Transition-metal free, radical oxidation of 1,6-enyne cyclopropanation: synthesis of aza-bicyclo[4.1.0]heptane derivatives.
Meena, Shivam A.; Thakur, Deepika; Nandy, Abhijit; Ranjan, Rahul; Rai, Anubhav; Banerjee, Shibdas; Verma, Akhilesh K.; Chemical communications (Cambridge, England) 60 (2024) 9230–9233; doi:10.1039/d4cc02639j

data_7133436
_publ_section_title
;
 Transition-metal free, radical oxidation of 1,6-enyne cyclopropanation:
 synthesis of aza-bicyclo[4.1.0]heptane derivatives.
;
_journal_issue                   69
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9230
_journal_page_last               9233
_journal_paper_doi               10.1039/d4cc02639j
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C21 H17 N O4'
_chemical_formula_sum            'C21 H17 N O4'
_chemical_formula_weight         347.36
_chemical_name_systematic        SMT-366
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-12-02 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.036(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2969(17)
_cell_length_b                   6.8015(6)
_cell_length_c                   18.834(2)
_cell_measurement_reflns_used    4176
_cell_measurement_temperature    224(40)
_cell_measurement_theta_max      27.7640
_cell_measurement_theta_min      3.2550
_cell_volume                     1697.6(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      224(40)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.721
_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    -18.00  33.00   0.50    1.60    --   -5.21  16.00 104.00  102
  2  \w     -9.00  21.00   0.50    1.60    --    5.37 -77.00  90.00   60
  3  \w    -58.00 -24.00   0.50    1.60    --    5.37 -77.00  90.00   68
  4  \w    -23.00  21.00   0.50    1.60    --   -5.21 -99.00 -30.00   88
  5  \w     -7.00  26.00   0.50    1.60    --   -5.21 -99.00 -60.00   66
;
_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      -0.0520922000
_diffrn_orient_matrix_UB_12      0.0209084000
_diffrn_orient_matrix_UB_13      -0.0104430000
_diffrn_orient_matrix_UB_21      -0.0055450000
_diffrn_orient_matrix_UB_22      0.0077910000
_diffrn_orient_matrix_UB_23      -0.0389298000
_diffrn_orient_matrix_UB_31      -0.0111235000
_diffrn_orient_matrix_UB_32      -0.1018721000
_diffrn_orient_matrix_UB_33      -0.0051310000
_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  0.0569
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.721
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10835
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.721
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.919
_diffrn_reflns_theta_min         3.214
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0543
_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^)+(0.0477P)^2^+0.2903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1469
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2494
_reflns_number_total             3870
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02639j2.cif
_cod_data_source_block           smt-366_auto
_cod_depositor_comments
'Adding full bibliography for 7133436--7133438.cif.'
_cod_database_code               7133436
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     01-12-2023
_reflns_odcompleteness_completeness 94.43
_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:
 C00L(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00I), C00J(H00J),
 C00K(H00K), C00M(H00M), C00O(H00O)
2.c Idealised Me refined as rotating group:
 C00P(H00C,H00H,H00L), C00Q(H00N,H00P,H00Q)
;
_shelx_res_checksum              39076
_shelx_hkl_checksum              3887
_olex2_submission_original_sample_id SMT-366
_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 1.145
_oxdiff_exptl_absorpt_empirical_full_min 0.882