Spring open two-plus-two electron storage in a disulfide-strapped methyl viologen derivative.
Benniston, Andrew C.; Hagon, Jerry; He, Xiaoyan; Yang, Songjie; Harrington, Ross W.; Organic letters 14 (2012) 506–509; doi:10.1021/ol203099h

data_1503541
_publ_section_title
;
 Spring open two-plus-two electron storage in a disulfide-strapped methyl
 viologen derivative.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              506
_journal_page_last               509
_journal_paper_doi               10.1021/ol203099h
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C32 H33 F12 N5 P2 S'
_chemical_formula_sum            'C32 H33 F12 N5 P2 S'
_chemical_formula_weight         809.63
_chemical_name_systematic
;
2,7-bis(4-methylbenzyl)thieno[2,3-c:5,4-c']dipyridine-2,7-diium 
hexafluorophosphate(V) tris-acetontrile solvate
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9868(5)
_cell_length_b                   30.2095(15)
_cell_length_c                   11.8887(5)
_cell_measurement_reflns_used    1377
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.7617
_cell_measurement_theta_min      2.6454
_cell_volume                     3586.8(3)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'thick-slice \w scans'
_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  0.0842
_diffrn_reflns_av_sigmaI/netI    0.0992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8454
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  0.9472
_exptl_absorpt_correction_T_min  0.9372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1392
_refine_ls_R_factor_gt           0.0720
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0902P)^2^+0.8138P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1611
_refine_ls_wR_factor_ref         0.2031
_reflns_number_gt                1790
_reflns_number_total             3220
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol203099h_si_001.cif
_cod_data_source_block           acb119a
_cod_database_code               1503541
_computing_special_details
;

TITL acb119 in Pnma
CELL 0.71073   9.9868  30.2095  11.8887  90.000  90.000  90.000
ZERR    4.00   0.0005   0.0015   0.0005   0.000   0.000   0.000
LATT  1
SYMM 0.5-X, -Y, 0.5+Z
SYMM -X, 0.5+Y, -Z
SYMM 0.5+X, 0.5-Y, 0.5-Z
SFAC C H N F P S
UNIT 128 132 20 48 8 4
TEMP -123
 
L.S. 8
BOND $H
CONF
ACTA
 
REM yellow block
SIZE 0.24 0.20 0.20
 
OMIT -3 50
 
FMAP 2
PLAN 5
 
REM EXTI    0.000000
WGHT    0.090200    0.813800
FVAR       0.08444
S1    6    0.712459    0.750000    0.642752    10.50000    0.02864    0.03178 =
         0.04351    0.00000   -0.00109    0.00000
P1    5    0.516423    0.376470    0.066750    11.00000    0.03089    0.05137 =
         0.02861   -0.00519    0.00318   -0.00255
F1    4    0.469951    0.416256   -0.007332    11.00000    0.08175    0.08919 =
         0.06781    0.03032    0.00616    0.02125
F2    4    0.563953    0.336872    0.144038    11.00000    0.07383    0.08185 =
         0.07118    0.02779    0.02039    0.02773
F3    4    0.611416    0.408709    0.135868    11.00000    0.04145    0.09975 =
         0.07650   -0.04165    0.00527   -0.01701
F4    4    0.636898    0.366297   -0.016714    11.00000    0.04269    0.09639 =
         0.03763   -0.01210    0.01275    0.00045
F5    4    0.422303    0.344655   -0.000912    11.00000    0.04595    0.09822 =
         0.07255   -0.04422    0.00190   -0.01349
F6    4    0.398730    0.387119    0.153592    11.00000    0.03383    0.08174 =
         0.03627   -0.01546    0.00479    0.00395
N1    3    0.510128    0.637170    0.604301    11.00000    0.03220    0.02481 =
         0.02502   -0.00116    0.00617    0.00365
N2    3    0.193929    0.750000    0.395790    10.50000    0.11669    0.05363 =
         0.07048    0.00000   -0.02773    0.00000
N3    3    0.595474    0.684288    0.356505    11.00000    0.07633    0.09395 =
         0.04946    0.00314    0.00427    0.01416
C1    1    0.612003    0.664003    0.625209    11.00000    0.03018    0.02724 =
         0.02585    0.00017    0.00324    0.00649
AFIX  43
H1A   2    0.698297    0.652313    0.640962    11.00000   -1.20000
AFIX   0
C2    1    0.591046    0.709515    0.623810    11.00000    0.02740    0.03380 =
         0.02194   -0.00335    0.00117    0.00351
C3    1    0.463747    0.725965    0.602236    11.00000    0.02899    0.03000 =
         0.02173   -0.00005    0.00745   -0.00315
C4    1    0.357156    0.696636    0.583612    11.00000    0.02737    0.02977 =
         0.03436    0.00067    0.00281    0.00382
AFIX  43
H4A   2    0.268913    0.707185    0.570494    11.00000   -1.20000
AFIX   0
C5    1    0.384808    0.652361    0.585016    11.00000    0.02718    0.03095 =
         0.03379   -0.00285    0.00156   -0.00810
AFIX  43
H5A   2    0.314502    0.631791    0.572169    11.00000   -1.20000
AFIX   0
C6    1    0.531294    0.587832    0.605227    11.00000    0.04434    0.02340 =
         0.02994    0.00296    0.00154    0.00498
AFIX  23
H6A   2    0.477832    0.574511    0.666641    11.00000   -1.20000
H6B   2    0.626877    0.581363    0.619968    11.00000   -1.20000
AFIX   0
C7    1    0.490536    0.567259    0.493878    11.00000    0.03290    0.01669 =
         0.03569   -0.00015    0.00162    0.00472
C8    1    0.375442    0.543340    0.485233    11.00000    0.03852    0.02342 =
         0.05343    0.00269    0.00184    0.00388
AFIX  43
H8A   2    0.318490    0.540258    0.548756    11.00000   -1.20000
AFIX   0
C9    1    0.341161    0.523590    0.384875    11.00000    0.03722    0.02595 =
         0.07072    0.00527   -0.00844   -0.00126
AFIX  43
H9A   2    0.260568    0.506962    0.380784    11.00000   -1.20000
AFIX   0
C10   1    0.419364    0.527148    0.291005    11.00000    0.05676    0.03169 =
         0.05411   -0.01538   -0.02951    0.01477
C11   1    0.536922    0.551387    0.300475    11.00000    0.05271    0.04879 =
         0.04195   -0.01039    0.00566    0.01105
AFIX  43
H11A  2    0.594059    0.554169    0.236980    11.00000   -1.20000
AFIX   0
C12   1    0.572677    0.571671    0.401053    11.00000    0.03837    0.03771 =
         0.03417   -0.00729    0.00068   -0.00605
AFIX  43
H12A  2    0.652957    0.588431    0.405912    11.00000   -1.20000
AFIX   0
C13   1    0.385616    0.505251    0.180338    11.00000    0.09056    0.06102 =
         0.07408   -0.03305   -0.04878    0.02014
AFIX 137
H13A  2    0.464459    0.489497    0.151950    11.00000   -1.50000
H13B  2    0.358376    0.527843    0.125787    11.00000   -1.50000
H13C  2    0.312119    0.484209    0.191487    11.00000   -1.50000
AFIX   0
C14   1    0.080367    0.750000    0.379406    10.50000    0.09912    0.04053 =
         0.05450    0.00000   -0.00964    0.00000
C15   1   -0.063737    0.750000    0.358220    10.50000    0.06523    0.08548 =
         0.08281    0.00000   -0.01155    0.00000
AFIX 137
H15A  2   -0.100503    0.720684    0.375302    10.50000   -1.50000
H15B  2   -0.080445    0.757109    0.279027    10.50000   -1.50000
H15C  2   -0.106924    0.772207    0.406121    10.50000   -1.50000
AFIX   0
C16   1    0.673689    0.669251    0.296464    11.00000    0.07557    0.06114 =
         0.04319    0.01319   -0.00181    0.00404
C17   1    0.774918    0.649659    0.222538    11.00000    0.06999    0.07628 =
         0.04623    0.00284    0.00801    0.01162
AFIX 137
H17A  2    0.839781    0.633072    0.267811    11.00000   -1.50000
H17B  2    0.821296    0.673193    0.181294    11.00000   -1.50000
H17C  2    0.731416    0.629602    0.169040    11.00000   -1.50000
 
HKLF 4
 
REM  acb119a in Pnma
REM R1 =  0.0720 for   1790 Fo > 4sig(Fo)  and  0.1392 for all   3220 data
REM    244 parameters refined using      0 restraints
 
END  
     
;