Asymmetric desymmetrization of 2,5-cyclohexadienones initiated by organocatalytic conjugate addition to 4-nitro-5-styrylisoxazoles.
Sharma, Manisha; Chauhan, Pankaj; Chemical communications (Cambridge, England) 61 (2025) 1455–1458; doi:10.1039/d4cc06145d

data_7134067
_publ_section_title
;
 Asymmetric desymmetrization of 2,5-cyclohexadienones initiated by
 organocatalytic conjugate addition to 4-nitro-5-styrylisoxazoles.
;
_journal_issue                   7
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1455
_journal_page_last               1458
_journal_paper_doi               10.1039/d4cc06145d
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         '0.095(C22 H21 N3 O8)'
_chemical_formula_sum            'C2.1 H2 N0.29 O0.76'
_chemical_formula_weight         43.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-09-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2024-09-05 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            42
_cell_length_a                   14.4284(10)
_cell_length_b                   9.8594(7)
_cell_length_c                   14.9252(8)
_cell_measurement_reflns_used    9794
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.47
_cell_volume                     2123.2(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.935
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.935
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10885
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        24.911
_diffrn_reflns_theta_max         24.911
_diffrn_reflns_theta_min         1.963
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6848
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0912 before and 0.0587 after correction.
The Ratio of minimum to maximum transmission is 0.9183.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             952
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Flack x determined using 963 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_extinction_coef       0.049(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         3468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0767
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1322P)^2^+2.2670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1981
_refine_ls_wR_factor_ref         0.2512
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                2607
_reflns_number_total             3468
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06145d2.cif
_cod_data_source_block           mo_ms_1004_0m_a_a
_cod_depositor_comments
'Adding full bibliography for 7134066--7134067.cif.'
_cod_original_formula_sum        'C2.10 H2 N0.29 O0.76'
_cod_database_code               7134067
_shelx_shelxl_version_number     2018/3
_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:
 C4(H4), C5(H5), C13(H13), C15(H15), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              48422
_shelx_hkl_checksum              89027
_olex2_submission_special_instructions 'No special instructions were received'