Synthesis of functionalised isochromans: epoxides as aldehyde surrogates in hexafluoroisopropanol
Muller, Cyprien; Horký, Filip; Vayer, Marie; Golushko, Andrei; Lebœuf, David; Moran, Joseph; Chemical Science 14 (2023) 2983–2989; doi:10.1039/D2SC06692K

data_1568413
_publ_section_title
;
 Synthesis of functionalised isochromans: epoxides as aldehyde surrogates
 in hexafluoroisopropanol
;
_journal_issue                   11
_journal_name_full               'Chemical Science'
_journal_page_first              2983
_journal_page_last               2989
_journal_paper_doi               10.1039/D2SC06692K
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C22 H14 F5 N O3'
_chemical_formula_sum            'C22 H14 F5 N O3'
_chemical_formula_weight         435.34
_chemical_name_systematic
1-(4-nitrobenzyl)-4-(perfluorophenyl)isochromane
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc2f5dz0
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-02-02 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.700(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
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_cell_length_b                   6.5104(3)
_cell_length_c                   14.0699(6)
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      66.37
_cell_measurement_theta_min      3.24
_cell_volume                     3750.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       '\f and \w shuterless scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            72332
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.527
_diffrn_reflns_theta_max         66.527
_diffrn_reflns_theta_min         2.158
_diffrn_source                   'Cu-ImuS DIAMOND microfocus tube'
_exptl_absorpt_coefficient_mu    1.186
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6091
_exptl_absorpt_correction_type   multi-scan
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_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_description       plate
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_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Hx'
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.817
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.0021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         6631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0826
_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^)+(0.1247P)^2^+6.2158P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2203
_refine_ls_wR_factor_ref         0.2430
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4677
_reflns_number_total             6631
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06692k2.cif
_cod_data_source_block           jmcm220131
_cod_depositor_comments
'Adding full bibliography for 1568413--1568416.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1568413
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.815
_shelx_estimated_absorpt_t_max   0.932
_shelx_res_checksum              17387