#------------------------------------------------------------------------------
#$Date: 2021-02-03 21:57:32 +0200 (Wed, 03 Feb 2021) $
#$Revision: 261400 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/84/4518455.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_4518455
loop_
_publ_author_name
'Wang, Xing-Huo'
'Lou, Xin-Yue'
'Lu, Tong'
'Wang, Chunyu'
'Tang, Jun'
'Liu, Fengqi'
'Wang, Yan'
'Yang, Ying-Wei'
_publ_section_title
;
 Supramolecular Engineering of Efficient Artificial Light-Harvesting
 Systems from Cyanovinylene Chromophores and Pillar[5]arene-Based Polymer
 Hosts.
;
_journal_issue                   3
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              4593
_journal_page_last               4604
_journal_paper_doi               10.1021/acsami.0c21651
_journal_volume                  13
_journal_year                    2021
_chemical_formula_moiety         'C25 H26 N4 O S'
_chemical_formula_sum            'C25 H26 N4 O S'
_chemical_formula_weight         430.56
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                99.8890(10)
_cell_angle_beta                 98.5000(10)
_cell_angle_gamma                111.2700(10)
_cell_formula_units_Z            2
_cell_length_a                   10.2816(4)
_cell_length_b                   10.7860(3)
_cell_length_c                   11.5784(4)
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.564
_cell_measurement_theta_min      2.985
_cell_volume                     1147.48(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294.5
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30927
_diffrn_reflns_theta_full        29.61
_diffrn_reflns_theta_max         29.61
_diffrn_reflns_theta_min         2.98
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_correction_T_min  0.9821
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         6424
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0611
_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)+(0.0739P)²+0.3983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1580
_refine_ls_wR_factor_ref         0.1790
_reflns_number_gt                4451
_reflns_number_total             6424
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            am0c21651_si_002.cif
_cod_data_source_block           33
_cod_database_code               4518455
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 N3, C19
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C22, C23
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(S1) = Uanis(S1A)
Uanis(N3) = Uanis(N3A)
4. Others
 Sof(N3A)=Sof(S1A)=1-FVAR(1)
 Sof(S1)=Sof(N3)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C3(H3A,H3B), C4(H4A,H4B), C2(H2A,H2B), C13(H13A,H13B), C15(H15A,
 H15B)
5.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C7(H7), C10(H10), C9(H9), C24(H24), C21(H21), C23(H23), C22(H22)
5.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.14905(7) 0.94930(7) 0.52514(6) 0.0633(2) Uani 0.923(3) d A 1 . .
N3 N 0.3069(5) 0.8156(4) 0.6013(4) 0.0700(9) Uani 0.923(3) d A 1 . U
N3A N 0.183(4) 0.923(3) 0.529(3) 0.0700(9) Uani 0.077(3) d A 2 . .
S1A S 0.3041(17) 0.8344(18) 0.5806(15) 0.0633(2) Uani 0.077(3) d A 2 . .
O1 O 0.61152(14) 0.69018(14) 0.39838(11) 0.0555(3) Uani 1 d . . . .
N1 N 0.7063(2) 0.7389(2) 0.00961(15) 0.0667(5) Uani 1 d . . . .
C6 C 0.58962(18) 0.73022(18) 0.29448(15) 0.0465(4) Uani 1 d . . . .
C5 C 0.7238(2) 0.6416(2) 0.41916(17) 0.0536(4) Uani 1 d . . . .
H5A H 0.8139 0.7099 0.4141 0.064 Uiso 1 calc . . R .
H5B H 0.7017 0.5580 0.3589 0.064 Uiso 1 calc . . R .
C11 C 0.48906(19) 0.79212(18) 0.28495(16) 0.0488(4) Uani 1 d . . . .
C8 C 0.6338(2) 0.7536(2) 0.09736(17) 0.0548(4) Uani 1 d . . . .
C16 C 0.42325(19) 0.81096(18) 0.38307(16) 0.0499(4) Uani 1 d . . . .
H16 H 0.4557 0.7840 0.4498 0.060 Uiso 1 calc . . R .
C3 C 0.8465(2) 0.5537(2) 0.56557(17) 0.0557(4) Uani 1 d . . . .
H3A H 0.8166 0.4669 0.5071 0.067 Uiso 1 calc . . R .
H3B H 0.9377 0.6152 0.5555 0.067 Uiso 1 calc . . R .
C7 C 0.6590(2) 0.71101(19) 0.20383(16) 0.0511(4) Uani 1 d . . . .
H7 H 0.7234 0.6693 0.2132 0.061 Uiso 1 calc . . R .
C4 C 0.7353(2) 0.6147(2) 0.54240(17) 0.0563(5) Uani 1 d . . . .
H4A H 0.6428 0.5514 0.5487 0.068 Uiso 1 calc . . R .
H4B H 0.7629 0.6997 0.6026 0.068 Uiso 1 calc . . R .
C19 C 0.26856(19) 0.86905(19) 0.50681(19) 0.0538(4) Uani 1 d . . . U
C17 C 0.3210(2) 0.8616(2) 0.39612(18) 0.0543(4) Uani 1 d A . . .
C20 C 0.2368(2) 0.8453(2) 0.6887(2) 0.0612(5) Uani 1 d . . . .
C10 C 0.4666(2) 0.8331(2) 0.17703(18) 0.0605(5) Uani 1 d . . . .
H10 H 0.4022 0.8748 0.1670 0.073 Uiso 1 calc . . R .
C25 C 0.1491(2) 0.9157(2) 0.6648(2) 0.0592(5) Uani 1 d A . . .
C9 C 0.5340(2) 0.8152(2) 0.08674(18) 0.0632(5) Uani 1 d . . . .
H9 H 0.5141 0.8438 0.0173 0.076 Uiso 1 calc . . R .
N4 N 1.0450(3) 0.4183(3) 0.7309(2) 0.1032(8) Uani 1 d . . . .
C2 C 0.8648(2) 0.5308(2) 0.69196(18) 0.0624(5) Uani 1 d . . . .
H2A H 0.8979 0.6182 0.7502 0.075 Uiso 1 calc . . R .
H2B H 0.7725 0.4724 0.7028 0.075 Uiso 1 calc . . R .
C1 C 0.9666(3) 0.4674(3) 0.7147(2) 0.0717(6) Uani 1 d . . . .
C13 C 0.8125(3) 0.6781(3) 0.0217(2) 0.0741(6) Uani 1 d . . . .
H13A H 0.8681 0.7108 0.1043 0.089 Uiso 1 calc . . R .
H13B H 0.8777 0.7097 -0.0296 0.089 Uiso 1 calc . . R .
C15 C 0.6814(3) 0.7830(3) -0.1016(2) 0.0767(6) Uani 1 d . . . .
H15A H 0.7673 0.8054 -0.1330 0.092 Uiso 1 calc . . R .
H15B H 0.6632 0.8656 -0.0833 0.092 Uiso 1 calc . . R .
C24 C 0.0767(2) 0.9506(2) 0.7499(3) 0.0750(7) Uani 1 d . . . .
H24 H 0.0178 0.9968 0.7345 0.090 Uiso 1 calc A . R .
C18 C 0.2558(3) 0.9080(3) 0.3037(2) 0.0789(7) Uani 1 d . . . .
C21 C 0.2514(3) 0.8069(3) 0.7963(2) 0.0798(7) Uani 1 d A . . .
H21 H 0.3080 0.7584 0.8115 0.096 Uiso 1 calc . . R .
C23 C 0.0961(3) 0.9136(3) 0.8577(3) 0.0850(7) Uani 1 d A . . U
H23 H 0.0511 0.9375 0.9166 0.102 Uiso 1 calc . . R .
C14 C 0.5578(3) 0.6757(3) -0.1962(2) 0.0867(8) Uani 1 d . . . .
H14A H 0.5406 0.7122 -0.2642 0.130 Uiso 1 calc . . GR .
H14B H 0.4738 0.6487 -0.1639 0.130 Uiso 1 calc . . GR .
H14C H 0.5797 0.5974 -0.2212 0.130 Uiso 1 calc . . GR .
N2 N 0.2002(3) 0.9447(4) 0.2325(3) 0.1260(12) Uani 1 d A . . .
C22 C 0.1811(3) 0.8416(3) 0.8801(3) 0.0885(7) Uani 1 d . . . U
H22 H 0.1904 0.8166 0.9529 0.106 Uiso 1 calc A . R .
C12 C 0.7497(4) 0.5263(3) -0.0099(3) 0.0922(8) Uani 1 d . . . .
H12A H 0.6923 0.4928 -0.0908 0.138 Uiso 1 calc . . GR .
H12B H 0.6908 0.4939 0.0445 0.138 Uiso 1 calc . . GR .
H12C H 0.8252 0.4938 -0.0040 0.138 Uiso 1 calc . . GR .
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'
O O 0.0106 0.0060 '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
C25 S1 C19 88.72(10) . . ?
C20 N3 C19 106.2(3) . . ?
C19 N3A S1A 31.0(10) . . ?
C19 N3A C25 112(2) . . ?
C25 N3A S1A 80.9(16) . . ?
N3A S1A C17 70.5(10) . . ?
C19 S1A N3A 37.3(11) . . ?
C19 S1A C17 33.2(6) . . ?
C19 S1A C20 117.5(11) . . ?
C20 S1A N3A 80.3(11) . . ?
C20 S1A C17 150.7(9) . . ?
C6 O1 C5 117.80(13) . . ?
C8 N1 C13 121.75(17) . . ?
C8 N1 C15 121.57(19) . . ?
C13 N1 C15 116.68(18) . . ?
O1 C6 C11 115.37(15) . . ?
O1 C6 C7 122.52(15) . . ?
C7 C6 C11 122.10(16) . . ?
O1 C5 H5A 110.1 . . ?
O1 C5 H5B 110.1 . . ?
O1 C5 C4 108.09(14) . . ?
H5A C5 H5B 108.4 . . ?
C4 C5 H5A 110.1 . . ?
C4 C5 H5B 110.1 . . ?
C6 C11 C16 119.09(16) . . ?
C10 C11 C6 115.10(16) . . ?
C10 C11 C16 125.78(16) . . ?
N1 C8 C7 120.94(18) . . ?
N1 C8 C9 121.65(18) . . ?
C7 C8 C9 117.39(17) . . ?
C11 C16 H16 114.4 . . ?
C17 C16 C11 131.29(18) . . ?
C17 C16 H16 114.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C2 C3 C4 111.21(16) . . ?
C6 C7 C8 121.06(17) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C5 C4 C3 110.11(15) . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.2 . . ?
N3 C19 S1 116.4(2) . . ?
N3 C19 C17 124.2(2) . . ?
N3A C19 S1 5.3(15) . . ?
N3A C19 N3 111.1(15) . . ?
N3A C19 C17 124.7(15) . . ?
S1A C19 S1 116.9(9) . . ?
S1A C19 N3 3.8(12) . . ?
S1A C19 N3A 111.7(17) . . ?
S1A C19 C17 123.5(8) . . ?
C17 C19 S1 119.45(15) . . ?
C16 C17 S1A 97.7(4) . . ?
C16 C17 C19 121.06(17) . . ?
C16 C17 C18 123.34(19) . . ?
C19 C17 S1A 23.3(4) . . ?
C18 C17 S1A 138.9(4) . . ?
C18 C17 C19 115.59(17) . . ?
N3 C20 S1A 12.4(6) . . ?
N3 C20 C25 117.8(2) . . ?
C25 C20 S1A 105.7(6) . . ?
C21 C20 N3 121.7(2) . . ?
C21 C20 S1A 133.8(6) . . ?
C21 C20 C25 120.5(2) . . ?
C11 C10 H10 118.2 . . ?
C9 C10 C11 123.68(18) . . ?
C9 C10 H10 118.2 . . ?
N3A C25 S1 17.9(13) . . ?
C20 C25 S1 110.83(15) . . ?
C20 C25 N3A 93.0(13) . . ?
C20 C25 C24 120.8(2) . . ?
C24 C25 S1 128.40(19) . . ?
C24 C25 N3A 146.3(13) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.66(18) . . ?
C10 C9 H9 119.7 . . ?
C3 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C1 C2 C3 112.26(18) . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
N4 C1 C2 179.2(3) . . ?
N1 C13 H13A 108.7 . . ?
N1 C13 H13B 108.7 . . ?
N1 C13 C12 114.1(2) . . ?
H13A C13 H13B 107.6 . . ?
C12 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
N1 C15 H15A 109.1 . . ?
N1 C15 H15B 109.1 . . ?
N1 C15 C14 112.7(2) . . ?
H15A C15 H15B 107.8 . . ?
C14 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C25 C24 H24 121.3 . . ?
C23 C24 C25 117.4(2) . . ?
C23 C24 H24 121.3 . . ?
N2 C18 C17 177.5(3) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 C20 118.8(3) . . ?
C22 C21 H21 120.6 . . ?
C24 C23 H23 119.2 . . ?
C24 C23 C22 121.6(2) . . ?
C22 C23 H23 119.2 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C21 C22 C23 120.9(3) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
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 C19 1.7578(18) . ?
S1 C25 1.717(2) . ?
N3 C19 1.392(4) . ?
N3 C20 1.385(4) . ?
N3A S1A 1.91(4) . ?
N3A C19 1.25(4) . ?
N3A C25 1.67(3) . ?
S1A C19 1.058(14) . ?
S1A C17 2.229(16) . ?
S1A C20 1.524(16) . ?
O1 C6 1.361(2) . ?
O1 C5 1.4365(19) . ?
N1 C8 1.367(3) . ?
N1 C13 1.465(3) . ?
N1 C15 1.467(3) . ?
C6 C11 1.421(2) . ?
C6 C7 1.381(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.501(3) . ?
C11 C16 1.427(3) . ?
C11 C10 1.410(3) . ?
C8 C7 1.409(3) . ?
C8 C9 1.412(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.365(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.526(2) . ?
C3 C2 1.521(3) . ?
C7 H7 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C19 C17 1.463(3) . ?
C17 C18 1.435(3) . ?
C20 C25 1.400(3) . ?
C20 C21 1.384(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.361(3) . ?
C25 C24 1.400(3) . ?
C9 H9 0.9300 . ?
N4 C1 1.125(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.460(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.479(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.497(4) . ?
C24 H24 0.9300 . ?
C24 C23 1.383(4) . ?
C18 N2 1.140(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.373(4) . ?
C23 H23 0.9300 . ?
C23 C22 1.388(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C22 H22 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
