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_7129532
_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         'C12 H13 N O3'
_chemical_formula_sum            'C12 H13 N O3'
_chemical_formula_weight         219.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0228(5)
_cell_length_b                   9.8396(5)
_cell_length_c                   11.0400(5)
_cell_measurement_reflns_used    7643
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.0180
_cell_measurement_theta_min      4.4820
_cell_volume                     1088.77(9)
_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      100(1)
_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 0.988
_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    -25.00  70.00   0.50    0.22    --   46.95 -78.00 104.00  190
  2  \w     32.00 113.00   0.50    0.90    --  104.75 -78.00 104.00  162
  3  \w     32.00  73.00   0.50    0.90    --  104.75 -61.00 -60.00   82
  4  \w     32.00 109.00   0.50    0.90    --  104.75 -94.00   0.00  154
  5  \w     32.00 109.00   0.50    0.90    --  104.75 -94.00-150.00  154
  6  \w     32.00 117.00   0.50    0.90    --  104.75-125.00-150.00  170
  7  \w     32.00  73.00   0.50    0.90    --  104.75 -61.00  60.00   82
  8  \w     32.00 117.00   0.50    0.90    --  104.75-125.00 150.00  170
  9  \w     88.00 178.00   0.50    0.90    --  104.75  61.00 -90.00  180
 10  \w     92.00 177.00   0.50    0.90    --  104.75  45.00 -30.00  170
 11  \w     82.00 178.00   0.50    0.90    --  104.75  78.00-130.00  192
 12  \w     92.00 177.00   0.50    0.90    --  104.75  45.00-150.00  170
 13  \w     24.00 119.00   0.50    0.22    --   46.95  78.00-130.00  190
 14  \w     24.00  82.00   0.50    0.22    --   46.95  77.00  30.00  116
 15  \w     92.00 177.00   0.50    0.90    --  104.75  45.00 150.00  170
 16  \w     24.00 119.00   0.50    0.22    --   46.95  77.00 -30.00  190
 17  \w    -24.00  29.00   0.50    0.22    --  -46.95  19.00-120.00  106
 18  \w    -24.00  29.00   0.50    0.22    --  -46.95  19.00-150.00  106
 19  \w    -70.00  26.00   0.50    0.22    --  -46.95  78.00-130.00  192
 20  \w    -27.00  28.00   0.50    0.22    --   46.95 -19.00 120.00  110
 21  \w    -40.00  26.00   0.50    0.22    --  -46.95  37.00  90.00  132
 22  \w    -69.00 -29.00   0.50    0.90    -- -102.00  61.00  90.00   80
 23  \w    -69.00 -29.00   0.50    0.90    -- -102.00  61.00 120.00   80
 24  \w    -69.00 -29.00   0.50    0.90    -- -102.00  61.00  60.00   80
 25  \w    -69.00 -29.00   0.50    0.90    -- -102.00  61.00 -60.00   80
 26  \w    -69.00 -29.00   0.50    0.90    -- -102.00  61.00-180.00   80
 27  \w   -109.00 -29.00   0.50    0.90    -- -102.00  78.00-130.00  160
 28  \w   -117.00 -29.00   0.50    0.90    -- -102.00 125.00   0.00  176
 29  \w   -118.00 -32.00   0.50    0.22    --  -46.95 -57.00 150.00  172
 30  \w   -119.00 -24.00   0.50    0.22    --  -46.95 -78.00 104.00  190
 31  \w   -119.00 -71.00   0.50    0.22    --  -46.95-125.00 -90.00   96
 32  \w   -119.00 -71.00   0.50    0.22    --  -46.95-125.00-180.00   96
 33  \w   -175.00 -89.00   0.50    0.90    -- -102.00 -30.00 -30.00  172
 34  \w   -175.00 -79.00   0.50    0.90    -- -102.00 -78.00 104.00  192
 35  \w   -175.00 -79.00   0.50    0.90    -- -102.00 -77.00  90.00  192
 36  \w   -175.00 -88.00   0.50    0.90    -- -102.00 -15.00   0.00  174
 37  \w   -175.00 -89.00   0.50    0.90    -- -102.00 -30.00-180.00  172
 38  \w   -175.00 -81.00   0.50    0.90    -- -102.00 -94.00  60.00  188
;
_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      0.1282518000
_diffrn_orient_matrix_UB_12      -0.0764029000
_diffrn_orient_matrix_UB_13      0.0360169000
_diffrn_orient_matrix_UB_21      -0.0272135000
_diffrn_orient_matrix_UB_22      -0.1063974000
_diffrn_orient_matrix_UB_23      -0.0994764000
_diffrn_orient_matrix_UB_31      0.0801236000
_diffrn_orient_matrix_UB_32      0.0857988000
_diffrn_orient_matrix_UB_33      -0.0910452000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18412
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.770
_diffrn_reflns_theta_min         4.494
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59969
_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 light colourless'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 828 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.0037(16)
_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   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2207
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0955P)^2^+0.2696P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1625
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                2039
_reflns_number_total             2207
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06529g2.cif
_cod_data_source_block           20210615b
_cod_database_code               7129532
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C1H1N1O1
_diffrn_oxdiff_digest_frames
;
0179eb7419a8aabd035365d23dc4e0ea1300065fa83
;
_diffrn_oxdiff_digest_hkl
;
019563f2eddd221f88fbeca3211784cb56cbdc
;
_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:
 C9(H9A,H9B), C13(H13A,H13B), C12(H12A,H12B), C11(H11A,H11B)
1.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C2(H2), C4(H4), C3(H3)
;
_shelx_res_checksum              86642
_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 1.622
_oxdiff_exptl_absorpt_empirical_full_min 0.606