Photochemical three-component assembly of tri-substituted oxazoles through a carbenic phosphorus-nitrile hybrid ylide formation/trapping cascade.
Ye, Xingchen; Pan, Huaijin; Huang, Yong; Chen, Jiean; Wang, Zhaofeng; Chemical science 15 (2024) 6515–6521; doi:10.1039/d4sc01355g

data_1571401
_publ_section_title
;
 Photochemical three-component assembly of tri-substituted oxazoles
 through a carbenic phosphorus-nitrile hybrid ylide formation/trapping
 cascade.
;
_journal_issue                   17
_journal_name_full               'Chemical science'
_journal_page_first              6515
_journal_page_last               6521
_journal_paper_doi               10.1039/d4sc01355g
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C25 H25 N O P, B F4'
_chemical_formula_sum            'C25 H25 B F4 N O P'
_chemical_formula_weight         473.24
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-14
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_audit_update_record
;
2023-06-13 deposited with the CCDC.	2024-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.0500(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.81460(10)
_cell_length_b                   14.7684(2)
_cell_length_c                   15.0422(2)
_cell_measurement_reflns_used    22788
_cell_measurement_temperature    303.33(10)
_cell_measurement_theta_max      76.7350
_cell_measurement_theta_min      4.0690
_cell_volume                     2399.05(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL n/a (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      303.33(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     34.00 115.00   0.50    0.05    --   46.55  19.00-150.00  162
  2  \w     39.00  83.00   0.50    0.05    --   46.55  65.00  13.00   88
  3  \w     89.00 116.00   0.50    0.05    --   46.55  57.00 120.00   54
  4  \w     59.00  85.00   0.50    0.05    --   46.55  57.00 120.00   52
  5  \w     45.00 105.00   0.50    0.07    --  105.63 -94.00  90.00  120
  6  \w    -16.00  79.00   0.50    0.05    --   46.55 -99.00  30.00  190
  7  \w     37.00 102.00   0.50    0.07    --  105.63 -94.00-120.00  130
  8  \w     36.00  61.00   0.50    0.07    --  105.63 -61.00-180.00   50
  9  \w     34.00  79.00   0.50    0.07    --  105.63 -65.00-122.00   90
 10  \w     34.00  69.00   0.50    0.07    --  105.63 -61.00 -90.00   70
 11  \w     35.00  66.00   0.50    0.07    --  105.63 -61.00 -60.00   62
 12  \w    -24.00  29.00   0.50    0.05    --   46.55 -65.00-122.00  106
 13  \w     33.00  66.00   0.50    0.07    --  105.63 -61.00   0.00   66
 14  \w     36.00  69.00   0.50    0.07    --  105.63 -61.00  30.00   66
 15  \w     97.00 178.00   0.50    0.07    --  105.63  30.00 -60.00  162
 16  \w    132.00 161.00   0.50    0.07    --  105.63  65.00  13.00   58
 17  \w    123.00 170.00   0.50    0.07    --  105.63  45.00-180.00   94
 18  \w    -24.00  28.00   0.50    0.05    --  -46.55  19.00   0.00  104
 19  \w    -50.00 -18.00   0.50    0.05    --  -46.55  65.00  13.00   64
 20  \w    -63.00 -37.00   0.50    0.07    -- -104.00  61.00 120.00   52
 21  \w    -84.00 -34.00   0.50    0.07    -- -104.00  77.00  30.00  100
 22  \w    -74.00 -34.00   0.50    0.07    -- -104.00  65.00  13.00   80
 23  \w    -69.00 -31.00   0.50    0.07    -- -104.00  61.00-120.00   76
 24  \w    -69.00 -44.00   0.50    0.07    -- -104.00  61.00-150.00   50
 25  \w   -121.00 -34.00   0.50    0.05    --  -46.55 -19.00-120.00  174
 26  \w    -90.00 -64.00   0.50    0.05    --  -46.55 -65.00-122.00   52
 27  \w    -54.00 -29.00   0.50    0.05    --  -46.55 -65.00-122.00   50
 28  \w   -112.00 -81.00   0.50    0.07    -- -104.00 -77.00-180.00   62
 29  \w   -168.00-129.00   0.50    0.07    -- -104.00 -77.00 -30.00   78
 30  \w   -171.00-138.00   0.50    0.07    -- -104.00 -65.00-122.00   66
 31  \w   -112.00 -87.00   0.50    0.07    -- -104.00 -77.00 -30.00   50
 32  \w   -175.00-143.00   0.50    0.07    -- -104.00 -30.00-180.00   64
 33  \w   -174.00-116.00   0.50    0.07    -- -104.00 -77.00 120.00  116
 34  \w   -128.00 -81.00   0.50    0.07    -- -104.00 -77.00 150.00   94
 35  \w   -125.00 -87.00   0.50    0.07    -- -104.00 -61.00 150.00   76
 36  \w   -137.00 -91.00   0.50    0.07    -- -104.00 -30.00 150.00   92
 37  \w   -169.00-141.00   0.50    0.07    -- -104.00 -30.00 150.00   56
 38  \w   -175.00-119.00   0.50    0.07    -- -104.00 -15.00 120.00  112
 39  \w   -175.00 -94.00   0.50    0.07    -- -104.00 -30.00  90.00  162
 40  \w   -119.00 -92.00   0.50    0.07    -- -104.00 -30.00 -60.00   54
 41  \w   -128.00 -97.00   0.50    0.07    -- -104.00 -30.00-180.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1134632000
_diffrn_orient_matrix_UB_12      -0.0448662000
_diffrn_orient_matrix_UB_13      0.0480985000
_diffrn_orient_matrix_UB_21      0.0862898000
_diffrn_orient_matrix_UB_22      0.0636184000
_diffrn_orient_matrix_UB_23      -0.0491650000
_diffrn_orient_matrix_UB_31      -0.0057756000
_diffrn_orient_matrix_UB_32      0.0694666000
_diffrn_orient_matrix_UB_33      0.0760878000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29894
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.882
_diffrn_reflns_theta_min         4.094
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.443
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       Block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0659P)^2^+0.7207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1317
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4539
_reflns_number_total             4932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01355g2.cif
_cod_data_source_block           wzf20220913-again_auto
_cod_depositor_comments
'Adding full bibliography for 1571400--1571401.cif.'
_cod_database_code               1571401
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N P F B'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C25(H25)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C14(H14), C18(H18), C2(H2), C24(H24), C16(H16), C20(H20), C17(H17),
 C23(H23), C15(H15), C5(H5), C3(H3), C21(H21), C22(H22), C4(H4)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C27(H27A,H27B,H27C), C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.435
_oxdiff_exptl_absorpt_empirical_full_min 0.560