Two-pot sequential multicomponent metal-free synthesis of pyrrolo[2,3-d]pyridazin-7-ones and pyrrolo[2,3-d]pyrizidines
Mamta,; Mir, Nisar A.; Yadav, Jyothi; Pawar, Amol Prakash; Sharma, Ratika; Kant, Rajni; Rangan, Krishnan; Iype, Eldhose; Khungar, Bharti; Kumar, Indresh; New Journal of Chemistry 47 (2023) 14637–14645; doi:10.1039/D3NJ02249H

data_7062568
_publ_section_title
;
 Two-pot sequential multicomponent metal-free synthesis of
 pyrrolo[2,3-d]pyridazin-7-ones and pyrrolo[2,3-d]pyrizidines
;
_journal_issue                   31
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14637
_journal_page_last               14645
_journal_paper_doi               10.1039/D3NJ02249H
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C18 H13 N3'
_chemical_formula_sum            'C18 H13 N3'
_chemical_formula_weight         271.31
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-17
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-04-08 deposited with the CCDC.	2023-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.290(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.6435(6)
_cell_length_b                   9.6496(4)
_cell_length_c                   15.5396(4)
_cell_measurement_reflns_used    8366
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      79.4820
_cell_measurement_theta_min      5.0580
_cell_volume                     2644.99(16)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.945
_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    -45.00  -8.00   0.50    1.69    --    0.00 -37.00-120.00   74
  2  \w    -88.00  18.00   0.50    1.69    --    0.00 -37.00 120.00  212
  3  \w    -30.00  24.00   0.50    1.69    --    0.00 -77.00   0.00  108
  4  \w     22.00 136.00   0.50    6.76    --  107.20 -82.00 -60.00  228
  5  \w    106.00 197.00   0.50    6.76    --  107.20  30.00  90.00  182
  6  \w     96.00 195.00   0.50    6.76    --  107.20  30.00  60.00  198
  7  \w    148.00 175.00   0.50    6.76    --  107.20  15.00 150.00   54
  8  \w     88.00 133.00   0.50    6.76    --  107.20  15.00 150.00   90
  9  \w     19.00 132.00   0.50    6.76    --  107.20 -61.00   0.00  226
 10  \w     29.00 140.00   0.50    6.76    --  107.20 -82.00   0.00  222
 11  \w     22.00  87.00   0.50    6.76    --  107.20 -30.00 -30.00  130
 12  \w     87.00 112.00   0.50    6.76    --  107.20 -82.00-120.00   50
 13  \w     78.00 104.00   0.50    6.76    --  107.20 -77.00-120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0110163000
_diffrn_orient_matrix_UB_12      -0.1380352000
_diffrn_orient_matrix_UB_13      -0.0484773000
_diffrn_orient_matrix_UB_21      0.0031184000
_diffrn_orient_matrix_UB_22      -0.0788808000
_diffrn_orient_matrix_UB_23      0.0861777000
_diffrn_orient_matrix_UB_31      -0.0866088000
_diffrn_orient_matrix_UB_32      0.0148781000
_diffrn_orient_matrix_UB_33      0.0069736000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16652
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         82.950
_diffrn_reflns_theta_min         5.015
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0662P)^2^+0.7951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1343
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4666
_reflns_number_total             5587
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02249h2.cif
_cod_data_source_block           exp_1209_mk-206_20221017
_cod_depositor_comments
'Adding full bibliography for 7062567--7062568.cif.'
_cod_database_code               7062568
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H13 N3'
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.932
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23),
  C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33),
 C34(H34), C35(H35), C36(H36)
;
_shelx_res_checksum              71872
_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 1.834
_oxdiff_exptl_absorpt_empirical_full_min 0.689