Photocatalytic oxidative cyclopropanation of aza-1,6-enynes: construction of 3-aza-bicyclo[3.1.0]hexane derivatives.
Meena, Shivam A.; Thakur, Deepika; Tripathi, Surya P.; Ranjan, Rahul; Verma, Akhilesh K.; Chemical communications (Cambridge, England) 62 (2026) 2641–2645; doi:10.1039/d5cc04935k

data_7135497
_publ_section_title
;
 Photocatalytic oxidative cyclopropanation of aza-1,6-enynes: construction
 of 3-aza-bicyclo[3.1.0]hexane derivatives.
;
_journal_issue                   8
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2641
_journal_page_last               2645
_journal_paper_doi               10.1039/d5cc04935k
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C25 H19 N O3 S'
_chemical_formula_sum            'C25 H19 N O3 S'
_chemical_formula_weight         413.47
_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             2025-06-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-06-10 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 138.05(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.481(5)
_cell_length_b                   6.8544(3)
_cell_length_c                   15.489(3)
_cell_measurement_reflns_used    5795
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5720
_cell_measurement_theta_min      2.0460
_cell_volume                     2092.3(17)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    -77.00   5.00   0.50    3.00    --   -5.22 -43.00  29.00  164
  2  \w    -23.00  11.00   0.50    3.00    --   -5.22 -99.00 -30.00   68
  3  \w    -23.00   2.00   0.50    3.00    --   -5.22 -99.00 -60.00   50
  4  \w    -19.00  67.00   0.50    3.00    --   -5.22  43.00-178.00  172
  5  \w     43.00  69.00   0.50    3.00    --    6.31  43.00-178.00   52
  6  \w     14.00  39.00   0.50    3.00    --    6.31  43.00-178.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0331938000
_diffrn_orient_matrix_UB_12      -0.0137061000
_diffrn_orient_matrix_UB_13      0.0337990000
_diffrn_orient_matrix_UB_21      -0.0488276000
_diffrn_orient_matrix_UB_22      0.0530831000
_diffrn_orient_matrix_UB_23      -0.0075835000
_diffrn_orient_matrix_UB_31      -0.0346865000
_diffrn_orient_matrix_UB_32      -0.0877900000
_diffrn_orient_matrix_UB_33      -0.0098407000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17563
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.067
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_refine_diff_density_max         1.738
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.297
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4266
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.297
_refine_ls_R_factor_all          0.1557
_refine_ls_R_factor_gt           0.1225
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3044
_refine_ls_wR_factor_ref         0.3454
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2783
_reflns_number_total             4266
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04935k2.cif
_cod_data_source_block           smt-788p-r_auto
_cod_original_cell_volume        2092.4(11)
_cod_database_code               7135497
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     09-06-2025
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00M(H00B,H00C)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J),
 C00L(H00L), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U)
2.c Idealised Me refined as rotating group:
 C00N(H00D,H00E,H00G)
;
_shelx_res_checksum              39805
_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 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.693