One-pot synthesis of benzoxazoles via the metal-free ortho-C-H functionalization of phenols with nitroalkanes
Aksenov, Nicolai A.; Aksenov, Alexander V.; Nadein, Oleg N.; Aksenov, Dmitrii A.; Smirnov, Alexander N.; Rubin, Michael; RSC Adv.  (2015) –; doi:10.1039/C5RA15128G

data_7221823
_publ_section_title
;
 One-pot synthesis of benzoxazoles via the metal-free ortho-C-H
 functionalization of phenols with nitroalkanes
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA15128G
_journal_year                    2015
_chemical_formula_moiety         'C10 H11 N O'
_chemical_formula_sum            'C10 H11 N O'
_chemical_formula_weight         161.20
_chemical_melting_point          366
_chemical_name_common            2,5,6-Trimethylbenzo[d]oxazole
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-07-25 deposited with the CCDC.
2015-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.528(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1944(2)
_cell_length_b                   11.6799(3)
_cell_length_c                   11.8941(3)
_cell_measurement_temperature    100(10)
_cell_measurement_theta_max      74.160
_cell_volume                     857.85(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(10)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3058
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         74.16
_diffrn_reflns_theta_min         5.32
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0209(18)
_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   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1675
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0704P)^2^+0.1718P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1191
_reflns_number_gt                1538
_reflns_number_total             1751
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c5ra15128g2.cif
_cod_data_source_block           an_555_256trimebenzoxazole
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7221823