Conjugate addition/cyclization of propanal with isatylidene malononitriles: an efficient one-pot organocatalytic approach for the synthesis of 3'-methyl spiro[2<i>H</i>-pyran-3,4'-indoline].
Patil, Baliram R.; Nichinde, Chandrakant B.; Girase, Amardipsing S.; Chaudhari, Suryakant S.; Kinage, Anil K.; Organic & biomolecular chemistry 23 (2025) 6214–6219; doi:10.1039/d5ob00553a

data_7160585
_publ_section_title
;
 Conjugate addition/cyclization of propanal with isatylidene
 malononitriles: an efficient one-pot organocatalytic approach for the
 synthesis of 3'-methyl spiro[2<i>H</i>-pyran-3,4'-indoline].
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6214
_journal_page_last               6219
_journal_paper_doi               10.1039/d5ob00553a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C16 H17 N3 O2'
_chemical_formula_sum            'C16 H17 N3 O2'
_chemical_formula_weight         283.32
_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             2025-03-28
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-03-28 deposited with the CCDC.	2025-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.146(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3030(13)
_cell_length_b                   8.9537(13)
_cell_length_c                   17.411(2)
_cell_measurement_reflns_used    6608
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.56
_cell_volume                     1439.0(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.1079
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21631
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.030
_diffrn_reflns_theta_max         25.030
_diffrn_reflns_theta_min         2.206
_diffrn_source_current           0.95
_diffrn_source_power             0.0475
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1139 before and 0.0835 after correction.
The Ratio of minimum to maximum transmission is 0.8080.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.268
_exptl_crystal_size_min          0.215
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2546
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0626
_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^)+(0.0492P)^2^+1.0106P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1334
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1832
_reflns_number_total             2546
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00553a2.cif
_cod_data_source_block           4Bb
_cod_depositor_comments
'Adding full bibliography for 7160584--7160585.cif.'
_cod_database_code               7160585
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.973
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C4(H4)
1.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C15(H15A,H15B)
1.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C11(H11)
1.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              99608
_olex2_submission_special_instructions 'No special instructions were received'