Synthetic access to isoxazoline-functionalized isoquinolines via microwave-assisted iminoxyl radical-participated cascade cyclization of vinyl isocyanides.
Xu, Yulong; Chen, Hao; Li, Wei; Xie, Qiong; Yu, Linqian; Shao, Liming; Organic & biomolecular chemistry 16 (2018) 4996–5005; doi:10.1039/c8ob01229f

data_7156286
_publ_section_title
;
 Synthetic access to isoxazoline-functionalized isoquinolines via
 microwave-assisted iminoxyl radical-participated cascade cyclization of
 vinyl isocyanides.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4996
_journal_page_last               5005
_journal_paper_doi               10.1039/c8ob01229f
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C29 H26 N2 O3'
_chemical_formula_sum            'C29 H26 N2 O3'
_chemical_formula_weight         450.52
_chemical_name_systematic
'Methyl 1-((4,4-dimethyl-3-phenyl-4,5-dihydroisoxazol-5-yl)methyl)-4-phenylisoquinoline-3-carboxylate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-05-24 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.1449(2)
_cell_length_b                   11.6133(3)
_cell_length_c                   40.0056(9)
_cell_measurement_reflns_used    8471
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      69.81
_cell_measurement_theta_min      3.314
_cell_volume                     4713.29(19)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      301.85
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            29650
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.084
_diffrn_reflns_theta_min         4.888
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1376 before and 0.0701 after correction. The Ratio of minimum to maximum transmission is 0.6955. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'white solid'
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0685P)^2^+1.5826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1408
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3452
_reflns_number_total             4456
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01229f2.cif
_cod_data_source_block           cu_d8v17115_0m
_cod_depositor_comments          'Adding full bibliography for 7156286.cif.'
_cod_database_code               7156286
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.827
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17),
 C18(H18), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              9588
_olex2_submission_special_instructions 'No special instructions were received'