Orthogonal Strapping of o-Haloaryl Ynones with Pyrazolones: A One-Pot, Domino Process toward Spiropyrazolones
Beesu, Mallesh; Mehta, Goverdhan; The Journal of Organic Chemistry  (2020) –; doi:10.1021/acs.joc.0c02087

data_4038886
_publ_section_title
;
 Orthogonal Strapping of o-Haloaryl Ynones with Pyrazolones: A One-Pot,
 Domino Process toward Spiropyrazolones
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c02087
_journal_year                    2020
_chemical_formula_moiety         'C24 H17 N3 O2'
_chemical_formula_sum            'C24 H17 N3 O2'
_chemical_formula_weight         379.40
_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   geom
_audit_creation_date             2019-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                95.554(4)
_cell_angle_beta                 95.804(4)
_cell_angle_gamma                96.061(4)
_cell_formula_units_Z            4
_cell_length_a                   7.9652(7)
_cell_length_b                   8.0725(8)
_cell_length_c                   30.441(3)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.41
_cell_measurement_theta_min      2.58
_cell_volume                     1925.0(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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      100.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1784
_diffrn_reflns_av_unetI/netI     0.0958
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            83127
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.562
_diffrn_reflns_theta_min         2.552
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1492 before and 0.0765 after correction. The Ratio of minimum to maximum transmission is 0.8598. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         8872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1772
_refine_ls_R_factor_gt           0.0851
_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^)+(0.0627P)^2^+1.9643P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1762
_refine_ls_wR_factor_ref         0.2081
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4615
_reflns_number_total             8872
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c02087_si_002.cif
_cod_data_source_block           gm129a_0m_a
_cod_depositor_comments
;

2025-07-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C24 H17 N3 O2)'
_cod_original_formula_sum        'C48 H34 N6 O4'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     758.81
_cod_database_code               4038886
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.981
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C1(H1), C42(H42), C38(H38), C11(H11), C2(H2), C36(H36), C12(H12),
 C34(H34), C44(H44), C43(H43), C3(H3), C15(H15), C13(H13), C14(H14), C33(H33),
 C32(H32), C19(H19), C29(H29), C31(H31), C23(H23), C20(H20), C21(H21), C22(H22),
  C27(H27), C28(H28), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C48(H48A,H48B,H48C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              82023
_shelx_hkl_checksum              91004
_olex2_submission_special_instructions 'No special instructions were received'