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_7129530
_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         'C8 H5 O3, C9 H20 N'
_chemical_formula_sum            'C18 H25 N0.25 O3'
_chemical_formula_weight         292.88
_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             2021-09-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-11 deposited with the CCDC.	2022-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.266(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3396(5)
_cell_length_b                   10.1521(4)
_cell_length_c                   15.1640(8)
_cell_measurement_reflns_used    8653
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.1310
_cell_measurement_theta_min      4.2520
_cell_volume                     1591.73(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_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 0.986
_diffrn_measured_fraction_theta_max 0.952
_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    0.06    --   46.95  57.00 120.00  172
  2  \w     32.00 118.00   0.50    0.06    --   46.95  57.00-150.00  172
  3  \w     92.00 177.00   0.50    0.24    --  104.75  42.00-111.00  170
  4  \w     91.00 116.00   0.50    0.24    --  104.75  15.00-180.00   50
  5  \w     32.00  73.00   0.50    0.24    --  104.75 -61.00 -60.00   82
  6  \w     32.00 129.00   0.50    0.24    --  104.75 -79.00 -74.00  194
  7  \w     32.00 108.00   0.50    0.24    --  104.75 -77.00  60.00  152
  8  \w     32.00  73.00   0.50    0.24    --  104.75 -61.00 150.00   82
  9  \w    -25.00  71.00   0.50    0.06    --   46.95 -79.00 -74.00  192
 10  \w     32.00  73.00   0.50    0.24    --  104.75 -61.00-150.00   82
 11  \w     32.00 109.00   0.50    0.24    --  104.75 -94.00-150.00  154
 12  \w     32.00 109.00   0.50    0.24    --  104.75 -94.00 -90.00  154
 13  \w     32.00 109.00   0.50    0.24    --  104.75 -94.00  60.00  154
 14  \w    -24.00  29.00   0.50    0.06    --  -46.95  19.00 -30.00  106
 15  \w    -69.00 -29.00   0.50    0.24    -- -102.00  61.00   0.00   80
 16  \w    -69.00 -29.00   0.50    0.24    -- -102.00  61.00 150.00   80
 17  \w   -119.00 -24.00   0.50    0.06    --  -46.95 -77.00  30.00  190
 18  \w   -119.00 -24.00   0.50    0.06    --  -46.95 -77.00 -90.00  190
 19  \w   -175.00 -69.00   0.50    0.24    -- -102.00-129.00  42.00  212
 20  \w   -119.00 -71.00   0.50    0.06    --  -46.95-125.00  90.00   96
 21  \w   -119.00 -69.00   0.50    0.06    --  -46.95-129.00  42.00  100
;
_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      0.0285879000
_diffrn_orient_matrix_UB_12      -0.0796542000
_diffrn_orient_matrix_UB_13      -0.0843931000
_diffrn_orient_matrix_UB_21      0.1459440000
_diffrn_orient_matrix_UB_22      0.0097326000
_diffrn_orient_matrix_UB_23      0.0194691000
_diffrn_orient_matrix_UB_31      -0.0062973000
_diffrn_orient_matrix_UB_32      -0.1288639000
_diffrn_orient_matrix_UB_33      0.0532154000
_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  0.0642
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14153
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.684
_diffrn_reflns_theta_min         4.276
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       plate
_exptl_crystal_F_000             635
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.040
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.257
_refine_ls_extinction_coef       0.09(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   3.359
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      3.359
_refine_ls_R_factor_all          0.2269
_refine_ls_R_factor_gt           0.2227
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.6254
_refine_ls_wR_factor_ref         0.6288
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2872
_reflns_number_total             3188
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06529g2.cif
_cod_data_source_block           20210911a_auto
_cod_database_code               7129530
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C1H1N1O1
_reflns_odcompleteness_completeness 98.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N17(H17A,H17B), C15(H15A,H15B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C19(H19A,H19B,
 H19C)
;
_shelx_res_checksum              29511
_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 1.716
_oxdiff_exptl_absorpt_empirical_full_min 0.510