A one-pot visible-light strategy for cyclobutanone synthesis <i>via</i> sequential [2 + 2] cycloaddition and Nef reaction of nitroalkenes and 2-vinylpyridines.
Chen, Yong-Shun; Indurmuddam, Ranadheer Reddy; Hong, Bor-Cherng; Chien, Su-Ying; Organic & biomolecular chemistry  (2025) –; doi:10.1039/d5ob01564b

data_7160860
_publ_section_title
;
 A one-pot visible-light strategy for cyclobutanone synthesis <i>via</i>
 sequential [2 + 2] cycloaddition and Nef reaction of nitroalkenes and
 2-vinylpyridines.
;
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_paper_doi               10.1039/d5ob01564b
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-09-02 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1448(2)
_cell_length_b                   17.0816(5)
_cell_length_c                   9.2698(3)
_cell_measurement_reflns_used    9044
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      70.09
_cell_measurement_theta_min      5.43
_cell_volume                     1289.67(6)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.16'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1503)'
_computing_publication_material  'Bruker APEX5 v2023.9-4'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Bruker D8 VENTURE (PHOTON III C14 COMS-10cmx14cm)'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11637
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.969
_diffrn_reflns_theta_min         5.429
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_correction_T_min  0.8588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.083
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
; 
 Flack x determined using 979 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2304
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0263
_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^)+(0.0474P)^2^+0.1052P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0722
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_full    0.890
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                2271
_reflns_number_total             2304
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01564b2.cif
_cod_data_source_block           ic23227
_cod_database_code               7160860
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.855
_shelx_estimated_absorpt_t_max   0.927
_shelx_res_checksum              7075