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_7062420
_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_formula_moiety         'C31 H27 N O4 S'
_chemical_formula_sum            'C31 H27 N O4 S'
_chemical_formula_weight         509.59
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-31
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2023-04-01 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                76.121(5)
_cell_angle_beta                 83.698(5)
_cell_angle_gamma                89.177(5)
_cell_formula_units_Z            4
_cell_length_a                   7.7998(5)
_cell_length_b                   16.6494(10)
_cell_length_c                   21.1710(14)
_cell_measurement_reflns_used    7266
_cell_measurement_temperature    111.88
_cell_measurement_theta_max      19.5900
_cell_measurement_theta_min      1.9800
_cell_volume                     2652.7(3)
_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      111.88
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_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    -11.00  86.00   0.50    3.30    --   16.22  61.00  30.00  194
  2  \w     -8.00  86.00   0.50    3.30    --   16.22  45.00 -60.00  188
  3  \w     -8.00  86.00   0.50    3.30    --   16.22  45.00-150.00  188
  4  \w    -11.00  86.00   0.50    3.30    --   16.22  61.00-180.00  194
  5  \w    -11.00  86.00   0.50    3.30    --   16.22  61.00 -90.00  194
  6  \w    -37.00  22.00   0.50    3.30    --  -14.97 -94.00   0.00  118
  7  \w     12.00  73.00   0.50    3.30    --   16.22-128.00 -56.00  122
  8  \w    -37.00  22.00   0.50    3.30    --  -14.97 -94.00 -60.00  118
  9  \w    -37.00  53.00   0.50    3.30    --   16.22 -94.00 -90.00  180
 10  \w    -39.00  55.00   0.50    3.30    --  -14.97  45.00-180.00  188
 11  \w    -43.00  55.00   0.50    3.30    --  -14.97  61.00 -60.00  196
 12  \w    -10.00  90.00   0.50    3.30    --   16.22  30.00  60.00  200
 13  \w     -8.00  86.00   0.50    3.30    --   16.22  45.00 150.00  188
 14  \w     -8.00  86.00   0.50    3.30    --   16.22  45.00  60.00  188
 15  \w     19.00  81.00   0.50    3.30    --   16.22-141.00 132.00  124
 16  \w    -41.00  59.00   0.50    3.30    --  -14.97  30.00 120.00  200
 17  \w    -42.00 -13.00   0.50    3.30    --   16.22 131.00 164.63   58
 18  \w    -69.00 -10.00   0.50    3.30    --  -14.97 125.00 120.00  118
 19  \w    -71.00 -11.00   0.50    3.30    --  -14.97 128.00  17.00  120
 20  \w    -69.00  99.00   0.50    3.30    --   16.22   0.00-150.00  336
 21  \w    -79.00 -18.00   0.50    3.30    --  -14.97 141.00-170.00  122
;
_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      -0.0069334000
_diffrn_orient_matrix_UB_12      0.0031541000
_diffrn_orient_matrix_UB_13      0.0330032000
_diffrn_orient_matrix_UB_21      0.0205179000
_diffrn_orient_matrix_UB_22      0.0428216000
_diffrn_orient_matrix_UB_23      -0.0107222000
_diffrn_orient_matrix_UB_31      -0.0888978000
_diffrn_orient_matrix_UB_32      0.0090775000
_diffrn_orient_matrix_UB_33      -0.0011347000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2093
_diffrn_reflns_av_unetI/netI     0.1464
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            55589
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.407
_diffrn_reflns_theta_max         24.407
_diffrn_reflns_theta_min         2.088
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
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    1.276
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     669
_refine_ls_number_reflns         8720
_refine_ls_number_restraints     578
_refine_ls_restrained_S_all      0.918
_refine_ls_R_factor_all          0.2074
_refine_ls_R_factor_gt           0.0954
_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^)+(0.1521P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2297
_refine_ls_wR_factor_ref         0.3113
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3545
_reflns_number_total             8720
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj00529a2.cif
_cod_data_source_block           Compound7la
_cod_depositor_comments
'Adding full bibliography for 7062416--7062421.cif.'
_cod_database_code               7062420
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.970
_reflns_odcompleteness_completeness 99.80
_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. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C00D(H00D), C3(H3), C35(H35), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C36(H36A,H36B), C1(H1A,H1B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C32(H32), C7(H7), C11(H11), C38(H38), C44(H44), C48(H48), C10(H10),
 C45(H45), C13(H13), C8(H8), C46(H46), C40(H40), C9(H9), C47(H47), C31(H31),
 C62(H62), C58(H58), C27(H27), C20(H20), C22(H22), C42(H42), C19(H19), C39(H39),
  C23(H23), C14(H14), C50(H50), C51(H51), C60(H60), C17(H17), C15(H15),
 C54(H54), C59(H59), C30(H30), C41(H41), C61(H61), C28(H28), C53(H53), C16(H16),
  C29(H29)
3.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C55(H55A,H55B,H55C)
;
_shelx_res_checksum              95274
_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 3.200
_oxdiff_exptl_absorpt_empirical_full_min 0.417