Metal-Free Regioselective Monocyanation of Hydroxy-, Alkoxy-, and Benzyloxyarenes by Potassium Thiocyanate and Silica Sulfuric Acid as a Cyanating Agent.
Sardarian, Ali Reza; Dindarloo Inaloo, Iman; Modarresi-Alam, Ali Reza; Kleinpeter, Erich; Schilde, Uwe; The Journal of organic chemistry 84 (2019) 1748–1756; doi:10.1021/acs.joc.8b02191

data_4033750
_publ_section_title
;
 Metal-Free Regioselective Monocyanation of Hydroxy-, Alkoxy-, and
 Benzyloxyarenes by Potassium Thiocyanate and Silica Sulfuric Acid as a
 Cyanating Agent.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1748
_journal_page_last               1756
_journal_paper_doi               10.1021/acs.joc.8b02191
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C8 H7 N O'
_chemical_formula_weight         133.15
_chemical_name_systematic
;
 4-hydroxy-2-methylbenzonitrile
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.305(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.0140(19)
_cell_length_b                   6.9530(6)
_cell_length_c                   14.952(2)
_cell_measurement_reflns_used    9040
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      29.45
_cell_measurement_theta_min      2.72
_cell_volume                     1347.2(3)
_computing_cell_refinement       'X-AREA (Stoe, 2015)'
_computing_data_collection       'X-AREA (Stoe, 2015)'
_computing_data_reduction        'X-RED (Stoe, 2015)'
_computing_publication_material
; 
 SHELXL-2014/7 (Sheldrick, 2014)
 Diamond (Blankenburg, 2017)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      210(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
; 
 180 frames, 3 min exposure time
;
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       '\w scan, \d \w = 1.0 deg'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4142
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         3.144
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9624
_exptl_absorpt_correction_T_min  0.9621
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'X-RED (Stoe, 2011)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.30
_exptl_crystal_size_rad          0.30
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.020(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0556P)^2^+0.3288P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0941
_reflns_number_gt                1037
_reflns_number_total             1184
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02191_si_001.cif
_cod_data_source_block           A
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4033750
_shelx_res_checksum              85127
_shelx_hkl_checksum              93143