One-pot synthesis of 3,5-disubstituted and polysubstituted phenols from acyclic precursors.
Qian, Jinlong; Yi, Wenbin; Huang, Xin; Miao, Yongbo; Zhang, Junkai; Cai, Chun; Zhang, Wei; Organic letters 17 (2015) 1090–1093; doi:10.1021/ol503615n

data_1518725
_publ_section_title
;
 One-pot synthesis of 3,5-disubstituted and polysubstituted phenols from
 acyclic precursors.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1090
_journal_page_last               1093
_journal_paper_doi               10.1021/ol503615n
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C18 H12 F N O3'
_chemical_formula_weight         309.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.82(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.798(6)
_cell_length_b                   11.416(15)
_cell_length_c                   31.20(4)
_cell_measurement_reflns_used    3186
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.78
_cell_measurement_theta_min      2.61
_cell_volume                     1353(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            6556
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.31
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9788
_exptl_absorpt_correction_T_min  0.9711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       0.0086(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0868
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0142P)^2^+3.9502P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1799
_refine_ls_wR_factor_ref         0.1937
_reflns_number_gt                1848
_reflns_number_total             2330
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol503615n_si_002.cif
_cod_data_source_block           20140610lmf2_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 1518725--1518726.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               1518725