#------------------------------------------------------------------------------
#$Date: 2023-05-16 01:59:24 +0300 (Tue, 16 May 2023) $
#$Revision: 283793 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/30/7713025.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_7713025
loop_
_publ_author_name
'Trang, Christina D. M.'
'Saal, Thomas'
'Inkpen , Michael Stephen'
_publ_section_title
;
 Methyldisulfide groups enable the direct connection of air-stable metal
 bis(terpyridine) complexes to gold surfaces
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT00955F
_journal_year                    2023
_chemical_formula_moiety         'C16 H13 N3 S2'
_chemical_formula_sum            'C16 H13 N3 S2'
_chemical_formula_weight         311.41
_chemical_name_common            tpySS
_chemical_name_systematic        4?-(methyldisulfide)-2,2?:6?,2??-terpyridine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2022-11-18 deposited with the CCDC.	2023-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.1950(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8399(2)
_cell_length_b                   15.3680(3)
_cell_length_c                   10.8169(2)
_cell_measurement_reflns_used    123
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      37.8208
_cell_measurement_theta_min      8.4253
_cell_volume                     1460.91(5)
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS, 2014)'
_computing_data_collection
'Bruker Instrument Service v2012.12.0.3 (Bruker AXS, 2012'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_refinement  'SHELXTL XL 2014/7 (Bruker AXS, 2014)'
_computing_structure_solution    'SHELXTL XT 2014/4 (Bruker AXS, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_radiation_type           'CuK\a '
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23417
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         70.13
_diffrn_reflns_theta_min         5.02
_diffrn_source                   'IuS microsource'
_exptl_absorpt_coefficient_mu    3.260
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5 (Bruker AXS)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.366
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0289
_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)+(0.0420P)²+0.8770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0817
_reflns_number_gt                2572
_reflns_number_total             2773
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt00955f2.cif
_cod_data_source_block           C16H13N3S2
_cod_database_code               7713025
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.30686(4) 0.34888(2) 0.96071(3) 0.01940(12) Uani d . . . 1 . .
N N1 0.79213(16) 0.20417(9) 0.80764(12) 0.0244(3) Uani d . . . 1 . .
C C1 0.9357(2) 0.17525(12) 0.81685(16) 0.0291(4) Uani d . . . 1 . .
H H1 0.9694 0.1385 0.885 0.035 Uiso calc U . R 1 . .
S S2 0.13829(4) 0.43912(3) 0.93292(4) 0.02319(12) Uani d . . . 1 . .
N N2 0.53198(14) 0.33019(8) 0.60116(11) 0.0139(3) Uani d . . . 1 . .
C C2 1.03814(19) 0.19562(11) 0.73305(17) 0.0263(4) Uani d . . . 1 . .
H H2 1.1403 0.1756 0.7455 0.032 Uiso calc U . R 1 . .
N N3 0.20601(14) 0.45834(8) 0.48334(12) 0.0166(3) Uani d . . . 1 . .
C C3 0.98813(18) 0.24588(10) 0.63074(16) 0.0223(3) Uani d . . . 1 . .
H H3 1.0548 0.2599 0.5704 0.027 Uiso calc U . R 1 . .
C C4 0.83855(17) 0.27554(10) 0.61757(14) 0.0177(3) Uani d . . . 1 . .
H H4 0.8004 0.3091 0.5472 0.021 Uiso calc U . R 1 . .
C C5 0.74595(17) 0.25501(9) 0.70971(13) 0.0161(3) Uani d . . . 1 . .
C C6 0.59178(16) 0.29399(9) 0.70842(14) 0.0146(3) Uani d . . . 1 . .
C C7 0.52231(17) 0.29754(9) 0.81798(14) 0.0161(3) Uani d . . . 1 . .
H H7 0.5675 0.2705 0.8919 0.019 Uiso calc U . R 1 . .
C C8 0.38487(17) 0.34183(9) 0.81600(14) 0.0158(3) Uani d . . . 1 . .
C C9 0.32142(16) 0.38002(9) 0.70658(14) 0.0157(3) Uani d . . . 1 . .
H H9 0.2274 0.4103 0.7032 0.019 Uiso calc U . R 1 . .
C C10 0.39934(16) 0.37286(9) 0.60119(14) 0.0141(3) Uani d . . . 1 . .
C C11 0.34102(16) 0.41775(9) 0.48344(14) 0.0144(3) Uani d . . . 1 . .
C C12 0.42590(16) 0.41943(9) 0.38180(14) 0.0155(3) Uani d . . . 1 . .
H H12 0.5205 0.3898 0.3846 0.019 Uiso calc U . R 1 . .
C C13 0.36879(18) 0.46543(10) 0.27663(14) 0.0185(3) Uani d . . . 1 . .
H H13 0.4236 0.4674 0.2058 0.022 Uiso calc U . R 1 . .
C C14 0.23080(18) 0.50852(10) 0.27604(14) 0.0194(3) Uani d . . . 1 . .
H H14 0.1899 0.541 0.2055 0.023 Uiso calc U . R 1 . .
C C15 0.15406(17) 0.50285(10) 0.38110(15) 0.0189(3) Uani d . . . 1 . .
H H15 0.0594 0.5322 0.3804 0.023 Uiso calc U . R 1 . .
C C16 0.2445(2) 0.53943(11) 0.93333(17) 0.0275(4) Uani d . . . 1 . .
H H16A 0.1754 0.5888 0.939 0.041 Uiso calc U . R 1 . .
H H16B 0.2932 0.5439 0.8564 0.041 Uiso calc U . R 1 . .
H H16C 0.3227 0.5401 1.0049 0.041 Uiso calc U . R 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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 S1 S2 . . 104.99(5) ?
C1 N1 C5 . . 117.17(14) ?
N1 C1 C2 . . 123.93(16) ?
N1 C1 H1 . . 118.0 ?
C2 C1 H1 . . 118.0 ?
C16 S2 S1 . . 102.07(6) ?
C6 N2 C10 . . 117.67(13) ?
C3 C2 C1 . . 118.38(15) ?
C3 C2 H2 . . 120.8 ?
C1 C2 H2 . . 120.8 ?
C15 N3 C11 . . 117.54(13) ?
C2 C3 C4 . . 118.90(15) ?
C2 C3 H3 . . 120.6 ?
C4 C3 H3 . . 120.6 ?
C3 C4 C5 . . 118.56(14) ?
C3 C4 H4 . . 120.7 ?
C5 C4 H4 . . 120.7 ?
N1 C5 C4 . . 122.95(14) ?
N1 C5 C6 . . 116.21(13) ?
C4 C5 C6 . . 120.72(13) ?
N2 C6 C7 . . 123.37(13) ?
N2 C6 C5 . . 116.74(13) ?
C7 C6 C5 . . 119.69(13) ?
C8 C7 C6 . . 118.07(14) ?
C8 C7 H7 . . 121.0 ?
C6 C7 H7 . . 121.0 ?
C9 C8 C7 . . 119.56(14) ?
C9 C8 S1 . . 124.48(11) ?
C7 C8 S1 . . 115.90(11) ?
C8 C9 C10 . . 118.28(13) ?
C8 C9 H9 . . 120.9 ?
C10 C9 H9 . . 120.9 ?
N2 C10 C9 . . 123.04(13) ?
N2 C10 C11 . . 116.55(13) ?
C9 C10 C11 . . 120.32(13) ?
N3 C11 C12 . . 122.84(13) ?
N3 C11 C10 . . 116.09(13) ?
C12 C11 C10 . . 121.04(13) ?
C13 C12 C11 . . 118.43(14) ?
C13 C12 H12 . . 120.8 ?
C11 C12 H12 . . 120.8 ?
C14 C13 C12 . . 119.26(14) ?
C14 C13 H13 . . 120.4 ?
C12 C13 H13 . . 120.4 ?
C13 C14 C15 . . 118.27(14) ?
C13 C14 H14 . . 120.9 ?
C15 C14 H14 . . 120.9 ?
N3 C15 C14 . . 123.66(14) ?
N3 C15 H15 . . 118.2 ?
C14 C15 H15 . . 118.2 ?
S2 C16 H16A . . 109.5 ?
S2 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
S2 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 . 1.7806(15) ?
S1 S2 . 2.0341(5) ?
N1 C1 . 1.339(2) ?
N1 C5 . 1.344(2) ?
C1 C2 . 1.384(3) ?
C1 H1 . 0.95 ?
S2 C16 . 1.8050(18) ?
N2 C6 . 1.3426(19) ?
N2 C10 . 1.3434(19) ?
C2 C3 . 1.382(2) ?
C2 H2 . 0.95 ?
N3 C15 . 1.339(2) ?
N3 C11 . 1.3467(19) ?
C3 C4 . 1.391(2) ?
C3 H3 . 0.95 ?
C4 C5 . 1.392(2) ?
C4 H4 . 0.95 ?
C5 C6 . 1.487(2) ?
C6 C7 . 1.393(2) ?
C7 C8 . 1.391(2) ?
C7 H7 . 0.95 ?
C8 C9 . 1.384(2) ?
C9 C10 . 1.398(2) ?
C9 H9 . 0.95 ?
C10 C11 . 1.491(2) ?
C11 C12 . 1.396(2) ?
C12 C13 . 1.387(2) ?
C12 H12 . 0.95 ?
C13 C14 . 1.387(2) ?
C13 H13 . 0.95 ?
C14 C15 . 1.388(2) ?
C14 H14 . 0.95 ?
C15 H15 . 0.95 ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . 0.9(3) ?
N1 C1 C2 C3 . . . . -2.8(3) ?
C1 C2 C3 C4 . . . . 1.4(2) ?
C2 C3 C4 C5 . . . . 1.5(2) ?
C1 N1 C5 C4 . . . . 2.3(2) ?
C1 N1 C5 C6 . . . . -173.74(14) ?
C3 C4 C5 N1 . . . . -3.5(2) ?
C3 C4 C5 C6 . . . . 172.37(13) ?
C10 N2 C6 C7 . . . . 0.9(2) ?
C10 N2 C6 C5 . . . . -173.92(12) ?
N1 C5 C6 N2 . . . . -167.15(13) ?
C4 C5 C6 N2 . . . . 16.7(2) ?
N1 C5 C6 C7 . . . . 17.8(2) ?
C4 C5 C6 C7 . . . . -158.30(14) ?
N2 C6 C7 C8 . . . . -0.8(2) ?
C5 C6 C7 C8 . . . . 173.91(13) ?
C6 C7 C8 C9 . . . . 0.5(2) ?
C6 C7 C8 S1 . . . . -176.86(11) ?
S2 S1 C8 C9 . . . . -9.84(14) ?
S2 S1 C8 C7 . . . . 167.34(10) ?
C7 C8 C9 C10 . . . . -0.3(2) ?
S1 C8 C9 C10 . . . . 176.76(11) ?
C6 N2 C10 C9 . . . . -0.8(2) ?
C6 N2 C10 C11 . . . . 175.80(12) ?
C8 C9 C10 N2 . . . . 0.5(2) ?
C8 C9 C10 C11 . . . . -175.97(13) ?
C15 N3 C11 C12 . . . . -0.9(2) ?
C15 N3 C11 C10 . . . . 176.81(12) ?
N2 C10 C11 N3 . . . . 178.27(12) ?
C9 C10 C11 N3 . . . . -5.05(19) ?
N2 C10 C11 C12 . . . . -3.9(2) ?
C9 C10 C11 C12 . . . . 172.75(13) ?
N3 C11 C12 C13 . . . . 0.4(2) ?
C10 C11 C12 C13 . . . . -177.23(13) ?
C11 C12 C13 C14 . . . . 0.5(2) ?
C12 C13 C14 C15 . . . . -0.8(2) ?
C11 N3 C15 C14 . . . . 0.6(2) ?
C13 C14 C15 N3 . . . . 0.2(2) ?
