Leveraging <i>in situ N</i>-tosylhydrazones as diazo surrogates for efficient access to pyrazolo-[1,5-<i>c</i>]quinazolinone derivatives.
Yan, Jun; Retailleau, Pascal; Tran, Christine; Hamze, Abdallah; Organic & biomolecular chemistry 22 (2024) 5816–5821; doi:10.1039/d4ob00950a

data_7160016
_publ_section_title
;
 Leveraging <i>in situ N</i>-tosylhydrazones as diazo surrogates for
 efficient access to pyrazolo-[1,5-<i>c</i>]quinazolinone derivatives.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5816
_journal_page_last               5821
_journal_paper_doi               10.1039/d4ob00950a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C18 H15 N3 O'
_chemical_formula_sum            'C18 H15 N3 O'
_chemical_formula_weight         289.339
_chemical_name_systematic
"'6-benzyl-2-methylpyrazolo[1,5-c]quinazolin-5(6H)-one'"
_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_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-17
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-03-19 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.020(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8567(6)
_cell_length_b                   9.2722(4)
_cell_length_c                   9.8086(4)
_cell_measurement_reflns_used    9458
_cell_measurement_temperature    293.0
_cell_measurement_theta_max      32.5260
_cell_measurement_theta_min      3.3470
_cell_volume                     1434.17(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement
'olex2.refine 1.5-ac5-024 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.0
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9984
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -20.00  99.00   0.50    6.00    --    9.20  57.00 -30.00  238
  2  \w    -20.00  99.00   0.50    6.00    --    9.20  57.00  60.00  238
  3  \w    -20.00  99.00   0.50    6.00    --    9.20  57.00 -90.00  238
  4  \w     23.00  99.00   0.50    6.00    --    9.20  57.00 -60.00  152
  5  \w      1.00  86.00   0.50    6.00    --    9.20  38.00 150.00  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0351014000
_diffrn_orient_matrix_UB_12      0.0444673000
_diffrn_orient_matrix_UB_13      0.0226875000
_diffrn_orient_matrix_UB_21      -0.0280287000
_diffrn_orient_matrix_UB_22      0.0576975000
_diffrn_orient_matrix_UB_23      0.0102486000
_diffrn_orient_matrix_UB_31      -0.0024129000
_diffrn_orient_matrix_UB_32      -0.0234466000
_diffrn_orient_matrix_UB_33      0.0682894000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.9988
_diffrn_reflns_Laue_measured_fraction_max 0.9984
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26314
_diffrn_reflns_point_group_measured_fraction_full 0.9988
_diffrn_reflns_point_group_measured_fraction_max 0.9984
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         3.03
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.639
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       tab
_exptl_crystal_F_000             608.0
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.1209
_refine_diff_density_min         -0.1337
_refine_diff_density_rms         0.0320
_refine_ls_d_res_high            0.7001
_refine_ls_d_res_low             6.7205
_refine_ls_extinction_coef       0.0187(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0994
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0242
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0077P)^2^+0.0293P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0441
_refine_ls_wR_factor_ref         0.0474
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              22
_reflns_limit_h_min              -22
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3366
_reflns_number_total             4365
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ob00950a2.cif
_cod_data_source_block           YJDP301
_cod_depositor_comments          'Adding full bibliography for 7160016.cif.'
_cod_database_code               7160016
_chemical_oxdiff_formula         C18H15N3O
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.318
_oxdiff_exptl_absorpt_empirical_full_min 0.752