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

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

data_add23
_database_code_depnum_ccdc_archive 'CCDC 1968957'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2019-11-29 deposited with the CCDC.	2020-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H11 N O4 S'
_chemical_formula_weight         253.27

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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                   38.544(4)
_cell_length_b                   5.1102(9)
_cell_length_c                   11.6487(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2294.4(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1801
_cell_measurement_theta_min      3.622
_cell_measurement_theta_max      20.490

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.284
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.68438
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1827
_diffrn_reflns_number            22235
_diffrn_reflns_av_unetI/netI     0.1042
_diffrn_reflns_av_R_equivalents  0.1215
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.171
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_point_group_measured_fraction_full 0.864
_reflns_number_total             5762
_reflns_number_gt                2728
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.651
_reflns_Friedel_fraction_max     0.713
_reflns_Friedel_fraction_full    0.715

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0925P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 647 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.34(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5762
_refine_ls_number_parameters     309
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1406
_refine_ls_R_factor_gt           0.0712
_refine_ls_wR_factor_ref         0.2128
_refine_ls_wR_factor_gt          0.1668
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_restrained_S_all      0.934
_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
S1A S 0.29573(5) 0.0938(3) 0.1809(2) 0.0671(6) Uani 1 1 d . . . . .
O1A O 0.36764(18) 0.2639(11) 0.3548(5) 0.0802(16) Uani 1 1 d . . . . .
O2A O 0.33169(13) 0.6618(10) -0.0140(5) 0.0658(13) Uani 1 1 d . . . . .
O3A O 0.25258(19) 0.0052(14) 0.3796(9) 0.131(4) Uani 1 1 d . . . . .
O4A O 0.21739(16) 0.3353(10) 0.3481(6) 0.0799(17) Uani 1 1 d . . . . .
H4OA H 0.206904 0.274878 0.403331 0.120 Uiso 1 1 calc R U . . .
N1A N 0.35374(15) 0.4908(9) 0.1501(5) 0.0525(13) Uani 1 1 d . . . . .
H1NA H 0.350179 0.370280 0.200258 0.063 Uiso 1 1 calc R U . . .
C1A C 0.38172(17) 0.6580(12) 0.1728(6) 0.0525(15) Uani 1 1 d . . . . .
C2A C 0.39214(19) 0.8526(14) 0.0986(8) 0.0630(18) Uani 1 1 d . . . . .
H2A H 0.380325 0.877787 0.029861 0.076 Uiso 1 1 calc R U . . .
C3A C 0.4203(2) 1.0121(15) 0.1260(9) 0.070(2) Uani 1 1 d . . . . .
H3A H 0.426450 1.148195 0.076976 0.084 Uiso 1 1 calc R U . . .
C4A C 0.4391(2) 0.9705(16) 0.2244(9) 0.078(2) Uani 1 1 d . . . . .
H4A H 0.458317 1.073855 0.241212 0.093 Uiso 1 1 calc R U . . .
C5A C 0.4291(2) 0.7738(14) 0.2977(8) 0.069(2) Uani 1 1 d . . . . .
H5A H 0.441940 0.746877 0.364299 0.083 Uiso 1 1 calc R U . . .
C6A C 0.40071(17) 0.6133(13) 0.2767(7) 0.0570(16) Uani 1 1 d . . . . .
C7A C 0.3918(2) 0.4154(17) 0.3600(7) 0.073(2) Uani 1 1 d . . . . .
H7A H 0.406094 0.402577 0.424193 0.087 Uiso 1 1 calc R U . . .
C8A C 0.33194(17) 0.4928(12) 0.0616(6) 0.0486(15) Uani 1 1 d . . . . .
C9A C 0.3068(2) 0.2669(15) 0.0520(7) 0.066(2) Uani 1 1 d . . . . .
H9AA H 0.316408 0.141600 -0.001841 0.079 Uiso 1 1 calc R U . . .
H9AB H 0.285463 0.333113 0.018619 0.079 Uiso 1 1 calc R U . . .
C10A C 0.2696(3) 0.3388(16) 0.2487(10) 0.097(3) Uani 1 1 d . . . . .
H10A H 0.284314 0.466712 0.286168 0.116 Uiso 1 1 calc R U . . .
H10B H 0.255665 0.428613 0.191562 0.116 Uiso 1 1 calc R U . . .
C11A C 0.2464(2) 0.2116(16) 0.3352(9) 0.075(2) Uani 1 1 d . . . . .
S1B S 0.47817(4) 0.5036(3) 0.78208(18) 0.0508(4) Uani 1 1 d . . . . .
O1B O 0.39282(19) 0.2477(11) 0.8289(6) 0.0875(19) Uani 1 1 d . . . . .
O2B O 0.42662(12) 1.0087(8) 0.5865(4) 0.0572(12) Uani 1 1 d . . . . .
O3B O 0.49532(16) 1.0268(9) 0.9542(5) 0.0662(14) Uani 1 1 d . . . . .
O4B O 0.52352(13) 0.6777(8) 1.0149(4) 0.0580(12) Uani 1 1 d . . . . .
H4OB H 0.538969 0.785166 1.025816 0.087 Uiso 1 1 calc R U . . .
N1B N 0.40783(14) 0.6451(9) 0.6798(5) 0.0545(13) Uani 1 1 d . . . . .
H1NB H 0.414680 0.523703 0.725635 0.065 Uiso 1 1 calc R U . . .
C1B C 0.37304(18) 0.6266(12) 0.6449(6) 0.0526(16) Uani 1 1 d . . . . .
C2B C 0.3590(2) 0.7897(14) 0.5606(7) 0.0641(19) Uani 1 1 d . . . . .
H2B H 0.372509 0.920769 0.527741 0.077 Uiso 1 1 calc R U . . .
C3B C 0.3252(2) 0.7553(17) 0.5263(9) 0.076(2) Uani 1 1 d . . . . .
H3B H 0.315866 0.865306 0.470629 0.091 Uiso 1 1 calc R U . . .
C4B C 0.3050(2) 0.563(2) 0.5725(10) 0.091(3) Uani 1 1 d . . . . .
H4B H 0.282246 0.541756 0.547277 0.109 Uiso 1 1 calc R U . . .
C5B C 0.3181(2) 0.4008(18) 0.6564(10) 0.081(3) Uani 1 1 d . . . . .
H5B H 0.304003 0.272200 0.688242 0.097 Uiso 1 1 calc R U . . .
C6B C 0.3525(2) 0.4269(13) 0.6943(7) 0.0640(19) Uani 1 1 d . . . . .
C7B C 0.3648(3) 0.2513(15) 0.7832(9) 0.078(3) Uani 1 1 d . . . . .
H7B H 0.349071 0.125677 0.808154 0.094 Uiso 1 1 calc R U . . .
C8B C 0.43189(18) 0.8231(11) 0.6526(6) 0.0498(15) Uani 1 1 d . . . . .
C9B C 0.46805(17) 0.7909(11) 0.6993(6) 0.0506(15) Uani 1 1 d . . . . .
H9BA H 0.473030 0.942230 0.746806 0.061 Uiso 1 1 calc R U . . .
H9BB H 0.483957 0.796513 0.634836 0.061 Uiso 1 1 calc R U . . .
C10B C 0.46913(18) 0.6130(12) 0.9268(6) 0.0510(15) Uani 1 1 d . . . . .
H10C H 0.446932 0.702403 0.928686 0.061 Uiso 1 1 calc R U . . .
H10D H 0.467803 0.463201 0.977758 0.061 Uiso 1 1 calc R U . . .
C11B C 0.49689(19) 0.7933(11) 0.9666(6) 0.0477(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1A C10A 1.791(9) . ?
S1A C9A 1.794(8) . ?
O1A C7A 1.213(10) . ?
O2A C8A 1.234(8) . ?
O3A C11A 1.198(9) . ?
O4A C11A 1.295(10) . ?
O4A H4OA 0.8200 . ?
N1A C8A 1.330(8) . ?
N1A C1A 1.401(8) . ?
N1A H1NA 0.8600 . ?
C1A C2A 1.377(10) . ?
C1A C6A 1.433(10) . ?
C2A C3A 1.395(10) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.373(13) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.374(12) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.390(10) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.443(11) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.512(9) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C10A C11A 1.494(12) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
S1B C9B 1.799(6) . ?
S1B C10B 1.810(7) . ?
O1B C7B 1.204(11) . ?
O2B C8B 1.239(7) . ?
O3B C11B 1.204(7) . ?
O4B C11B 1.311(8) . ?
O4B H4OB 0.8200 . ?
N1B C8B 1.337(8) . ?
N1B C1B 1.404(9) . ?
N1B H1NB 0.8600 . ?
C1B C2B 1.397(10) . ?
C1B C6B 1.414(10) . ?
C2B C3B 1.376(10) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.363(14) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.379(14) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.404(12) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.450(13) . ?
C7B H7B 0.9300 . ?
C8B C9B 1.505(9) . ?
C9B H9BA 0.9700 . ?
C9B H9BB 0.9700 . ?
C10B C11B 1.486(9) . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?

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
C10A S1A C9A 99.1(4) . . ?
C11A O4A H4OA 109.5 . . ?
C8A N1A C1A 128.9(6) . . ?
C8A N1A H1NA 115.6 . . ?
C1A N1A H1NA 115.6 . . ?
C2A C1A N1A 123.1(7) . . ?
C2A C1A C6A 119.7(6) . . ?
N1A C1A C6A 117.1(6) . . ?
C1A C2A C3A 120.4(8) . . ?
C1A C2A H2A 119.8 . . ?
C3A C2A H2A 119.8 . . ?
C4A C3A C2A 120.7(8) . . ?
C4A C3A H3A 119.6 . . ?
C2A C3A H3A 119.6 . . ?
C3A C4A C5A 119.0(8) . . ?
C3A C4A H4A 120.5 . . ?
C5A C4A H4A 120.5 . . ?
C4A C5A C6A 122.9(8) . . ?
C4A C5A H5A 118.5 . . ?
C6A C5A H5A 118.5 . . ?
C5A C6A C1A 117.2(7) . . ?
C5A C6A C7A 118.8(8) . . ?
C1A C6A C7A 124.0(7) . . ?
O1A C7A C6A 126.5(8) . . ?
O1A C7A H7A 116.7 . . ?
C6A C7A H7A 116.7 . . ?
O2A C8A N1A 124.3(6) . . ?
O2A C8A C9A 118.5(6) . . ?
N1A C8A C9A 117.2(6) . . ?
C8A C9A S1A 117.8(6) . . ?
C8A C9A H9AA 107.9 . . ?
S1A C9A H9AA 107.9 . . ?
C8A C9A H9AB 107.9 . . ?
S1A C9A H9AB 107.9 . . ?
H9AA C9A H9AB 107.2 . . ?
C11A C10A S1A 109.2(6) . . ?
C11A C10A H10A 109.8 . . ?
S1A C10A H10A 109.8 . . ?
C11A C10A H10B 109.8 . . ?
S1A C10A H10B 109.8 . . ?
H10A C10A H10B 108.3 . . ?
O3A C11A O4A 123.4(8) . . ?
O3A C11A C10A 123.8(8) . . ?
O4A C11A C10A 112.4(8) . . ?
C9B S1B C10B 101.9(3) . . ?
C11B O4B H4OB 109.5 . . ?
C8B N1B C1B 129.8(6) . . ?
C8B N1B H1NB 115.1 . . ?
C1B N1B H1NB 115.1 . . ?
C2B C1B N1B 122.2(6) . . ?
C2B C1B C6B 120.0(7) . . ?
N1B C1B C6B 117.7(6) . . ?
C3B C2B C1B 119.6(8) . . ?
C3B C2B H2B 120.2 . . ?
C1B C2B H2B 120.2 . . ?
C4B C3B C2B 121.3(9) . . ?
C4B C3B H3B 119.4 . . ?
C2B C3B H3B 119.4 . . ?
C3B C4B C5B 120.2(9) . . ?
C3B C4B H4B 119.9 . . ?
C5B C4B H4B 119.9 . . ?
C4B C5B C6B 120.8(8) . . ?
C4B C5B H5B 119.6 . . ?
C6B C5B H5B 119.6 . . ?
C5B C6B C1B 118.0(8) . . ?
C5B C6B C7B 118.3(8) . . ?
C1B C6B C7B 123.7(7) . . ?
O1B C7B C6B 128.2(7) . . ?
O1B C7B H7B 115.9 . . ?
C6B C7B H7B 115.9 . . ?
O2B C8B N1B 123.6(6) . . ?
O2B C8B C9B 117.4(6) . . ?
N1B C8B C9B 118.9(6) . . ?
C8B C9B S1B 118.9(5) . . ?
C8B C9B H9BA 107.6 . . ?
S1B C9B H9BA 107.6 . . ?
C8B C9B H9BB 107.6 . . ?
S1B C9B H9BB 107.6 . . ?
H9BA C9B H9BB 107.0 . . ?
C11B C10B S1B 110.1(5) . . ?
C11B C10B H10C 109.6 . . ?
S1B C10B H10C 109.6 . . ?
C11B C10B H10D 109.6 . . ?
S1B C10B H10D 109.6 . . ?
H10C C10B H10D 108.2 . . ?
O3B C11B O4B 122.5(6) . . ?
O3B C11B C10B 122.7(6) . . ?
O4B C11B C10B 114.7(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
C8A N1A C1A C2A -3.4(11) . . . . ?
C8A N1A C1A C6A 179.0(6) . . . . ?
N1A C1A C2A C3A -179.7(7) . . . . ?
C6A C1A C2A C3A -2.2(11) . . . . ?
C1A C2A C3A C4A 3.0(12) . . . . ?
C2A C3A C4A C5A -2.0(12) . . . . ?
C3A C4A C5A C6A 0.1(12) . . . . ?
C4A C5A C6A C1A 0.6(11) . . . . ?
C4A C5A C6A C7A -178.7(7) . . . . ?
C2A C1A C6A C5A 0.4(10) . . . . ?
N1A C1A C6A C5A 178.1(6) . . . . ?
C2A C1A C6A C7A 179.8(7) . . . . ?
N1A C1A C6A C7A -2.6(9) . . . . ?
C5A C6A C7A O1A 178.8(8) . . . . ?
C1A C6A C7A O1A -0.5(12) . . . . ?
C1A N1A C8A O2A -5.2(11) . . . . ?
C1A N1A C8A C9A 172.6(7) . . . . ?
O2A C8A C9A S1A -157.6(6) . . . . ?
N1A C8A C9A S1A 24.5(9) . . . . ?
C10A S1A C9A C8A 71.4(8) . . . . ?
C9A S1A C10A C11A 158.7(8) . . . . ?
S1A C10A C11A O3A 23.6(14) . . . . ?
S1A C10A C11A O4A -149.7(7) . . . . ?
C8B N1B C1B C2B 7.6(11) . . . . ?
C8B N1B C1B C6B -175.2(7) . . . . ?
N1B C1B C2B C3B 177.3(7) . . . . ?
C6B C1B C2B C3B 0.2(11) . . . . ?
C1B C2B C3B C4B -0.5(13) . . . . ?
C2B C3B C4B C5B 1.0(15) . . . . ?
C3B C4B C5B C6B -1.1(15) . . . . ?
C4B C5B C6B C1B 0.7(12) . . . . ?
C4B C5B C6B C7B 179.7(8) . . . . ?
C2B C1B C6B C5B -0.3(11) . . . . ?
N1B C1B C6B C5B -177.5(7) . . . . ?
C2B C1B C6B C7B -179.2(7) . . . . ?
N1B C1B C6B C7B 3.6(10) . . . . ?
C5B C6B C7B O1B -177.7(9) . . . . ?
C1B C6B C7B O1B 1.1(13) . . . . ?
C1B N1B C8B O2B -1.1(12) . . . . ?
C1B N1B C8B C9B -177.8(6) . . . . ?
O2B C8B C9B S1B -172.9(5) . . . . ?
N1B C8B C9B S1B 4.0(9) . . . . ?
C10B S1B C9B C8B -91.7(6) . . . . ?
C9B S1B C10B C11B -74.0(5) . . . . ?
S1B C10B C11B O3B 91.3(8) . . . . ?
S1B C10B C11B O4B -87.7(6) . . . . ?

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
N1A H1NA O1A 0.86 2.00 2.705(8) 138.9 .
N1B H1NB O1B 0.86 2.04 2.734(8) 137.7 .
O4A H4OA O2A 0.82 1.86 2.635(8) 156.2 4_545
O4B H4OB O2B 0.82 1.84 2.638(6) 165.7 2_675

_refine_diff_density_max         0.623
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_add24
_database_code_depnum_ccdc_archive 'CCDC 1968958'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2019-11-29 deposited with the CCDC.	2020-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H11 N O5'
_chemical_formula_weight         237.21

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   20.486(2)
_cell_length_b                   3.9298(4)
_cell_length_c                   13.6374(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1097.91(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1117
_cell_measurement_theta_min      4.232
_cell_measurement_theta_max      22.2390

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92966
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1827
_diffrn_reflns_number            10062
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.589
_diffrn_reflns_theta_max         29.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_point_group_measured_fraction_full 0.870
_reflns_number_total             2644
_reflns_number_gt                1685
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.586
_reflns_Friedel_fraction_max     0.634
_reflns_Friedel_fraction_full    0.730

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0715P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 442 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2644
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1603
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.003
_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
O1 O 0.71945(18) 0.6064(8) 0.4159(2) 0.0790(10) Uani 1 1 d . . . . .
O2 O 0.61252(14) 0.0832(8) 0.7035(2) 0.0691(9) Uani 1 1 d . . . . .
O3 O 0.56335(13) 0.5462(5) 0.4900(2) 0.0559(7) Uani 1 1 d . . . . .
O4 O 0.44663(15) 0.3053(8) 0.4156(3) 0.0785(9) Uani 1 1 d . . . . .
O5 O 0.49853(16) 0.0591(7) 0.2911(2) 0.0654(8) Uani 1 1 d . . . . .
H5O H 0.458(3) 0.017(10) 0.264(4) 0.075(14) Uiso 1 1 d . . . . .
N1 N 0.67089(15) 0.3270(7) 0.5798(2) 0.0502(7) Uani 1 1 d . . . . .
H1N H 0.665(2) 0.431(12) 0.522(4) 0.075(13) Uiso 1 1 d . . . . .
C1 C 0.73581(17) 0.2393(8) 0.6047(3) 0.0484(8) Uani 1 1 d . . . . .
C2 C 0.7527(2) 0.0773(9) 0.6905(3) 0.0560(9) Uani 1 1 d . . . . .
H2 H 0.721040 0.020945 0.736582 0.067 Uiso 1 1 calc R U . . .
C3 C 0.8177(2) -0.0002(11) 0.7071(3) 0.0637(10) Uani 1 1 d . . . . .
H3 H 0.829091 -0.109191 0.765189 0.076 Uiso 1 1 calc R U . . .
C4 C 0.8654(2) 0.0773(10) 0.6416(3) 0.0669(11) Uani 1 1 d . . . . .
H4 H 0.908676 0.021475 0.654726 0.080 Uiso 1 1 calc R U . . .
C5 C 0.8492(2) 0.2377(10) 0.5565(3) 0.0631(10) Uani 1 1 d . . . . .
H5 H 0.881727 0.293212 0.511705 0.076 Uiso 1 1 calc R U . . .
C6 C 0.78484(19) 0.3194(9) 0.5358(3) 0.0524(9) Uani 1 1 d . . . . .
C7 C 0.7721(2) 0.4971(12) 0.4441(4) 0.0685(11) Uani 1 1 d . . . . .
H7 H 0.807667 0.530831 0.402716 0.082 Uiso 1 1 calc R U . . .
C8 C 0.61545(18) 0.2461(8) 0.6265(3) 0.0520(9) Uani 1 1 d . . . . .
C9 C 0.55363(19) 0.3654(9) 0.5780(3) 0.0555(9) Uani 1 1 d . . . . .
H9A H 0.526422 0.168995 0.564375 0.067 Uiso 1 1 calc R U . . .
H9B H 0.530066 0.509933 0.623496 0.067 Uiso 1 1 calc R U . . .
C10 C 0.56357(17) 0.3414(9) 0.4049(3) 0.0518(8) Uani 1 1 d . . . . .
H10A H 0.589101 0.138157 0.417554 0.062 Uiso 1 1 calc R U . . .
H10B H 0.584592 0.465244 0.352147 0.062 Uiso 1 1 calc R U . . .
C11 C 0.49612(17) 0.2384(8) 0.3727(3) 0.0502(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.224(6) . ?
O2 C8 1.231(4) . ?
O3 C9 1.408(5) . ?
O3 C10 1.412(5) . ?
O4 C11 1.200(4) . ?
O5 C11 1.318(5) . ?
O5 H5O 0.93(6) . ?
N1 C8 1.340(5) . ?
N1 C1 1.415(5) . ?
N1 H1N 0.90(5) . ?
C1 C2 1.377(5) . ?
C1 C6 1.411(5) . ?
C2 C3 1.384(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.360(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.456(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.504(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.506(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O3 C10 114.4(2) . . ?
C11 O5 H5O 114(3) . . ?
C8 N1 C1 128.7(3) . . ?
C8 N1 H1N 114(3) . . ?
C1 N1 H1N 117(3) . . ?
C2 C1 C6 119.3(3) . . ?
C2 C1 N1 123.6(3) . . ?
C6 C1 N1 117.1(3) . . ?
C1 C2 C3 118.9(4) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 122.3(4) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 120.9(4) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.4(4) . . ?
C5 C6 C7 117.1(4) . . ?
C1 C6 C7 123.5(4) . . ?
O1 C7 C6 126.6(4) . . ?
O1 C7 H7 116.7 . . ?
C6 C7 H7 116.7 . . ?
O2 C8 N1 124.7(3) . . ?
O2 C8 C9 119.8(3) . . ?
N1 C8 C9 115.5(3) . . ?
O3 C9 C8 114.4(3) . . ?
O3 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
O3 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
O3 C10 C11 113.0(3) . . ?
O3 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
O3 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
O4 C11 O5 124.1(4) . . ?
O4 C11 C10 125.0(4) . . ?
O5 C11 C10 110.9(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
C8 N1 C1 C2 -7.0(6) . . . . ?
C8 N1 C1 C6 171.8(3) . . . . ?
C6 C1 C2 C3 0.5(5) . . . . ?
N1 C1 C2 C3 179.3(3) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C2 C3 C4 C5 0.2(7) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C4 C5 C6 C1 0.9(6) . . . . ?
C4 C5 C6 C7 178.8(4) . . . . ?
C2 C1 C6 C5 -0.9(5) . . . . ?
N1 C1 C6 C5 -179.8(3) . . . . ?
C2 C1 C6 C7 -178.6(3) . . . . ?
N1 C1 C6 C7 2.5(5) . . . . ?
C5 C6 C7 O1 -175.6(4) . . . . ?
C1 C6 C7 O1 2.1(7) . . . . ?
C1 N1 C8 O2 2.3(6) . . . . ?
C1 N1 C8 C9 -177.1(3) . . . . ?
C10 O3 C9 C8 90.7(4) . . . . ?
O2 C8 C9 O3 -179.5(3) . . . . ?
N1 C8 C9 O3 -0.1(5) . . . . ?
C9 O3 C10 C11 77.8(4) . . . . ?
O3 C10 C11 O4 -3.4(6) . . . . ?
O3 C10 C11 O5 177.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.90(5) 1.96(5) 2.682(4) 137(4) .
O5 H5O O2 0.93(6) 1.70(6) 2.630(4) 174(5) 2_654

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_ad37
_database_code_depnum_ccdc_archive 'CCDC 1972493'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2019-12-17 deposited with the CCDC.	2020-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 N3 O3'
_chemical_formula_weight         341.40

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

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

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

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

_cell_length_a                   11.864(3)
_cell_length_b                   11.162(3)
_cell_length_c                   13.889(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.31(3)
_cell_angle_gamma                90
_cell_volume                     1815.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    453
_cell_measurement_theta_min      3.471
_cell_measurement_theta_max      28.079

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.36107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1827
_diffrn_reflns_number            12145
_diffrn_reflns_av_unetI/netI     0.1703
_diffrn_reflns_av_R_equivalents  0.1767
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.972
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3136
_reflns_number_gt                1164
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0342P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3136
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2181
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_ref         0.1705
_refine_ls_wR_factor_gt          0.1287
_refine_ls_goodness_of_fit_ref   0.884
_refine_ls_restrained_S_all      0.884
_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
O1 O 0.5953(3) 0.8924(3) 0.6013(2) 0.0767(11) Uani 1 1 d . . . . .
O2 O 0.7024(3) 0.9930(3) 0.5130(2) 0.0704(10) Uani 1 1 d . . . . .
O3 O 0.1779(3) 0.6125(3) 0.2951(3) 0.0921(14) Uani 1 1 d . . . . .
N1 N 0.3253(3) 0.8603(3) 0.3124(3) 0.0538(10) Uani 1 1 d . . . . .
H1N H 0.313309 0.913100 0.354750 0.065 Uiso 1 1 calc R U . . .
N2 N 0.4020(3) 0.6798(3) 0.2812(3) 0.0511(10) Uani 1 1 d . . . . .
N3 N 0.1821(3) 0.4954(3) 0.1628(3) 0.0616(11) Uani 1 1 d . . . . .
H3N H 0.216336 0.485659 0.113275 0.074 Uiso 1 1 calc R U . . .
C1 C 0.3145(4) 0.6603(4) 0.1936(3) 0.0514(12) Uani 1 1 d . . . . .
H1 H 0.348755 0.617653 0.143797 0.062 Uiso 1 1 calc R U . . .
C2 C 0.2679(4) 0.7790(4) 0.1534(3) 0.0494(12) Uani 1 1 d . . . . .
C3 C 0.2204(4) 0.7911(5) 0.0560(3) 0.0602(14) Uani 1 1 d . . . . .
H3 H 0.219256 0.726571 0.013476 0.072 Uiso 1 1 calc R U . . .
C4 C 0.1752(5) 0.8994(5) 0.0230(4) 0.0796(17) Uani 1 1 d . . . . .
H4 H 0.143566 0.908350 -0.042374 0.096 Uiso 1 1 calc R U . . .
C5 C 0.1761(5) 0.9948(5) 0.0855(4) 0.0778(16) Uani 1 1 d . . . . .
H5 H 0.144496 1.067567 0.062358 0.093 Uiso 1 1 calc R U . . .
C6 C 0.2238(4) 0.9832(4) 0.1828(4) 0.0672(15) Uani 1 1 d . . . . .
H6 H 0.225044 1.047587 0.225452 0.081 Uiso 1 1 calc R U . . .
C7 C 0.2696(4) 0.8736(4) 0.2149(3) 0.0515(12) Uani 1 1 d . . . . .
C8 C 0.3948(4) 0.7702(4) 0.3411(3) 0.0507(12) Uani 1 1 d . . . . .
C9 C 0.4672(4) 0.7808(4) 0.4388(3) 0.0541(13) Uani 1 1 d . . . . .
H9A H 0.482534 0.701409 0.466132 0.065 Uiso 1 1 calc R U . . .
H9B H 0.425821 0.825238 0.481924 0.065 Uiso 1 1 calc R U . . .
C10 C 0.5806(4) 0.8439(5) 0.4341(3) 0.0671(15) Uani 1 1 d . . . . .
H10A H 0.635930 0.784159 0.422007 0.081 Uiso 1 1 calc R U . . .
H10B H 0.569631 0.898214 0.378874 0.081 Uiso 1 1 calc R U . . .
C11 C 0.6305(4) 0.9143(4) 0.5244(4) 0.0541(13) Uani 1 1 d . . . . .
C12 C 0.4941(4) 0.5907(4) 0.3015(3) 0.0626(14) Uani 1 1 d . . . . .
H12A H 0.531712 0.583561 0.244759 0.075 Uiso 1 1 calc R U . . .
H12B H 0.550291 0.618925 0.355384 0.075 Uiso 1 1 calc R U . . .
C13 C 0.4538(4) 0.4729(5) 0.3258(4) 0.0635(15) Uani 1 1 d . . . . .
C14 C 0.4302(5) 0.3769(5) 0.3427(4) 0.0780(17) Uani 1 1 d . . . . .
H14 H 0.410866 0.298710 0.356410 0.094 Uiso 1 1 calc R U . . .
C15 C 0.2166(4) 0.5851(4) 0.2223(3) 0.0597(14) Uani 1 1 d . . . . .
C16 C 0.0894(5) 0.4099(5) 0.1741(5) 0.0795(17) Uani 1 1 d . . . . .
C17 C 0.1152(7) 0.3475(7) 0.2719(6) 0.186(4) Uani 1 1 d . . . . .
H17A H 0.186715 0.306007 0.276713 0.279 Uiso 1 1 calc R U . . .
H17B H 0.055511 0.291206 0.277746 0.279 Uiso 1 1 calc R U . . .
H17C H 0.119604 0.405815 0.323172 0.279 Uiso 1 1 calc R U . . .
C18 C 0.0851(6) 0.3206(6) 0.0923(6) 0.161(4) Uani 1 1 d . . . . .
H18A H 0.071444 0.361865 0.030908 0.242 Uiso 1 1 calc R U . . .
H18B H 0.024460 0.264456 0.095430 0.242 Uiso 1 1 calc R U . . .
H18C H 0.156473 0.278617 0.098570 0.242 Uiso 1 1 calc R U . . .
C19 C -0.0233(5) 0.4743(5) 0.1614(5) 0.122(3) Uani 1 1 d . . . . .
H19A H -0.018834 0.539968 0.206490 0.184 Uiso 1 1 calc R U . . .
H19B H -0.082049 0.419874 0.173558 0.184 Uiso 1 1 calc R U . . .
H19C H -0.041136 0.504310 0.095870 0.184 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
O1 C11 1.233(5) . ?
O2 C11 1.252(5) . ?
O3 C15 1.215(5) . ?
N1 C8 1.321(5) . ?
N1 C7 1.415(5) . ?
N1 H1N 0.8600 . ?
N2 C8 1.319(5) . ?
N2 C12 1.471(5) . ?
N2 C1 1.483(5) . ?
N3 C15 1.321(5) . ?
N3 C16 1.483(6) . ?
N3 H3N 0.8600 . ?
C1 C2 1.507(6) . ?
C1 C15 1.537(6) . ?
C1 H1 0.9800 . ?
C2 C7 1.357(6) . ?
C2 C3 1.386(6) . ?
C3 C4 1.371(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(6) . ?
C6 H6 0.9300 . ?
C8 C9 1.489(6) . ?
C9 C10 1.528(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.516(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C13 1.457(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.142(6) . ?
C14 H14 0.9300 . ?
C16 C19 1.504(7) . ?
C16 C18 1.506(7) . ?
C16 C17 1.512(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C7 122.7(4) . . ?
C8 N1 H1N 118.6 . . ?
C7 N1 H1N 118.6 . . ?
C8 N2 C12 121.2(4) . . ?
C8 N2 C1 121.4(4) . . ?
C12 N2 C1 117.2(4) . . ?
C15 N3 C16 125.5(4) . . ?
C15 N3 H3N 117.2 . . ?
C16 N3 H3N 117.2 . . ?
N2 C1 C2 109.9(4) . . ?
N2 C1 C15 108.9(3) . . ?
C2 C1 C15 109.2(4) . . ?
N2 C1 H1 109.6 . . ?
C2 C1 H1 109.6 . . ?
C15 C1 H1 109.6 . . ?
C7 C2 C3 120.1(5) . . ?
C7 C2 C1 119.0(4) . . ?
C3 C2 C1 120.9(4) . . ?
C4 C3 C2 119.2(5) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.7(5) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.4(5) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 118.4(5) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C2 C7 C6 121.3(5) . . ?
C2 C7 N1 118.5(4) . . ?
C6 C7 N1 120.0(4) . . ?
N2 C8 N1 119.6(4) . . ?
N2 C8 C9 123.2(4) . . ?
N1 C8 C9 117.0(4) . . ?
C8 C9 C10 112.3(4) . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 115.6(4) . . ?
C11 C10 H10A 108.4 . . ?
C9 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.4 . . ?
O1 C11 O2 125.6(5) . . ?
O1 C11 C10 118.1(4) . . ?
O2 C11 C10 116.2(4) . . ?
C13 C12 N2 113.1(4) . . ?
C13 C12 H12A 108.9 . . ?
N2 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
N2 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 174.4(6) . . ?
C13 C14 H14 180.0 . . ?
O3 C15 N3 126.2(5) . . ?
O3 C15 C1 118.9(4) . . ?
N3 C15 C1 114.9(4) . . ?
N3 C16 C19 109.9(5) . . ?
N3 C16 C18 106.3(5) . . ?
C19 C16 C18 107.8(5) . . ?
N3 C16 C17 110.2(5) . . ?
C19 C16 C17 111.9(6) . . ?
C18 C16 C17 110.5(6) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C8 N2 C1 C2 32.8(5) . . . . ?
C12 N2 C1 C2 -150.3(4) . . . . ?
C8 N2 C1 C15 -86.8(5) . . . . ?
C12 N2 C1 C15 90.1(5) . . . . ?
N2 C1 C2 C7 -26.9(6) . . . . ?
C15 C1 C2 C7 92.5(5) . . . . ?
N2 C1 C2 C3 155.3(4) . . . . ?
C15 C1 C2 C3 -85.3(5) . . . . ?
C7 C2 C3 C4 -0.2(7) . . . . ?
C1 C2 C3 C4 177.6(4) . . . . ?
C2 C3 C4 C5 -0.4(8) . . . . ?
C3 C4 C5 C6 0.6(9) . . . . ?
C4 C5 C6 C7 -0.3(8) . . . . ?
C3 C2 C7 C6 0.5(7) . . . . ?
C1 C2 C7 C6 -177.4(4) . . . . ?
C3 C2 C7 N1 -176.0(4) . . . . ?
C1 C2 C7 N1 6.2(6) . . . . ?
C5 C6 C7 C2 -0.2(7) . . . . ?
C5 C6 C7 N1 176.2(4) . . . . ?
C8 N1 C7 C2 14.2(7) . . . . ?
C8 N1 C7 C6 -162.3(4) . . . . ?
C12 N2 C8 N1 167.2(4) . . . . ?
C1 N2 C8 N1 -15.9(6) . . . . ?
C12 N2 C8 C9 -8.7(6) . . . . ?
C1 N2 C8 C9 168.2(4) . . . . ?
C7 N1 C8 N2 -9.5(7) . . . . ?
C7 N1 C8 C9 166.7(4) . . . . ?
N2 C8 C9 C10 87.8(5) . . . . ?
N1 C8 C9 C10 -88.2(5) . . . . ?
C8 C9 C10 C11 149.8(4) . . . . ?
C9 C10 C11 O1 18.1(7) . . . . ?
C9 C10 C11 O2 -159.9(4) . . . . ?
C8 N2 C12 C13 111.2(5) . . . . ?
C1 N2 C12 C13 -65.8(5) . . . . ?
C16 N3 C15 O3 -0.4(8) . . . . ?
C16 N3 C15 C1 -179.9(4) . . . . ?
N2 C1 C15 O3 46.7(6) . . . . ?
C2 C1 C15 O3 -73.3(6) . . . . ?
N2 C1 C15 N3 -133.8(4) . . . . ?
C2 C1 C15 N3 106.2(5) . . . . ?
C15 N3 C16 C19 66.3(7) . . . . ?
C15 N3 C16 C18 -177.2(5) . . . . ?
C15 N3 C16 C17 -57.5(7) . . . . ?

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
N1 H1N O2 0.86 2.15 2.987(5) 164.8 3_676
N3 H3N O2 0.86 2.14 2.987(5) 170.4 2_645

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_ad26
_database_code_depnum_ccdc_archive 'CCDC 1968959'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2019-11-29 deposited with the CCDC.	2020-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 N O4'
_chemical_formula_weight         219.19

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                   20.522(5)
_cell_length_b                   3.8101(12)
_cell_length_c                   26.193(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.39(3)
_cell_angle_gamma                90
_cell_volume                     2000.4(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    465
_cell_measurement_theta_min      4.009
_cell_measurement_theta_max      20.807

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.03238
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1827
_diffrn_reflns_number            9140
_diffrn_reflns_av_unetI/netI     0.1078
_diffrn_reflns_av_R_equivalents  0.1005
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.391
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2930
_reflns_number_gt                933
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0940P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2930
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2002
_refine_ls_R_factor_gt           0.0758
_refine_ls_wR_factor_ref         0.2470
_refine_ls_wR_factor_gt          0.1904
_refine_ls_goodness_of_fit_ref   0.858
_refine_ls_restrained_S_all      0.858
_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
O1 O 0.56941(13) -0.0067(8) 0.53876(10) 0.0992(9) Uani 1 1 d . . . . .
O2 O 0.43111(10) 0.4394(6) 0.65667(8) 0.0822(7) Uani 1 1 d . . . . .
O3 O 0.24094(12) 0.8567(7) 0.57243(10) 0.0979(9) Uani 1 1 d . . . . .
O4 O 0.31629(12) 0.7102(8) 0.64143(9) 0.0936(8) Uani 1 1 d . . . . .
H4O H 0.352542 0.610548 0.648262 0.140 Uiso 1 1 calc R U . . .
N1 N 0.50112(11) 0.2236(6) 0.60863(9) 0.0653(7) Uani 1 1 d . . . . .
H1N H 0.504932 0.189628 0.576947 0.078 Uiso 1 1 calc R U . . .
C1 C 0.55599(14) 0.1103(8) 0.64757(12) 0.0624(8) Uani 1 1 d . . . . .
C2 C 0.55756(17) 0.1457(9) 0.69998(13) 0.0755(9) Uani 1 1 d . . . . .
H2 H 0.521610 0.245063 0.711116 0.091 Uiso 1 1 calc R U . . .
C3 C 0.61377(17) 0.0310(9) 0.73659(14) 0.0813(10) Uani 1 1 d . . . . .
H3 H 0.614872 0.055022 0.772096 0.098 Uiso 1 1 calc R U . . .
C4 C 0.66673(17) -0.1150(9) 0.72087(15) 0.0795(10) Uani 1 1 d . . . . .
H4 H 0.703832 -0.188423 0.745560 0.095 Uiso 1 1 calc R U . . .
C5 C 0.66533(16) -0.1537(8) 0.66858(15) 0.0765(9) Uani 1 1 d . . . . .
H5 H 0.701560 -0.254180 0.657982 0.092 Uiso 1 1 calc R U . . .
C6 C 0.61014(14) -0.0441(8) 0.63121(12) 0.0633(8) Uani 1 1 d . . . . .
C7 C 0.61205(17) -0.0918(9) 0.57696(15) 0.0801(10) Uani 1 1 d . . . . .
H7 H 0.650011 -0.199456 0.570241 0.096 Uiso 1 1 calc R U . . .
C8 C 0.44366(15) 0.3773(8) 0.61392(12) 0.0634(8) Uani 1 1 d . . . . .
C9 C 0.39790(15) 0.4602(8) 0.56370(11) 0.0706(9) Uani 1 1 d . . . . .
H9 H 0.413796 0.406243 0.533950 0.085 Uiso 1 1 calc R U . . .
C10 C 0.33694(16) 0.6015(9) 0.55493(13) 0.0768(10) Uani 1 1 d . . . . .
H10 H 0.317079 0.625475 0.519697 0.092 Uiso 1 1 calc R U . . .
C11 C 0.29504(17) 0.7271(9) 0.59061(14) 0.0759(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.223(4) . ?
O2 C8 1.224(3) . ?
O3 C11 1.215(4) . ?
O4 C11 1.310(4) . ?
O4 H4O 0.8200 . ?
N1 C8 1.350(4) . ?
N1 C1 1.415(4) . ?
N1 H1N 0.8600 . ?
C1 C2 1.373(4) . ?
C1 C6 1.403(4) . ?
C2 C3 1.402(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.441(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.477(4) . ?
C9 C10 1.336(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.479(4) . ?
C10 H10 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O4 H4O 109.5 . . ?
C8 N1 C1 129.5(3) . . ?
C8 N1 H1N 115.3 . . ?
C1 N1 H1N 115.3 . . ?
C2 C1 C6 119.8(3) . . ?
C2 C1 N1 122.3(3) . . ?
C6 C1 N1 117.9(3) . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 C7 117.7(3) . . ?
C1 C6 C7 123.0(3) . . ?
O1 C7 C6 127.4(3) . . ?
O1 C7 H7 116.3 . . ?
C6 C7 H7 116.3 . . ?
O2 C8 N1 122.5(3) . . ?
O2 C8 C9 123.7(3) . . ?
N1 C8 C9 113.8(3) . . ?
C10 C9 C8 129.2(3) . . ?
C10 C9 H9 115.4 . . ?
C8 C9 H9 115.4 . . ?
C9 C10 C11 132.2(3) . . ?
C9 C10 H10 113.9 . . ?
C11 C10 H10 113.9 . . ?
O3 C11 O4 119.7(3) . . ?
O3 C11 C10 119.4(3) . . ?
O4 C11 C10 120.9(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
C8 N1 C1 C2 0.1(5) . . . . ?
C8 N1 C1 C6 179.9(3) . . . . ?
C6 C1 C2 C3 0.8(5) . . . . ?
N1 C1 C2 C3 -179.4(3) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C4 C5 C6 C1 0.6(5) . . . . ?
C4 C5 C6 C7 179.8(3) . . . . ?
C2 C1 C6 C5 -1.1(5) . . . . ?
N1 C1 C6 C5 179.1(3) . . . . ?
C2 C1 C6 C7 179.7(3) . . . . ?
N1 C1 C6 C7 -0.1(4) . . . . ?
C5 C6 C7 O1 -178.4(3) . . . . ?
C1 C6 C7 O1 0.8(6) . . . . ?
C1 N1 C8 O2 -0.6(5) . . . . ?
C1 N1 C8 C9 179.7(3) . . . . ?
O2 C8 C9 C10 -1.8(6) . . . . ?
N1 C8 C9 C10 177.9(3) . . . . ?
C8 C9 C10 C11 1.1(7) . . . . ?
C9 C10 C11 O3 177.9(4) . . . . ?
C9 C10 C11 O4 0.0(6) . . . . ?

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
N1 H1N O1 0.86 1.97 2.680(3) 139.2 .
O4 H4O O2 0.82 1.71 2.524(3) 172.4 .

_refine_diff_density_max         0.238
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.053

