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_7221824
_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 H8 N2 O2'
_chemical_formula_sum            'C10 H8 N2 O2'
_chemical_formula_weight         188.18
_chemical_melting_point          402.5(15)
_chemical_name_systematic        '2,6-Dimethylbenzo[1,2-d:5,4-d']bis(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                 94.664(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.83460(10)
_cell_length_b                   8.0536(3)
_cell_length_c                   13.7021(5)
_cell_measurement_reflns_used    936
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.7160
_cell_measurement_theta_min      6.3630
_cell_volume                     421.75(2)
_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      100.01(10)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_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  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            1371
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         73.85
_diffrn_reflns_theta_min         6.38
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65049
_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    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             196
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane'
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.013(2)
_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     84
_refine_ls_number_reflns         820
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+0.1194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0952
_reflns_number_gt                759
_reflns_number_total             820
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c5ra15128g3.cif
_cod_data_source_block           an_222_bis_benzoxazole_meme
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '401-404' was changed to '402.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7221824