[3 + 2] Cycloaddition of Oxazol-5-(4H)-ones with Nitrones for Diastereoselective Synthesis of Isoxazolidin-5-ones.
Zhao, Hong-Wu; Liu, Yue-Yang; Zhao, Yu-Di; Pang, Hai-Liang; Chen, Xiao-Qin; Song, Xiu-Qing; Tian, Ting; Li, Bo; Yang, Zhao; Du, Juan; Feng, Ning-Ning; Organic letters  (2016) –; doi:10.1021/acs.orglett.6b03206

data_1544942
_publ_section_title
;
 [3 + 2] Cycloaddition of Oxazol-5-(4H)-ones with Nitrones for
 Diastereoselective Synthesis of Isoxazolidin-5-ones.
;
_journal_name_full               'Organic letters'
_journal_paper_doi               10.1021/acs.orglett.6b03206
_journal_year                    2016
_chemical_formula_moiety         'C30 H25 Cl N2 O3'
_chemical_formula_sum            'C30 H25 Cl N2 O3'
_chemical_formula_weight         496.97
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            24
_cell_length_a                   20.2861(8)
_cell_length_b                   24.7581(9)
_cell_length_c                   31.1511(12)
_cell_measurement_reflns_used    40401
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     15645.5(10)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_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      113.15
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            156576
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         3.090
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.9787
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             6240
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 12877 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.203(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1945
_refine_ls_number_reflns         34372
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0496P)^2^+2.9813P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0897
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.908
_reflns_number_gt                30702
_reflns_number_total             34372
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03206_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_database_code               1544942
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C38(H38), C68(H68), C98(H98), C128(H128), C158(H158)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C16(H16A,H16B), C37(H37A,H37B), C46(H46A,H46B), C67(H67A,H67B),
 C76(H76A,H76B), C97(H97A,H97B), C106(H10A,H10B), C127(H12A,H12B), C136(H13A,
 H13B), C157(H15A,H15B), C166(H16C,H16D)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4A), N6(H6), N8(H8A), N10(H10C), N12(H12), C1(H1), C2(H2A),
 C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27), C28(H28),
  C29(H29), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C40(H40),
 C41(H41), C43(H43), C44(H44), C48(H48), C49(H49), C50(H50), C51(H51), C52(H52),
  C55(H55), C56(H56), C57(H57), C58(H58), C59(H59), C61(H61), C62(H62),
 C63(H63), C64(H64), C65(H65), C70(H70), C71(H71), C73(H73), C74(H74), C78(H78),
  C79(H79), C80(H80), C81(H81), C82(H82), C85(H85), C86(H86), C87(H87),
 C88(H88), C89(H89), C91(H91), C92(H92), C93(H93), C94(H94), C95(H95),
 C100(H100), C101(H101), C103(H103), C104(H104), C108(H108), C109(H109),
 C110(H110), C111(H111), C112(H112), C115(H115), C116(H116), C117(H117),
 C118(H118), C119(H119), C121(H121), C122(H122), C123(H123), C124(H124),
 C125(H125), C130(H130), C131(H131), C133(H133), C134(H134), C138(H138),
 C139(H139), C140(H140), C141(H141), C142(H142), C145(H145), C146(H146),
 C147(H147), C148(H148), C149(H149), C151(H151), C152(H152), C153(H153),
 C154(H154), C155(H155), C160(H160), C161(H161), C163(H163), C164(H164),
 C168(H168), C169(H169), C170(H170), C171(H171), C172(H172), C175(H175),
 C176(H176), C177(H177), C178(H178), C179(H179)
;
_shelx_res_checksum              67557
_shelx_hkl_checksum              70647
_shelx_shelxl_version_number     2014/8
_olex2_submission_special_instructions 'No special instructions were received'