0404(8) Uani 1 1 d . . . . .
H14 H 0.4113 0.7469 0.6457 0.048 Uiso 1 1 calc R U . . .
C15 C 0.37123(12) 0.9879(7) 0.65460(12) 0.0481(9) Uani 1 1 d . . . . .
H15A H 0.3482 1.0904 0.6374 0.058 Uiso 1 1 calc R U . . .
H15B H 0.3817 0.9879 0.6917 0.058 Uiso 1 1 calc R U . . .
C16 C 0.23884(10) 0.2427(6) 0.33925(11) 0.0329(7) Uani 1 1 d . . . . .
C17 C 0.21248(11) 0.0428(6) 0.33287(12) 0.0397(8) Uani 1 1 d . . . . .
H17 H 0.2157 -0.0708 0.3605 0.048 Uiso 1 1 calc R U . . .
C18 C 0.18134(12) 0.0112(7) 0.28562(14) 0.0491(9) Uani 1 1 d . . . . .
H18 H 0.1630 -0.1249 0.2807 0.059 Uiso 1 1 calc R U . . .
C19 C 0.17684(12) 0.1758(7) 0.24571(13) 0.0469(9) Uani 1 1 d . . . . .
H19 H 0.1555 0.1519 0.2134 0.056 Uiso 1 1 calc R U . . .
C20 C 0.20295(12) 0.3743(7) 0.25230(13) 0.0470(9) Uani 1 1 d . . . . .
H20 H 0.1996 0.4875 0.2246 0.056 Uiso 1 1 calc R U . . .
C21 C 0.23431(11) 0.4096(6) 0.29950(12) 0.0386(8) Uani 1 1 d . . . . .
H21 H 0.2524 0.5468 0.3043 0.046 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
C1 N2 1.456(4) . ?
C1 C9B 1.509(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C10 1.356(4) . ?
N2 C3 1.464(4) . ?
C3 C3A 1.528(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A O4 1.450(4) . ?
C3A C12 1.510(4) . ?
C3A C9C 1.529(4) . ?
O4 C5 1.443(4) . ?
C5 C14 1.498(4) . ?
C5 C5A 1.532(4) . ?
C5 H5 1.0000 . ?
C5A C6 1.535(4) . ?
C5A C9C 1.552(4) . ?
C5A H5A 1.0000 . ?
C6 O6 1.444(3) . ?
C6 C6A 1.530(4) . ?
C6 H6 1.0000 . ?
O6 C9B 1.452(3) . ?
C6A C7 1.504(4) . ?
C6A C9A 1.550(4) . ?
C6A H6A 1.0000 . ?
C7 O7 1.211(4) . ?
C7 N8 1.394(4) . ?
N8 C9 1.397(4) . ?
N8 C16 1.433(4) . ?
C9 O9 1.211(3) . ?
C9 C9A 1.502(4) . ?
C9A C9B 1.538(4) . ?
C9A H9A 1.0000 . ?
C9B C9C 1.549(4) . ?
C9C H9C 1.0000 . ?
C10 O10 1.211(4) . ?
C10 O11 1.356(3) . ?
O11 C11 1.447(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.314(4) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9500 . ?
C13 H13B 0.9500 . ?
C14 C15 1.303(4) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9500 . ?
C15 H15B 0.9500 . ?
C16 C21 1.381(4) . ?
C16 C17 1.385(4) . ?
C17 C18 1.385(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.373(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.390(5) . ?
C20 H20 0.9500 . ?
C21 H21 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
N2 C1 C9B 110.1(2) . . ?
N2 C1 H1A 109.6 . . ?
C9B C1 H1A 109.6 . . ?
N2 C1 H1B 109.6 . . ?
C9B C1 H1B 109.6 . . ?
H1A C1 H1B 108.2 . . ?
C10 N2 C1 122.7(2) . . ?
C10 N2 C3 117.4(3) . . ?
C1 N2 C3 114.8(2) . . ?
N2 C3 C3A 113.3(3) . . ?
N2 C3 H3A 108.9 . . ?
C3A C3 H3A 108.9 . . ?
N2 C3 H3B 108.9 . . ?
C3A C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
O4 C3A C12 109.5(2) . . ?
O4 C3A C3 107.6(2) . . ?
C12 C3A C3 106.9(3) . . ?
O4 C3A C9C 104.0(2) . . ?
C12 C3A C9C 115.0(3) . . ?
C3 C3A C9C 113.7(2) . . ?
C5 O4 C3A 108.7(2) . . ?
O4 C5 C14 111.3(3) . . ?
O4 C5 C5A 106.3(2) . . ?
C14 C5 C5A 114.5(3) . . ?
O4 C5 H5 108.2 . . ?
C14 C5 H5 108.2 . . ?
C5A C5 H5 108.2 . . ?
C5 C5A C6 111.9(3) . . ?
C5 C5A C9C 104.8(2) . . ?
C6 C5A C9C 101.0(2) . . ?
C5 C5A H5A 112.8 . . ?
C6 C5A H5A 112.8 . . ?
C9C C5A H5A 112.8 . . ?
O6 C6 C6A 101.8(2) . . ?
O6 C6 C5A 102.1(2) . . ?
C6A C6 C5A 110.8(3) . . ?
O6 C6 H6 113.6 . . ?
C6A C6 H6 113.6 . . ?
C5A C6 H6 113.6 . . ?
C6 O6 C9B 96.7(2) . . ?
C7 C6A C6 111.7(3) . . ?
C7 C6A C9A 104.7(2) . . ?
C6 C6A C9A 102.3(2) . . ?
C7 C6A H6A 112.5 . . ?
C6 C6A H6A 112.5 . . ?
C9A C6A H6A 112.5 . . ?
O7 C7 N8 124.1(3) . . ?
O7 C7 C6A 127.1(3) . . ?
N8 C7 C6A 108.8(3) . . ?
C7 N8 C9 112.2(2) . . ?
C7 N8 C16 123.9(3) . . ?
C9 N8 C16 123.8(2) . . ?
O9 C9 N8 123.8(3) . . ?
O9 C9 C9A 127.2(3) . . ?
N8 C9 C9A 109.0(2) . . ?
C9 C9A C9B 114.6(2) . . ?
C9 C9A C6A 104.7(3) . . ?
C9B C9A C6A 100.8(2) . . ?
C9 C9A H9A 112.0 . . ?
C9B C9A H9A 112.0 . . ?
C6A C9A H9A 112.0 . . ?
O6 C9B C1 109.9(2) . . ?
O6 C9B C9A 102.6(2) . . ?
C1 C9B C9A 117.4(2) . . ?
O6 C9B C9C 103.5(2) . . ?
C1 C9B C9C 116.2(3) . . ?
C9A C9B C9C 105.6(2) . . ?
C3A C9C C9B 115.1(2) . . ?
C3A C9C C5A 104.9(2) . . ?
C9B C9C C5A 101.6(2) . . ?
C3A C9C H9C 111.5 . . ?
C9B C9C H9C 111.5 . . ?
C5A C9C H9C 111.5 . . ?
O10 C10 O11 123.6(3) . . ?
O10 C10 N2 124.9(3) . . ?
O11 C10 N2 111.5(3) . . ?
C10 O11 C11 114.1(3) . . ?
O11 C11 H11A 109.5 . . ?
O11 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O11 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C3A 127.2(3) . . ?
C13 C12 H12 116.4 . . ?
C3A C12 H12 116.4 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C15 C14 C5 124.4(3) . . ?
C15 C14 H14 117.8 . . ?
C5 C14 H14 117.8 . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C21 C16 C17 121.0(3) . . ?
C21 C16 N8 120.0(3) . . ?
C17 C16 N8 119.0(3) . . ?
C16 C17 C18 118.9(3) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C19 C18 C17 120.4(4) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.0(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 119.2(3) . . ?
C16 C21 H21 120.4 . . ?
C20 C21 H21 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
C9B C1 N2 C10 -148.1(3) . . . . ?
C9B C1 N2 C3 58.0(3) . . . . ?
C10 N2 C3 C3A 147.1(3) . . . . ?
C1 N2 C3 C3A -57.5(3) . . . . ?
N2 C3 C3A O4 -71.5(3) . . . . ?
N2 C3 C3A C12 171.1(3) . . . . ?
N2 C3 C3A C9C 43.1(4) . . . . ?
C12 C3A O4 C5 -88.1(3) . . . . ?
C3 C3A O4 C5 156.2(2) . . . . ?
C9C C3A O4 C5 35.3(3) . . . . ?
C3A O4 C5 C14 96.6(3) . . . . ?
C3A O4 C5 C5A -28.7(3) . . . . ?
O4 C5 C5A C6 -98.4(3) . . . . ?
C14 C5 C5A C6 138.3(3) . . . . ?
O4 C5 C5A C9C 10.1(3) . . . . ?
C14 C5 C5A C9C -113.2(3) . . . . ?
C5 C5A C6 O6 71.1(3) . . . . ?
C9C C5A C6 O6 -39.9(3) . . . . ?
C5 C5A C6 C6A 178.9(2) . . . . ?
C9C C5A C6 C6A 67.9(3) . . . . ?
C6A C6 O6 C9B -56.6(3) . . . . ?
C5A C6 O6 C9B 58.0(3) . . . . ?
O6 C6 C6A C7 -76.3(3) . . . . ?
C5A C6 C6A C7 175.8(2) . . . . ?
O6 C6 C6A C9A 35.3(3) . . . . ?
C5A C6 C6A C9A -72.7(3) . . . . ?
C6 C6A C7 O7 -63.8(4) . . . . ?
C9A C6A C7 O7 -173.8(3) . . . . ?
C6 C6A C7 N8 116.9(3) . . . . ?
C9A C6A C7 N8 6.9(3) . . . . ?
O7 C7 N8 C9 172.6(3) . . . . ?
C6A C7 N8 C9 -8.1(3) . . . . ?
O7 C7 N8 C16 -4.0(5) . . . . ?
C6A C7 N8 C16 175.3(3) . . . . ?
C7 N8 C9 O9 -173.7(3) . . . . ?
C16 N8 C9 O9 2.9(5) . . . . ?
C7 N8 C9 C9A 5.8(3) . . . . ?
C16 N8 C9 C9A -177.6(3) . . . . ?
O9 C9 C9A C9B 68.9(4) . . . . ?
N8 C9 C9A C9B -110.6(3) . . . . ?
O9 C9 C9A C6A 178.3(3) . . . . ?
N8 C9 C9A C6A -1.1(3) . . . . ?
C7 C6A C9A C9 -3.4(3) . . . . ?
C6 C6A C9A C9 -120.1(2) . . . . ?
C7 C6A C9A C9B 115.8(3) . . . . ?
C6 C6A C9A C9B -0.9(3) . . . . ?
C6 O6 C9B C1 -177.9(2) . . . . ?
C6 O6 C9B C9A 56.4(2) . . . . ?
C6 O6 C9B C9C -53.2(3) . . . . ?
N2 C1 C9B O6 70.4(3) . . . . ?
N2 C1 C9B C9A -172.9(3) . . . . ?
N2 C1 C9B C9C -46.6(4) . . . . ?
C9 C9A C9B O6 78.2(3) . . . . ?
C6A C9A C9B O6 -33.6(3) . . . . ?
C9 C9A C9B C1 -42.4(4) . . . . ?
C6A C9A C9B C1 -154.2(3) . . . . ?
C9 C9A C9B C9C -173.7(2) . . . . ?
C6A C9A C9B C9C 74.5(3) . . . . ?
O4 C3A C9C C9B 83.6(3) . . . . ?
C12 C3A C9C C9B -156.7(3) . . . . ?
C3 C3A C9C C9B -33.1(4) . . . . ?
O4 C3A C9C C5A -27.2(3) . . . . ?
C12 C3A C9C C5A 92.5(3) . . . . ?
C3 C3A C9C C5A -143.9(3) . . . . ?
O6 C9B C9C C3A -84.5(3) . . . . ?
C1 C9B C9C C3A 36.0(4) . . . . ?
C9A C9B C9C C3A 168.0(2) . . . . ?
O6 C9B C9C C5A 28.2(3) . . . . ?
C1 C9B C9C C5A 148.7(3) . . . . ?
C9A C9B C9C C5A -79.3(3) . . . . ?
C5 C5A C9C C3A 10.5(3) . . . . ?
C6 C5A C9C C3A 126.8(2) . . . . ?
C5 C5A C9C C9B -109.7(3) . . . . ?
C6 C5A C9C C9B 6.6(3) . . . . ?
C1 N2 C10 O10 -173.6(3) . . . . ?
C3 N2 C10 O10 -20.2(5) . . . . ?
C1 N2 C10 O11 6.1(4) . . . . ?
C3 N2 C10 O11 159.4(3) . . . . ?
O10 C10 O11 C11 -7.5(4) . . . . ?
N2 C10 O11 C11 172.8(3) . . . . ?
O4 C3A C12 C13 140.9(3) . . . . ?
C3 C3A C12 C13 -102.9(4) . . . . ?
C9C C3A C12 C13 24.3(5) . . . . ?
O4 C5 C14 C15 120.1(4) . . . . ?
C5A C5 C14 C15 -119.4(4) . . . . ?
C7 N8 C16 C21 103.6(3) . . . . ?
C9 N8 C16 C21 -72.6(4) . . . . ?
C7 N8 C16 C17 -76.7(4) . . . . ?
C9 N8 C16 C17 107.1(4) . . . . ?
C21 C16 C17 C18 0.3(5) . . . . ?
N8 C16 C17 C18 -179.4(3) . . . . ?
C16 C17 C18 C19 0.2(5) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C18 C19 C20 C21 0.3(5) . . . . ?
C17 C16 C21 C20 -0.5(5) . . . . ?
N8 C16 C21 C20 179.2(3) . . . . ?
C19 C20 C21 C16 0.2(5) . . . . ?

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
C1 H1A O10 0.99 2.42 3.395(4) 170.4 1_545
C6A H6A O7 1.00 2.28 3.195(4) 151.1 7_556
C9A H9A O6 1.00 2.47 3.224(4) 131.4 1_545
C9C H9C O4 1.00 2.42 3.397(4) 166.8 1_545

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_6b
_database_code_depnum_ccdc_archive 'CCDC 2026169'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2020-08-30 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H26 N2 O6'
_chemical_formula_sum            'C25 H26 N2 O6'
_chemical_formula_weight         450.48

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.5916(3)
_cell_length_b                   18.4981(5)
_cell_length_c                   13.3949(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.6760(10)
_cell_angle_gamma                90
_cell_volume                     2128.68(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7162
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      32.52

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37982
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.614
_diffrn_reflns_theta_max         32.582
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7728
_reflns_number_gt                5406
_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, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'

_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)+(0.0557P)²+0.9069P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7728
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1335
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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
C1 C 0.58964(16) 0.61392(8) 0.18607(10) 0.0182(2) Uani 1 1 d . . . . .
H1A H 0.6980 0.5976 0.1758 0.022 Uiso 1 1 calc R U . . .
H1B H 0.5435 0.5834 0.2388 0.022 Uiso 1 1 calc R U . . .
N2 N 0.50021(14) 0.60544(7) 0.09327(8) 0.0194(2) Uani 1 1 d . . . . .
C3 C 0.55485(17) 0.64837(8) 0.00908(10) 0.0217(3) Uani 1 1 d . . . . .
H3A H 0.4864 0.6398 -0.0497 0.026 Uiso 1 1 calc R U . . .
H3B H 0.6616 0.6331 -0.0083 0.026 Uiso 1 1 calc R U . . .
C3A C 0.55488(15) 0.72758(8) 0.03427(9) 0.0184(2) Uani 1 1 d . . . . .
C4 C 0.61661(17) 0.78448(9) -0.03788(10) 0.0225(3) Uani 1 1 d . . . . .
H4 H 0.6885 0.7774 -0.0904 0.027 Uiso 1 1 calc R U . . .
C5 C 0.54838(17) 0.84575(9) -0.01156(10) 0.0227(3) Uani 1 1 d . . . . .
H5 H 0.5626 0.8920 -0.0408 0.027 Uiso 1 1 calc R U . . .
C6 C 0.44276(16) 0.82692(8) 0.07501(10) 0.0190(2) Uani 1 1 d . . . . .
H6 H 0.3542 0.8610 0.0856 0.023 Uiso 1 1 calc R U . . .
O6 O 0.39861(11) 0.75405(5) 0.04975(7) 0.01837(19) Uani 1 1 d . . . . .
C6A C 0.55206(15) 0.81563(7) 0.16729(9) 0.0172(2) Uani 1 1 d . . . . .
H6A H 0.6255 0.8569 0.1782 0.021 Uiso 1 1 calc R U . . .
C7 C 0.47409(15) 0.79066(7) 0.26394(9) 0.0157(2) Uani 1 1 d . . . . .
H7 H 0.3834 0.8211 0.2839 0.019 Uiso 1 1 calc R U . . .
O7 O 0.43577(10) 0.71577(5) 0.24690(7) 0.01509(17) Uani 1 1 d . . . . .
C7A C 0.60195(15) 0.78364(7) 0.34608(9) 0.0155(2) Uani 1 1 d . . . . .
H7A H 0.6725 0.8266 0.3498 0.019 Uiso 1 1 calc R U . . .
C8 C 0.52922(15) 0.76513(7) 0.44499(9) 0.0154(2) Uani 1 1 d . . . . .
O8 O 0.44349(12) 0.80288(5) 0.49346(7) 0.0202(2) Uani 1 1 d . . . . .
N9 N 0.57089(13) 0.69451(6) 0.47067(8) 0.0155(2) Uani 1 1 d . . . . .
C10 C 0.66463(15) 0.66154(7) 0.39950(9) 0.0156(2) Uani 1 1 d . . . . .
O10 O 0.71599(12) 0.60077(5) 0.40643(7) 0.0200(2) Uani 1 1 d . . . . .
C10A C 0.68635(15) 0.71374(7) 0.31402(9) 0.0156(2) Uani 1 1 d . . . . .
H10A H 0.7986 0.7222 0.2990 0.019 Uiso 1 1 calc R U . . .
C10B C 0.59003(14) 0.69219(7) 0.21933(9) 0.0150(2) Uani 1 1 d . . . . .
C10C C 0.63620(15) 0.74492(7) 0.13617(9) 0.0164(2) Uani 1 1 d . . . . .
H10C H 0.7514 0.7510 0.1305 0.020 Uiso 1 1 calc R U . . .
C11 C 0.35067(18) 0.58151(8) 0.09058(10) 0.0227(3) Uani 1 1 d . . . . .
O11 O 0.26394(14) 0.58669(7) 0.01842(8) 0.0307(3) Uani 1 1 d . . . . .
O12 O 0.31636(12) 0.54799(6) 0.17712(8) 0.0249(2) Uani 1 1 d . . . . .
C12 C 0.15488(17) 0.53081(8) 0.20265(11) 0.0238(3) Uani 1 1 d . . . . .
C13 C 0.17421(18) 0.50007(9) 0.30721(12) 0.0268(3) Uani 1 1 d . . . . .
H13A H 0.2372 0.4559 0.3046 0.040 Uiso 1 1 calc R U . . .
H13B H 0.0716 0.4887 0.3343 0.040 Uiso 1 1 calc R U . . .
H13C H 0.2263 0.5357 0.3502 0.040 Uiso 1 1 calc R U . . .
C14 C 0.0606(2) 0.59992(11) 0.20495(15) 0.0394(4) Uani 1 1 d . . . . .
H14A H 0.0405 0.6165 0.1365 0.059 Uiso 1 1 calc R U . . .
H14B H 0.1188 0.6371 0.2417 0.059 Uiso 1 1 calc R U . . .
H14C H -0.0386 0.5909 0.2381 0.059 Uiso 1 1 calc R U . . .
C15 C 0.0901(3) 0.47431(12) 0.13186(15) 0.0470(5) Uani 1 1 d . . . . .
H15A H 0.1577 0.4316 0.1331 0.071 Uiso 1 1 calc R U . . .
H15B H 0.0856 0.4941 0.0640 0.071 Uiso 1 1 calc R U . . .
H15C H -0.0148 0.4606 0.1526 0.071 Uiso 1 1 calc R U . . .
C16 C 0.52636(14) 0.66088(7) 0.56212(9) 0.0148(2) Uani 1 1 d . . . . .
C17 C 0.56342(16) 0.69504(7) 0.65182(10) 0.0177(2) Uani 1 1 d . . . . .
H17 H 0.6188 0.7395 0.6523 0.021 Uiso 1 1 calc R U . . .
C18 C 0.51810(17) 0.66298(8) 0.74079(10) 0.0201(3) Uani 1 1 d . . . . .
H18 H 0.5413 0.6861 0.8025 0.024 Uiso 1 1 calc R U . . .
C19 C 0.43910(17) 0.59739(8) 0.74007(10) 0.0207(3) Uani 1 1 d . . . . .
H19 H 0.4090 0.5757 0.8012 0.025 Uiso 1 1 calc R U . . .
C20 C 0.40405(16) 0.56345(8) 0.64996(10) 0.0204(3) Uani 1 1 d . . . . .
H20 H 0.3505 0.5185 0.6495 0.024 Uiso 1 1 calc R U . . .
C21 C 0.44744(15) 0.59535(7) 0.56031(10) 0.0180(2) Uani 1 1 d . . . . .
H21 H 0.4233 0.5725 0.4985 0.022 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
C1 N2 1.4621(16) . ?
C1 C10B 1.5147(19) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C11 1.3590(19) . ?
N2 C3 1.4612(18) . ?
C3 C3A 1.504(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A O6 1.4463(16) . ?
C3A C4 1.5280(19) . ?
C3A C10C 1.5594(18) . ?
C4 C5 1.326(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.5213(19) . ?
C5 H5 0.9500 . ?
C6 O6 1.4395(17) . ?
C6 C6A 1.5575(18) . ?
C6 H6 1.0000 . ?
C6A C7 1.5358(18) . ?
C6A C10C 1.5538(19) . ?
C6A H6A 1.0000 . ?
C7 O7 1.4416(16) . ?
C7 C7A 1.5510(18) . ?
C7 H7 1.0000 . ?
O7 C10B 1.4473(15) . ?
C7A C8 1.5108(18) . ?
C7A C10A 1.5457(18) . ?
C7A H7A 1.0000 . ?
C8 O8 1.2095(16) . ?
C8 N9 1.3965(17) . ?
N9 C10 1.3956(16) . ?
N9 C16 1.4300(16) . ?
C10 O10 1.2108(16) . ?
C10 C10A 1.5110(18) . ?
C10A C10B 1.5581(17) . ?
C10A H10A 1.0000 . ?
C10B C10C 1.5362(18) . ?
C10C H10C 1.0000 . ?
C11 O11 1.2174(17) . ?
C11 O12 1.3502(17) . ?
O12 C12 1.4676(18) . ?
C12 C15 1.513(2) . ?
C12 C14 1.514(2) . ?
C12 C13 1.519(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C21 1.3890(18) . ?
C16 C17 1.3912(18) . ?
C17 C18 1.3908(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.3928(19) . ?
C20 H20 0.9500 . ?
C21 H21 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
N2 C1 C10B 110.60(11) . . ?
N2 C1 H1A 109.5 . . ?
C10B C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
C10B C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C11 N2 C3 117.96(12) . . ?
C11 N2 C1 123.00(11) . . ?
C3 N2 C1 115.31(11) . . ?
N2 C3 C3A 110.83(11) . . ?
N2 C3 H3A 109.5 . . ?
C3A C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
C3A C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
O6 C3A C3 111.36(11) . . ?
O6 C3A C4 100.79(11) . . ?
C3 C3A C4 121.90(12) . . ?
O6 C3A C10C 102.24(10) . . ?
C3 C3A C10C 113.31(11) . . ?
C4 C3A C10C 104.87(11) . . ?
C5 C4 C3A 105.24(12) . . ?
C5 C4 H4 127.4 . . ?
C3A C4 H4 127.4 . . ?
C4 C5 C6 106.06(13) . . ?
C4 C5 H5 127.0 . . ?
C6 C5 H5 127.0 . . ?
O6 C6 C5 101.13(11) . . ?
O6 C6 C6A 102.46(10) . . ?
C5 C6 C6A 106.03(11) . . ?
O6 C6 H6 115.2 . . ?
C5 C6 H6 115.2 . . ?
C6A C6 H6 115.2 . . ?
C6 O6 C3A 96.21(10) . . ?
C7 C6A C10C 100.48(10) . . ?
C7 C6A C6 116.39(11) . . ?
C10C C6A C6 100.25(10) . . ?
C7 C6A H6A 112.8 . . ?
C10C C6A H6A 112.8 . . ?
C6 C6A H6A 112.8 . . ?
O7 C7 C6A 104.87(10) . . ?
O7 C7 C7A 100.97(10) . . ?
C6A C7 C7A 108.11(10) . . ?
O7 C7 H7 113.9 . . ?
C6A C7 H7 113.9 . . ?
C7A C7 H7 113.9 . . ?
C7 O7 C10B 97.00(9) . . ?
C8 C7A C10A 104.73(10) . . ?
C8 C7A C7 110.14(10) . . ?
C10A C7A C7 101.75(10) . . ?
C8 C7A H7A 113.1 . . ?
C10A C7A H7A 113.1 . . ?
C7 C7A H7A 113.1 . . ?
O8 C8 N9 124.32(12) . . ?
O8 C8 C7A 126.92(12) . . ?
N9 C8 C7A 108.69(11) . . ?
C10 N9 C8 112.88(11) . . ?
C10 N9 C16 123.88(11) . . ?
C8 N9 C16 123.20(11) . . ?
O10 C10 N9 124.48(12) . . ?
O10 C10 C10A 127.10(12) . . ?
N9 C10 C10A 108.41(11) . . ?
C10 C10A C7A 105.16(10) . . ?
C10 C10A C10B 112.59(10) . . ?
C7A C10A C10B 101.18(10) . . ?
C10 C10A H10A 112.4 . . ?
C7A C10A H10A 112.4 . . ?
C10B C10A H10A 112.4 . . ?
O7 C10B C1 111.36(10) . . ?
O7 C10B C10C 103.81(10) . . ?
C1 C10B C10C 113.17(10) . . ?
O7 C10B C10A 101.21(9) . . ?
C1 C10B C10A 118.90(11) . . ?
C10C C10B C10A 106.77(10) . . ?
C10B C10C C6A 102.42(10) . . ?
C10B C10C C3A 112.78(11) . . ?
C6A C10C C3A 101.71(10) . . ?
C10B C10C H10C 113.0 . . ?
C6A C10C H10C 113.0 . . ?
C3A C10C H10C 113.0 . . ?
O11 C11 O12 125.45(14) . . ?
O11 C11 N2 124.40(14) . . ?
O12 C11 N2 110.05(12) . . ?
C11 O12 C12 121.07(11) . . ?
O12 C12 C15 110.19(14) . . ?
O12 C12 C14 109.23(13) . . ?
C15 C12 C14 113.79(16) . . ?
O12 C12 C13 101.68(11) . . ?
C15 C12 C13 110.78(14) . . ?
C14 C12 C13 110.49(14) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 121.21(12) . . ?
C21 C16 N9 120.01(11) . . ?
C17 C16 N9 118.78(12) . . ?
C18 C17 C16 118.88(13) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C19 C18 C17 120.51(13) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 120.06(12) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 119.98(13) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 119.36(12) . . ?
C16 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10B C1 N2 C11 -99.26(15) . . . . ?
C10B C1 N2 C3 58.47(15) . . . . ?
C11 N2 C3 C3A 100.77(15) . . . . ?
C1 N2 C3 C3A -58.14(16) . . . . ?
N2 C3 C3A O6 -65.31(14) . . . . ?
N2 C3 C3A C4 175.98(12) . . . . ?
N2 C3 C3A C10C 49.29(15) . . . . ?
O6 C3A C4 C5 33.44(14) . . . . ?
C3 C3A C4 C5 157.19(13) . . . . ?
C10C C3A C4 C5 -72.45(13) . . . . ?
C3A C4 C5 C6 -1.01(14) . . . . ?
C4 C5 C6 O6 -31.92(14) . . . . ?
C4 C5 C6 C6A 74.67(14) . . . . ?
C5 C6 O6 C3A 50.85(11) . . . . ?
C6A C6 O6 C3A -58.52(11) . . . . ?
C3 C3A O6 C6 177.87(10) . . . . ?
C4 C3A O6 C6 -51.42(11) . . . . ?
C10C C3A O6 C6 56.56(11) . . . . ?
O6 C6 C6A C7 -70.24(14) . . . . ?
C5 C6 C6A C7 -175.86(12) . . . . ?
O6 C6 C6A C10C 36.98(12) . . . . ?
C5 C6 C6A C10C -68.64(13) . . . . ?
C10C C6A C7 O7 -33.55(12) . . . . ?
C6 C6A C7 O7 73.54(13) . . . . ?
C10C C6A C7 C7A 73.55(12) . . . . ?
C6 C6A C7 C7A -179.37(11) . . . . ?
C6A C7 O7 C10B 53.87(11) . . . . ?
C7A C7 O7 C10B -58.41(10) . . . . ?
O7 C7 C7A C8 -74.88(12) . . . . ?
C6A C7 C7A C8 175.34(11) . . . . ?
O7 C7 C7A C10A 35.79(11) . . . . ?
C6A C7 C7A C10A -73.99(12) . . . . ?
C10A C7A C8 O8 -174.72(13) . . . . ?
C7 C7A C8 O8 -66.02(17) . . . . ?
C10A C7A C8 N9 2.39(13) . . . . ?
C7 C7A C8 N9 111.10(12) . . . . ?
O8 C8 N9 C10 176.84(12) . . . . ?
C7A C8 N9 C10 -0.36(14) . . . . ?
O8 C8 N9 C16 -5.3(2) . . . . ?
C7A C8 N9 C16 177.51(11) . . . . ?
C8 N9 C10 O10 179.22(12) . . . . ?
C16 N9 C10 O10 1.4(2) . . . . ?
C8 N9 C10 C10A -1.92(14) . . . . ?
C16 N9 C10 C10A -179.77(11) . . . . ?
O10 C10 C10A C7A -177.89(13) . . . . ?
N9 C10 C10A C7A 3.29(13) . . . . ?
O10 C10 C10A C10B 72.83(16) . . . . ?
N9 C10 C10A C10B -105.99(12) . . . . ?
C8 C7A C10A C10 -3.37(12) . . . . ?
C7 C7A C10A C10 -118.10(10) . . . . ?
C8 C7A C10A C10B 113.97(10) . . . . ?
C7 C7A C10A C10B -0.76(12) . . . . ?
C7 O7 C10B C1 -174.71(10) . . . . ?
C7 O7 C10B C10C -52.64(11) . . . . ?
C7 O7 C10B C10A 57.95(10) . . . . ?
N2 C1 C10B O7 66.15(13) . . . . ?
N2 C1 C10B C10C -50.34(14) . . . . ?
N2 C1 C10B C10A -176.84(11) . . . . ?
C10 C10A C10B O7 77.43(12) . . . . ?
C7A C10A C10B O7 -34.34(11) . . . . ?
C10 C10A C10B C1 -44.80(15) . . . . ?
C7A C10A C10B C1 -156.58(11) . . . . ?
C10 C10A C10B C10C -174.27(10) . . . . ?
C7A C10A C10B C10C 73.95(11) . . . . ?
O7 C10B C10C C6A 32.05(12) . . . . ?
C1 C10B C10C C6A 152.92(10) . . . . ?
C10A C10B C10C C6A -74.39(12) . . . . ?
O7 C10B C10C C3A -76.48(12) . . . . ?
C1 C10B C10C C3A 44.39(15) . . . . ?
C10A C10B C10C C3A 177.07(10) . . . . ?
C7 C6A C10C C10B 0.66(12) . . . . ?
C6 C6A C10C C10B -118.86(10) . . . . ?
C7 C6A C10C C3A 117.45(10) . . . . ?
C6 C6A C10C C3A -2.07(12) . . . . ?
O6 C3A C10C C10B 75.92(13) . . . . ?
C3 C3A C10C C10B -44.04(15) . . . . ?
C4 C3A C10C C10B -179.25(11) . . . . ?
O6 C3A C10C C6A -33.06(12) . . . . ?
C3 C3A C10C C6A -153.02(11) . . . . ?
C4 C3A C10C C6A 71.76(12) . . . . ?
C3 N2 C11 O11 8.2(2) . . . . ?
C1 N2 C11 O11 165.39(14) . . . . ?
C3 N2 C11 O12 -175.14(12) . . . . ?
C1 N2 C11 O12 -17.96(19) . . . . ?
O11 C11 O12 C12 -16.6(2) . . . . ?
N2 C11 O12 C12 166.82(12) . . . . ?
C11 O12 C12 C15 66.81(18) . . . . ?
C11 O12 C12 C14 -58.89(18) . . . . ?
C11 O12 C12 C13 -175.67(13) . . . . ?
C10 N9 C16 C21 -57.47(17) . . . . ?
C8 N9 C16 C21 124.90(14) . . . . ?
C10 N9 C16 C17 122.60(14) . . . . ?
C8 N9 C16 C17 -55.03(17) . . . . ?
C21 C16 C17 C18 -0.9(2) . . . . ?
N9 C16 C17 C18 179.01(12) . . . . ?
C16 C17 C18 C19 0.9(2) . . . . ?
C17 C18 C19 C20 -0.3(2) . . . . ?
C18 C19 C20 C21 -0.3(2) . . . . ?
C17 C16 C21 C20 0.3(2) . . . . ?
N9 C16 C21 C20 -179.64(12) . . . . ?
C19 C20 C21 C16 0.3(2) . . . . ?

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
C14 H14A O8 0.98 2.56 3.493(2) 159.2 4_575

_refine_diff_density_max         0.413
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_4e
_database_code_depnum_ccdc_archive 'CCDC 2026168'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2020-08-30 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N O5'
_chemical_formula_sum            'C15 H15 N O5'
_chemical_formula_weight         289.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -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'

_cell_length_a                   16.625(3)
_cell_length_b                   7.2251(14)
_cell_length_c                   10.625(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.13(3)
_cell_angle_gamma                90
_cell_volume                     1275.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      36.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.244
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   'Scala (Evans, 2005)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11008
_diffrn_reflns_av_unetI/netI     0.1698
_diffrn_reflns_av_R_equivalents  0.1056
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.347
_diffrn_reflns_theta_max         35.996
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_point_group_measured_fraction_full 0.902
_reflns_number_total             4262
_reflns_number_gt                3252
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_max     0.836
_reflns_Friedel_fraction_full    0.848

_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       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  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)+7.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.048(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1234 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4262
_refine_ls_number_parameters     382
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1283
_refine_ls_R_factor_gt           0.1082
_refine_ls_wR_factor_ref         0.2632
_refine_ls_wR_factor_gt          0.2459
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.025
_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 0.2732(7) -0.1234(14) 0.4760(14) 0.031(3) Uani 1 1 d . . . . .
H1A H 0.3035 -0.1708 0.4042 0.038 Uiso 1 1 calc R U . . .
H1B H 0.3035 -0.1570 0.5546 0.038 Uiso 1 1 calc R U . . .
O2 O 0.1945(5) -0.2109(10) 0.4751(9) 0.034(2) Uani 1 1 d . . . . .
O3 O 0.0855(5) 0.1142(11) 0.4425(9) 0.035(2) Uani 1 1 d . . . . .
O4 O 0.2277(5) 0.1624(10) 0.5756(8) 0.027(2) Uani 1 1 d . . . . .
O5 O 0.3510(5) 0.5432(11) 0.7140(9) 0.034(2) Uani 1 1 d . . . . .
O6 O 0.4522(5) 0.0039(10) 0.5619(9) 0.036(2) Uani 1 1 d . . . . .
C3 C 0.1462(8) -0.1702(15) 0.3631(14) 0.038(3) Uani 1 1 d . . . . .
H3A H 0.0935 -0.2329 0.3684 0.046 Uiso 1 1 calc R U . . .
H3B H 0.1732 -0.2205 0.2890 0.046 Uiso 1 1 calc R U . . .
C3A C 0.1326(7) 0.0341(15) 0.3447(13) 0.028(3) Uani 1 1 d . . . . .
C4 C 0.0894(7) 0.1074(16) 0.2270(14) 0.034(3) Uani 1 1 d . . . . .
H4 H 0.0817 0.0464 0.1482 0.041 Uiso 1 1 calc R U . . .
C5 C 0.0643(7) 0.2779(16) 0.2583(12) 0.031(3) Uani 1 1 d . . . . .
H5 H 0.0373 0.3651 0.2048 0.037 Uiso 1 1 calc R U . . .
C6 C 0.0877(7) 0.3017(14) 0.3949(11) 0.025(3) Uani 1 1 d . . . . .
H6 H 0.0551 0.3938 0.4414 0.030 Uiso 1 1 calc R U . . .
C6A C 0.1823(7) 0.3389(14) 0.3984(12) 0.027(3) Uani 1 1 d . . . . .
H6A H 0.1982 0.4415 0.3412 0.033 Uiso 1 1 calc R U . . .
C7 C 0.2233(7) 0.3512(13) 0.5314(11) 0.024(3) Uani 1 1 d . . . . .
H7 H 0.1968 0.4388 0.5898 0.029 Uiso 1 1 calc R U . . .
C7A C 0.3159(7) 0.3908(14) 0.5128(11) 0.024(3) Uani 1 1 d . . . . .
H7A H 0.3254 0.4951 0.4532 0.029 Uiso 1 1 calc R U . . .
C8 C 0.3583(7) 0.4167(13) 0.6396(11) 0.023(3) Uani 1 1 d . . . . .
N9 N 0.4105(5) 0.2649(11) 0.6628(9) 0.024(2) Uani 1 1 d . . . . .
C10 C 0.4084(7) 0.1418(13) 0.5643(12) 0.027(3) Uani 1 1 d . . . . .
C10A C 0.3469(6) 0.2014(13) 0.4644(12) 0.022(2) Uani 1 1 d . . . . .
H10A H 0.3694 0.2094 0.3786 0.026 Uiso 1 1 calc R U . . .
C10B C 0.2673(7) 0.0848(14) 0.4668(11) 0.023(3) Uani 1 1 d . . . . .
C10C C 0.2124(6) 0.1497(14) 0.3576(13) 0.027(3) Uani 1 1 d . . . . .
H10C H 0.2411 0.1558 0.2766 0.032 Uiso 1 1 calc R U . . .
C11 C 0.4637(8) 0.2474(14) 0.7744(11) 0.030(3) Uani 1 1 d . . . . .
H11A H 0.4673 0.3667 0.8181 0.045 Uiso 1 1 calc R U . . .
H11B H 0.5175 0.2100 0.7491 0.045 Uiso 1 1 calc R U . . .
H11C H 0.4423 0.1538 0.8308 0.045 Uiso 1 1 calc R U . . .
C12 C 0.7312(7) 0.3740(15) 0.5009(13) 0.030(3) Uani 1 1 d . . . . .
H12A H 0.7022 0.3403 0.5773 0.036 Uiso 1 1 calc R U . . .
H12B H 0.6997 0.3264 0.4269 0.036 Uiso 1 1 calc R U . . .
O13 O 0.8096(5) 0.2876(10) 0.5059(9) 0.034(2) Uani 1 1 d . . . . .
O14 O 0.9179(4) 0.6146(10) 0.4850(8) 0.027(2) Uani 1 1 d . . . . .
O15 O 0.7752(4) 0.6594(9) 0.6052(8) 0.0229(18) Uani 1 1 d . . . . .
O16 O 0.6532(5) 1.0435(10) 0.7309(9) 0.033(2) Uani 1 1 d . . . . .
O17 O 0.5513(5) 0.5018(10) 0.5687(9) 0.038(2) Uani 1 1 d . . . . .
C14 C 0.8568(7) 0.3321(15) 0.3975(13) 0.032(3) Uani 1 1 d . . . . .
H14A H 0.8292 0.2818 0.3207 0.038 Uiso 1 1 calc R U . . .
H14B H 0.9099 0.2709 0.4072 0.038 Uiso 1 1 calc R U . . .
C14A C 0.8691(6) 0.5338(14) 0.3811(12) 0.024(3) Uani 1 1 d . . . . .
C15 C 0.9114(6) 0.6146(14) 0.2694(13) 0.029(3) Uani 1 1 d . . . . .
H15 H 0.9194 0.5566 0.1906 0.035 Uiso 1 1 calc R U . . .
C16 C 0.9351(7) 0.7851(15) 0.3051(13) 0.031(3) Uani 1 1 d . . . . .
H16 H 0.9594 0.8759 0.2542 0.037 Uiso 1 1 calc R U . . .
C17 C 0.9154(7) 0.8039(13) 0.4436(12) 0.027(3) Uani 1 1 d . . . . .
H17 H 0.9484 0.8944 0.4945 0.033 Uiso 1 1 calc R U . . .
C17A C 0.8201(7) 0.8381(15) 0.4365(13) 0.033(3) Uani 1 1 d . . . . .
H17A H 0.8046 0.9428 0.3790 0.039 Uiso 1 1 calc R U . . .
C18 C 0.7790(7) 0.8503(13) 0.5622(12) 0.027(3) Uani 1 1 d . . . . .
H18 H 0.8054 0.9374 0.6241 0.032 Uiso 1 1 calc R U . . .
C18A C 0.6876(7) 0.8886(13) 0.5345(11) 0.025(3) Uani 1 1 d . . . . .
H18A H 0.6779 0.9928 0.4738 0.030 Uiso 1 1 calc R U . . .
C19 C 0.6447(7) 0.9149(14) 0.6562(12) 0.026(3) Uani 1 1 d . . . . .
N20 N 0.5934(5) 0.7653(12) 0.6743(10) 0.025(2) Uani 1 1 d . . . . .
C21 C 0.5942(6) 0.6401(13) 0.5770(12) 0.025(3) Uani 1 1 d . . . . .
C21A C 0.6566(6) 0.7014(14) 0.4826(12) 0.024(3) Uani 1 1 d . . . . .
H21A H 0.6336 0.7107 0.3945 0.029 Uiso 1 1 calc R U . . .
C21B C 0.7368(7) 0.5820(14) 0.4921(11) 0.023(3) Uani 1 1 d . . . . .
C21C C 0.7884(6) 0.6493(14) 0.3859(12) 0.027(3) Uani 1 1 d . . . . .
H21C H 0.7585 0.6583 0.3028 0.032 Uiso 1 1 calc R U . . .
C22 C 0.5390(7) 0.7479(16) 0.7785(13) 0.034(3) Uani 1 1 d . . . . .
H22A H 0.5563 0.6440 0.8324 0.050 Uiso 1 1 calc R U . . .
H22B H 0.4842 0.7255 0.7451 0.050 Uiso 1 1 calc R U . . .
H22C H 0.5402 0.8624 0.8280 0.050 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
C1 O2 1.453(14) . ?
C1 C10B 1.510(14) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
O2 C3 1.440(16) . ?
O3 C3A 1.446(15) . ?
O3 C6 1.447(13) . ?
O4 C7 1.444(12) . ?
O4 C10B 1.464(14) . ?
O5 C8 1.218(13) . ?
O6 C10 1.234(13) . ?
C3 C3A 1.505(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.515(18) . ?
C3A C10C 1.569(15) . ?
C4 C5 1.346(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.498(16) . ?
C5 H5 0.9500 . ?
C6 C6A 1.593(16) . ?
C6 H6 1.0000 . ?
C6A C10C 1.525(14) . ?
C6A C7 1.548(16) . ?
C6A H6A 1.0000 . ?
C7 C7A 1.586(16) . ?
C7 H7 1.0000 . ?
C7A C8 1.509(15) . ?
C7A C10A 1.556(14) . ?
C7A H7A 1.0000 . ?
C8 N9 1.414(13) . ?
N9 C10 1.373(15) . ?
N9 C11 1.458(15) . ?
C10 C10A 1.509(16) . ?
C10A C10B 1.571(15) . ?
C10A H10A 1.0000 . ?
C10B C10C 1.523(17) . ?
C10C H10C 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O13 1.446(13) . ?
C12 C21B 1.508(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
O13 C14 1.453(16) . ?
O14 C17 1.437(12) . ?
O14 C14A 1.466(14) . ?
O15 C21B 1.451(13) . ?
O15 C18 1.455(12) . ?
O16 C19 1.226(14) . ?
O17 C21 1.230(13) . ?
C14 C14A 1.482(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14A C15 1.518(18) . ?
C14A C21C 1.582(14) . ?
C15 C16 1.344(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.525(18) . ?
C16 H16 0.9500 . ?
C17 C17A 1.602(17) . ?
C17 H17 1.0000 . ?
C17A C18 1.525(18) . ?
C17A C21C 1.551(15) . ?
C17A H17A 1.0000 . ?
C18 C18A 1.562(16) . ?
C18 H18 1.0000 . ?
C18A C19 1.512(17) . ?
C18A C21A 1.541(14) . ?
C18A H18A 1.0000 . ?
C19 N20 1.395(14) . ?
N20 C21 1.374(15) . ?
N20 C22 1.461(16) . ?
C21 C21A 1.534(17) . ?
C21A C21B 1.588(15) . ?
C21A H21A 1.0000 . ?
C21B C21C 1.523(17) . ?
C21C H21C 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
O2 C1 C10B 112.1(9) . . ?
O2 C1 H1A 109.2 . . ?
C10B C1 H1A 109.2 . . ?
O2 C1 H1B 109.2 . . ?
C10B C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C3 O2 C1 113.0(9) . . ?
C3A O3 C6 95.8(8) . . ?
C7 O4 C10B 97.1(8) . . ?
O2 C3 C3A 112.6(10) . . ?
O2 C3 H3A 109.1 . . ?
C3A C3 H3A 109.1 . . ?
O2 C3 H3B 109.1 . . ?
C3A C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
O3 C3A C3 112.4(10) . . ?
O3 C3A C4 101.6(9) . . ?
C3 C3A C4 121.0(10) . . ?
O3 C3A C10C 101.7(9) . . ?
C3 C3A C10C 112.8(9) . . ?
C4 C3A C10C 105.0(9) . . ?
C5 C4 C3A 104.9(12) . . ?
C5 C4 H4 127.5 . . ?
C3A C4 H4 127.5 . . ?
C4 C5 C6 105.8(11) . . ?
C4 C5 H5 127.1 . . ?
C6 C5 H5 127.1 . . ?
O3 C6 C5 102.8(9) . . ?
O3 C6 C6A 100.9(8) . . ?
C5 C6 C6A 105.2(10) . . ?
O3 C6 H6 115.4 . . ?
C5 C6 H6 115.4 . . ?
C6A C6 H6 115.4 . . ?
C10C C6A C7 99.9(9) . . ?
C10C C6A C6 100.1(8) . . ?
C7 C6A C6 115.5(10) . . ?
C10C C6A H6A 113.2 . . ?
C7 C6A H6A 113.2 . . ?
C6 C6A H6A 113.2 . . ?
O4 C7 C6A 105.0(8) . . ?
O4 C7 C7A 100.0(8) . . ?
C6A C7 C7A 107.0(9) . . ?
O4 C7 H7 114.5 . . ?
C6A C7 H7 114.5 . . ?
C7A C7 H7 114.5 . . ?
C8 C7A C10A 104.7(8) . . ?
C8 C7A C7 109.6(10) . . ?
C10A C7A C7 102.6(8) . . ?
C8 C7A H7A 113.1 . . ?
C10A C7A H7A 113.1 . . ?
C7 C7A H7A 113.1 . . ?
O5 C8 N9 123.0(10) . . ?
O5 C8 C7A 128.1(10) . . ?
N9 C8 C7A 108.8(8) . . ?
C10 N9 C8 111.8(9) . . ?
C10 N9 C11 124.1(9) . . ?
C8 N9 C11 124.0(9) . . ?
O6 C10 N9 122.7(11) . . ?
O6 C10 C10A 126.9(11) . . ?
N9 C10 C10A 110.4(9) . . ?
C10 C10A C7A 104.1(9) . . ?
C10 C10A C10B 112.7(9) . . ?
C7A C10A C10B 100.2(9) . . ?
C10 C10A H10A 113.0 . . ?
C7A C10A H10A 113.0 . . ?
C10B C10A H10A 113.0 . . ?
O4 C10B C1 111.1(10) . . ?
O4 C10B C10C 102.1(9) . . ?
C1 C10B C10C 113.0(9) . . ?
O4 C10B C10A 102.2(8) . . ?
C1 C10B C10A 118.9(9) . . ?
C10C C10B C10A 107.7(9) . . ?
C10B C10C C6A 104.7(10) . . ?
C10B C10C C3A 112.5(10) . . ?
C6A C10C C3A 102.5(8) . . ?
C10B C10C H10C 112.2 . . ?
C6A C10C H10C 112.2 . . ?
C3A C10C H10C 112.2 . . ?
N9 C11 H11A 109.5 . . ?
N9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O13 C12 C21B 112.0(9) . . ?
O13 C12 H12A 109.2 . . ?
C21B C12 H12A 109.2 . . ?
O13 C12 H12B 109.2 . . ?
C21B C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 O13 C14 112.9(9) . . ?
C17 O14 C14A 98.0(8) . . ?
C21B O15 C18 97.4(8) . . ?
O13 C14 C14A 113.1(10) . . ?
O13 C14 H14A 109.0 . . ?
C14A C14 H14A 109.0 . . ?
O13 C14 H14B 109.0 . . ?
C14A C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
O14 C14A C14 112.2(9) . . ?
O14 C14A C15 100.1(8) . . ?
C14 C14A C15 122.7(10) . . ?
O14 C14A C21C 102.2(9) . . ?
C14 C14A C21C 113.2(9) . . ?
C15 C14A C21C 103.9(9) . . ?
C16 C15 C14A 105.8(11) . . ?
C16 C15 H15 127.1 . . ?
C14A C15 H15 127.1 . . ?
C15 C16 C17 106.4(10) . . ?
C15 C16 H16 126.8 . . ?
C17 C16 H16 126.8 . . ?
O14 C17 C16 101.9(8) . . ?
O14 C17 C17A 100.2(8) . . ?
C16 C17 C17A 102.5(9) . . ?
O14 C17 H17 116.6 . . ?
C16 C17 H17 116.6 . . ?
C17A C17 H17 116.6 . . ?
C18 C17A C21C 101.3(9) . . ?
C18 C17A C17 116.2(10) . . ?
C21C C17A C17 101.7(8) . . ?
C18 C17A H17A 112.2 . . ?
C21C C17A H17A 112.2 . . ?
C17 C17A H17A 112.2 . . ?
O15 C18 C17A 104.3(8) . . ?
O15 C18 C18A 100.0(8) . . ?
C17A C18 C18A 108.1(10) . . ?
O15 C18 H18 114.4 . . ?
C17A C18 H18 114.4 . . ?
C18A C18 H18 114.4 . . ?
C19 C18A C21A 104.8(9) . . ?
C19 C18A C18 110.3(10) . . ?
C21A C18A C18 102.8(8) . . ?
C19 C18A H18A 112.7 . . ?
C21A C18A H18A 112.7 . . ?
C18 C18A H18A 112.7 . . ?
O16 C19 N20 123.7(11) . . ?
O16 C19 C18A 127.1(10) . . ?
N20 C19 C18A 109.3(9) . . ?
C21 N20 C19 112.5(10) . . ?
C21 N20 C22 122.5(9) . . ?
C19 N20 C22 124.7(9) . . ?
O17 C21 N20 124.5(12) . . ?
O17 C21 C21A 126.4(11) . . ?
N20 C21 C21A 109.1(9) . . ?
C21 C21A C18A 104.1(9) . . ?
C21 C21A C21B 112.8(9) . . ?
C18A C21A C21B 100.7(8) . . ?
C21 C21A H21A 112.7 . . ?
C18A C21A H21A 112.7 . . ?
C21B C21A H21A 112.7 . . ?
O15 C21B C12 111.0(9) . . ?
O15 C21B C21C 104.3(9) . . ?
C12 C21B C21C 113.7(9) . . ?
O15 C21B C21A 100.7(8) . . ?
C12 C21B C21A 119.4(9) . . ?
C21C C21B C21A 105.9(9) . . ?
C21B C21C C17A 102.6(9) . . ?
C21B C21C C14A 111.0(9) . . ?
C17A C21C C14A 101.4(8) . . ?
C21B C21C H21C 113.6 . . ?
C17A C21C H21C 113.6 . . ?
C14A C21C H21C 113.6 . . ?
N20 C22 H22A 109.5 . . ?
N20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C10B C1 O2 C3 59.2(14) . . . . ?
C1 O2 C3 C3A -58.5(14) . . . . ?
C6 O3 C3A C3 178.6(10) . . . . ?
C6 O3 C3A C4 -50.6(9) . . . . ?
C6 O3 C3A C10C 57.6(9) . . . . ?
O2 C3 C3A O3 -65.1(13) . . . . ?
O2 C3 C3A C4 174.8(10) . . . . ?
O2 C3 C3A C10C 49.3(15) . . . . ?
O3 C3A C4 C5 34.8(11) . . . . ?
C3 C3A C4 C5 160.1(11) . . . . ?
C10C C3A C4 C5 -70.8(12) . . . . ?
C3A C4 C5 C6 -3.3(12) . . . . ?
C3A O3 C6 C5 49.0(10) . . . . ?
C3A O3 C6 C6A -59.5(9) . . . . ?
C4 C5 C6 O3 -29.3(12) . . . . ?
C4 C5 C6 C6A 75.9(11) . . . . ?
O3 C6 C6A C10C 38.2(11) . . . . ?
C5 C6 C6A C10C -68.5(10) . . . . ?
O3 C6 C6A C7 -68.1(10) . . . . ?
C5 C6 C6A C7 -174.7(8) . . . . ?
C10B O4 C7 C6A 52.8(10) . . . . ?
C10B O4 C7 C7A -58.0(9) . . . . ?
C10C C6A C7 O4 -31.4(11) . . . . ?
C6 C6A C7 O4 75.0(11) . . . . ?
C10C C6A C7 C7A 74.3(9) . . . . ?
C6 C6A C7 C7A -179.3(8) . . . . ?
O4 C7 C7A C8 -74.5(10) . . . . ?
C6A C7 C7A C8 176.3(8) . . . . ?
O4 C7 C7A C10A 36.3(10) . . . . ?
C6A C7 C7A C10A -72.9(9) . . . . ?
C10A C7A C8 O5 -177.7(12) . . . . ?
C7 C7A C8 O5 -68.3(15) . . . . ?
C10A C7A C8 N9 1.8(12) . . . . ?
C7 C7A C8 N9 111.2(10) . . . . ?
O5 C8 N9 C10 -179.5(11) . . . . ?
C7A C8 N9 C10 1.0(13) . . . . ?
O5 C8 N9 C11 -3.2(18) . . . . ?
C7A C8 N9 C11 177.3(10) . . . . ?
C8 N9 C10 O6 176.3(11) . . . . ?
C11 N9 C10 O6 0.0(18) . . . . ?
C8 N9 C10 C10A -3.5(13) . . . . ?
C11 N9 C10 C10A -179.8(10) . . . . ?
O6 C10 C10A C7A -175.4(11) . . . . ?
N9 C10 C10A C7A 4.3(13) . . . . ?
O6 C10 C10A C10B 77.0(16) . . . . ?
N9 C10 C10A C10B -103.2(10) . . . . ?
C8 C7A C10A C10 -3.6(12) . . . . ?
C7 C7A C10A C10 -118.0(9) . . . . ?
C8 C7A C10A C10B 113.1(10) . . . . ?
C7 C7A C10A C10B -1.3(10) . . . . ?
C7 O4 C10B C1 -173.6(9) . . . . ?
C7 O4 C10B C10C -52.8(9) . . . . ?
C7 O4 C10B C10A 58.6(9) . . . . ?
O2 C1 C10B O4 62.8(13) . . . . ?
O2 C1 C10B C10C -51.4(14) . . . . ?
O2 C1 C10B C10A -179.1(10) . . . . ?
C10 C10A C10B O4 76.2(11) . . . . ?
C7A C10A C10B O4 -33.8(10) . . . . ?
C10 C10A C10B C1 -46.5(15) . . . . ?
C7A C10A C10B C1 -156.5(11) . . . . ?
C10 C10A C10B C10C -176.6(9) . . . . ?
C7A C10A C10B C10C 73.3(11) . . . . ?
O4 C10B C10C C6A 34.0(10) . . . . ?
C1 C10B C10C C6A 153.5(10) . . . . ?
C10A C10B C10C C6A -73.1(11) . . . . ?
O4 C10B C10C C3A -76.5(10) . . . . ?
C1 C10B C10C C3A 43.0(14) . . . . ?
C10A C10B C10C C3A 176.3(9) . . . . ?
C7 C6A C10C C10B -2.1(11) . . . . ?
C6 C6A C10C C10B -120.5(9) . . . . ?
C7 C6A C10C C3A 115.5(10) . . . . ?
C6 C6A C10C C3A -2.9(11) . . . . ?
O3 C3A C10C C10B 78.7(11) . . . . ?
C3 C3A C10C C10B -42.0(14) . . . . ?
C4 C3A C10C C10B -175.8(10) . . . . ?
O3 C3A C10C C6A -33.2(11) . . . . ?
C3 C3A C10C C6A -153.9(11) . . . . ?
C4 C3A C10C C6A 72.4(12) . . . . ?
C21B C12 O13 C14 -58.1(13) . . . . ?
C12 O13 C14 C14A 57.7(12) . . . . ?
C17 O14 C14A C14 -177.9(10) . . . . ?
C17 O14 C14A C15 50.4(9) . . . . ?
C17 O14 C14A C21C -56.4(10) . . . . ?
O13 C14 C14A O14 65.2(12) . . . . ?
O13 C14 C14A C15 -175.6(9) . . . . ?
O13 C14 C14A C21C -49.7(13) . . . . ?
O14 C14A C15 C16 -35.2(10) . . . . ?
C14 C14A C15 C16 -160.0(10) . . . . ?
C21C C14A C15 C16 70.2(10) . . . . ?
C14A C15 C16 C17 5.6(11) . . . . ?
C14A O14 C17 C16 -47.3(9) . . . . ?
C14A O14 C17 C17A 58.0(10) . . . . ?
C15 C16 C17 O14 26.6(11) . . . . ?
C15 C16 C17 C17A -76.9(10) . . . . ?
O14 C17 C17A C18 71.3(10) . . . . ?
C16 C17 C17A C18 176.0(8) . . . . ?
O14 C17 C17A C21C -37.7(11) . . . . ?
C16 C17 C17A C21C 67.0(10) . . . . ?
C21B O15 C18 C17A -52.8(10) . . . . ?
C21B O15 C18 C18A 58.9(10) . . . . ?
C21C C17A C18 O15 33.6(10) . . . . ?
C17 C17A C18 O15 -75.7(10) . . . . ?
C21C C17A C18 C18A -72.1(9) . . . . ?
C17 C17A C18 C18A 178.6(8) . . . . ?
O15 C18 C18A C19 75.1(10) . . . . ?
C17A C18 C18A C19 -176.2(8) . . . . ?
O15 C18 C18A C21A -36.1(11) . . . . ?
C17A C18 C18A C21A 72.6(10) . . . . ?
C21A C18A C19 O16 177.6(11) . . . . ?
C18 C18A C19 O16 67.6(13) . . . . ?
C21A C18A C19 N20 -1.1(12) . . . . ?
C18 C18A C19 N20 -111.1(9) . . . . ?
O16 C19 N20 C21 179.6(10) . . . . ?
C18A C19 N20 C21 -1.6(13) . . . . ?
O16 C19 N20 C22 4.6(18) . . . . ?
C18A C19 N20 C22 -176.6(10) . . . . ?
C19 N20 C21 O17 -176.4(10) . . . . ?
C22 N20 C21 O17 -1.3(17) . . . . ?
C19 N20 C21 C21A 3.6(12) . . . . ?
C22 N20 C21 C21A 178.8(10) . . . . ?
O17 C21 C21A C18A 176.0(10) . . . . ?
N20 C21 C21A C18A -4.0(11) . . . . ?
O17 C21 C21A C21B -75.7(14) . . . . ?
N20 C21 C21A C21B 104.3(10) . . . . ?
C19 C18A C21A C21 3.0(11) . . . . ?
C18 C18A C21A C21 118.3(10) . . . . ?
C19 C18A C21A C21B -114.1(10) . . . . ?
C18 C18A C21A C21B 1.3(11) . . . . ?
C18 O15 C21B C12 174.2(10) . . . . ?
C18 O15 C21B C21C 51.4(9) . . . . ?
C18 O15 C21B C21A -58.3(9) . . . . ?
O13 C12 C21B O15 -64.9(13) . . . . ?
O13 C12 C21B C21C 52.4(13) . . . . ?
O13 C12 C21B C21A 178.7(10) . . . . ?
C21 C21A C21B O15 -76.3(10) . . . . ?
C18A C21A C21B O15 34.1(10) . . . . ?
C21 C21A C21B C12 45.4(14) . . . . ?
C18A C21A C21B C12 155.9(11) . . . . ?
C21 C21A C21B C21C 175.3(9) . . . . ?
C18A C21A C21B C21C -74.3(10) . . . . ?
O15 C21B C21C C17A -30.8(10) . . . . ?
C12 C21B C21C C17A -151.8(9) . . . . ?
C21A C21B C21C C17A 75.0(10) . . . . ?
O15 C21B C21C C14A 76.8(10) . . . . ?
C12 C21B C21C C14A -44.2(12) . . . . ?
C21A C21B C21C C14A -177.4(8) . . . . ?
C18 C17A C21C C21B -1.7(10) . . . . ?
C17 C17A C21C C21B 118.5(10) . . . . ?
C18 C17A C21C C14A -116.5(10) . . . . ?
C17 C17A C21C C14A 3.7(11) . . . . ?
O14 C14A C21C C21B -77.7(10) . . . . ?
C14 C14A C21C C21B 43.2(14) . . . . ?
C15 C14A C21C C21B 178.5(9) . . . . ?
O14 C14A C21C C17A 30.7(11) . . . . ?
C14 C14A C21C C17A 151.6(11) . . . . ?
C15 C14A C21C C17A -73.1(11) . . . . ?

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
C3 H3B O4 0.99 2.51 3.387(18) 147.9 2_554
C4 H4 O3 0.95 2.48 3.419(18) 170.8 2_554
C10A H10A O5 1.00 2.51 3.240(15) 129.4 2_564
C14 H14A O15 0.99 2.47 3.344(15) 147.6 2_564
C15 H15 O14 0.95 2.51 3.451(16) 170.8 2_564
C21A H21A O16 1.00 2.52 3.247(14) 129.8 2_574

_refine_diff_density_max         1.201
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.147

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_6f
_database_code_depnum_ccdc_archive 'CCDC 2026170'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2020-08-30 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H22 N2 O5'
_chemical_formula_sum            'C27 H22 N2 O5'
_chemical_formula_weight         454.47

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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   9.8725(2)
_cell_length_b                   16.5515(3)
_cell_length_c                   29.9337(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4891.31(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9806
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      32.40

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_F_000             1904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            118382
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.471
_diffrn_reflns_theta_max         32.605
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             8883
_reflns_number_gt                7091
_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. 
  
 Structure factors included contributions from the .fab file. 
  
 _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, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'

_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0608P)²+1.5673P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8883
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
C1 C 0.81720(10) 0.71455(6) 0.67509(3) 0.01800(16) Uani 1 1 d . . . . .
H1A H 0.8977 0.6808 0.6687 0.022 Uiso 1 1 calc R U . . .
H1B H 0.7441 0.6784 0.6857 0.022 Uiso 1 1 calc R U . . .
N2 N 0.77332(8) 0.75441(5) 0.63379(3) 0.01789(15) Uani 1 1 d . . . . .
C3 C 0.86677(10) 0.81504(6) 0.61572(3) 0.02021(17) Uani 1 1 d . . . . .
H3A H 0.8268 0.8401 0.5887 0.024 Uiso 1 1 calc R U . . .
H3B H 0.9530 0.7888 0.6071 0.024 Uiso 1 1 calc R U . . .
C3A C 0.89369(9) 0.87898(6) 0.65029(3) 0.01865(17) Uani 1 1 d . . . . .
C4 C 0.98955(11) 0.94880(6) 0.64007(4) 0.02372(19) Uani 1 1 d . . . . .
H4 H 1.0611 0.9497 0.6188 0.028 Uiso 1 1 calc R U . . .
C5 C 0.95145(11) 1.00835(6) 0.66731(4) 0.0251(2) Uani 1 1 d . . . . .
H5 H 0.9899 1.0608 0.6694 0.030 Uiso 1 1 calc R U . . .
C6 C 0.83337(10) 0.97477(6) 0.69447(3) 0.02101(18) Uani 1 1 d . . . . .
H6 H 0.7718 1.0162 0.7079 0.025 Uiso 1 1 calc R U . . .
O6 O 0.77125(7) 0.92143(4) 0.66232(2) 0.01955(14) Uani 1 1 d . . . . .
C6A C 0.89829(9) 0.91403(6) 0.72841(3) 0.01824(17) Uani 1 1 d . . . . .
H6A H 0.9771 0.9376 0.7448 0.022 Uiso 1 1 calc R U . . .
C7 C 0.80027(9) 0.86825(6) 0.75925(3) 0.01716(16) Uani 1 1 d . . . . .
H7 H 0.7380 0.9040 0.7766 0.021 Uiso 1 1 calc R U . . .
O7 O 0.73167(6) 0.81252(4) 0.72979(2) 0.01606(13) Uani 1 1 d . . . . .
C7A C 0.88371(9) 0.80891(6) 0.78849(3) 0.01716(16) Uani 1 1 d . . . . .
H7A H 0.9651 0.8349 0.8022 0.021 Uiso 1 1 calc R U . . .
C8 C 0.79500(9) 0.76673(6) 0.82252(3) 0.01762(16) Uani 1 1 d . . . . .
O8 O 0.73773(8) 0.79693(5) 0.85411(2) 0.02211(14) Uani 1 1 d . . . . .
N9 N 0.78392(8) 0.68516(5) 0.81071(3) 0.01707(14) Uani 1 1 d . . . . .
C10 C 0.85593(9) 0.66619(6) 0.77225(3) 0.01695(16) Uani 1 1 d . . . . .
O10 O 0.86337(8) 0.59904(4) 0.75616(2) 0.02117(14) Uani 1 1 d . . . . .
C10A C 0.92091(9) 0.74210(5) 0.75463(3) 0.01628(16) Uani 1 1 d . . . . .
H10A H 1.0211 0.7362 0.7510 0.020 Uiso 1 1 calc R U . . .
C10B C 0.85170(9) 0.77436(5) 0.71157(3) 0.01550(15) Uani 1 1 d . . . . .
C10C C 0.94001(9) 0.84544(6) 0.69593(3) 0.01698(16) Uani 1 1 d . . . . .
H10C H 1.0391 0.8331 0.6969 0.020 Uiso 1 1 calc R U . . .
C11 C 0.64277(9) 0.74498(6) 0.61996(3) 0.01716(16) Uani 1 1 d . . . . .
O11 O 0.55708(7) 0.70949(4) 0.64263(2) 0.02150(14) Uani 1 1 d . . . . .
C12 C 0.60548(10) 0.77579(6) 0.57436(3) 0.01857(17) Uani 1 1 d . . . . .
C13 C 0.68663(12) 0.76195(7) 0.53696(4) 0.0267(2) Uani 1 1 d . . . . .
H13 H 0.7709 0.7349 0.5402 0.032 Uiso 1 1 calc R U . . .
C14 C 0.64482(13) 0.78759(8) 0.49490(4) 0.0319(2) Uani 1 1 d . . . . .
H14 H 0.6996 0.7771 0.4695 0.038 Uiso 1 1 calc R U . . .
C15 C 0.52336(13) 0.82831(8) 0.49018(4) 0.0298(2) Uani 1 1 d . . . . .
H15 H 0.4957 0.8470 0.4616 0.036 Uiso 1 1 calc R U . . .
C16 C 0.44194(11) 0.84187(7) 0.52712(4) 0.0267(2) Uani 1 1 d . . . . .
H16 H 0.3585 0.8698 0.5237 0.032 Uiso 1 1 calc R U . . .
C17 C 0.48167(10) 0.81477(6) 0.56920(3) 0.02132(18) Uani 1 1 d . . . . .
H17 H 0.4244 0.8229 0.5943 0.026 Uiso 1 1 calc R U . . .
C18 C 0.71472(9) 0.62598(6) 0.83693(3) 0.01809(17) Uani 1 1 d . . . . .
C19 C 0.75190(12) 0.61533(7) 0.88137(3) 0.02459(19) Uani 1 1 d . . . . .
H19 H 0.8227 0.6466 0.8942 0.030 Uiso 1 1 calc R U . . .
C20 C 0.68325(14) 0.55800(8) 0.90659(4) 0.0322(2) Uani 1 1 d . . . . .
H20 H 0.7075 0.5497 0.9370 0.039 Uiso 1 1 calc R U . . .
C21 C 0.57928(13) 0.51269(7) 0.88773(4) 0.0322(3) Uani 1 1 d . . . . .
H21 H 0.5318 0.4744 0.9054 0.039 Uiso 1 1 calc R U . . .
C22 C 0.54460(11) 0.52320(6) 0.84321(4) 0.0276(2) Uani 1 1 d . . . . .
H22 H 0.4743 0.4916 0.8303 0.033 Uiso 1 1 calc R U . . .
C23 C 0.61287(10) 0.58002(6) 0.81743(4) 0.02146(18) Uani 1 1 d . . . . .
H23 H 0.5901 0.5873 0.7869 0.026 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
C1 N2 1.4668(12) . ?
C1 C10B 1.5126(13) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C11 1.3628(12) . ?
N2 C3 1.4665(12) . ?
C3 C3A 1.5037(14) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A O6 1.4438(12) . ?
C3A C4 1.5247(14) . ?
C3A C10C 1.5441(13) . ?
C4 C5 1.3333(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.5261(15) . ?
C5 H5 0.9500 . ?
C6 O6 1.4428(12) . ?
C6 C6A 1.5665(14) . ?
C6 H6 1.0000 . ?
C6A C7 1.5371(13) . ?
C6A C10C 1.5504(13) . ?
C6A H6A 1.0000 . ?
C7 O7 1.4447(11) . ?
C7 C7A 1.5522(13) . ?
C7 H7 1.0000 . ?
O7 C10B 1.4494(11) . ?
C7A C8 1.5140(13) . ?
C7A C10A 1.5444(13) . ?
C7A H7A 1.0000 . ?
C8 O8 1.2097(12) . ?
C8 N9 1.3999(12) . ?
N9 C10 1.3889(12) . ?
N9 C18 1.4291(12) . ?
C10 O10 1.2135(11) . ?
C10 C10A 1.5061(13) . ?
C10A C10B 1.5534(13) . ?
C10A H10A 1.0000 . ?
C10B C10C 1.5373(13) . ?
C10C H10C 1.0000 . ?
C11 O11 1.2334(12) . ?
C11 C12 1.5029(13) . ?
C12 C17 1.3907(14) . ?
C12 C13 1.3955(14) . ?
C13 C14 1.3912(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.3827(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3854(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.3934(14) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.3896(14) . ?
C18 C19 1.3911(14) . ?
C19 C20 1.3891(16) . ?
C19 H19 0.9500 . ?
C20 C21 1.391(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.3870(18) . ?
C21 H21 0.9500 . ?
C22 C23 1.3907(15) . ?
C22 H22 0.9500 . ?
C23 H23 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
N2 C1 C10B 112.37(8) . . ?
N2 C1 H1A 109.1 . . ?
C10B C1 H1A 109.1 . . ?
N2 C1 H1B 109.1 . . ?
C10B C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
C11 N2 C3 124.14(8) . . ?
C11 N2 C1 118.94(8) . . ?
C3 N2 C1 115.65(8) . . ?
N2 C3 C3A 109.82(8) . . ?
N2 C3 H3A 109.7 . . ?
C3A C3 H3A 109.7 . . ?
N2 C3 H3B 109.7 . . ?
C3A C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
O6 C3A C3 111.48(8) . . ?
O6 C3A C4 101.59(8) . . ?
C3 C3A C4 120.34(8) . . ?
O6 C3A C10C 101.66(7) . . ?
C3 C3A C10C 114.09(8) . . ?
C4 C3A C10C 105.44(8) . . ?
C5 C4 C3A 105.22(9) . . ?
C5 C4 H4 127.4 . . ?
C3A C4 H4 127.4 . . ?
C4 C5 C6 105.79(9) . . ?
C4 C5 H5 127.1 . . ?
C6 C5 H5 127.1 . . ?
O6 C6 C5 101.08(8) . . ?
O6 C6 C6A 102.35(7) . . ?
C5 C6 C6A 105.48(8) . . ?
O6 C6 H6 115.4 . . ?
C5 C6 H6 115.4 . . ?
C6A C6 H6 115.4 . . ?
C6 O6 C3A 96.21(7) . . ?
C7 C6A C10C 100.54(7) . . ?
C7 C6A C6 116.64(8) . . ?
C10C C6A C6 99.89(7) . . ?
C7 C6A H6A 112.8 . . ?
C10C C6A H6A 112.8 . . ?
C6 C6A H6A 112.8 . . ?
O7 C7 C6A 104.08(7) . . ?
O7 C7 C7A 100.90(7) . . ?
C6A C7 C7A 108.45(7) . . ?
O7 C7 H7 114.1 . . ?
C6A C7 H7 114.1 . . ?
C7A C7 H7 114.1 . . ?
C7 O7 C10B 97.16(6) . . ?
C8 C7A C10A 104.42(7) . . ?
C8 C7A C7 111.36(7) . . ?
C10A C7A C7 102.07(7) . . ?
C8 C7A H7A 112.7 . . ?
C10A C7A H7A 112.7 . . ?
C7 C7A H7A 112.7 . . ?
O8 C8 N9 124.01(9) . . ?
O8 C8 C7A 127.28(9) . . ?
N9 C8 C7A 108.66(8) . . ?
C10 N9 C8 112.79(8) . . ?
C10 N9 C18 123.03(8) . . ?
C8 N9 C18 124.02(8) . . ?
O10 C10 N9 124.53(9) . . ?
O10 C10 C10A 126.82(9) . . ?
N9 C10 C10A 108.65(8) . . ?
C10 C10A C7A 105.43(7) . . ?
C10 C10A C10B 112.95(7) . . ?
C7A C10A C10B 101.18(7) . . ?
C10 C10A H10A 112.2 . . ?
C7A C10A H10A 112.2 . . ?
C10B C10A H10A 112.2 . . ?
O7 C10B C1 111.88(7) . . ?
O7 C10B C10C 104.16(7) . . ?
C1 C10B C10C 114.12(8) . . ?
O7 C10B C10A 101.38(7) . . ?
C1 C10B C10A 118.23(7) . . ?
C10C C10B C10A 105.44(7) . . ?
C10B C10C C3A 112.13(7) . . ?
C10B C10C C6A 102.64(7) . . ?
C3A C10C C6A 102.30(7) . . ?
C10B C10C H10C 113.0 . . ?
C3A C10C H10C 113.0 . . ?
C6A C10C H10C 112.9 . . ?
O11 C11 N2 122.42(9) . . ?
O11 C11 C12 119.56(9) . . ?
N2 C11 C12 117.96(8) . . ?
C17 C12 C13 119.45(9) . . ?
C17 C12 C11 118.26(8) . . ?
C13 C12 C11 122.15(9) . . ?
C14 C13 C12 120.37(10) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.90(11) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.03(10) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 120.40(10) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 119.80(10) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C23 C18 C19 121.55(9) . . ?
C23 C18 N9 119.36(9) . . ?
C19 C18 N9 119.09(9) . . ?
C20 C19 C18 118.53(11) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C19 C20 C21 120.51(11) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 120.31(11) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.89(11) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C18 C23 C22 119.19(10) . . ?
C18 C23 H23 120.4 . . ?
C22 C23 H23 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
C10B C1 N2 C11 -113.54(9) . . . . ?
C10B C1 N2 C3 54.17(11) . . . . ?
C11 N2 C3 C3A 110.03(10) . . . . ?
C1 N2 C3 C3A -56.96(11) . . . . ?
N2 C3 C3A O6 -62.09(10) . . . . ?
N2 C3 C3A C4 179.20(8) . . . . ?
N2 C3 C3A C10C 52.36(11) . . . . ?
O6 C3A C4 C5 32.05(10) . . . . ?
C3 C3A C4 C5 155.63(9) . . . . ?
C10C C3A C4 C5 -73.66(10) . . . . ?
C3A C4 C5 C6 0.54(11) . . . . ?
C4 C5 C6 O6 -32.93(10) . . . . ?
C4 C5 C6 C6A 73.35(10) . . . . ?
C5 C6 O6 C3A 50.84(8) . . . . ?
C6A C6 O6 C3A -57.89(8) . . . . ?
C3 C3A O6 C6 179.80(8) . . . . ?
C4 C3A O6 C6 -50.80(8) . . . . ?
C10C C3A O6 C6 57.86(8) . . . . ?
O6 C6 C6A C7 -72.36(10) . . . . ?
C5 C6 C6A C7 -177.71(8) . . . . ?
O6 C6 C6A C10C 34.81(8) . . . . ?
C5 C6 C6A C10C -70.54(9) . . . . ?
C10C C6A C7 O7 -36.12(8) . . . . ?
C6 C6A C7 O7 70.67(9) . . . . ?
C10C C6A C7 C7A 70.68(8) . . . . ?
C6 C6A C7 C7A 177.47(8) . . . . ?
C6A C7 O7 C10B 54.70(8) . . . . ?
C7A C7 O7 C10B -57.67(7) . . . . ?
O7 C7 C7A C8 -75.84(9) . . . . ?
C6A C7 C7A C8 175.17(7) . . . . ?
O7 C7 C7A C10A 35.08(8) . . . . ?
C6A C7 C7A C10A -73.91(8) . . . . ?
C10A C7A C8 O8 -176.42(9) . . . . ?
C7 C7A C8 O8 -67.01(12) . . . . ?
C10A C7A C8 N9 1.13(9) . . . . ?
C7 C7A C8 N9 110.55(8) . . . . ?
O8 C8 N9 C10 177.94(9) . . . . ?
C7A C8 N9 C10 0.28(10) . . . . ?
O8 C8 N9 C18 -6.51(14) . . . . ?
C7A C8 N9 C18 175.84(8) . . . . ?
C8 N9 C10 O10 178.51(9) . . . . ?
C18 N9 C10 O10 2.90(14) . . . . ?
C8 N9 C10 C10A -1.64(10) . . . . ?
C18 N9 C10 C10A -177.24(8) . . . . ?
O10 C10 C10A C7A -177.90(9) . . . . ?
N9 C10 C10A C7A 2.25(9) . . . . ?
O10 C10 C10A C10B 72.51(12) . . . . ?
N9 C10 C10A C10B -107.35(9) . . . . ?
C8 C7A C10A C10 -2.00(9) . . . . ?
C7 C7A C10A C10 -118.08(8) . . . . ?
C8 C7A C10A C10B 115.83(7) . . . . ?
C7 C7A C10A C10B -0.24(8) . . . . ?
C7 O7 C10B C1 -175.24(7) . . . . ?
C7 O7 C10B C10C -51.49(8) . . . . ?
C7 O7 C10B C10A 57.83(8) . . . . ?
N2 C1 C10B O7 72.21(10) . . . . ?
N2 C1 C10B C10C -45.75(10) . . . . ?
N2 C1 C10B C10A -170.60(7) . . . . ?
C10 C10A C10B O7 77.63(9) . . . . ?
C7A C10A C10B O7 -34.60(8) . . . . ?
C10 C10A C10B C1 -45.02(11) . . . . ?
C7A C10A C10B C1 -157.25(8) . . . . ?
C10 C10A C10B C10C -174.04(7) . . . . ?
C7A C10A C10B C10C 73.74(8) . . . . ?
O7 C10B C10C C3A -79.86(9) . . . . ?
C1 C10B C10C C3A 42.43(10) . . . . ?
C10A C10B C10C C3A 173.83(7) . . . . ?
O7 C10B C10C C6A 29.21(9) . . . . ?
C1 C10B C10C C6A 151.50(8) . . . . ?
C10A C10B C10C C6A -77.09(8) . . . . ?
O6 C3A C10C C10B 73.71(9) . . . . ?
C3 C3A C10C C10B -46.42(10) . . . . ?
C4 C3A C10C C10B 179.37(8) . . . . ?
O6 C3A C10C C6A -35.58(8) . . . . ?
C3 C3A C10C C6A -155.70(8) . . . . ?
C4 C3A C10C C6A 70.08(9) . . . . ?
C7 C6A C10C C10B 3.85(9) . . . . ?
C6 C6A C10C C10B -115.85(8) . . . . ?
C7 C6A C10C C3A 120.20(7) . . . . ?
C6 C6A C10C C3A 0.51(8) . . . . ?
C3 N2 C11 O11 -160.70(9) . . . . ?
C1 N2 C11 O11 5.89(14) . . . . ?
C3 N2 C11 C12 22.33(13) . . . . ?
C1 N2 C11 C12 -171.08(8) . . . . ?
O11 C11 C12 C17 43.64(13) . . . . ?
N2 C11 C12 C17 -139.30(9) . . . . ?
O11 C11 C12 C13 -132.18(11) . . . . ?
N2 C11 C12 C13 44.88(14) . . . . ?
C17 C12 C13 C14 0.62(17) . . . . ?
C11 C12 C13 C14 176.40(11) . . . . ?
C12 C13 C14 C15 1.17(19) . . . . ?
C13 C14 C15 C16 -1.52(19) . . . . ?
C14 C15 C16 C17 0.07(18) . . . . ?
C13 C12 C17 C16 -2.06(15) . . . . ?
C11 C12 C17 C16 -178.00(9) . . . . ?
C15 C16 C17 C12 1.73(17) . . . . ?
C10 N9 C18 C23 -59.68(12) . . . . ?
C8 N9 C18 C23 125.20(10) . . . . ?
C10 N9 C18 C19 119.77(10) . . . . ?
C8 N9 C18 C19 -55.34(13) . . . . ?
C23 C18 C19 C20 -0.99(16) . . . . ?
N9 C18 C19 C20 179.57(10) . . . . ?
C18 C19 C20 C21 -0.31(17) . . . . ?
C19 C20 C21 C22 1.21(18) . . . . ?
C20 C21 C22 C23 -0.83(17) . . . . ?
C19 C18 C23 C22 1.36(15) . . . . ?
N9 C18 C23 C22 -179.20(9) . . . . ?
C21 C22 C23 C18 -0.44(16) . . . . ?

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
C6 H6 O10 1.00 2.40 3.3784(13) 166.4 8_765
C10A H10A O7 1.00 2.50 3.3149(11) 138.4 6_657
C10C H10C O8 1.00 2.56 3.3952(12) 141.2 6_657

_refine_diff_density_max         0.392
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-4



