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_7135496
_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         'C14 H12 Br N O3'
_chemical_formula_sum            'C14 H12 Br N O3'
_chemical_formula_weight         322.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-06-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-06-30 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.502(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2247(8)
_cell_length_b                   7.7018(6)
_cell_length_c                   15.9626(11)
_cell_measurement_reflns_used    2591
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.3190
_cell_measurement_theta_min      2.0890
_cell_volume                     1368.16(17)
_computing_cell_refinement       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.797
_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    -79.00   8.00   0.50    2.68    --   -4.75 -19.00  30.00  174
  2  \w    -23.00   9.00   0.50    2.68    --   -4.75 -99.00 -60.00   64
  3  \w    -12.00  17.00   0.50    2.68    --   -4.75 -99.00-150.00   58
  4  \w    -10.00  49.00   0.50    2.68    --   -4.75  19.00-120.00  118
;
_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      -0.0502355000
_diffrn_orient_matrix_UB_12      0.0486936000
_diffrn_orient_matrix_UB_13      0.0093936000
_diffrn_orient_matrix_UB_21      -0.0242334000
_diffrn_orient_matrix_UB_22      -0.0756755000
_diffrn_orient_matrix_UB_23      0.0166517000
_diffrn_orient_matrix_UB_31      0.0308383000
_diffrn_orient_matrix_UB_32      0.0197585000
_diffrn_orient_matrix_UB_33      0.0405232000
_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  0.0442
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.797
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8499
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.797
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.873
_diffrn_reflns_theta_min         2.095
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.007
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.106a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0506
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0256P)^2^+1.3381P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2346
_reflns_number_total             3442
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04935k2.cif
_cod_data_source_block           smt-me_auto
_cod_database_code               7135496
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C  H N O'
_chemical_oxdiff_usercomment     30-06-2025
_reflns_odcompleteness_completeness 98.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C00F(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C007(H007), C00D(H00D), C00E(H00E)
2.c Idealised Me refined as rotating group:
 C00I(H00C,H00F,H00G), C00J(H00H,H00I,H00J)
;
_shelx_res_checksum              64152
_olex2_submission_original_sample_id SMT-Me
_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 1.768
_oxdiff_exptl_absorpt_empirical_full_min 0.587