TfOH-promoted synthesis of 4,5-dihydrooxazolo[5,4-<i>c</i>]isoquinolines <i>via</i> formal [3 + 2] cycloaddition of 4-diazoisoquinolin-3-one and benzonitriles.
Chen, Junrong; Li, Zhenmin; Suleman, Muhammad; Wang, Zaibin; Lu, Ping; Wang, Yanguang; Organic & biomolecular chemistry 18 (2020) 7671–7676; doi:10.1039/d0ob01748e

data_7157707
_publ_section_title
;
 TfOH-promoted synthesis of 4,5-dihydrooxazolo[5,4-<i>c</i>]isoquinolines
 <i>via</i> formal [3 + 2] cycloaddition of 4-diazoisoquinolin-3-one and
 benzonitriles.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7671
_journal_page_last               7676
_journal_paper_doi               10.1039/d0ob01748e
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C16 H9 Cl N2 O'
_chemical_formula_sum            'C16 H9 Cl N2 O'
_chemical_formula_weight         280.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-11 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.854(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.757(10)
_cell_length_b                   4.748(2)
_cell_length_c                   23.677(10)
_cell_measurement_reflns_used    6809
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.79
_cell_volume                     2472.8(18)
_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      170.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_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  0.0443
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18641
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.058
_diffrn_reflns_theta_min         2.778
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1587 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.9400.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0355P)^2^+2.6219P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4372
_reflns_number_total             5370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01748e2.cif
_cod_data_source_block           191224_cjr490177_1_c_0m
_cod_depositor_comments          'Adding full bibliography for 7157707.cif.'
_cod_original_cell_volume        2472.8(19)
_cod_database_code               7157707
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.868
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C23(H23), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32)
;
_shelx_res_checksum              94042
_shelx_hkl_checksum              443
_olex2_submission_special_instructions 'No special instructions were received'