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

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

data_1491
_database_code_depnum_ccdc_archive 'CCDC 1824217'
loop_
_audit_author_name
_audit_author_address
'Felipe Martins' 'UFG, IQ, Goi?nia GO'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.	2020-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' 2(C13 H10 Cl N5 O5), H2 O'
_chemical_formula_sum            'C26 H22 Cl2 N10 O11'
_chemical_formula_weight         721.43

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.666(5)
_cell_length_b                   8.002(5)
_cell_length_c                   33.179(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.513(5)
_cell_angle_gamma                90
_cell_volume                     3055(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    35580
_cell_measurement_theta_min      3.101
_cell_measurement_theta_max      25.240

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_type   none

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  KappaCCD
_diffrn_reflns_number            35580
_diffrn_reflns_av_unetI/netI     0.1080
_diffrn_reflns_av_R_equivalents  0.1930
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         3.101
_diffrn_reflns_theta_max         25.154
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             5317
_reflns_number_gt                2282
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0742P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5317
_refine_ls_number_parameters     468
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1698
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1689
_refine_ls_wR_factor_gt          0.1243
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      0.952
_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
C1A C 0.8828(5) -0.0423(7) 0.93203(15) 0.0795(14) Uani 1 1 d . . . . .
C2A C 0.9756(5) -0.1126(7) 0.92180(16) 0.0869(15) Uani 1 1 d . . . . .
H2A H 1.0303 -0.1773 0.9385 0.104 Uiso 1 1 calc R U . . .
C3A C 0.9760(4) -0.0710(6) 0.88102(14) 0.0752(13) Uani 1 1 d . . . . .
H3 H 1.0300 -0.1042 0.8649 0.090 Uiso 1 1 calc R U . . .
C4A C 0.8821(4) 0.0272(6) 0.86978(13) 0.0650(12) Uani 1 1 d . . . . .
C5A C 0.8344(4) 0.1164(5) 0.83356(13) 0.0645(12) Uani 1 1 d . . . . .
H5 H 0.7649 0.1748 0.8323 0.077 Uiso 1 1 calc R U . . .
C6A C 0.8961(4) 0.2227(6) 0.73787(14) 0.0641(12) Uani 1 1 d . . . . .
C7A C 0.9889(4) 0.0036(5) 0.67786(13) 0.0587(11) Uani 1 1 d . . . . .
C8A C 1.0368(3) -0.0124(5) 0.63947(12) 0.0558(11) Uani 1 1 d . . . . .
C9A C 0.9680(4) -0.0842(5) 0.60672(13) 0.0687(12) Uani 1 1 d . . . . .
H9A H 0.8940 -0.1211 0.6094 0.082 Uiso 1 1 calc R U . . .
C10A C 1.0059(4) -0.1029(6) 0.57006(13) 0.0782(14) Uani 1 1 d . . . . .
H10A H 0.9580 -0.1512 0.5480 0.094 Uiso 1 1 calc R U . . .
C11A C 1.1161(4) -0.0493(6) 0.56629(13) 0.0703(12) Uani 1 1 d . . . . .
C12A C 1.1853(4) 0.0211(6) 0.59874(14) 0.0717(13) Uani 1 1 d . . . . .
H12A H 1.2597 0.0563 0.5961 0.086 Uiso 1 1 calc R U . . .
C13A C 1.1475(3) 0.0410(5) 0.63538(13) 0.0641(11) Uani 1 1 d . . . . .
H13A H 1.1956 0.0899 0.6574 0.077 Uiso 1 1 calc R U . . .
N1A N 0.8379(6) -0.0396(8) 0.96955(16) 0.1083(18) Uani 1 1 d . . . . .
N2A N 0.8874(3) 0.1153(4) 0.80308(11) 0.0623(9) Uani 1 1 d . . . . .
N3A N 0.8388(3) 0.2085(5) 0.77020(11) 0.0682(11) Uani 1 1 d . . . . .
N4A N 0.9972(3) 0.1332(5) 0.74208(10) 0.0642(10) Uani 1 1 d . . . . .
N5A N 1.0429(3) 0.1079(5) 0.70673(10) 0.0646(10) Uani 1 1 d . . . . .
O1A O 0.8913(5) -0.1194(6) 0.99769(13) 0.1456(19) Uani 1 1 d . . . . .
O2A O 0.7485(5) 0.0409(7) 0.97030(14) 0.1359(18) Uani 1 1 d . . . . .
O3A O 0.8224(3) 0.0460(4) 0.90137(10) 0.0765(9) Uani 1 1 d . . . . .
O4A O 0.8609(3) 0.3124(4) 0.70920(9) 0.0852(10) Uani 1 1 d . . . . .
O5A O 0.9025(2) -0.0767(4) 0.68344(8) 0.0709(8) Uani 1 1 d . . . . .
Cl1A Cl 1.16486(14) -0.0727(2) 0.52077(4) 0.1123(6) Uani 1 1 d . . . . .
H3A H 0.777(5) 0.270(7) 0.7711(17) 0.135 Uiso 1 1 d . U . . .
H4A H 1.009(5) 0.052(7) 0.7613(17) 0.135 Uiso 1 1 d . U . . .
H5A H 1.095(5) 0.177(7) 0.7026(17) 0.135 Uiso 1 1 d . U . . .
C1B C 0.5489(4) 0.4007(6) 0.57348(14) 0.0700(12) Uani 1 1 d . . . . .
C2B C 0.6257(5) 0.4313(6) 0.54933(15) 0.0837(14) Uani 1 1 d . . . . .
H2B H 0.6218 0.3994 0.5222 0.100 Uiso 1 1 calc R U . . .
C3B C 0.7140(4) 0.5219(6) 0.57337(14) 0.0797(14) Uani 1 1 d . . . . .
H3' H 0.7807 0.5638 0.5651 0.096 Uiso 1 1 calc R U . . .
C4B C 0.6845(4) 0.5373(6) 0.61067(13) 0.0639(11) Uani 1 1 d . . . . .
C5B C 0.7379(4) 0.6178(5) 0.64728(13) 0.0616(11) Uani 1 1 d . . . . .
H5' H 0.8104 0.6679 0.6487 0.074 Uiso 1 1 calc R U . . .
C6B C 0.6857(4) 0.6986(5) 0.74560(13) 0.0572(11) Uani 1 1 d . . . . .
C7B C 0.5540(4) 0.4740(6) 0.79903(13) 0.0598(11) Uani 1 1 d . . . . .
C8B C 0.4947(3) 0.4698(5) 0.83474(12) 0.0575(11) Uani 1 1 d . . . . .
C9B C 0.5409(4) 0.3732(5) 0.86794(13) 0.0672(12) Uani 1 1 d . . . . .
H9B H 0.6057 0.3070 0.8665 0.081 Uiso 1 1 calc R U . . .
C10B C 0.4930(4) 0.3733(6) 0.90299(14) 0.0775(13) Uani 1 1 d . . . . .
H10B H 0.5266 0.3104 0.9254 0.093 Uiso 1 1 calc R U . . .
C11B C 0.3957(4) 0.4660(6) 0.90486(14) 0.0710(13) Uani 1 1 d . . . . .
C12B C 0.3461(4) 0.5578(6) 0.87216(14) 0.0704(12) Uani 1 1 d . . . . .
H12B H 0.2789 0.6184 0.8735 0.084 Uiso 1 1 calc R U . . .
C13B C 0.3946(4) 0.5619(6) 0.83707(13) 0.0658(12) Uani 1 1 d . . . . .
H13B H 0.3606 0.6261 0.8149 0.079 Uiso 1 1 calc R U . . .
N1B N 0.4418(4) 0.3102(5) 0.56728(15) 0.0845(12) Uani 1 1 d . . . . .
N2B N 0.6855(3) 0.6206(4) 0.67810(10) 0.0582(9) Uani 1 1 d . . . . .
N3B N 0.7385(3) 0.7011(5) 0.71221(10) 0.0609(10) Uani 1 1 d . . . . .
N4B N 0.5819(3) 0.6202(5) 0.73991(11) 0.0695(11) Uani 1 1 d . . . . .
N5B N 0.5252(3) 0.6010(5) 0.77299(11) 0.0650(10) Uani 1 1 d . . . . .
O1B O 0.4127(3) 0.2482(5) 0.53359(12) 0.1175(14) Uani 1 1 d . . . . .
O2B O 0.3867(3) 0.3021(5) 0.59579(11) 0.0976(11) Uani 1 1 d . . . . .
O3B O 0.5796(2) 0.4626(4) 0.61153(8) 0.0644(8) Uani 1 1 d . . . . .
O4B O 0.7309(2) 0.7649(4) 0.77773(9) 0.0647(8) Uani 1 1 d . . . . .
O5B O 0.6259(3) 0.3688(4) 0.79335(9) 0.0818(9) Uani 1 1 d . . . . .
Cl1B Cl 0.33761(13) 0.4670(2) 0.94913(4) 0.1049(5) Uani 1 1 d . . . . .
H3B H 0.796(5) 0.773(7) 0.7138(16) 0.126 Uiso 1 1 d . U . . .
H4B H 0.550(5) 0.578(7) 0.7156(17) 0.126 Uiso 1 1 d . U . . .
H5B H 0.485(5) 0.694(7) 0.7789(16) 0.126 Uiso 1 1 d . U . . .
O1W O 0.4337(4) 0.4327(5) 0.68167(14) 0.0868(11) Uani 1 1 d . . . . .
H1W H 0.377(5) 0.393(7) 0.6901(16) 0.11(2) Uiso 1 1 d . . . . .
H2W H 0.428(6) 0.408(8) 0.659(2) 0.15(3) 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
C1A C2A 1.314(7) . ?
C1A O3A 1.339(6) . ?
C1A N1A 1.428(7) . ?
C2A C3A 1.394(6) . ?
C3A C4A 1.350(6) . ?
C4A O3A 1.359(5) . ?
C4A C5A 1.429(6) . ?
C5A N2A 1.270(5) . ?
C6A O4A 1.208(5) . ?
C6A N3A 1.359(5) . ?
C6A N4A 1.367(5) . ?
C7A O5A 1.235(5) . ?
C7A N5A 1.346(5) . ?
C7A C8A 1.479(6) . ?
C8A C9A 1.367(5) . ?
C8A C13A 1.387(5) . ?
C9A C10A 1.369(6) . ?
C10A C11A 1.380(6) . ?
C11A C12A 1.357(6) . ?
C11A Cl1A 1.710(4) . ?
C12A C13A 1.370(6) . ?
N1A O1A 1.214(6) . ?
N1A O2A 1.230(6) . ?
N2A N3A 1.365(4) . ?
N4A N5A 1.381(4) . ?
C1B C2B 1.319(6) . ?
C1B O3B 1.348(5) . ?
C1B N1B 1.430(6) . ?
C2B C3B 1.397(6) . ?
C3B C4B 1.344(6) . ?
C4B O3B 1.367(5) . ?
C4B C5B 1.424(6) . ?
C5B N2B 1.275(5) . ?
C6B O4B 1.228(5) . ?
C6B N4B 1.350(5) . ?
C6B N3B 1.354(5) . ?
C7B O5B 1.225(5) . ?
C7B N5B 1.340(5) . ?
C7B C8B 1.468(6) . ?
C8B C9B 1.380(5) . ?
C8B C13B 1.394(6) . ?
C9B C10B 1.371(6) . ?
C10B C11B 1.365(6) . ?
C11B C12B 1.358(6) . ?
C11B Cl1B 1.717(5) . ?
C12B C13B 1.376(6) . ?
N1B O1B 1.219(5) . ?
N1B O2B 1.229(5) . ?
N2B N3B 1.359(4) . ?
N4B N5B 1.380(5) . ?

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
C2A C1A O3A 112.5(5) . . ?
C2A C1A N1A 131.9(6) . . ?
O3A C1A N1A 115.6(6) . . ?
C1A C2A C3A 106.5(5) . . ?
C4A C3A C2A 105.9(5) . . ?
C3A C4A O3A 110.3(4) . . ?
C3A C4A C5A 135.1(4) . . ?
O3A C4A C5A 114.6(4) . . ?
N2A C5A C4A 119.5(4) . . ?
O4A C6A N3A 121.6(5) . . ?
O4A C6A N4A 124.5(4) . . ?
N3A C6A N4A 113.8(4) . . ?
O5A C7A N5A 120.9(4) . . ?
O5A C7A C8A 121.2(4) . . ?
N5A C7A C8A 117.9(4) . . ?
C9A C8A C13A 119.1(4) . . ?
C9A C8A C7A 117.7(4) . . ?
C13A C8A C7A 123.2(4) . . ?
C8A C9A C10A 121.2(4) . . ?
C9A C10A C11A 119.3(4) . . ?
C12A C11A C10A 119.9(4) . . ?
C12A C11A Cl1A 120.3(4) . . ?
C10A C11A Cl1A 119.8(4) . . ?
C11A C12A C13A 121.0(4) . . ?
C12A C13A C8A 119.5(4) . . ?
O1A N1A O2A 126.0(6) . . ?
O1A N1A C1A 116.6(7) . . ?
O2A N1A C1A 117.4(6) . . ?
C5A N2A N3A 116.1(4) . . ?
C6A N3A N2A 118.9(4) . . ?
C6A N4A N5A 116.0(4) . . ?
C7A N5A N4A 119.6(3) . . ?
C1A O3A C4A 104.8(4) . . ?
C2B C1B O3B 113.5(4) . . ?
C2B C1B N1B 132.2(5) . . ?
O3B C1B N1B 114.3(4) . . ?
C1B C2B C3B 105.1(4) . . ?
C4B C3B C2B 107.3(4) . . ?
C3B C4B O3B 110.2(4) . . ?
C3B C4B C5B 133.2(4) . . ?
O3B C4B C5B 116.6(4) . . ?
N2B C5B C4B 119.5(4) . . ?
O4B C6B N4B 124.6(4) . . ?
O4B C6B N3B 121.1(4) . . ?
N4B C6B N3B 114.3(4) . . ?
O5B C7B N5B 121.8(4) . . ?
O5B C7B C8B 122.3(4) . . ?
N5B C7B C8B 115.9(4) . . ?
C9B C8B C13B 118.2(4) . . ?
C9B C8B C7B 118.9(4) . . ?
C13B C8B C7B 122.9(4) . . ?
C10B C9B C8B 121.1(4) . . ?
C11B C10B C9B 119.8(4) . . ?
C12B C11B C10B 120.3(4) . . ?
C12B C11B Cl1B 120.3(4) . . ?
C10B C11B Cl1B 119.4(4) . . ?
C11B C12B C13B 120.6(4) . . ?
C12B C13B C8B 120.0(4) . . ?
O1B N1B O2B 125.6(5) . . ?
O1B N1B C1B 116.3(5) . . ?
O2B N1B C1B 118.1(4) . . ?
C5B N2B N3B 117.6(3) . . ?
C6B N3B N2B 118.0(4) . . ?
C6B N4B N5B 118.5(4) . . ?
C7B N5B N4B 119.6(4) . . ?
C1B O3B C4B 104.0(3) . . ?

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-3

