#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/69/2226918.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226918
loop_
_publ_author_name
'bin Shawkataly, Omar'
'Khan, Imthyaz Ahmed'
'Yeap, Chin Sing'
'Fun, Hoong-Kun'
_publ_section_title
;
 Tris[4-(methylsulfanyl)phenyl]arsine
;
_journal_coeditor_code           HB5559
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2116
_journal_paper_doi               10.1107/S160053681002876X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H21 As S3'
_chemical_formula_moiety         'C21 H21 As S3'
_chemical_formula_sum            'C21 H21 As S3'
_chemical_formula_weight         444.48
_chemical_name_systematic
;
Tris[4-(methylsulfanyl)phenyl]arsine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.8600(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0839(2)
_cell_length_b                   11.4556(2)
_cell_length_c                   17.3247(2)
_cell_measurement_reflns_used    6720
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      31.04
_cell_measurement_theta_min      2.65
_cell_volume                     2055.58(6)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            31130
_diffrn_reflns_theta_full        32.03
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         1.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.960
_exptl_absorpt_correction_T_max  0.821
_exptl_absorpt_correction_T_min  0.545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.860
_refine_diff_density_min         -0.507
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         7111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0664
_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
'calc w=1/[σ²(Fo²)+(0.0486P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                5098
_reflns_number_total             7111
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5559.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226918
_cod_database_fobs_code          2226918
loop_
_symmetry_equiv_pos_as_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
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
As As1 0.851830(19) 0.703422(18) 0.496255(12) 0.01802(6) Uani d . 1 . .
S S1 0.60863(5) 1.03859(5) 0.17158(3) 0.03019(13) Uani d . 1 . .
S S2 0.83788(6) 1.05708(5) 0.78874(3) 0.02996(13) Uani d . 1 . .
S S3 1.44348(5) 0.76333(6) 0.50798(4) 0.03192(14) Uani d . 1 . .
C C1 0.78015(19) 0.80668(17) 0.40006(12) 0.0183(4) Uani d . 1 . .
C C2 0.64685(19) 0.81069(18) 0.35944(13) 0.0224(4) Uani d . 1 . .
H H2A 0.5944 0.7653 0.3790 0.027 Uiso calc R 1 . .
C C3 0.59018(19) 0.88051(19) 0.29053(12) 0.0234(4) Uani d . 1 . .
H H3A 0.5008 0.8824 0.2651 0.028 Uiso calc R 1 . .
C C4 0.66768(19) 0.94822(18) 0.25918(12) 0.0204(4) Uani d . 1 . .
C C5 0.80152(19) 0.94533(17) 0.29981(11) 0.0192(4) Uani d . 1 . .
H H5A 0.8542 0.9905 0.2802 0.023 Uiso calc R 1 . .
C C6 0.85652(18) 0.87601(17) 0.36893(11) 0.0183(4) Uani d . 1 . .
H H6A 0.9458 0.8754 0.3952 0.022 Uiso calc R 1 . .
C C7 0.84768(18) 0.81425(17) 0.58127(12) 0.0178(4) Uani d . 1 . .
C C8 0.8544(2) 0.77177(19) 0.65816(13) 0.0262(5) Uani d . 1 . .
H H8A 0.8605 0.6918 0.6680 0.031 Uiso calc R 1 . .
C C9 0.8520(2) 0.8473(2) 0.71996(13) 0.0286(5) Uani d . 1 . .
H H9A 0.8567 0.8174 0.7709 0.034 Uiso calc R 1 . .
C C10 0.84255(19) 0.96751(18) 0.70672(12) 0.0204(4) Uani d . 1 . .
C C11 0.83575(18) 1.01047(18) 0.63009(12) 0.0197(4) Uani d . 1 . .
H H11A 0.8293 1.0904 0.6201 0.024 Uiso calc R 1 . .
C C12 0.83859(18) 0.93414(17) 0.56862(12) 0.0186(4) Uani d . 1 . .
H H12A 0.8343 0.9639 0.5178 0.022 Uiso calc R 1 . .
C C13 1.03380(18) 0.72022(17) 0.50883(12) 0.0178(4) Uani d . 1 . .
C C14 1.0843(2) 0.64556(18) 0.46419(12) 0.0214(4) Uani d . 1 . .
H H14A 1.0332 0.5857 0.4330 0.026 Uiso calc R 1 . .
C C15 1.2091(2) 0.65933(19) 0.46564(12) 0.0230(4) Uani d . 1 . .
H H15A 1.2408 0.6092 0.4351 0.028 Uiso calc R 1 . .
C C16 1.28772(19) 0.74795(19) 0.51259(12) 0.0209(4) Uani d . 1 . .
C C17 1.24043(19) 0.81979(18) 0.56012(12) 0.0198(4) Uani d . 1 . .
H H17A 1.2931 0.8768 0.5938 0.024 Uiso calc R 1 . .
C C18 1.11392(19) 0.80605(17) 0.55710(11) 0.0190(4) Uani d . 1 . .
H H18A 1.0825 0.8555 0.5881 0.023 Uiso calc R 1 . .
C C19 0.4396(2) 1.0054(2) 0.12929(14) 0.0353(6) Uani d . 1 . .
H H19A 0.4018 1.0427 0.0765 0.053 Uiso calc R 1 . .
H H19B 0.3984 1.0333 0.1660 0.053 Uiso calc R 1 . .
H H19C 0.4281 0.9225 0.1228 0.053 Uiso calc R 1 . .
C C20 0.7909(3) 1.1960(2) 0.73922(14) 0.0367(6) Uani d . 1 . .
H H20A 0.7705 1.2484 0.7761 0.055 Uiso calc R 1 . .
H H20B 0.7164 1.1862 0.6899 0.055 Uiso calc R 1 . .
H H20C 0.8606 1.2276 0.7252 0.055 Uiso calc R 1 . .
C C21 1.5139(2) 0.8774(3) 0.58105(19) 0.0518(8) Uani d . 1 . .
H H21A 1.5994 0.8937 0.5821 0.078 Uiso calc R 1 . .
H H21B 1.5180 0.8531 0.6350 0.078 Uiso calc R 1 . .
H H21C 1.4619 0.9465 0.5652 0.078 Uiso calc 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 0.0033 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
As As 0.0499 2.0058 '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
C7 As1 C13 . . 98.73(8) ?
C7 As1 C1 . . 97.87(8) ?
C13 As1 C1 . . 97.15(8) ?
C4 S1 C19 . . 103.97(10) ?
C10 S2 C20 . . 102.53(10) ?
C16 S3 C21 . . 103.15(11) ?
C2 C1 C6 . . 117.67(18) ?
C2 C1 As1 . . 118.95(14) ?
C6 C1 As1 . . 123.38(14) ?
C3 C2 C1 . . 121.84(18) ?
C3 C2 H2A . . 119.1 ?
C1 C2 H2A . . 119.1 ?
C2 C3 C4 . . 120.00(19) ?
C2 C3 H3A . . 120.0 ?
C4 C3 H3A . . 120.0 ?
C5 C4 C3 . . 118.59(18) ?
C5 C4 S1 . . 116.77(15) ?
C3 C4 S1 . . 124.64(15) ?
C6 C5 C4 . . 120.71(18) ?
C6 C5 H5A . . 119.6 ?
C4 C5 H5A . . 119.6 ?
C5 C6 C1 . . 121.18(18) ?
C5 C6 H6A . . 119.4 ?
C1 C6 H6A . . 119.4 ?
C12 C7 C8 . . 118.15(18) ?
C12 C7 As1 . . 122.86(14) ?
C8 C7 As1 . . 118.99(15) ?
C9 C8 C7 . . 120.8(2) ?
C9 C8 H8A . . 119.6 ?
C7 C8 H8A . . 119.6 ?
C8 C9 C10 . . 120.74(19) ?
C8 C9 H9A . . 119.6 ?
C10 C9 H9A . . 119.6 ?
C11 C10 C9 . . 118.78(18) ?
C11 C10 S2 . . 123.63(16) ?
C9 C10 S2 . . 117.58(15) ?
C12 C11 C10 . . 120.06(19) ?
C12 C11 H11A . . 120.0 ?
C10 C11 H11A . . 120.0 ?
C11 C12 C7 . . 121.50(18) ?
C11 C12 H12A . . 119.2 ?
C7 C12 H12A . . 119.2 ?
C18 C13 C14 . . 118.11(18) ?
C18 C13 As1 . . 123.30(15) ?
C14 C13 As1 . . 118.53(15) ?
C15 C14 C13 . . 121.01(19) ?
C15 C14 H14A . . 119.5 ?
C13 C14 H14A . . 119.5 ?
C14 C15 C16 . . 120.41(19) ?
C14 C15 H15A . . 119.8 ?
C16 C15 H15A . . 119.8 ?
C17 C16 C15 . . 119.12(18) ?
C17 C16 S3 . . 123.24(16) ?
C15 C16 S3 . . 117.64(16) ?
C16 C17 C18 . . 119.79(19) ?
C16 C17 H17A . . 120.1 ?
C18 C17 H17A . . 120.1 ?
C13 C18 C17 . . 121.48(19) ?
C13 C18 H18A . . 119.3 ?
C17 C18 H18A . . 119.3 ?
S1 C19 H19A . . 109.5 ?
S1 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
S1 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
S2 C20 H20A . . 109.5 ?
S2 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
S2 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
S3 C21 H21A . . 109.5 ?
S3 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
S3 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 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
As1 C7 . 1.9574(19) ?
As1 C13 . 1.960(2) ?
As1 C1 . 1.9660(19) ?
S1 C4 . 1.760(2) ?
S1 C19 . 1.793(2) ?
S2 C10 . 1.768(2) ?
S2 C20 . 1.795(2) ?
S3 C16 . 1.765(2) ?
S3 C21 . 1.793(3) ?
C1 C2 . 1.393(3) ?
C1 C6 . 1.401(3) ?
C2 C3 . 1.388(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.402(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.398(3) ?
C5 C6 . 1.384(3) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C7 C12 . 1.389(3) ?
C7 C8 . 1.395(3) ?
C8 C9 . 1.384(3) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.394(3) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.392(3) ?
C11 C12 . 1.387(3) ?
C11 H11A . 0.9300 ?
C12 H12A . 0.9300 ?
C13 C18 . 1.388(3) ?
C13 C14 . 1.397(3) ?
C14 C15 . 1.384(3) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.395(3) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.392(3) ?
C17 C18 . 1.393(3) ?
C17 H17A . 0.9300 ?
C18 H18A . 0.9300 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C21 H21A Cg1 1_655 0.96 2.55 3.441(3) 155 y
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
C7 As1 C1 C2 . . . . -89.18(16) ?
C13 As1 C1 C2 . . . . 170.93(16) ?
C7 As1 C1 C6 . . . . 91.80(17) ?
C13 As1 C1 C6 . . . . -8.09(17) ?
C6 C1 C2 C3 . . . . -0.1(3) ?
As1 C1 C2 C3 . . . . -179.13(16) ?
C1 C2 C3 C4 . . . . 1.0(3) ?
C2 C3 C4 C5 . . . . -1.3(3) ?
C2 C3 C4 S1 . . . . 179.00(16) ?
C19 S1 C4 C5 . . . . 172.71(16) ?
C19 S1 C4 C3 . . . . -7.6(2) ?
C3 C4 C5 C6 . . . . 0.8(3) ?
S1 C4 C5 C6 . . . . -179.54(15) ?
C4 C5 C6 C1 . . . . 0.2(3) ?
C2 C1 C6 C5 . . . . -0.5(3) ?
As1 C1 C6 C5 . . . . 178.50(14) ?
C13 As1 C7 C12 . . . . 79.74(17) ?
C1 As1 C7 C12 . . . . -18.79(18) ?
C13 As1 C7 C8 . . . . -100.12(17) ?
C1 As1 C7 C8 . . . . 161.35(16) ?
C12 C7 C8 C9 . . . . 0.0(3) ?
As1 C7 C8 C9 . . . . 179.87(17) ?
C7 C8 C9 C10 . . . . 0.1(3) ?
C8 C9 C10 C11 . . . . -0.1(3) ?
C8 C9 C10 S2 . . . . 179.13(18) ?
C20 S2 C10 C11 . . . . 11.2(2) ?
C20 S2 C10 C9 . . . . -167.94(19) ?
C9 C10 C11 C12 . . . . -0.1(3) ?
S2 C10 C11 C12 . . . . -179.27(15) ?
C10 C11 C12 C7 . . . . 0.2(3) ?
C8 C7 C12 C11 . . . . -0.2(3) ?
As1 C7 C12 C11 . . . . 179.94(14) ?
C7 As1 C13 C18 . . . . -9.49(18) ?
C1 As1 C13 C18 . . . . 89.65(17) ?
C7 As1 C13 C14 . . . . 173.47(16) ?
C1 As1 C13 C14 . . . . -87.39(16) ?
C18 C13 C14 C15 . . . . -2.3(3) ?
As1 C13 C14 C15 . . . . 174.91(15) ?
C13 C14 C15 C16 . . . . 0.6(3) ?
C14 C15 C16 C17 . . . . 2.2(3) ?
C14 C15 C16 S3 . . . . -177.57(16) ?
C21 S3 C16 C17 . . . . 4.1(2) ?
C21 S3 C16 C15 . . . . -176.15(18) ?
C15 C16 C17 C18 . . . . -3.1(3) ?
S3 C16 C17 C18 . . . . 176.61(15) ?
C14 C13 C18 C17 . . . . 1.3(3) ?
As1 C13 C18 C17 . . . . -175.74(14) ?
C16 C17 C18 C13 . . . . 1.4(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745609
2 PubChem 88176069
