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_7062421
_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         'C24 H19 Cl2 N O4 S'
_chemical_formula_sum            'C24 H19 Cl2 N O4 S'
_chemical_formula_weight         488.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2022-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-01-20 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.799(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9092(17)
_cell_length_b                   6.0215(7)
_cell_length_c                   29.195(4)
_cell_measurement_reflns_used    9364
_cell_measurement_temperature    296.0
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.29
_cell_volume                     2242.7(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.0
_diffrn_measured_fraction_theta_full 0.9955
_diffrn_measured_fraction_theta_max 0.9955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            34376
_diffrn_reflns_theta_full        27.5215
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.60
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4463
_exptl_crystal_description       block
_exptl_crystal_F_000             1010.1247
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.7330
_refine_diff_density_min         -0.5645
_refine_diff_density_rms         0.0799
_refine_ls_d_res_high            0.7691
_refine_ls_d_res_low             12.7573
_refine_ls_goodness_of_fit_ref   1.0091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0091
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+1.0252P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1441
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              37
_reflns_limit_l_min              0
_reflns_number_gt                3649
_reflns_number_total             5135
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3nj00529a2.cif
_cod_data_source_block           Compound4db
_cod_depositor_comments
'Adding full bibliography for 7062416--7062421.cif.'
_cod_database_code               7062421
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C14(H14), C8(H8), C4(H4), C20(H20), C15(H15), C7(H7),
 C24(H24), C5(H5), C21(H21), C23(H23), C22(H22)
;
_olex2_submission_special_instructions 'No special instructions were received'