# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1997487'
loop_
_audit_author_name
_audit_author_address
'EFREN GARCIA'
;Laboratory of supramolecular chemistry and nanosciences, IPN
Mexico
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 N4 O8'
_chemical_formula_weight         398.37

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

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

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

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

_cell_length_a                   7.0616(4)
_cell_length_b                   12.9600(6)
_cell_length_c                   10.6639(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.752(4)
_cell_angle_gamma                90
_cell_volume                     972.59(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25

_exptl_crystal_description       bock
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
Interpolation using  Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3
for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959)
p.302; Table 5.3.6 B for muR in the range 2.6-10.0.
The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975)
A31,146-148) is used with some modification.
;
_exptl_absorpt_correction_T_min  0.8614
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_ave  0.8614
_exptl_absorpt_coefficient_mu    0.110
_exptl_crystal_size_rad          0.1500

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Xcalibur Ruby Gemini'
_diffrn_measurement_method       ω
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_reflns_number            34245
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.144
_diffrn_reflns_theta_max         29.761
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2682
_reflns_number_gt                2022
_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       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury 4.0 (Macrae et al., 2020)'
_computing_publication_material  
'WINGX-2018.3 (Farrugia, 2012)/Platon (Spek, 2003)'

_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)+(0.0514P)²+0.2316P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2682
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
O8 O 0.11113(16) 0.77307(7) 0.67766(8) 0.0521(3) Uani 1 1 d . . . . .
O9 O 0.2108(2) 0.88820(8) 0.39700(9) 0.0743(4) Uani 1 1 d . . . . .
O10 O 0.20211(16) 0.96014(7) 0.58567(8) 0.0509(3) Uani 1 1 d . . . . .
H10 H 0.234(3) 1.0181(17) 0.539(2) 0.089(6) Uiso 1 1 d . . . . .
N7 N 0.09793(15) 0.70835(8) 0.47728(9) 0.0386(3) Uani 1 1 d . . . . .
H7 H 0.112(2) 0.7276(12) 0.4049(15) 0.046 Uiso 1 1 d . U . . .
C1 C 0.04903(16) 0.60358(9) 0.49248(10) 0.0343(3) Uani 1 1 d . . . . .
C2 C 0.02129(19) 0.54379(9) 0.38444(10) 0.0406(3) Uani 1 1 d . . . . .
H2 H 0.036328 0.573417 0.306457 0.049 Uiso 1 1 calc R U . . .
C3 C 0.02825(19) 0.55890(9) 0.60885(10) 0.0407(3) Uani 1 1 d . . . . .
H3 H 0.047617 0.597997 0.681919 0.049 Uiso 1 1 calc R U . . .
C8 C 0.12487(17) 0.78214(9) 0.56541(10) 0.0376(3) Uani 1 1 d . . . . .
C9 C 0.18311(19) 0.88420(9) 0.50647(11) 0.0414(3) Uani 1 1 d . . . . .
O11 O 0.70908(17) 0.87390(8) 0.52937(10) 0.0610(3) Uani 1 1 d . . . . .
N12 N 0.60758(18) 0.81968(12) 0.71476(13) 0.0625(4) Uani 1 1 d . . . . .
C11 C 0.6541(2) 0.89035(12) 0.63412(15) 0.0563(4) Uani 1 1 d . . . . .
H11 H 0.644538 0.958929 0.658485 0.068 Uiso 1 1 calc R U . . .
C13 C 0.5447(3) 0.8489(2) 0.83544(19) 0.0969(7) Uani 1 1 d . . . . .
H13A H 0.635062 0.825083 0.901348 0.145 Uiso 1 1 calc R U . . .
H13B H 0.423062 0.818265 0.845336 0.145 Uiso 1 1 calc R U . . .
H13C H 0.534340 0.922612 0.839750 0.145 Uiso 1 1 calc R U . . .
C14 C 0.6187(3) 0.71071(15) 0.6884(2) 0.0916(7) Uani 1 1 d . . . . .
H14A H 0.695165 0.677297 0.755115 0.137 Uiso 1 1 calc R U . . .
H14B H 0.675015 0.700748 0.610406 0.137 Uiso 1 1 calc R U . . .
H14C H 0.493244 0.681597 0.682168 0.137 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
O8 C8 1.2146(14) . ?
O9 C9 1.2006(15) . ?
O10 C9 1.2967(14) . ?
O10 H10 0.94(2) . ?
N7 C8 1.3433(14) . ?
N7 C1 1.4137(15) . ?
N7 H7 0.825(16) . ?
C1 C3 1.3881(15) . ?
C1 C2 1.3888(16) . ?
C2 C3 1.3795(17) 3_566 ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C8 C9 1.5351(17) . ?
O11 C11 1.2313(19) . ?
N12 C11 1.316(2) . ?
N12 C14 1.443(3) . ?
N12 C13 1.446(2) . ?
C11 H11 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O10 H10 106.4(13) . . ?
C8 N7 C1 128.71(10) . . ?
C8 N7 H7 114.7(11) . . ?
C1 N7 H7 116.6(11) . . ?
C3 C1 C2 119.39(11) . . ?
C3 C1 N7 123.24(10) . . ?
C2 C1 N7 117.37(10) . . ?
C3 C2 C1 120.95(10) 3_566 . ?
C3 C2 H2 119.5 3_566 . ?
C1 C2 H2 119.5 . . ?
C2 C3 C1 119.66(10) 3_566 . ?
C2 C3 H3 120.2 3_566 . ?
C1 C3 H3 120.2 . . ?
O8 C8 N7 127.04(11) . . ?
O8 C8 C9 122.20(10) . . ?
N7 C8 C9 110.74(10) . . ?
O9 C9 O10 125.74(12) . . ?
O9 C9 C8 120.41(11) . . ?
O10 C9 C8 113.83(10) . . ?
C11 N12 C14 122.21(16) . . ?
C11 N12 C13 120.73(17) . . ?
C14 N12 C13 117.05(17) . . ?
O11 C11 N12 125.92(16) . . ?
O11 C11 H11 117.0 . . ?
N12 C11 H11 117.0 . . ?
N12 C13 H13A 109.5 . . ?
N12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N12 C14 H14A 109.5 . . ?
N12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N7 C1 C3 -2.8(2) . . . . ?
C8 N7 C1 C2 177.26(12) . . . . ?
C3 C1 C2 C3 0.6(2) . . . 3_566 ?
N7 C1 C2 C3 -179.47(12) . . . 3_566 ?
C2 C1 C3 C2 -0.6(2) . . . 3_566 ?
N7 C1 C3 C2 179.48(12) . . . 3_566 ?
C1 N7 C8 O8 -0.4(2) . . . . ?
C1 N7 C8 C9 178.03(11) . . . . ?
O8 C8 C9 O9 173.72(14) . . . . ?
N7 C8 C9 O9 -4.84(19) . . . . ?
O8 C8 C9 O10 -4.72(19) . . . . ?
N7 C8 C9 O10 176.72(11) . . . . ?
C14 N12 C11 O11 0.8(3) . . . . ?
C13 N12 C11 O11 180.00(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O10 H10 O11 0.94(2) 1.65(2) 2.5792(14) 175(2) 3_676 yes
N7 H7 O8 0.825(16) 2.423(16) 3.2132(13) 160.8(14) 4_575 yes
N7 H7 O9 0.825(16) 2.199(15) 2.6295(14) 112.6(12) . yes
C2 H2 O8 0.93 2.50 3.3362(15) 149.9 4_575 yes
C3 H3 O8 0.93 2.31 2.9179(15) 122.2 . yes
C3 H3 O9 0.93 2.49 3.3042(16) 146.8 4_576 yes
C11 H11 O9 0.93 2.33 3.0511(18) 134.3 3_676 yes

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.034



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1874282'
loop_
_audit_author_name
_audit_author_address
'EFREN GARCIA'
;Laboratory of supramolecular chemistry and nanosciences, IPN
Mexico
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 N2 O8 S2'
_chemical_formula_weight         408.44

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'

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

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

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

_cell_length_a                   7.6501(2)
_cell_length_b                   11.8612(4)
_cell_length_c                   10.4802(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.090(3)
_cell_angle_gamma                90
_cell_volume                     941.50(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.300
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
Interpolation using  Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3
for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959)
p.302; Table 5.3.6 B for muR in the range 2.6-10.0.
The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975)
A31,146-148) is used with some modification.
;
_exptl_absorpt_correction_T_min  0.5559
_exptl_absorpt_correction_T_max  0.5863
_exptl_absorpt_correction_T_ave  0.5712
_exptl_absorpt_coefficient_mu    2.972
_exptl_crystal_size_rad          0.1500
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Xcalibur Ruby Gemini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        5
_diffrn_reflns_number            9168
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.665
_diffrn_reflns_theta_max         73.615
_diffrn_reflns_theta_full        67.680
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1881
_reflns_number_gt                1584
_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       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury 4.0 (Macrae et al., 2020)'
_computing_publication_material  
'WINGX-2018.3 (Farrugia, 2012)/Platon (Spek, 2003)'

_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)+(0.0601P)²+0.3951P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1881
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1157
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0662(2) 0.39047(15) 0.51468(17) 0.0316(4) Uani 1 1 d . . . . .
C2 C -0.0044(3) 0.44330(16) 0.61384(18) 0.0380(4) Uani 1 1 d . . . . .
H2 H -0.007127 0.405072 0.691020 0.046 Uiso 1 1 calc R U . . .
C3 C 0.0709(3) 0.44841(17) 0.39976(18) 0.0386(5) Uani 1 1 d . . . . .
H3 H 0.118559 0.414420 0.332477 0.046 Uiso 1 1 calc R U . . .
C8 C 0.1759(2) 0.20662(15) 0.44806(18) 0.0317(4) Uani 1 1 d . . . . .
C9 C 0.2245(3) 0.08974(16) 0.50740(19) 0.0389(5) Uani 1 1 d . . . . .
C10 C 0.5616(4) 0.1505(2) 0.2331(2) 0.0556(6) Uani 1 1 d . . . . .
H10A H 0.575370 0.186272 0.152963 0.083 Uiso 1 1 calc R U . . .
H10B H 0.440569 0.155750 0.247243 0.083 Uiso 1 1 calc R U . . .
H10C H 0.594708 0.072557 0.229893 0.083 Uiso 1 1 calc R U . . .
C11 C 0.6060(4) 0.3564(2) 0.3425(3) 0.0626(7) Uani 1 1 d . . . . .
H11A H 0.626106 0.387016 0.261002 0.094 Uiso 1 1 calc R U . . .
H11B H 0.660723 0.404006 0.410777 0.094 Uiso 1 1 calc R U . . .
H11C H 0.481398 0.352470 0.345686 0.094 Uiso 1 1 calc R U . . .
N7 N 0.1303(2) 0.27901(13) 0.53601(16) 0.0356(4) Uani 1 1 d . . . . .
H7 H 0.128(3) 0.2540(19) 0.603(2) 0.038(6) Uiso 1 1 d . . . . .
O1 O 0.6404(3) 0.17540(13) 0.48468(16) 0.0629(5) Uani 1 1 d . . . . .
O8 O 0.1792(2) 0.22603(11) 0.33485(13) 0.0405(4) Uani 1 1 d . . . . .
O9 O 0.2281(3) 0.07219(14) 0.61985(16) 0.0736(6) Uani 1 1 d . . . . .
O10 O 0.2600(3) 0.01733(13) 0.42173(15) 0.0533(4) Uani 1 1 d . . . . .
H10 H 0.276(4) -0.048(3) 0.459(3) 0.075(9) Uiso 1 1 d . . . . .
S1 S 0.69868(8) 0.21857(5) 0.36107(6) 0.0510(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.387(3) . ?
C1 C3 1.392(3) . ?
C1 N7 1.417(2) . ?
C2 C3 1.382(3) 3_566 ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C8 O8 1.212(2) . ?
C8 N7 1.341(2) . ?
C8 C9 1.543(3) . ?
C9 O9 1.193(2) . ?
C9 O10 1.299(2) . ?
C10 S1 1.776(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 S1 1.782(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N7 H7 0.77(2) . ?
O1 S1 1.5171(18) . ?
O10 H10 0.87(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C3 119.06(17) . . ?
C2 C1 N7 117.78(17) . . ?
C3 C1 N7 123.16(17) . . ?
C3 C2 C1 121.30(18) 3_566 . ?
C3 C2 H2 119.3 3_566 . ?
C1 C2 H2 119.3 . . ?
C2 C3 C1 119.64(17) 3_566 . ?
C2 C3 H3 120.2 3_566 . ?
C1 C3 H3 120.2 . . ?
O8 C8 N7 126.45(17) . . ?
O8 C8 C9 121.86(16) . . ?
N7 C8 C9 111.68(16) . . ?
O9 C9 O10 126.12(19) . . ?
O9 C9 C8 121.70(17) . . ?
O10 C9 C8 112.18(17) . . ?
S1 C10 H10A 109.5 . . ?
S1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
S1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 N7 C1 127.35(17) . . ?
C8 N7 H7 115.2(18) . . ?
C1 N7 H7 117.0(18) . . ?
C9 O10 H10 108(2) . . ?
O1 S1 C10 106.14(12) . . ?
O1 S1 C11 104.06(11) . . ?
C10 S1 C11 98.70(13) . . ?

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
C3 C1 C2 C3 0.4(4) . . . 3_566 ?
N7 C1 C2 C3 -179.47(19) . . . 3_566 ?
C2 C1 C3 C2 -0.4(3) . . . 3_566 ?
N7 C1 C3 C2 179.47(19) . . . 3_566 ?
O8 C8 C9 O9 176.9(2) . . . . ?
N7 C8 C9 O9 -3.7(3) . . . . ?
O8 C8 C9 O10 -2.7(3) . . . . ?
N7 C8 C9 O10 176.67(18) . . . . ?
O8 C8 N7 C1 4.2(3) . . . . ?
C9 C8 N7 C1 -175.16(18) . . . . ?
C2 C1 N7 C8 168.0(2) . . . . ?
C3 C1 N7 C8 -11.9(3) . . . . ?

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.053



####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1997485'
loop_
_audit_author_name
_audit_author_address
'EFREN GARCIA'
;Laboratory of supramolecular chemistry and nanosciences, IPN
Mexico
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H40 N6 O24'
_chemical_formula_weight         892.70

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5470(8)
_cell_length_b                   10.2921(9)
_cell_length_c                   11.4084(11)
_cell_angle_alpha                70.436(9)
_cell_angle_beta                 66.208(9)
_cell_angle_gamma                86.296(7)
_cell_volume                     963.26(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_F_000             466
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200


_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
Interpolation using  Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3
for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959)
p.302; Table 5.3.6 B for muR in the range 2.6-10.0.
The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975)
A31,146-148) is used with some modification.
;
_exptl_absorpt_correction_T_min  0.8614
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_ave  0.8615
_exptl_absorpt_coefficient_mu    0.134
_exptl_crystal_size_rad          0.1500

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Xcalibur Ruby Gemini'
_diffrn_measurement_method       ω
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_reflns_number            29987
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.018
_diffrn_reflns_theta_max         29.807
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5069
_reflns_number_gt                2474
_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       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury 4.0 (Macrae et al., 2020)'
_computing_publication_material  
'WINGX-2018.3 (Farrugia, 2012)/Platon (Spek, 2003)'
_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)+(0.0970P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5069
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1456
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1948
_refine_ls_wR_factor_gt          0.1528
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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
O8 O 0.55220(19) 1.31733(17) 0.1047(2) 0.0434(5) Uani 1 1 d . . . . .
O9 O 0.86057(18) 1.13866(18) 0.1473(2) 0.0435(5) Uani 1 1 d . . . . .
O10 O 0.80400(19) 1.35461(17) 0.1397(2) 0.0438(5) Uani 1 1 d . . . . .
H10 H 0.884138 1.356542 0.157923 0.066 Uiso 1 1 d R U . . .
O18 O 0.08492(19) 0.65888(18) 0.1798(2) 0.0457(5) Uani 1 1 d . . . . .
O20 O -0.1679(2) 0.6340(2) 0.1460(2) 0.0559(6) Uani 1 1 d . . . . .
H20 H -0.242288 0.637206 0.126652 0.084 Uiso 1 1 calc R U . . .
O19 O -0.2308(2) 0.8406(2) 0.1640(2) 0.0583(6) Uani 1 1 d . . . . .
N7 N 0.5759(2) 1.0844(2) 0.1676(2) 0.0325(5) Uani 1 1 d . . . . .
H7 H 0.637977 1.023842 0.184203 0.039 Uiso 1 1 calc R U . . .
N17 N 0.0363(2) 0.8781(2) 0.1826(2) 0.0328(5) Uani 1 1 d . . . . .
H17 H -0.034088 0.934937 0.185321 0.039 Uiso 1 1 calc R U . . .
C1 C 0.4362(2) 1.0334(2) 0.1758(2) 0.0297(5) Uani 1 1 d . . . . .
C2 C 0.4305(3) 0.9029(3) 0.1676(3) 0.0348(6) Uani 1 1 d . . . . .
H2 H 0.515722 0.851544 0.158927 0.042 Uiso 1 1 calc R U . . .
C3 C 0.2993(3) 0.8482(2) 0.1721(3) 0.0344(6) Uani 1 1 d . . . . .
H3 H 0.295827 0.760141 0.167262 0.041 Uiso 1 1 calc R U . . .
C4 C 0.1726(2) 0.9252(2) 0.1840(2) 0.0300(5) Uani 1 1 d . . . . .
C5 C 0.1765(3) 1.0531(2) 0.1976(3) 0.0334(6) Uani 1 1 d . . . . .
H5 H 0.090376 1.103462 0.208577 0.040 Uiso 1 1 calc R U . . .
C6 C 0.3065(3) 1.1071(3) 0.1952(3) 0.0329(6) Uani 1 1 d . . . . .
H6 H 0.307285 1.192428 0.206522 0.039 Uiso 1 1 calc R U . . .
C8 C 0.6213(3) 1.2157(2) 0.1369(3) 0.0307(5) Uani 1 1 d . . . . .
C9 C 0.7776(3) 1.2323(2) 0.1425(3) 0.0321(6) Uani 1 1 d . . . . .
C18 C 0.0052(3) 0.7566(3) 0.1774(3) 0.0339(6) Uani 1 1 d . . . . .
C19 C -0.1474(3) 0.7491(3) 0.1631(3) 0.0365(6) Uani 1 1 d . . . . .
O28 O 0.7310(2) 0.33301(18) 0.4653(2) 0.0482(5) Uani 1 1 d . . . . .
O29 O 1.05165(19) 0.15678(19) 0.4779(2) 0.0443(5) Uani 1 1 d . . . . .
O30 O 0.9893(2) 0.36730(19) 0.4877(2) 0.0502(5) Uani 1 1 d . . . . .
H30 H 1.074237 0.373548 0.488110 0.075 Uiso 1 1 calc R U . . .
N27 N 0.7747(2) 0.1088(2) 0.4810(2) 0.0326(5) Uani 1 1 d . . . . .
H27 H 0.844724 0.051736 0.479928 0.039 Uiso 1 1 calc R U . . .
C21 C 0.6346(2) 0.0577(2) 0.4891(2) 0.0303(5) Uani 1 1 d . . . . .
C22 C 0.6289(3) -0.0726(3) 0.4801(3) 0.0359(6) Uani 1 1 d . . . . .
H22 H 0.715902 -0.121794 0.466479 0.043 Uiso 1 1 d R U . . .
C23 C 0.5046(3) 0.1308(3) 0.5086(3) 0.0374(6) Uani 1 1 d . . . . .
H23 H 0.505782 0.218115 0.515756 0.045 Uiso 1 1 d R U . . .
C28 C 0.8093(3) 0.2348(2) 0.4748(3) 0.0325(6) Uani 1 1 d . . . . .
C29 C 0.9666(3) 0.2481(3) 0.4795(3) 0.0334(6) Uani 1 1 d . . . . .
O3 O 0.2420(2) 0.41664(19) 0.5010(2) 0.0510(5) Uani 1 1 d . . . . .
H3A H 0.229924 0.481508 0.529701 0.077 Uiso 1 1 calc R U . . .
C31 C 0.3625(4) 0.4553(4) 0.3683(4) 0.0855(12) Uani 1 1 d . . . . .
H31A H 0.456796 0.474959 0.372817 0.128 Uiso 1 1 calc R U . . .
H31B H 0.338380 0.536128 0.309544 0.128 Uiso 1 1 calc R U . . .
H31C H 0.373679 0.380786 0.333115 0.128 Uiso 1 1 calc R U . . .
O1 O 0.04772(19) 0.39503(19) 0.1695(2) 0.0450(5) Uani 1 1 d . . . . .
H1B H 0.123435 0.404063 0.102835 0.067 Uiso 1 1 d R U . . .
H1A H 0.056709 0.482710 0.171285 0.067 Uiso 1 1 d R U . . .
O2 O 0.6408(2) 0.59288(19) 0.0462(2) 0.0558(6) Uani 1 1 d . . . . .
H2A H 0.584932 0.635617 -0.005722 0.084 Uiso 1 1 d R U . . .
H2B H 0.615952 0.511130 0.070737 0.084 Uiso 1 1 d 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
O8 C8 1.230(3) . ?
O9 C9 1.208(3) . ?
O10 C9 1.287(3) . ?
O10 H10 0.8729 . ?
O18 C18 1.221(3) . ?
O20 C19 1.302(3) . ?
O20 H20 0.8200 . ?
O19 C19 1.194(3) . ?
N7 C8 1.331(3) . ?
N7 C1 1.422(3) . ?
N7 H7 0.8600 . ?
N17 C18 1.328(3) . ?
N17 C4 1.426(3) . ?
N17 H17 0.8600 . ?
C1 C2 1.384(3) . ?
C1 C6 1.388(3) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C5 C6 1.379(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.542(3) . ?
C18 C19 1.540(3) . ?
O28 C28 1.219(3) . ?
O29 C29 1.201(3) . ?
O30 C29 1.300(3) . ?
O30 H30 0.8200 . ?
N27 C28 1.332(3) . ?
N27 C21 1.425(3) . ?
N27 H27 0.8600 . ?
C21 C22 1.385(3) . ?
C21 C23 1.388(3) . ?
C22 C23 1.383(3) 2_656 ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C28 C29 1.540(3) . ?
O3 C31 1.422(4) . ?
O3 H3A 0.8200 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
O1 H1B 0.7922 . ?
O1 H1A 0.9196 . ?
O2 H2A 0.9375 . ?
O2 H2B 0.8106 . ?

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 O10 H10 109.4 . . ?
C19 O20 H20 109.5 . . ?
C8 N7 C1 127.14(19) . . ?
C8 N7 H7 116.4 . . ?
C1 N7 H7 116.4 . . ?
C18 N17 C4 127.65(19) . . ?
C18 N17 H17 116.2 . . ?
C4 N17 H17 116.2 . . ?
C2 C1 C6 119.6(2) . . ?
C2 C1 N7 117.52(19) . . ?
C6 C1 N7 122.8(2) . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 N17 117.7(2) . . ?
C3 C4 N17 122.7(2) . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
O8 C8 N7 126.2(2) . . ?
O8 C8 C9 120.8(2) . . ?
N7 C8 C9 112.93(19) . . ?
O9 C9 O10 127.1(2) . . ?
O9 C9 C8 121.5(2) . . ?
O10 C9 C8 111.45(19) . . ?
O18 C18 N17 127.0(2) . . ?
O18 C18 C19 120.5(2) . . ?
N17 C18 C19 112.5(2) . . ?
O19 C19 O20 126.1(2) . . ?
O19 C19 C18 122.8(2) . . ?
O20 C19 C18 111.1(2) . . ?
C29 O30 H30 109.5 . . ?
C28 N27 C21 127.35(19) . . ?
C28 N27 H27 116.3 . . ?
C21 N27 H27 116.3 . . ?
C22 C21 C23 119.2(2) . . ?
C22 C21 N27 117.7(2) . . ?
C23 C21 N27 123.1(2) . . ?
C23 C22 C21 120.9(2) 2_656 . ?
C23 C22 H22 119.5 2_656 . ?
C21 C22 H22 119.5 . . ?
C22 C23 C21 119.8(2) 2_656 . ?
C22 C23 H23 119.6 2_656 . ?
C21 C23 H23 120.6 . . ?
O28 C28 N27 126.5(2) . . ?
O28 C28 C29 121.1(2) . . ?
N27 C28 C29 112.4(2) . . ?
O29 C29 O30 126.8(2) . . ?
O29 C29 C28 122.6(2) . . ?
O30 C29 C28 110.6(2) . . ?
C31 O3 H3A 109.5 . . ?
O3 C31 H31A 109.5 . . ?
O3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
H1B O1 H1A 96.0 . . ?
H2A O2 H2B 103.9 . . ?

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 N7 C1 C2 160.6(2) . . . . ?
C8 N7 C1 C6 -21.2(4) . . . . ?
C6 C1 C2 C3 3.1(4) . . . . ?
N7 C1 C2 C3 -178.7(2) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 -3.0(4) . . . . ?
C2 C3 C4 N17 176.8(2) . . . . ?
C18 N17 C4 C5 -176.3(2) . . . . ?
C18 N17 C4 C3 3.8(4) . . . . ?
C3 C4 C5 C6 2.1(4) . . . . ?
N17 C4 C5 C6 -177.8(2) . . . . ?
C4 C5 C6 C1 1.5(4) . . . . ?
C2 C1 C6 C5 -4.0(4) . . . . ?
N7 C1 C6 C5 177.8(2) . . . . ?
C1 N7 C8 O8 -3.2(4) . . . . ?
C1 N7 C8 C9 178.0(2) . . . . ?
O8 C8 C9 O9 -165.2(2) . . . . ?
N7 C8 C9 O9 13.7(4) . . . . ?
O8 C8 C9 O10 14.1(3) . . . . ?
N7 C8 C9 O10 -167.0(2) . . . . ?
C4 N17 C18 O18 4.0(5) . . . . ?
C4 N17 C18 C19 -174.3(2) . . . . ?
O18 C18 C19 O19 177.9(3) . . . . ?
N17 C18 C19 O19 -3.7(4) . . . . ?
O18 C18 C19 O20 -4.1(4) . . . . ?
N17 C18 C19 O20 174.2(2) . . . . ?
C28 N27 C21 C22 173.3(2) . . . . ?
C28 N27 C21 C23 -8.2(4) . . . . ?
C23 C21 C22 C23 -0.5(4) . . . 2_656 ?
N27 C21 C22 C23 178.0(2) . . . 2_656 ?
C22 C21 C23 C22 0.5(4) . . . 2_656 ?
N27 C21 C23 C22 -177.9(2) . . . 2_656 ?
C21 N27 C28 O28 -5.6(4) . . . . ?
C21 N27 C28 C29 175.0(2) . . . . ?
O28 C28 C29 O29 -173.9(3) . . . . ?
N27 C28 C29 O29 5.4(4) . . . . ?
O28 C28 C29 O30 7.3(4) . . . . ?
N27 C28 C29 O30 -173.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O10 H10 O1 0.87 1.70 2.561(2) 167.9 1_665 yes
O20 H20 O2 0.82 1.86 2.629(2) 155.0 1_455 yes
N7 H7 O19 0.86 2.22 3.018(3) 154.3 1_655 yes
N17 H17 O9 0.86 2.25 3.068(2) 158.6 1_455 yes
C2 H2 O19 0.93 2.44 3.241(3) 144.6 1_655 yes
C3 H3 O18 0.93 2.26 2.872(3) 122.9 . yes
C5 H5 O9 0.93 2.53 3.304(3) 140.9 1_455 yes
C6 H6 O8 0.93 2.38 2.908(3) 115.8 . yes
O30 H30 O3 0.82 1.76 2.571(2) 167.9 1_655 yes
N27 H27 O29 0.86 2.30 2.706(2) 109.0 . yes
N27 H27 O29 0.86 2.29 3.102(3) 158.0 2_756 yes
C22 H22 O29 0.93 2.52 3.293(3) 141.1 2_756 yes
C23 H23 O28 0.93 2.29 2.877(3) 120.9 . yes
O3 H3A O28 0.82 1.99 2.772(2) 158.6 2_666 yes
O3 H3A O30 0.82 2.56 3.027(2) 117.6 2_666 yes
O1 H1B O2 0.79 2.20 2.975(3) 165.9 2_665 yes
O1 H1A O18 0.92 1.89 2.808(2) 176.2 . yes
O1 H1A O20 0.92 2.62 3.116(2) 114.4 . yes
O2 H2A O8 0.94 1.99 2.913(2) 167.0 2_675 yes
O2 H2B O8 0.81 1.99 2.791(2) 171.5 1_545 yes
O2 H2B O10 0.81 2.52 2.945(2) 114.0 1_545 yes

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.064



####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1997486'
loop_
_audit_author_name
_audit_author_address
'EFREN GARCIA'
;Laboratory of supramolecular chemistry and nanosciences, IPN
Mexico
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H22 N4 O6'
_chemical_formula_weight         342.35

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   5.9712(3)
_cell_length_b                   7.0040(3)
_cell_length_c                   20.4618(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.336(4)
_cell_angle_gamma                90
_cell_volume                     846.72(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            pinkless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.350

_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
Interpolation using  Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3
for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959)
p.302; Table 5.3.6 B for muR in the range 2.6-10.0.
The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975)
A31,146-148) is used with some modification.
;
_exptl_absorpt_correction_T_min  0.8614
_exptl_absorpt_correction_T_max  0.8645
_exptl_absorpt_correction_T_ave  0.8632
_exptl_absorpt_coefficient_mu    0.106
_exptl_crystal_size_rad          0.1500

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Xcalibur Ruby Gemini'
_diffrn_measurement_method       ω
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_reflns_number            29486
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.078
_diffrn_reflns_theta_max         29.670
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2340
_reflns_number_gt                2016
_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       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury 4.0 (Macrae et al., 2020)'
_computing_publication_material  
'WINGX-2018.3 (Farrugia, 2012)/Platon (Spek, 2003)'

_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)+(0.0447P)²+0.1955P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.044(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2340
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.1001
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.84456(16) 0.63776(14) 0.47569(4) 0.0288(2) Uani 1 1 d . . . . .
C2 C 1.06194(18) 0.69026(15) 0.50191(5) 0.0342(2) Uani 1 1 d . . . . .
H2 H 1.103815 0.818241 0.503065 0.041 Uiso 1 1 calc R U . . .
C3 C 0.78223(18) 0.44815(15) 0.47348(5) 0.0342(2) Uani 1 1 d . . . . .
H3 H 0.635978 0.413094 0.455528 0.041 Uiso 1 1 calc R U . . .
C8 C 0.59715(16) 0.80341(14) 0.38897(4) 0.0284(2) Uani 1 1 d . . . . .
C9 C 0.42420(17) 0.96856(14) 0.37587(5) 0.0308(2) Uani 1 1 d . . . . .
C11 C 0.1522(2) 0.45429(19) 0.33644(6) 0.0472(3) Uani 1 1 d . . . . .
H11A H 0.292473 0.493774 0.322942 0.071 Uiso 1 1 calc R U . . .
H11B H 0.178445 0.415745 0.381933 0.071 Uiso 1 1 calc R U . . .
H11C H 0.046964 0.558720 0.331277 0.071 Uiso 1 1 calc R U . . .
C12 C -0.1604(2) 0.2268(2) 0.31152(7) 0.0553(3) Uani 1 1 d . . . . .
H12A H -0.217009 0.125933 0.281870 0.083 Uiso 1 1 calc R U . . .
H12B H -0.266044 0.330875 0.307148 0.083 Uiso 1 1 calc R U . . .
H12C H -0.141063 0.180184 0.356105 0.083 Uiso 1 1 calc R U . . .
N1 N 0.05824(15) 0.29292(13) 0.29535(4) 0.0330(2) Uani 1 1 d . . . . .
H1A H 0.047(2) 0.3276(19) 0.2532(7) 0.040(3) Uiso 1 1 d . . . . .
H1AB H 0.163(2) 0.191(2) 0.3018(7) 0.047(4) Uiso 1 1 d . . . . .
N7 N 0.68358(15) 0.78181(13) 0.45244(4) 0.0328(2) Uani 1 1 d . . . . .
H7 H 0.638(2) 0.857(2) 0.4809(7) 0.053(4) Uiso 1 1 d . . . . .
O8 O 0.64755(15) 0.70631(12) 0.34380(4) 0.0437(2) Uani 1 1 d . . . . .
O9 O 0.37897(17) 1.06098(14) 0.42323(4) 0.0535(3) Uani 1 1 d . . . . .
O10 O 0.34769(15) 0.99280(12) 0.31638(4) 0.0448(2) 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 C3 1.3781(15) . ?
C1 C2 1.3806(14) . ?
C1 N7 1.4268(12) . ?
C2 C3 1.3868(14) 3_766 ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C8 O8 1.2198(12) . ?
C8 N7 1.3347(12) . ?
C8 C9 1.5480(13) . ?
C9 O9 1.2277(12) . ?
C9 O10 1.2481(12) . ?
C11 N1 1.4704(15) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 N1 1.4674(15) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 H1A 0.889(14) . ?
N1 H1AB 0.947(15) . ?
N7 H7 0.859(16) . ?

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
C3 C1 C2 120.24(9) . . ?
C3 C1 N7 120.32(9) . . ?
C2 C1 N7 119.43(9) . . ?
C1 C2 C3 119.90(10) . 3_766 ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 3_766 . ?
C1 C3 C2 119.86(10) . 3_766 ?
C1 C3 H3 120.1 . . ?
C2 C3 H3 120.1 3_766 . ?
O8 C8 N7 124.82(9) . . ?
O8 C8 C9 121.13(8) . . ?
N7 C8 C9 114.04(8) . . ?
O9 C9 O10 127.36(9) . . ?
O9 C9 C8 118.35(8) . . ?
O10 C9 C8 114.28(8) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C12 N1 C11 113.08(10) . . ?
C12 N1 H1A 110.9(8) . . ?
C11 N1 H1A 108.3(9) . . ?
C12 N1 H1AB 108.9(9) . . ?
C11 N1 H1AB 108.0(9) . . ?
H1A N1 H1AB 107.4(12) . . ?
C8 N7 C1 123.47(8) . . ?
C8 N7 H7 118.2(10) . . ?
C1 N7 H7 118.3(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 C3 -0.43(17) . . . 3_766 ?
N7 C1 C2 C3 178.02(9) . . . 3_766 ?
C2 C1 C3 C2 0.43(17) . . . 3_766 ?
N7 C1 C3 C2 -178.00(9) . . . 3_766 ?
O8 C8 C9 O9 179.64(11) . . . . ?
N7 C8 C9 O9 -1.21(15) . . . . ?
O8 C8 C9 O10 -1.08(15) . . . . ?
N7 C8 C9 O10 178.07(10) . . . . ?
O8 C8 N7 C1 -1.34(17) . . . . ?
C9 C8 N7 C1 179.54(9) . . . . ?
C3 C1 N7 C8 -68.36(14) . . . . ?
C2 C1 N7 C8 113.19(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C11 H11A O8 0.96 2.58 3.4290(16) 148.3 . yes
C11 H11C O8 0.96 2.65 3.5142(15) 150.7 1_455 yes
N1 H1A O8 0.889(14) 2.310(14) 2.9952(11) 133.8(11) 2_545 yes
N1 H1A O10 0.889(14) 2.006(14) 2.8062(12) 149.0(12) 2_545 yes
N1 H1AB O10 0.947(15) 1.770(15) 2.7158(11) 176.4(13) 1_545 yes
N7 H7 O9 0.859(16) 2.061(16) 2.8460(12) 151.7(14) 3_676 yes

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.036



