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_7062417
_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 H25 N5 O4 S'
_chemical_formula_sum            'C25 H25 N5 O4 S'
_chemical_formula_weight         491.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-01-19
_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                 112.054(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.3465(7)
_cell_length_b                   10.9821(3)
_cell_length_c                   23.9221(9)
_cell_measurement_reflns_used    20816
_cell_measurement_temperature    297.6
_cell_measurement_theta_max      26.4770
_cell_measurement_theta_min      2.1360
_cell_volume                     4954.2(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      297.6
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     -8.00  36.00   0.50   30.00    --   16.22  45.00 -30.00   88
  2  \w     45.00  76.00   0.50   30.00    --   16.22  45.00 -30.00   62
  3  \w     39.00  64.00   0.50   30.00    --   16.22  45.00 -60.00   50
  4  \w     27.00  61.00   0.50   30.00    --  -14.97  25.00 -61.00   68
  5  \w     14.00  39.00   0.50   30.00    --   16.22  25.00 -61.00   50
  6  \w     -9.00  85.00   0.50   30.00    --   16.22  61.00   0.00  188
  7  \w    -18.00  10.00   0.50   30.00    --  -14.97 -45.00 120.00   56
  8  \w    -17.00  20.00   0.50   30.00    --   16.22 -25.00 134.00   74
  9  \w    -47.00 -22.00   0.50   30.00    --  -14.97 -25.00 134.00   50
 10  \w    -52.00 -27.00   0.50   30.00    --  -14.97 -45.00 120.00   50
 11  \w    -89.00 -64.00   0.50   30.00    --  -14.97 -25.00 134.00   50
 12  \w    -35.00  19.00   0.50   30.00    --  -14.97 -94.00  60.00  108
 13  \w     10.00  66.00   0.50   30.00    --   16.22-125.00  60.00  112
 14  \w    -36.00   6.00   0.50   30.00    --  -14.97  25.00 -61.00   84
 15  \w    -43.00 -12.00   0.50   30.00    --  -14.97 125.00  60.00   62
 16  \w    -63.00  75.00   0.50   30.00    --   16.22 -15.00  60.00  276
 17  \w    -22.00  53.00   0.50   30.00    --   16.22 -94.00 -90.00  150
 18  \w     23.00  60.00   0.50   30.00    --   16.22-125.00-120.00   74
 19  \w    -35.00  21.00   0.50   30.00    --  -14.97 -94.00-150.00  112
;
_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      -0.0114580000
_diffrn_orient_matrix_UB_12      0.0174059000
_diffrn_orient_matrix_UB_13      0.0234045000
_diffrn_orient_matrix_UB_21      0.0355925000
_diffrn_orient_matrix_UB_22      0.0127703000
_diffrn_orient_matrix_UB_23      0.0189729000
_diffrn_orient_matrix_UB_31      -0.0041785000
_diffrn_orient_matrix_UB_32      0.0609208000
_diffrn_orient_matrix_UB_33      -0.0106669000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            52122
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         1.854
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72423
_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            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       needle
_exptl_crystal_F_000             2064
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.951
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     619
_refine_ls_number_reflns         8741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1436
_refine_ls_R_factor_gt           0.1008
_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^)+(0.1906P)^2^+3.5939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3121
_refine_ls_wR_factor_ref         0.3473
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5049
_reflns_number_total             8741
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj00529a2.cif
_cod_data_source_block           Compound5ba
_cod_depositor_comments
'Adding full bibliography for 7062416--7062421.cif.'
_cod_database_code               7062417
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.966
_reflns_odcompleteness_completeness 99.61
_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(C24) = Uanis(O4)
Uanis(C23) = Uanis(C24)
Uanis(C25) = Uanis(C24)
3.a Ternary CH refined with riding coordinates:
 C24(H24), C49(H49)
3.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C48(H48A,H48B), C50(H50A,H50B), C25(H25A,H25B)
3.c Aromatic/amide H refined with riding coordinates:
 C35(H35), C21(H21), C39(H39), C40(H40), C27(H27), C46(H46), C14(H14),
 C43(H43), C15(H15), C45(H45), C31(H31), C10(H10), C20(H20), C28(H28), C42(H42),
  C18(H18), C37(H37), C38(H38), C17(H17), C36(H36), C13(H13), C29(H29),
 C11(H11), C30(H30), C12(H12), C2(H2), C3(H3A), C5(H5), C4(H4A), C6(H6)
3.d Idealised Me refined as rotating group:
 C47(H47A,H47B,H47C), C22(H22A,H22B,H22C)
3.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O7(H7), O3(H3), O8(H8)
;
_shelx_res_checksum              16743
_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 2.490
_oxdiff_exptl_absorpt_empirical_full_min 0.596