Base controlled rongalite-mediated reductive aldol/cyclization and dimerization of isatylidene malononitriles/cyanoacetates
Chaudhari, Suryakant S.; Nichinde, Chandrakant B.; Patil, Baliram R.; Girase, Amardipsing S.; Rama Krishna, Gamidi; Kinage, Anil K.; Organic & Biomolecular Chemistry 22 (2024) 1727–1732; doi:10.1039/D3OB01794J

data_7159787
_publ_section_title
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 Base controlled rongalite-mediated reductive aldol/cyclization and
 dimerization of isatylidene malononitriles/cyanoacetates
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_journal_issue                   8
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1727
_journal_page_last               1732
_journal_paper_doi               10.1039/D3OB01794J
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C28 H24 N6 O4, H2 O'
_chemical_formula_sum            'C28 H26 N6 O5'
_chemical_formula_weight         526.55
_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             2023-07-24
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-08-19 deposited with the CCDC.	2024-01-29 downloaded from the CCDC.
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_cell_angle_alpha                90
_cell_angle_beta                 113.305(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4292(12)
_cell_length_b                   9.9284(8)
_cell_length_c                   17.7983(16)
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.42
_cell_measurement_theta_min      2.33
_cell_volume                     2504.0(4)
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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  0.1022
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            123205
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         2.333
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6143
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1473 before and 0.0841 after correction.
The Ratio of minimum to maximum transmission is 0.8236.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0034(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5466
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      16.018
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0474P)^2^+1.2558P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1032
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4604
_reflns_number_total             5466
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01794j2.cif
_cod_data_source_block           3h
_cod_depositor_comments
'Adding full bibliography for 7159784--7159787.cif.'
_cod_database_code               7159787
_publcif_datablock.id            {ad868439-4a6b-4757-9451-8e7769778005}
_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. Restrained distances
 O4-H25
 0.82 with sigma of 0.01
 O4-H26
 0.82 with sigma of 0.01
 H25-H26
 1.296731 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C8(H8A,H8B), C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27), C28(H28)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              51306
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
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