Visible light C–H amidation of heteroarenes with benzoyl azides
Brachet, E.; Ghosh, T.; Ghosh, I.; König, B.; Chem. Sci. 6 (2015) 987–; doi:10.1039/C4SC02365J

data_1518141
_publ_section_title
;
 Visible light C--H amidation of heteroarenes with benzoyl azides
;
_journal_issue                   2
_journal_name_full               'Chem. Sci.'
_journal_page_first              987
_journal_paper_doi               10.1039/C4SC02365J
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C13 H14 N2 O2'
_chemical_formula_sum            'C13 H14 N2 O2'
_chemical_formula_weight         230.26
_chemical_name_systematic
2-(4-Chlorophenyl)-4-methyl-4-phenyl-4,5-dihydrooxazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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_date             2014-07-02
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.23 svn.r2946 for OlexSys, GUI svn.r4855)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.161(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.6434(3)
_cell_length_b                   10.03245(18)
_cell_length_c                   20.8570(4)
_cell_measurement_reflns_used    5594
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      63.2750
_cell_measurement_theta_min      3.8740
_cell_volume                     2372.35(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2548
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
  1 omega -124.00  -79.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6587  -99.0000  -60.0000 90

  2 omega -123.00  -79.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6587  -99.0000   90.0000 88

  3 omega -124.00  -79.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6587  -99.0000 -150.0000 90

  4 omega  -69.00   -6.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000  -90.0000 126

  5 omega   64.00  153.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       86.4674   45.0000 -180.0000 178

  6 omega   64.00  145.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       86.4674   45.0000   90.0000 162

  7 omega    2.00  105.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       86.4674  -94.0000  -30.0000 206

  8 omega -120.00   -8.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6587  -77.0000 -150.0000 224

  9 omega -117.00  -10.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6587  -67.0000  -37.0000 214

 10 omega   12.00   42.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       86.4674  -45.0000   90.0000 60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0540875000
_diffrn_orient_matrix_UB_12      0.1019833000
_diffrn_orient_matrix_UB_13      0.0398623000
_diffrn_orient_matrix_UB_21      -0.0741198000
_diffrn_orient_matrix_UB_22      0.0587027000
_diffrn_orient_matrix_UB_23      -0.0645227000
_diffrn_orient_matrix_UB_31      -0.1002089000
_diffrn_orient_matrix_UB_32      -0.0985891000
_diffrn_orient_matrix_UB_33      0.0027279000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9809
_diffrn_reflns_theta_full        63.48
_diffrn_reflns_theta_max         63.48
_diffrn_reflns_theta_min         3.90
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.1345
_exptl_crystal_size_mid          0.1066
_exptl_crystal_size_min          0.0361
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         3758
_refine_ls_number_restraints     190
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0559P)^2^+0.6172P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                3356
_reflns_number_total             3758
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc02365j2.cif
_cod_data_source_block           n071
_cod_depositor_comments          'Adding full bibliography for 1518141.cif.'
_cod_original_cell_volume        2372.35(8)
_cod_database_code               1518141
_chemical_oxdiff_formula         'C13 H14 N2 O2'
_reflns_odcompleteness_completeness 95.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.00
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C22-N4 \\sim C22A-N4A
 with sigma of 0.001
 C22-C23 \\sim C22A-C23A
 with sigma of 0.001
 N4A-C25A \\sim N4-C25
 with sigma of 0.001
 C24A-C25A \\sim C25-C24
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
N4 \\sim C25 \\sim C26 \\sim C23 \\sim C22 \\sim C24 \\sim N4A \\sim C25A \\sim
C24A \\sim C23A \\sim C22A \\sim C26A: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.005
4. Others
 Sof(H3B)=Sof(N4A)=Sof(C25A)=Sof(H25A)=Sof(C24A)=Sof(H24A)=Sof(C23A)=Sof(H23A)=
 Sof(C22A)=Sof(C26A)=Sof(H26D)=Sof(H26E)=Sof(H26F)=1-FVAR(1)
 Sof(H3A)=Sof(N4)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=
 Sof(C23)=Sof(H23)=Sof(C22)=Sof(C24)=Sof(H24)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3A), N3(H3B), C10(H10), C19(H19), C15(H15), C11(H11), C18(H18),
 C2(H2), C16(H16), C25(H25), C6(H6), C12(H12), C5(H5), C23(H23), C3(H3),
 C24(H24), C25A(H25A), C24A(H24A), C23A(H23A)
5.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C7(H7A,H7B,H7C), C13(H13A,H13B,H13C), C26(H26A,H26B,
 H26C), C26A(H26D,H26E,H26F)
;
_olex2_submission_special_instructions 'No special instructions were received'