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_7160859
_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
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_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
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_audit_update_record
;
2025-09-02 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
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_cell_measurement_theta_min      5.19
_cell_volume                     1268.83(8)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
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_diffrn_reflns_limit_k_min       -21
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_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13522
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         78.200
_diffrn_reflns_theta_min         5.193
_diffrn_source                   'I-mu-S microfocus sealed tube'
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_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS 2016/2: 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    1.331
_exptl_crystal_description       block
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_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
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_refine_diff_density_max         0.171
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
; 
 Flack x determined using 1185 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.14(6)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_R_factor_all          0.0304
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_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^)+(0.0523P)^2^+0.1772P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0802
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                2618
_reflns_number_total             2650
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01564b2.cif
_cod_data_source_block           ic22289
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               7160859
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.839
_shelx_estimated_absorpt_t_max   0.899
_shelx_res_checksum              78465