Photoredox-catalyzed Giese reaction for the synthesis of γ-nitro alcohols.
He, Ai-Jie; Jiang, Wen-Jie; Zhang, Yan-Ping; Yang, Lei; Zhao, Jian-Qiang; Wang, Zhen-Hua; Yuan, Wei-Cheng; You, Yong; Organic & biomolecular chemistry 24 (2026) 1042–1047; doi:10.1039/d5ob01840d

data_7160975
_publ_section_title
;
 Photoredox-catalyzed Giese reaction for the synthesis of &#x3b3;-nitro
 alcohols.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1042
_journal_page_last               1047
_journal_paper_doi               10.1039/d5ob01840d
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C15 H15 N O3'
_chemical_formula_sum            'C15 H15 N O3'
_chemical_formula_weight         257.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-06-19
_audit_creation_method
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_audit_update_record
;
2025-09-28 deposited with the CCDC.	2026-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.246(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6525(6)
_cell_length_b                   5.5652(5)
_cell_length_c                   15.5161(11)
_cell_measurement_reflns_used    2123
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.0330
_cell_measurement_theta_min      5.6490
_cell_volume                     660.79(9)
_computing_cell_refinement       'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 42.102a (release 15-09-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_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    -92.00 -30.00   1.00    1.10    --  -33.50 -57.00-120.00   62
  2  \w    -62.00 -37.00   1.00    1.10    --  -33.50 178.00 150.00   25
  3  \w     65.00  99.00   1.00    1.10    --   36.47 178.00 150.00   34
  4  \w     65.00  90.00   1.00    1.10    --   36.47-129.00 123.00   25
  5  \w     72.00 104.00   1.00    1.10    --   36.47  37.00  30.00   32
  6  \w     23.00  62.00   1.00    1.10    --   36.47  37.00  30.00   39
  7  \w     41.00  92.00   1.00   12.50    --  108.00-111.00  90.00   51
  8  \w    106.00 166.00   1.00   12.50    --  108.00 111.00  60.00   60
  9  \w    108.00 133.00   1.00   12.50    --  108.00 111.00  30.00   25
 10  \w     83.00 144.00   1.00   12.50    --  108.00  30.00  90.00   61
 11  \w    112.00 177.00   1.00   12.50    --  108.00  30.00 -60.00   65
 12  \w     84.00 140.00   1.00   12.50    --  108.00 178.00 -90.00   56
 13  \w    -60.00 -35.00   1.00    4.00    --  -33.50 178.00-120.00   25
 14  \w      5.00  31.00   1.00    4.00    --   36.47 -99.00-150.00   26
 15  \w     32.00  58.00   1.00    4.00    --   36.47 -37.00  90.00   26
 16  \w     43.00  75.00   1.00    4.00    --   36.47 -99.00-150.00   32
 17  \w    -33.00  17.00   1.00    4.00    --   36.47 -37.00  90.00   50
 18  \w     39.00  91.00   1.00   17.50    --  108.00 -94.00  90.00   52
 19  \w     99.00 173.00   1.00   17.50    --  108.00  45.00   0.00   74
 20  \w     57.00  90.00   1.00   17.50    --  108.00 -45.00  60.00   33
 21  \w    134.00 162.00   1.00   17.50    --  108.00  77.00-180.00   28
 22  \w   -102.00 -39.00   1.00    4.00    --  -33.50 -57.00 120.00   63
 23  \w    -91.00 -45.00   1.00    4.00    --  -33.50 178.00 -90.00   46
 24  \w      0.00  25.00   1.00    4.00    --   36.47  91.00  72.65   25
 25  \w      0.00  25.00   1.00    4.00    --   36.47  92.00 150.98   25
 26  \w     -2.00  23.00   1.00    4.00    --   36.47  95.00 168.12   25
 27  \w      0.00  25.00   1.00    4.00    --   36.47  95.00-158.38   25
 28  \w    -18.00   8.00   1.00    4.00    --   36.47 -77.00  90.00   26
 29  \w      4.00  29.00   1.00    4.00    --   36.47  85.00  33.11   25
 30  \w      4.00  35.00   1.00    4.00    --   36.47  19.00 150.00   31
 31  \w     29.00  55.00   1.00    4.00    --   36.47  57.00-180.00   26
 32  \w     72.00  98.00   1.00    4.00    --   36.47  57.00  60.00   26
 33  \w     61.00  97.00   1.00    4.00    --   36.47  57.00-180.00   36
 34  \w     47.00  73.00   1.00    4.00    --   36.47  19.00 150.00   26
 35  \w     88.00 114.00   1.00   17.50    --  108.00  61.00 120.00   26
 36  \w     90.00 116.00   1.00   17.50    --  108.00  61.00  60.00   26
 37  \w     88.00 114.00   1.00   17.50    --  108.00  45.00  60.00   26
 38  \w     89.00 115.00   1.00   17.50    --  108.00  61.00   0.00   26
 39  \w     89.00 115.00   1.00   17.50    --  108.00  61.00  90.00   26
 40  \w     39.00  64.00   1.00   17.50    --  108.00 -94.00 -90.00   25
 41  \w     89.00 115.00   1.00   17.50    --  108.00  30.00 150.00   26
 42  \w     84.00 110.00   1.00   17.50    --  108.00  30.00  60.00   26
 43  \w     89.00 115.00   1.00   17.50    --  108.00  45.00 120.00   26
 44  \w     90.00 116.00   1.00   17.50    --  108.00  45.00  30.00   26
 45  \w    144.00 170.00   1.00   17.50    --  108.00  61.00  30.00   26
 46  \w    129.00 155.00   1.00   17.50    --  108.00  61.00 150.00   26
 47  \w     88.00 114.00   1.00   17.50    --  108.00  61.00 150.00   26
 48  \w     88.00 114.00   1.00   17.50    --  108.00  30.00-180.00   26
 49  \w     89.00 115.00   1.00   17.50    --  108.00  45.00  90.00   26
 50  \w     90.00 116.00   1.00   17.50    --  108.00  45.00 150.00   26
 51  \w     85.00 111.00   1.00   17.50    --  108.00  30.00  30.00   26
 52  \w    148.00 173.00   1.00   17.50    --  108.00  61.00 120.00   25
 53  \w     93.00 119.00   1.00   17.50    --  108.00  30.00 120.00   26
 54  \w     97.00 123.00   1.00   17.50    --  108.00  61.00  30.00   26
 55  \w     14.00  39.00   1.00    4.00    --  -33.50  19.00 -90.00   25
 56  \w     60.00  87.00   1.00   17.50    --  108.00-111.00 -60.00   27
 57  \w    114.00 155.00   1.00   17.50    --  108.00 111.00   0.00   41
 58  \w     41.00  72.00   1.00   17.50    --  108.00 -94.00  60.00   31
 59  \w    130.00 176.00   1.00   17.50    --  108.00  30.00 -90.00   46
 60  \w    103.00 129.00   1.00   17.50    --  108.00  77.00 -60.00   26
 61  \w     88.00 114.00   1.00   17.50    --  108.00  61.00  30.00   26
 62  \w    148.00 176.00   1.00   17.50    --  108.00 111.00 -90.00   28
 63  \w     43.00  69.00   1.00   17.50    --  108.00 -61.00   0.00   26
 64  \w     93.00 119.00   1.00   17.50    --  108.00 -61.00   0.00   26
 65  \w     71.00  97.00   1.00   17.50    --  108.00 -45.00-150.00   26
 66  \w    120.00 146.00   1.00   17.50    --  108.00 111.00-180.00   26
 67  \w     38.00  66.00   1.00   17.50    --  108.00 -30.00  90.00   28
 68  \w     73.00  99.00   1.00   17.50    --  108.00 -30.00  90.00   26
 69  \w     76.00 108.00   1.00   17.50    --  108.00 -77.00  60.00   32
 70  \w    108.00 134.00   1.00   17.50    --  108.00 111.00 -60.00   26
 71  \w    131.00 170.00   1.00   17.50    --  108.00  77.00 150.00   39
 72  \w     75.00 106.00   1.00   17.50    --  108.00  15.00  90.00   31
 73  \w     38.00  63.00   1.00   17.50    --  108.00 -45.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0704340000
_diffrn_orient_matrix_UB_12      0.0101685000
_diffrn_orient_matrix_UB_13      -0.0930897000
_diffrn_orient_matrix_UB_21      -0.1840651000
_diffrn_orient_matrix_UB_22      0.0567749000
_diffrn_orient_matrix_UB_23      0.0343711000
_diffrn_orient_matrix_UB_31      0.0412030000
_diffrn_orient_matrix_UB_32      0.2707113000
_diffrn_orient_matrix_UB_33      -0.0036746000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6931
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.093
_diffrn_reflns_theta_min         5.703
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.142a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 552 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2249
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0578
_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^)+(0.0981P)^2^+0.0541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1659
_refine_ls_wR_factor_ref         0.1814
_reflns_Friedel_coverage         0.596
_reflns_Friedel_fraction_full    0.753
_reflns_Friedel_fraction_max     0.735
_reflns_number_gt                1802
_reflns_number_total             2249
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01840d2.cif
_cod_data_source_block           202506180
_cod_database_code               7160975
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C21H17N3O4
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.878
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.793(4)
 0.207(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
3. Restrained distances
 N1A-O2A
 1.2 with sigma of 0.02
 N1A-O3A
 1.2 with sigma of 0.02
 N1A-C15 \\sim N1-C15
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(N1) \\sim Ueq, Uanis(N1A) \\sim Ueq, Uanis(O3A) \\sim Ueq, Uanis(O3)
\\sim Ueq, Uanis(O2A) \\sim Ueq, Uanis(O2) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(O3) = Uanis(O3A)
Uanis(O2) = Uanis(O2A)
Uanis(N1) = Uanis(N1A)
5. Others
 Sof(H15C)=Sof(H15D)=Sof(O3A)=Sof(O2A)=Sof(N1A)=1-FVAR(1)
 Sof(O2)=Sof(O3)=Sof(N1)=Sof(H15A)=Sof(H15B)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C13(H13)
6.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C15(H15C,H15D)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12)
6.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              16675
_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 1.277
_oxdiff_exptl_absorpt_empirical_full_min 0.818