#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301863 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/25/7202539.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_7202539
loop_
_publ_author_name
'McKeown, Neil B.'
'Badriya, Samer'
'Helliwell, Madeleine'
'Shkunov, Maxim'
_publ_section_title
;
 The synthesis of robust, polymeric hole-transport materials from
 oligoarylamine substituted styrenes
;
_journal_issue                   20
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              2088
_journal_paper_doi               10.1039/b614235d
_journal_volume                  17
_journal_year                    2007
_chemical_formula_sum            'C44 H31 N3 S2'
_chemical_formula_weight         665.84
_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                 110.149(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.985(4)
_cell_length_b                   24.813(8)
_cell_length_c                   13.194(4)
_cell_measurement_reflns_used    631
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      16.27
_cell_measurement_theta_min      2.24
_cell_volume                     3376.2(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.935
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2716
_diffrn_reflns_av_sigmaI/netI    0.4784
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20836
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.611
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         7817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.611
_refine_ls_R_factor_all          0.3273
_refine_ls_R_factor_gt           0.0609
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1842
_reflns_number_gt                1479
_reflns_number_total             7817
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b614235d.txt
_cod_data_source_block           s1033m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        3376.3(18)
_cod_original_sg_symbol_H-M      'P2(1)/c '
_cod_database_code               7202539
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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.11990(19) 0.23774(7) 0.26201(13) 0.0768(6) Uani 1 1 d . . .
S2 S 0.6456(2) -0.04755(7) 1.32902(14) 0.0848(7) Uani 1 1 d . . .
N1 N 0.4748(4) 0.23323(18) 0.9077(3) 0.0449(13) Uani 1 1 d . . .
N2 N 0.0909(5) 0.2372(2) 0.4922(4) 0.0562(15) Uani 1 1 d . . .
N3 N 0.5912(6) 0.0480(2) 1.1718(4) 0.0553(15) Uani 1 1 d . . .
C1 C 0.3746(6) 0.2324(2) 0.8030(4) 0.0433(16) Uani 1 1 d . . .
C2 C 0.4035(6) 0.2494(2) 0.7152(4) 0.062(2) Uani 1 1 d . . .
H2 H 0.4883 0.2593 0.7242 0.075 Uiso 1 1 calc R . .
C3 C 0.3109(7) 0.2522(3) 0.6141(4) 0.071(2) Uani 1 1 d . . .
H3 H 0.3316 0.2653 0.5560 0.086 Uiso 1 1 calc R . .
C4 C 0.1860(6) 0.2351(2) 0.5999(4) 0.0511(17) Uani 1 1 d . . .
C5 C 0.1563(6) 0.2176(2) 0.6869(4) 0.0504(17) Uani 1 1 d . . .
H5 H 0.0724 0.2063 0.6773 0.060 Uiso 1 1 calc R . .
C6 C 0.2496(6) 0.2165(2) 0.7890(4) 0.0449(16) Uani 1 1 d . . .
H6 H 0.2281 0.2051 0.8478 0.054 Uiso 1 1 calc R . .
C7 C 0.0052(6) 0.2819(3) 0.4634(5) 0.0519(18) Uani 1 1 d . . .
C8 C 0.0205(6) 0.3235(3) 0.5357(5) 0.063(2) Uani 1 1 d . . .
H8 H 0.0852 0.3219 0.6032 0.076 Uiso 1 1 calc R . .
C9 C -0.0625(8) 0.3686(3) 0.5067(5) 0.083(2) Uani 1 1 d . . .
H9 H -0.0516 0.3966 0.5558 0.100 Uiso 1 1 calc R . .
C10 C -0.1578(7) 0.3721(3) 0.4086(5) 0.079(2) Uani 1 1 d . . .
H10 H -0.2113 0.4022 0.3912 0.095 Uiso 1 1 calc R . .
C11 C -0.1747(7) 0.3321(3) 0.3375(5) 0.065(2) Uani 1 1 d . . .
H11 H -0.2400 0.3343 0.2703 0.079 Uiso 1 1 calc R . .
C12 C -0.0928(6) 0.2865(3) 0.3646(4) 0.0486(17) Uani 1 1 d . . .
C13 C -0.0272(6) 0.1840(2) 0.3318(4) 0.0469(17) Uani 1 1 d . . .
C14 C -0.0495(6) 0.1345(3) 0.2797(5) 0.067(2) Uani 1 1 d . . .
H14 H -0.1188 0.1310 0.2151 0.080 Uiso 1 1 calc R . .
C15 C 0.0291(7) 0.0897(3) 0.3213(5) 0.075(2) Uani 1 1 d . . .
H15 H 0.0142 0.0569 0.2853 0.091 Uiso 1 1 calc R . .
C16 C 0.1292(6) 0.0962(3) 0.4176(5) 0.072(2) Uani 1 1 d . . .
H16 H 0.1842 0.0673 0.4462 0.086 Uiso 1 1 calc R . .
C17 C 0.1505(6) 0.1443(3) 0.4729(4) 0.0552(18) Uani 1 1 d . . .
H17 H 0.2191 0.1474 0.5380 0.066 Uiso 1 1 calc R . .
C18 C 0.0714(6) 0.1877(3) 0.4328(4) 0.0511(18) Uani 1 1 d . . .
C19 C 0.5092(5) 0.1862(3) 0.9708(4) 0.0423(16) Uani 1 1 d . . .
C20 C 0.4742(5) 0.1355(2) 0.9263(4) 0.0450(16) Uani 1 1 d . . .
H20 H 0.4321 0.1316 0.8523 0.054 Uiso 1 1 calc R . .
C21 C 0.5025(6) 0.0907(2) 0.9927(4) 0.0527(18) Uani 1 1 d . . .
H21 H 0.4779 0.0567 0.9628 0.063 Uiso 1 1 calc R . .
C22 C 0.5661(6) 0.0954(2) 1.1019(5) 0.0459(16) Uani 1 1 d . . .
C23 C 0.6050(5) 0.1450(2) 1.1455(4) 0.0470(17) Uani 1 1 d . . .
H23 H 0.6512 0.1483 1.2189 0.056 Uiso 1 1 calc R . .
C24 C 0.5761(5) 0.1904(2) 1.0808(4) 0.0439(16) Uani 1 1 d . . .
H24 H 0.6017 0.2242 1.1114 0.053 Uiso 1 1 calc R . .
C25 C 0.4874(7) 0.0303(3) 1.2046(5) 0.0518(18) Uani 1 1 d . . .
C26 C 0.3728(8) 0.0581(3) 1.1703(5) 0.074(2) Uani 1 1 d . . .
H26 H 0.3636 0.0878 1.1254 0.088 Uiso 1 1 calc R . .
C27 C 0.2716(8) 0.0425(3) 1.2016(6) 0.090(3) Uani 1 1 d . . .
H27 H 0.1953 0.0625 1.1799 0.108 Uiso 1 1 calc R . .
C28 C 0.2817(10) -0.0029(4) 1.2656(6) 0.099(3) Uani 1 1 d . . .
H28 H 0.2117 -0.0136 1.2851 0.119 Uiso 1 1 calc R . .
C29 C 0.3922(9) -0.0317(3) 1.2994(5) 0.076(2) Uani 1 1 d . . .
H29 H 0.3988 -0.0625 1.3410 0.091 Uiso 1 1 calc R . .
C30 C 0.4979(8) -0.0141(3) 1.2705(5) 0.063(2) Uani 1 1 d . . .
C31 C 0.7220(7) -0.0334(3) 1.2367(5) 0.065(2) Uani 1 1 d . . .
C32 C 0.8204(9) -0.0668(3) 1.2312(6) 0.087(3) Uani 1 1 d . . .
H32 H 0.8405 -0.0971 1.2752 0.105 Uiso 1 1 calc R . .
C33 C 0.8894(8) -0.0575(3) 1.1646(7) 0.089(3) Uani 1 1 d . . .
H33 H 0.9550 -0.0809 1.1634 0.107 Uiso 1 1 calc R . .
C34 C 0.8599(8) -0.0126(3) 1.0993(6) 0.079(2) Uani 1 1 d . . .
H34 H 0.9061 -0.0052 1.0535 0.095 Uiso 1 1 calc R . .
C35 C 0.7597(7) 0.0218(3) 1.1021(6) 0.063(2) Uani 1 1 d . . .
H35 H 0.7390 0.0517 1.0567 0.075 Uiso 1 1 calc R . .
C36 C 0.6912(7) 0.0125(3) 1.1705(5) 0.0574(19) Uani 1 1 d . . .
C37 C 0.5497(5) 0.2810(2) 0.9342(4) 0.0353(14) Uani 1 1 d . . .
C38 C 0.6849(6) 0.2788(2) 0.9700(4) 0.0435(16) Uani 1 1 d . . .
H38 H 0.7272 0.2458 0.9783 0.052 Uiso 1 1 calc R . .
C39 C 0.7552(6) 0.3260(3) 0.9932(4) 0.0466(16) Uani 1 1 d . . .
H39 H 0.8452 0.3239 1.0180 0.056 Uiso 1 1 calc R . .
C40 C 0.6976(6) 0.3765(3) 0.9810(4) 0.0465(17) Uani 1 1 d . . .
C41 C 0.5622(7) 0.3772(2) 0.9424(4) 0.0557(18) Uani 1 1 d . . .
H41 H 0.5194 0.4102 0.9309 0.067 Uiso 1 1 calc R . .
C42 C 0.4894(6) 0.3299(2) 0.9209(4) 0.0486(16) Uani 1 1 d . . .
H42 H 0.3993 0.3317 0.8973 0.058 Uiso 1 1 calc R . .
C43 C 0.7690(8) 0.4265(3) 0.9995(5) 0.067(2) Uani 1 1 d . . .
H43 H 0.7192 0.4577 0.9805 0.080 Uiso 1 1 calc R . .
C44 C 0.8915(8) 0.4335(3) 1.0386(6) 0.100(3) Uani 1 1 d . . .
H44A H 0.9466 0.4040 1.0591 0.120 Uiso 1 1 calc R . .
H44B H 0.9256 0.4682 1.0464 0.120 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 S1 C12 101.9(3) . . ?
C31 S2 C30 101.2(4) . . ?
C19 N1 C37 122.2(4) . . ?
C19 N1 C1 121.1(5) . . ?
C37 N1 C1 115.9(4) . . ?
C7 N2 C18 124.3(5) . . ?
C7 N2 C4 118.6(5) . . ?
C18 N2 C4 115.4(5) . . ?
C36 N3 C25 121.3(6) . . ?
C36 N3 C22 118.2(6) . . ?
C25 N3 C22 116.4(6) . . ?
C2 C1 C6 119.0(5) . . ?
C2 C1 N1 118.9(5) . . ?
C6 C1 N1 122.1(5) . . ?
C1 C2 C3 121.8(6) . . ?
C2 C3 C4 119.0(6) . . ?
C5 C4 C3 119.6(5) . . ?
C5 C4 N2 122.4(6) . . ?
C3 C4 N2 118.0(6) . . ?
C4 C5 C6 120.9(6) . . ?
C1 C6 C5 119.7(5) . . ?
C8 C7 C12 117.5(7) . . ?
C8 C7 N2 119.3(6) . . ?
C12 C7 N2 123.2(6) . . ?
C7 C8 C9 119.6(6) . . ?
C10 C9 C8 121.5(7) . . ?
C11 C10 C9 119.9(7) . . ?
C10 C11 C12 119.7(6) . . ?
C7 C12 C11 121.8(6) . . ?
C7 C12 S1 122.6(6) . . ?
C11 C12 S1 115.5(5) . . ?
C14 C13 C18 118.4(6) . . ?
C14 C13 S1 116.5(5) . . ?
C18 C13 S1 125.0(5) . . ?
C13 C14 C15 121.9(6) . . ?
C16 C15 C14 117.4(6) . . ?
C15 C16 C17 121.8(6) . . ?
C18 C17 C16 120.5(6) . . ?
C17 C18 C13 119.7(6) . . ?
C17 C18 N2 120.4(5) . . ?
C13 C18 N2 119.8(6) . . ?
C20 C19 C24 118.8(5) . . ?
C20 C19 N1 121.6(5) . . ?
C24 C19 N1 119.6(5) . . ?
C21 C20 C19 119.5(5) . . ?
C22 C21 C20 121.2(6) . . ?
C23 C22 C21 119.4(6) . . ?
C23 C22 N3 119.8(5) . . ?
C21 C22 N3 120.8(6) . . ?
C22 C23 C24 120.3(5) . . ?
C23 C24 C19 120.7(6) . . ?
C26 C25 C30 118.5(7) . . ?
C26 C25 N3 119.1(6) . . ?
C30 C25 N3 122.4(7) . . ?
C27 C26 C25 120.5(7) . . ?
C26 C27 C28 120.6(8) . . ?
C29 C28 C27 120.4(9) . . ?
C28 C29 C30 118.7(8) . . ?
C25 C30 C29 121.2(7) . . ?
C25 C30 S2 121.3(7) . . ?
C29 C30 S2 117.3(6) . . ?
C32 C31 C36 118.6(8) . . ?
C32 C31 S2 119.4(6) . . ?
C36 C31 S2 121.9(7) . . ?
C33 C32 C31 123.4(8) . . ?
C32 C33 C34 118.5(8) . . ?
C33 C34 C35 119.5(8) . . ?
C36 C35 C34 121.6(7) . . ?
C35 C36 C31 118.3(7) . . ?
C35 C36 N3 120.3(7) . . ?
C31 C36 N3 121.4(7) . . ?
C42 C37 C38 119.4(6) . . ?
C42 C37 N1 119.8(5) . . ?
C38 C37 N1 120.8(5) . . ?
C39 C38 C37 119.5(6) . . ?
C38 C39 C40 122.9(6) . . ?
C39 C40 C41 116.1(6) . . ?
C39 C40 C43 123.9(6) . . ?
C41 C40 C43 119.9(7) . . ?
C42 C41 C40 121.9(6) . . ?
C37 C42 C41 120.2(6) . . ?
C44 C43 C40 128.4(8) . . ?
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 C13 1.737(6) . ?
S1 C12 1.763(6) . ?
S2 C31 1.736(8) . ?
S2 C30 1.748(7) . ?
N1 C19 1.407(6) . ?
N1 C37 1.417(6) . ?
N1 C1 1.439(6) . ?
N2 C7 1.420(7) . ?
N2 C18 1.432(6) . ?
N2 C4 1.445(6) . ?
N3 C36 1.413(8) . ?
N3 C25 1.421(7) . ?
N3 C22 1.460(6) . ?
C1 C2 1.370(6) . ?
C1 C6 1.378(7) . ?
C2 C3 1.372(6) . ?
C3 C4 1.385(8) . ?
C4 C5 1.368(7) . ?
C5 C6 1.383(6) . ?
C7 C8 1.376(7) . ?
C7 C12 1.380(7) . ?
C8 C9 1.411(8) . ?
C9 C10 1.358(8) . ?
C10 C11 1.334(7) . ?
C11 C12 1.414(7) . ?
C13 C14 1.388(7) . ?
C13 C18 1.402(7) . ?
C14 C15 1.398(7) . ?
C15 C16 1.374(7) . ?
C16 C17 1.377(7) . ?
C17 C18 1.370(7) . ?
C19 C20 1.386(6) . ?
C19 C24 1.387(6) . ?
C20 C21 1.383(6) . ?
C21 C22 1.373(7) . ?
C22 C23 1.364(7) . ?
C23 C24 1.384(6) . ?
C25 C26 1.369(8) . ?
C25 C30 1.383(8) . ?
C26 C27 1.368(9) . ?
C27 C28 1.390(9) . ?
C28 C29 1.344(9) . ?
C29 C30 1.410(9) . ?
C31 C32 1.383(9) . ?
C31 C36 1.404(8) . ?
C32 C33 1.363(9) . ?
C33 C34 1.376(9) . ?
C34 C35 1.405(9) . ?
C35 C36 1.380(8) . ?
C37 C42 1.365(6) . ?
C37 C38 1.396(7) . ?
C38 C39 1.376(7) . ?
C39 C40 1.388(7) . ?
C40 C41 1.396(7) . ?
C40 C43 1.444(8) . ?
C41 C42 1.393(7) . ?
C43 C44 1.277(9) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21143133
2 PubChem 102086556
