Structure and cytotoxic properties of 1-hydroxy-5-methyl-7-phenylpyrido[3,4-<i>d</i>]pyridazin-4(3<i>H</i>)-one and its mono- and disubstituted ethyl acetates
Wójcicka, Anna; Becan, Lilianna; Rembiałkowska, Nina; Pyra, Anna; Bryndal, Iwona; Acta Crystallographica Section C 78 (2022) 559–569; doi:10.1107/S2053229622009202

data_2022672
_publ_section_title
;
 Structure and cytotoxic properties of
 1-hydroxy-5-methyl-7-phenylpyrido[3,4-<i>d</i>]pyridazin-4(3<i>H</i>)-one
 and its mono- and disubstituted ethyl acetates
;
_journal_coeditor_code           QF3056
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              559
_journal_page_last               569
_journal_paper_doi               10.1107/S2053229622009202
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C14 H11 N3 O2, C3 H7 N O'
_chemical_formula_moiety         'C14 H11 N3 O2, C3 H7 N O'
_chemical_formula_sum            'C17 H18 N4 O3'
_chemical_formula_weight         326.35
_chemical_name_systematic
;
1-Hydroxy-5-methyl-7-phenylpyrido[3,4-<i>d</i>]pyridazin-4(3<i>H</i>)-one
dimethylformamide monosolvate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                65.618(3)
_cell_angle_beta                 89.798(2)
_cell_angle_gamma                87.085(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8722(2)
_cell_length_b                   11.0502(3)
_cell_length_c                   11.2090(3)
_cell_measurement_reflns_used    7662
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.4
_cell_measurement_theta_min      4.3
_cell_volume                     774.14(4)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2014)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku XtaLAB Synergy DW system with a HyPix-Arc 150 detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10869
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.748
_diffrn_reflns_theta_min         4.331
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2020)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       needle
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.527
_refine_ls_extinction_coef       0.0035(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0680P)^2^+0.2445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1252
_reflns_number_gt                2827
_reflns_number_total             3149
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            qf3056sup1.cif
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_cod_depositor_comments
'Adding full bibliography for 2022672--2022674.cif.'
_cod_database_code               2022672
_cod_database_fobs_code          2022672
_shelx_estimated_absorpt_t_min   0.868
_shelx_estimated_absorpt_t_max   0.930
_shelx_hkl_checksum              91459
_shelx_res_checksum              34601