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_7129531
_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         'C11 H13 N O3'
_chemical_formula_sum            'C11 H13 N O3'
_chemical_formula_weight         207.23
_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                   10.2718(2)
_cell_length_b                   9.7571(3)
_cell_length_c                   10.9209(3)
_cell_measurement_reflns_used    10624
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.3210
_cell_measurement_theta_min      4.5260
_cell_volume                     1094.53(5)
_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 1.000
_diffrn_measured_fraction_theta_max 0.984
_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     32.00 118.00   0.50    0.17    --   46.45  57.00-150.00  172
  2  \w     24.00 118.00   0.50    0.17    --   46.45  77.00-150.00  188
  3  \w     24.00 118.00   0.50    0.17    --   46.45  77.00-120.00  188
  4  \w     24.00 118.00   0.50    0.17    --   46.45  77.00 -90.00  188
  5  \w     34.00 121.00   0.50    0.17    --   46.45  22.00 151.00  174
  6  \w     93.00 178.00   0.50    0.67    --  104.75  22.00 151.00  170
  7  \w     33.00  73.00   0.50    0.67    --  104.75 -61.00  90.00   80
  8  \w     33.00  71.00   0.50    0.67    --  104.75 -61.00  60.00   76
  9  \w     34.00  73.00   0.50    0.67    --  104.75 -61.00 -30.00   78
 10  \w    -28.00  31.00   0.50    0.17    --   46.45 -22.00 -14.00  118
 11  \w    -40.00  27.00   0.50    0.17    --  -46.45  37.00 -90.00  134
 12  \w    -24.00  29.00   0.50    0.17    --  -46.45  19.00 -90.00  106
 13  \w    -56.00 -31.00   0.50    0.67    -- -102.00  77.00 -90.00   50
 14  \w    -54.00 -29.00   0.50    0.67    -- -102.00  77.00-120.00   50
 15  \w    -97.00 -71.00   0.50    0.67    -- -102.00  77.00 -90.00   52
 16  \w   -101.00 -76.00   0.50    0.67    -- -102.00  77.00-120.00   50
 17  \w    -63.00 -37.00   0.50    0.67    -- -102.00  61.00 -90.00   52
 18  \w    -68.00 -34.00   0.50    0.67    -- -102.00  61.00-120.00   68
 19  \w    -69.00 -29.00   0.50    0.67    -- -102.00  61.00   0.00   80
 20  \w    -66.00 -40.00   0.50    0.67    -- -102.00  61.00 -30.00   52
 21  \w    -63.00 -30.00   0.50    0.67    -- -102.00  61.00  60.00   66
 22  \w    -68.00 -30.00   0.50    0.67    -- -102.00  61.00  90.00   76
 23  \w    -26.00  29.00   0.50    0.17    --  -46.45  22.00 151.00  110
 24  \w   -121.00 -34.00   0.50    0.17    --  -46.45 -22.00 -14.00  174
 25  \w   -156.00 -78.00   0.50    0.67    -- -102.00 -79.00-126.59  156
 26  \w   -175.00 -79.00   0.50    0.67    -- -102.00 -77.00 -30.00  192
 27  \w   -109.00 -82.00   0.50    0.67    -- -102.00 -77.00 -37.78   54
 28  \w   -108.00 -79.00   0.50    0.67    -- -102.00 -77.00 -90.00   58
 29  \w   -105.00 -79.00   0.50    0.67    -- -102.00 -77.00 -60.00   52
 30  \w   -120.00 -34.00   0.50    0.17    --  -46.45 -37.00 -60.00  172
 31  \w   -105.00 -79.00   0.50    0.67    -- -102.00 -77.00-150.00   52
 32  \w   -105.00 -79.00   0.50    0.67    -- -102.00 -77.00-120.00   52
 33  \w   -114.00 -82.00   0.50    0.67    -- -102.00 -75.00 -45.71   64
 34  \w   -108.00 -81.00   0.50    0.67    -- -102.00 -73.00 -36.53   54
 35  \w   -108.00 -81.00   0.50    0.67    -- -102.00 -73.00 -69.06   54
 36  \w   -109.00 -82.00   0.50    0.67    -- -102.00 -72.00-159.70   54
 37  \w   -115.00 -87.00   0.50    0.67    -- -102.00 -65.00-106.98   56
 38  \w   -171.00 -87.00   0.50    0.67    -- -102.00 -65.00-121.33  168
 39  \w   -174.00-149.00   0.50    0.67    -- -102.00 -77.00 -90.00   50
 40  \w   -161.00-135.00   0.50    0.67    -- -102.00 -73.00 -36.53   52
 41  \w   -173.00 -85.00   0.50    0.67    -- -102.00 -61.00 -60.00  176
 42  \w   -171.00 -87.00   0.50    0.67    -- -102.00 -57.00 -98.08  168
 43  \w   -172.00 -88.00   0.50    0.67    -- -102.00 -52.00 -78.99  168
 44  \w   -160.00 -89.00   0.50    0.67    -- -102.00 -54.00-163.08  142
 45  \w   -172.00 -85.00   0.50    0.67    -- -102.00 -61.00-180.00  174
 46  \w   -129.00 -90.00   0.50    0.67    -- -102.00 -45.00-180.00   78
 47  \w   -114.00 -86.00   0.50    0.67    -- -102.00 -61.00-120.00   56
 48  \w   -117.00 -29.00   0.50    0.67    -- -102.00 125.00-120.00  176
 49  \w   -175.00 -90.00   0.50    0.67    -- -102.00 -22.00 -14.00  170
 50  \w   -164.00-138.00   0.50    0.67    -- -102.00 -89.00 -66.28   52
 51  \w   -175.00 -77.00   0.50    0.67    -- -102.00 -89.00 -91.78  196
 52  \w   -111.00 -77.00   0.50    0.67    -- -102.00 -89.00 -66.28   68
 53  \w   -118.00 -71.00   0.50    0.17    --  -46.45-125.00  90.00   94
;
_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      0.1221313000
_diffrn_orient_matrix_UB_12      0.0898475000
_diffrn_orient_matrix_UB_13      0.0154174000
_diffrn_orient_matrix_UB_21      0.0790869000
_diffrn_orient_matrix_UB_22      -0.1272893000
_diffrn_orient_matrix_UB_23      0.0382983000
_diffrn_orient_matrix_UB_31      0.0362169000
_diffrn_orient_matrix_UB_32      -0.0261611000
_diffrn_orient_matrix_UB_33      -0.1348372000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_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       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18887
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.008
_diffrn_reflns_theta_min         4.532
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31770
_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    0.261
_exptl_crystal_description       plate
_exptl_crystal_F_000             88
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 942 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2179
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0600P)^2^+0.1928P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.0984
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                2131
_reflns_number_total             2179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06529g2.cif
_cod_data_source_block           20210427d
_cod_depositor_comments
;

2024-06-28
Formula fixed to be consistent with given Z
                 miguel
;
_cod_original_formula_sum            'C H N O'
_cod_original_formula_weight         43.03
_cod_database_code               7129531
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C1H1N1O1
_diffrn_oxdiff_digest_frames
;
01eccb6b3140cc15faf243c1d19d63eaab00078d00f
;
_diffrn_oxdiff_digest_hkl
;
01d84402e0a0cef16bd29162d31a5060fe4d62
;
_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)
1.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5), C3(H3), C4(H4)
1.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              2812
_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 1.613
_oxdiff_exptl_absorpt_empirical_full_min 0.390