Rearrangement-driven divergent synthesis: a metal-free tandem annulation for CF3-functionalized 1-(aminomethyl)naphthalen-2-ols and 1-(2-naphthyl)azetidines
Wang, Bin; Li, Zekun; Cao, Hua; Green Chemistry 27 (2025) 15074–15080; doi:10.1039/D5GC05046D

data_7251255
_publ_section_title
;
 Rearrangement-driven divergent synthesis: a metal-free tandem annulation
 for CF3-functionalized 1-(aminomethyl)naphthalen-2-ols and
 1-(2-naphthyl)azetidines
;
_journal_issue                   47
_journal_name_full               'Green Chemistry'
_journal_page_first              15074
_journal_page_last               15080
_journal_paper_doi               10.1039/D5GC05046D
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C21 H20 F3 N O'
_chemical_formula_sum            'C21 H20 F3 N O'
_chemical_formula_weight         359.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-06
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-05-16 deposited with the CCDC.	2025-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.692(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5424(5)
_cell_length_b                   19.5291(8)
_cell_length_c                   10.0245(5)
_cell_measurement_reflns_used    2391
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.4960
_cell_measurement_theta_min      4.5100
_cell_volume                     1735.82(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -12.00  29.00   1.00    3.00    --  -41.11  38.00 -60.00   41
  2  \w    -65.00 -26.00   1.00    3.00    --  -41.11  38.00 -60.00   39
  3  \w   -117.00 -31.00   1.00    3.00    --  -41.11 -77.00 120.00   86
  4  \w      1.00  81.00   1.00    3.00    --   41.11 -99.00-120.00   80
  5  \w     33.00 108.00   1.00    6.00    --  107.58 -94.00 -30.00   75
  6  \w     78.00 109.00   1.00    6.00    --  107.58-125.00 120.00   31
  7  \w     38.00  64.00   1.00    6.00    --  107.58 -30.00 150.00   26
  8  \w     35.00 135.00   1.00    6.00    --  107.58 -61.00 150.00  100
  9  \w    108.00 136.00   1.00    6.00    --  107.58 -30.00 150.00   28
 10  \w    100.00 129.00   1.00    6.00    --  107.58 125.00  60.00   29
 11  \w     94.00 169.00   1.00    6.00    --  107.58 125.00 -90.00   75
 12  \w     92.00 155.00   1.00    6.00    --  107.58  45.00-120.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0413027000
_diffrn_orient_matrix_UB_12      0.0631094000
_diffrn_orient_matrix_UB_13      -0.0701413000
_diffrn_orient_matrix_UB_21      -0.0361097000
_diffrn_orient_matrix_UB_22      0.0470349000
_diffrn_orient_matrix_UB_23      0.1064556000
_diffrn_orient_matrix_UB_31      0.1648433000
_diffrn_orient_matrix_UB_32      -0.0054894000
_diffrn_orient_matrix_UB_33      0.1053706000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6793
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.665
_diffrn_reflns_theta_min         4.528
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.892
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3408
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0552
_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^)+(0.0937P)^2^+0.0881P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1601
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2708
_reflns_number_total             3408
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc05046d2.cif
_cod_data_source_block           38
_cod_depositor_comments
'Adding full bibliography for 7251254--7251256.cif.'
_cod_original_cell_volume        1735.82(15)
_cod_database_code               7251255
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C10(H10), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C21(H21A,H21B,H21C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              14751
_shelx_hkl_checksum              97768
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.551
_oxdiff_exptl_absorpt_empirical_full_min 0.667