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_7129528
_publ_section_title
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 Synthesis of \b-Nitro Ketone from Geminal Bromonitroalkane and Silyl Enol
 Ether by Visible Light Photoredox Catalysis
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_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06529G
_journal_year                    2022
_chemical_formula_moiety         'C13 H15 N O3'
_chemical_formula_sum            'C13 H15 N O3'
_chemical_formula_weight         233.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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
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2021-09-07 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            8
_cell_length_a                   10.15647(11)
_cell_length_b                   11.03134(15)
_cell_length_c                   20.7789(3)
_cell_measurement_reflns_used    13501
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7370
_cell_measurement_theta_min      4.2400
_cell_volume                     2328.06(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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    shelxt
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20591
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.142
_diffrn_reflns_theta_min         4.255
_diffrn_source                   'Rigaku (Cu) X-ray Source'
_diffrn_source_type              'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85480
_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    1.331
_exptl_crystal_description       plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.00071(15)
_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   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2397
_refine_ls_number_restraints     124
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0456P)^2^+1.0604P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1084
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2197
_reflns_number_total             2397
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06529g2.cif
_cod_data_source_block           20210624b
_cod_original_cell_volume        2328.05(5)
_cod_database_code               7129528
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Restrained distances
 C10-C11 \\sim C10-C11A
 with sigma of 0.02
 C11-C12 \\sim C11A-C12A
 with sigma of 0.02
 C14-C13 \\sim C14-C13A
 with sigma of 0.02
 C13-C12 \\sim C13A-C12A
 with sigma of 0.02
 C13A-C12A \\sim C13-C12
 with sigma of 0.02
 C10-C12 \\sim C10-C12A
 with sigma of 0.04
 C11-C10 \\sim C11A-C10
 with sigma of 0.02
 C14-C12 \\sim C14-C12A
 with sigma of 0.04
 C12A-C11A \\sim C12-C11
 with sigma of 0.02
 C11-C13 \\sim C11A-C13A
 with sigma of 0.04
2. Rigid bond restraints
 N15, O17, O16
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C11 \\sim C11A \\sim C12A \\sim C12 \\sim C13 \\sim C13A: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
Uanis(C13A) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O17) \\sim Ueq, Uanis(N15) \\sim Ueq, Uanis(O16) \\sim Ueq, Uanis(C5)
\\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C2) \\sim Ueq: with
sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(H14C)=Sof(H14D)=Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(H12C)=
 Sof(H12D)=Sof(C13A)=Sof(H13C)=Sof(H13D)=1-FVAR(1)
 Sof(H14A)=Sof(H14B)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C13)=Sof(H13A)=Sof(H13B)=
 Sof(C12)=Sof(H12A)=Sof(H12B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C14(H14C,H14D), C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B),
 C12(H12A,H12B), C11A(H11C,H11D), C12A(H12C,H12D), C13A(H13C,H13D)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C2(H2), C4(H4), C3(H3)
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_shelx_res_checksum              92331
_olex2_submission_special_instructions 'No special instructions were received'