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_7160584
_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         'C15 H12 F3 N3 O2, C3 H6 O'
_chemical_formula_sum            'C18 H18 F3 N3 O3'
_chemical_formula_weight         381.35
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-03-13
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-03-13 deposited with the CCDC.	2025-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.202(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.564(5)
_cell_length_b                   11.352(4)
_cell_length_c                   11.354(4)
_cell_measurement_reflns_used    3777
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.28
_cell_measurement_theta_min      2.28
_cell_volume                     1866.2(11)
_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)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_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  0.0634
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24235
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.166
_diffrn_reflns_theta_max         25.166
_diffrn_reflns_theta_min         1.406
_diffrn_source_current           19.0
_diffrn_source_power             0.76
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0903 before and 0.0628 after correction.
The Ratio of minimum to maximum transmission is 0.9236.
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    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.185
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3327
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0518
_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^)+(0.0518P)^2^+2.0785P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1361
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2463
_reflns_number_total             3327
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00553a2.cif
_cod_data_source_block           4Ao
_cod_depositor_comments
'Adding full bibliography for 7160584--7160585.cif.'
_cod_original_cell_volume        1866.3(11)
_cod_database_code               7160584
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.971
_olex2_refinement_description
;
1. Restrained distances
 F1-C15 \\sim F1'-C15
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(F1') \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3. Others
 Sof(F1')=1-FVAR(1)
 Sof(F1)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C4(H4)
4.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
4.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C9(H9), C11(H11), C10(H10)
4.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C7(H7A,H7B,H7C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              93548
_olex2_submission_special_instructions 'No special instructions were received'