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_7160646
_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         'C29 H30 Br2 N2 O3'
_chemical_formula_sum            'C29 H30 Br2 N2 O3'
_chemical_formula_weight         614.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_creation_date             2024-04-30
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-07-10 deposited with the CCDC.	2025-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                84.172(10)
_cell_angle_beta                 79.375(8)
_cell_angle_gamma                89.555(9)
_cell_formula_units_Z            4
_cell_length_a                   9.343(2)
_cell_length_b                   13.457(3)
_cell_length_c                   22.540(5)
_cell_measurement_reflns_used    9866
_cell_measurement_temperature    298
_cell_measurement_theta_max      21.15
_cell_measurement_theta_min      2.24
_cell_volume                     2770.8(11)
_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      298
_diffrn_measured_fraction_theta_full 0.6975
_diffrn_measured_fraction_theta_max 0.6975
_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  0.0536
_diffrn_reflns_av_unetI/netI     0.0981
_diffrn_reflns_Laue_measured_fraction_full 0.6975
_diffrn_reflns_Laue_measured_fraction_max 0.6975
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9297
_diffrn_reflns_point_group_measured_fraction_full 0.6975
_diffrn_reflns_point_group_measured_fraction_max 0.6975
_diffrn_reflns_theta_full        23.0309
_diffrn_reflns_theta_max         23.03
_diffrn_reflns_theta_min         2.22
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.958
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5508
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0839 before and 0.0696 after correction.
The Ratio of minimum to maximum transmission is 0.7388.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       block
_exptl_crystal_F_000             1135.112
_exptl_crystal_size_max          0.273
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.234
_refine_diff_density_max         0.6563
_refine_diff_density_min         -0.9225
_refine_diff_density_rms         0.1566
_refine_ls_d_res_high            0.9083
_refine_ls_d_res_low             9.1822
_refine_ls_goodness_of_fit_ref   1.0432
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    98
_refine_ls_number_parameters     657
_refine_ls_number_reflns         5401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0432
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0559
_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^)+(0.0226P)^2^+8.4161P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              -13
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                3240
_reflns_number_total             5401
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ob00840a2.cif
_cod_data_source_block           2_Br_150424_0m_b
_cod_depositor_comments
'Adding full bibliography for 7160645--7160648.cif.'
_cod_database_code               7160646
_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:
 C01C(H01C), C01O(H01O), C03F(H03h), C01U(H01U), C02A(H02c), C03N(H03z)
2.b Secondary CH2 refined with riding coordinates:
 C01I(H01a,H01b), C02F(H02a,H02b), C03V(H03i,H03j), C02Y(H02d,H02e), C02Z(H02f,
 H02g), C03I(H03v,H03w)
2.c Aromatic/amide H refined with riding coordinates:
 C03D(H03g), C031(H031), C02X(H02X), C03P(H03P), C02J(H02J), C014(H014),
 C02R(H02R), C00V(H00V), C037(H037), C03C(H03r), C03S(H03), C01B(H01d),
 C00N(H00N), C030(H030), C03T(H1), C00T(H00T), C01R(H01R), C038(H038)
2.d Idealised Me refined as rotating group:
 C2(H2a,H2b,H2c), C032(H03a,H03b,H03c), C036(H03d,H03e,H03f), C03E(H03k,H03l,
 H03m), C03M(H03n,H03o,H03q), C01P(H01e,H01f,H01g), C03G(H03s,H03t,H03u),
 C03L(H03x,H03y,H)
;
_olex2_submission_special_instructions 'No special instructions were received'