Gold Redox Catalysis for Cyclization/Arylation of Allylic Oximes: Synthesis of Isoxazoline Derivatives
Jimoh, Abiola Azeez; Hosseyni, Seyedmorteza; Ye, Xiaohan; Wojtas, Lukasz; Hu, Yong; Shi, Xiaodong; Chemical Communications  (2019) –; doi:10.1039/C9CC02830G

data_7123691
_publ_section_title
;
 Gold Redox Catalysis for Cyclization/Arylation of Allylic Oximes:
 Synthesis of Isoxazoline Derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC02830G
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H16 F N O'
_chemical_formula_sum            'C20 H16 F N O'
_chemical_formula_weight         305.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2018-12-03 deposited with the CCDC.    2019-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.9410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.84790(10)
_cell_length_b                   14.8989(4)
_cell_length_c                   17.0994(4)
_cell_measurement_reflns_used    9377
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.37
_cell_measurement_theta_min      2.60
_cell_volume                     1481.82(6)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21984
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.361
_diffrn_reflns_theta_min         2.598
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0960 before and 0.0678 after correction.
The Ratio of minimum to maximum transmission is 0.8881.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.429
_exptl_crystal_size_mid          0.408
_exptl_crystal_size_min          0.196
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 2530 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.20(7)
_refine_ls_extinction_coef       0.0117(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         5786
_refine_ls_number_restraints     1090
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.3994P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0888
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                5604
_reflns_number_total             5786
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc02830g2.cif
_cod_data_source_block           aaj_2055
_cod_database_code               7123691
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.867
_shelx_estimated_absorpt_t_min   0.739
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C36A-C35A = C37A-C36A = C37A-C32A = C33A-C32A = C34A-C33A = C35A-C34A = C36B-
 C35B = C37B-C36B = C37B-C32B = C33B-C32B = C34B-C33B = C35B-C34B
 1.39 with sigma of 0.005
 C6A-C5A = C7A-C6A = C7A-C2A = C3A-C2A = C4A-C3A = C5A-C4A = C6B-C5B = C7B-C6B
 = C7B-C2B = C3B-C2B = C4B-C3B = C5B-C4B
 1.39 with sigma of 0.005
 C37B-C34B = C33B-C36B = C32B-C35B = C7B-C4B = C6B-C3B = C2B-C5B
 2.77 with sigma of 0.005
 C35B-C37B = C32B-C34B = C5B-C7B = C4B-C2B
 2.41 with sigma of 0.005
 C32B-C36B = C33B-C35B = C2B-C6B = C3B-C5B
 2.41 with sigma of 0.005
 C6B-C4B = C7B-C3B = C36B-C34B = C37B-C33B
 2.41 with sigma of 0.005
 C36A-C32A = C35A-C33A = C6A-C2A = C5A-C3A
 2.41 with sigma of 0.005
 C36A-C33A = C37A-C34A = C35A-C32A = C6A-C3A = C7A-C4A = C2A-C5A
 2.77 with sigma of 0.005
 N41B-C42 \\sim N41A-C42 \\sim N11B-C12 \\sim N11A-C12
 with sigma of 0.01
 O40A-N41A \\sim O40B-N41B \\sim O10B-N11B \\sim O10A-N11A
 with sigma of 0.01
 C42-C43A \\sim C42-C43B \\sim C13B-C12 \\sim C13A-C12
 with sigma of 0.01
 O40A-C39A \\sim O40B-C39B \\sim O10B-C9B \\sim O10A-C9A
 with sigma of 0.01
 C43A-C39A \\sim C43B-C39B \\sim C13B-C9B \\sim C9A-C13A
 with sigma of 0.01
 C39A-C38A \\sim C39B-C38B \\sim C8B-C9B \\sim C9A-C8A
 with sigma of 0.01
 C38B-C35B \\sim C38A-C35A \\sim C8A-C5A \\sim C5B-C8B
 with sigma of 0.01
 C8A-C13A \\sim C8B-C13B \\sim C38A-C43A \\sim C43B-C38B
 with sigma of 0.02
 O40A-C38A \\sim C38B-O40B \\sim C8A-O10B \\sim C8B-O10A
 with sigma of 0.02
3. Restrained planarity
 C32B, C33B, C34B, C35B, C36B, C37B
 with sigma of 0.005
 C2B, C3B, C4B, C5B, C6B, C7B
 with sigma of 0.005
4. Uiso/Uaniso restraints and constraints
C42 \\sim C43A \\sim C39A \\sim O40A \\sim N41A \\sim C38A \\sim C35A \\sim
C36A \\sim C37A \\sim C32A \\sim C33A \\sim C34A \\sim F31A \\sim C42 \\sim
C43B \\sim C39B \\sim O40B \\sim N41B \\sim C38B \\sim C35B \\sim C34B \\sim
C33B \\sim C32B \\sim C37B \\sim C36B \\sim F31B: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08
C12 \\sim C13A \\sim C9A \\sim O10A \\sim N11A \\sim C8A \\sim C5A \\sim C4A
\\sim C3A \\sim C2A \\sim C7A \\sim C6A \\sim F1A \\sim C12 \\sim C13B \\sim
C9B \\sim O10B \\sim N11B \\sim C8B \\sim C5B \\sim C4B \\sim C3B \\sim C2B
\\sim C7B \\sim C6B \\sim F1B: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(N11A) = Uanis(N11B)
Uanis(O10B) = Uanis(O10A)
5. Rigid body (RIGU) restrains
 C42, C43A, C39A, O40A, N41A, C38A, C35A, C36A, C37A, C32A, C33A, C34A, F31A,
 C42, C43B, C39B, O40B, N41B, C38B, C35B, C34B, C33B, C32B, C37B, C36B, F31B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C12, C13A, C9A, O10A, N11A, C8A, C5A, C4A, C3A, C2A, C7A, C6A, F1A, C12, C13B,
  C9B, O10B, N11B, C8B, C5B, C4B, C3B, C2B, C7B, C6B, F1B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{F1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, O10A, N11A, C13A} sigma for 1-2:
0.01, 1-3: 0.02
as
{F1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B, C9B, O10B, N11B, C13B}
{F31A, C32A, C33A, C34A, C35A, C36A, C37A, C38A, C39A, O40A, N41A, C43A} sigma
for 1-2: 0.01, 1-3: 0.02
as
{F31B, C32B, C33B, C34B, C35B, C36B, C37B, C38B, C39B, O40B, N41B, C43B}
7. Others
 Sof(F31B)=Sof(C32B)=Sof(C33B)=Sof(H33B)=Sof(C34B)=Sof(H34B)=Sof(C35B)=
 Sof(C36B)=Sof(H36B)=Sof(C37B)=Sof(H37B)=Sof(C38B)=Sof(H38C)=Sof(H38D)=
 Sof(C39B)=Sof(H39B)=Sof(O40B)=Sof(N41B)=Sof(C43B)=Sof(H43C)=Sof(H43D)=1-FVAR(1)
 Sof(F31A)=Sof(C32A)=Sof(C33A)=Sof(H33A)=Sof(C34A)=Sof(H34A)=Sof(C35A)=
 Sof(C36A)=Sof(H36A)=Sof(C37A)=Sof(H37A)=Sof(C38A)=Sof(H38A)=Sof(H38B)=
 Sof(C39A)=Sof(H39A)=Sof(O40A)=Sof(N41A)=Sof(C43A)=Sof(H43A)=Sof(H43B)=FVAR(1)
 Sof(F1B)=Sof(C2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=Sof(C6B)=
 Sof(H6B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8BA)=Sof(H8BB)=Sof(C9B)=Sof(H9B)=
 Sof(O10B)=Sof(N11B)=Sof(C13B)=Sof(H13C)=Sof(H13D)=1-FVAR(2)
 Sof(F1A)=Sof(C2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(C6A)=
 Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C9A)=Sof(H9A)=
 Sof(O10A)=Sof(N11A)=Sof(C13A)=Sof(H13A)=Sof(H13B)=FVAR(2)
8.a Ternary CH refined with riding coordinates:
 C9A(H9A), C9B(H9B), C39A(H39A), C39B(H39B)
8.b Secondary CH2 refined with riding coordinates:
 C8A(H8AA,H8AB), C13A(H13A,H13B), C8B(H8BA,H8BB), C13B(H13C,H13D), C38A(H38A,
 H38B), C43A(H43A,H43B), C38B(H38C,H38D), C43B(H43C,H43D)
8.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C6A(H6A), C7A(H7A), C3B(H3B), C4B(H4B), C6B(H6B),
 C7B(H7B), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C33A(H33A), C34A(H34A), C36A(H36A), C37A(H37A), C33B(H33B), C34B(H34B),
 C36B(H36B), C37B(H37B), C45(H45), C47(H47), C48(H48), C49(H49), C50(H50),
 C52(H52), C53(H53)
;
_shelx_res_checksum              18635
_olex2_submission_special_instructions 'No special instructions were received'