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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/85/4508581.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_4508581
loop_
_publ_author_name
'Camerel, Franck'
'Le Helloco, Guillaume'
'Guizouarn, Thierry'
'Jeannin, Olivier'
'Fourmigué, Marc'
'Frąckowiak, Arkadiusz'
'Olejniczak, Iwona'
'Świetlik, Roman'
'Marino, Andrea'
'Collet, Eric'
'Toupet, Loic'
'Auban-Senzier, Pascale'
'Canadell, Enric'
_publ_section_title
;
 Correlation between Metal--Insulator Transition and Hydrogen-Bonding
 Network in the Organic Metal
 δ-(BEDT-TTF)4[2,6-Anthracene-bis(sulfonate)]·(H2O)4
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5135
_journal_paper_doi               10.1021/cg401416h
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C24 H20 P, 0.5(C10 H6 O6 S2)'
_chemical_formula_sum            'C29 H23 O3 P S'
_chemical_formula_weight         482.51
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.3500(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2340(3)
_cell_length_b                   7.0165(2)
_cell_length_c                   26.8821(6)
_cell_measurement_reflns_used    8161
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.00
_cell_volume                     2283.09(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            18505
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0409
_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)+(0.0486P)²+1.7234P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1110
_reflns_number_gt                4542
_reflns_number_total             5222
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401416h_si_002.cif
_cod_data_source_block           TPP2NBS
_cod_original_sg_symbol_H-M      P21/n
_cod_original_formula_sum        'C29 H23 O3 P S '
_cod_database_code               4508581
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
C1 C 1.50199(14) -0.4564(3) 0.06903(7) 0.0287(4) Uani 1 1 d .
H1 H 1.5199 -0.5207 0.0994 0.034 Uiso 1 1 calc R
C2 C 1.46383(13) -0.2745(3) 0.06912(7) 0.0258(4) Uani 1 1 d .
C3 C 1.43344(15) -0.1770(3) 0.02271(7) 0.0308(4) Uani 1 1 d .
H3 H 1.4062 -0.0533 0.0229 0.037 Uiso 1 1 calc R
C4 C 1.44368(15) -0.2625(3) -0.02206(7) 0.0307(4) Uani 1 1 d .
H4 H 1.4233 -0.1971 -0.0521 0.037 Uiso 1 1 calc R
C5 C 1.48494(13) -0.4490(3) -0.02276(7) 0.0257(4) Uani 1 1 d .
C6 C 1.06184(13) 0.2914(2) 0.11572(6) 0.0182(3) Uani 1 1 d .
C7 C 1.00932(15) 0.4410(2) 0.08744(7) 0.0245(4) Uani 1 1 d .
H7 H 0.9334 0.4572 0.0854 0.029 Uiso 1 1 calc R
C8 C 1.07048(16) 0.5655(3) 0.06237(7) 0.0292(4) Uani 1 1 d .
H8 H 1.0354 0.6636 0.0430 0.035 Uiso 1 1 calc R
C9 C 1.18390(16) 0.5436(3) 0.06624(7) 0.0303(4) Uani 1 1 d .
H9 H 1.2250 0.6282 0.0498 0.036 Uiso 1 1 calc R
C10 C 1.23631(15) 0.3962(3) 0.09446(7) 0.0300(4) Uani 1 1 d .
H10 H 1.3125 0.3826 0.0970 0.036 Uiso 1 1 calc R
C11 C 1.17574(13) 0.2680(3) 0.11911(6) 0.0227(3) Uani 1 1 d .
H11 H 1.2110 0.1679 0.1376 0.027 Uiso 1 1 calc R
C12 C 1.05579(12) -0.0269(2) 0.18875(6) 0.0176(3) Uani 1 1 d .
C13 C 1.12838(14) -0.1516(2) 0.16945(6) 0.0229(3) Uani 1 1 d .
H13 H 1.1363 -0.1463 0.1356 0.028 Uiso 1 1 calc R
C14 C 1.18835(15) -0.2827(3) 0.20073(7) 0.0274(4) Uani 1 1 d .
H14 H 1.2386 -0.3625 0.1882 0.033 Uiso 1 1 calc R
C15 C 1.17332(15) -0.2948(3) 0.25087(7) 0.0289(4) Uani 1 1 d .
H15 H 1.2116 -0.3863 0.2715 0.035 Uiso 1 1 calc R
C16 C 1.10177(15) -0.1716(3) 0.27031(6) 0.0265(4) Uani 1 1 d .
H16 H 1.0928 -0.1801 0.3040 0.032 Uiso 1 1 calc R
C17 C 1.04327(13) -0.0352(2) 0.23964(6) 0.0213(3) Uani 1 1 d .
H17 H 0.9964 0.0494 0.2528 0.026 Uiso 1 1 calc R
C18 C 0.89444(13) -0.0087(2) 0.09880(6) 0.0188(3) Uani 1 1 d .
C19 C 0.88973(14) 0.0266(3) 0.04762(6) 0.0242(4) Uani 1 1 d .
H19 H 0.9327 0.1225 0.0365 0.029 Uiso 1 1 calc R
C20 C 0.82027(16) -0.0824(3) 0.01325(7) 0.0322(4) Uani 1 1 d .
H20 H 0.8169 -0.0597 -0.0210 0.039 Uiso 1 1 calc R
C21 C 0.75625(15) -0.2244(3) 0.02999(7) 0.0309(4) Uani 1 1 d .
H21 H 0.7093 -0.2960 0.0069 0.037 Uiso 1 1 calc R
C22 C 0.76147(14) -0.2607(3) 0.08067(7) 0.0296(4) Uani 1 1 d .
H22 H 0.7183 -0.3569 0.0916 0.035 Uiso 1 1 calc R
C23 C 0.83074(14) -0.1544(3) 0.11538(7) 0.0258(4) Uani 1 1 d .
H23 H 0.8349 -0.1798 0.1496 0.031 Uiso 1 1 calc R
C24 C 0.88617(13) 0.2770(2) 0.17689(6) 0.0192(3) Uani 1 1 d .
C25 C 0.77210(14) 0.2768(3) 0.16171(6) 0.0242(4) Uani 1 1 d .
H25 H 0.7404 0.1956 0.1363 0.029 Uiso 1 1 calc R
C26 C 0.70648(15) 0.4001(3) 0.18516(7) 0.0289(4) Uani 1 1 d .
H26 H 0.6305 0.4027 0.1750 0.035 Uiso 1 1 calc R
C27 C 0.75377(16) 0.5189(3) 0.22349(7) 0.0295(4) Uani 1 1 d .
H27 H 0.7094 0.6024 0.2385 0.035 Uiso 1 1 calc R
C28 C 0.86689(16) 0.5144(3) 0.23963(8) 0.0317(4) Uani 1 1 d .
H28 H 0.8977 0.5908 0.2663 0.038 Uiso 1 1 calc R
C29 C 0.93332(14) 0.3960(3) 0.21594(7) 0.0266(4) Uani 1 1 d .
H29 H 1.0093 0.3954 0.2259 0.032 Uiso 1 1 calc R
O1 O 1.34283(13) -0.0710(3) 0.11830(7) 0.0578(5) Uani 1 1 d .
O2 O 1.53800(14) -0.0025(3) 0.12901(6) 0.0481(4) Uani 1 1 d .
O3 O 1.47193(16) -0.2900(3) 0.16519(6) 0.0534(5) Uani 1 1 d .
P1 P 0.97656(3) 0.13281(6) 0.145803(15) 0.01618(11) Uani 1 1 d .
S1 S 1.45334(4) -0.14776(7) 0.125756(18) 0.02993(13) Uani 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
C2 C1 C5 121.06(17) . 3_845
C2 C1 H1 119.5 . .
C5 C1 H1 119.5 3_845 .
C1 C2 C3 119.71(18) . .
C1 C2 S1 122.46(14) . .
C3 C2 S1 117.80(15) . .
C4 C3 C2 120.99(19) . .
C4 C3 H3 119.5 . .
C2 C3 H3 119.5 . .
C3 C4 C5 120.02(17) . .
C3 C4 H4 120.0 . .
C5 C4 H4 120.0 . .
C4 C5 C5 120.5(2) . 3_845
C4 C5 C1 121.80(16) . 3_845
C5 C5 C1 117.7(2) 3_845 3_845
C11 C6 C7 120.07(15) . .
C11 C6 P1 122.58(13) . .
C7 C6 P1 117.34(12) . .
C8 C7 C6 119.98(16) . .
C8 C7 H7 120.0 . .
C6 C7 H7 120.0 . .
C9 C8 C7 119.94(17) . .
C9 C8 H8 120.0 . .
C7 C8 H8 120.0 . .
C10 C9 C8 120.24(17) . .
C10 C9 H9 119.9 . .
C8 C9 H9 119.9 . .
C9 C10 C11 120.48(17) . .
C9 C10 H10 119.8 . .
C11 C10 H10 119.8 . .
C6 C11 C10 119.28(17) . .
C6 C11 H11 120.4 . .
C10 C11 H11 120.4 . .
C13 C12 C17 120.14(15) . .
C13 C12 P1 117.75(12) . .
C17 C12 P1 122.04(12) . .
C14 C13 C12 119.98(16) . .
C14 C13 H13 120.0 . .
C12 C13 H13 120.0 . .
C13 C14 C15 119.83(16) . .
C13 C14 H14 120.1 . .
C15 C14 H14 120.1 . .
C16 C15 C14 120.51(16) . .
C16 C15 H15 119.7 . .
C14 C15 H15 119.7 . .
C15 C16 C17 120.29(16) . .
C15 C16 H16 119.9 . .
C17 C16 H16 119.9 . .
C16 C17 C12 119.19(16) . .
C16 C17 H17 120.4 . .
C12 C17 H17 120.4 . .
C19 C18 C23 120.07(15) . .
C19 C18 P1 122.41(13) . .
C23 C18 P1 117.47(13) . .
C20 C19 C18 119.52(16) . .
C20 C19 H19 120.2 . .
C18 C19 H19 120.2 . .
C21 C20 C19 120.04(17) . .
C21 C20 H20 120.0 . .
C19 C20 H20 120.0 . .
C22 C21 C20 120.52(17) . .
C22 C21 H21 119.7 . .
C20 C21 H21 119.7 . .
C21 C22 C23 120.17(17) . .
C21 C22 H22 119.9 . .
C23 C22 H22 119.9 . .
C22 C23 C18 119.65(17) . .
C22 C23 H23 120.2 . .
C18 C23 H23 120.2 . .
C25 C24 C29 120.39(15) . .
C25 C24 P1 121.42(13) . .
C29 C24 P1 118.15(12) . .
C26 C25 C24 119.01(16) . .
C26 C25 H25 120.5 . .
C24 C25 H25 120.5 . .
C27 C26 C25 120.32(17) . .
C27 C26 H26 119.8 . .
C25 C26 H26 119.8 . .
C26 C27 C28 120.54(17) . .
C26 C27 H27 119.7 . .
C28 C27 H27 119.7 . .
C29 C28 C27 119.74(18) . .
C29 C28 H28 120.1 . .
C27 C28 H28 120.1 . .
C28 C29 C24 119.94(17) . .
C28 C29 H29 120.0 . .
C24 C29 H29 120.0 . .
C12 P1 C24 111.45(7) . .
C12 P1 C18 107.64(7) . .
C24 P1 C18 108.68(7) . .
C12 P1 C6 112.50(7) . .
C24 P1 C6 107.35(8) . .
C18 P1 C6 109.15(7) . .
O1 S1 O2 113.18(12) . .
O1 S1 O3 113.78(11) . .
O2 S1 O3 113.95(11) . .
O1 S1 C2 104.46(9) . .
O2 S1 C2 105.26(8) . .
O3 S1 C2 104.96(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.359(3) .
C1 C5 1.439(3) 3_845
C1 H1 0.9300 .
C2 C3 1.424(2) .
C2 S1 1.7837(19) .
C3 C4 1.367(3) .
C3 H3 0.9300 .
C4 C5 1.404(3) .
C4 H4 0.9300 .
C5 C5 1.419(3) 3_845
C5 C1 1.439(3) 3_845
C6 C11 1.393(2) .
C6 C7 1.397(2) .
C6 P1 1.7962(16) .
C7 C8 1.387(2) .
C7 H7 0.9300 .
C8 C9 1.385(3) .
C8 H8 0.9300 .
C9 C10 1.384(3) .
C9 H9 0.9300 .
C10 C11 1.393(2) .
C10 H10 0.9300 .
C11 H11 0.9300 .
C12 C13 1.399(2) .
C12 C17 1.400(2) .
C12 P1 1.7899(16) .
C13 C14 1.383(2) .
C13 H13 0.9300 .
C14 C15 1.389(3) .
C14 H14 0.9300 .
C15 C16 1.386(3) .
C15 H15 0.9300 .
C16 C17 1.392(2) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C18 C19 1.391(2) .
C18 C23 1.397(2) .
C18 P1 1.7953(16) .
C19 C20 1.390(2) .
C19 H19 0.9300 .
C20 C21 1.383(3) .
C20 H20 0.9300 .
C21 C22 1.378(3) .
C21 H21 0.9300 .
C22 C23 1.384(2) .
C22 H22 0.9300 .
C23 H23 0.9300 .
C24 C25 1.396(2) .
C24 C29 1.398(2) .
C24 P1 1.7926(16) .
C25 C26 1.392(2) .
C25 H25 0.9300 .
C26 C27 1.385(3) .
C26 H26 0.9300 .
C27 C28 1.389(3) .
C27 H27 0.9300 .
C28 C29 1.381(2) .
C28 H28 0.9300 .
C29 H29 0.9300 .
O1 S1 1.4421(16) .
O2 S1 1.4468(16) .
O3 S1 1.4495(16) .
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
C5 C1 C2 C3 1.7(2) 3_845 .
C5 C1 C2 S1 -176.60(12) 3_845 .
C1 C2 C3 C4 -1.1(3) . .
S1 C2 C3 C4 177.29(14) . .
C2 C3 C4 C5 -0.2(3) . .
C3 C4 C5 C5 0.7(3) . 3_845
C3 C4 C5 C1 -179.42(16) . 3_845
C11 C6 C7 C8 0.5(3) . .
P1 C6 C7 C8 -178.49(13) . .
C6 C7 C8 C9 -1.3(3) . .
C7 C8 C9 C10 0.9(3) . .
C8 C9 C10 C11 0.2(3) . .
C7 C6 C11 C10 0.6(2) . .
P1 C6 C11 C10 179.58(13) . .
C9 C10 C11 C6 -1.0(3) . .
C17 C12 C13 C14 -0.3(2) . .
P1 C12 C13 C14 -177.55(13) . .
C12 C13 C14 C15 2.3(3) . .
C13 C14 C15 C16 -2.5(3) . .
C14 C15 C16 C17 0.6(3) . .
C15 C16 C17 C12 1.4(3) . .
C13 C12 C17 C16 -1.5(2) . .
P1 C12 C17 C16 175.58(13) . .
C23 C18 C19 C20 0.8(3) . .
P1 C18 C19 C20 -176.83(14) . .
C18 C19 C20 C21 0.2(3) . .
C19 C20 C21 C22 -0.7(3) . .
C20 C21 C22 C23 0.3(3) . .
C21 C22 C23 C18 0.7(3) . .
C19 C18 C23 C22 -1.2(3) . .
P1 C18 C23 C22 176.51(14) . .
C29 C24 C25 C26 1.6(3) . .
P1 C24 C25 C26 -176.13(13) . .
C24 C25 C26 C27 -1.0(3) . .
C25 C26 C27 C28 -1.1(3) . .
C26 C27 C28 C29 2.6(3) . .
C27 C28 C29 C24 -2.0(3) . .
C25 C24 C29 C28 -0.1(3) . .
P1 C24 C29 C28 177.67(15) . .
C13 C12 P1 C24 178.61(12) . .
C17 C12 P1 C24 1.45(16) . .
C13 C12 P1 C18 59.53(14) . .
C17 C12 P1 C18 -117.63(14) . .
C13 C12 P1 C6 -60.75(14) . .
C17 C12 P1 C6 122.08(14) . .
C25 C24 P1 C12 -122.10(14) . .
C29 C24 P1 C12 60.13(15) . .
C25 C24 P1 C18 -3.65(16) . .
C29 C24 P1 C18 178.58(13) . .
C25 C24 P1 C6 114.28(14) . .
C29 C24 P1 C6 -63.49(15) . .
C19 C18 P1 C12 -131.03(14) . .
C23 C18 P1 C12 51.30(15) . .
C19 C18 P1 C24 108.14(15) . .
C23 C18 P1 C24 -69.53(15) . .
C19 C18 P1 C6 -8.64(16) . .
C23 C18 P1 C6 173.68(13) . .
C11 C6 P1 C12 10.61(16) . .
C7 C6 P1 C12 -170.38(12) . .
C11 C6 P1 C24 133.57(14) . .
C7 C6 P1 C24 -47.42(15) . .
C11 C6 P1 C18 -108.80(14) . .
C7 C6 P1 C18 70.21(14) . .
C1 C2 S1 O1 -130.62(16) . .
C3 C2 S1 O1 51.09(16) . .
C1 C2 S1 O2 109.94(16) . .
C3 C2 S1 O2 -68.36(16) . .
C1 C2 S1 O3 -10.63(17) . .
C3 C2 S1 O3 171.08(14) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146714
