# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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 2227080'
loop_
_audit_author_name
_audit_author_address
'Anderson Berti Pagliari'
;Federal University Of Santa Maria
Brazil
;
_audit_update_record             
;
2022-12-16 deposited with the CCDC.	2023-08-16 downloaded from the CCDC.
;

_audit_creation_date             2022-12-16T15:00:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        N1,N2-bis(5-methylisoxazol-3-yl)oxalamide
_chemical_name_common            N1,N2-bis(5-methylisoxazol-3-yl)oxalamide
_chemical_formula_moiety         'C10 H10 N4 O4'
_chemical_formula_sum            'C10 H10 N4 O4'
_chemical_formula_weight         250.22
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   10.5137(4)
_cell_length_b                   5.4852(2)
_cell_length_c                   10.3155(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.873(2)
_cell_angle_gamma                90
_cell_volume                     555.85(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2486
_cell_measurement_theta_min      8.08
_cell_measurement_theta_max      67.9
_cell_measurement_wavelength     1.54178

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.146
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             260

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2016/2 - Bruker AXS area detector scaling and absorption
        correction. Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. &
        Stalke D., J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_correction_T_min  0.6724
_exptl_absorpt_correction_T_max  0.753
_exptl_transmission_factor_max   none
_exptl_transmission_factor_min   none
_shelx_estimated_absorpt_T_min   0.729
_shelx_estimated_absorpt_T_max   0.866

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_number            5630
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         8.685
_diffrn_reflns_theta_max         68.219
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.98
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.98
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.98
_reflns_Friedel_coverage         0
_reflns_number_total             1007
_reflns_number_gt                752
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-III'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_special_details          none
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0621P)²+0.0903P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1007
_refine_ls_number_parameters     83
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.18
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

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
O71 O 0.56925(13) 0.7555(2) 0.10097(13) 0.0601(4) Uani 1 1 d . . . . .
O1 O 0.81948(15) 0.2508(2) 0.49489(13) 0.0660(5) Uani 1 1 d . . . . .
C51 C 0.8999(2) 0.6147(4) 0.6296(2) 0.0652(6) Uani 1 1 d . . . . .
H51A H 0.890619 0.788557 0.619889 0.098 Uiso 1 1 calc R U . . .
H51C H 0.993702 0.570576 0.652476 0.098 Uiso 1 1 calc R U . . .
H51B H 0.869182 0.561597 0.702183 0.098 Uiso 1 1 calc R U . . .
C5 C 0.81665(18) 0.4965(3) 0.49722(17) 0.0495(5) Uani 1 1 d . . . . .
C4 C 0.73579(18) 0.5805(3) 0.37433(17) 0.0483(4) Uani 1 1 d . . . . .
H4 H 0.715913 0.742263 0.347787 0.058 Uiso 1 1 calc R U . . .
C3 C 0.68728(18) 0.3713(3) 0.29386(18) 0.0470(4) Uani 1 1 d . . . . .
N6 N 0.59818(15) 0.3509(3) 0.15690(16) 0.0522(4) Uani 1 1 d . . . . .
H6 H 0.57426 0.206918 0.124346 0.063 Uiso 1 1 calc R U . . .
C7 C 0.54713(16) 0.5416(3) 0.07223(17) 0.0479(4) Uani 1 1 d . . . . .
N2 N 0.73527(18) 0.1714(3) 0.36196(17) 0.0673(5) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O71 C7 1.212(2) . ?
O1 C5 1.348(2) . ?
O1 N2 1.410(2) . ?
C51 C5 1.483(2) . ?
C51 H51A 0.96 . ?
C51 H51C 0.96 . ?
C51 H51B 0.96 . ?
C5 C4 1.332(2) . ?
C4 C3 1.402(2) . ?
C4 H4 0.93 . ?
C3 N2 1.303(2) . ?
C3 N6 1.394(2) . ?
N6 C7 1.346(2) . ?
N6 H6 0.86 . ?
C7 C7 1.536(3) 3_665 ?

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
C5 O1 N2 108.42(12) . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51C C51 H51B 109.5 . . ?
C4 C5 O1 109.84(15) . . ?
C4 C5 C51 133.81(17) . . ?
O1 C5 C51 116.35(14) . . ?
C5 C4 C3 104.75(14) . . ?
C5 C4 H4 127.6 . . ?
C3 C4 H4 127.6 . . ?
N2 C3 N6 118.05(15) . . ?
N2 C3 C4 112.36(16) . . ?
N6 C3 C4 129.59(14) . . ?
C7 N6 C3 124.34(14) . . ?
C7 N6 H6 117.8 . . ?
C3 N6 H6 117.8 . . ?
O71 C7 N6 126.60(16) . . ?
O71 C7 C7 121.73(19) . 3_665 ?
N6 C7 C7 111.67(18) . 3_665 ?
C3 N2 O1 104.62(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
N2 O1 C5 C4 0.1(2) . . . . ?
N2 O1 C5 C51 -179.98(15) . . . . ?
O1 C5 C4 C3 0.1(2) . . . . ?
C51 C5 C4 C3 -179.8(2) . . . . ?
C5 C4 C3 N2 -0.3(2) . . . . ?
C5 C4 C3 N6 179.53(18) . . . . ?
N2 C3 N6 C7 -176.09(17) . . . . ?
C4 C3 N6 C7 4.1(3) . . . . ?
C3 N6 C7 O71 -0.4(3) . . . . ?
C3 N6 C7 C7 179.62(16) . . . 3_665 ?
N6 C3 N2 O1 -179.49(14) . . . . ?
C4 C3 N2 O1 0.3(2) . . . . ?
C5 O1 N2 C3 -0.3(2) . . . . ?


# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_Form1II
_database_code_depnum_ccdc_archive 'CCDC 2227100'
loop_
_audit_author_name
_audit_author_address
'Anderson Berti Pagliari'
;Federal University Of Santa Maria
Brazil
;
_audit_update_record             
;
2022-12-16 deposited with the CCDC.	2023-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        N1,N3-bis(5-methylisoxazol-3-yl)malonamide
_chemical_name_common            N1,N3-bis(5-methylisoxazol-3-yl)malonamide
_chemical_melting_point          none
_chemical_formula_moiety         'C11 H12 N4 O4'
_chemical_formula_sum            'C11 H12 N4 O4'
_chemical_formula_weight         264.25

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

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

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

_cell_length_a                   9.5647(2)
_cell_length_b                   4.69610(10)
_cell_length_c                   13.7344(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.1400(10)
_cell_angle_gamma                90
_cell_volume                     612.12(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4781
_cell_measurement_theta_min      4.66
_cell_measurement_theta_max      68.06

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   none
_exptl_transmission_factor_max   none
_exptl_crystal_size_max          0.518
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.109
_exptl_absorpt_coefficient_mu    0.949
_shelx_estimated_absorpt_T_min   0.639
_shelx_estimated_absorpt_T_max   0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6583
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption
correction. Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. &
Stalke D., J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_special_details   none
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            5935
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         9.349
_diffrn_reflns_theta_max         68.075
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.769
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.769
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.769
_reflns_number_total             1077
_reflns_number_gt                991
_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       'BRUKER APEX-III'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          none
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0704P)²+0.1192P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1077
_refine_ls_number_parameters     88
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1157
_refine_ls_wR_factor_gt          0.1120
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 -0.08206(16) 0.3155(4) 0.70688(10) 0.0931(6) Uani 1 1 d . . . . .
N6 N -0.05225(11) 0.1472(3) 0.86174(8) 0.0470(4) Uani 1 1 d . . . . .
H3 H -0.087481 0.036018 0.902101 0.056 Uiso 1 1 calc R U . . .
O1 O 0.24768(11) 0.4118(3) 1.00062(8) 0.0624(4) Uani 1 1 d . . . . .
C51 C 0.37470(19) 0.7683(4) 0.92331(16) 0.0722(5) Uani 1 1 d . . . . .
H2 H 0.392417 0.851991 0.987438 0.108 Uiso 1 1 calc R U . . .
H1 H 0.353234 0.915655 0.875320 0.108 Uiso 1 1 calc R U . . .
H7 H 0.456771 0.666042 0.909291 0.108 Uiso 1 1 calc R U . . .
C5 C 0.25359(15) 0.5694(3) 0.92005(12) 0.0535(4) Uani 1 1 d . . . . .
C4 C 0.14417(15) 0.5059(3) 0.85228(11) 0.0519(4) Uani 1 1 d . . . . .
H6 H 0.122558 0.584455 0.790073 0.062 Uiso 1 1 calc R U . . .
C3 C 0.06983(13) 0.2939(3) 0.89667(10) 0.0441(4) Uani 1 1 d . . . . .
C7 C -0.12007(14) 0.1645(3) 0.76990(10) 0.0496(4) Uani 1 1 d . . . . .
C9 C -0.250000 -0.0225(5) 0.750000 0.0527(5) Uani 1 2 d S T P . .
H4 H -0.242056 -0.143586 0.693723 0.063 Uiso 0.5 1 calc R U P . .
H5 H -0.257944 -0.143577 0.806279 0.063 Uiso 0.5 1 calc R U P . .
N2 N 0.12896(13) 0.2332(3) 0.98496(9) 0.0587(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
O8 C7 1.2095(19) . ?
N6 C7 1.3473(17) . ?
N6 C3 1.3890(17) . ?
N6 H3 0.8600 . ?
O1 C5 1.338(2) . ?
O1 N2 1.4066(16) . ?
C51 C5 1.485(2) . ?
C51 H2 0.9600 . ?
C51 H1 0.9600 . ?
C51 H7 0.9600 . ?
C5 C4 1.345(2) . ?
C4 C3 1.406(2) . ?
C4 H6 0.9300 . ?
C3 N2 1.3043(19) . ?
C7 C9 1.5185(18) . ?
C9 H4 0.9700 . ?
C9 H5 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N6 C3 125.43(12) . . ?
C7 N6 H3 117.3 . . ?
C3 N6 H3 117.3 . . ?
C5 O1 N2 108.64(11) . . ?
C5 C51 H2 109.5 . . ?
C5 C51 H1 109.5 . . ?
H2 C51 H1 109.5 . . ?
C5 C51 H7 109.5 . . ?
H2 C51 H7 109.5 . . ?
H1 C51 H7 109.5 . . ?
O1 C5 C4 109.91(13) . . ?
O1 C5 C51 115.85(15) . . ?
C4 C5 C51 134.24(16) . . ?
C5 C4 C3 104.41(13) . . ?
C5 C4 H6 127.8 . . ?
C3 C4 H6 127.8 . . ?
N2 C3 N6 117.47(13) . . ?
N2 C3 C4 111.95(12) . . ?
N6 C3 C4 130.57(12) . . ?
O8 C7 N6 123.56(13) . . ?
O8 C7 C9 121.51(12) . . ?
N6 C7 C9 114.94(11) . . ?
C7 C9 C7 109.33(17) 2_456 . ?
C7 C9 H4 109.8 2_456 . ?
C7 C9 H4 109.8 . . ?
C7 C9 H5 109.8 2_456 . ?
C7 C9 H5 109.8 . . ?
H4 C9 H5 108.3 . . ?
C3 N2 O1 105.09(12) . . ?

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
N2 O1 C5 C4 0.56(17) . . . . ?
N2 O1 C5 C51 -179.08(13) . . . . ?
O1 C5 C4 C3 -0.47(17) . . . . ?
C51 C5 C4 C3 179.07(17) . . . . ?
C7 N6 C3 N2 -173.93(14) . . . . ?
C7 N6 C3 C4 6.3(2) . . . . ?
C5 C4 C3 N2 0.22(18) . . . . ?
C5 C4 C3 N6 180.00(14) . . . . ?
C3 N6 C7 O8 -0.9(3) . . . . ?
C3 N6 C7 C9 178.93(13) . . . . ?
O8 C7 C9 C7 -65.87(15) . . . 2_456 ?
N6 C7 C9 C7 114.28(13) . . . 2_456 ?
N6 C3 N2 O1 -179.70(11) . . . . ?
C4 C3 N2 O1 0.11(17) . . . . ?
C5 O1 N2 C3 -0.40(17) . . . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.029


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Tetrahydrofuran'
####################################################################### 
# 
# 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_Form1III
_database_code_depnum_ccdc_archive 'CCDC 2227102'
loop_
_audit_author_name
_audit_author_address
'Anderson Berti Pagliari'
;Federal University Of Santa Maria
Brazil
;
_audit_update_record             
;
2022-12-16 deposited with the CCDC.	2023-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'N1,N3-bis (5-methylisoxazol-3-yl)malonamide'
_chemical_name_common            'malonamide-DMSO solvate'
_chemical_melting_point          none
_chemical_formula_moiety         'C11 H12 N4 O4, C2 H6 O S'
_chemical_formula_sum            'C13 H18 N4 O5 S'
_chemical_formula_weight         342.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      orthorhombic
_space_group_IT_number           31
_space_group_name_H-M_alt        'P m n 21'
_space_group_name_Hall           'P 2ac -2'

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

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

_cell_length_a                   20.0136(6)
_cell_length_b                   8.2017(3)
_cell_length_c                   9.8310(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1613.71(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9869
_cell_measurement_theta_min      5.39
_cell_measurement_theta_max      68.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   none
_exptl_transmission_factor_max   none
_exptl_crystal_size_min          0.166
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_max          0.282
_exptl_absorpt_coefficient_mu    2.073
_shelx_estimated_absorpt_T_min   0.593
_shelx_estimated_absorpt_T_max   0.725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6542
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption
correction. Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. &
Stalke D., J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_special_details   none
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            11581
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.393
_diffrn_reflns_theta_max         68.222
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_point_group_measured_fraction_full 0.897
_reflns_number_total             2717
_reflns_number_gt                2580
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_max     0.808
_reflns_Friedel_fraction_full    0.810

_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       'BRUKER APEX-III'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          none
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0717P)²+0.0878P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1046 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.121(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2717
_refine_ls_number_parameters     229
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
S11' S 0.500000 0.27852(11) 0.86449(12) 0.0542(3) Uani 1 2 d S T P . .
S11 S 0.500000 0.91030(11) 0.62969(10) 0.0437(3) Uani 1 2 d S T P . .
O8 O 0.58749(13) 0.7642(4) 0.0379(3) 0.0742(8) Uani 1 1 d . . . . .
O1' O 0.28223(12) 0.0562(3) 0.6741(3) 0.0624(6) Uani 1 1 d . . . . .
O8' O 0.41328(12) 0.2306(3) 0.2870(2) 0.0608(6) Uani 1 1 d . . . . .
O12' O 0.500000 0.3713(4) 0.7320(3) 0.0531(7) Uani 1 2 d S T P . .
O12 O 0.500000 0.8753(5) 0.4792(3) 0.0558(8) Uani 1 2 d S T P . .
N6 N 0.58645(13) 0.7699(3) 0.2680(3) 0.0474(6) Uani 1 1 d . . . . .
H6 H 0.566579 0.811013 0.337498 0.084(16) Uani 1 1 calc R . . . .
O1 O 0.70877(13) 0.5273(3) 0.4139(3) 0.0664(7) Uani 1 1 d . . . . .
N6' N 0.41294(12) 0.2604(3) 0.5171(3) 0.0460(6) Uani 1 1 d . . . . .
H6' H 0.434029 0.303769 0.584151 0.055 Uiso 1 1 calc R U . . .
N2' N 0.34010(15) 0.1556(4) 0.6752(3) 0.0604(7) Uani 1 1 d . . . . .
C51 C 0.78950(17) 0.4135(5) 0.2601(5) 0.0688(10) Uani 1 1 d . . . . .
H51A H 0.799726 0.412467 0.164743 0.103 Uiso 1 1 calc R U . . .
H51B H 0.826531 0.458480 0.309578 0.103 Uiso 1 1 calc R U . . .
H51C H 0.781274 0.304132 0.290634 0.103 Uiso 1 1 calc R U . . .
C5 C 0.72909(15) 0.5147(4) 0.2841(4) 0.0512(7) Uani 1 1 d . . . . .
C4 C 0.68789(15) 0.5994(4) 0.2033(4) 0.0529(8) Uani 1 1 d . . . . .
H4 H 0.689968 0.610465 0.109282 0.10(2) Uani 1 1 calc R . . . .
C3 C 0.64073(14) 0.6679(4) 0.2928(3) 0.0438(6) Uani 1 1 d . . . . .
C7 C 0.56231(15) 0.8097(3) 0.1440(3) 0.0457(6) Uani 1 1 d . . . . .
C9 C 0.500000 0.9152(5) 0.1450(5) 0.0512(10) Uani 1 2 d S T P . .
H9A H 0.500000 0.983494 0.225523 0.061 Uiso 1 2 calc R U P . .
H9B H 0.499999 0.985662 0.065783 0.061 Uiso 1 2 calc R U P . .
N2 N 0.65136(16) 0.6274(4) 0.4189(3) 0.0661(8) Uani 1 1 d . . . . .
C51' C 0.20738(19) -0.0876(5) 0.5247(4) 0.0685(10) Uani 1 1 d . . . . .
H51D H 0.187324 -0.111015 0.611214 0.103 Uiso 1 1 calc R U . . .
H51E H 0.175738 -0.031633 0.468085 0.103 Uiso 1 1 calc R U . . .
H51F H 0.220423 -0.187774 0.481650 0.103 Uiso 1 1 calc R U . . .
C5' C 0.26734(15) 0.0171(4) 0.5450(4) 0.0526(7) Uani 1 1 d . . . . .
C4' C 0.31244(16) 0.0834(4) 0.4604(3) 0.0510(7) Uani 1 1 d . . . . .
H4' H 0.314320 0.074869 0.366140 0.061 Uiso 1 1 calc R U . . .
C3' C 0.35651(14) 0.1692(4) 0.5475(3) 0.0437(6) Uani 1 1 d . . . . .
C7' C 0.43770(14) 0.2869(3) 0.3903(3) 0.0441(6) Uani 1 1 d . . . . .
C9' C 0.500000 0.3932(5) 0.3879(5) 0.0480(9) Uani 1 2 d S T P . .
H9'A H 0.500000 0.459891 0.306399 0.058 Uiso 1 2 calc R U P . .
H9'B H 0.500001 0.465195 0.466148 0.058 Uiso 1 2 calc R U P . .
C10' C 0.5667(2) 0.3576(7) 0.9598(4) 0.0809(12) Uani 1 1 d . . . . .
H10A H 0.569034 0.302410 1.045779 0.121 Uiso 1 1 calc R U . . .
H10B H 0.607720 0.341482 0.911008 0.121 Uiso 1 1 calc R U . . .
H10C H 0.559796 0.472003 0.974671 0.121 Uiso 1 1 calc R U . . .
C10 C 0.43314(18) 0.7952(5) 0.6983(4) 0.0612(9) Uani 1 1 d . . . . .
H10D H 0.430717 0.812826 0.794658 0.092 Uiso 1 1 calc R U . . .
H10E H 0.391971 0.828778 0.656710 0.092 Uiso 1 1 calc R U . . .
H10F H 0.440480 0.681449 0.680552 0.092 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
S11' O12' 1.508(3) . ?
S11' C10' 1.755(4) 3_655 ?
S11' C10' 1.755(4) . ?
S11 O12 1.507(3) . ?
S11 C10 1.771(3) . ?
S11 C10 1.771(3) 3_655 ?
O8 C7 1.217(4) . ?
O1' C5' 1.342(5) . ?
O1' N2' 1.417(4) . ?
O8' C7' 1.218(4) . ?
N6 C7 1.351(4) . ?
N6 C3 1.392(4) . ?
N6 H6 0.8600 . ?
O1 C5 1.343(4) . ?
O1 N2 1.413(4) . ?
N6' C7' 1.359(4) . ?
N6' C3' 1.387(4) . ?
N6' H6' 0.8600 . ?
N2' C3' 1.303(4) . ?
C51 C5 1.485(4) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C5 C4 1.339(5) . ?
C4 C3 1.407(4) . ?
C4 H4 0.9300 . ?
C3 N2 1.301(4) . ?
C7 C9 1.518(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C51' C5' 1.489(5) . ?
C51' H51D 0.9600 . ?
C51' H51E 0.9600 . ?
C51' H51F 0.9600 . ?
C5' C4' 1.342(5) . ?
C4' C3' 1.417(4) . ?
C4' H4' 0.9300 . ?
C7' C9' 1.522(4) . ?
C9' H9'A 0.9700 . ?
C9' H9'B 0.9700 . ?
C10' H10A 0.9600 . ?
C10' H10B 0.9600 . ?
C10' H10C 0.9600 . ?
C10 H10D 0.9600 . ?
C10 H10E 0.9600 . ?
C10 H10F 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
O12' S11' C10' 105.93(18) . 3_655 ?
O12' S11' C10' 105.93(18) . . ?
C10' S11' C10' 99.0(3) 3_655 . ?
O12 S11 C10 105.79(17) . . ?
O12 S11 C10 105.79(17) . 3_655 ?
C10 S11 C10 98.1(3) . 3_655 ?
C5' O1' N2' 109.0(2) . . ?
C7 N6 C3 125.6(3) . . ?
C7 N6 H6 117.2 . . ?
C3 N6 H6 117.2 . . ?
C5 O1 N2 108.9(3) . . ?
C7' N6' C3' 125.5(3) . . ?
C7' N6' H6' 117.2 . . ?
C3' N6' H6' 117.2 . . ?
C3' N2' O1' 104.4(3) . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
O1 C5 C4 109.7(3) . . ?
O1 C5 C51 116.1(3) . . ?
C4 C5 C51 134.2(4) . . ?
C5 C4 C3 104.5(3) . . ?
C5 C4 H4 127.8 . . ?
C3 C4 H4 127.8 . . ?
N2 C3 N6 116.6(3) . . ?
N2 C3 C4 112.6(3) . . ?
N6 C3 C4 130.8(3) . . ?
O8 C7 N6 123.4(3) . . ?
O8 C7 C9 121.4(3) . . ?
N6 C7 C9 115.2(3) . . ?
C7 C9 C7 110.5(3) 3_655 . ?
C7 C9 H9A 109.6 3_655 . ?
C7 C9 H9A 109.6 . . ?
C7 C9 H9B 109.6 3_655 . ?
C7 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C3 N2 O1 104.4(3) . . ?
C5' C51' H51D 109.5 . . ?
C5' C51' H51E 109.5 . . ?
H51D C51' H51E 109.5 . . ?
C5' C51' H51F 109.5 . . ?
H51D C51' H51F 109.5 . . ?
H51E C51' H51F 109.5 . . ?
C4' C5' O1' 109.9(3) . . ?
C4' C5' C51' 133.8(4) . . ?
O1' C5' C51' 116.3(3) . . ?
C5' C4' C3' 104.2(3) . . ?
C5' C4' H4' 127.9 . . ?
C3' C4' H4' 127.9 . . ?
N2' C3' N6' 117.3(3) . . ?
N2' C3' C4' 112.5(3) . . ?
N6' C3' C4' 130.2(3) . . ?
O8' C7' N6' 123.9(3) . . ?
O8' C7' C9' 122.2(3) . . ?
N6' C7' C9' 113.9(3) . . ?
C7' C9' C7' 110.0(3) 3_655 . ?
C7' C9' H9'A 109.7 3_655 . ?
C7' C9' H9'A 109.7 . . ?
C7' C9' H9'B 109.7 3_655 . ?
C7' C9' H9'B 109.7 . . ?
H9'A C9' H9'B 108.2 . . ?
S11' C10' H10A 109.5 . . ?
S11' C10' H10B 109.5 . . ?
H10A C10' H10B 109.5 . . ?
S11' C10' H10C 109.5 . . ?
H10A C10' H10C 109.5 . . ?
H10B C10' H10C 109.5 . . ?
S11 C10 H10D 109.5 . . ?
S11 C10 H10E 109.5 . . ?
H10D C10 H10E 109.5 . . ?
S11 C10 H10F 109.5 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 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
C5' O1' N2' C3' -0.4(4) . . . . ?
N2 O1 C5 C4 -0.7(4) . . . . ?
N2 O1 C5 C51 179.8(3) . . . . ?
O1 C5 C4 C3 0.8(4) . . . . ?
C51 C5 C4 C3 -179.8(4) . . . . ?
C7 N6 C3 N2 -171.5(3) . . . . ?
C7 N6 C3 C4 8.9(5) . . . . ?
C5 C4 C3 N2 -0.7(4) . . . . ?
C5 C4 C3 N6 178.9(3) . . . . ?
C3 N6 C7 O8 -2.7(5) . . . . ?
C3 N6 C7 C9 176.5(3) . . . . ?
O8 C7 C9 C7 88.4(5) . . . 3_655 ?
N6 C7 C9 C7 -90.9(4) . . . 3_655 ?
N6 C3 N2 O1 -179.3(3) . . . . ?
C4 C3 N2 O1 0.3(4) . . . . ?
C5 O1 N2 C3 0.2(4) . . . . ?
N2' O1' C5' C4' 0.7(4) . . . . ?
N2' O1' C5' C51' -179.9(3) . . . . ?
O1' C5' C4' C3' -0.7(4) . . . . ?
C51' C5' C4' C3' -180.0(4) . . . . ?
O1' N2' C3' N6' -179.3(2) . . . . ?
O1' N2' C3' C4' -0.1(4) . . . . ?
C7' N6' C3' N2' 179.6(3) . . . . ?
C7' N6' C3' C4' 0.5(5) . . . . ?
C5' C4' C3' N2' 0.5(4) . . . . ?
C5' C4' C3' N6' 179.6(3) . . . . ?
C3' N6' C7' O8' -1.1(4) . . . . ?
C3' N6' C7' C9' 179.4(2) . . . . ?
O8' C7' C9' C7' -85.9(4) . . . 3_655 ?
N6' C7' C9' C7' 93.6(4) . . . 3_655 ?

_refine_diff_density_max         0.682
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethyl sulfoxide'
####################################################################### 
# 
# 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_form1I
_database_code_depnum_ccdc_archive 'CCDC 2227101'
loop_
_audit_author_name
_audit_author_address
'Anderson Berti Pagliari'
;Federal University Of Santa Maria
Brazil
;
_audit_update_record             
;
2022-12-16 deposited with the CCDC.	2023-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        N1,N3-bis(5-methylisoxazol-3-yl)malonamide
_chemical_name_common            N1,N3-bis(5-methylisoxazol-3-yl)malonamide
_chemical_melting_point          none
_chemical_formula_moiety         'C11 H12 N4 O4'
_chemical_formula_sum            'C11 H12 N4 O4'
_chemical_formula_weight         264.25

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                   4.9247(2)
_cell_length_b                   9.8219(5)
_cell_length_c                   12.0712(6)
_cell_angle_alpha                88.350(2)
_cell_angle_beta                 82.4910(10)
_cell_angle_gamma                88.948(2)
_cell_volume                     578.57(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9958
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      27.15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   none
_exptl_transmission_factor_max   none
_exptl_crystal_size_min          0.202
_exptl_crystal_size_mid          0.317
_exptl_crystal_size_max          0.469
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6977
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption
correction. Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. &
Stalke D., J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_special_details   none
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            14771
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.649
_diffrn_reflns_theta_max         27.155
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2537
_reflns_number_gt                2400
_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       'BRUKER APEX-III'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          none
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0321P)²+0.4334P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2537
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.48591(18) 0.65864(9) 0.50484(7) 0.0143(2) Uani 1 1 d . . . . .
O1' O 0.69237(18) 1.07832(9) 0.29289(7) 0.0143(2) Uani 1 1 d . . . . .
O8 O 0.65198(19) 0.61362(9) 0.82911(8) 0.0172(2) Uani 1 1 d . . . . .
O1 O -0.07867(18) 0.28943(9) 0.81807(7) 0.0147(2) Uani 1 1 d . . . . .
N6 N 0.4474(2) 0.49953(11) 0.70148(9) 0.0131(2) Uani 1 1 d . . . . .
N6' N 0.7771(2) 0.83617(10) 0.50200(9) 0.0120(2) Uani 1 1 d . . . . .
N2 N 0.0726(2) 0.36046(11) 0.72778(9) 0.0136(2) Uani 1 1 d . . . . .
C51 C -0.1030(3) 0.24741(14) 1.01698(11) 0.0181(3) Uani 1 1 d . . . . .
H51C H -0.023234 0.280983 1.081062 0.027 Uiso 1 1 calc R U . . .
H51A H -0.073010 0.148701 1.012440 0.027 Uiso 1 1 calc R U . . .
H51B H -0.300099 0.267788 1.026239 0.027 Uiso 1 1 calc R U . . .
C5 C 0.0291(3) 0.31511(13) 0.91287(10) 0.0138(2) Uani 1 1 d . . . . .
C4 C 0.2437(2) 0.39939(12) 0.89029(10) 0.0136(2) Uani 1 1 d . . . . .
H4 H 0.356009 0.434225 0.940831 0.016 Uiso 1 1 calc R U . . .
C3 C 0.2617(2) 0.42362(12) 0.77320(10) 0.0116(2) Uani 1 1 d . . . . .
C7 C 0.6308(2) 0.58812(12) 0.73254(10) 0.0124(2) Uani 1 1 d . . . . .
C9 C 0.8173(2) 0.65214(13) 0.63528(10) 0.0142(3) Uani 1 1 d . . . . .
H9B H 0.925191 0.723741 0.664664 0.017 Uiso 1 1 calc R U . . .
H9A H 0.947970 0.581434 0.603239 0.017 Uiso 1 1 calc R U . . .
C7' C 0.6733(2) 0.71486(12) 0.54180(10) 0.0114(2) Uani 1 1 d . . . . .
C3' C 0.6935(2) 0.90971(12) 0.41214(10) 0.0110(2) Uani 1 1 d . . . . .
C4' C 0.4923(2) 0.88044(12) 0.34238(10) 0.0124(2) Uani 1 1 d . . . . .
H4' H 0.377110 0.803463 0.345913 0.015 Uiso 1 1 calc R U . . .
C5' C 0.5035(2) 0.98804(12) 0.26983(10) 0.0127(2) Uani 1 1 d . . . . .
C51' C 0.3582(3) 1.02417(13) 0.17264(11) 0.0171(3) Uani 1 1 d . . . . .
H51D H 0.473880 0.999909 0.103472 0.026 Uiso 1 1 calc R U . . .
H51F H 0.318543 1.122296 0.171370 0.026 Uiso 1 1 calc R U . . .
H51E H 0.186286 0.974164 0.178860 0.026 Uiso 1 1 calc R U . . .
N2' N 0.8136(2) 1.02636(11) 0.38523(9) 0.0138(2) Uani 1 1 d . . . . .
H6 H 0.446(4) 0.4880(18) 0.6306(16) 0.025(4) Uiso 1 1 d . . . . .
H6' H 0.904(4) 0.8734(18) 0.5352(15) 0.024(4) 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
O8' C7' 1.2233(15) . ?
O1' C5' 1.3568(14) . ?
O1' N2' 1.4103(13) . ?
O8 C7 1.2174(15) . ?
O1 C5 1.3546(15) . ?
O1 N2 1.4116(13) . ?
N6 C7 1.3600(16) . ?
N6 C3 1.3866(16) . ?
N6 H6 0.867(19) . ?
N6' C7' 1.3553(16) . ?
N6' C3' 1.3887(15) . ?
N6' H6' 0.877(19) . ?
N2 C3 1.3142(16) . ?
C51 C5 1.4828(17) . ?
C51 H51C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C5 C4 1.3492(17) . ?
C4 C3 1.4181(17) . ?
C4 H4 0.9500 . ?
C7 C9 1.5212(17) . ?
C9 C7' 1.5192(16) . ?
C9 H9B 0.9900 . ?
C9 H9A 0.9900 . ?
C3' N2' 1.3120(16) . ?
C3' C4' 1.4199(16) . ?
C4' C5' 1.3503(17) . ?
C4' H4' 0.9500 . ?
C5' C51' 1.4834(17) . ?
C51' H51D 0.9800 . ?
C51' H51F 0.9800 . ?
C51' H51E 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5' O1' N2' 108.13(9) . . ?
C5 O1 N2 108.75(9) . . ?
C7 N6 C3 125.91(11) . . ?
C7 N6 H6 117.8(12) . . ?
C3 N6 H6 116.2(12) . . ?
C7' N6' C3' 124.85(10) . . ?
C7' N6' H6' 119.0(12) . . ?
C3' N6' H6' 116.1(12) . . ?
C3 N2 O1 104.42(9) . . ?
C5 C51 H51C 109.5 . . ?
C5 C51 H51A 109.5 . . ?
H51C C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51C C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C4 C5 O1 110.33(11) . . ?
C4 C5 C51 133.27(12) . . ?
O1 C5 C51 116.39(11) . . ?
C5 C4 C3 103.55(11) . . ?
C5 C4 H4 128.2 . . ?
C3 C4 H4 128.2 . . ?
N2 C3 N6 116.72(11) . . ?
N2 C3 C4 112.94(11) . . ?
N6 C3 C4 130.32(11) . . ?
O8 C7 N6 124.16(11) . . ?
O8 C7 C9 121.72(11) . . ?
N6 C7 C9 114.11(11) . . ?
C7' C9 C7 115.52(10) . . ?
C7' C9 H9B 108.4 . . ?
C7 C9 H9B 108.4 . . ?
C7' C9 H9A 108.4 . . ?
C7 C9 H9A 108.4 . . ?
H9B C9 H9A 107.5 . . ?
O8' C7' N6' 123.70(11) . . ?
O8' C7' C9 122.62(11) . . ?
N6' C7' C9 113.66(10) . . ?
N2' C3' N6' 116.99(11) . . ?
N2' C3' C4' 112.53(11) . . ?
N6' C3' C4' 130.48(11) . . ?
C5' C4' C3' 103.52(11) . . ?
C5' C4' H4' 128.2 . . ?
C3' C4' H4' 128.2 . . ?
C4' C5' O1' 110.64(10) . . ?
C4' C5' C51' 133.47(11) . . ?
O1' C5' C51' 115.88(11) . . ?
C5' C51' H51D 109.5 . . ?
C5' C51' H51F 109.5 . . ?
H51D C51' H51F 109.5 . . ?
C5' C51' H51E 109.5 . . ?
H51D C51' H51E 109.5 . . ?
H51F C51' H51E 109.5 . . ?
C3' N2' O1' 105.18(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
C5 O1 N2 C3 0.30(12) . . . . ?
N2 O1 C5 C4 0.01(14) . . . . ?
N2 O1 C5 C51 -179.43(10) . . . . ?
O1 C5 C4 C3 -0.29(14) . . . . ?
C51 C5 C4 C3 179.02(13) . . . . ?
O1 N2 C3 N6 178.23(10) . . . . ?
O1 N2 C3 C4 -0.50(13) . . . . ?
C7 N6 C3 N2 169.45(11) . . . . ?
C7 N6 C3 C4 -12.1(2) . . . . ?
C5 C4 C3 N2 0.51(14) . . . . ?
C5 C4 C3 N6 -178.00(12) . . . . ?
C3 N6 C7 O8 -1.2(2) . . . . ?
C3 N6 C7 C9 177.39(11) . . . . ?
O8 C7 C9 C7' -130.86(12) . . . . ?
N6 C7 C9 C7' 50.54(15) . . . . ?
C3' N6' C7' O8' -2.66(19) . . . . ?
C3' N6' C7' C9 175.68(11) . . . . ?
C7 C9 C7' O8' -43.60(16) . . . . ?
C7 C9 C7' N6' 138.04(11) . . . . ?
C7' N6' C3' N2' 179.27(11) . . . . ?
C7' N6' C3' C4' -0.1(2) . . . . ?
N2' C3' C4' C5' 0.94(14) . . . . ?
N6' C3' C4' C5' -179.65(12) . . . . ?
C3' C4' C5' O1' -0.87(13) . . . . ?
C3' C4' C5' C51' 178.07(13) . . . . ?
N2' O1' C5' C4' 0.54(13) . . . . ?
N2' O1' C5' C51' -178.60(10) . . . . ?
N6' C3' N2' O1' 179.88(9) . . . . ?
C4' C3' N2' O1' -0.63(13) . . . . ?
C5' O1' N2' C3' 0.06(12) . . . . ?

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pyridine'
