Diastereoselective synthesis of indolenine-based spiro[pyrazolone-4,2'-pyrrolidine] scaffolds via 1,3-dipolar cycloaddition of 4-aminopyrazolones, aldehydes, and indolenines.
Nawaz, Shah; Wei, Shiqiang; Huang, Yue; Wang, Wenyao; Qu, Jingping; Wang, Baomin; Organic & biomolecular chemistry 19 (2021) 6964–6968; doi:10.1039/d1ob01135a

data_7158170
_publ_section_title
;
 Diastereoselective synthesis of indolenine-based
 spiro[pyrazolone-4,2'-pyrrolidine] scaffolds via 1,3-dipolar
 cycloaddition of 4-aminopyrazolones, aldehydes, and indolenines.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6964
_journal_page_last               6968
_journal_paper_doi               10.1039/d1ob01135a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C40 H33 Br N4 O'
_chemical_formula_sum            'C40 H33 Br N4 O'
_chemical_formula_weight         665.61
_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     dual
_audit_creation_date             2021-06-11
_audit_creation_method
;
Olex2 1.3-beta
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-06-12 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                75.801(2)
_cell_angle_beta                 69.663(2)
_cell_angle_gamma                66.4250(10)
_cell_formula_units_Z            2
_cell_length_a                   12.2987(7)
_cell_length_b                   12.4224(7)
_cell_length_c                   13.2018(8)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    296.0
_cell_measurement_theta_max      25.462
_cell_measurement_theta_min      2.168
_cell_volume                     1720.08(17)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32619
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_min         1.802
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.232
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5766
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1135 before and 0.0519 after correction.
The Ratio of minimum to maximum transmission is 0.7733.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         7890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0806P)^2^+0.5388P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1582
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5061
_reflns_number_total             7890
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01135a2.cif
_cod_data_source_block           2
_cod_depositor_comments          'Adding full bibliography for 7158170.cif.'
_cod_original_cell_volume        1720.08(18)
_cod_database_code               7158170
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.908
_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 Ternary CH refined with riding coordinates:
 C16(H16), C23(H23), C24(H24)
2.b Aromatic/amide H refined with riding coordinates:
 C40(H40), C38(H38), C37(H37), C17(H17), C15(H15), C19(H19), C11(H11),
 C20(H20), C26(H26), C14(H14), C3(H3A), C30(H30), C22(H22), C13(H13), C21(H21),
 C12(H12), C27(H27), C2(H2), C28(H28), C5(H5), C1(H1), C29(H29), C6(H6)
2.c Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C33(H33A,H33B,H33C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              85491
_shelx_fab_checksum              8624
_olex2_submission_special_instructions 'No special instructions were received'