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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/67/1556718.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_1556718
loop_
_publ_author_name
'Gärtner, Michael'
'Sauter, Eric'
'Nascimbeni, Giulia'
'Wiesner, Adrian'
'Kind, Martin'
'Werner, Philipp'
'Schuch, Christian'
'Abu-Husein, Tarek'
'Asyuda, Andika'
'Bats, Jan W.'
'Bolte, Michael'
'Zojer, Egbert'
'Terfort, Andreas'
'Zharnikov, Michael'
_publ_section_title
;
 Self-Assembled Monolayers with Distributed Dipole Moments Originating
 from Bipyrimidine Units
;
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_paper_doi               10.1021/acs.jpcc.9b08835
_journal_year                    2019
_chemical_formula_moiety         'C8 H6 N4 S'
_chemical_formula_sum            'C8 H6 N4 S'
_chemical_formula_weight         190.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                91.928(10)
_cell_angle_beta                 92.817(10)
_cell_angle_gamma                90.420(9)
_cell_formula_units_Z            2
_cell_length_a                   3.8332(4)
_cell_length_b                   10.1817(11)
_cell_length_c                   10.3930(13)
_cell_measurement_reflns_used    3681
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.76
_cell_volume                     404.89(8)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0291
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3681
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.897
_diffrn_reflns_theta_min         2.756
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       block
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0375
_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)+(0.0595P)²+0.1176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1022
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1425
_reflns_number_total             1579
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp9b08835_si_003.cif
_cod_data_source_block           te72
_cod_database_code               1556718
_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   0.950
_shelx_estimated_absorpt_t_max   0.966
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
S1 S 0.79920(12) 0.87122(4) 0.39895(5) 0.03312(19) Uani 1 1 d . .
H1 H 0.606(7) 0.946(3) 0.336(3) 0.060(8) Uiso 1 1 d . .
C1 C 0.6560(4) 0.71779(16) 0.33411(17) 0.0248(4) Uani 1 1 d . .
C2 C 0.7627(5) 0.60573(17) 0.39838(17) 0.0259(4) Uani 1 1 d . .
H2 H 0.9009 0.6163 0.4765 0.031 Uiso 1 1 calc R U
N3 N 0.6788(4) 0.48430(14) 0.35471(14) 0.0252(3) Uani 1 1 d . .
C4 C 0.4811(4) 0.47429(16) 0.24509(16) 0.0228(4) Uani 1 1 d . .
N5 N 0.3634(4) 0.57479(14) 0.17543(14) 0.0254(3) Uani 1 1 d . .
C6 C 0.4529(5) 0.69527(17) 0.22032(17) 0.0262(4) Uani 1 1 d . .
H6 H 0.3753 0.7686 0.1729 0.031 Uiso 1 1 calc R U
C11 C 0.3858(4) 0.33885(16) 0.19873(16) 0.0240(4) Uani 1 1 d . .
C12 C 0.4809(5) 0.23073(17) 0.27031(18) 0.0290(4) Uani 1 1 d . .
H12 H 0.6072 0.2451 0.3506 0.035 Uiso 1 1 calc R U
N13 N 0.4020(5) 0.10762(14) 0.23080(16) 0.0334(4) Uani 1 1 d . .
C14 C 0.2246(5) 0.09410(18) 0.11801(19) 0.0322(4) Uani 1 1 d . .
H14 H 0.1682 0.0066 0.0892 0.039 Uiso 1 1 calc R U
N15 N 0.1170(4) 0.18817(15) 0.04090(16) 0.0328(4) Uani 1 1 d . .
C16 C 0.1991(5) 0.31138(17) 0.08235(18) 0.0276(4) Uani 1 1 d . .
H16 H 0.1274 0.3823 0.0305 0.033 Uiso 1 1 calc R U
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'
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
C1 S1 H1 100.6(13)
C6 C1 C2 115.68(15)
C6 C1 S1 126.27(13)
C2 C1 S1 118.00(13)
N3 C2 C1 122.75(16)
N3 C2 H2 118.6
C1 C2 H2 118.6
C2 N3 C4 116.49(15)
N3 C4 N5 125.91(16)
N3 C4 C11 115.88(15)
N5 C4 C11 118.21(15)
C6 N5 C4 116.58(15)
N5 C6 C1 122.59(16)
N5 C6 H6 118.7
C1 C6 H6 118.7
C12 C11 C16 115.95(16)
C12 C11 C4 121.14(16)
C16 C11 C4 122.91(15)
N13 C12 C11 122.61(17)
N13 C12 H12 118.7
C11 C12 H12 118.7
C14 N13 C12 115.78(16)
N15 C14 N13 127.69(17)
N15 C14 H14 116.2
N13 C14 H14 116.2
C14 N15 C16 115.62(16)
N15 C16 C11 122.33(16)
N15 C16 H16 118.8
C11 C16 H16 118.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7539(17)
S1 H1 1.25(3)
C1 C6 1.395(3)
C1 C2 1.395(2)
C2 N3 1.334(2)
C2 H2 0.9500
N3 C4 1.338(2)
C4 N5 1.341(2)
C4 C11 1.482(2)
N5 C6 1.334(2)
C6 H6 0.9500
C11 C12 1.390(2)
C11 C16 1.394(2)
C12 N13 1.334(2)
C12 H12 0.9500
N13 C14 1.328(3)
C14 N15 1.325(2)
C14 H14 0.9500
N15 C16 1.343(2)
C16 H16 0.9500
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 H1 N13 1.25(3) 2.14(3) 3.3528(17) 164(2) 1_565
C2 H2 N3 0.95 2.57 3.414(2) 148.6 2_766
C14 H14 N15 0.95 2.57 3.481(2) 160.9 2
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
C6 C1 C2 N3 0.2(3)
S1 C1 C2 N3 -177.56(13)
C1 C2 N3 C4 -0.6(3)
C2 N3 C4 N5 0.6(3)
C2 N3 C4 C11 -179.17(14)
N3 C4 N5 C6 0.0(3)
C11 C4 N5 C6 179.71(14)
C4 N5 C6 C1 -0.5(3)
C2 C1 C6 N5 0.4(3)
S1 C1 C6 N5 177.93(13)
N3 C4 C11 C12 3.7(3)
N5 C4 C11 C12 -176.02(16)
N3 C4 C11 C16 -176.04(16)
N5 C4 C11 C16 4.2(3)
C16 C11 C12 N13 0.4(3)
C4 C11 C12 N13 -179.40(16)
C11 C12 N13 C14 -0.1(3)
C12 N13 C14 N15 -0.2(3)
N13 C14 N15 C16 0.2(3)
C14 N15 C16 C11 0.1(3)
C12 C11 C16 N15 -0.4(3)
C4 C11 C16 N15 179.41(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168305910
