Synthesis of β-Nitro Ketone from Geminal Bromonitroalkane and Silyl Enol Ether by Visible Light Photoredox Catalysis
Cao, Haoying; Ma, Shanshan; Feng, Yanhong; Guo, Yawen; Jiao, Peng; Chemical Communications  (2022) –; doi:10.1039/D1CC06529G

data_7129529
_publ_section_title
;
 Synthesis of \b-Nitro Ketone from Geminal Bromonitroalkane and Silyl Enol
 Ether by Visible Light Photoredox Catalysis
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06529G
_journal_year                    2022
_chemical_formula_moiety         'C9 H9 N O3'
_chemical_formula_sum            'C9 H9 N O3'
_chemical_formula_weight         179.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-09-01
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_audit_update_record
;
2021-09-05 deposited with the CCDC.	2022-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.654(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.61652(15)
_cell_length_b                   8.2450(3)
_cell_length_c                   9.0227(3)
_cell_measurement_reflns_used    6319
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.9200
_cell_measurement_theta_min      7.2380
_cell_volume                     417.38(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_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     92.00 177.00   0.50    0.05    --  104.75  45.00 166.00  170
  2  \w     34.00 119.00   0.50    0.05    --   46.95  45.00 166.00  170
  3  \w     24.00 119.00   0.50    0.05    --   46.95  77.00 -90.00  190
  4  \w    -25.00  53.00   0.50    0.05    --   46.95 -45.00  15.00  156
  5  \w     32.00  73.00   0.50    0.05    --  104.75 -61.00-150.00   82
  6  \w     32.00  73.00   0.50    0.05    --  104.75 -61.00-120.00   82
  7  \w     32.00  73.00   0.50    0.05    --  104.75 -61.00 -60.00   82
  8  \w     32.00  73.00   0.50    0.05    --  104.75 -61.00   0.00   82
  9  \w    -24.00  29.00   0.50    0.05    --  -46.95  19.00 150.00  106
 10  \w    -49.00  25.00   0.50    0.05    --  -46.95  45.00 166.00  148
 11  \w     15.00  95.00   0.50    0.05    --   46.95-125.00-120.00  160
 12  \w     32.00 117.00   0.50    0.05    --  104.75-125.00-180.00  170
 13  \w    -24.00  29.00   0.50    0.05    --  -46.95  19.00 -30.00  106
 14  \w    -69.00 -29.00   0.50    0.05    -- -102.00  61.00   0.00   80
 15  \w    -69.00 -29.00   0.50    0.05    -- -102.00  61.00-150.00   80
 16  \w    -69.00 -29.00   0.50    0.05    -- -102.00  61.00 -60.00   80
 17  \w    -69.00 -29.00   0.50    0.05    -- -102.00  61.00 -30.00   80
 18  \w    -69.00 -29.00   0.50    0.05    -- -102.00  61.00  30.00   80
 19  \w   -119.00 -34.00   0.50    0.05    --  -46.95 -45.00  15.00  170
 20  \w   -119.00 -24.00   0.50    0.05    --  -46.95 -77.00 120.00  190
 21  \w   -119.00 -68.00   0.50    0.05    --  -46.95 -77.00   0.00  102
 22  \w   -119.00 -30.00   0.50    0.05    --  -46.95 -61.00 -81.58  178
 23  \w   -119.00 -24.00   0.50    0.05    --  -46.95 -77.00-150.00  190
 24  \w   -175.00 -78.00   0.50    0.05    -- -102.00 -79.00 -47.82  194
 25  \w   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00 -60.00  192
 26  \w   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00-120.00  192
 27  \w   -175.00 -85.00   0.50    0.05    -- -102.00 -61.00-120.00  180
 28  \w   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00 -90.00  192
 29  \w   -174.00 -89.00   0.50    0.05    -- -102.00 -45.00-120.00  170
 30  \w   -174.00 -88.00   0.50    0.05    -- -102.00 -50.00 -37.48  172
 31  \w   -174.00 -89.00   0.50    0.05    -- -102.00 -45.00  15.00  170
 32  \w   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00 120.00  192
 33  \w   -175.00 -89.00   0.50    0.05    -- -102.00 -30.00  90.00  172
 34  \w   -174.00 -89.00   0.50    0.05    -- -102.00 -45.00 -30.00  170
 35  \w   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00 -30.00  192
 36  \w   -175.00 -76.00   0.50    0.05    -- -102.00 -83.00 -59.57  198
 37  \w   -119.00 -71.00   0.50    0.05    --  -46.95-125.00-180.00   96
;
_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      0.0230476000
_diffrn_orient_matrix_UB_12      -0.0009359000
_diffrn_orient_matrix_UB_13      -0.1694759000
_diffrn_orient_matrix_UB_21      0.2273730000
_diffrn_orient_matrix_UB_22      0.1039461000
_diffrn_orient_matrix_UB_23      0.0179600000
_diffrn_orient_matrix_UB_31      0.1521247000
_diffrn_orient_matrix_UB_32      -0.1553075000
_diffrn_orient_matrix_UB_33      0.0129810000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7648
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.884
_diffrn_reflns_theta_min         4.907
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       plate
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 710 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.14(16)
_refine_ls_extinction_coef       0.019(4)
_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   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1631
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0521P)^2^+0.1073P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0906
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                1615
_reflns_number_total             1631
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06529g2.cif
_cod_data_source_block           20210717c
_cod_database_code               7129529
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_digest_frames
;
01eadae72a9e5f4d4c49880376dadc746f00142653c
;
_diffrn_oxdiff_digest_hkl
;
01da570ffeccb6717f292d8d0c6033dc6f665f
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
1.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C5(H5), C3(H3), C4(H4)
;
_shelx_res_checksum              18599
_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 2.261
_oxdiff_exptl_absorpt_empirical_full_min 0.551