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#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/84/2228488.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_2228488
loop_
_publ_author_name
'Hou, Rui-Bin'
'Yin, Bing-Zhu'
_publ_section_title
;
 2-[4,5-Bis(butylsulfanyl)-1,3-dithiol-2-ylidene]-5-methyl-5H-1,3-dithiolo[4,5-c]pyrrole-4-carbaldehyde
;
_journal_coeditor_code           NG5074
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3353
_journal_paper_doi               10.1107/S160053681004910X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H23 N O S6'
_chemical_formula_moiety         'C18 H23 N O S6'
_chemical_formula_sum            'C18 H23 N O S6'
_chemical_formula_weight         461.73
_chemical_name_systematic
;
2-[4,5-Bis(butylsulfanyl)-1,3-dithiol-2-ylidene]-5-methyl-5H-
1,3-dithiolo[4,5-c]pyrrole-4-carbaldehyde
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_cell_angle_alpha                93.44(3)
_cell_angle_beta                 99.37(3)
_cell_angle_gamma                105.31(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4227(15)
_cell_length_b                   8.8356(18)
_cell_length_c                   17.811(4)
_cell_measurement_reflns_used    7048
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      3.17
_cell_volume                     1105.1(5)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10707
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.16
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  0.9399
_exptl_absorpt_correction_T_min  0.9285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.440
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0514
_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)+(0.1030P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1760
_reflns_number_gt                3298
_reflns_number_total             4956
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng5074.cif
_cod_data_source_block           I
_cod_original_cell_volume        1105.1(4)
_cod_database_code               2228488
_cod_database_fobs_code          2228488
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 1.3588(7) 0.8577(6) 0.3605(3) 0.0992(16) Uani d . 1 . .
H H1A 1.4403 0.8569 0.3239 0.149 Uiso calc R 1 . .
H H1B 1.4309 0.8665 0.4113 0.149 Uiso calc R 1 . .
H H1C 1.3067 0.9459 0.3554 0.149 Uiso calc R 1 . .
C C2 1.2000(6) 0.7069(5) 0.3463(2) 0.0746(11) Uani d . 1 . .
H H2A 1.2529 0.6206 0.3598 0.090 Uiso calc R 1 . .
H H2B 1.1120 0.7139 0.3802 0.090 Uiso calc R 1 . .
C C3 1.0910(6) 0.6676(5) 0.2657(2) 0.0685(10) Uani d . 1 . .
H H3A 1.0039 0.5628 0.2612 0.082 Uiso calc R 1 . .
H H3B 1.1798 0.6642 0.2317 0.082 Uiso calc R 1 . .
C C4 0.9789(5) 0.7804(5) 0.2387(2) 0.0612(9) Uani d . 1 . .
H H4A 0.9227 0.7494 0.1851 0.073 Uiso calc R 1 . .
H H4B 1.0656 0.8853 0.2429 0.073 Uiso calc R 1 . .
C C5 1.0794(8) 0.1668(7) 0.4134(3) 0.1074(17) Uani d . 1 . .
H H5A 1.0622 0.1460 0.3588 0.161 Uiso calc R 1 . .
H H5B 1.1150 0.0815 0.4370 0.161 Uiso calc R 1 . .
H H5C 1.1778 0.2634 0.4305 0.161 Uiso calc R 1 . .
C C6 0.8994(9) 0.1813(7) 0.4347(3) 0.1053(17) Uani d . 1 . .
H H6A 0.7974 0.0886 0.4120 0.126 Uiso calc R 1 . .
H H6B 0.9111 0.1849 0.4899 0.126 Uiso calc R 1 . .
C C7 0.8498(7) 0.3235(6) 0.4094(3) 0.0837(13) Uani d . 1 . .
H H7A 0.8372 0.3194 0.3542 0.100 Uiso calc R 1 . .
H H7B 0.9524 0.4161 0.4317 0.100 Uiso calc R 1 . .
C C8 0.6652(7) 0.3397(5) 0.4319(2) 0.0735(11) Uani d . 1 . .
H H8A 0.6734 0.3350 0.4866 0.088 Uiso calc R 1 . .
H H8B 0.5604 0.2521 0.4059 0.088 Uiso calc R 1 . .
C C9 0.6295(5) 0.6022(4) 0.26157(16) 0.0458(7) Uani d . 1 . .
C C10 0.5642(5) 0.4948(4) 0.30804(17) 0.0483(7) Uani d . 1 . .
C C11 0.4100(4) 0.3654(3) 0.17027(16) 0.0445(7) Uani d . 1 . .
C C12 0.3512(4) 0.2543(3) 0.10934(16) 0.0438(7) Uani d . 1 . .
C C13 0.2413(4) -0.0068(3) 0.02430(17) 0.0440(7) Uani d . 1 . .
C C14 0.3053(4) 0.1071(3) -0.02319(16) 0.0439(7) Uani d . 1 . .
C C15 0.2900(5) 0.0300(4) -0.09493(18) 0.0525(8) Uani d . 1 . .
H H15 0.3207 0.0776 -0.1381 0.063 Uiso calc R 1 . .
C C16 0.1719(6) -0.2460(5) -0.1579(2) 0.0688(10) Uani d . 1 . .
H H16A 0.0363 -0.2788 -0.1743 0.103 Uiso calc R 1 . .
H H16B 0.2154 -0.3354 -0.1440 0.103 Uiso calc R 1 . .
H H16C 0.2307 -0.2022 -0.1989 0.103 Uiso calc R 1 . .
C C17 0.1886(5) -0.1548(4) -0.01838(19) 0.0510(7) Uani d . 1 . .
C C18 0.1247(6) -0.3038(4) 0.0080(2) 0.0639(9) Uani d . 1 . .
H H18 0.0960 -0.3934 -0.0267 0.077 Uiso calc R 1 . .
N N1 0.2228(4) -0.1257(3) -0.09119(15) 0.0526(7) Uani d . 1 . .
O O1 0.1051(5) -0.3211(3) 0.07376(16) 0.0820(9) Uani d . 1 . .
S S1 0.79120(13) 0.78869(10) 0.29159(5) 0.0561(3) Uani d . 1 . .
S S2 0.61844(16) 0.52311(12) 0.40750(5) 0.0659(3) Uani d . 1 . .
S S3 0.38334(14) 0.32527(10) 0.26366(5) 0.0567(3) Uani d . 1 . .
S S4 0.52382(14) 0.56342(9) 0.16415(4) 0.0536(2) Uani d . 1 . .
S S5 0.37538(13) 0.30352(9) 0.01664(4) 0.0524(2) Uani d . 1 . .
S S6 0.24240(13) 0.05437(9) 0.11878(4) 0.0516(2) Uani d . 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 C1 . . 115.1(4) ?
C3 C2 H2A . . 108.5 ?
C1 C2 H2A . . 108.5 ?
C3 C2 H2B . . 108.5 ?
C1 C2 H2B . . 108.5 ?
H2A C2 H2B . . 107.5 ?
C2 C3 C4 . . 115.4(3) ?
C2 C3 H3A . . 108.4 ?
C4 C3 H3A . . 108.4 ?
C2 C3 H3B . . 108.4 ?
C4 C3 H3B . . 108.4 ?
H3A C3 H3B . . 107.5 ?
C3 C4 S1 . . 114.2(3) ?
C3 C4 H4A . . 108.7 ?
S1 C4 H4A . . 108.7 ?
C3 C4 H4B . . 108.7 ?
S1 C4 H4B . . 108.7 ?
H4A C4 H4B . . 107.6 ?
C6 C5 H5A . . 109.5 ?
C6 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C6 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C7 C6 C5 . . 112.5(5) ?
C7 C6 H6A . . 109.1 ?
C5 C6 H6A . . 109.1 ?
C7 C6 H6B . . 109.1 ?
C5 C6 H6B . . 109.1 ?
H6A C6 H6B . . 107.8 ?
C6 C7 C8 . . 112.7(4) ?
C6 C7 H7A . . 109.0 ?
C8 C7 H7A . . 109.0 ?
C6 C7 H7B . . 109.0 ?
C8 C7 H7B . . 109.0 ?
H7A C7 H7B . . 107.8 ?
C7 C8 S2 . . 111.8(3) ?
C7 C8 H8A . . 109.3 ?
S2 C8 H8A . . 109.3 ?
C7 C8 H8B . . 109.3 ?
S2 C8 H8B . . 109.3 ?
H8A C8 H8B . . 107.9 ?
C10 C9 S1 . . 125.3(2) ?
C10 C9 S4 . . 117.4(2) ?
S1 C9 S4 . . 116.88(18) ?
C9 C10 S2 . . 125.1(3) ?
C9 C10 S3 . . 116.0(2) ?
S2 C10 S3 . . 118.30(19) ?
C12 C11 S4 . . 123.3(2) ?
C12 C11 S3 . . 123.5(2) ?
S4 C11 S3 . . 113.19(16) ?
C11 C12 S5 . . 121.2(2) ?
C11 C12 S6 . . 121.7(2) ?
S5 C12 S6 . . 117.09(16) ?
C14 C13 C17 . . 108.2(3) ?
C14 C13 S6 . . 118.5(2) ?
C17 C13 S6 . . 133.4(3) ?
C15 C14 C13 . . 107.6(3) ?
C15 C14 S5 . . 135.4(2) ?
C13 C14 S5 . . 117.0(2) ?
N1 C15 C14 . . 107.9(3) ?
N1 C15 H15 . . 126.0 ?
C14 C15 H15 . . 126.0 ?
N1 C16 H16A . . 109.5 ?
N1 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
N1 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N1 C17 C13 . . 105.7(3) ?
N1 C17 C18 . . 126.9(3) ?
C13 C17 C18 . . 127.3(3) ?
O1 C18 C17 . . 123.6(3) ?
O1 C18 H18 . . 118.2 ?
C17 C18 H18 . . 118.2 ?
C15 N1 C17 . . 110.6(3) ?
C15 N1 C16 . . 124.0(3) ?
C17 N1 C16 . . 125.0(3) ?
C9 S1 C4 . . 101.26(16) ?
C10 S2 C8 . . 102.69(17) ?
C11 S3 C10 . . 94.65(15) ?
C11 S4 C9 . . 94.30(15) ?
C14 S5 C12 . . 93.61(14) ?
C13 S6 C12 . . 93.09(14) ?
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
C1 C2 . 1.504(6) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.500(5) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.510(5) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 S1 . 1.818(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.482(7) ?
C5 H5A . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
C6 C7 . 1.475(7) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.528(6) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 S2 . 1.807(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.342(5) ?
C9 S1 . 1.756(3) ?
C9 S4 . 1.757(3) ?
C10 S2 . 1.739(3) ?
C10 S3 . 1.767(3) ?
C11 C12 . 1.350(4) ?
C11 S4 . 1.749(3) ?
C11 S3 . 1.753(3) ?
C12 S5 . 1.757(3) ?
C12 S6 . 1.769(3) ?
C13 C14 . 1.391(4) ?
C13 C17 . 1.399(4) ?
C13 S6 . 1.734(3) ?
C14 C15 . 1.385(4) ?
C14 S5 . 1.744(3) ?
C15 N1 . 1.344(4) ?
C15 H15 . 0.9300 ?
C16 N1 . 1.475(4) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 N1 . 1.387(4) ?
C17 C18 . 1.413(5) ?
C18 O1 . 1.217(5) ?
C18 H18 . 0.9300 ?
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
C3 H3B O1 1_665 0.97 2.79 3.444(5) 125.0
C4 H4A O1 1_665 0.97 2.71 3.368(5) 125.9
C18 H18 O1 2_545 0.93 2.58 3.412(5) 149.6
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656382
2 PubChem 101907530
