#------------------------------------------------------------------------------
#$Date: 2022-06-28 20:11:28 +0300 (Tue, 28 Jun 2022) $
#$Revision: 276356 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/26/7232675.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_7232675
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                10683
_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                98.317(3)
_cell_angle_beta                 94.448(3)
_cell_angle_gamma                92.455(3)
_cell_formula_units_Z            1
_cell_length_a                   5.3026(8)
_cell_length_b                   9.7451(14)
_cell_length_c                   15.944(2)
_cell_measurement_reflns_used    7491
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.5506
_cell_measurement_theta_min      3.0927
_cell_volume                     811.6(2)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2005-2013)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2014)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2013)'
_computing_structure_solution    'SHELXS (G. M. Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_radiation_source         1\mS
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24817
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.694
_diffrn_reflns_theta_min         3.582
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.99609
_exptl_absorpt_correction_T_min  0.97795
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       plate
_exptl_crystal_F_000             322
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent:  DMF '
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         5459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0398
_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)+(0.0559P)²+0.2255P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1071
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4519
_reflns_number_total             5459
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00444k2.cif
_cod_data_source_block           10683sadabs
_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_cell_volume        811.5(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7232675
_shelx_shelxl_version_number     2016/6
_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.
;
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.966
_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:
 C4(H4), C6(H6), C7(H7), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.13292(5) 0.66849(3) 0.38994(2) 0.01421(8) Uani 1 1 d .
O1 O 0.49112(16) 0.58678(8) 0.26794(5) 0.01721(16) Uani 1 1 d .
N1 N -0.0935(2) 0.29782(11) 0.36316(7) 0.0219(2) Uani 1 1 d .
C1 C 0.0743(2) 0.36069(11) 0.40234(7) 0.0153(2) Uani 1 1 d .
C2 C 0.2886(2) 0.43457(11) 0.45287(6) 0.01270(19) Uani 1 1 d .
C3 C 0.3434(2) 0.57557(11) 0.44901(7) 0.01277(19) Uani 1 1 d .
C4 C 0.5584(2) 0.63953(11) 0.49661(7) 0.01343(19) Uani 1 1 d .
H4 H 0.601554 0.734597 0.494714 0.016 Uiso 1 1 calc R
C5 C 0.3523(2) 0.78123(11) 0.35182(7) 0.01303(19) Uani 1 1 d .
C6 C 0.3617(2) 0.92357(11) 0.38037(7) 0.0168(2) Uani 1 1 d .
H6 H 0.250651 0.960338 0.420891 0.020 Uiso 1 1 calc R
C7 C 0.5333(2) 1.01189(12) 0.34960(8) 0.0189(2) Uani 1 1 d .
H7 H 0.539416 1.109023 0.368734 0.023 Uiso 1 1 calc R
C8 C 0.6951(2) 0.95734(12) 0.29097(7) 0.0178(2) Uani 1 1 d .
H8 H 0.814007 1.017645 0.270668 0.021 Uiso 1 1 calc R
C9 C 0.6868(2) 0.81531(12) 0.26113(7) 0.0158(2) Uani 1 1 d .
H9 H 0.798076 0.779310 0.220495 0.019 Uiso 1 1 calc R
C10 C 0.5141(2) 0.72674(11) 0.29135(7) 0.01299(19) Uani 1 1 d .
C11 C 0.6305(2) 0.52410(12) 0.19998(7) 0.0173(2) Uani 1 1 d .
H11A H 0.814994 0.538873 0.215715 0.021 Uiso 1 1 calc R
H11B H 0.588774 0.565030 0.147624 0.021 Uiso 1 1 calc R
C12 C 0.5531(2) 0.37054(12) 0.18589(8) 0.0179(2) Uani 1 1 d .
H12A H 0.605271 0.331188 0.238023 0.021 Uiso 1 1 calc R
H12B H 0.645233 0.323612 0.139139 0.021 Uiso 1 1 calc R
C13 C 0.2697(2) 0.33900(12) 0.16402(8) 0.0192(2) Uani 1 1 d .
H13A H 0.225446 0.356003 0.105071 0.023 Uiso 1 1 calc R
H13B H 0.176356 0.403814 0.202391 0.023 Uiso 1 1 calc R
C14 C 0.1828(2) 0.19011(12) 0.17161(8) 0.0185(2) Uani 1 1 d .
H14A H 0.231403 0.173262 0.230315 0.022 Uiso 1 1 calc R
H14B H -0.004418 0.181524 0.163008 0.022 Uiso 1 1 calc R
C15 C 0.2879(2) 0.07684(11) 0.10990(7) 0.0167(2) Uani 1 1 d .
H15A H 0.473652 0.076501 0.122532 0.020 Uiso 1 1 calc R
H15B H 0.254844 0.097109 0.051093 0.020 Uiso 1 1 calc R
C16 C 0.1681(2) -0.06593(11) 0.11624(7) 0.0162(2) Uani 1 1 d .
H16A H 0.202492 -0.085307 0.175189 0.019 Uiso 1 1 calc R
H16B H -0.017789 -0.063940 0.104757 0.019 Uiso 1 1 calc R
C17 C 0.2627(2) -0.18369(12) 0.05547(8) 0.0197(2) Uani 1 1 d .
H17A H 0.447553 -0.188612 0.068110 0.024 Uiso 1 1 calc R
H17B H 0.232868 -0.163767 -0.003537 0.024 Uiso 1 1 calc R
C18 C 0.1320(3) -0.32348(13) 0.06200(9) 0.0244(3) Uani 1 1 d .
H18A H 0.165345 -0.345087 0.119849 0.037 Uiso 1 1 calc GR
H18B H 0.197442 -0.395842 0.021408 0.037 Uiso 1 1 calc GR
H18C H -0.050998 -0.319491 0.048948 0.037 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 0.00 0.0850
-1.00 0.00 0.00 0.0850
0.00 1.00 0.00 0.0300
0.00 -1.00 0.00 0.0300
0.00 0.00 1.00 0.0100
0.00 0.00 -1.00 0.0100
1.00 -1.00 0.00 0.0700
-1.00 -1.00 1.00 0.0700
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
C3 S1 C5 99.91(5) . .
C10 O1 C11 119.19(8) . .
N1 C1 C2 177.62(12) . .
C3 C2 C1 120.51(10) . .
C4 C2 C1 117.85(9) 2_666 .
C4 C2 C3 121.61(10) 2_666 .
C2 C3 S1 120.10(8) . .
C4 C3 S1 122.02(8) . .
C4 C3 C2 117.77(10) . .
C3 C4 C2 120.60(9) . 2_666
C6 C5 S1 120.36(8) . .
C6 C5 C10 120.13(10) . .
C10 C5 S1 119.50(8) . .
C7 C6 C5 120.08(11) . .
C8 C7 C6 119.55(10) . .
C7 C8 C9 121.13(10) . .
C10 C9 C8 119.48(10) . .
O1 C10 C5 115.63(9) . .
O1 C10 C9 124.74(10) . .
C9 C10 C5 119.62(10) . .
O1 C11 C12 106.41(9) . .
C11 C12 C13 113.77(10) . .
C12 C13 C14 113.55(10) . .
C15 C14 C13 115.75(10) . .
C14 C15 C16 111.49(9) . .
C17 C16 C15 114.17(9) . .
C16 C17 C18 112.35(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C3 1.7672(11) .
S1 C5 1.7673(10) .
O1 C10 1.3586(13) .
O1 C11 1.4369(14) .
N1 C1 1.1463(15) .
C1 C2 1.4420(15) .
C2 C3 1.4033(14) .
C2 C4 1.3946(15) 2_666
C3 C4 1.3901(15) .
C5 C6 1.3934(15) .
C5 C10 1.4023(15) .
C6 C7 1.3907(15) .
C7 C8 1.3828(17) .
C8 C9 1.3946(16) .
C9 C10 1.3917(14) .
C11 C12 1.5146(16) .
C12 C13 1.5242(16) .
C13 C14 1.5278(16) .
C14 C15 1.5234(16) .
C15 C16 1.5246(15) .
C16 C17 1.5200(16) .
C17 C18 1.5226(16) .
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.
;
