Direct synthesis of 2-substituted benzonitriles via alkylcyanation of arynes with N,N-disubstituted aminomalononitriles.
Bao, Wen; Gao, Zhu-Peng; Jin, Da-Ping; Xue, Cao-Gen; Liang, Huan; Lei, Ling-Sheng; Xu, Xue-Tao; Zhang, Kun; Wang, Shao-Hua; Chemical communications (Cambridge, England) 56 (2020) 7641–7644; doi:10.1039/d0cc01591a

data_7126675
_publ_section_title
;
 Direct synthesis of 2-substituted benzonitriles via alkylcyanation of
 arynes with N,N-disubstituted aminomalononitriles.
;
_journal_issue                   55
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7641
_journal_page_last               7644
_journal_paper_doi               10.1039/d0cc01591a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C18 H15 N3 O'
_chemical_formula_sum            'C18 H15 N3 O'
_chemical_formula_weight         289.33
_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     direct
_audit_creation_date             2019-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-19 deposited with the CCDC.	2020-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.520(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2780(4)
_cell_length_b                   23.2807(7)
_cell_length_c                   7.4089(3)
_cell_measurement_reflns_used    2267
_cell_measurement_temperature    292.77(10)
_cell_measurement_theta_max      69.6450
_cell_measurement_theta_min      8.9480
_cell_volume                     1562.26(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      292.77(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
  1 omega  -31.00   11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -38.0000  120.0000 42

  2 omega  -75.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -90.0000 40

  3 omega  -80.00  -54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -38.0000  120.0000 26

  4 omega   45.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000   90.0000 33

  5 omega   -9.00   38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000   90.0000 47

  6 omega   67.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 28

  7 omega  -14.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   30.0000 89

  8 omega   45.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 27

  9 omega   57.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 36

 10 omega   36.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 29

 11 omega   36.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 55

 12 omega  107.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   60.0000 44

 13 omega   38.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 57

 14 omega   37.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 42

 15 omega   46.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 28

 16 omega   53.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   30.0000 70

 17 omega   37.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 56

 18 omega   54.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   90.0000 33

 19 omega   44.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 25

 20 omega   74.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1634652000
_diffrn_orient_matrix_UB_12      0.0180680000
_diffrn_orient_matrix_UB_13      -0.0546447000
_diffrn_orient_matrix_UB_21      0.0135938000
_diffrn_orient_matrix_UB_22      0.0067006000
_diffrn_orient_matrix_UB_23      -0.2025816000
_diffrn_orient_matrix_UB_31      -0.0452365000
_diffrn_orient_matrix_UB_32      -0.0632539000
_diffrn_orient_matrix_UB_33      -0.0370776000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5181
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         3.797
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0724P)^2^+0.2012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1337
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2277
_reflns_number_total             2690
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01591a3.cif
_cod_data_source_block           baow1_0717
_cod_depositor_comments
'Adding full bibliography for 7126672--7126675.cif.'
_cod_original_cell_volume        1562.25(10)
_cod_database_code               7126675
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 96.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C12(H12), C14(H14), C18(H18), C20(H20), C22(H22)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              24950
_shelx_hkl_checksum              99808
_olex2_submission_special_instructions 'No special instructions were received'