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_7062419
_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         'C25 H24 Cl N5 O5 S, 0.5[CHCl3]'
_chemical_formula_sum            'C25.5 H24.5 Cl2.5 N5 O5 S'
_chemical_formula_weight         601.68
_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             2023-01-20
_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                69.515(3)
_cell_angle_beta                 75.700(3)
_cell_angle_gamma                88.454(3)
_cell_formula_units_Z            2
_cell_length_a                   10.4254(3)
_cell_length_b                   11.9858(4)
_cell_length_c                   12.4011(3)
_cell_measurement_reflns_used    8052
_cell_measurement_temperature    299
_cell_measurement_theta_max      24.5370
_cell_measurement_theta_min      1.9920
_cell_volume                     1403.61(8)
_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      299
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.941
_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    -17.00   8.00   0.50    5.09    --  -15.60 -32.00 -20.00   50
  2  \w    -36.00  15.00   0.50    5.09    --  -15.60 -94.00  30.00  102
  3  \w    -37.00  44.00   0.50    5.09    --   16.22 -94.00  60.00  162
  4  \w    -37.00  16.00   0.50    5.09    --  -15.60 -94.00  90.00  106
  5  \w    -65.00  -4.00   0.50    5.09    --  -15.60 -45.00 120.00  122
  6  \w      0.00  57.00   0.50    5.09    --  -15.60  32.00 138.00  114
  7  \w     -7.00  89.00   0.50    5.09    --   16.22  32.00 138.00  192
  8  \w     -2.00  24.00   0.50    5.09    --   16.22  45.00  30.00   52
  9  \w     34.00  60.00   0.50    5.09    --   16.22  45.00  30.00   52
 10  \w    -37.00   9.00   0.50    5.09    --  -15.60 -94.00 -60.00   92
 11  \w     44.00  70.00   0.50    5.09    --   16.22-125.00 -90.00   52
 12  \w    -35.00  18.00   0.50    5.09    --  -15.60 -94.00-120.00  106
 13  \w    -52.00  39.00   0.50    5.09    --   16.22 -30.00-150.00  182
 14  \w     10.00  52.00   0.50    5.09    --  -15.60  61.00-120.00   84
 15  \w    -42.00   2.00   0.50    5.09    --  -15.60  61.00-120.00   88
 16  \w    -69.00 -43.00   0.50    5.09    --  -15.60 125.00 -90.00   52
 17  \w    -60.00 -34.00   0.50    5.09    --  -15.60 -32.00 -20.00   52
 18  \w    -57.00  -9.00   0.50    5.09    --   16.22 -32.00 -20.00   96
 19  \w    -77.00   9.00   0.50    5.09    --  -15.60 -45.00 -90.00  172
 20  \w    -57.00 -19.00   0.50    5.09    --  -15.60 125.00  90.00   76
 21  \w    -85.00 -22.00   0.50    5.09    --  -15.60 -30.00 150.00  126
;
_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      -0.0465788000
_diffrn_orient_matrix_UB_12      0.0150827000
_diffrn_orient_matrix_UB_13      -0.0351444000
_diffrn_orient_matrix_UB_21      0.0527212000
_diffrn_orient_matrix_UB_22      0.0202916000
_diffrn_orient_matrix_UB_23      -0.0523464000
_diffrn_orient_matrix_UB_31      0.0012999000
_diffrn_orient_matrix_UB_32      -0.0580415000
_diffrn_orient_matrix_UB_33      -0.0030316000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19754
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.262
_diffrn_reflns_theta_min         2.020
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67982
_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 whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       plate
_exptl_crystal_F_000             622
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0724P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1622
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3605
_reflns_number_total             5921
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj00529a2.cif
_cod_data_source_block           Compound5cb
_cod_depositor_comments
'Adding full bibliography for 7062416--7062421.cif.'
_cod_original_formula_sum        'C25.50 H24.50 Cl2.50 N5 O5 S'
_cod_database_code               7062419
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S Cl'
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.925
_reflns_odcompleteness_completeness 99.49
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C17) = Uanis(C16)
3.a Ternary CH refined with riding coordinates:
 C24(H24)
3.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C25(H25A,H25B)
3.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C1(H1), C14(H14), C2(H2), C10(H10), C21(H21), C5(H5), C17(H17),
 C20(H20), C18(H18), C11(H11), C4(H4A), C13(H13), C12(H12)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
3.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              53658
_shelx_fab_checksum              67021
_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 7.313
_oxdiff_exptl_absorpt_empirical_full_min 0.373