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_7134066
_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_absolute_configuration rm
_chemical_formula_moiety         'C20 H18 Cl N3 O7'
_chemical_formula_sum            'C20 H18 Cl N3 O7'
_chemical_formula_weight         447.82
_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     dual
_audit_creation_date             2024-09-03
_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            8
_cell_length_a                   9.3164(6)
_cell_length_b                   10.0835(6)
_cell_length_c                   42.612(3)
_cell_measurement_reflns_used    9418
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      66.512
_cell_measurement_theta_min      4.506
_cell_volume                     4003.1(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            64207
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.615
_diffrn_reflns_theta_max         66.615
_diffrn_reflns_theta_min         2.074
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.138
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1255 before and 0.0759 after correction.
The Ratio of minimum to maximum transmission is 0.5970.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.094(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     564
_refine_ls_number_reflns         7043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0241
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0322P)^2^+1.1376P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0626
_refine_ls_wR_factor_ref         0.0630
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                6875
_reflns_number_total             7043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06145d2.cif
_cod_data_source_block           cu_ms_884_rep_0ma
_cod_depositor_comments
'Adding full bibliography for 7134066--7134067.cif.'
_cod_original_cell_volume        4003.1(4)
_cod_database_code               7134066
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.90554
 0.09446
2.a Ternary CH refined with riding coordinates:
 C00Y(H00Y), C011(H011), C012(H012), C015(H015), C018(H018), C01K(H01K)
2.b Secondary CH2 refined with riding coordinates:
 C014(H01A,H01B), C017(H01L,H01M), C01I(H01S,H01T), C01O(H01F,H01G)
2.c Aromatic/amide H refined with riding coordinates:
 C00R(H00R), C00S(H00S), C00T(H00T), C00V(H00V), C00W(H00W), C010(H010),
 C013(H013), C016(H016), C01B(H01N), C01D(H01O)
2.d Idealised Me refined as rotating group:
 C01H(H01P,H01Q,H01R), C01J(H01C,H01D,H01E), C01P(H01H,H01I,H01J), C01Q(H01U,
 H01V,H01W)
;
_shelx_res_checksum              97379
_shelx_hkl_checksum              71880
_olex2_submission_special_instructions 'No special instructions were received'