Cyanomethylation and Cyclization of Aryl Alkynoates with Acetonitrile under Transition-Metal-Free Conditions: Synthesis of 3-Cyanomethylated Coumarins.
Yu, Yulan; Zhuang, Shengyi; Liu, Ping; Sun, Peipei; The Journal of organic chemistry 81 (2016) 11489–11495; doi:10.1021/acs.joc.6b02155

data_4037393
_publ_section_title
;
 Cyanomethylation and Cyclization of Aryl Alkynoates with Acetonitrile
 under Transition-Metal-Free Conditions: Synthesis of 3-Cyanomethylated
 Coumarins.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11489
_journal_page_last               11495
_journal_paper_doi               10.1021/acs.joc.6b02155
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C23 H15 N O2'
_chemical_formula_sum            'C23 H15 N O2'
_chemical_formula_weight         337.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.129(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.548(3)
_cell_length_b                   12.627(4)
_cell_length_c                   7.358(2)
_cell_measurement_reflns_used    4837
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.201
_cell_measurement_theta_min      2.257
_cell_volume                     838.1(4)
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5583
_diffrn_reflns_point_group_measured_fraction_full 0.835
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         1.613
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             352
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 944 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2463
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0249
_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^)+(0.0359P)^2^+0.1076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0654
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_full    0.672
_reflns_Friedel_fraction_max     0.672
_reflns_number_gt                2410
_reflns_number_total             2463
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02155_si_002.cif
_cod_data_source_block           spp-06
_cod_original_sg_symbol_H-M      'P  c '
_cod_database_code               4037393
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C14(H14), C23(H23), C19(H19), C11(H11), C22(H22), C7(H7),
 C9(H9), C8(H8), C20(H20), C21(H21), C10(H10)
;
_shelx_res_checksum              57439
_shelx_hkl_checksum              59012
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'