Unlocking enhanced reactivity of hexafluoroisopropanol: a sustainable atom economical approach to selective cascade di-π-functionalization of allenamides
Mirza, Yafia Kousin; Bera, Partha Sarathi; Nandini, R.; Talukdar, Dhrubajyoti; Mohite, Sachin Balaso; Mane, Manoj V.; Bera, Milan; Green Chemistry 27 (2025) 8972–8979; doi:10.1039/D5GC01273B

data_7250598
_publ_section_title
;
 Unlocking enhanced reactivity of hexafluoroisopropanol: a sustainable
 atom economical approach to selective cascade di-\p-functionalization of
 allenamides
;
_journal_issue                   29
_journal_name_full               'Green Chemistry'
_journal_page_first              8972
_journal_page_last               8979
_journal_paper_doi               10.1039/D5GC01273B
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C16 H15 N O4'
_chemical_formula_sum            'C16 H15 N O4'
_chemical_formula_weight         285.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_Hall           '-C 2ac 2'
_space_group_name_H-M_alt        'C m c e'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-05-20
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-01 deposited with the CCDC.	2025-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.8069(15)
_cell_length_b                   18.566(5)
_cell_length_c                   20.810(4)
_cell_measurement_reflns_used    1319
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      19.48
_cell_measurement_theta_min      2.19
_cell_volume                     2629.9(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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)'
_diffrn_ambient_temperature      173.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1218
_diffrn_reflns_av_unetI/netI     0.0895
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19512
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.194
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6087
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1273 before and 0.0813 after correction.
The Ratio of minimum to maximum transmission is 0.8168.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       needle
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1264
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0668
_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^)+(0.0395P)^2^+6.0406P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1712
_refine_ls_wR_factor_ref         0.1867
_reflns_Friedel_coverage         0.000
_reflns_number_gt                903
_reflns_number_total             1264
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc01273b2.cif
_cod_data_source_block           small61_1_0f
_cod_depositor_comments          'Adding full bibliography for 7250598.cif.'
_cod_original_cell_volume        2630.0(10)
_cod_original_sg_symbol_Hall     '-C 2bc 2'
_cod_database_code               7250598
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.969
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
N1 \\sim C13 \\sim C14 \\sim C15 \\sim C16: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 N1, C13, C14, C15, C16
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: O3(0.5) O4(0.5) C10(0.5) H10A(0.5) H10B(0.5) C11(0.5) H11A(0.5)
 H11B(0.5) C12(0.5) H12(0.5) N1(0.5) C13(0.5) C14(0.5) H14A(0.5) H14B(0.5)
 C15(0.5) H15A(0.5) H15B(0.5) C16(0.5) H16A(0.5) H16B(0.5)
5.a Ternary CH refined with riding coordinates:
 C12(H12)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
;
_shelx_res_checksum              35498
_shelx_hkl_checksum              85056
_olex2_submission_special_instructions 'No special instructions were received'