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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/11/7221127.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_7221127
loop_
_publ_author_name
'Salmerón-Valverde, Amparo'
'Bernès, Sylvain'
_publ_section_title
;
 Crystal growth and characterization of solvated organic charge-transfer
 complexes built on TTF and 9-dicyanomethylenefluorene derivatives
;
_journal_issue                   32
_journal_name_full               CrystEngComm
_journal_page_first              6227
_journal_paper_doi               10.1039/C5CE01059D
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C17 H5 N5 O8, C6 H4 S4, H2 O'
_chemical_formula_sum            'C23 H11 N5 O9 S4'
_chemical_formula_weight         629.61
_chemical_melting_point          509
_chemical_name_systematic
'Tetrathiafulvalene 9-dicyanomethylene-4,5,7-trinitrofluorene-2-carboxylic acid monohydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-30
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-03-23 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.572(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9432(14)
_cell_length_b                   12.1351(9)
_cell_length_c                   13.5738(11)
_cell_measurement_reflns_used    79
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12.40
_cell_measurement_theta_min      4.80
_cell_volume                     2541.7(4)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics
;
SHELXTL-Plus (Siemens, 1996) and MERCURY (Macrae et al., 2008)
;
_computing_publication_material  SHELXL-2014/7
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6560
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.135
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30
_diffrn_source_power             1.5
_diffrn_source_type              FN4
_diffrn_source_voltage           50
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.439
_exptl_absorpt_correction_T_max  0.33615
_exptl_absorpt_correction_T_min  0.28602
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'XSCANS (Siemens, 1996)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_description       needle
_exptl_crystal_F_000             1280
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CH3CN'
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.912
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2918
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0699P)²+5.6211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1448
_refine_ls_wR_factor_ref         0.1511
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2476
_reflns_number_total             2918
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ce01059d2.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 7221123--7221128.cif.'
_cod_database_code               7221127
_shelx_shelxl_version_number     2014/7
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.66001(17) 0.5337(2) 0.8326(2) 0.0365(6) Uani 1 1 d . . . . .
H1A H 0.6766 0.4603 0.8436 0.044 Uiso 1 1 calc R U . . .
C2 C 0.72027(18) 0.6177(3) 0.8617(2) 0.0415(6) Uani 1 1 d D . . . .
C3 C 0.6975(2) 0.7261(3) 0.8409(2) 0.0474(7) Uani 1 1 d . . . . .
H3A H 0.7390 0.7813 0.8583 0.057 Uiso 1 1 calc R U . . .
C4 C 0.6129(2) 0.7524(2) 0.7943(2) 0.0456(7) Uani 1 1 d . . . . .
C5 C 0.54710(17) 0.6727(2) 0.77071(19) 0.0334(5) Uani 1 1 d . . . . .
C6 C 0.57429(16) 0.5611(2) 0.78657(19) 0.0315(5) Uani 1 1 d . . . . .
C7 C 0.5000 0.4882(3) 0.7500 0.0297(7) Uani 1 2 d S T P . .
C8 C 0.5000 0.3753(3) 0.7500 0.0344(8) Uani 1 2 d S T P . .
C9 C 0.57790(19) 0.3103(2) 0.7761(2) 0.0424(6) Uani 1 1 d . . . . .
N10 N 0.6388(2) 0.2568(3) 0.7946(3) 0.0663(8) Uani 1 1 d . . . . .
C11A C 0.8104(9) 0.5914(10) 0.9166(13) 0.051(7) Uani 0.5 1 d D . P A 1
O12A O 0.8330(13) 0.4931(13) 0.9211(17) 0.115(7) Uani 0.5 1 d D . P A 1
O13A O 0.8553(14) 0.6735(15) 0.9588(18) 0.084(6) Uani 0.5 1 d D . P A 1
H13A H 0.905(3) 0.651(4) 0.996(5) 0.126 Uiso 0.5 1 d D U P B 1
N11B N 0.8102(7) 0.5864(11) 0.9166(12) 0.072(8) Uani 0.5 1 d D . P A 2
O12B O 0.8239(9) 0.4845(8) 0.9341(10) 0.053(2) Uani 0.5 1 d D . P A 2
O13B O 0.8663(13) 0.6562(12) 0.9382(16) 0.068(4) Uani 0.5 1 d D . P A 2
N14 N 0.5972(2) 0.8675(3) 0.7570(3) 0.0655(8) Uani 1 1 d . . . . .
O15 O 0.5414(2) 0.8818(2) 0.6742(2) 0.0744(8) Uani 1 1 d . . . . .
O16 O 0.6418(2) 0.9397(2) 0.8099(3) 0.0931(11) Uani 1 1 d . . . . .
S17 S 0.63982(5) 0.47940(6) 0.56837(6) 0.0419(2) Uani 1 1 d . . . . .
C18 C 0.6905(2) 0.6071(3) 0.5831(2) 0.0499(7) Uani 1 1 d . . . . .
H18A H 0.7499 0.6135 0.6108 0.060 Uiso 1 1 calc R U . . .
C19 C 0.6415(2) 0.6952(3) 0.5536(3) 0.0527(8) Uani 1 1 d . . . . .
H19A H 0.6656 0.7654 0.5589 0.063 Uiso 1 1 calc R U . . .
S20 S 0.53055(5) 0.67557(6) 0.50444(6) 0.0456(2) Uani 1 1 d . . . . .
C21 C 0.53581(17) 0.5328(2) 0.5157(2) 0.0368(6) Uani 1 1 d . . . . .
O22 O 1.0273(4) 0.5827(4) 0.9393(5) 0.0763(17) Uani 0.5 1 d D . P . .
H22A H 0.995(5) 0.527(5) 0.921(8) 0.114 Uiso 0.5 1 d D U P . .
H22B H 1.070(4) 0.563(8) 0.987(6) 0.114 Uiso 0.5 1 d D U P . .
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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 3 -1
4 0 -8
-4 0 8
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 C6 118.9(3) . .
C2 C1 H1A 120.6 . .
C6 C1 H1A 120.6 . .
C3 C2 C1 121.0(3) . .
C3 C2 C11A 118.9(6) . .
C1 C2 C11A 120.0(6) . .
C3 C2 N11B 121.2(6) . .
C1 C2 N11B 117.7(6) . .
C2 C3 C4 119.7(3) . .
C2 C3 H3A 120.2 . .
C4 C3 H3A 120.2 . .
C3 C4 C5 122.4(3) . .
C3 C4 N14 115.9(3) . .
C5 C4 N14 121.2(3) . .
C4 C5 C6 116.1(2) . .
C4 C5 C5 136.31(17) . 2_656
C6 C5 C5 107.58(15) . 2_656
C1 C6 C5 121.5(2) . .
C1 C6 C7 128.9(2) . .
C5 C6 C7 109.6(2) . .
C8 C7 C6 127.23(15) . .
C8 C7 C6 127.23(15) . 2_656
C6 C7 C6 105.5(3) . 2_656
C7 C8 C9 123.24(17) . .
C7 C8 C9 123.24(17) . 2_656
C9 C8 C9 113.5(3) . 2_656
N10 C9 C8 178.1(4) . .
O12A C11A O13A 127.3(16) . .
O12A C11A C2 117.7(13) . .
O13A C11A C2 114.9(14) . .
C11A O13A H13A 110(3) . .
O13B N11B O12B 123.6(13) . .
O13B N11B C2 120.1(14) . .
O12B N11B C2 116.2(10) . .
O16 N14 O15 126.4(3) . .
O16 N14 C4 116.4(3) . .
O15 N14 C4 117.1(3) . .
C18 S17 C21 94.72(15) . .
C19 C18 S17 117.6(2) . .
C19 C18 H18A 121.2 . .
S17 C18 H18A 121.2 . .
C18 C19 S20 118.1(3) . .
C18 C19 H19A 121.0 . .
S20 C19 H19A 121.0 . .
C21 S20 C19 94.63(15) . .
C21 C21 S20 122.2(3) 5_666 .
C21 C21 S17 122.7(3) 5_666 .
S20 C21 S17 115.01(15) . .
H22A O22 H22B 108(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.388(4) .
C1 C6 1.392(4) .
C1 H1A 0.9300 .
C2 C3 1.375(5) .
C2 C11A 1.478(12) .
C2 N11B 1.489(11) .
C3 C4 1.374(5) .
C3 H3A 0.9300 .
C4 C5 1.404(4) .
C4 N14 1.485(4) .
C5 C6 1.422(3) .
C5 C5 1.465(5) 2_656
C6 C7 1.461(3) .
C7 C8 1.370(5) .
C7 C6 1.461(3) 2_656
C8 C9 1.438(4) .
C8 C9 1.438(4) 2_656
C9 N10 1.142(4) .
C11A O12A 1.243(15) .
C11A O13A 1.275(18) .
O13A H13A 0.88(2) .
N11B O13B 1.212(15) .
N11B O12B 1.268(13) .
N14 O16 1.239(4) .
N14 O15 1.258(4) .
S17 C18 1.736(3) .
S17 C21 1.756(3) .
C18 C19 1.326(5) .
C18 H18A 0.9300 .
C19 S20 1.742(3) .
C19 H19A 0.9300 .
S20 C21 1.740(3) .
C21 C21 1.369(5) 5_666
O22 H22A 0.85(2) .
O22 H22B 0.85(2) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O13A H13A O22 0.88(2) 2.41(6) 3.03(2) 128(6) .
O22 H22A O15 0.85(2) 2.18(6) 2.944(6) 150(11) 4_646
O22 H22A O22 0.85(2) 2.41(10) 2.869(14) 115(9) 5_767
O22 H22B O12A 0.85(2) 1.85(3) 2.697(19) 173(11) 5_767
O22 H22B O12B 0.85(2) 1.85(4) 2.682(11) 167(12) 5_767
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 C1 C2 C3 -3.5(4) . .
C6 C1 C2 C11A 176.1(9) . .
C6 C1 C2 N11B 176.2(8) . .
C1 C2 C3 C4 2.7(5) . .
C11A C2 C3 C4 -176.9(9) . .
N11B C2 C3 C4 -177.0(8) . .
C2 C3 C4 C5 2.9(5) . .
C2 C3 C4 N14 -168.7(3) . .
C3 C4 C5 C6 -7.3(4) . .
N14 C4 C5 C6 164.0(3) . .
C3 C4 C5 C5 174.9(4) . 2_656
N14 C4 C5 C5 -13.9(6) . 2_656
C2 C1 C6 C5 -1.2(4) . .
C2 C1 C6 C7 -179.8(2) . .
C4 C5 C6 C1 6.4(4) . .
C5 C5 C6 C1 -175.2(3) 2_656 .
C4 C5 C6 C7 -174.8(2) . .
C5 C5 C6 C7 3.6(3) 2_656 .
C1 C6 C7 C8 -2.7(3) . .
C5 C6 C7 C8 178.59(13) . .
C1 C6 C7 C6 177.3(3) . 2_656
C5 C6 C7 C6 -1.41(13) . 2_656
C6 C7 C8 C9 -7.84(19) . .
C6 C7 C8 C9 172.16(19) 2_656 .
C6 C7 C8 C9 172.16(19) . 2_656
C6 C7 C8 C9 -7.84(19) 2_656 2_656
C3 C2 C11A O12A -169.4(15) . .
C1 C2 C11A O12A 11(2) . .
C3 C2 C11A O13A 14.0(19) . .
C1 C2 C11A O13A -165.6(13) . .
C3 C2 N11B O13B -5(2) . .
C1 C2 N11B O13B 175.6(15) . .
C3 C2 N11B O12B 178.4(11) . .
C1 C2 N11B O12B -1.4(17) . .
C3 C4 N14 O16 -36.1(5) . .
C5 C4 N14 O16 152.1(4) . .
C3 C4 N14 O15 142.6(3) . .
C5 C4 N14 O15 -29.2(5) . .
C21 S17 C18 C19 -0.2(3) . .
S17 C18 C19 S20 1.0(4) . .
C18 C19 S20 C21 -1.2(3) . .
C19 S20 C21 C21 -178.1(3) . 5_666
C19 S20 C21 S17 1.06(19) . .
C18 S17 C21 C21 178.5(3) . 5_666
C18 S17 C21 S20 -0.67(19) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139200529
