Iterative Assembly of Nitrile Oxides and Ynamides: Synthesis of Isoxazoles and Pyrroles.
Chen, Changwei; Cui, Sunliang; The Journal of organic chemistry 84 (2019) 12157–12164; doi:10.1021/acs.joc.9b01430

data_4034470
_publ_section_title
;
 Iterative Assembly of Nitrile Oxides and Ynamides: Synthesis of
 Isoxazoles and Pyrroles.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12157
_journal_page_last               12164
_journal_paper_doi               10.1021/acs.joc.9b01430
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C H Cl3, C33 H30 F N3 O5 S2'
_chemical_formula_sum            'C34 H31 Cl3 F N3 O5 S2'
_chemical_formula_weight         751.09
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                106.863(2)
_cell_angle_beta                 98.061(2)
_cell_angle_gamma                93.610(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6255(4)
_cell_length_b                   11.1263(5)
_cell_length_c                   17.2047(8)
_cell_measurement_reflns_used    9161
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      29.54
_cell_measurement_theta_min      2.51
_cell_volume                     1735.43(14)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.01
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_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  0.0305
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            30531
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.573
_diffrn_reflns_theta_min         2.302
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1062 before and 0.0485 after correction.
The Ratio of minimum to maximum transmission is 0.8931.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.407
_exptl_crystal_size_min          0.214
_refine_diff_density_max         0.980
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         9649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0493
_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^)+(0.0661P)^2^+1.1424P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8218
_reflns_number_total             9649
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01430_si_003.cif
_cod_data_source_block           190312_ccw_9_5_3_0m
_cod_original_cell_volume        1735.43(13)
_cod_database_code               4034470
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.812
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C34(H34)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C8(H8), C10(H10), C11(H11), C14(H14), C15(H15), C17(H17),
 C18(H18), C22(H22), C23(H23), C25(H25), C26(H26), C29(H29), C30(H30), C31(H31),
  C32(H32), C33(H33)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C12(H12A,H12B,H12C), C20(H20A,H20B,H20C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              97119
_shelx_hkl_checksum              84174
_olex2_submission_special_instructions 'No special instructions were received'