# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_invertida
_database_code_depnum_ccdc_archive 'CCDC 2179399'
loop_
_audit_author_name
_audit_author_address
'F. Sanz'
;Universidad de salamanca
Spain
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 N2 O2, C7 H4 N2 O6, C H4 O'
_chemical_formula_sum            'C19 H20 N4 O9'
_chemical_formula_weight         448.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_space_group_name_Hall  P2yb

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

_cell_length_a                   7.2094(4)
_cell_length_b                   7.5386(3)
_cell_length_c                   19.1587(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.214(3)
_cell_angle_gamma                90.00
_cell_volume                     1030.57(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2715
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      64.22

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468
_exptl_absorpt_coefficient_mu    0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_T_max  0.905
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7296
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         66.72
_reflns_number_total             2586
_reflns_number_gt                2369
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX 2 (Bruker 2006)'
_computing_cell_refinement       'SAINT (Bruker 2006)'
_computing_data_reduction        'SAINT (Bruker 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 4.0.0 (Macrae et al, 2008)'
_computing_publication_material  'Bruker SHELXTL'
_chemical_absolute_configuration rm

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0993P)²+0.3879P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(4)
_refine_ls_number_reflns         2586
_refine_ls_number_parameters     283
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1483
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.064
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0635(5) 0.7551(7) 0.24932(19) 0.0463(10) Uani 1 1 d . . .
H1 H 0.1799 0.7029 0.2630 0.056 Uiso 1 1 calc R . .
N1 N -0.0062(5) 0.8090(5) 0.18192(15) 0.0507(9) Uani 1 1 d . . .
H1N H 0.0517 0.7995 0.1458 0.061 Uiso 1 1 calc R . .
C2 C -0.1791(5) 0.8789(6) 0.18110(18) 0.0431(9) Uani 1 1 d . . .
C3 C -0.3068(6) 0.9460(7) 0.1257(2) 0.0529(11) Uani 1 1 d . . .
H3 H -0.2780 0.9488 0.0799 0.063 Uiso 1 1 calc R . .
C4 C -0.4742(7) 1.0071(7) 0.1404(2) 0.0602(12) Uani 1 1 d . . .
H4 H -0.5610 1.0519 0.1041 0.072 Uiso 1 1 calc R . .
C5 C -0.5196(6) 1.0040(7) 0.2104(2) 0.0602(12) Uani 1 1 d . . .
H5 H -0.6339 1.0493 0.2193 0.072 Uiso 1 1 calc R . .
C6 C -0.3966(5) 0.9349(7) 0.2647(2) 0.0484(10) Uani 1 1 d . . .
H6 H -0.4278 0.9308 0.3102 0.058 Uiso 1 1 calc R . .
C7 C -0.2239(5) 0.8707(6) 0.25100(17) 0.0400(9) Uani 1 1 d . . .
C8 C -0.0666(5) 0.7911(6) 0.29282(17) 0.0393(9) Uani 1 1 d . . .
C9 C -0.0505(5) 0.7452(6) 0.36993(17) 0.0406(9) Uani 1 1 d . . .
H9A H 0.0532 0.6636 0.3817 0.049 Uiso 1 1 calc R . .
H9B H -0.1640 0.6845 0.3783 0.049 Uiso 1 1 calc R . .
C10 C -0.0202(5) 0.9059(5) 0.41916(17) 0.0363(8) Uani 1 1 d . . .
H10 H -0.1212 0.9913 0.4052 0.044 Uiso 1 1 calc R . .
C11 C -0.0279(5) 0.8497(6) 0.49463(17) 0.0396(9) Uani 1 1 d . . .
N2 N 0.1618(4) 0.9932(5) 0.41259(15) 0.0408(8) Uani 1 1 d . . .
H2A H 0.2541 0.9143 0.4213 0.061 Uiso 1 1 calc R . .
H2B H 0.1813 1.0818 0.4434 0.061 Uiso 1 1 calc R . .
H2C H 0.1587 1.0355 0.3691 0.061 Uiso 1 1 calc R . .
C12 C 0.3266(5) 0.9358(6) 0.80831(18) 0.0424(9) Uani 1 1 d . . .
H12 H 0.4040 0.9590 0.7745 0.051 Uiso 1 1 calc R . .
O1 O 0.1216(4) 0.8489(5) 0.53662(12) 0.0550(8) Uani 1 1 d . . .
O2 O -0.1839(4) 0.7990(5) 0.50792(13) 0.0536(8) Uani 1 1 d . . .
C13 C 0.3828(5) 0.9785(6) 0.87849(19) 0.0410(9) Uani 1 1 d . . .
C14 C 0.2773(6) 0.9425(6) 0.93107(18) 0.0433(9) Uani 1 1 d . . .
H14 H 0.3191 0.9695 0.9780 0.052 Uiso 1 1 calc R . .
C15 C 0.1036(5) 0.8628(6) 0.90976(17) 0.0411(8) Uani 1 1 d . . .
C16 C 0.0400(5) 0.8202(6) 0.84130(19) 0.0418(9) Uani 1 1 d . . .
H16 H -0.0766 0.7670 0.8293 0.050 Uiso 1 1 calc R . .
C17 C 0.1523(5) 0.8575(6) 0.78947(18) 0.0406(8) Uani 1 1 d . . .
C18 C 0.0794(6) 0.8137(6) 0.71498(19) 0.0456(10) Uani 1 1 d . . .
O3 O 0.1978(4) 0.8481(5) 0.67117(13) 0.0518(7) Uani 1 1 d . . .
H3A H 0.1406 0.8596 0.6312 0.078 Uiso 1 1 calc R . .
O4 O -0.0759(4) 0.7493(5) 0.69830(15) 0.0631(9) Uani 1 1 d . . .
N3 N -0.0131(5) 0.8214(6) 0.96470(17) 0.0551(10) Uani 1 1 d . . .
O5 O -0.1645(5) 0.7510(7) 0.94692(18) 0.0850(12) Uani 1 1 d . . .
O6 O 0.0457(5) 0.8658(7) 1.02535(14) 0.0833(14) Uani 1 1 d . . .
N4 N 0.5670(4) 1.0607(6) 0.89887(17) 0.0502(9) Uani 1 1 d . . .
O7 O 0.6090(5) 1.1099(6) 0.95982(16) 0.0726(11) Uani 1 1 d . . .
O8 O 0.6695(4) 1.0782(6) 0.85359(16) 0.0721(11) Uani 1 1 d . . .
O9 O -0.5289(5) 0.7626(7) 0.42540(19) 0.0804(10) Uiso 1 1 d D . .
H9 H -0.4946 0.7717 0.4679 0.121 Uiso 1 1 calc R . .
C19 C -0.5482(14) 0.5716(15) 0.4059(5) 0.153(4) Uiso 1 1 d D . .
H19A H -0.4347 0.5101 0.4239 0.230 Uiso 1 1 calc R . .
H19B H -0.5711 0.5605 0.3555 0.230 Uiso 1 1 calc R . .
H19C H -0.6510 0.5212 0.4259 0.230 Uiso 1 1 calc R . .


_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 C8 1.367(5) . ?
C1 N1 1.378(5) . ?
C1 H1 0.9300 . ?
N1 C2 1.352(5) . ?
N1 H1N 0.8600 . ?
C2 C3 1.397(6) . ?
C2 C7 1.423(5) . ?
C3 C4 1.359(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.425(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.395(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.424(5) . ?
C8 C9 1.506(5) . ?
C9 C10 1.532(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.489(5) . ?
C10 C11 1.515(5) . ?
C10 H10 0.9800 . ?
C11 O2 1.248(5) . ?
C11 O1 1.250(4) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C12 C13 1.386(5) . ?
C12 C17 1.389(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(5) . ?
C13 N4 1.467(5) . ?
C14 C15 1.397(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(5) . ?
C15 N3 1.472(5) . ?
C16 C17 1.397(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.486(5) . ?
C18 O4 1.220(5) . ?
C18 O3 1.306(5) . ?
O3 H3A 0.8200 . ?
N3 O5 1.217(5) . ?
N3 O6 1.225(4) . ?
N4 O7 1.221(4) . ?
N4 O8 1.224(4) . ?
O9 C19 1.489(12) . ?
O9 H9 0.8200 . ?
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 C1 N1 108.8(3) . . ?
C8 C1 H1 125.6 . . ?
N1 C1 H1 125.6 . . ?
C2 N1 C1 109.7(3) . . ?
C2 N1 H1N 125.1 . . ?
C1 N1 H1N 125.1 . . ?
N1 C2 C3 131.1(3) . . ?
N1 C2 C7 107.8(3) . . ?
C3 C2 C7 121.1(4) . . ?
C4 C3 C2 118.3(4) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 121.3(4) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.1(4) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C2 119.4(3) . . ?
C6 C7 C8 134.5(3) . . ?
C2 C7 C8 106.1(3) . . ?
C1 C8 C7 107.5(3) . . ?
C1 C8 C9 126.1(3) . . ?
C7 C8 C9 126.3(3) . . ?
C8 C9 C10 114.0(3) . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.6 . . ?
N2 C10 C11 110.9(3) . . ?
N2 C10 C9 110.3(3) . . ?
C11 C10 C9 110.2(3) . . ?
N2 C10 H10 108.5 . . ?
C11 C10 H10 108.5 . . ?
C9 C10 H10 108.5 . . ?
O2 C11 O1 125.9(3) . . ?
O2 C11 C10 115.9(3) . . ?
O1 C11 C10 118.0(3) . . ?
C10 N2 H2A 109.5 . . ?
C10 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C10 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C13 C12 C17 118.7(3) . . ?
C13 C12 H12 120.7 . . ?
C17 C12 H12 120.7 . . ?
C14 C13 C12 123.3(4) . . ?
C14 C13 N4 117.6(3) . . ?
C12 C13 N4 119.0(3) . . ?
C13 C14 C15 116.0(3) . . ?
C13 C14 H14 122.0 . . ?
C15 C14 H14 122.0 . . ?
C16 C15 C14 123.1(3) . . ?
C16 C15 N3 119.3(4) . . ?
C14 C15 N3 117.6(3) . . ?
C15 C16 C17 119.1(4) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C12 C17 C16 119.7(3) . . ?
C12 C17 C18 121.8(3) . . ?
C16 C17 C18 118.5(4) . . ?
O4 C18 O3 124.8(3) . . ?
O4 C18 C17 121.7(4) . . ?
O3 C18 C17 113.5(3) . . ?
C18 O3 H3A 109.5 . . ?
O5 N3 O6 124.0(3) . . ?
O5 N3 C15 118.3(3) . . ?
O6 N3 C15 117.7(4) . . ?
O7 N4 O8 123.5(4) . . ?
O7 N4 C13 118.3(3) . . ?
O8 N4 C13 118.2(3) . . ?
C19 O9 H9 109.5 . . ?
O9 C19 H19A 109.5 . . ?
O9 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O9 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.946
_diffrn_reflns_theta_full        66.72
_diffrn_measured_fraction_theta_full 0.946
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_1fin
_database_code_depnum_ccdc_archive 'CCDC 2179405'
loop_
_audit_author_name
_audit_author_address
'F. Sanz'
;Universidad de salamanca
Spain
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_1fin                
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.883 Why?
RESPONSE: Due to geometrical constraints of the instrument and the use of copper radiation, we obtain consistently a data completeness lower than 100% in dependence of the crystal system and the orientation of  the mounted crystal, even with appropriate data collection routines.  Typical values for data completeness range from 83-92% for triclinic, 85-97% for monoclinic and 85-98% for all other crystal systems.
;
# Added during the CSD deposition process: Wednesday 15 June 2022 06:01 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H6 N2 O8, 2(C11 H13 N2 O2), 2(O)'
_chemical_formula_sum            'C36 H32 N6 O14'
_chemical_formula_weight         772.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1
_symmetry_space_group_name_Hall  P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   8.3904(3)
_cell_length_b                   9.2903(3)
_cell_length_c                   11.4586(4)
_cell_angle_alpha                77.406(2)
_cell_angle_beta                 89.956(2)
_cell_angle_gamma                77.501(2)
_cell_volume                     850.03(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4266
_cell_measurement_theta_min      3.96
_cell_measurement_theta_max      66.40

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             402
_exptl_absorpt_coefficient_mu    1.006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.860
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5774
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.96
_diffrn_reflns_theta_max         66.66
_reflns_number_total             3144
_reflns_number_gt                2958
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX 2 (Bruker 2006)'
_computing_cell_refinement       'SAINT (Bruker 2006)'
_computing_data_reduction        'SAINT (Bruker 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 4.0.0 (Macrae et al, 2008)'
_computing_publication_material  'Bruker SHELXTL'
_chemical_absolute_configuration rm

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0711P)²+0.1891P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0102(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_number_reflns         3144
_refine_ls_number_parameters     510
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.076
_refine_ls_shift/su_mean         0.015

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6496(7) 0.6612(6) -0.1308(4) 0.0298(11) Uani 1 1 d . . .
C2 C 0.5891(6) 0.5279(5) -0.1503(4) 0.0252(10) Uani 1 1 d . . .
C3 C 0.5206(6) 0.5072(5) -0.2541(5) 0.0299(11) Uani 1 1 d . . .
H3 H 0.5027 0.5801 -0.3255 0.036 Uiso 1 1 calc R . .
C4 C 0.4815(7) 0.3664(6) -0.2406(4) 0.0291(10) Uani 1 1 d . . .
C5 C 0.4067(6) 0.3019(6) -0.3287(4) 0.0292(11) Uani 1 1 d . . .
C6 C 0.4485(7) 0.1234(6) -0.1522(5) 0.0322(11) Uani 1 1 d . . .
C7 C 0.5071(7) 0.2576(6) -0.1339(5) 0.0308(11) Uani 1 1 d . . .
C8 C 0.5721(7) 0.2820(6) -0.0317(4) 0.0330(12) Uani 1 1 d . . .
H8 H 0.5878 0.2100 0.0401 0.040 Uiso 1 1 calc R . .
C9 C 0.6127(6) 0.4210(6) -0.0428(4) 0.0256(10) Uani 1 1 d . . .
C10 C 0.6868(6) 0.4843(6) 0.0491(4) 0.0268(11) Uani 1 1 d . . .
C11 C 0.3190(7) 0.0616(6) -0.3276(5) 0.0333(12) Uani 1 1 d . . .
H11A H 0.2079 0.1158 -0.3534 0.040 Uiso 1 1 calc R . .
H11B H 0.3126 -0.0274 -0.2667 0.040 Uiso 1 1 calc R . .
C12 C 0.4024(6) 0.0105(5) -0.4333(4) 0.0275(10) Uani 1 1 d . . .
C13 C 0.7787(7) 0.7235(6) 0.0463(5) 0.0341(12) Uani 1 1 d . . .
H13A H 0.7883 0.8123 -0.0137 0.041 Uiso 1 1 calc R . .
H13B H 0.8885 0.6678 0.0743 0.041 Uiso 1 1 calc R . .
C14 C 0.6904(6) 0.7745(5) 0.1505(4) 0.0245(10) Uani 1 1 d . . .
C15 C -0.2059(8) 0.3908(7) 0.4467(6) 0.0446(14) Uani 1 1 d . . .
H15 H -0.2373 0.4382 0.3674 0.053 Uiso 1 1 calc R . .
C16 C -0.1790(7) 0.2211(7) 0.6149(6) 0.0369(12) Uani 1 1 d . . .
C17 C -0.1768(7) 0.0944(7) 0.7072(7) 0.0439(14) Uani 1 1 d . . .
H17 H -0.2303 0.0200 0.6966 0.053 Uiso 1 1 calc R . .
C18 C -0.0947(8) 0.0815(7) 0.8139(7) 0.0490(16) Uani 1 1 d . . .
H18 H -0.0952 -0.0013 0.8764 0.059 Uiso 1 1 calc R . .
C19 C -0.0087(8) 0.1924(8) 0.8306(6) 0.0492(15) Uani 1 1 d . . .
H19 H 0.0472 0.1815 0.9031 0.059 Uiso 1 1 calc R . .
C20 C -0.0087(7) 0.3192(6) 0.7362(5) 0.0352(12) Uani 1 1 d . . .
H20 H 0.0474 0.3918 0.7469 0.042 Uiso 1 1 calc R . .
C21 C -0.0913(6) 0.3357(6) 0.6284(5) 0.0289(10) Uani 1 1 d . . .
C22 C -0.1131(7) 0.4410(6) 0.5180(5) 0.0347(12) Uani 1 1 d . . .
C23 C -0.0353(7) 0.5776(6) 0.4845(6) 0.0362(12) Uani 1 1 d . . .
H23A H -0.0258 0.6017 0.3984 0.043 Uiso 1 1 calc R . .
H23B H 0.0743 0.5506 0.5213 0.043 Uiso 1 1 calc R . .
C24 C -0.1323(6) 0.7222(6) 0.5234(4) 0.0291(10) Uani 1 1 d . . .
H24 H -0.1551 0.6955 0.6084 0.035 Uiso 1 1 calc R . .
C25 C -0.0387(6) 0.8458(6) 0.5040(4) 0.0290(10) Uani 1 1 d . . .
C26 C 0.3020(8) 0.3907(6) 0.2735(6) 0.0399(13) Uani 1 1 d . . .
H26 H 0.3356 0.3405 0.3519 0.048 Uiso 1 1 calc R . .
C27 C 0.2688(7) 0.5639(6) 0.0985(6) 0.0332(11) Uani 1 1 d . . .
C28 C 0.2703(7) 0.6921(7) 0.0096(6) 0.0408(14) Uani 1 1 d . . .
H28 H 0.3250 0.7655 0.0207 0.049 Uiso 1 1 calc R . .
C29 C 0.1859(8) 0.7029(8) -0.0951(6) 0.0462(14) Uani 1 1 d . . .
H29 H 0.1817 0.7877 -0.1567 0.055 Uiso 1 1 calc R . .
C30 C 0.1070(9) 0.5938(8) -0.1131(5) 0.0455(15) Uani 1 1 d . . .
H30 H 0.0549 0.6050 -0.1872 0.055 Uiso 1 1 calc R . .
C31 C 0.1034(7) 0.4711(7) -0.0261(5) 0.0421(13) Uani 1 1 d . . .
H31 H 0.0477 0.3990 -0.0384 0.051 Uiso 1 1 calc R . .
C32 C 0.1871(6) 0.4554(6) 0.0851(5) 0.0328(11) Uani 1 1 d . . .
C33 C 0.2054(7) 0.3442(6) 0.1988(5) 0.0330(11) Uani 1 1 d . . .
C34 C 0.1315(7) 0.2107(6) 0.2297(5) 0.0360(12) Uani 1 1 d . . .
H34A H 0.0223 0.2372 0.1923 0.043 Uiso 1 1 calc R . .
H34B H 0.1211 0.1858 0.3157 0.043 Uiso 1 1 calc R . .
C35 C 0.2270(6) 0.0715(5) 0.1918(4) 0.0288(11) Uani 1 1 d . . .
H35 H 0.2467 0.0980 0.1063 0.035 Uiso 1 1 calc R . .
C36 C 0.1296(6) -0.0544(6) 0.2143(4) 0.0277(10) Uani 1 1 d . . .
N1 N 0.7002(5) 0.6287(5) -0.0104(4) 0.0281(9) Uani 1 1 d . . .
N2 N 0.3969(5) 0.1573(5) -0.2737(4) 0.0302(9) Uani 1 1 d . . .
N3 N -0.2477(6) 0.2611(6) 0.5062(5) 0.0434(12) Uani 1 1 d . . .
H3N H -0.3093 0.2133 0.4772 0.052 Uiso 1 1 calc R . .
N4 N -0.2882(6) 0.7789(5) 0.4519(4) 0.0329(10) Uani 1 1 d . . .
H4A H -0.3449 0.8603 0.4741 0.049 Uiso 1 1 calc R . .
H4B H -0.3456 0.7073 0.4636 0.049 Uiso 1 1 calc R . .
H4C H -0.2680 0.8032 0.3746 0.049 Uiso 1 1 calc R . .
N5 N 0.3411(6) 0.5219(6) 0.2146(5) 0.0442(12) Uani 1 1 d . . .
H5N H 0.4007 0.5711 0.2441 0.053 Uiso 1 1 calc R . .
N6 N 0.3874(5) 0.0063(5) 0.2610(4) 0.0257(8) Uani 1 1 d . . .
H6A H 0.4453 0.0772 0.2540 0.039 Uiso 1 1 calc R . .
H6B H 0.4424 -0.0706 0.2322 0.039 Uiso 1 1 calc R . .
H6C H 0.3696 -0.0264 0.3378 0.039 Uiso 1 1 calc R . .
O1 O 0.6584(6) 0.7758(4) -0.2044(4) 0.0473(11) Uani 1 1 d . . .
O2 O 0.3610(5) 0.3639(4) -0.4329(3) 0.0365(9) Uani 1 1 d . . .
O3 O 0.4404(6) 0.0128(5) -0.0802(3) 0.0475(11) Uani 1 1 d . . .
O4 O 0.7363(5) 0.4264(5) 0.1497(3) 0.0400(9) Uani 1 1 d . . .
O5 O 0.5425(4) 0.0282(4) -0.4563(3) 0.0367(9) Uani 1 1 d . . .
O6 O 0.3186(5) -0.0492(5) -0.4937(3) 0.0412(9) Uani 1 1 d . . .
O7 O 0.5510(4) 0.7589(4) 0.1738(3) 0.0322(8) Uani 1 1 d . . .
O8 O 0.7722(5) 0.8377(5) 0.2091(3) 0.0413(10) Uani 1 1 d . . .
O9 O 0.1012(5) 0.8040(5) 0.5700(4) 0.0430(10) Uani 1 1 d . . .
H9O H 0.1630 0.8586 0.5419 0.064 Uiso 1 1 calc R . .
O10 O -0.0817(5) 0.9634(4) 0.4308(4) 0.0381(9) Uani 1 1 d . . .
O11 O -0.0016(5) -0.0144(5) 0.1455(4) 0.0416(10) Uani 1 1 d . . .
H11O H -0.0525 -0.0819 0.1587 0.062 Uiso 1 1 calc R . .
O12 O 0.1756(5) -0.1731(4) 0.2843(3) 0.0363(9) Uani 1 1 d . . .
O13 O 0.6484(5) 0.1543(4) 0.2754(4) 0.0467(11) Uani 1 1 d . . .
O14 O -0.5537(5) 0.6266(5) 0.4441(4) 0.0437(10) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.222(6) . ?
C1 N1 1.392(7) . ?
C1 C2 1.495(7) . ?
C2 C9 1.387(7) . ?
C2 C3 1.390(7) . ?
C3 C4 1.393(7) . ?
C3 H3 0.9300 . ?
C4 C7 1.389(8) . ?
C4 C5 1.483(7) . ?
C5 O2 1.229(6) . ?
C5 N2 1.374(6) . ?
C6 O3 1.183(7) . ?
C6 N2 1.405(7) . ?
C6 C7 1.490(7) . ?
C7 C8 1.375(7) . ?
C8 C9 1.384(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.507(6) . ?
C10 O4 1.194(6) . ?
C10 N1 1.394(6) . ?
C11 N2 1.446(7) . ?
C11 C12 1.513(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O5 1.242(6) . ?
C12 O6 1.272(6) . ?
C13 N1 1.460(6) . ?
C13 C14 1.515(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O7 1.231(6) . ?
C14 O8 1.270(6) . ?
C15 C22 1.348(8) . ?
C15 N3 1.365(8) . ?
C15 H15 0.9300 . ?
C16 N3 1.314(9) . ?
C16 C17 1.397(9) . ?
C16 C21 1.453(7) . ?
C17 C18 1.373(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.424(11) . ?
C18 H18 0.9300 . ?
C19 C20 1.415(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.405(8) . ?
C22 C23 1.526(7) . ?
C23 C24 1.566(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 N4 1.475(7) . ?
C24 C25 1.504(7) . ?
C24 H24 0.9800 . ?
C25 O10 1.207(7) . ?
C25 O9 1.333(6) . ?
C26 N5 1.364(8) . ?
C26 C33 1.375(8) . ?
C26 H26 0.9300 . ?
C27 C32 1.369(8) . ?
C27 C28 1.390(8) . ?
C27 N5 1.402(8) . ?
C28 C29 1.368(9) . ?
C28 H28 0.9300 . ?
C29 C30 1.375(10) . ?
C29 H29 0.9300 . ?
C30 C31 1.347(9) . ?
C30 H30 0.9300 . ?
C31 C32 1.419(8) . ?
C31 H31 0.9300 . ?
C32 C33 1.460(8) . ?
C33 C34 1.480(8) . ?
C34 C35 1.516(9) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 N6 1.498(6) . ?
C35 C36 1.543(6) . ?
C35 H35 0.9800 . ?
C36 O12 1.200(7) . ?
C36 O11 1.292(7) . ?
N3 H3N 0.8600 . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 H4C 0.8900 . ?
N5 H5N 0.8600 . ?
N6 H6A 0.8900 . ?
N6 H6B 0.8900 . ?
N6 H6C 0.8900 . ?
O9 H9O 0.8200 . ?
O11 H11O 0.8200 . ?

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
O1 C1 N1 125.4(5) . . ?
O1 C1 C2 128.1(5) . . ?
N1 C1 C2 106.5(4) . . ?
C9 C2 C3 123.6(4) . . ?
C9 C2 C1 107.6(4) . . ?
C3 C2 C1 128.8(4) . . ?
C2 C3 C4 113.3(4) . . ?
C2 C3 H3 123.4 . . ?
C4 C3 H3 123.3 . . ?
C7 C4 C3 123.6(4) . . ?
C7 C4 C5 106.7(4) . . ?
C3 C4 C5 129.8(5) . . ?
O2 C5 N2 124.8(5) . . ?
O2 C5 C4 127.2(5) . . ?
N2 C5 C4 107.9(4) . . ?
O3 C6 N2 126.2(5) . . ?
O3 C6 C7 128.2(5) . . ?
N2 C6 C7 105.5(4) . . ?
C8 C7 C4 122.0(5) . . ?
C8 C7 C6 129.3(5) . . ?
C4 C7 C6 108.6(4) . . ?
C7 C8 C9 115.6(4) . . ?
C7 C8 H8 122.2 . . ?
C9 C8 H8 122.2 . . ?
C8 C9 C2 121.9(4) . . ?
C8 C9 C10 129.8(5) . . ?
C2 C9 C10 108.3(4) . . ?
O4 C10 N1 124.2(4) . . ?
O4 C10 C9 130.2(5) . . ?
N1 C10 C9 105.4(4) . . ?
N2 C11 C12 115.6(4) . . ?
N2 C11 H11A 108.4 . . ?
C12 C11 H11A 108.4 . . ?
N2 C11 H11B 108.4 . . ?
C12 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
O5 C12 O6 124.5(5) . . ?
O5 C12 C11 120.5(4) . . ?
O6 C12 C11 115.1(5) . . ?
N1 C13 C14 114.8(4) . . ?
N1 C13 H13A 108.6 . . ?
C14 C13 H13A 108.5 . . ?
N1 C13 H13B 108.6 . . ?
C14 C13 H13B 108.6 . . ?
H13A C13 H13B 107.5 . . ?
O7 C14 O8 123.6(5) . . ?
O7 C14 C13 122.8(4) . . ?
O8 C14 C13 113.6(4) . . ?
C22 C15 N3 111.1(5) . . ?
C22 C15 H15 124.4 . . ?
N3 C15 H15 124.4 . . ?
N3 C16 C17 131.3(6) . . ?
N3 C16 C21 107.4(5) . . ?
C17 C16 C21 121.2(6) . . ?
C18 C17 C16 119.0(6) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 121.2(6) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C20 C19 C18 119.7(6) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C21 C20 C19 120.4(5) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 135.5(5) . . ?
C20 C21 C16 118.5(5) . . ?
C22 C21 C16 106.0(5) . . ?
C15 C22 C21 106.2(5) . . ?
C15 C22 C23 127.6(6) . . ?
C21 C22 C23 126.1(5) . . ?
C22 C23 C24 114.2(4) . . ?
C22 C23 H23A 108.7 . . ?
C24 C23 H23A 108.7 . . ?
C22 C23 H23B 108.7 . . ?
C24 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
N4 C24 C25 108.5(4) . . ?
N4 C24 C23 108.8(4) . . ?
C25 C24 C23 111.8(4) . . ?
N4 C24 H24 109.2 . . ?
C25 C24 H24 109.2 . . ?
C23 C24 H24 109.2 . . ?
O10 C25 O9 125.1(5) . . ?
O10 C25 C24 123.1(5) . . ?
O9 C25 C24 111.7(4) . . ?
N5 C26 C33 109.4(5) . . ?
N5 C26 H26 125.3 . . ?
C33 C26 H26 125.3 . . ?
C32 C27 C28 123.4(6) . . ?
C32 C27 N5 107.6(5) . . ?
C28 C27 N5 128.9(5) . . ?
C29 C28 C27 115.5(5) . . ?
C29 C28 H28 122.3 . . ?
C27 C28 H28 122.3 . . ?
C28 C29 C30 122.7(6) . . ?
C28 C29 H29 118.6 . . ?
C30 C29 H29 118.6 . . ?
C31 C30 C29 121.6(6) . . ?
C31 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?
C30 C31 C32 118.0(5) . . ?
C30 C31 H31 121.0 . . ?
C32 C31 H31 121.0 . . ?
C27 C32 C31 118.8(5) . . ?
C27 C32 C33 107.6(5) . . ?
C31 C32 C33 133.6(5) . . ?
C26 C33 C32 106.1(5) . . ?
C26 C33 C34 126.5(5) . . ?
C32 C33 C34 127.4(5) . . ?
C33 C34 C35 114.5(5) . . ?
C33 C34 H34A 108.6 . . ?
C35 C34 H34A 108.6 . . ?
C33 C34 H34B 108.6 . . ?
C35 C34 H34B 108.6 . . ?
H34A C34 H34B 107.6 . . ?
N6 C35 C34 112.5(4) . . ?
N6 C35 C36 106.5(4) . . ?
C34 C35 C36 110.2(4) . . ?
N6 C35 H35 109.2 . . ?
C34 C35 H35 109.2 . . ?
C36 C35 H35 109.2 . . ?
O12 C36 O11 126.3(5) . . ?
O12 C36 C35 123.2(5) . . ?
O11 C36 C35 110.5(4) . . ?
C1 N1 C10 112.2(4) . . ?
C1 N1 C13 125.2(5) . . ?
C10 N1 C13 122.2(4) . . ?
C5 N2 C6 111.1(4) . . ?
C5 N2 C11 124.4(4) . . ?
C6 N2 C11 123.8(5) . . ?
C16 N3 C15 109.2(5) . . ?
C16 N3 H3N 125.4 . . ?
C15 N3 H3N 125.4 . . ?
C24 N4 H4A 109.5 . . ?
C24 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
C24 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C26 N5 C27 109.3(5) . . ?
C26 N5 H5N 125.4 . . ?
C27 N5 H5N 125.4 . . ?
C35 N6 H6A 109.5 . . ?
C35 N6 H6B 109.5 . . ?
H6A N6 H6B 109.5 . . ?
C35 N6 H6C 109.5 . . ?
H6A N6 H6C 109.5 . . ?
H6B N6 H6C 109.5 . . ?
C25 O9 H9O 109.5 . . ?
C36 O11 H11O 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.883
_diffrn_reflns_theta_full        66.66
_diffrn_measured_fraction_theta_full 0.883
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_14fin
_database_code_depnum_ccdc_archive 'CCDC 2179404'
loop_
_audit_author_name
_audit_author_address
'F. Sanz'
;Universidad de salamanca
Spain
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H2 N3 O8, C11 H13 N2 O2'
_chemical_formula_sum            'C18 H15 N5 O10'
_chemical_formula_weight         461.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  -P2ybc

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

_cell_length_a                   6.9989(2)
_cell_length_b                   9.8927(3)
_cell_length_c                   28.2400(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.0060(10)
_cell_angle_gamma                90.00
_cell_volume                     1940.68(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6456
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      66.15

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    1.140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_T_max  0.872
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13813
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         67.10
_reflns_number_total             3262
_reflns_number_gt                2955
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX 2 (Bruker 2006)'
_computing_cell_refinement       'SAINT (Bruker 2006)'
_computing_data_reduction        'SAINT (Bruker 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 4.0.0 (Macrae et al, 2008)'
_computing_publication_material  'Bruker SHELXTL'
_chemical_absolute_configuration rm

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0511P)²+0.6580P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3262
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.1001
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3095(3) 0.05071(19) 0.05928(7) 0.0506(4) Uani 1 1 d . . .
H1 H 0.2877 0.0586 0.0262 0.061 Uiso 1 1 calc R . .
N1 N 0.2823(2) -0.06455(16) 0.08411(6) 0.0551(4) Uani 1 1 d . . .
H1N H 0.2426 -0.1405 0.0718 0.066 Uiso 1 1 calc R . .
C2 C 0.3283(2) -0.03998(18) 0.13180(7) 0.0458(4) Uani 1 1 d . . .
C3 C 0.3242(3) -0.1248(2) 0.17114(9) 0.0631(6) Uani 1 1 d . . .
H3 H 0.2877 -0.2150 0.1676 0.076 Uiso 1 1 calc R . .
C4 C 0.3771(3) -0.0685(3) 0.21565(8) 0.0743(7) Uani 1 1 d . . .
H4 H 0.3726 -0.1214 0.2427 0.089 Uiso 1 1 calc R . .
C5 C 0.4369(3) 0.0653(3) 0.22089(7) 0.0687(6) Uani 1 1 d . . .
H5 H 0.4734 0.0995 0.2513 0.082 Uiso 1 1 calc R . .
C6 C 0.4431(3) 0.1477(2) 0.18227(6) 0.0544(5) Uani 1 1 d . . .
H6 H 0.4844 0.2368 0.1863 0.065 Uiso 1 1 calc R . .
C7 C 0.3864(2) 0.09608(17) 0.13671(6) 0.0403(4) Uani 1 1 d . . .
C8 C 0.3730(2) 0.15270(17) 0.08959(6) 0.0411(4) Uani 1 1 d . . .
C9 C 0.4194(2) 0.29317(18) 0.07514(7) 0.0452(4) Uani 1 1 d . . .
H9A H 0.4612 0.2900 0.0437 0.054 Uiso 1 1 calc R . .
H9B H 0.5261 0.3267 0.0971 0.054 Uiso 1 1 calc R . .
C10 C 0.2509(2) 0.39372(17) 0.07407(6) 0.0399(4) Uani 1 1 d . . .
H10 H 0.2234 0.4118 0.1067 0.048 Uiso 1 1 calc R . .
N2 N 0.07543(18) 0.33976(14) 0.04516(5) 0.0391(3) Uani 1 1 d . . .
H2A H -0.0132 0.4045 0.0407 0.059 Uiso 1 1 calc R . .
H2B H 0.0293 0.2706 0.0604 0.059 Uiso 1 1 calc R . .
H2C H 0.1053 0.3119 0.0170 0.059 Uiso 1 1 calc R . .
C11 C 0.3072(2) 0.52366(17) 0.05126(6) 0.0414(4) Uani 1 1 d . . .
O1 O 0.4211(2) 0.59699(14) 0.08158(5) 0.0591(4) Uani 1 1 d . . .
H1O H 0.4827 0.6495 0.0668 0.089 Uiso 1 1 calc R . .
O2 O 0.25781(17) 0.55193(13) 0.01012(4) 0.0498(3) Uani 1 1 d . . .
C12 C -0.1814(2) 0.71724(16) 0.15347(6) 0.0375(4) Uani 1 1 d . . .
C13 C -0.1688(2) 0.75014(18) 0.20129(6) 0.0406(4) Uani 1 1 d . . .
H13 H -0.1770 0.6840 0.2244 0.049 Uiso 1 1 calc R . .
C14 C -0.1437(2) 0.88390(18) 0.21361(6) 0.0406(4) Uani 1 1 d . . .
C15 C -0.1374(2) 0.98440(17) 0.18011(6) 0.0401(4) Uani 1 1 d . . .
H15 H -0.1227 1.0747 0.1890 0.048 Uiso 1 1 calc R . .
C16 C -0.1539(2) 0.94602(16) 0.13273(6) 0.0365(4) Uani 1 1 d . . .
C17 C -0.1731(2) 0.81205(16) 0.11712(6) 0.0366(4) Uani 1 1 d . . .
C18 C -0.1869(3) 0.77139(18) 0.06435(6) 0.0439(4) Uani 1 1 d . . .
O3 O -0.03381(19) 0.76230(15) 0.04709(5) 0.0602(4) Uani 1 1 d . . .
O4 O -0.35212(18) 0.75188(14) 0.04379(4) 0.0563(4) Uani 1 1 d . . .
N3 N -0.1463(2) 1.05661(15) 0.09824(5) 0.0441(3) Uani 1 1 d . . .
O5 O -0.1831(3) 1.03370(16) 0.05601(5) 0.0708(4) Uani 1 1 d . . .
O6 O -0.1009(2) 1.16853(14) 0.11396(5) 0.0645(4) Uani 1 1 d . . .
N4 N -0.1236(2) 0.91982(19) 0.26456(5) 0.0541(4) Uani 1 1 d . . .
O7 O -0.1310(2) 1.04008(17) 0.27471(5) 0.0689(4) Uani 1 1 d . . .
O8 O -0.0997(3) 0.82874(19) 0.29375(5) 0.0878(6) Uani 1 1 d . . .
N5 N -0.2018(2) 0.57183(15) 0.14215(5) 0.0458(4) Uani 1 1 d . . .
O9 O -0.2815(2) 0.50128(14) 0.16905(5) 0.0648(4) Uani 1 1 d . . .
O10 O -0.1366(2) 0.53043(14) 0.10686(5) 0.0625(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C8 1.362(3) . ?
C1 N1 1.364(3) . ?
C1 H1 0.9300 . ?
N1 C2 1.368(2) . ?
N1 H1N 0.8600 . ?
C2 C3 1.395(3) . ?
C2 C7 1.408(3) . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.396(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.436(2) . ?
C8 C9 1.495(2) . ?
C9 C10 1.540(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.4885(19) . ?
C10 C11 1.511(2) . ?
C10 H10 0.9800 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C11 O2 1.204(2) . ?
C11 O1 1.315(2) . ?
O1 H1O 0.8200 . ?
C12 C13 1.382(2) . ?
C12 C17 1.397(2) . ?
C12 N5 1.477(2) . ?
C13 C14 1.374(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(2) . ?
C14 N4 1.472(2) . ?
C15 C16 1.382(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.398(2) . ?
C16 N3 1.470(2) . ?
C17 C18 1.535(2) . ?
C18 O3 1.234(2) . ?
C18 O4 1.244(2) . ?
N3 O5 1.2104(19) . ?
N3 O6 1.220(2) . ?
N4 O8 1.219(2) . ?
N4 O7 1.226(2) . ?
N5 O9 1.216(2) . ?
N5 O10 1.2164(19) . ?

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 C1 N1 110.57(16) . . ?
C8 C1 H1 124.7 . . ?
N1 C1 H1 124.7 . . ?
C1 N1 C2 109.07(15) . . ?
C1 N1 H1N 125.5 . . ?
C2 N1 H1N 125.5 . . ?
N1 C2 C3 130.68(19) . . ?
N1 C2 C7 107.31(15) . . ?
C3 C2 C7 122.01(19) . . ?
C4 C3 C2 116.9(2) . . ?
C4 C3 H3 121.6 . . ?
C2 C3 H3 121.6 . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 118.9(2) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C6 C7 C2 119.14(17) . . ?
C6 C7 C8 133.65(17) . . ?
C2 C7 C8 107.22(15) . . ?
C1 C8 C7 105.83(16) . . ?
C1 C8 C9 125.59(16) . . ?
C7 C8 C9 128.57(15) . . ?
C8 C9 C10 114.49(14) . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
N2 C10 C11 108.17(13) . . ?
N2 C10 C9 110.95(13) . . ?
C11 C10 C9 108.60(13) . . ?
N2 C10 H10 109.7 . . ?
C11 C10 H10 109.7 . . ?
C9 C10 H10 109.7 . . ?
C10 N2 H2A 109.5 . . ?
C10 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C10 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
O2 C11 O1 125.46(16) . . ?
O2 C11 C10 123.34(15) . . ?
O1 C11 C10 111.14(14) . . ?
C11 O1 H1O 109.5 . . ?
C13 C12 C17 123.83(15) . . ?
C13 C12 N5 115.73(15) . . ?
C17 C12 N5 120.43(14) . . ?
C14 C13 C12 117.73(16) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
C13 C14 C15 122.37(15) . . ?
C13 C14 N4 118.29(16) . . ?
C15 C14 N4 119.34(16) . . ?
C14 C15 C16 117.45(15) . . ?
C14 C15 H15 121.3 . . ?
C16 C15 H15 121.3 . . ?
C15 C16 C17 124.00(15) . . ?
C15 C16 N3 115.57(14) . . ?
C17 C16 N3 120.42(14) . . ?
C12 C17 C16 114.57(14) . . ?
C12 C17 C18 122.28(14) . . ?
C16 C17 C18 123.15(14) . . ?
O3 C18 O4 127.37(16) . . ?
O3 C18 C17 116.60(15) . . ?
O4 C18 C17 116.03(14) . . ?
O5 N3 O6 122.89(16) . . ?
O5 N3 C16 119.54(15) . . ?
O6 N3 C16 117.57(14) . . ?
O8 N4 O7 124.43(16) . . ?
O8 N4 C14 118.12(17) . . ?
O7 N4 C14 117.44(17) . . ?
O9 N5 O10 124.40(16) . . ?
O9 N5 C12 117.60(14) . . ?
O10 N5 C12 117.99(15) . . ?

_diffrn_measured_fraction_theta_max 0.940
_diffrn_reflns_theta_full        67.10
_diffrn_measured_fraction_theta_full 0.940
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_14fin_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2179406'
loop_
_audit_author_name
_audit_author_address
'F. Sanz' 'Universidad de salamanca'
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O9 S, C11 H13 N2 O2, 3(H2 O)'
_chemical_formula_sum            'C17 H21 N5 O14 S'
_chemical_formula_weight         551.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  -P2ybc

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

_cell_length_a                   7.0718(2)
_cell_length_b                   27.8784(8)
_cell_length_c                   12.1169(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.641(2)
_cell_angle_gamma                90.00
_cell_volume                     2288.80(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4226
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      65.81

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1144
_exptl_absorpt_coefficient_mu    2.033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15152
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         67.23
_reflns_number_total             3866
_reflns_number_gt                3303
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX 2 (Bruker 2006)'
_computing_cell_refinement       'SAINT (Bruker 2006)'
_computing_data_reduction        'SAINT (Bruker 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 4.0.0 (Macrae et al, 2008)'
_computing_publication_material  'Bruker SHELXTL'
_chemical_absolute_configuration rm

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0715P)²+1.4223P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3866
_refine_ls_number_parameters     360
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1292
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1978(5) 0.64516(12) 0.7360(3) 0.0682(9) Uani 1 1 d . . .
H1 H 0.1189 0.6548 0.6641 0.082 Uiso 1 1 calc R . .
N1 N 0.2813(4) 0.67508(9) 0.8236(3) 0.0669(7) Uani 1 1 d . . .
H1N H 0.2701 0.7058 0.8213 0.080 Uiso 1 1 calc R . .
C2 C 0.3868(4) 0.64910(10) 0.9169(3) 0.0513(7) Uani 1 1 d . . .
C3 C 0.4916(5) 0.66312(14) 1.0284(3) 0.0681(9) Uani 1 1 d . . .
H3 H 0.5036 0.6953 1.0498 0.082 Uiso 1 1 calc R . .
C4 C 0.5756(5) 0.62772(17) 1.1050(3) 0.0764(11) Uani 1 1 d . . .
H4 H 0.6468 0.6360 1.1797 0.092 Uiso 1 1 calc R . .
C5 C 0.5567(6) 0.57973(15) 1.0734(3) 0.0739(10) Uani 1 1 d . . .
H5 H 0.6144 0.5565 1.1276 0.089 Uiso 1 1 calc R . .
C6 C 0.4556(5) 0.56589(11) 0.9648(3) 0.0610(8) Uani 1 1 d . . .
H6 H 0.4459 0.5336 0.9451 0.073 Uiso 1 1 calc R . .
C7 C 0.3671(4) 0.60031(9) 0.8837(2) 0.0467(6) Uani 1 1 d . . .
C8 C 0.2448(5) 0.59891(10) 0.7671(3) 0.0558(7) Uani 1 1 d . . .
C9 C 0.1811(5) 0.55532(11) 0.6943(3) 0.0660(9) Uani 1 1 d . . .
H9A H 0.0617 0.5627 0.6337 0.079 Uiso 1 1 calc R . .
H9B H 0.1498 0.5301 0.7414 0.079 Uiso 1 1 calc R . .
C10 C 0.3349(5) 0.53704(11) 0.6405(3) 0.0624(8) Uani 1 1 d . . .
H10 H 0.4566 0.5324 0.7033 0.075 Uiso 1 1 calc R . .
N2 N 0.3822(9) 0.57029(13) 0.5581(3) 0.143(2) Uani 1 1 d . . .
H2A H 0.2771 0.5737 0.4972 0.215 Uiso 1 1 calc R . .
H2B H 0.4822 0.5586 0.5356 0.215 Uiso 1 1 calc R . .
H2C H 0.4159 0.5987 0.5917 0.215 Uiso 1 1 calc R . .
C11 C 0.2855(5) 0.48905(11) 0.5791(3) 0.0578(8) Uani 1 1 d . . .
O1 O 0.2571(4) 0.45603(8) 0.6455(2) 0.0711(6) Uani 1 1 d . . .
H1O H 0.2111 0.4323 0.6072 0.107 Uiso 1 1 calc R . .
O2 O 0.2821(6) 0.48279(10) 0.4827(2) 0.1240(14) Uani 1 1 d . . .
C12 C -0.0017(3) 0.68527(9) 0.0426(2) 0.0372(5) Uani 1 1 d . . .
C13 C -0.0863(4) 0.65955(10) -0.0575(2) 0.0427(6) Uani 1 1 d . . .
H13 H -0.1518 0.6749 -0.1260 0.051 Uiso 1 1 calc R . .
C14 C -0.0689(4) 0.61045(9) -0.0512(2) 0.0432(6) Uani 1 1 d . . .
C15 C 0.0272(4) 0.58692(10) 0.0490(2) 0.0468(6) Uani 1 1 d . . .
H15 H 0.0391 0.5537 0.0510 0.056 Uiso 1 1 calc R . .
C16 C 0.1051(4) 0.61413(9) 0.1458(2) 0.0414(6) Uani 1 1 d . . .
C17 C 0.0902(3) 0.66402(8) 0.1482(2) 0.0365(5) Uani 1 1 d . . .
N3 N 0.2037(4) 0.58744(9) 0.2518(2) 0.0591(7) Uani 1 1 d . . .
O5 O 0.3684(4) 0.60000(10) 0.3059(2) 0.0792(7) Uani 1 1 d . . .
O6 O 0.1103(6) 0.55451(10) 0.2776(3) 0.1081(11) Uani 1 1 d . . .
N4 N -0.1649(4) 0.58177(10) -0.1538(2) 0.0570(6) Uani 1 1 d . . .
O8 O -0.2562(4) 0.60294(9) -0.24002(19) 0.0744(7) Uani 1 1 d . . .
O7 O -0.1492(4) 0.53833(9) -0.1458(2) 0.0830(8) Uani 1 1 d . . .
N5 N -0.0109(4) 0.73809(8) 0.03111(18) 0.0469(5) Uani 1 1 d . . .
O9 O -0.1703(3) 0.75613(8) -0.0111(2) 0.0676(6) Uani 1 1 d . . .
O10 O 0.1466(4) 0.75917(8) 0.0618(2) 0.0675(6) Uani 1 1 d . . .
S1 S 0.14083(9) 0.69680(2) 0.28284(5) 0.0419(2) Uani 1 1 d . . .
O11 O 0.0031(3) 0.73615(7) 0.25657(17) 0.0557(5) Uani 1 1 d . . .
O12 O 0.3435(3) 0.71193(8) 0.31407(16) 0.0568(5) Uani 1 1 d . . .
O13 O 0.0998(3) 0.66199(7) 0.36094(16) 0.0577(5) Uani 1 1 d . . .
O14 O -0.3815(5) 0.77067(10) 0.2168(2) 0.0711(7) Uani 1 1 d . . .
O15 O 0.1657(5) 0.37580(9) 0.5359(2) 0.0721(7) Uani 1 1 d . . .
O16 O 0.5303(4) 0.66122(8) 0.5456(2) 0.0620(6) Uani 1 1 d . . .
H14A H -0.285(7) 0.7564(15) 0.230(4) 0.083(14) Uiso 1 1 d . . .
H14B H -0.453(7) 0.7586(17) 0.244(4) 0.100(18) Uiso 1 1 d . . .
H15A H 0.097(6) 0.3592(16) 0.571(4) 0.090(13) Uiso 1 1 d . . .
H15B H 0.260(9) 0.365(2) 0.521(5) 0.13(2) Uiso 1 1 d . . .
H16A H 0.557(5) 0.6816(13) 0.601(3) 0.065(10) Uiso 1 1 d . . .
H16B H 0.478(6) 0.6771(15) 0.491(4) 0.083(13) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.346(5) . ?
C1 C8 1.357(4) . ?
C1 H1 0.9300 . ?
N1 C2 1.370(4) . ?
N1 H1N 0.8600 . ?
C2 C3 1.398(5) . ?
C2 C7 1.414(4) . ?
C3 C4 1.368(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.388(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.430(4) . ?
C8 C9 1.493(4) . ?
C9 C10 1.508(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.469(4) . ?
C10 C11 1.522(4) . ?
C10 H10 0.9800 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C11 O2 1.175(4) . ?
C11 O1 1.276(4) . ?
O1 H1O 0.8200 . ?
C12 C13 1.388(3) . ?
C12 C17 1.391(3) . ?
C12 N5 1.479(3) . ?
C13 C14 1.374(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(4) . ?
C14 N4 1.470(3) . ?
C15 C16 1.373(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.396(3) . ?
C16 N3 1.475(3) . ?
C17 S1 1.814(2) . ?
N3 O5 1.213(4) . ?
N3 O6 1.223(4) . ?
N4 O8 1.213(3) . ?
N4 O7 1.217(3) . ?
N5 O9 1.206(3) . ?
N5 O10 1.220(3) . ?
S1 O12 1.437(2) . ?
S1 O11 1.441(2) . ?
S1 O13 1.442(2) . ?
O14 H14A 0.77(5) . ?
O14 H14B 0.75(5) . ?
O15 H15A 0.87(5) . ?
O15 H15B 0.80(6) . ?
O16 H16A 0.86(4) . ?
O16 H16B 0.80(4) . ?

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
N1 C1 C8 110.6(3) . . ?
N1 C1 H1 124.7 . . ?
C8 C1 H1 124.7 . . ?
C1 N1 C2 109.6(2) . . ?
C1 N1 H1N 125.2 . . ?
C2 N1 H1N 125.2 . . ?
N1 C2 C3 131.5(3) . . ?
N1 C2 C7 106.7(3) . . ?
C3 C2 C7 121.7(3) . . ?
C4 C3 C2 117.4(3) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C2 118.4(3) . . ?
C6 C7 C8 134.7(3) . . ?
C2 C7 C8 106.8(2) . . ?
C1 C8 C7 106.2(3) . . ?
C1 C8 C9 126.9(3) . . ?
C7 C8 C9 126.9(3) . . ?
C8 C9 C10 113.4(3) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
N2 C10 C9 114.4(3) . . ?
N2 C10 C11 106.7(2) . . ?
C9 C10 C11 114.5(3) . . ?
N2 C10 H10 106.9 . . ?
C9 C10 H10 106.9 . . ?
C11 C10 H10 106.9 . . ?
C10 N2 H2A 109.5 . . ?
C10 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C10 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
O2 C11 O1 123.9(3) . . ?
O2 C11 C10 123.6(3) . . ?
O1 C11 C10 112.4(3) . . ?
C11 O1 H1O 109.5 . . ?
C13 C12 C17 123.7(2) . . ?
C13 C12 N5 115.8(2) . . ?
C17 C12 N5 120.5(2) . . ?
C14 C13 C12 117.2(2) . . ?
C14 C13 H13 121.4 . . ?
C12 C13 H13 121.4 . . ?
C13 C14 C15 122.5(2) . . ?
C13 C14 N4 118.8(2) . . ?
C15 C14 N4 118.6(2) . . ?
C16 C15 C14 117.8(2) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C15 C16 C17 123.6(2) . . ?
C15 C16 N3 116.1(2) . . ?
C17 C16 N3 120.3(2) . . ?
C12 C17 C16 115.1(2) . . ?
C12 C17 S1 122.19(18) . . ?
C16 C17 S1 121.60(18) . . ?
O5 N3 O6 125.7(3) . . ?
O5 N3 C16 117.8(3) . . ?
O6 N3 C16 116.5(3) . . ?
O8 N4 O7 124.5(3) . . ?
O8 N4 C14 117.8(3) . . ?
O7 N4 C14 117.7(3) . . ?
O9 N5 O10 126.1(2) . . ?
O9 N5 C12 117.8(2) . . ?
O10 N5 C12 116.1(2) . . ?
O12 S1 O11 113.25(13) . . ?
O12 S1 O13 113.43(13) . . ?
O11 S1 O13 114.04(13) . . ?
O12 S1 C17 108.04(11) . . ?
O11 S1 C17 103.78(11) . . ?
O13 S1 C17 103.08(11) . . ?
H14A O14 H14B 110(5) . . ?
H15A O15 H15B 122(5) . . ?
H16A O16 H16B 103(4) . . ?

_diffrn_measured_fraction_theta_max 0.938
_diffrn_reflns_theta_full        67.23
_diffrn_measured_fraction_theta_full 0.938
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.056
