Co-crystallization of a neutral molecule and its zwitterionic tautomer: structure and Hirshfeld surface analysis of 5-methyl-4-(5-methyl-1<i>H</i>-pyrazol-3-yl)-2-phenyl-2,3-dihydro-1<i>H</i>-pyrazol-3-one 5-methyl-4-(5-methyl-1<i>H</i>-pyrazol-2-ium-3-yl)-3-oxo-2-phenyl-2,3-dihydro-1<i>H</i>-pyrazol-1-ide monohydrate
Asiri, Abdullah M.; Alzahrani, Khalid A. H.; Faidallah, Hassan M.; Alamry, Khalid A.; Jotani, Mukesh M.; Tiekink, Edward R. T.; Acta Crystallographica Section E 75 (2019) 565–570; doi:10.1107/S2056989019004389

data_2242893
_publ_section_title
;
 Co-crystallization of a neutral molecule and its zwitterionic tautomer:
 structure and Hirshfeld surface analysis of
 5-methyl-4-(5-methyl-1<i>H</i>-pyrazol-3-yl)-2-phenyl-2,3-dihydro-1<i>H</i>-pyrazol-3-one
 5-methyl-4-(5-methyl-1<i>H</i>-pyrazol-2-ium-3-yl)-3-oxo-2-phenyl-2,3-dihydro-1<i>H</i>-pyrazol-1-ide
 monohydrate
;
_journal_coeditor_code           HB7813
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              565
_journal_page_last               570
_journal_paper_doi               10.1107/S2056989019004389
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          '2C14 H14 N4 O, H2 O'
_chemical_formula_moiety         '2(C14 H14 N4 O), H2 O'
_chemical_formula_sum            'C28 H30 N8 O3'
_chemical_formula_weight         526.60
_chemical_name_systematic
;5-Methyl-4-(5-methyl-1<i>H</i>-pyrazol-3-yl)-2-phenyl-2,3-dihydro-1<i>H</i>-pyrazol-3-one
5-methyl-4-(5-methyl-1<i>H</i>-pyrazol-2-ium-3-yl)-3-oxo-2-phenyl-2,3-dihydro-1<i>H</i>-pyrazol-1-ide monohydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 98.379(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7007(6)
_cell_length_b                   7.0419(3)
_cell_length_c                   31.2567(17)
_cell_measurement_reflns_used    3750
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5013
_cell_measurement_theta_min      2.3418
_cell_volume                     2547.9(2)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2011)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2011)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2011)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), <i>QMol</i>Gans & Shalloway
(2001)
and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            10823
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_min         2.347
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9953
_exptl_absorpt_correction_T_min  0.9680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2011)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.405
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5838
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0593P)^2^+0.7451P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1371
_reflns_number_gt                4411
_reflns_number_total             5838
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7813sup1.cif
_cod_data_source_block           I
_cod_database_code               2242893
_cod_database_fobs_code          2242893
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.995
_shelx_hkl_checksum              51642
_shelx_res_checksum              19096