data_A
 
_publ_contact_author_name         'U. Schilde'
_publ_contact_author_address
;
 University of Potsdam
 Institute of Chemistry
 Karl-Liebknecht-Strasse 24-25
 D-14476 Potsdam
 Germany
;

_publ_contact_author_email        'us@chem.uni-potsdam.de'
_publ_contact_author_phone        '+49 331 977-5188'
_publ_contact_author_fax          '+49 331 977-5239'

loop_
 _publ_author_name
 _publ_author_address
     'Sardarian, A. R.'
;     Shiraz University
      College of Sciences
      Chemistry Department
      Shiraz 71946 84795
      Iran
;
     'Inaloo, I. D.'
;     Shiraz University
      College of Sciences
      Chemistry Department
      Shiraz 71946 84795
      Iran
;
     'Modarresi-Alam, A. R.'
;     University of Sistan and Baluchestan
      College of Sciences 
      Department of Chemistry
      Zahedan
      Iran
;
     'Kleinpeter, E.'
;     Universität Potsdam
      Institut für Chemie
      Karl-Liebknecht-Strasse 24-25
      D-14476 Potsdam
      Germany
;
     'Schilde, U.'
;     Universität Potsdam
      Institut für Chemie
      Karl-Liebknecht-Strasse 24-25
      D-14476 Potsdam
      Germany
;

_publ_requested_journal
;
 Journal of Organic Chemistry
;
_publ_section_title
;
 Metal-free regioselective mono cyanation of hydroxy-, alkoxy- and
 benzyloxy arenes by potassium thiocyanate and silica sulfuric acid
 as a new cyanating agent
; 

_audit_creation_method            'SHELXL-2014/7'
_chemical_name_systematic
;
 4-hydroxy-2-methylbenzonitrile
;
_chemical_formula_sum             'C8 H7 N O' 
_chemical_formula_weight          133.15

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            15
_space_group_name_H-M_alt         'C 2/c'
_space_group_name_Hall            '-C 2yc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    13.0140(19)
_cell_length_b                    6.9530(6)
_cell_length_c                    14.952(2)
_cell_angle_alpha                 90
_cell_angle_beta                  95.305(12)
_cell_angle_gamma                 90
_cell_volume                      1347.2(3)
_cell_formula_units_Z             8
_cell_measurement_temperature     210(2)
_cell_measurement_reflns_used     9040
_cell_measurement_theta_min       2.72
_cell_measurement_theta_max       29.45
 
_exptl_crystal_description        block
_exptl_crystal_colour             colorless
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.313          
_exptl_crystal_F_000              560
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.80
_exptl_crystal_size_mid           0.49
_exptl_crystal_size_min           0.30
_exptl_crystal_size_rad            0.30
_exptl_absorpt_coefficient_mu     0.088
_exptl_absorpt_correction_type    sphere
_exptl_absorpt_correction_T_min   0.9621
_exptl_absorpt_correction_T_max   0.9624
_exptl_absorpt_process_details    'X-RED (Stoe, 2011)'

_diffrn_ambient_temperature       210(2)
_diffrn_measurement_device        '2-circle goniometer'
_diffrn_measurement_device_type   'STOE IPDS 2'
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_type            'Mo K\a'
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_monochromator   'plane graphite'
_diffrn_detector                  'image plate (34 cm diameter)'
_diffrn_detector_type             'STOE'
_diffrn_detector_area_resol_mean  6.67
_diffrn_measurement_method        'ω scan, δ ω = 1.0 deg'
_diffrn_measurement_details
; 
 180 frames, 3 min exposure time
;
_diffrn_reflns_number             4142
_diffrn_reflns_av_unetI/netI      0.0190
_diffrn_reflns_av_R_equivalents   0.0295
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          3.144
_diffrn_reflns_theta_max          24.991
_diffrn_reflns_theta_full         24.991
_diffrn_measured_fraction_theta_max   0.995
_diffrn_measured_fraction_theta_full  0.995
_diffrn_reflns_Laue_measured_fraction_max    0.995
_diffrn_reflns_Laue_measured_fraction_full   0.995
_diffrn_reflns_point_group_measured_fraction_max   0.995
_diffrn_reflns_point_group_measured_fraction_full  0.995

_reflns_number_total              1184
_reflns_number_gt                 1037
_reflns_threshold_expression      'I > 2σ(I)'
 
_computing_data_collection        'X-AREA (Stoe, 2015)'
_computing_cell_refinement        'X-AREA (Stoe, 2015)'
_computing_data_reduction         'X-RED (Stoe, 2015)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material
; 
 SHELXL-2014/7 (Sheldrick, 2014)
 Diamond (Blankenburg, 2017)
;

_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0556P)²+0.3288P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    difmap
_refine_ls_hydrogen_treatment     refall
_refine_ls_extinction_method      'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef        0.020(5)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          1184
_refine_ls_number_parameters      120
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0363
_refine_ls_R_factor_gt            0.0318
_refine_ls_wR_factor_ref          0.0941
_refine_ls_wR_factor_gt           0.0915
_refine_ls_goodness_of_fit_ref    1.081
_refine_ls_restrained_S_all       1.081
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.86759(8) 0.50174(18) 0.45600(7) 0.0333(3) Uani 1 1 d . . . . .
C2 C 0.88582(8) 0.30830(18) 0.43532(8) 0.0343(3) Uani 1 1 d . . . . .
C3 C 0.89005(9) 0.17633(18) 0.50458(8) 0.0359(3) Uani 1 1 d . . . . .
H3 H 0.8995(10) 0.042(2) 0.4915(9) 0.044(4) Uiso 1 1 d . . . . .
C4 C 0.87669(8) 0.23165(18) 0.59203(8) 0.0355(3) Uani 1 1 d . . . . .
C5 C 0.86004(9) 0.42383(18) 0.61213(8) 0.0371(3) Uani 1 1 d . . . . .
H5 H 0.8498(9) 0.459(2) 0.6755(10) 0.040(3) Uiso 1 1 d . . . . .
C6 C 0.85551(9) 0.55837(18) 0.54407(8) 0.0361(3) Uani 1 1 d . . . . .
H6 H 0.8444(10) 0.698(2) 0.5572(9) 0.043(3) Uiso 1 1 d . . . . .
C7 C 0.86059(9) 0.64109(18) 0.38519(8) 0.0373(3) Uani 1 1 d . . . . .
C8 C 0.89996(12) 0.2471(2) 0.34097(9) 0.0447(4) Uani 1 1 d . . . . .
H8A H 0.9439(15) 0.340(3) 0.3125(13) 0.084(6) Uiso 1 1 d . . . . .
H8B H 0.9249(16) 0.122(4) 0.3384(15) 0.101(7) Uiso 1 1 d . . . . .
H8C H 0.8341(14) 0.245(3) 0.3038(14) 0.081(6) Uiso 1 1 d . . . . .
N1 N 0.85437(9) 0.74868(17) 0.32667(7) 0.0480(3) Uani 1 1 d . . . . .
O1 O 0.88006(7) 0.09024(14) 0.65496(6) 0.0467(3) Uani 1 1 d . . . . .
H1 H 0.8706(13) 0.145(3) 0.7113(13) 0.077(6) Uiso 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 C6 1.3973(16) . ?
C1 C2 1.4052(18) . ?
C1 C7 1.4318(17) . ?
C2 C3 1.3809(18) . ?
C2 C8 1.5010(17) . ?
C3 C4 1.3891(17) . ?
C3 H3 0.962(15) . ?
C4 O1 1.3588(15) . ?
C4 C5 1.3910(18) . ?
C5 C6 1.3795(18) . ?
C5 H5 0.999(14) . ?
C6 H6 1.004(16) . ?
C7 N1 1.1484(16) . ?
C8 H8A 0.99(2) . ?
C8 H8B 0.93(3) . ?
C8 H8C 0.978(18) . ?
O1 H1 0.94(2) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C6 C1 C2 120.87(11) . . ?
C6 C1 C7 120.08(11) . . ?
C2 C1 C7 119.05(10) . . ?
C3 C2 C1 117.83(11) . . ?
C3 C2 C8 121.11(12) . . ?
C1 C2 C8 121.06(11) . . ?
C2 C3 C4 121.48(12) . . ?
C2 C3 H3 119.2(9) . . ?
C4 C3 H3 119.2(8) . . ?
O1 C4 C3 116.91(11) . . ?
O1 C4 C5 122.76(11) . . ?
C3 C4 C5 120.33(11) . . ?
C6 C5 C4 119.27(11) . . ?
C6 C5 H5 122.3(8) . . ?
C4 C5 H5 118.4(8) . . ?
C5 C6 C1 120.22(12) . . ?
C5 C6 H6 120.6(8) . . ?
C1 C6 H6 119.2(8) . . ?
N1 C7 C1 178.04(13) . . ?
C2 C8 H8A 110.3(12) . . ?
C2 C8 H8B 112.2(14) . . ?
H8A C8 H8B 112.1(18) . . ?
C2 C8 H8C 111.2(12) . . ?
H8A C8 H8C 106.2(16) . . ?
H8B C8 H8C 104.5(17) . . ?
C4 O1 H1 109.0(12) . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C6 C1 C2 C3 0.81(16) . . . . ?
C7 C1 C2 C3 -178.66(10) . . . . ?
C6 C1 C2 C8 -179.35(11) . . . . ?
C7 C1 C2 C8 1.18(17) . . . . ?
C1 C2 C3 C4 0.06(17) . . . . ?
C8 C2 C3 C4 -179.78(11) . . . . ?
C2 C3 C4 O1 178.63(10) . . . . ?
C2 C3 C4 C5 -0.93(17) . . . . ?
O1 C4 C5 C6 -178.63(10) . . . . ?
C3 C4 C5 C6 0.90(18) . . . . ?
C4 C5 C6 C1 -0.03(17) . . . . ?
C2 C1 C6 C5 -0.84(16) . . . . ?
C7 C1 C6 C5 178.63(11) . . . . ?
 
loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
C5 H5 N1  0.999(14) 2.677(14) 3.4319(17) 132.5(10) 6_566
O1 H1 N1  0.94(2) 1.91(2) 2.8490(15) 178.3(17) 6_566
 
_refine_diff_density_max    0.155
_refine_diff_density_min   -0.164
_refine_diff_density_rms    0.027





