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_7135494
_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         'C19 H15 N O3'
_chemical_formula_sum            'C19 H15 N O3'
_chemical_formula_weight         305.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-04
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-03-05 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.5147(16)
_cell_length_b                   5.6766(5)
_cell_length_c                   24.744(2)
_cell_measurement_reflns_used    2644
_cell_measurement_temperature    158(11)
_cell_measurement_theta_max      27.5770
_cell_measurement_theta_min      2.0520
_cell_volume                     3022.0(4)
_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_environment      N~2~
_diffrn_ambient_temperature      158(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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     -5.00  79.00   0.50    3.50    --    6.31  57.00  30.00  168
  2  \w     51.00  78.00   0.50    3.50    --    6.31  30.00 140.00   54
  3  \w      8.00  37.00   0.50    3.50    --    6.31  30.00 140.00   58
  4  \w    -23.00  11.00   0.50    3.50    --   -5.22 -99.00 -60.00   68
;
_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      0.0248035000
_diffrn_orient_matrix_UB_12      0.0300391000
_diffrn_orient_matrix_UB_13      -0.0103580000
_diffrn_orient_matrix_UB_21      0.0420222000
_diffrn_orient_matrix_UB_22      -0.0135088000
_diffrn_orient_matrix_UB_23      -0.0243085000
_diffrn_orient_matrix_UB_31      -0.1150265000
_diffrn_orient_matrix_UB_32      0.0015496000
_diffrn_orient_matrix_UB_33      -0.0111043000
_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  0.1103
_diffrn_reflns_av_unetI/netI     0.1105
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15576
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.893
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53346
_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    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1069 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5574
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0629
_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^)+(0.0556P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1573
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.848
_reflns_Friedel_fraction_max     0.803
_reflns_number_gt                3552
_reflns_number_total             5574
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04935k2.cif
_cod_data_source_block           smt-618m
_cod_original_cell_volume        3022.0(5)
_cod_database_code               7135494
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C H N O '
_chemical_oxdiff_usercomment     24-02-2025
_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:
 C00L(H00A,H00B), C00R(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00N(H00N), C00O(H00O), C00Q(H00Q), C00T(H00T), C00U(H00U),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C011(H011),
 C012(H012), C014(H014), C015(H015), C016(H016), C017(H017), C018(H018),
 C019(H019), C01A(H01G)
2.c Idealised Me refined as rotating group:
 C010(H01D,H01E,H01F), C013(H01A,H01B,H01C)
;
_shelx_res_checksum              73856
_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 1.669
_oxdiff_exptl_absorpt_empirical_full_min 0.760