Organocatalytic asymmetric synthesis of quaternary α-isoxazole-α-alkynylamino acid derivatives
Li, Min; Chen, Yihua; Yan, Yinkun; Liu, Min; Huang, Min; Li, Wenzhe; Cao, Lianyi; Zhang, Xiao-Mei; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01746F

data_7158957
_publ_section_title
;
 Organocatalytic asymmetric synthesis of quaternary
 \a-isoxazole-\a-alkynylamino acid derivatives
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01746F
_journal_year                    2022
_chemical_formula_moiety         'C28 H30 I N3 O5'
_chemical_formula_sum            'C28 H30 I N3 O5'
_chemical_formula_weight         615.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-02-28 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.711(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.330(2)
_cell_length_b                   10.0441(6)
_cell_length_c                   16.8467(17)
_cell_measurement_reflns_used    2214
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4230
_cell_measurement_theta_min      3.3820
_cell_volume                     2770.6(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -15.00   17.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336  -99.0000  -90.0000 32

  2 omega  -21.00   24.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6648  -57.0000  -90.0000 45

  3 omega   12.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6648   38.0000 -120.0000 70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0299464000
_diffrn_orient_matrix_UB_12      0.0143833000
_diffrn_orient_matrix_UB_13      -0.0437418000
_diffrn_orient_matrix_UB_21      0.0292224000
_diffrn_orient_matrix_UB_22      -0.0115310000
_diffrn_orient_matrix_UB_23      -0.0160214000
_diffrn_orient_matrix_UB_31      -0.0111920000
_diffrn_orient_matrix_UB_32      -0.0683098000
_diffrn_orient_matrix_UB_33      -0.0065515000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14402
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.018
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.217
_refine_diff_density_min         -1.217
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         5654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+2.0896P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4161
_reflns_number_total             5654
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01746f2.cif
_cod_data_source_block           210410_s1_lm
_cod_database_code               7158957
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         c12h12n2o3i1
_shelx_estimated_absorpt_t_max   0.754
_shelx_estimated_absorpt_t_min   0.679
_reflns_odcompleteness_completeness 83.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C24(H24), C25(H25),
 C26(H26), C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C14(H14A,H14B,
 H14C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              70994
_olex2_submission_special_instructions 'No special instructions were received'