Polymorphism in N-(5-methylisoxazol-3-yl)malonamide: understanding the supramolecular structure and the crystallization mechanism
Pagliari, Anderson B.; Rosa, Jéssica M. L.; de Lima, Priscila S. V.; Zimmer, Geórgia C.; da Silva, Maria E. C.; de Oliveira, Érica G.; Bonacorso, Helio G.; Zanatta, Nilo; Martins, Marcos A. P.; CrystEngComm 25 (2023) 5118–5132; doi:10.1039/D3CE00643C

data_7247218
_publ_section_title
;
 Polymorphism in N-(5-methylisoxazol-3-yl)malonamide: understanding the
 supramolecular structure and the crystallization mechanism
;
_journal_issue                   36
_journal_name_full               CrystEngComm
_journal_page_first              5118
_journal_page_last               5132
_journal_paper_doi               10.1039/D3CE00643C
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C11 H12 N4 O4, C2 H6 O S'
_chemical_formula_sum            'C13 H18 N4 O5 S'
_chemical_formula_weight         342.37
_chemical_melting_point          ?
_chemical_name_common            'malonamide-DMSO solvate'
_chemical_name_systematic        'N1,N3-bis (5-methylisoxazol-3-yl)malonamide'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_Hall           'P 2ac -2'
_space_group_name_H-M_alt        'P m n 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-12-16 deposited with the CCDC.	2023-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.0136(6)
_cell_length_b                   8.2017(3)
_cell_length_c                   9.8310(3)
_cell_measurement_reflns_used    9869
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      5.39
_cell_volume                     1613.71(9)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER APEX-III'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11581
_diffrn_reflns_point_group_measured_fraction_full 0.897
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.222
_diffrn_reflns_theta_min         5.393
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.073
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6542
_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_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dimethyl sulfoxide'
_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.166
_exptl_transmission_factor_max   none
_exptl_transmission_factor_min   none
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.039
_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)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2717
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0717P)^2^+0.0878P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0985
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.810
_reflns_Friedel_fraction_max     0.808
_reflns_number_gt                2580
_reflns_number_total             2717
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00643c2.cif
_cod_data_source_block           Form1III
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'none' was changed to '?'
-- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7247216--7247219.cif.
;
_cod_database_code               7247218
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.593
_shelx_estimated_absorpt_t_max   0.725
_exptl_absorpt_special_details   none
_shelx_res_checksum              27625