#------------------------------------------------------------------------------
#$Date: 2020-10-04 05:42:14 +0300 (Sun, 04 Oct 2020) $
#$Revision: 256985 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/79/4517971.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4517971
loop_
_publ_author_name
'Werner, Philipp'
'Wächter, Tobias'
'Asyuda, Andika'
'Wiesner, Adrian'
'Kind, Martin'
'Bolte, Michael'
'Weinhardt, Lothar'
'Terfort, Andreas'
'Zharnikov, Michael'
_publ_section_title
;
 Electron Transfer Dynamics and Structural Effects in Benzonitrile
 Monolayers with Tuned Dipole Moments by Differently Positioned Fluorine
 Atoms.
;
_journal_issue                   35
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              39859
_journal_page_last               39869
_journal_paper_doi               10.1021/acsami.0c10513
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         'C7 H3 F2 N S'
_chemical_formula_sum            'C7 H3 F2 N S'
_chemical_formula_weight         171.16
_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   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 115.779(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3939(14)
_cell_length_b                   14.805(3)
_cell_length_c                   6.9469(12)
_cell_measurement_reflns_used    3203
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.75
_cell_measurement_theta_min      3.36
_cell_volume                     684.8(2)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3203
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.662
_diffrn_reflns_theta_min         3.633
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     53
_refine_ls_number_reflns         651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0399
_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/[σ²(Fo²)+(0.0590P)²+0.7025P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1130
_reflns_Friedel_coverage         0.000
_reflns_number_gt                598
_reflns_number_total             651
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am0c10513_si_005.cif
_cod_data_source_block           te76
_cod_depositor_comments
;Adding full bibliography for 4517969--4517972.cif.

 Adding full bibliography for 4517969--4517972.cif.
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4517971
_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. 
;
_shelx_estimated_absorpt_t_min   0.915
_shelx_estimated_absorpt_t_max   0.950
_shelxl_version_number           2014/6
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'
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
S1 S 0.0000 0.93223(6) 0.2500 0.0352(3) Uani 1 2 d S T P . .
H1A H 0.1208 0.9380 0.1975 0.053 Uiso 0.25 1 d R U P . .
H1B H 0.1032 0.9682 0.3696 0.053 Uiso 0.25 1 d R U P . .
F1 F 0.29092(19) 0.62802(9) 0.1948(2) 0.0341(4) Uani 1 1 d . . . . .
N1 N 0.0000 0.44906(19) 0.2500 0.0344(7) Uani 1 2 d S T P . .
C1 C 0.0000 0.8140(2) 0.2500 0.0270(7) Uani 1 2 d S T P . .
C2 C 0.1497(3) 0.76646(16) 0.2193(3) 0.0269(5) Uani 1 1 d . . . . .
H2 H 0.2514 0.7979 0.1979 0.032 Uiso 1 1 calc R U . . .
C3 C 0.1464(3) 0.67415(16) 0.2208(3) 0.0249(5) Uani 1 1 d . . . . .
C4 C 0.0000 0.6238(2) 0.2500 0.0252(7) Uani 1 2 d S T P . .
C5 C 0.0000 0.5273(2) 0.2500 0.0278(7) Uani 1 2 d S T P . .
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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C1 S1 H1A 94.4 . . ?
C1 S1 H1B 122.1 . . ?
H1A S1 H1B 78.4 . . ?
C2 C1 C2 119.8(3) 2 . ?
C2 C1 S1 120.09(15) 2 . ?
C2 C1 S1 120.09(15) . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
F1 C3 C2 119.26(19) . . ?
F1 C3 C4 117.3(2) . . ?
C2 C3 C4 123.4(2) . . ?
C3 C4 C3 115.6(3) . 2 ?
C3 C4 C5 122.19(14) . . ?
C3 C4 C5 122.19(14) 2 . ?
N1 C5 C4 180.0 . . ?
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
S1 C1 1.751(3) . ?
S1 H1A 1.1052 . ?
S1 H1B 1.0022 . ?
F1 C3 1.345(2) . ?
N1 C5 1.158(4) . ?
C1 C2 1.404(3) 2 ?
C1 C2 1.404(3) . ?
C2 C3 1.367(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(3) . ?
C4 C3 1.400(3) 2 ?
C4 C5 1.429(5) . ?
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
S1 H1B F1 1.00 2.59 3.2286(16) 121.3 4
S1 H1A N1 1.11 2.67 3.7053(7) 155.6 3
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
C2 C1 C2 C3 -0.22(13) 2 . . . ?
S1 C1 C2 C3 179.78(13) . . . . ?
C1 C2 C3 F1 -178.99(15) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
F1 C3 C4 C3 179.2(2) . . . 2 ?
C2 C3 C4 C3 -0.24(14) . . . 2 ?
F1 C3 C4 C5 -0.8(2) . . . . ?
C2 C3 C4 C5 179.76(14) . . . . ?
