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_7160645
_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_absolute_configuration unk
_chemical_formula_moiety         '(C29 H30 Cl2 N2 O3)'
_chemical_formula_sum            'C29 H30 Cl2 N2 O3'
_chemical_formula_weight         525.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_symmetry_Int_Tables_number      7
_audit_creation_date             2024-04-29
_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                 100.025(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2353(7)
_cell_length_b                   13.3183(10)
_cell_length_c                   22.4290(16)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    299.00
_cell_measurement_theta_max      20.66
_cell_measurement_theta_min      2.27
_cell_volume                     2716.6(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 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      299.00
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9988
_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  0.0681
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_Laue_measured_fraction_full 0.9994
_diffrn_reflns_Laue_measured_fraction_max 0.9988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            67185
_diffrn_reflns_point_group_measured_fraction_full 0.9900
_diffrn_reflns_point_group_measured_fraction_max 0.9735
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.79
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1421 before and 0.0739 after correction.
The Ratio of minimum to maximum transmission is 0.9004.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.3232
_refine_diff_density_min         -0.4641
_refine_diff_density_rms         0.0807
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.44(2)
_refine_ls_d_res_high            0.7493
_refine_ls_d_res_low             11.4052
_refine_ls_goodness_of_fit_ref   1.1443
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    98
_refine_ls_number_parameters     657
_refine_ls_number_reflns         13184
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.1443
_refine_ls_R_factor_all          0.1356
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0568P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1464
_reflns_Friedel_coverage         0.948
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              17
_reflns_limit_k_min              -17
_reflns_limit_l_max              27
_reflns_limit_l_min              -29
_reflns_number_gt                6752
_reflns_number_total             13543
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ob00840a2.cif
_cod_data_source_block           2_Cl_150424_0m_a
_cod_depositor_comments
'Adding full bibliography for 7160645--7160648.cif.'
_cod_original_sg_symbol_Hall     ' P -2yac'
_cod_original_sg_symbol_H-M      'P n'
_cod_database_code               7160645
_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:
 C00J(H00J), C00L(H00L), C00M(H00M), C00U(H00U), C00W(H00W), C00Y(H00Y)
2.b Secondary CH2 refined with riding coordinates:
 C017(H01w,H01x), C01B(H01y,H), C01J(H01e,H01g), C01L(H2,Hc), C01N(H01l,H01m),
 C01P(H01n,H01o)
2.c Aromatic/amide H refined with riding coordinates:
 C016(H016), C020(H020), C01V(H01V), C00Z(H00Z), C018(H018), C01I(H01I),
 C015(H015), C01A(H01A), C01K(H1), C01W(H7), C01X(H8), C01T(H5), C01Z(H10),
 C01Y(H9), C013(H013), C00N(H00N), C01D(H01), C01F(H01F)
2.d Idealised Me refined as rotating group:
 C01C(H01z,Ha,Hb), C01E(H01b,H01c,H01d), C01M(H01h,H01j,H01k), C01O(H3,Hd,He),
 C01Q(H01p,H01q,H01r), C01R(H4,Hf,Hg), C01S(H01s,H01t,H01u), C01U(H6,Hh,Hi)
;
_olex2_submission_special_instructions 'No special instructions were received'