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_7129527
_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         'C18 H21 N O3'
_chemical_formula_sum            'C18 H21 N O3'
_chemical_formula_weight         299.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 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                   6.58510(10)
_cell_length_b                   10.44770(10)
_cell_length_c                   21.3750(2)
_cell_measurement_reflns_used    13189
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.1930
_cell_measurement_theta_min      4.1210
_cell_volume                     1470.58(3)
_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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.978
_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     34.00 121.00   0.50    0.05    --   46.95  19.00 -90.00  174
  2  \w     35.00 120.00   0.50    0.05    --   46.95  37.00 120.00  170
  3  \w     32.00 118.00   0.50    0.05    --   46.95  57.00 150.00  172
  4  \w     91.00 178.00   0.50    0.05    --  104.75  33.00 135.00  174
  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 -60.00   82
  7  \w     32.00  73.00   0.50    0.05    --  104.75 -61.00 -30.00   82
  8  \w     32.00  73.00   0.50    0.05    --  104.75 -61.00 120.00   82
  9  \w     32.00 117.00   0.50    0.05    --  104.75-125.00 150.00  170
 10  \w     32.00 109.00   0.50    0.05    --  104.75 -95.00 147.00  154
 11  \w     32.00 109.00   0.50    0.05    --  104.75 -94.00  30.00  154
 12  \w     32.00 109.00   0.50    0.05    --  104.75 -94.00 -90.00  154
 13  \w    -24.00  29.00   0.50    0.05    --  -46.95  19.00 -90.00  106
 14  \w    -40.00  26.00   0.50    0.05    --  -46.95  37.00-180.00  132
 15  \w   -111.00 -29.00   0.50    0.05    -- -102.00 109.00 -14.00  164
 16  \w   -103.00 -29.00   0.50    0.05    -- -102.00  77.00 120.00  148
 17  \w   -175.00 -88.00   0.50    0.05    -- -102.00 -33.00 -23.00  174
 18  \w   -121.00 -33.00   0.50    0.05    --  -46.95 -33.00 -23.00  176
 19  \w   -175.00 -88.00   0.50    0.05    -- -102.00 -15.00-120.00  174
;
_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      -0.0548021000
_diffrn_orient_matrix_UB_12      -0.0663231000
_diffrn_orient_matrix_UB_13      -0.0621457000
_diffrn_orient_matrix_UB_21      -0.0819465000
_diffrn_orient_matrix_UB_22      0.1276810000
_diffrn_orient_matrix_UB_23      -0.0257350000
_diffrn_orient_matrix_UB_31      0.2121047000
_diffrn_orient_matrix_UB_32      0.0322463000
_diffrn_orient_matrix_UB_33      -0.0259404000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13735
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.340
_diffrn_reflns_theta_min         4.137
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69133
_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    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1187 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_coef       0.0077(9)
_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   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0275
_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^)+(0.0403P)^2^+0.4092P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0741
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                2948
_reflns_number_total             2971
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06529g2.cif
_cod_data_source_block           20210624c
_cod_database_code               7129527
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C1H1N1O1
_diffrn_oxdiff_digest_frames
;
011aac632d26135ebc790882d7763b7afd00116e415
;
_diffrn_oxdiff_digest_hkl
;
0178f248c2132d26f383d7a6c6f274fa3ede2a
;
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C10(H10), C1(H1), C3(H3), C4(H4)
1.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C11(H11A,H11B), C2(H2A,H2B), C6(H6A,H6B)
1.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C21(H21), C18(H18), C20(H20), C19(H19)
;
_shelx_res_checksum              4660
_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 1.489
_oxdiff_exptl_absorpt_empirical_full_min 0.563