Regioselective (3 + 2) cycloaddition reactions of zerumbone: synthesis of isoxazolines and spiro-pyrrolizidino-oxindoles, conformational diversity and theoretical insights.
Murthi, Nandha Kumar; Nulakani, Naga Venkateswara Rao; Akbar Ali, Mohamad; Kundu, Tanay; Gopinath, Pushparathinam; Organic & biomolecular chemistry 23 (2025) 7956–7961; doi:10.1039/d5ob00840a

data_7160648
_publ_section_title
;
 Regioselective (3 + 2) cycloaddition reactions of zerumbone: synthesis of
 isoxazolines and spiro-pyrrolizidino-oxindoles, conformational diversity
 and theoretical insights.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7956
_journal_page_last               7961
_journal_paper_doi               10.1039/d5ob00840a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C22 H27 N O2'
_chemical_formula_sum            'C22 H27 N O2'
_chemical_formula_weight         337.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2024-05-02
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-06-14 deposited with the CCDC.	2025-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.576(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6648(3)
_cell_length_b                   21.5471(7)
_cell_length_c                   10.7458(3)
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.63
_cell_volume                     1890.29(10)
_computing_cell_refinement       'SAINT V8.40E (?, 2016)'
_computing_data_reduction        'SAINT V8.40E (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9979
_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  0.0632
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            49003
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9979
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.89
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0904 before and 0.0644 after correction.
The Ratio of minimum to maximum transmission is 0.9315.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.3063
_refine_diff_density_min         -0.2244
_refine_diff_density_rms         0.0589
_refine_ls_d_res_high            0.7494
_refine_ls_d_res_low             10.7736
_refine_ls_goodness_of_fit_ref   1.0835
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    39
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0835
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0673
_refine_ls_shift/su_max          -0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+1.0885P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1504
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -11
_reflns_limit_k_max              28
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              -6
_reflns_number_gt                3727
_reflns_number_total             4715
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ob00840a2.cif
_cod_data_source_block           zr
_cod_depositor_comments
'Adding full bibliography for 7160645--7160648.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7160648
_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.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4a,H4b), C13(H13a,H13b), C14(H14a,H14b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C11(H11), C12(H12), C15(H15), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C19(H19a,H19b,H19c), C20(H20a,H20b,H20c)
;
_olex2_submission_special_instructions 'No special instructions were received'