#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301863 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/37/7203786.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_7203786
loop_
_publ_author_name
'Nielsen, Mogens Brøndsted'
'Petersen, Jan Conrad'
'Thorup, Niels'
'Jessing, Mikkel'
'Andersson, Asbjørn Sune'
'Jepsen, Anne Sofie'
'Gisselbrecht, Jean-Paul'
'Boudon, Corinne'
'Gross, Maurice'
_publ_section_title
;
 Acetylenic dithiafulvene derived donor--π--acceptor dyads: synthesis,
 electrochemistry and non-linear optical properties
;
_journal_issue                   26
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              2599
_journal_paper_doi               10.1039/b504124d
_journal_volume                  15
_journal_year                    2005
_chemical_formula_moiety         'C16 H11 N O6 S2'
_chemical_formula_sum            'C16 H11 N O6 S2'
_chemical_formula_weight         377.38
_chemical_melting_point          453
_chemical_name_systematic
;
3-[4,5-Bis(methoxycarbonyl)-1,3-dithiol-2-ylidene]-1-(4-nitrophenyl)propyne
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'manual editing of SHELXL-97 cif'
_cell_angle_alpha                90.00
_cell_angle_beta                 99.608(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.5249(19)
_cell_length_b                   5.6048(6)
_cell_length_c                   17.472(2)
_cell_measurement_reflns_used    894
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.277
_cell_measurement_theta_min      7.437
_cell_volume                     1595.5(3)
_computing_cell_refinement       'SAINT 6.02a (Bruker-AXS, 2000)'
_computing_data_collection       'SMART 5.054 (Bruker-AXS, 1999)'
_computing_data_reduction        'SAINT 6.02a (Bruker-AXS, 2000)'
_computing_molecular_graphics
;
'SHELXTL 6.12 (Bruker-AXS, 2001) and PLATON (Spek, 1990)'
;
_computing_structure_refinement  'SHELXTL 6.12 (Bruker-AXS, 2001)'
_computing_structure_solution    'SHELXTL 6.12 (Bruker-AXS, 2001)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens/Bruker SMART 1K'
_diffrn_measurement_method       'omega scan, frame data integration'
_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  0.0877
_diffrn_reflns_av_sigmaI/netI    0.0726
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16297
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.368
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_correction_T_min  0.8518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS ver 2.03 (Sheldrick 2001)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0420
_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)+(0.0464P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0959
_reflns_number_gt                2171
_reflns_number_total             3251
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b504124d.txt
_cod_data_source_block           mbn141k
_cod_database_code               7203786
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.62464(4) 0.21839(12) 0.15692(4) 0.01937(18) Uani 1 1 d . . .
S2 S 0.52592(4) 0.40245(12) 0.26917(4) 0.02072(18) Uani 1 1 d . . .
O1 O 0.43838(10) -0.2144(3) 0.10938(10) 0.0224(4) Uani 1 1 d . . .
O2 O 0.55669(10) -0.1823(3) 0.06221(10) 0.0262(5) Uani 1 1 d . . .
O3 O 0.40813(10) -0.1141(3) 0.26727(10) 0.0211(4) Uani 1 1 d . . .
O4 O 0.34182(10) 0.1800(3) 0.19525(11) 0.0303(5) Uani 1 1 d . . .
O5 O 0.72623(12) 1.7886(4) 0.58890(11) 0.0366(5) Uani 1 1 d . . .
O6 O 0.60152(12) 1.7013(4) 0.60056(11) 0.0362(5) Uani 1 1 d . . .
N1 N 0.66505(15) 1.6623(4) 0.57424(13) 0.0272(6) Uani 1 1 d . . .
C1 C 0.66691(15) 1.4580(5) 0.52249(14) 0.0217(6) Uani 1 1 d . . .
C2 C 0.73748(16) 1.4144(5) 0.49200(15) 0.0238(6) Uani 1 1 d . . .
H2 H 0.7840(16) 1.519(5) 0.5066(14) 0.029(8) Uiso 1 1 d . . .
C3 C 0.73767(16) 1.2306(5) 0.44053(15) 0.0214(6) Uani 1 1 d . . .
H3 H 0.7868(15) 1.195(4) 0.4192(14) 0.024(7) Uiso 1 1 d . . .
C4 C 0.66720(15) 1.0890(5) 0.41920(14) 0.0183(6) Uani 1 1 d . . .
C5 C 0.59767(16) 1.1354(5) 0.45296(16) 0.0232(6) Uani 1 1 d . . .
H5 H 0.5488(14) 1.040(4) 0.4343(13) 0.017(7) Uiso 1 1 d . . .
C6 C 0.59757(17) 1.3182(5) 0.50446(16) 0.0237(6) Uani 1 1 d . . .
H6 H 0.5534(16) 1.354(5) 0.5269(15) 0.026(8) Uiso 1 1 d . . .
C7 C 0.66684(15) 0.9059(5) 0.36241(15) 0.0203(6) Uani 1 1 d . . .
C8 C 0.66791(14) 0.7579(5) 0.31310(15) 0.0199(6) Uani 1 1 d . . .
C9 C 0.67425(16) 0.5912(5) 0.25456(15) 0.0214(6) Uani 1 1 d . . .
H9 H 0.7207(15) 0.600(4) 0.2336(14) 0.019(7) Uiso 1 1 d . . .
C10 C 0.61615(14) 0.4263(4) 0.22965(14) 0.0172(6) Uani 1 1 d . . .
C11 C 0.48713(15) 0.1621(4) 0.21325(14) 0.0175(6) Uani 1 1 d . . .
C12 C 0.53133(14) 0.0765(5) 0.16125(14) 0.0174(6) Uani 1 1 d . . .
C13 C 0.51113(15) -0.1186(5) 0.10552(15) 0.0193(6) Uani 1 1 d . . .
C14 C 0.41519(19) -0.4185(5) 0.05974(18) 0.0246(6) Uani 1 1 d . . .
H14A H 0.3999(16) -0.366(5) 0.0040(17) 0.037(8) Uiso 1 1 d . . .
H14B H 0.3680(17) -0.491(5) 0.0790(16) 0.036(8) Uiso 1 1 d . . .
H14C H 0.4586(16) -0.526(5) 0.0655(14) 0.021(7) Uiso 1 1 d . . .
C15 C 0.40308(15) 0.0776(5) 0.22332(15) 0.0189(6) Uani 1 1 d . . .
C16 C 0.32988(17) -0.2172(6) 0.27774(18) 0.0251(7) Uani 1 1 d . . .
H16A H 0.3022(18) -0.108(6) 0.3156(18) 0.054(10) Uiso 1 1 d . . .
H16B H 0.3437(17) -0.368(5) 0.2981(17) 0.039(9) Uiso 1 1 d . . .
H16C H 0.2936(18) -0.218(5) 0.2280(19) 0.049(9) Uiso 1 1 d . . .
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
C12 S1 C10 95.37(12) . . ?
C11 S2 C10 95.54(12) . . ?
C13 O1 C14 116.1(2) . . ?
C15 O3 C16 115.3(2) . . ?
O5 N1 O6 122.9(2) . . ?
O5 N1 C1 118.7(2) . . ?
O6 N1 C1 118.4(2) . . ?
C2 C1 C6 122.2(3) . . ?
C2 C1 N1 118.9(2) . . ?
C6 C1 N1 118.9(2) . . ?
C3 C2 C1 118.8(3) . . ?
C3 C2 H2 122.8(16) . . ?
C1 C2 H2 118.4(16) . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 120.1(15) . . ?
C4 C3 H3 119.4(15) . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 C7 121.2(2) . . ?
C3 C4 C7 119.8(2) . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 122.6(15) . . ?
C4 C5 H5 116.6(14) . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 H6 122.7(17) . . ?
C1 C6 H6 118.3(17) . . ?
C8 C7 C4 177.6(3) . . ?
C7 C8 C9 176.1(3) . . ?
C10 C9 C8 123.7(2) . . ?
C10 C9 H9 120.9(16) . . ?
C8 C9 H9 115.4(16) . . ?
C9 C10 S1 123.48(19) . . ?
C9 C10 S2 122.1(2) . . ?
S1 C10 S2 114.42(14) . . ?
C12 C11 C15 125.6(2) . . ?
C12 C11 S2 117.98(19) . . ?
C15 C11 S2 116.26(18) . . ?
C11 C12 C13 128.7(2) . . ?
C11 C12 S1 116.69(19) . . ?
C13 C12 S1 114.56(18) . . ?
O2 C13 O1 125.2(2) . . ?
O2 C13 C12 122.7(2) . . ?
O1 C13 C12 112.1(2) . . ?
O1 C14 H14A 110.3(16) . . ?
O1 C14 H14B 105.4(17) . . ?
H14A C14 H14B 111(2) . . ?
O1 C14 H14C 109.0(15) . . ?
H14A C14 H14C 111(2) . . ?
H14B C14 H14C 110(2) . . ?
O4 C15 O3 126.8(2) . . ?
O4 C15 C11 122.4(2) . . ?
O3 C15 C11 110.8(2) . . ?
O3 C16 H16A 109.5(17) . . ?
O3 C16 H16B 104.0(18) . . ?
H16A C16 H16B 113(2) . . ?
O3 C16 H16C 108.6(18) . . ?
H16A C16 H16C 107(2) . . ?
H16B C16 H16C 115(3) . . ?
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 C12 1.748(2) . ?
S1 C10 1.747(3) . ?
S2 C11 1.724(3) . ?
S2 C10 1.750(2) . ?
O1 C13 1.329(3) . ?
O1 C14 1.448(3) . ?
O2 C13 1.207(3) . ?
O3 C15 1.315(3) . ?
O3 C16 1.455(3) . ?
O4 C15 1.195(3) . ?
O5 N1 1.226(3) . ?
O6 N1 1.234(3) . ?
N1 C1 1.462(3) . ?
C1 C2 1.382(4) . ?
C1 C6 1.381(4) . ?
C2 C3 1.368(4) . ?
C2 H2 0.97(3) . ?
C3 C4 1.407(3) . ?
C3 H3 0.97(3) . ?
C4 C5 1.401(3) . ?
C4 C7 1.427(4) . ?
C5 C6 1.364(4) . ?
C5 H5 0.98(2) . ?
C6 H6 0.91(3) . ?
C7 C8 1.198(4) . ?
C8 C9 1.402(4) . ?
C9 C10 1.352(3) . ?
C9 H9 0.91(3) . ?
C11 C12 1.346(3) . ?
C11 C15 1.505(3) . ?
C12 C13 1.465(4) . ?
C14 H14A 1.01(3) . ?
C14 H14B 0.99(3) . ?
C14 H14C 0.93(3) . ?
C16 H16A 1.06(3) . ?
C16 H16B 0.93(3) . ?
C16 H16C 0.97(3) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 N1 C1 C2 0.0(4) . . . . ?
O6 N1 C1 C2 179.3(2) . . . . ?
O5 N1 C1 C6 -178.6(2) . . . . ?
O6 N1 C1 C6 0.6(4) . . . . ?
C6 C1 C2 C3 1.9(4) . . . . ?
N1 C1 C2 C3 -176.7(2) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 -1.6(4) . . . . ?
C2 C3 C4 C7 176.7(2) . . . . ?
C3 C4 C5 C6 1.4(4) . . . . ?
C7 C4 C5 C6 -176.9(2) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
C2 C1 C6 C5 -2.1(4) . . . . ?
N1 C1 C6 C5 176.5(2) . . . . ?
C5 C4 C7 C8 135(7) . . . . ?
C3 C4 C7 C8 -44(7) . . . . ?
C4 C7 C8 C9 35(10) . . . . ?
C7 C8 C9 C10 -178(100) . . . . ?
C8 C9 C10 S1 -179.8(2) . . . . ?
C8 C9 C10 S2 -0.5(4) . . . . ?
C12 S1 C10 C9 178.6(2) . . . . ?
C12 S1 C10 S2 -0.71(15) . . . . ?
C11 S2 C10 C9 -178.4(2) . . . . ?
C11 S2 C10 S1 0.97(16) . . . . ?
C10 S2 C11 C12 -1.0(2) . . . . ?
C10 S2 C11 C15 -176.71(19) . . . . ?
C15 C11 C12 C13 -2.4(4) . . . . ?
S2 C11 C12 C13 -177.7(2) . . . . ?
C15 C11 C12 S1 175.9(2) . . . . ?
S2 C11 C12 S1 0.6(3) . . . . ?
C10 S1 C12 C11 0.1(2) . . . . ?
C10 S1 C12 C13 178.67(19) . . . . ?
C14 O1 C13 O2 3.1(4) . . . . ?
C14 O1 C13 C12 -176.3(2) . . . . ?
C11 C12 C13 O2 -178.8(3) . . . . ?
S1 C12 C13 O2 2.8(3) . . . . ?
C11 C12 C13 O1 0.7(4) . . . . ?
S1 C12 C13 O1 -177.74(17) . . . . ?
C16 O3 C15 O4 4.2(4) . . . . ?
C16 O3 C15 C11 -177.2(2) . . . . ?
C12 C11 C15 O4 -98.4(3) . . . . ?
S2 C11 C15 O4 77.0(3) . . . . ?
C12 C11 C15 O3 83.0(3) . . . . ?
S2 C11 C15 O3 -101.6(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21143293
2 PubChem 139195248
