#------------------------------------------------------------------------------
#$Date: 2022-06-28 20:11:28 +0300 (Tue, 28 Jun 2022) $
#$Revision: 276356 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/26/7232676.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_7232676
loop_
_publ_author_name
'Saccone, Marco'
'Riebe, Steffen'
'Stelzer, Jacqueline'
'Wölper, Christoph'
'Daniliuc, Constantin G.'
'Voskuhl, Jens'
'Giese, Michael'
_publ_section_title
;
 Structure--property relationships in aromatic thioethers featuring
 aggregation-induced emission: solid-state structures and theoretical
 analysis
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              3097
_journal_paper_doi               10.1039/C9CE00444K
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C36 H44 N2 O2 S2'
_chemical_formula_sum            'C36 H44 N2 O2 S2'
_chemical_formula_weight         600.85
_chemical_properties_physical    none
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                JS11
_audit_creation_date             2017-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2019-02-04 deposited with the CCDC.    2019-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                73.861(5)
_cell_angle_beta                 84.239(7)
_cell_angle_gamma                88.632(9)
_cell_formula_units_Z            1
_cell_length_a                   5.3350(9)
_cell_length_b                   9.6840(12)
_cell_length_c                   16.4820(18)
_cell_measurement_reflns_used    20819
_cell_measurement_temperature    80(2)
_cell_measurement_theta_max      26.847
_cell_measurement_theta_min      1.025
_cell_volume                     813.83(19)
_computing_cell_refinement       'XDS V. 1 March 2015'
_computing_data_collection       'P11 Crystallography Control GUI'
_computing_data_reduction        'XDS V. 1 March 2015'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2014)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (G. M. Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (G. M. Sheldrick, 2015)'
_diffrn_ambient_temperature      80(2)
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'P11 beamline PETRA III Pilatus 6M detector'
_diffrn_measurement_method       'CCD φ-scans'
_diffrn_radiation_monochromator  'LN2 cooled double crystal'
_diffrn_radiation_source         'PETRAIII, Hamburg'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.563600
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22381
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        19.765
_diffrn_reflns_theta_max         26.824
_diffrn_reflns_theta_min         1.025
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0441 before and 0.0409 after correction.
The Ratio of minimum to maximum transmission is 0.9690.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       needle
_exptl_crystal_F_000             322
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent:  diemthylformamid '
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         6495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0339
_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)+(0.0570P)²+0.1914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6184
_reflns_number_total             6495
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00444k2.cif
_cod_data_source_block           10690_001
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'TRICLINIC' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7232673--7232677.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7232676
_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.
;
_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.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,
 H15B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C10(H10)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_shelxl_version_number     2016/6
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
S1 S 0.77953(3) 0.75558(2) 0.13153(2) 0.01038(5) Uani 1 1 d .
O1 O 0.00465(10) 0.49177(5) 0.29966(3) 0.01231(9) Uani 1 1 d .
N1 N -0.02352(13) 0.88892(7) -0.12543(4) 0.01646(11) Uani 1 1 d .
C1 C 0.12476(12) 0.92572(7) -0.08947(4) 0.01044(10) Uani 1 1 d .
C2 C 0.31316(11) 0.96644(6) -0.04369(4) 0.00778(9) Uani 1 1 d .
C3 C 0.42512(11) 0.85712(6) 0.01604(4) 0.00824(10) Uani 1 1 d .
H3 H 0.370826 0.760479 0.026577 0.010 Uiso 1 1 calc R
C4 C 0.61541(11) 0.88845(6) 0.06027(4) 0.00785(10) Uani 1 1 d .
C5 C 0.56468(12) 0.60887(6) 0.15579(4) 0.00930(10) Uani 1 1 d .
C6 C 0.59998(13) 0.50058(7) 0.11443(4) 0.01246(11) Uani 1 1 d .
H6 H 0.738034 0.504577 0.072667 0.015 Uiso 1 1 calc R
C7 C 0.42877(14) 0.38705(7) 0.13575(4) 0.01335(11) Uani 1 1 d .
H7 H 0.450669 0.313278 0.107890 0.016 Uiso 1 1 calc R
C8 C 0.22524(13) 0.37922(7) 0.19727(4) 0.01117(11) Uani 1 1 d .
H8 H 0.109675 0.301111 0.211038 0.013 Uiso 1 1 calc R
C9 C 0.19384(12) 0.48779(7) 0.23830(4) 0.00917(10) Uani 1 1 d .
C10 C 0.36334(12) 0.60317(7) 0.21727(4) 0.00949(10) Uani 1 1 d .
H10 H 0.341142 0.677314 0.244836 0.011 Uiso 1 1 calc R
C11 C -0.16347(12) 0.37048(7) 0.32866(4) 0.01039(10) Uani 1 1 d .
H11A H -0.066995 0.281042 0.349160 0.012 Uiso 1 1 calc R
H11B H -0.257565 0.360996 0.281674 0.012 Uiso 1 1 calc R
C12 C -0.34423(12) 0.39527(7) 0.40009(4) 0.01035(10) Uani 1 1 d .
H12A H -0.441835 0.483922 0.378631 0.012 Uiso 1 1 calc R
H12B H -0.247768 0.408744 0.445614 0.012 Uiso 1 1 calc R
C13 C -0.52458(12) 0.26842(7) 0.43623(4) 0.01107(11) Uani 1 1 d .
H13A H -0.425254 0.180183 0.456964 0.013 Uiso 1 1 calc R
H13B H -0.618995 0.255254 0.390169 0.013 Uiso 1 1 calc R
C14 C -0.71229(12) 0.28673(7) 0.50877(4) 0.01104(11) Uani 1 1 d .
H14A H -0.618777 0.303644 0.554082 0.013 Uiso 1 1 calc R
H14B H -0.817648 0.372265 0.487624 0.013 Uiso 1 1 calc R
C15 C -0.88235(12) 0.15552(7) 0.54591(4) 0.01157(11) Uani 1 1 d .
H15A H -0.775254 0.070588 0.566634 0.014 Uiso 1 1 calc R
H15B H -0.972880 0.138617 0.499949 0.014 Uiso 1 1 calc R
C16 C -1.07603(12) 0.16696(7) 0.61856(4) 0.01112(11) Uani 1 1 d .
H16A H -0.987722 0.182918 0.665240 0.013 Uiso 1 1 calc R
H16B H -1.186218 0.250680 0.598385 0.013 Uiso 1 1 calc R
C17 C -1.23708(14) 0.03124(8) 0.65197(5) 0.01551(12) Uani 1 1 d .
H17A H -1.317520 0.013549 0.604185 0.019 Uiso 1 1 calc R
H17B H -1.125644 -0.051284 0.673505 0.019 Uiso 1 1 calc R
C18 C -1.44173(14) 0.03707(9) 0.72238(5) 0.01747(13) Uani 1 1 d .
H18A H -1.363953 0.050396 0.771087 0.026 Uiso 1 1 calc GR
H18B H -1.538036 -0.053037 0.739746 0.026 Uiso 1 1 calc GR
H18C H -1.554854 0.117614 0.701591 0.026 Uiso 1 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
C4 S1 C5 100.89(3) . .
C9 O1 C11 117.56(5) . .
N1 C1 C2 177.94(7) . .
C3 C2 C1 117.73(6) . .
C3 C2 C4 121.59(6) . 2_675
C4 C2 C1 120.66(5) 2_675 .
C4 C3 C2 120.69(6) . .
C2 C4 S1 118.86(5) 2_675 .
C3 C4 S1 123.37(5) . .
C3 C4 C2 117.71(5) . 2_675
C6 C5 S1 120.46(5) . .
C10 C5 S1 118.65(5) . .
C10 C5 C6 120.89(6) . .
C7 C6 C5 118.65(6) . .
C6 C7 C8 121.41(6) . .
C7 C8 C9 119.17(6) . .
O1 C9 C8 124.71(6) . .
O1 C9 C10 115.11(5) . .
C8 C9 C10 120.17(6) . .
C5 C10 C9 119.71(6) . .
O1 C11 C12 107.74(5) . .
C11 C12 C13 110.91(5) . .
C12 C13 C14 113.52(5) . .
C15 C14 C13 112.18(5) . .
C14 C15 C16 114.94(5) . .
C17 C16 C15 111.42(5) . .
C18 C17 C16 114.41(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C4 1.7647(6) .
S1 C5 1.7782(7) .
O1 C9 1.3630(8) .
O1 C11 1.4369(8) .
N1 C1 1.1529(9) .
C1 C2 1.4394(9) .
C2 C3 1.3983(8) .
C2 C4 1.4092(9) 2_675
C3 C4 1.3928(9) .
C5 C6 1.4008(9) .
C5 C10 1.3918(9) .
C6 C7 1.3911(10) .
C7 C8 1.3976(9) .
C8 C9 1.3982(9) .
C9 C10 1.3987(9) .
C11 C12 1.5138(9) .
C12 C13 1.5245(9) .
C13 C14 1.5274(9) .
C14 C15 1.5244(10) .
C15 C16 1.5276(9) .
C16 C17 1.5249(10) .
C17 C18 1.5235(10) .
loop_
_cod_changelog_entry_id
_cod_changelog_entry_author
_cod_changelog_entry_date
_cod_changelog_entry_text
1 'Vaitkus, Antanas' 2022-06-28T20:09:00+03:00
;
 Removed the '_chemical_name_systematic' data item that had an incorrect value.
;
