Preparation of isoquinazolines via metal-free [4 + 2] cycloaddition of ynamides with nitriles.
Wu, Hao; Liu, Yu; He, Ming-Xing; Wen, Hao; Cao, Wei; Chen, Ping; Tang, Yu; Organic & biomolecular chemistry 17 (2019) 8408–8416; doi:10.1039/c9ob01395d

data_7157060
_publ_section_title
;
 Preparation of isoquinazolines via metal-free [4 + 2] cycloaddition of
 ynamides with nitriles.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8408
_journal_page_last               8416
_journal_paper_doi               10.1039/c9ob01395d
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C26 H24 Cl2 N2 O2 S'
_chemical_formula_sum            'C26 H24 Cl2 N2 O2 S'
_chemical_formula_weight         499.43
_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
_atom_sites_solution_primary     dual
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_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_audit_update_record
;
2019-03-21 deposited with the CCDC.    2019-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                95.3140(10)
_cell_angle_beta                 106.9550(10)
_cell_angle_gamma                109.2400(10)
_cell_formula_units_Z            2
_cell_length_a                   8.7442(10)
_cell_length_b                   11.0021(12)
_cell_length_c                   14.9590(16)
_cell_measurement_reflns_used    2960
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      25.464
_cell_measurement_theta_min      2.217
_cell_volume                     1271.0(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      273.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10247
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.614
_diffrn_reflns_theta_min         2.529
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0443 before and 0.0314 after correction. The Ratio of minimum to maximum transmission is 0.9366. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_refine_diff_density_max         0.239
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_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0527P)^2^+0.2304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3814
_reflns_number_total             5439
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {5b5c0f8f-f80e-4d53-b4ae-c3a09ddea0bd}
_cod_data_source_file            c9ob01395d2.cif
_cod_data_source_block           181029wh_0m
_cod_depositor_comments          'Adding full bibliography for 7157060.cif.'
_cod_database_code               7157060
_shelx_shelxl_version_number     2018/3
_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.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C)
;
_shelx_res_checksum              61708
_shelx_hkl_checksum              98807
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
;
;