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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/43/4124308.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_4124308
loop_
_publ_author_name
'Ren, Longbin'
'Liu, Feng'
'Shen, Xingxing'
'Zhang, Cheng'
'Yi, Yuanping'
'Zhu, Xiaozhang'
_publ_section_title
;
 Developing Quinoidal Fluorophores with Unusually Strong Red/Near-Infrared
 Emission.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11294
_journal_page_last               11302
_journal_paper_doi               10.1021/jacs.5b03899
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C34 H36 Cl2 N2 O4 S4'
_chemical_formula_weight         735.79
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.45(3)
_cell_angle_beta                 82.55(3)
_cell_angle_gamma                89.45(3)
_cell_formula_units_Z            1
_cell_length_a                   5.4021(11)
_cell_length_b                   8.6247(17)
_cell_length_c                   19.004(4)
_cell_measurement_reflns_used    1847
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      25.1209
_cell_measurement_theta_min      2.2148
_cell_volume                     856.8(3)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1089
_diffrn_reflns_av_sigmaI/netI    0.2115
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5884
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.475
_exptl_absorpt_correction_T_max  0.9541
_exptl_absorpt_correction_T_min  0.9111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.130
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2839
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1607
_refine_ls_R_factor_gt           0.1201
_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)+(0.1542P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2965
_refine_ls_wR_factor_ref         0.3247
_reflns_number_gt                1363
_reflns_number_total             2839
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b03899_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

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

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4124308.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4124308
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 1.4729(5) 0.4750(3) -0.20060(11) 0.0365(7) Uani 1 1 d .
S1 S 1.7506(4) 0.0228(3) 0.09955(11) 0.0272(6) Uani 1 1 d U
S2 S 1.8170(4) 0.2351(3) -0.13132(12) 0.0302(7) Uani 1 1 d .
O1 O 1.4704(12) 0.0379(8) 0.2285(3) 0.0343(16) Uani 1 1 d .
O2 O 1.1179(12) 0.1856(7) 0.2384(3) 0.0338(16) Uani 1 1 d .
N1 N 1.0044(14) 0.4109(10) 0.0821(4) 0.0338(19) Uani 1 1 d .
C1 C 1.5523(17) 0.3564(10) -0.1230(4) 0.028(2) Uani 1 1 d .
C2 C 1.4453(17) 0.3408(11) -0.0532(4) 0.0262(19) Uani 1 1 d U
H2 H 1.3042 0.3991 -0.0392 0.031 Uiso 1 1 calc R
C3 C 1.5678(16) 0.2265(10) -0.0022(4) 0.0242(19) Uani 1 1 d U
C4 C 1.5238(17) 0.1642(11) 0.0742(4) 0.029(2) Uani 1 1 d U
C5 C 1.8984(16) 0.0455(11) 0.0097(5) 0.028(2) Uani 1 1 d .
C6 C 1.7692(17) 0.1620(11) -0.0387(4) 0.028(2) Uani 1 1 d U
C7 C 1.3371(16) 0.2016(11) 0.1238(5) 0.030(2) Uani 1 1 d .
C8 C 1.1529(16) 0.3176(11) 0.1000(4) 0.029(2) Uani 1 1 d .
C9 C 1.3158(18) 0.1314(12) 0.2010(5) 0.034(2) Uani 1 1 d .
C10 C 1.0900(18) 0.1367(12) 0.3181(4) 0.037(2) Uani 1 1 d .
H10A H 1.2224 0.1873 0.3374 0.044 Uiso 1 1 calc R
H10B H 1.1033 0.0200 0.3333 0.044 Uiso 1 1 calc R
C11 C 0.8392(17) 0.1880(12) 0.3464(5) 0.038(2) Uani 1 1 d .
H11A H 0.7091 0.1201 0.3354 0.046 Uiso 1 1 calc R
H11B H 0.8130 0.2989 0.3212 0.046 Uiso 1 1 calc R
C12 C 0.8103(18) 0.1778(12) 0.4286(5) 0.041(3) Uani 1 1 d .
H12A H 0.8403 0.0674 0.4536 0.049 Uiso 1 1 calc R
H12B H 0.9387 0.2473 0.4394 0.049 Uiso 1 1 calc R
C13 C 0.5557(17) 0.2264(11) 0.4583(4) 0.035(2) Uani 1 1 d .
H13A H 0.4294 0.1486 0.4531 0.041 Uiso 1 1 calc R
H13B H 0.5168 0.3312 0.4289 0.041 Uiso 1 1 calc R
C14 C 0.5358(17) 0.2367(12) 0.5380(4) 0.036(2) Uani 1 1 d .
H14A H 0.6645 0.3127 0.5435 0.043 Uiso 1 1 calc R
H14B H 0.5703 0.1313 0.5677 0.043 Uiso 1 1 calc R
C15 C 0.2741(18) 0.2909(12) 0.5674(5) 0.037(2) Uani 1 1 d .
H15A H 0.1476 0.2098 0.5659 0.044 Uiso 1 1 calc R
H15B H 0.2334 0.3914 0.5349 0.044 Uiso 1 1 calc R
C16 C 0.2571(17) 0.3166(12) 0.6465(5) 0.036(2) Uani 1 1 d .
H16A H 0.3018 0.2172 0.6791 0.044 Uiso 1 1 calc R
H16B H 0.3787 0.4005 0.6480 0.044 Uiso 1 1 calc R
C17 C -0.0037(19) 0.3642(13) 0.6738(5) 0.045(3) Uani 1 1 d .
H17A H -0.0510 0.4603 0.6406 0.067 Uiso 1 1 calc R
H17B H -0.0053 0.3852 0.7225 0.067 Uiso 1 1 calc R
H17C H -0.1227 0.2778 0.6758 0.067 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'
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'
Cl Cl 0.1484 0.1585 '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
C4 S1 C5 93.0(4) .
C6 S2 C1 89.3(4) .
C9 O2 C10 117.4(7) .
C2 C1 Cl1 129.7(7) .
C2 C1 S2 112.8(7) .
Cl1 C1 S2 117.5(5) .
C1 C2 C3 113.1(8) .
C1 C2 H2 123.4 .
C3 C2 H2 123.4 .
C6 C3 C4 115.0(8) .
C6 C3 C2 110.1(7) .
C4 C3 C2 134.8(8) .
C7 C4 C3 128.2(9) .
C7 C4 S1 122.3(6) .
C3 C4 S1 109.5(6) .
C5 C5 C6 127.1(10) 2_955
C5 C5 S1 122.9(10) 2_955
C6 C5 S1 109.9(6) .
C3 C6 C5 112.6(7) .
C3 C6 S2 114.7(7) .
C5 C6 S2 132.7(7) .
C4 C7 C8 120.1(8) .
C4 C7 C9 122.8(9) .
C8 C7 C9 117.0(8) .
N1 C8 C7 178.8(8) .
O1 C9 O2 124.9(8) .
O1 C9 C7 123.0(9) .
O2 C9 C7 112.0(8) .
O2 C10 C11 107.4(7) .
O2 C10 H10A 110.2 .
C11 C10 H10A 110.2 .
O2 C10 H10B 110.2 .
C11 C10 H10B 110.2 .
H10A C10 H10B 108.5 .
C10 C11 C12 112.3(8) .
C10 C11 H11A 109.1 .
C12 C11 H11A 109.1 .
C10 C11 H11B 109.1 .
C12 C11 H11B 109.1 .
H11A C11 H11B 107.9 .
C13 C12 C11 112.9(8) .
C13 C12 H12A 109.0 .
C11 C12 H12A 109.0 .
C13 C12 H12B 109.0 .
C11 C12 H12B 109.0 .
H12A C12 H12B 107.8 .
C12 C13 C14 113.3(7) .
C12 C13 H13A 108.9 .
C14 C13 H13A 108.9 .
C12 C13 H13B 108.9 .
C14 C13 H13B 108.9 .
H13A C13 H13B 107.7 .
C13 C14 C15 112.7(7) .
C13 C14 H14A 109.1 .
C15 C14 H14A 109.1 .
C13 C14 H14B 109.1 .
C15 C14 H14B 109.1 .
H14A C14 H14B 107.8 .
C14 C15 C16 113.5(7) .
C14 C15 H15A 108.9 .
C16 C15 H15A 108.9 .
C14 C15 H15B 108.9 .
C16 C15 H15B 108.9 .
H15A C15 H15B 107.7 .
C17 C16 C15 111.6(8) .
C17 C16 H16A 109.3 .
C15 C16 H16A 109.3 .
C17 C16 H16B 109.3 .
C15 C16 H16B 109.3 .
H16A C16 H16B 108.0 .
C16 C17 H17A 109.5 .
C16 C17 H17B 109.5 .
H17A C17 H17B 109.5 .
C16 C17 H17C 109.5 .
H17A C17 H17C 109.5 .
H17B C17 H17C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1 1.705(8) .
S1 C4 1.758(10) .
S1 C5 1.760(8) .
S2 C6 1.722(8) .
S2 C1 1.774(9) .
O1 C9 1.240(11) .
O2 C9 1.343(11) .
O2 C10 1.470(9) .
N1 C8 1.160(11) .
C1 C2 1.355(11) .
C2 C3 1.444(11) .
C2 H2 0.9500 .
C3 C6 1.391(12) .
C3 C4 1.425(10) .
C4 C7 1.374(11) .
C5 C5 1.401(16) 2_955
C5 C6 1.446(12) .
C7 C8 1.448(12) .
C7 C9 1.450(12) .
C10 C11 1.491(11) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.532(11) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.509(11) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.528(10) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.557(12) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.559(11) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.521(12) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C6 S2 C1 C2 1.4(7) . .
C6 S2 C1 Cl1 -179.7(5) . .
Cl1 C1 C2 C3 179.9(7) . .
S2 C1 C2 C3 -1.4(9) . .
C1 C2 C3 C6 0.6(10) . .
C1 C2 C3 C4 -177.1(9) . .
C6 C3 C4 C7 -178.3(8) . .
C2 C3 C4 C7 -0.7(16) . .
C6 C3 C4 S1 1.2(10) . .
C2 C3 C4 S1 178.8(8) . .
C5 S1 C4 C7 179.0(8) . .
C5 S1 C4 C3 -0.5(7) . .
C4 S1 C5 C5 -176.8(10) . 2_955
C4 S1 C5 C6 -0.2(7) . .
C4 C3 C6 C5 -1.4(11) . .
C2 C3 C6 C5 -179.6(7) . .
C4 C3 C6 S2 178.8(6) . .
C2 C3 C6 S2 0.5(9) . .
C5 C5 C6 C3 177.4(11) 2_955 .
S1 C5 C6 C3 0.9(10) . .
C5 C5 C6 S2 -2.8(18) 2_955 .
S1 C5 C6 S2 -179.2(6) . .
C1 S2 C6 C3 -1.1(7) . .
C1 S2 C6 C5 179.1(9) . .
C3 C4 C7 C8 0.2(14) . .
S1 C4 C7 C8 -179.2(7) . .
C3 C4 C7 C9 -178.7(8) . .
S1 C4 C7 C9 1.9(12) . .
C4 C7 C8 N1 -159(47) . .
C9 C7 C8 N1 20(47) . .
C10 O2 C9 O1 3.3(13) . .
C10 O2 C9 C7 -173.7(7) . .
C4 C7 C9 O1 3.3(14) . .
C8 C7 C9 O1 -175.7(8) . .
C4 C7 C9 O2 -179.6(8) . .
C8 C7 C9 O2 1.4(11) . .
C9 O2 C10 C11 -170.7(7) . .
O2 C10 C11 C12 -167.1(8) . .
C10 C11 C12 C13 -178.9(8) . .
C11 C12 C13 C14 -172.8(9) . .
C12 C13 C14 C15 178.6(8) . .
C13 C14 C15 C16 -174.9(8) . .
C14 C15 C16 C17 -178.2(8) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168333369
