Ring expansion/opening reactions of epoxy ene-amides: access to azabicyclononene, tetrahydropyridine and tetrazole scaffolds
Suraj,; Swamy, K. C. Kumara; New Journal of Chemistry 47 (2023) 9061–9065; doi:10.1039/D3NJ00529A

data_7062416
_publ_section_title
;
 Ring expansion/opening reactions of epoxy ene-amides: access to
 azabicyclononene, tetrahydropyridine and tetrazole scaffolds
;
_journal_issue                   19
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9061
_journal_page_last               9065
_journal_paper_doi               10.1039/D3NJ00529A
_journal_volume                  47
_journal_year                    2023
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C24 H21 N O4 S'
_chemical_formula_sum            'C24 H21 N O4 S'
_chemical_formula_weight         419.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-07
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2023-01-20 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9615(2)
_cell_length_b                   14.5594(7)
_cell_length_c                   23.8714(11)
_cell_measurement_reflns_used    4150
_cell_measurement_temperature    297.4(5)
_cell_measurement_theta_max      25.9990
_cell_measurement_theta_min      2.1990
_cell_volume                     2071.94(15)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.4(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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    -31.00  -5.00   0.50   18.00    --  -15.60  -3.00 -16.00   52
  2  \w     -8.00  43.00   0.50   18.00    --   16.22 -61.00   0.00  102
  3  \w    -52.00 -20.00   0.50   18.00    --   16.22 -61.00   0.00   64
  4  \w   -100.00 -39.00   0.50   18.00    --  -15.60  -3.00 -16.00  122
  5  \w    -71.00 -35.00   0.50   18.00    --  -15.60 129.00 -68.00   72
  6  \w    -46.00 -18.00   0.50   18.00    --  -15.60 135.00  18.00   56
  7  \w     20.00  45.00   0.50   18.00    --  -15.60  45.00 150.00   50
  8  \w    -36.00  -1.00   0.50   18.00    --  -15.60  45.00 150.00   70
  9  \w    -86.00   2.00   0.50   18.00    --  -15.60 -45.00  90.00  176
 10  \w    -16.00  16.00   0.50   18.00    --  -15.60 -94.00-120.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0015261000
_diffrn_orient_matrix_UB_12      -0.0122594000
_diffrn_orient_matrix_UB_13      -0.0287502000
_diffrn_orient_matrix_UB_21      0.0045065000
_diffrn_orient_matrix_UB_22      -0.0471224000
_diffrn_orient_matrix_UB_23      0.0074662000
_diffrn_orient_matrix_UB_31      -0.1188959000
_diffrn_orient_matrix_UB_32      -0.0019270000
_diffrn_orient_matrix_UB_33      -0.0000817000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2136
_diffrn_reflns_av_unetI/netI     0.1538
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8679
_diffrn_reflns_point_group_measured_fraction_full 0.925
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.206
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details
;
 Flack x determined using 463 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.32(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1321
_refine_ls_R_factor_gt           0.0952
_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^)+(0.1712P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2346
_refine_ls_wR_factor_ref         0.2916
_reflns_Friedel_coverage         0.612
_reflns_Friedel_fraction_full    0.845
_reflns_Friedel_fraction_max     0.845
_reflns_number_gt                2113
_reflns_number_total             3376
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj00529a2.cif
_cod_data_source_block           Compound4aa
_cod_depositor_comments
'Adding full bibliography for 7062416--7062421.cif.'
_cod_original_cell_volume        2071.92(16)
_cod_database_code               7062416
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.963
_reflns_odcompleteness_completeness 97.83
_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
2. Uiso/Uaniso restraints and constraints
Uanis(C22) = Uanis(C23)
3.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B)
3.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C8(H8), C15(H15), C20(H20), C12(H12), C11(H11), C24(H24), C9(H9),
 C18(H18), C10(H10), C17(H17), C16(H16), C23(H23), C21(H21), C22(H22)
;
_shelx_res_checksum              26975
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.790
_oxdiff_exptl_absorpt_empirical_full_min 0.304