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#$Date: 2025-08-20 17:59:05 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301833 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/79/4117946.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_4117946
loop_
_publ_author_name
'Lucie Routaboul'
'Pierre Braunstein'
'Jie Xiao'
'Zhengzheng Zhang'
'Peter A. Dowben'
'Guillaume Dalmas'
'Victor Da Costa'
'Olivier Félix'
'Gero Decher'
'Luis G. Rosa'
'Bernard Doudin'
_publ_contact_author_address
;Laboratoire de Chimie de Coordination, 
Institut de Chimie (UMR 7177 CNRS), 
Université Louis Pasteur, 
4 rue Blaise Pascal, F-67070 
Strasbourg Cedex, France, 
;
_publ_contact_author_email       braunstein@unistra.fr
_publ_contact_author_fax         '+33 368851322'
_publ_contact_author_name        'Dr. Pierre Braunstein'
_publ_contact_author_phone       '+33 368851308'
_publ_section_title
;
 Altering the Static Dipole on Surfaces through Chemistry: Molecular Films
 of Zwitterionic Quinonoids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8494
_journal_page_last               8506
_journal_paper_doi               10.1021/ja212104b
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C14 H22 N2 O2 S2'
_chemical_formula_sum            'C14 H22 N2 O2 S2'
_chemical_formula_weight         314.46
_space_group_IT_number           2
_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_creation_method           SHELXL-97
_cell_angle_alpha                104.132(4)
_cell_angle_beta                 91.046(3)
_cell_angle_gamma                94.447(4)
_cell_formula_units_Z            2
_cell_length_a                   5.3008(4)
_cell_length_b                   9.8123(7)
_cell_length_c                   15.3621(9)
_cell_measurement_reflns_used    4182
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      0.988
_cell_volume                     771.94(9)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    ORTEP-3
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0630
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4283
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         3.86
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.040(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0671
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0879P)²+1.2627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1766
_refine_ls_wR_factor_ref         0.1873
_reflns_number_gt                2043
_reflns_number_total             2748
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja212104b_si_002_3.cif
_cod_data_source_block           Lucie1
_cod_database_code               4117946
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
C1 C 1.0805(7) 0.2530(4) 0.3851(3) 0.0228(8) Uani 1 1 d .
H1 H 1.1277 0.2559 0.3262 0.027 Uiso 1 1 calc R
C2 C 0.8893(7) 0.3314(4) 0.4259(2) 0.0212(8) Uani 1 1 d .
C3 C 0.8129(7) 0.3314(4) 0.5204(3) 0.0231(9) Uani 1 1 d .
C4 C 0.9421(7) 0.2482(4) 0.5659(3) 0.0241(9) Uani 1 1 d .
H4 H 0.8957 0.2467 0.6252 0.029 Uiso 1 1 calc R
C5 C 1.1356(7) 0.1679(4) 0.5277(3) 0.0228(8) Uani 1 1 d .
C6 C 1.2027(7) 0.1701(4) 0.4315(3) 0.0219(8) Uani 1 1 d .
C7 C 0.8057(8) 0.4270(4) 0.2972(3) 0.0259(9) Uani 1 1 d .
H7A H 0.8020 0.3327 0.2549 0.031 Uiso 1 1 calc R
H7B H 0.9775 0.4745 0.2974 0.031 Uiso 1 1 calc R
C8 C 0.6140(9) 0.5125(5) 0.2642(3) 0.0336(10) Uani 1 1 d .
H8A H 0.6202 0.6074 0.3057 0.040 Uiso 1 1 calc R
H8B H 0.4418 0.4660 0.2651 0.040 Uiso 1 1 calc R
C9 C 0.6630(9) 0.5278(5) 0.1694(3) 0.0363(11) Uani 1 1 d .
H9A H 0.8405 0.5667 0.1681 0.044 Uiso 1 1 calc R
H9B H 0.5525 0.5977 0.1563 0.044 Uiso 1 1 calc R
C10 C 0.2718(10) 0.3580(6) 0.0665(4) 0.0563(14) Uani 1 1 d .
H10A H 0.1943 0.3418 0.1209 0.084 Uiso 1 1 calc R
H10B H 0.2160 0.2797 0.0151 0.084 Uiso 1 1 calc R
H10C H 0.2203 0.4464 0.0557 0.084 Uiso 1 1 calc R
C11 C 1.4862(7) 0.0620(4) 0.3111(3) 0.0246(9) Uani 1 1 d .
H11A H 1.6733 0.0737 0.3178 0.030 Uiso 1 1 calc R
H11B H 1.4319 0.1329 0.2801 0.030 Uiso 1 1 calc R
C12 C 1.4041(8) -0.0850(4) 0.2540(3) 0.0275(9) Uani 1 1 d .
H12A H 1.4377 -0.1544 0.2890 0.033 Uiso 1 1 calc R
H12B H 1.5094 -0.1043 0.2004 0.033 Uiso 1 1 calc R
C13 C 1.1252(8) -0.1073(5) 0.2226(3) 0.0324(10) Uani 1 1 d .
H13A H 1.0199 -0.0943 0.2761 0.039 Uiso 1 1 calc R
H13B H 1.0891 -0.2059 0.1872 0.039 Uiso 1 1 calc R
C14 C 1.2664(9) -0.0174(6) 0.0714(3) 0.0435(12) Uani 1 1 d .
H14A H 1.4323 0.0230 0.0990 0.065 Uiso 1 1 calc R
H14B H 1.2227 0.0288 0.0240 0.065 Uiso 1 1 calc R
H14C H 1.2726 -0.1187 0.0454 0.065 Uiso 1 1 calc R
O1 O 0.6388(5) 0.4057(3) 0.55222(19) 0.0318(7) Uani 1 1 d .
O2 O 1.2600(5) 0.0931(3) 0.56543(18) 0.0304(7) Uani 1 1 d .
N1 N 0.7568(6) 0.4100(4) 0.3861(2) 0.0248(8) Uani 1 1 d .
N2 N 1.3798(6) 0.0874(3) 0.3993(2) 0.0249(8) Uani 1 1 d .
S1 S 0.6121(2) 0.36894(13) 0.08069(8) 0.0415(4) Uani 1 1 d .
S2 S 1.0313(2) 0.00960(13) 0.15528(7) 0.0357(4) Uani 1 1 d .
H2N H 1.444(8) 0.055(4) 0.436(3) 0.024(12) Uiso 1 1 d .
H1N H 0.660(8) 0.453(4) 0.416(3) 0.021(11) 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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 119.3(3)
N1 C2 C1 123.6(4)
N1 C2 C3 114.7(3)
C1 C2 C3 121.7(3)
O1 C3 C4 124.7(4)
O1 C3 C2 117.5(3)
C4 C3 C2 117.7(3)
C5 C4 C3 122.5(4)
O2 C5 C4 125.4(4)
O2 C5 C6 117.0(3)
C4 C5 C6 117.6(3)
N2 C6 C1 125.2(4)
N2 C6 C5 113.7(3)
C1 C6 C5 121.2(3)
N1 C7 C8 112.6(3)
C7 C8 C9 112.5(3)
C8 C9 S1 116.1(3)
N2 C11 C12 112.0(3)
C11 C12 C13 114.5(3)
C12 C13 S2 114.6(3)
C2 N1 C7 123.0(3)
C6 N2 C11 128.5(4)
C9 S1 C10 100.0(3)
C14 S2 C13 100.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.386(5)
C1 C6 1.392(5)
C2 N1 1.326(5)
C2 C3 1.513(5)
C3 O1 1.253(4)
C3 C4 1.405(5)
C4 C5 1.393(5)
C5 O2 1.256(4)
C5 C6 1.531(5)
C6 N2 1.313(5)
C7 N1 1.442(5)
C7 C8 1.522(5)
C8 C9 1.525(6)
C9 S1 1.801(5)
C10 S1 1.805(5)
C11 N2 1.450(5)
C11 C12 1.520(6)
C12 C13 1.529(6)
C13 S2 1.812(4)
C14 S2 1.796(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660628
2 PubChem 102485755
