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_7062418
_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         'C38 H34 N4 O11 S2, 1[CH2Cl2]'
_chemical_formula_sum            'C39 H36 Cl2 N4 O11 S2'
_chemical_formula_weight         871.74
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-18
_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                   25.8268(11)
_cell_length_b                   16.2750(7)
_cell_length_c                   10.0472(5)
_cell_measurement_reflns_used    8330
_cell_measurement_temperature    284
_cell_measurement_theta_max      25.0250
_cell_measurement_theta_min      2.4940
_cell_volume                     4223.2(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      284
_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    -39.00   0.00   0.50   14.00    --  -14.97 -32.00 -44.00   78
  2  \w     -8.00  44.00   0.50   14.00    --   16.22 -61.00 -30.00  104
  3  \w    -13.00  21.00   0.50   14.00    --  -14.97 -94.00   0.00   68
  4  \w     10.00  40.00   0.50   14.00    --   16.22-125.00  60.00   60
  5  \w    -50.00 -14.00   0.50   14.00    --   16.22 -61.00 -30.00   72
  6  \w    -69.00 -22.00   0.50   14.00    --  -14.97 125.00  60.00   94
  7  \w    -81.00 -19.00   0.50   14.00    --  -14.97 143.00 -19.00  124
  8  \w      4.00  45.00   0.50   14.00    --  -14.97  30.00-180.00   82
  9  \w    -40.00 -15.00   0.50   14.00    --  -14.97  30.00-180.00   50
 10  \w    -69.00 -26.00   0.50   14.00    --  -14.97 125.00 150.00   86
 11  \w    -45.00  50.00   0.50   14.00    --   16.22 -90.00 166.00  190
;
_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      0.0089145000
_diffrn_orient_matrix_UB_12      -0.0289556000
_diffrn_orient_matrix_UB_13      -0.0474931000
_diffrn_orient_matrix_UB_21      0.0058325000
_diffrn_orient_matrix_UB_22      -0.0279947000
_diffrn_orient_matrix_UB_23      0.0520046000
_diffrn_orient_matrix_UB_31      -0.0253115000
_diffrn_orient_matrix_UB_32      -0.0166745000
_diffrn_orient_matrix_UB_33      -0.0047368000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            24055
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.503
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54631
_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    1.371
_exptl_crystal_description       needle
_exptl_crystal_F_000             1808
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0579
_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^)+(0.0770P)^2^+1.2455P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1543
_refine_ls_wR_factor_ref         0.1784
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2260
_reflns_number_total             3723
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj00529a2.cif
_cod_data_source_block           Compound6hc
_cod_depositor_comments
'Adding full bibliography for 7062416--7062421.cif.'
_cod_database_code               7062418
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.940
_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
2. Uiso/Uaniso restraints and constraints
Uanis(O003) = Uanis(S1)
3.a Ternary CH refined with riding coordinates:
 C9(H9), C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C6(H6), C14(H14), C2(H2), C4(H4), C18(H18), C5(H5), C3(H3),
 C17(H17), C16(H16)
3.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              95969
_shelx_fab_checksum              75333
_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 2.152
_oxdiff_exptl_absorpt_empirical_full_min 0.453