Visible-light-induced photocatalytic oxytrifluoromethylation of N-allylamides for the synthesis of CF3-containing oxazolines and benzoxazines
Qiao-Hui Deng; Jia-Rong Chen; Qiang Wei; Quan-Qing Zhao; Liang-Qiu Lu; Wen-Jing Xiao; Chem.Commun. 51 (2015) 3537–; doi:10.1039/C4cc10217G

data_7116561
_publ_section_title
;
 Visible-light-induced photocatalytic oxytrifluoromethylation of
 N-allylamides for the synthesis of CF3-containing oxazolines and
 benzoxazines
;
_journal_name_full               Chem.Commun.
_journal_page_first              3537
_journal_paper_doi               10.1039/C4cc10217G
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C26 H31 N O5'
_chemical_formula_sum            'C26 H31 N O5'
_chemical_formula_weight         437.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_audit_update_record
;
2014-12-13 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.508(5)
_cell_length_b                   8.3721(14)
_cell_length_c                   19.678(3)
_cell_measurement_reflns_used    9835
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.91
_cell_measurement_theta_min      2.18
_cell_volume                     4861.3(14)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            36979
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.170
_diffrn_reflns_theta_min         1.380
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1135 before and 0.0540 after correction.
The Ratio of minimum to maximum transmission is 0.9058.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       Block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         5395
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0889
_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^)+(0.1652P)^2^+2.6198P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2568
_refine_ls_wR_factor_ref         0.2908
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3711
_reflns_number_total             5395
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc10217g2.cif
_cod_data_source_block           t
_cod_database_code               7116561
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C20-C21 = C24-C23
 1.54 with sigma of 0.005
 C25-C26 \\sim C25-C26B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C28) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C26B) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
Uanis(C26) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: O2(0.5) C26(0.7) H26A(0.7) H26B(0.7) H26C(0.7) O2B(0.5) C26B(0.3)
 H26D(0.3) H26E(0.3) H26F(0.3)
5.a Ternary CH refined with riding coordinates:
 C3(H3)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C23(H23A,H23B), C20(H20A,H20B)
5.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C5(H5), C6(H6), C14(H14), C16(H16), C9(H9),
 C10(H10)
5.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C24(H24A,H24B,H24C), C28(H28A,H28B,H28C), C27(H27A,H27B,
 H27C), C21(H21A,H21B,H21C), C26B(H26D,H26E,H26F)
;
_olex2_submission_special_instructions 'No special instructions were received'