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_7247216
_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         'C10 H10 N4 O4'
_chemical_formula_sum            'C10 H10 N4 O4'
_chemical_formula_weight         250.22
_chemical_melting_point          ?
_chemical_name_common            N1,N2-bis(5-methylisoxazol-3-yl)oxalamide
_chemical_name_systematic        N1,N2-bis(5-methylisoxazol-3-yl)oxalamide
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2022-12-16T15:00:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2022-12-16 deposited with the CCDC.	2023-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.873(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5137(4)
_cell_length_b                   5.4852(2)
_cell_length_c                   10.3155(4)
_cell_measurement_reflns_used    2486
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      67.9
_cell_measurement_theta_min      8.08
_cell_measurement_wavelength     1.54178
_cell_volume                     555.85(4)
_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      296(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.98
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5630
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.98
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.219
_diffrn_reflns_theta_min         8.685
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.012
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.6724
_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    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             260
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.146
_exptl_transmission_factor_max   none
_exptl_transmission_factor_min   none
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.18
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1007
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+0.0903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1134
_reflns_Friedel_coverage         0
_reflns_number_gt                752
_reflns_number_total             1007
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00643c2.cif
_cod_data_source_block           shelx
_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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7247216
_shelx_estimated_absorpt_t_min   0.729
_shelx_estimated_absorpt_t_max   0.866
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              56080