One-pot synthesis of 2-naphthols from nitrones and MBH adducts via decarboxylative N–O bond cleavage
Han, Sang Hoon; Pandey, Ashok Kumar; Lee, Heeyoung; Kim, Saegun; Kang, Dahye; Jung, Young Hoon; Kim, Hyung Sik; Hong, Sungwoo; Kim, In Su; Organic Chemistry Frontiers 5 (2018) 3210–; doi:10.1039/C8QO00988K

data_1554484
_publ_section_title
;
 One-pot synthesis of 2-naphthols from nitrones and MBH adducts via
 decarboxylative N--O bond cleavage
;
_journal_issue                   22
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3210
_journal_paper_doi               10.1039/C8QO00988K
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C11 H9 F O2'
_chemical_formula_weight         192.18
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'APEX2 v2014.1-1'
_audit_update_record
;
2018-07-26 deposited with the CCDC.
2018-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9693(3)
_cell_length_b                   5.8579(3)
_cell_length_c                   31.3863(17)
_cell_measurement_reflns_used    7005
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.54
_cell_measurement_theta_min      2.60
_cell_volume                     913.64(9)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2014.5.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0540
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            29989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.759
_diffrn_reflns_theta_min         2.596
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
; 
 Flack x determined using 605 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.5(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0506
_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^)+(0.0397P)^2^+0.2050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1060
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1864
_reflns_number_total             2375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00988k2.cif
_cod_data_source_block           global
_cod_database_code               1554484
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.995
_shelxl_version_number           2013-4
_shelx_res_checksum              28687
_shelx_hkl_checksum              5689