#------------------------------------------------------------------------------
#$Date: 2015-12-09 14:22:45 +0200 (Wed, 09 Dec 2015) $
#$Revision: 171014 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/18/7221842.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_7221842
loop_
_publ_author_name
'Martin, Lee'
'Yang, Songjie'
'Brooks, Andrew C.'
'Horton, Peter N.'
'Male, Louise'
'Moulfi, Ourida'
'Harmand, Lydie'
'Day, Peter'
'Clegg, William'
'Harrington, Ross W.'
'Wallis, John D.'
_publ_section_title
;
 Contrasting crystal packing arrangements in triiodide salts of radical
 cations of chiral bis(pyrrolo[3,4-d])tetrathiafulvalenes
;
_journal_issue                   38
_journal_name_full               CrystEngComm
_journal_page_first              7354
_journal_paper_doi               10.1039/C5CE01430A
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C40 H31 Cl I3 N2 S4'
_chemical_formula_weight         1084.06
_chemical_name_systematic
'Bis(R-N-(1-naphthyl)ethylpyrrolo)tetrathiafulvalenetriiodide chlorobenzene solvate 12.I3.PhCl'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-07-19 deposited with the CCDC.
2015-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 123.371(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.3842(14)
_cell_length_b                   9.0879(2)
_cell_length_c                   19.4801(9)
_cell_measurement_reflns_used    6624
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.9122
_cell_measurement_theta_min      2.9468
_cell_volume                     3900.8(4)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)   
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SHELX-s
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_laue_measured_fraction_full 0.983
_diffrn_reflns_laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9095
_diffrn_reflns_point_group_measured_fraction_full 0.725
_diffrn_reflns_point_group_measured_fraction_max 0.624
_diffrn_reflns_theta_full        27.000
_diffrn_reflns_theta_max         28.980
_diffrn_reflns_theta_min         2.953
_exptl_absorpt_coefficient_mu    2.719
_exptl_absorpt_correction_T_max  0.821
_exptl_absorpt_correction_T_min  0.313
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_description       plate
_exptl_crystal_F_000             2100
_exptl_crystal_recrystallization_method electrocrystallisation
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.871
_refine_diff_density_min         -0.862
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         6467
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0280
_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)+(0.0376P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0662
_refine_ls_wR_factor_ref         0.0675
_reflns_Friedel_coverage         0.366
_reflns_friedel_fraction_full    0.433
_reflns_friedel_fraction_max     0.356
_reflns_number_gt                5804
_reflns_number_total             6467
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ce01430a1.cif
_cod_data_source_block           OU1JWC
_cod_depositor_comments
'Adding full bibliography for 7221839--7221844.cif.'
_cod_database_code               7221842
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
I1 I 0.5000 0.28170(6) 0.5000 0.01860(11) Uani 1 2 d S T P
I2 I 0.47549(2) 0.28162(4) 0.33401(2) 0.02362(10) Uani 1 1 d . . .
I3 I 0.5000 0.31091(6) 0.0000 0.02418(13) Uani 1 2 d S T P
I4 I 0.47220(2) 0.30937(5) 0.12724(2) 0.03058(11) Uani 1 1 d . . .
Cl1 Cl 0.77952(10) 0.5058(2) 0.52605(11) 0.0464(5) Uani 1 1 d . . .
S1 S 0.43263(9) 0.62627(16) 0.54813(11) 0.0177(4) Uani 1 1 d . . .
S2 S 0.43078(9) 0.95300(17) 0.54225(10) 0.0175(4) Uani 1 1 d . . .
S3 S 0.42039(9) 0.61621(16) 0.37636(10) 0.0160(3) Uani 1 1 d . . .
S4 S 0.42128(9) 0.94323(16) 0.37246(10) 0.0172(4) Uani 1 1 d . . .
N1 N 0.42752(19) 0.8035(6) 0.7280(2) 0.0155(9) Uani 1 1 d . . .
N2 N 0.4021(2) 0.7681(5) 0.1755(2) 0.0153(9) Uani 1 1 d . . .
C1 C 0.4268(2) 0.7871(7) 0.4962(3) 0.0154(10) Uani 1 1 d . . .
C2 C 0.4230(2) 0.7830(7) 0.4212(3) 0.0151(10) Uani 1 1 d . . .
C3 C 0.4326(3) 0.7180(6) 0.6265(4) 0.0161(14) Uani 1 1 d . . .
C4 C 0.4307(3) 0.8735(6) 0.6224(4) 0.0153(14) Uani 1 1 d . . .
C5 C 0.4107(3) 0.6967(7) 0.2883(4) 0.0151(13) Uani 1 1 d . . .
C6 C 0.4132(3) 0.8524(6) 0.2891(4) 0.0169(14) Uani 1 1 d . . .
C7 C 0.4299(3) 0.6755(7) 0.6923(4) 0.0178(15) Uani 1 1 d . . .
H7 H 0.4296 0.5778 0.7095 0.021 Uiso 1 1 calc R U .
C8 C 0.4274(4) 0.9222(7) 0.6867(4) 0.0207(16) Uani 1 1 d . . .
H8 H 0.4254 1.0219 0.6996 0.025 Uiso 1 1 calc R U .
C9 C 0.4033(3) 0.6482(7) 0.2180(4) 0.0170(14) Uani 1 1 d . . .
H9 H 0.3996 0.5485 0.2012 0.020 Uiso 1 1 calc R U .
C10 C 0.4069(3) 0.8954(7) 0.2162(4) 0.0189(15) Uani 1 1 d . . .
H10 H 0.4061 0.9932 0.1984 0.023 Uiso 1 1 calc R U .
C11 C 0.4115(2) 0.8134(7) 0.7902(3) 0.0183(12) Uani 1 1 d . . .
H11 H 0.4304 0.9055 0.8226 0.022 Uiso 1 1 calc R U .
C12 C 0.3901(3) 0.7584(7) 0.0919(3) 0.0181(13) Uani 1 1 d . . .
H12 H 0.4090 0.6655 0.0886 0.022 Uiso 1 1 calc R U .
C13 C 0.4375(3) 0.6844(7) 0.8505(4) 0.0240(15) Uani 1 1 d . . .
H13A H 0.4196 0.5922 0.8206 0.036 Uiso 1 1 calc R U .
H13B H 0.4278 0.6972 0.8920 0.036 Uiso 1 1 calc R U .
H13C H 0.4816 0.6810 0.8774 0.036 Uiso 1 1 calc R U .
C14 C 0.4195(3) 0.8869(7) 0.0760(4) 0.0239(14) Uani 1 1 d . . .
H14A H 0.3967 0.9772 0.0686 0.036 Uiso 1 1 calc R U .
H14B H 0.4191 0.8675 0.0263 0.036 Uiso 1 1 calc R U .
H14C H 0.4614 0.8985 0.1230 0.036 Uiso 1 1 calc R U .
C15 C 0.3429(3) 0.8265(6) 0.7491(3) 0.0177(12) Uani 1 1 d . . .
C16 C 0.3037(3) 0.7497(7) 0.6788(3) 0.0240(14) Uani 1 1 d . . .
H16 H 0.3194 0.6913 0.6541 0.029 Uiso 1 1 calc R U .
C17 C 0.2401(3) 0.7556(7) 0.6420(4) 0.0284(16) Uani 1 1 d . . .
H17 H 0.2136 0.7043 0.5922 0.034 Uiso 1 1 calc R U .
C18 C 0.2171(3) 0.8345(7) 0.6779(4) 0.0273(15) Uani 1 1 d . . .
H18 H 0.1746 0.8361 0.6539 0.033 Uiso 1 1 calc R U .
C19 C 0.2561(3) 0.9145(7) 0.7509(4) 0.0216(14) Uani 1 1 d . . .
C20 C 0.2328(4) 0.9973(8) 0.7890(4) 0.0289(16) Uani 1 1 d . . .
H20 H 0.1905 0.9946 0.7665 0.035 Uiso 1 1 calc R U .
C21 C 0.2688(4) 1.0799(7) 0.8562(4) 0.0315(17) Uani 1 1 d . . .
H21 H 0.2516 1.1354 0.8798 0.038 Uiso 1 1 calc R U .
C22 C 0.3315(4) 1.0846(7) 0.8916(4) 0.0279(17) Uani 1 1 d . . .
H22 H 0.3566 1.1451 0.9381 0.034 Uiso 1 1 calc R U .
C23 C 0.3566(3) 1.0020(7) 0.8589(3) 0.0218(14) Uani 1 1 d . . .
H23 H 0.3994 1.0030 0.8845 0.026 Uiso 1 1 calc R U .
C24 C 0.3198(3) 0.9142(6) 0.7871(4) 0.0193(13) Uani 1 1 d . . .
C25 C 0.3220(3) 0.7514(6) 0.0260(3) 0.0166(12) Uani 1 1 d . . .
C26 C 0.2814(3) 0.8247(7) 0.0362(3) 0.0194(12) Uani 1 1 d . . .
H26 H 0.2956 0.8765 0.0860 0.023 Uiso 1 1 calc R U .
C27 C 0.2184(3) 0.8249(7) -0.0261(3) 0.0219(13) Uani 1 1 d . . .
H27 H 0.1909 0.8758 -0.0175 0.026 Uiso 1 1 calc R U .
C28 C 0.1972(3) 0.7521(7) -0.0985(3) 0.0222(14) Uani 1 1 d . . .
H28 H 0.1550 0.7523 -0.1400 0.027 Uiso 1 1 calc R U .
C29 C 0.2382(3) 0.6761(6) -0.1118(3) 0.0174(13) Uani 1 1 d . . .
C30 C 0.2165(3) 0.5990(7) -0.1869(4) 0.0262(15) Uani 1 1 d . . .
H30 H 0.1746 0.6026 -0.2294 0.031 Uiso 1 1 calc R U .
C31 C 0.2550(4) 0.5208(7) -0.1983(4) 0.0293(17) Uani 1 1 d . . .
H31 H 0.2399 0.4710 -0.2488 0.035 Uiso 1 1 calc R U .
C32 C 0.3171(4) 0.5128(7) -0.1360(4) 0.0252(16) Uani 1 1 d . . .
H32 H 0.3433 0.4542 -0.1440 0.030 Uiso 1 1 calc R U .
C33 C 0.3402(3) 0.5887(7) -0.0640(4) 0.0218(14) Uani 1 1 d . . .
H33 H 0.3825 0.5860 -0.0234 0.026 Uiso 1 1 calc R U .
C34 C 0.3010(3) 0.6722(6) -0.0493(3) 0.0167(12) Uani 1 1 d . . .
C35 C 0.7326(4) 0.4027(7) 0.4382(4) 0.0326(17) Uani 1 1 d . . .
C36 C 0.6723(4) 0.3822(7) 0.4126(4) 0.0349(18) Uani 1 1 d . . .
H36 H 0.6580 0.4186 0.4448 0.042 Uiso 1 1 calc R U .
C37 C 0.6341(3) 0.3095(8) 0.3409(4) 0.0363(16) Uani 1 1 d . . .
H37 H 0.5926 0.2972 0.3220 0.044 Uiso 1 1 calc R U .
C38 C 0.6555(4) 0.2541(8) 0.2959(5) 0.0410(19) Uani 1 1 d . . .
H38 H 0.6283 0.2044 0.2458 0.049 Uiso 1 1 calc R U .
C39 C 0.7155(3) 0.2689(9) 0.3217(4) 0.0392(17) Uani 1 1 d . . .
H39 H 0.7299 0.2266 0.2910 0.047 Uiso 1 1 calc R U .
C40 C 0.7540(4) 0.3456(8) 0.3926(5) 0.0384(18) Uani 1 1 d . . .
H40 H 0.7952 0.3596 0.4104 0.046 Uiso 1 1 calc R U .
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'
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'
I I -0.4742 1.8119 '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_3
I2 I1 I2 179.97(2) 2_656
I4 I3 I4 179.45(3) 2_655
C1 S1 C3 93.8(3) .
C4 S2 C1 94.3(3) .
C2 S3 C5 94.1(3) .
C2 S4 C6 93.8(3) .
C8 N1 C7 111.2(4) .
C8 N1 C11 122.0(5) .
C7 N1 C11 125.1(5) .
C9 N2 C10 111.1(4) .
C9 N2 C12 122.8(5) .
C10 N2 C12 125.7(5) .
C2 C1 S2 120.7(5) .
C2 C1 S1 121.1(5) .
S2 C1 S1 118.1(3) .
C1 C2 S4 120.9(5) .
C1 C2 S3 120.4(5) .
S4 C2 S3 118.7(3) .
C7 C3 C4 108.2(6) .
C7 C3 S1 135.1(5) .
C4 C3 S1 116.6(6) .
C8 C4 C3 106.8(7) .
C8 C4 S2 136.3(5) .
C3 C4 S2 116.8(6) .
C9 C5 C6 108.6(6) .
C9 C5 S3 136.2(5) .
C6 C5 S3 115.2(5) .
C10 C6 C5 106.8(6) .
C10 C6 S4 135.1(5) .
C5 C6 S4 118.0(5) .
N1 C7 C3 105.9(5) .
N1 C8 C4 107.8(5) .
C5 C9 N2 107.4(5) .
N2 C10 C6 106.0(5) .
N1 C11 C13 111.8(5) .
N1 C11 C15 111.3(4) .
C13 C11 C15 111.2(5) .
N2 C12 C14 110.6(5) .
N2 C12 C25 111.6(4) .
C14 C12 C25 110.8(5) .
C16 C15 C24 119.9(6) .
C16 C15 C11 120.6(5) .
C24 C15 C11 119.4(5) .
C15 C16 C17 121.3(6) .
C18 C17 C16 120.0(6) .
C17 C18 C19 120.4(6) .
C18 C19 C20 121.1(6) .
C18 C19 C24 120.4(6) .
C20 C19 C24 118.5(6) .
C21 C20 C19 122.0(7) .
C20 C21 C22 120.4(7) .
C23 C22 C21 119.9(6) .
C22 C23 C24 121.3(6) .
C19 C24 C23 117.8(6) .
C19 C24 C15 117.9(5) .
C23 C24 C15 124.3(6) .
C26 C25 C34 119.8(5) .
C26 C25 C12 120.7(5) .
C34 C25 C12 119.5(5) .
C25 C26 C27 121.3(5) .
C28 C27 C26 120.2(5) .
C27 C28 C29 120.1(6) .
C34 C29 C28 120.2(5) .
C34 C29 C30 119.2(6) .
C28 C29 C30 120.6(6) .
C31 C30 C29 120.8(6) .
C30 C31 C32 120.7(6) .
C33 C32 C31 120.5(7) .
C32 C33 C34 120.6(6) .
C29 C34 C33 118.2(5) .
C29 C34 C25 118.4(5) .
C33 C34 C25 123.4(5) .
C40 C35 C36 120.5(7) .
C40 C35 Cl1 120.8(6) .
C36 C35 Cl1 118.7(6) .
C37 C36 C35 119.2(7) .
C36 C37 C38 120.0(7) .
C37 C38 C39 121.6(7) .
C40 C39 C38 118.8(7) .
C39 C40 C35 119.8(7) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 I2 2.9281(3) .
I1 I2 2.9281(3) 2_656
I3 I4 2.9465(4) .
I3 I4 2.9466(4) 2_655
Cl1 C35 1.734(7) .
S1 C1 1.735(6) .
S1 C3 1.739(7) .
S2 C4 1.723(6) .
S2 C1 1.728(6) .
S3 C2 1.732(6) .
S3 C5 1.749(6) .
S4 C2 1.725(6) .
S4 C6 1.726(6) .
N1 C8 1.345(8) .
N1 C7 1.373(8) .
N1 C11 1.488(6) .
N2 C9 1.358(7) .
N2 C10 1.369(7) .
N2 C12 1.481(6) .
C1 C2 1.409(6) .
C3 C7 1.379(9) .
C3 C4 1.415(7) .
C4 C8 1.374(9) .
C5 C9 1.347(9) .
C5 C6 1.416(7) .
C6 C10 1.393(9) .
C11 C13 1.529(8) .
C11 C15 1.530(8) .
C12 C14 1.523(8) .
C12 C25 1.530(8) .
C15 C16 1.369(8) .
C15 C24 1.432(8) .
C16 C17 1.416(9) .
C17 C18 1.356(9) .
C18 C19 1.414(9) .
C19 C20 1.414(9) .
C19 C24 1.421(9) .
C20 C21 1.345(10) .
C21 C22 1.400(11) .
C22 C23 1.367(9) .
C23 C24 1.429(8) .
C25 C26 1.368(8) .
C25 C34 1.441(7) .
C26 C27 1.420(8) .
C27 C28 1.369(8) .
C28 C29 1.420(8) .
C29 C34 1.418(8) .
C29 C30 1.428(8) .
C30 C31 1.355(10) .
C31 C32 1.405(10) .
C32 C33 1.371(8) .
C33 C34 1.433(9) .
C35 C40 1.388(10) .
C35 C36 1.394(11) .
C36 C37 1.362(9) .
C37 C38 1.373(9) .
C38 C39 1.379(10) .
C39 C40 1.372(10) .
