Four-Component Reactions for the Synthesis of Perfluoroalkyl Isoxazoles
Chen, Yuanjin; Li, Liangkui; He, Xiao; Li, Zhiping; ACS Catalysis 9 (2019) 9098–; doi:10.1021/acscatal.9b03189

data_4514614
_publ_section_title
;
 Four-Component Reactions for the Synthesis of Perfluoroalkyl Isoxazoles
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              9098
_journal_paper_doi               10.1021/acscatal.9b03189
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C14 H14 Br F2 N O'
_chemical_formula_sum            'C14 H14 Br F2 N O'
_chemical_formula_weight         330.17
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-06-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                93.330(5)
_cell_angle_beta                 100.541(5)
_cell_angle_gamma                92.151(6)
_cell_formula_units_Z            4
_cell_length_a                   9.6165(14)
_cell_length_b                   11.7307(19)
_cell_length_c                   12.5720(18)
_cell_measurement_reflns_used    5295
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.918
_cell_measurement_theta_min      2.319
_cell_volume                     1390.3(4)
_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)'
_diffrn_ambient_temperature      169.99
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_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  0.0960
_diffrn_reflns_av_unetI/netI     0.1169
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18047
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_min         2.319
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.971
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1623 before and 0.0952 after correction. The Ratio of minimum to maximum transmission is 0.5958. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         2.513
_refine_diff_density_min         -1.030
_refine_diff_density_rms         0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         6364
_refine_ls_number_restraints     92
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1684
_refine_ls_R_factor_gt           0.0978
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1187P)^2^+10.2470P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2424
_refine_ls_wR_factor_ref         0.2857
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3689
_reflns_number_total             6364
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03189_si_002.cif
_cod_data_source_block           mo_cyj2019052801_0m_a
_cod_depositor_comments
;

2020-04-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C14 H14 Br F2 N O)'
_cod_original_formula_sum        'C28 H28 Br2 F4 N2 O2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     660.34
_cod_database_code               4514614
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.717
_shelx_estimated_absorpt_t_min   0.617
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H3AC-H0AA
 2 with sigma of 0.01
 C2-C2AA
 1.42 with sigma of 0.02
 H1AB-H2AB
 1.9 with sigma of 0.01
 H2AB-H1AB
 2.05 with sigma of 0.01
 H3AB-H4AB
 2.05 with sigma of 0.01
 H3AA-H4AC
 2.05 with sigma of 0.01
 H1AA-H2AB
 2.05 with sigma of 0.01
 H3AC-H20
 2.05 with sigma of 0.01
3. Rigid bond restraints
 C18, C4AA, C0AA, C3AA, C2, C2AA, C1, C1AA
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C2AA \\sim C2 \\sim C1AA \\sim C1 \\sim C3AA \\sim C18 \\sim C4AA \\sim C0AA:
within 3.5A with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C15(H15), C16(H16), C20(H20), C21(H21), C24(H24),
 C27(H27), C28(H28)
5.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C0AA(H0AA,H0AB,H0AC), C4AA(H4AA,H4AB,H4AC), C1AA(H1AA,H1AB,
 H1AC), C2AA(H2AA,H2AB,H2AC), C3AA(H3AA,H3AB,H3AC)
;
_shelx_res_checksum              4095
_shelx_hkl_checksum              23066
_olex2_submission_special_instructions 'No special instructions were received'