An unprecedented N- to C-sulfonyl migration in the reaction of azomethine amine and allenoates: Access to arylsulfonylmethyl substituted pyrazolo[1,5-c]quinazoline and mechanistic studies
Ansari, Arshad J.; Wani, Aabid; Maurya, Antim Kumar; Verma, Sarika; Agnihotri, Vijai K.; Sharon, Ashoke; Bharatam, Prasad V.; Sawant, Devesh M.; Chemical Communications  (2019) –; doi:10.1039/C9CC06751E

data_7124499
_publ_section_title
;
 An unprecedented N- to C-sulfonyl migration in the reaction of azomethine
 amine and allenoates: Access to arylsulfonylmethyl substituted
 pyrazolo[1,5-c]quinazoline and mechanistic studies
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06751E
_journal_year                    2019
_chemical_formula_moiety         'C24 H25 Cl N4 O4 S'
_chemical_formula_sum            'C24 H25 Cl N4 O4 S'
_chemical_formula_weight         500.99
_chemical_name_common            quinazoline
_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   mixed
_audit_creation_date             2019-02-24
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_audit_update_record
;
2019-02-24 deposited with the CCDC.	2019-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.463(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.4467(13)
_cell_length_b                   18.9064(9)
_cell_length_c                   11.4637(5)
_cell_measurement_reflns_used    7605
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5100
_cell_measurement_theta_min      3.7200
_cell_volume                     4823.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25959
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.419
_diffrn_reflns_theta_min         3.360
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             2096
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     629
_refine_ls_number_reflns         11318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0769
_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^)+(0.1314P)^2^+4.9520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2421
_refine_ls_wR_factor_ref         0.2696
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7311
_reflns_number_total             11318
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06751e2.cif
_cod_data_source_block           dmspt001
_cod_database_code               7124499
_shelx_shelxl_version_number     2018/3
_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
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B), C46(H46A,H46B), C48(H48A,H48B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C20(H20), C21(H21), C23(H23), C24(H24),
 C31(H31), C32(H32), C33(H33), C34(H34), C50(H50), C51(H51), C53(H53), C54(H54)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C17(H17A,H17B,
 H17C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C47(H47A,
 H47B,H47C)
;
_shelx_res_checksum              77570
_olex2_submission_special_instructions 'No special instructions were received'