#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/49/4514978.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_4514978
loop_
_publ_author_name
'Peterson, Joshua P.'
'Zhang, Rui'
'Winter, Arthur H.'
_publ_section_title
;
 Effect of Structure on the Spin Switching and Magnetic Bistability of
 Solid-State Aryl Dicyanomethyl Monoradicals and Diradicals.
;
_journal_issue                   8
_journal_name_full               'ACS omega'
_journal_page_first              13538
_journal_page_last               13542
_journal_paper_doi               10.1021/acsomega.9b01658
_journal_volume                  4
_journal_year                    2019
_chemical_formula_sum            'C20 H14 N4 S2'
_chemical_formula_weight         374.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 94.018(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9848(5)
_cell_length_b                   10.9219(7)
_cell_length_c                   10.4925(7)
_cell_measurement_reflns_used    7634
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      63.7394
_cell_measurement_theta_min      5.8552
_cell_volume                     912.79(10)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 Suite (Bruker AXS Inc. , 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX2 diffractometer'
_diffrn_measurement_method
'ω and φ scans, narrow frame width, shutterless'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12220
_diffrn_reflns_theta_full        63.73
_diffrn_reflns_theta_max         63.73
_diffrn_reflns_theta_min         5.86
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    2.726
_exptl_absorpt_correction_T_max  0.81
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;

SADABS (Spek A. L., 2015) was used for an absorption correction and scalling
of observed data
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.201
_refine_ls_extinction_coef       0.0038(8)
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0562P)²+0.2009P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                1366
_reflns_number_total             1483
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao9b01658_si_002.cif
_cod_data_source_block           Win015Cu
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-Scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4514978
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
S S1 0.25635(6) 0.54881(4) 0.62082(5) 0.0576(2) Uani d . . 1
C C1 0.44724(17) 0.01383(15) 0.56208(14) 0.0379(4) Uani d . . 1
C C2 0.55176(19) -0.03113(16) 0.67462(16) 0.0449(4) Uani d . . 1
C C3 0.29288(19) -0.06219(15) 0.54964(16) 0.0422(4) Uani d . . 1
C C4 0.40237(17) 0.14928(15) 0.57633(14) 0.0382(4) Uani d . . 1
C C5 0.24936(18) 0.19466(15) 0.52432(14) 0.0411(4) Uani d . . 1
H H5 0.173922 0.142483 0.479964 0.049 Uiso calc U R 1
C C6 0.20930(19) 0.31625(16) 0.53824(15) 0.0443(4) Uani d . . 1
H H6 0.106682 0.345443 0.503374 0.053 Uiso calc U R 1
C C7 0.3204(2) 0.39595(15) 0.60380(15) 0.0428(4) Uani d . . 1
C C8 0.4375(3) 0.62306(18) 0.69423(19) 0.0638(5) Uani d . . 1
H H8A 0.469534 0.583959 0.77419 0.096 Uiso calc U R 1
H H8B 0.412231 0.707601 0.708954 0.096 Uiso calc U R 1
H H8C 0.528125 0.61753 0.639026 0.096 Uiso calc U R 1
C C9 0.47371(19) 0.35033(17) 0.65424(16) 0.0484(4) Uani d . . 1
H H9 0.550143 0.402707 0.697268 0.058 Uiso calc U R 1
C C10 0.51353(19) 0.22864(16) 0.64119(15) 0.0467(4) Uani d . . 1
H H10 0.616026 0.199403 0.676253 0.056 Uiso calc U R 1
N N1 0.6358(2) -0.06626(18) 0.75804(16) 0.0693(5) Uani d . . 1
N N2 0.17274(19) -0.11816(15) 0.53802(16) 0.0575(4) Uani d . . 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_site_symmetry_3
_geom_angle
C7 S1 C8 . 104.03(9)
C2 C1 C3 . 107.62(13)
C2 C1 C4 . 111.40(13)
C3 C1 C4 . 110.51(12)
C2 C1 C1 3_656 106.38(14)
C3 C1 C1 3_656 107.39(15)
C4 C1 C1 3_656 113.26(15)
N1 C2 C1 . 177.70(17)
N2 C3 C1 . 178.20(18)
C10 C4 C5 . 118.94(15)
C10 C4 C1 . 120.41(13)
C5 C4 C1 . 120.65(13)
C6 C5 C4 . 120.36(14)
C6 C5 H5 . 119.8
C4 C5 H5 . 119.8
C5 C6 C7 . 120.79(14)
C5 C6 H6 . 119.6
C7 C6 H6 . 119.6
C6 C7 C9 . 118.55(15)
C6 C7 S1 . 117.69(12)
C9 C7 S1 . 123.75(13)
S1 C8 H8A . 109.5
S1 C8 H8B . 109.5
H8A C8 H8B . 109.5
S1 C8 H8C . 109.5
H8A C8 H8C . 109.5
H8B C8 H8C . 109.5
C10 C9 C7 . 120.76(15)
C10 C9 H9 . 119.6
C7 C9 H9 . 119.6
C9 C10 C4 . 120.60(15)
C9 C10 H10 . 119.7
C4 C10 H10 . 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C7 . 1.7589(17)
S1 C8 . 1.785(2)
C1 C2 . 1.481(2)
C1 C3 . 1.484(2)
C1 C4 . 1.532(2)
C1 C1 3_656 1.628(3)
C2 N1 . 1.132(2)
C3 N2 . 1.137(2)
C4 C10 . 1.385(2)
C4 C5 . 1.394(2)
C5 C6 . 1.376(2)
C5 H5 . 0.93
C6 C7 . 1.390(2)
C6 H6 . 0.93
C7 C9 . 1.392(2)
C8 H8A . 0.96
C8 H8B . 0.96
C8 H8C . 0.96
C9 C10 . 1.376(2)
C9 H9 . 0.93
C10 H10 . 0.93
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168345511
