Iron(ii)-catalyzed C-2 cyanomethylation of indoles and pyrroles via direct oxidative cross-dehydrogenative coupling with acetonitrile derivatives
Qiao, Kai; Zhang, Dong; Zhang, Kai; Yuan, Xin; Zheng, Ming-Wei; Guo, Tian-Fo; Fang, Zheng; Wan, Li; Guo, Kai; Organic Chemistry Frontiers 5 (2018) 1129–; doi:10.1039/C7QO01086A

data_1553965
_publ_section_title
;
 Iron(ii)-catalyzed C-2 cyanomethylation of indoles and pyrroles via
 direct oxidative cross-dehydrogenative coupling with acetonitrile
 derivatives
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1129
_journal_paper_doi               10.1039/C7QO01086A
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C10 H8 N4'
_chemical_formula_weight         184.20
_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
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-09-12 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.442(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.3504(4)
_cell_length_b                   24.437(2)
_cell_length_c                   8.5476(7)
_cell_measurement_reflns_used    4455
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      2.50
_cell_volume                     887.36(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0563
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5901
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         3.495
_exptl_absorpt_coefficient_mu    0.089
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.165(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1551
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0492P)^2^+0.4365P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1186
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1419
_reflns_number_total             1551
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo01086a2.cif
_cod_data_source_block           20170906LMF_0m_a
_cod_original_cell_volume        887.35(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1553965
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              80031
_shelx_hkl_checksum              49849