# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'John Wallis'
'Andrew C. Brooks'
'Peter Day'
'Peter Horton'
'Hongchao Li.'
'Louise Male'
'Lee Martin'
'Songjie Yang.'

_publ_contact_author_name        'John Wallis'
_publ_contact_author_email       JOHN.WALLIS@NTU.AC.UK

_publ_section_title              
;
Novel Enantiopure Bis(pyrrolo)tetrathiafulvalene
Donors Exhibiting Chiral Crystal Packing Arrangements.
;

data_f:\pyrrol~1\sy1\sy1
_database_code_depnum_ccdc_archive 'CCDC 705462'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Bis(S-N-(1-phenylethyl)-2,5-dihdyropyrrolo)tetrathiafulvalene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H26 N2 S4'
_chemical_formula_weight         494.73

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.9951(12)
_cell_length_b                   6.5877(13)
_cell_length_c                   15.830(3)
_cell_angle_alpha                86.69(3)
_cell_angle_beta                 83.08(3)
_cell_angle_gamma                76.01(3)
_cell_volume                     602.0(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    37149
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       slab
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             260
_exptl_absorpt_coefficient_mu    0.412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12173
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         27.58
_reflns_number_total             5201
_reflns_number_gt                4924
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0750P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(6)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         5201
_refine_ls_number_parameters     291
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1250
_refine_ls_wR_factor_gt          0.1230
_refine_ls_goodness_of_fit_ref   1.302
_refine_ls_restrained_S_all      1.301
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.89316(9) 0.59672(9) 0.39258(4) 0.01889(16) Uani 1 1 d . . .
S2 S -0.78288(9) 0.14100(8) 0.35057(4) 0.01862(17) Uani 1 1 d . . .
S21 S -0.47744(9) 0.51278(9) 0.50699(4) 0.01955(17) Uani 1 1 d . . .
S22 S -0.35333(9) 0.05435(8) 0.46860(4) 0.01787(17) Uani 1 1 d . . .
N1 N -1.2556(4) 0.4917(4) 0.20964(15) 0.0193(5) Uani 1 1 d . . .
N21 N 0.0030(4) 0.1893(4) 0.64947(15) 0.0209(5) Uani 1 1 d . . .
C1 C -0.7146(5) 0.3421(4) 0.40515(18) 0.0171(5) Uani 1 1 d . . .
C2 C -1.0547(5) 0.5162(5) 0.32236(18) 0.0193(5) Uani 1 1 d . . .
C3 C -1.0057(5) 0.3129(4) 0.30353(17) 0.0179(5) Uani 1 1 d . . .
C4 C -1.2499(5) 0.6400(5) 0.27624(19) 0.0214(6) Uani 1 1 d . . .
H4B H -1.3970 0.6723 0.3142 0.026 Uiso 1 1 calc R . .
H4A H -1.2165 0.7719 0.2509 0.026 Uiso 1 1 calc R . .
C5 C -1.1637(5) 0.2751(5) 0.24274(18) 0.0183(6) Uani 1 1 d . . .
H5A H -1.0780 0.1822 0.1967 0.022 Uiso 1 1 calc R . .
H5B H -1.2888 0.2144 0.2723 0.022 Uiso 1 1 calc R . .
C6 C -1.4815(5) 0.5200(5) 0.17654(18) 0.0233(6) Uani 1 1 d . . .
H6 H -1.5931 0.4755 0.2217 0.028 Uiso 1 1 calc R . .
C7 C -1.5760(6) 0.7503(5) 0.1514(2) 0.0373(8) Uani 1 1 d . . .
H7A H -1.5922 0.8370 0.2010 0.056 Uiso 1 1 calc R . .
H7B H -1.7274 0.7673 0.1308 0.056 Uiso 1 1 calc R . .
H7C H -1.4688 0.7938 0.1062 0.056 Uiso 1 1 calc R . .
C8 C -1.4549(4) 0.3872(4) 0.09933(16) 0.0196(5) Uani 1 1 d . . .
C9 C -1.6310(5) 0.2942(5) 0.08442(17) 0.0248(6) Uani 1 1 d . . .
H9 H -1.7661 0.3112 0.1240 0.030 Uiso 1 1 calc R . .
C10 C -1.6130(5) 0.1770(5) 0.01280(19) 0.0292(6) Uani 1 1 d . . .
H10 H -1.7351 0.1148 0.0036 0.035 Uiso 1 1 calc R . .
C11 C -1.4168(5) 0.1505(4) -0.04540(18) 0.0279(6) Uani 1 1 d . . .
H11 H -1.4028 0.0693 -0.0943 0.034 Uiso 1 1 calc R . .
C12 C -1.2403(5) 0.2445(5) -0.03131(17) 0.0282(6) Uani 1 1 d . . .
H12 H -1.1056 0.2277 -0.0711 0.034 Uiso 1 1 calc R . .
C13 C -1.2593(4) 0.3623(5) 0.04008(17) 0.0251(6) Uani 1 1 d . . .
H13 H -1.1382 0.4264 0.0487 0.030 Uiso 1 1 calc R . .
C21 C -0.5370(5) 0.3059(4) 0.45419(18) 0.0173(5) Uani 1 1 d . . .
C22 C -0.2544(5) 0.3476(4) 0.55553(18) 0.0188(5) Uani 1 1 d . . .
C23 C -0.1982(5) 0.1429(4) 0.53949(17) 0.0183(5) Uani 1 1 d . . .
C24 C -0.0992(5) 0.3987(5) 0.6143(2) 0.0213(6) Uani 1 1 d . . .
H24A H 0.0206 0.4633 0.5830 0.026 Uiso 1 1 calc R . .
H24B H -0.1879 0.4931 0.6594 0.026 Uiso 1 1 calc R . .
C25 C -0.0002(5) 0.0306(5) 0.58724(17) 0.0185(6) Uani 1 1 d . . .
H10B H -0.0300 -0.0992 0.6161 0.022 Uiso 1 1 calc R . .
H25A H 0.1466 -0.0039 0.5492 0.022 Uiso 1 1 calc R . .
C26 C 0.2283(5) 0.1614(5) 0.68209(18) 0.0224(6) Uani 1 1 d . . .
H26 H 0.3532 0.1382 0.6333 0.027 Uiso 1 1 calc R . .
C27 C 0.2386(6) 0.3553(5) 0.7296(2) 0.0296(6) Uani 1 1 d . . .
H27A H 0.2248 0.4762 0.6898 0.044 Uiso 1 1 calc R . .
H27B H 0.3864 0.3298 0.7536 0.044 Uiso 1 1 calc R . .
H27C H 0.1113 0.3835 0.7755 0.044 Uiso 1 1 calc R . .
C28 C 0.2715(4) -0.0247(4) 0.74373(17) 0.0198(5) Uani 1 1 d . . .
C29 C 0.4968(5) -0.1397(5) 0.75243(18) 0.0262(6) Uani 1 1 d . . .
H29 H 0.6209 -0.1150 0.7131 0.031 Uiso 1 1 calc R . .
C30 C 0.5422(5) -0.2888(5) 0.81724(19) 0.0290(6) Uani 1 1 d . . .
H30 H 0.6963 -0.3660 0.8220 0.035 Uiso 1 1 calc R . .
C31 C 0.3618(5) -0.3257(5) 0.87566(19) 0.0291(6) Uani 1 1 d . . .
H31 H 0.3929 -0.4239 0.9216 0.035 Uiso 1 1 calc R . .
C32 C 0.1361(5) -0.2177(5) 0.86614(18) 0.0266(6) Uani 1 1 d . . .
H32 H 0.0118 -0.2456 0.9046 0.032 Uiso 1 1 calc R . .
C33 C 0.0917(4) -0.0690(4) 0.80053(17) 0.0222(5) Uani 1 1 d . . .
H33 H -0.0633 0.0034 0.7943 0.027 Uiso 1 1 calc R . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.741(3) . ?
S1 C1 1.773(3) . ?
S2 C3 1.741(3) . ?
S2 C1 1.775(3) . ?
S21 C22 1.735(3) . ?
S21 C21 1.767(3) . ?
S22 C23 1.748(3) . ?
S22 C21 1.773(3) . ?
N1 C6 1.477(4) . ?
N1 C4 1.487(4) . ?
N1 C5 1.489(4) . ?
N21 C26 1.471(3) . ?
N21 C24 1.474(4) . ?
N21 C25 1.482(4) . ?
C1 C21 1.360(3) . ?
C2 C3 1.343(4) . ?
C2 C4 1.498(4) . ?
C3 C5 1.499(4) . ?
C6 C8 1.514(4) . ?
C6 C7 1.533(4) . ?
C8 C9 1.391(4) . ?
C8 C13 1.394(4) . ?
C9 C10 1.387(4) . ?
C10 C11 1.386(4) . ?
C11 C12 1.394(4) . ?
C12 C13 1.385(4) . ?
C22 C23 1.340(4) . ?
C22 C24 1.496(4) . ?
C23 C25 1.501(4) . ?
C26 C28 1.514(4) . ?
C26 C27 1.536(4) . ?
C28 C33 1.394(4) . ?
C28 C29 1.398(4) . ?
C29 C30 1.383(4) . ?
C30 C31 1.394(4) . ?
C31 C32 1.390(4) . ?
C32 C33 1.390(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
_geom_angle_publ_flag
C2 S1 C1 93.31(14) . . ?
C3 S2 C1 93.38(14) . . ?
C22 S21 C21 92.97(14) . . ?
C23 S22 C21 93.16(14) . . ?
C6 N1 C4 115.0(2) . . ?
C6 N1 C5 113.2(2) . . ?
C4 N1 C5 108.1(2) . . ?
C26 N21 C24 116.7(2) . . ?
C26 N21 C25 113.4(2) . . ?
C24 N21 C25 108.8(2) . . ?
C21 C1 S1 121.22(18) . . ?
C21 C1 S2 122.73(18) . . ?
S1 C1 S2 116.05(16) . . ?
C3 C2 C4 111.1(3) . . ?
C3 C2 S1 118.7(2) . . ?
C4 C2 S1 130.2(2) . . ?
C2 C3 C5 110.6(2) . . ?
C2 C3 S2 118.5(2) . . ?
C5 C3 S2 130.9(2) . . ?
N1 C4 C2 101.0(2) . . ?
N1 C5 C3 101.1(2) . . ?
N1 C6 C8 109.8(2) . . ?
N1 C6 C7 110.3(3) . . ?
C8 C6 C7 109.2(2) . . ?
C9 C8 C13 118.6(2) . . ?
C9 C8 C6 120.3(2) . . ?
C13 C8 C6 121.1(2) . . ?
C10 C9 C8 121.2(3) . . ?
C11 C10 C9 120.0(3) . . ?
C10 C11 C12 119.2(3) . . ?
C13 C12 C11 120.7(3) . . ?
C12 C13 C8 120.4(3) . . ?
C1 C21 S21 120.63(18) . . ?
C1 C21 S22 122.90(18) . . ?
S21 C21 S22 116.47(16) . . ?
C23 C22 C24 111.0(3) . . ?
C23 C22 S21 119.5(2) . . ?
C24 C22 S21 129.4(2) . . ?
C22 C23 C25 110.5(2) . . ?
C22 C23 S22 117.8(2) . . ?
C25 C23 S22 131.7(2) . . ?
N21 C24 C22 101.3(2) . . ?
N21 C25 C23 101.3(2) . . ?
N21 C26 C28 110.9(2) . . ?
N21 C26 C27 110.9(2) . . ?
C28 C26 C27 107.7(2) . . ?
C33 C28 C29 118.2(2) . . ?
C33 C28 C26 120.7(2) . . ?
C29 C28 C26 120.5(2) . . ?
C30 C29 C28 121.2(3) . . ?
C29 C30 C31 120.0(3) . . ?
C32 C31 C30 119.5(3) . . ?
C31 C32 C33 120.2(3) . . ?
C32 C33 C28 120.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         1.122
_refine_diff_density_min         -1.157
_refine_diff_density_rms         0.378

#===END
data_f:\pyrrol~1\tetrag\tetragl
_database_code_depnum_ccdc_archive 'CCDC 705463'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Bis(S-N-(1-phenylethyl)pyrrolo)tetrathiafulvalene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 N2 S4'
_chemical_formula_weight         490.70

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'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   P43212

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/2, x+1/2, z+3/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+1/4'
'x+1/2, -y+1/2, -z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   7.4847(4)
_cell_length_b                   7.4847(4)
_cell_length_c                   42.565(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2384.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    16426
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker-Nonius Roper CCD camera on κ-goniostat
;
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12539
_diffrn_reflns_av_R_equivalents  0.0966
_diffrn_reflns_av_sigmaI/netI    0.1141
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.57
_reflns_number_total             2670
_reflns_number_gt                1765
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+6.5855P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2670
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1479
_refine_ls_R_factor_gt           0.0893
_refine_ls_wR_factor_ref         0.1486
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.8538(2) 0.1437(2) 0.01231(3) 0.0272(3) Uani 1 1 d . . .
S1 S 1.1440(2) 0.4232(2) 0.01324(3) 0.0288(3) Uani 1 1 d . . .
C1 C 1.0811(7) 0.1985(7) 0.00556(11) 0.0250(12) Uani 1 1 d . . .
N1 N 0.7087(6) 0.5806(6) 0.05758(9) 0.0260(10) Uani 1 1 d . . .
C4 C 0.8808(8) 0.6198(8) 0.04843(12) 0.0270(13) Uani 1 1 d . . .
H4 H 0.9447 0.7266 0.0528 0.032 Uiso 1 1 calc R . .
C3 C 0.8046(7) 0.3470(8) 0.03101(11) 0.0219(12) Uani 1 1 d . . .
C5 C 0.6607(8) 0.4162(7) 0.04655(12) 0.0266(13) Uani 1 1 d . . .
H5 H 0.5478 0.3601 0.0492 0.032 Uiso 1 1 calc R . .
C2 C 0.9418(8) 0.4765(7) 0.03196(13) 0.0248(13) Uani 1 1 d . . .
C6 C 0.5949(8) 0.7071(8) 0.07579(11) 0.0287(13) Uani 1 1 d . . .
H6 H 0.6761 0.7882 0.0878 0.034 Uiso 1 1 calc R . .
C8 C 0.4863(9) 0.6003(8) 0.09945(13) 0.0320(15) Uani 1 1 d . . .
C9 C 0.3102(9) 0.5534(8) 0.09400(15) 0.0417(18) Uani 1 1 d . . .
H9 H 0.2515 0.5918 0.0754 0.050 Uiso 1 1 calc R . .
C13 C 0.5678(11) 0.5460(9) 0.12705(15) 0.0497(19) Uani 1 1 d . . .
H13 H 0.6883 0.5788 0.1310 0.060 Uiso 1 1 calc R . .
C11 C 0.3029(17) 0.3948(10) 0.1431(2) 0.084(4) Uani 1 1 d . . .
H11 H 0.2403 0.3226 0.1577 0.101 Uiso 1 1 calc R . .
C12 C 0.4763(15) 0.4447(12) 0.14887(17) 0.074(3) Uani 1 1 d . . .
H12 H 0.5331 0.4096 0.1679 0.089 Uiso 1 1 calc R . .
C10 C 0.2203(11) 0.4502(10) 0.1158(2) 0.070(3) Uani 1 1 d . . .
H10 H 0.0998 0.4169 0.1120 0.084 Uiso 1 1 calc R . .
C7 C 0.4867(9) 0.8206(9) 0.05367(13) 0.0467(18) Uani 1 1 d . . .
H7A H 0.5672 0.8905 0.0403 0.070 Uiso 1 1 calc R . .
H7B H 0.4104 0.9015 0.0658 0.070 Uiso 1 1 calc R . .
H7C H 0.4120 0.7435 0.0405 0.070 Uiso 1 1 calc R . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 C3 1.756(5) . ?
S2 C1 1.773(6) . ?
S1 C2 1.756(6) . ?
S1 C1 1.777(6) . ?
C1 C1 1.329(10) 7_645 ?
N1 C5 1.365(7) . ?
N1 C4 1.377(7) . ?
N1 C6 1.491(6) . ?
C4 C2 1.360(8) . ?
C3 C5 1.366(7) . ?
C3 C2 1.413(7) . ?
C6 C7 1.504(7) . ?
C6 C8 1.521(8) . ?
C8 C9 1.383(9) . ?
C8 C13 1.385(9) . ?
C9 C10 1.383(9) . ?
C13 C12 1.381(10) . ?
C11 C12 1.373(13) . ?
C11 C10 1.378(12) . ?

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
_geom_angle_publ_flag
C3 S2 C1 94.3(3) . . ?
C2 S1 C1 94.0(3) . . ?
C1 C1 S2 122.61(18) 7_645 . ?
C1 C1 S1 121.06(18) 7_645 . ?
S2 C1 S1 116.3(3) . . ?
C5 N1 C4 109.9(4) . . ?
C5 N1 C6 126.9(5) . . ?
C4 N1 C6 123.1(5) . . ?
C2 C4 N1 107.0(5) . . ?
C5 C3 C2 107.4(5) . . ?
C5 C3 S2 135.5(5) . . ?
C2 C3 S2 117.1(4) . . ?
N1 C5 C3 107.5(5) . . ?
C4 C2 C3 108.2(5) . . ?
C4 C2 S1 134.6(4) . . ?
C3 C2 S1 117.2(4) . . ?
N1 C6 C7 109.9(4) . . ?
N1 C6 C8 108.4(5) . . ?
C7 C6 C8 115.0(5) . . ?
C9 C8 C13 119.2(6) . . ?
C9 C8 C6 122.1(6) . . ?
C13 C8 C6 118.7(6) . . ?
C10 C9 C8 119.5(7) . . ?
C12 C13 C8 120.9(8) . . ?
C12 C11 C10 119.6(8) . . ?
C11 C12 C13 119.8(8) . . ?
C11 C10 C9 121.0(8) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.089

#===END
data_f:\pyrrol~1\nap\nap
_database_code_depnum_ccdc_archive 'CCDC 705464'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Bis(R-N-(1-naphthyl)ethyl-2,5-dihydropyrrolo)tetrathiafulvalene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H30 N2 S4'
_chemical_formula_weight         594.84

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.705(3)
_cell_length_b                   6.1713(12)
_cell_length_c                   19.492(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.72(3)
_cell_angle_gamma                90.00
_cell_volume                     1447.5(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    54885
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 4096x4096pixels/62x62mm
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19829
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_sigmaI/netI    0.0961
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         28.06
_reflns_number_total             6504
_reflns_number_gt                4594
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+3.6159P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.11(16)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         6504
_refine_ls_number_parameters     363
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1236
_refine_ls_R_factor_gt           0.0796
_refine_ls_wR_factor_ref         0.1555
_refine_ls_wR_factor_gt          0.1344
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.88004(11) 0.0180(3) 0.06302(8) 0.0324(4) Uani 1 1 d . . .
S2 S 0.63582(11) -0.0185(3) 0.04044(8) 0.0346(4) Uani 1 1 d . . .
S21 S 0.86622(11) -0.4157(3) -0.03440(8) 0.0334(4) Uani 1 1 d . . .
S22 S 0.62185(11) -0.4433(3) -0.05628(8) 0.0343(4) Uani 1 1 d . . .
N1 N 0.7750(4) 0.4829(10) 0.1729(2) 0.0345(13) Uani 1 1 d . . .
N21 N 0.7124(4) -0.8540(10) -0.1860(3) 0.0375(14) Uani 1 1 d . . .
C1 C 0.7551(4) -0.1304(12) 0.0233(3) 0.0289(14) Uani 1 1 d . . .
C2 C 0.8190(4) 0.2068(12) 0.1051(3) 0.0310(15) Uani 1 1 d . . .
C3 C 0.7102(5) 0.1895(13) 0.0946(3) 0.0329(15) Uani 1 1 d . . .
C4 C 0.8702(5) 0.3830(13) 0.1566(3) 0.0351(15) Uani 1 1 d . . .
H4A H 0.9251 0.3245 0.2011 0.042 Uiso 1 1 calc R . .
H4B H 0.9076 0.4895 0.1343 0.042 Uiso 1 1 calc R . .
C5 C 0.6724(5) 0.3542(13) 0.1372(3) 0.0390(17) Uani 1 1 d . . .
H5A H 0.6442 0.2844 0.1736 0.047 Uiso 1 1 calc R . .
H5B H 0.6132 0.4468 0.1052 0.047 Uiso 1 1 calc R . .
C6 C 0.7943(4) 0.5176(10) 0.2498(3) 0.0320(12) Uani 1 1 d . . .
H6 H 0.7944 0.3735 0.2733 0.038 Uiso 1 1 calc R . .
C7 C 0.7008(5) 0.6560(13) 0.2611(3) 0.0426(17) Uani 1 1 d . . .
H7A H 0.6940 0.7913 0.2337 0.064 Uiso 1 1 calc R . .
H7B H 0.7182 0.6891 0.3127 0.064 Uiso 1 1 calc R . .
H7C H 0.6306 0.5760 0.2440 0.064 Uiso 1 1 calc R . .
C8 C 0.9056(5) 0.6264(11) 0.2861(3) 0.0350(16) Uani 1 1 d . . .
C9 C 0.9307(5) 0.8063(12) 0.2525(4) 0.0415(17) Uani 1 1 d . . .
H9 H 0.8790 0.8552 0.2083 0.050 Uiso 1 1 calc R . .
C10 C 1.0318(6) 0.9198(13) 0.2826(4) 0.0499(18) Uani 1 1 d . . .
H10 H 1.0477 1.0428 0.2583 0.060 Uiso 1 1 calc R . .
C11 C 1.1054(5) 0.8535(13) 0.3456(4) 0.048(2) Uani 1 1 d . . .
H11 H 1.1729 0.9314 0.3651 0.057 Uiso 1 1 calc R . .
C12 C 1.0854(5) 0.6729(12) 0.3832(3) 0.0378(16) Uani 1 1 d . . .
C13 C 1.1639(5) 0.6017(14) 0.4470(4) 0.058(2) Uani 1 1 d . . .
H13 H 1.2324 0.6768 0.4660 0.070 Uiso 1 1 calc R . .
C14 C 1.1426(5) 0.4228(15) 0.4828(4) 0.062(2) Uani 1 1 d . . .
H14 H 1.1973 0.3753 0.5259 0.075 Uiso 1 1 calc R . .
C15 C 1.0425(6) 0.3096(15) 0.4571(4) 0.056(2) Uani 1 1 d . . .
H15 H 1.0281 0.1902 0.4835 0.067 Uiso 1 1 calc R . .
C16 C 0.9636(5) 0.3740(12) 0.3920(3) 0.0425(15) Uani 1 1 d . . .
H16 H 0.8965 0.2942 0.3736 0.051 Uiso 1 1 calc R . .
C17 C 0.9820(5) 0.5565(13) 0.3530(3) 0.0354(15) Uani 1 1 d . . .
C21 C 0.7488(4) -0.3062(12) -0.0168(3) 0.0309(15) Uani 1 1 d . . .
C22 C 0.7882(5) -0.6147(12) -0.0935(3) 0.0301(14) Uani 1 1 d . . .
C23 C 0.6796(5) -0.6253(11) -0.1022(3) 0.0298(14) Uani 1 1 d . . .
C24 C 0.8221(5) -0.7909(12) -0.1349(3) 0.0322(15) Uani 1 1 d . . .
H24A H 0.8723 -0.7360 -0.1607 0.039 Uiso 1 1 calc R . .
H24B H 0.8583 -0.9128 -0.1031 0.039 Uiso 1 1 calc R . .
C25 C 0.6262(5) -0.8030(13) -0.1526(3) 0.0365(16) Uani 1 1 d . . .
H25A H 0.6102 -0.9293 -0.1262 0.044 Uiso 1 1 calc R . .
H26B H 0.5565 -0.7539 -0.1892 0.044 Uiso 1 1 calc R . .
C26 C 0.7034(5) -1.0741(11) -0.2149(3) 0.0397(15) Uani 1 1 d . . .
H26 H 0.7091 -1.1765 -0.1741 0.048 Uiso 1 1 calc R . .
C27 C 0.7992(5) -1.1254(15) -0.2444(4) 0.055(2) Uani 1 1 d . . .
H27A H 0.8026 -1.0140 -0.2795 0.082 Uiso 1 1 calc R . .
H27B H 0.7867 -1.2673 -0.2683 0.082 Uiso 1 1 calc R . .
H27C H 0.8695 -1.1277 -0.2044 0.082 Uiso 1 1 calc R . .
C28 C 0.5893(5) -1.1112(12) -0.2734(3) 0.0382(16) Uani 1 1 d . . .
C29 C 0.5268(6) -1.2875(12) -0.2664(4) 0.0454(17) Uani 1 1 d . . .
H29 H 0.5556 -1.3794 -0.2256 0.055 Uiso 1 1 calc R . .
C30 C 0.4242(6) -1.3375(14) -0.3159(4) 0.0495(18) Uani 1 1 d . . .
H30 H 0.3849 -1.4623 -0.3092 0.059 Uiso 1 1 calc R . .
C31 C 0.3798(6) -1.2058(13) -0.3746(4) 0.052(2) Uani 1 1 d . . .
H31 H 0.3087 -1.2374 -0.4081 0.062 Uiso 1 1 calc R . .
C32 C 0.4399(5) -1.0218(12) -0.3855(3) 0.0372(16) Uani 1 1 d . . .
C33 C 0.3970(5) -0.8882(11) -0.4450(4) 0.0454(16) Uani 1 1 d . . .
H33 H 0.3264 -0.9211 -0.4790 0.055 Uiso 1 1 calc R . .
C34 C 0.4530(6) -0.7118(15) -0.4561(4) 0.055(2) Uani 1 1 d . . .
H34 H 0.4222 -0.6227 -0.4974 0.065 Uiso 1 1 calc R . .
C35 C 0.5563(5) -0.6625(12) -0.4061(3) 0.0476(17) Uani 1 1 d . . .
H35 H 0.5949 -0.5384 -0.4142 0.057 Uiso 1 1 calc R . .
C36 C 0.6038(5) -0.7840(11) -0.3465(3) 0.0409(15) Uani 1 1 d . . .
H36 H 0.6740 -0.7450 -0.3133 0.049 Uiso 1 1 calc R . .
C37 C 0.5459(5) -0.9749(13) -0.3339(3) 0.0351(15) Uani 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.743(7) . ?
S1 C1 1.780(6) . ?
S2 C3 1.736(7) . ?
S2 C1 1.792(6) . ?
S21 C22 1.756(7) . ?
S21 C21 1.769(6) . ?
S22 C23 1.739(6) . ?
S22 C21 1.764(6) . ?
N1 C6 1.454(7) . ?
N1 C4 1.480(7) . ?
N1 C5 1.495(8) . ?
N21 C26 1.461(8) . ?
N21 C25 1.477(7) . ?
N21 C24 1.481(7) . ?
C1 C21 1.325(6) . ?
C2 C3 1.336(7) . ?
C2 C4 1.481(9) . ?
C3 C5 1.486(9) . ?
C6 C8 1.519(8) . ?
C6 C7 1.535(8) . ?
C8 C9 1.377(9) . ?
C8 C17 1.420(8) . ?
C9 C10 1.414(9) . ?
C10 C11 1.347(9) . ?
C11 C12 1.401(10) . ?
C12 C13 1.393(9) . ?
C12 C17 1.446(9) . ?
C13 C14 1.378(11) . ?
C14 C15 1.395(11) . ?
C15 C16 1.398(9) . ?
C16 C17 1.420(9) . ?
C22 C23 1.336(8) . ?
C22 C24 1.499(9) . ?
C23 C25 1.483(10) . ?
C26 C27 1.538(8) . ?
C26 C28 1.547(8) . ?
C28 C29 1.379(10) . ?
C28 C37 1.409(9) . ?
C29 C30 1.384(9) . ?
C30 C31 1.368(10) . ?
C31 C32 1.422(9) . ?
C32 C33 1.384(9) . ?
C32 C37 1.428(8) . ?
C33 C34 1.355(11) . ?
C34 C35 1.395(10) . ?
C35 C36 1.351(9) . ?
C36 C37 1.451(9) . ?

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
_geom_angle_publ_flag
C2 S1 C1 94.6(3) . . ?
C3 S2 C1 94.0(3) . . ?
C22 S21 C21 93.4(3) . . ?
C23 S22 C21 93.2(3) . . ?
C6 N1 C4 113.8(4) . . ?
C6 N1 C5 113.1(5) . . ?
C4 N1 C5 109.2(5) . . ?
C26 N21 C25 113.0(5) . . ?
C26 N21 C24 116.4(5) . . ?
C25 N21 C24 108.6(5) . . ?
C21 C1 S1 123.7(4) . . ?
C21 C1 S2 122.0(4) . . ?
S1 C1 S2 114.2(4) . . ?
C3 C2 C4 111.8(6) . . ?
C3 C2 S1 118.0(5) . . ?
C4 C2 S1 130.1(4) . . ?
C2 C3 C5 111.3(6) . . ?
C2 C3 S2 119.2(5) . . ?
C5 C3 S2 129.4(4) . . ?
N1 C4 C2 103.9(5) . . ?
C3 C5 N1 103.5(5) . . ?
N1 C6 C8 111.7(4) . . ?
N1 C6 C7 110.3(4) . . ?
C8 C6 C7 109.5(5) . . ?
C9 C8 C17 119.1(6) . . ?
C9 C8 C6 117.2(6) . . ?
C17 C8 C6 123.6(6) . . ?
C8 C9 C10 121.4(6) . . ?
C11 C10 C9 120.0(7) . . ?
C10 C11 C12 121.9(6) . . ?
C13 C12 C11 121.3(7) . . ?
C13 C12 C17 120.2(7) . . ?
C11 C12 C17 118.4(6) . . ?
C14 C13 C12 120.2(7) . . ?
C13 C14 C15 121.6(7) . . ?
C14 C15 C16 119.2(8) . . ?
C15 C16 C17 121.3(6) . . ?
C8 C17 C16 123.5(6) . . ?
C8 C17 C12 119.2(6) . . ?
C16 C17 C12 117.4(6) . . ?
C1 C21 S22 121.6(3) . . ?
C1 C21 S21 122.1(4) . . ?
S22 C21 S21 116.3(4) . . ?
C23 C22 C24 111.0(6) . . ?
C23 C22 S21 117.4(5) . . ?
C24 C22 S21 131.4(4) . . ?
C22 C23 C25 110.8(5) . . ?
C22 C23 S22 119.4(5) . . ?
C25 C23 S22 129.8(4) . . ?
N21 C24 C22 100.5(4) . . ?
N21 C25 C23 101.7(5) . . ?
N21 C26 C27 111.2(6) . . ?
N21 C26 C28 111.2(5) . . ?
C27 C26 C28 111.2(5) . . ?
C29 C28 C37 118.0(6) . . ?
C29 C28 C26 118.5(6) . . ?
C37 C28 C26 123.4(6) . . ?
C28 C29 C30 123.4(7) . . ?
C31 C30 C29 119.5(8) . . ?
C30 C31 C32 120.2(7) . . ?
C33 C32 C31 121.0(6) . . ?
C33 C32 C37 119.9(6) . . ?
C31 C32 C37 119.1(6) . . ?
C34 C33 C32 121.8(7) . . ?
C33 C34 C35 119.2(7) . . ?
C36 C35 C34 122.7(7) . . ?
C35 C36 C37 119.0(6) . . ?
C28 C37 C32 119.7(6) . . ?
C28 C37 C36 122.9(6) . . ?
C32 C37 C36 117.4(6) . . ?

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        28.06
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.087

#===END
data_f:\pyrrol~1\soln6\soln6
_database_code_depnum_ccdc_archive 'CCDC 705465'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Bis(R-N-(1-naphthyl)ethylpyrrolo)tetrathiafulvalene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H26 N2 S4'
_chemical_formula_weight         590.3

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   C2221

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, 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'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   10.8652(2)
_cell_length_b                   10.8969(2)
_cell_length_c                   47.0032(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5565.04(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    52065
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       slab
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2464
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            46634
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -61
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6318
_reflns_number_gt                5904
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0447P)²+25.5188P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(11)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         6318
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1558
_refine_ls_wR_factor_gt          0.1539
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_restrained_S_all      1.208
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.22380(9) 1.36601(11) 0.98775(2) 0.0279(2) Uani 1 1 d . . .
S2 S 0.05426(10) 1.36052(11) 0.98724(2) 0.0286(2) Uani 1 1 d . . .
N1 N -0.0923(4) 1.0774(3) 0.94750(7) 0.0261(7) Uani 1 1 d . . .
C1 C -0.0818(4) 1.4423(4) 0.99472(8) 0.0263(9) Uani 1 1 d . . .
C2 C -0.1542(4) 1.2423(4) 0.97055(9) 0.0254(9) Uani 1 1 d . . .
C3 C -0.0238(4) 1.2396(4) 0.97035(8) 0.0249(9) Uani 1 1 d . . .
C4 C -0.1946(4) 1.1398(5) 0.95653(8) 0.0290(9) Uani 1 1 d . . .
H4 H -0.2778 1.1164 0.9536 0.035 Uiso 1 1 calc R . .
C5 C 0.0126(4) 1.1365(4) 0.95601(8) 0.0240(8) Uani 1 1 d . . .
H5 H 0.0949 1.1109 0.9526 0.029 Uiso 1 1 calc R . .
C6 C -0.0972(5) 0.9493(4) 0.93640(9) 0.0275(9) Uani 1 1 d . . .
H6 H -0.1795 0.9374 0.9273 0.033 Uiso 1 1 calc R . .
C7 C -0.0892(6) 0.8611(5) 0.96172(10) 0.0398(11) Uani 1 1 d . . .
H7A H -0.1489 0.8857 0.9763 0.060 Uiso 1 1 calc R . .
H7B H -0.0060 0.8638 0.9697 0.060 Uiso 1 1 calc R . .
H7C H -0.1075 0.7775 0.9553 0.060 Uiso 1 1 calc R . .
C8 C 0.0002(4) 0.9310(4) 0.91354(9) 0.0263(9) Uani 1 1 d . . .
C9 C 0.1018(4) 0.8602(5) 0.91829(10) 0.0344(10) Uani 1 1 d . . .
H9 H 0.1124 0.8226 0.9364 0.041 Uiso 1 1 calc R . .
C10 C 0.1920(4) 0.8414(5) 0.89682(11) 0.0375(12) Uani 1 1 d . . .
H10 H 0.2617 0.7912 0.9005 0.045 Uiso 1 1 calc R . .
C11 C 0.1778(4) 0.8953(4) 0.87131(11) 0.0341(11) Uani 1 1 d . . .
H11 H 0.2393 0.8839 0.8572 0.041 Uiso 1 1 calc R . .
C12 C 0.0745(5) 0.9681(4) 0.86482(9) 0.0305(9) Uani 1 1 d . . .
C13 C 0.0585(5) 1.0231(5) 0.83777(10) 0.0358(11) Uani 1 1 d . . .
H13 H 0.1184 1.0096 0.8234 0.043 Uiso 1 1 calc R . .
C14 C -0.0403(5) 1.0942(5) 0.83198(10) 0.0400(12) Uani 1 1 d . . .
H14 H -0.0487 1.1306 0.8137 0.048 Uiso 1 1 calc R . .
C15 C -0.1306(5) 1.1143(5) 0.85284(10) 0.0345(10) Uani 1 1 d . . .
H15 H -0.2003 1.1635 0.8486 0.041 Uiso 1 1 calc R . .
C16 C -0.1187(4) 1.0635(4) 0.87931(10) 0.0297(10) Uani 1 1 d . . .
H16 H -0.1799 1.0789 0.8933 0.036 Uiso 1 1 calc R . .
C17 C -0.0164(4) 0.9880(4) 0.88629(9) 0.0249(9) Uani 1 1 d . . .
S1' S 0.14206(10) 0.98956(10) 0.76090(2) 0.0259(2) Uani 1 1 d . . .
S2' S 0.13678(11) 1.26671(10) 0.76136(2) 0.0273(2) Uani 1 1 d . . .
N1' N 0.4225(3) 1.1315(4) 0.80300(7) 0.0248(7) Uani 1 1 d . . .
C1' C 0.0590(4) 1.1272(4) 0.75470(8) 0.0243(8) Uani 1 1 d . . .
C2' C 0.2614(4) 1.0651(4) 0.77872(8) 0.0228(8) Uani 1 1 d . . .
C3' C 0.2602(4) 1.1943(4) 0.77891(9) 0.0254(9) Uani 1 1 d . . .
C4' C 0.3643(4) 1.0292(4) 0.79347(9) 0.0260(9) Uani 1 1 d . . .
H4' H 0.3903 0.9469 0.7965 0.031 Uiso 1 1 calc R . .
C5' C 0.3604(4) 1.2349(4) 0.79394(9) 0.0250(8) Uani 1 1 d . . .
H5' H 0.3827 1.3178 0.7974 0.030 Uiso 1 1 calc R . .
C6' C 0.5481(4) 1.1362(5) 0.81543(8) 0.0258(8) Uani 1 1 d . . .
H6' H 0.5567 1.2164 0.8256 0.031 Uiso 1 1 calc R . .
C7' C 0.6412(5) 1.1348(6) 0.79126(10) 0.0417(11) Uani 1 1 d . . .
H7'A H 0.6290 1.2071 0.7792 0.063 Uiso 1 1 calc R . .
H7'B H 0.6299 1.0603 0.7799 0.063 Uiso 1 1 calc R . .
H7'C H 0.7247 1.1359 0.7991 0.063 Uiso 1 1 calc R . .
C8' C 0.5627(4) 1.0342(4) 0.83738(9) 0.0253(9) Uani 1 1 d . . .
C9' C 0.6323(5) 0.9323(5) 0.83183(11) 0.0367(11) Uani 1 1 d . . .
H9' H 0.6715 0.9254 0.8138 0.044 Uiso 1 1 calc R . .
C10' C 0.6480(5) 0.8371(5) 0.85184(12) 0.0423(12) Uani 1 1 d . . .
H10' H 0.6959 0.7670 0.8471 0.051 Uiso 1 1 calc R . .
C11' C 0.5941(5) 0.8460(5) 0.87810(12) 0.0411(12) Uani 1 1 d . . .
H11' H 0.6038 0.7817 0.8916 0.049 Uiso 1 1 calc R . .
C12' C 0.5234(5) 0.9519(5) 0.88519(10) 0.0331(11) Uani 1 1 d . . .
C13' C 0.4694(5) 0.9624(5) 0.91243(10) 0.0414(12) Uani 1 1 d . . .
H13' H 0.4844 0.9008 0.9263 0.050 Uiso 1 1 calc R . .
C14' C 0.3958(5) 1.0603(5) 0.91907(10) 0.0421(13) Uani 1 1 d . . .
H14' H 0.3594 1.0660 0.9374 0.051 Uiso 1 1 calc R . .
C15' C 0.3739(5) 1.1529(5) 0.89865(10) 0.0351(11) Uani 1 1 d . . .
H15' H 0.3223 1.2206 0.9031 0.042 Uiso 1 1 calc R . .
C16' C 0.4278(4) 1.1439(4) 0.87230(9) 0.0298(9) Uani 1 1 d . . .
H16' H 0.4129 1.2068 0.8587 0.036 Uiso 1 1 calc R . .
C17' C 0.5044(4) 1.0451(4) 0.86464(9) 0.0257(9) Uani 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.744(4) . ?
S1 C1 1.783(5) . ?
S2 C3 1.757(5) . ?
S2 C1 1.761(5) . ?
N1 C5 1.369(6) . ?
N1 C4 1.371(6) . ?
N1 C6 1.491(5) . ?
C1 C1 1.351(8) 3_587 ?
C2 C4 1.369(7) . ?
C2 C3 1.417(6) . ?
C3 C5 1.368(6) . ?
C6 C8 1.522(6) . ?
C6 C7 1.532(6) . ?
C8 C9 1.365(7) . ?
C8 C17 1.435(6) . ?
C9 C10 1.422(7) . ?
C10 C11 1.344(7) . ?
C11 C12 1.408(7) . ?
C12 C13 1.416(7) . ?
C12 C17 1.428(6) . ?
C13 C14 1.352(8) . ?
C14 C15 1.404(7) . ?
C15 C16 1.368(6) . ?
C16 C17 1.421(6) . ?
S1' C2' 1.750(4) . ?
S1' C1' 1.774(5) . ?
S2' C3' 1.761(5) . ?
S2' C1' 1.768(5) . ?
N1' C4' 1.358(6) . ?
N1' C5' 1.381(6) . ?
N1' C6' 1.485(5) . ?
C1' C1' 1.356(8) 4_556 ?
C2' C4' 1.373(6) . ?
C2' C3' 1.408(6) . ?
C3' C5' 1.371(6) . ?
C6' C7' 1.521(6) . ?
C6' C8' 1.525(6) . ?
C8' C9' 1.368(7) . ?
C8' C17' 1.434(6) . ?
C9' C10' 1.410(7) . ?
C10' C11' 1.370(8) . ?
C11' C12' 1.426(7) . ?
C12' C13' 1.413(7) . ?
C12' C17' 1.417(6) . ?
C13' C14' 1.369(8) . ?
C14' C15' 1.413(7) . ?
C15' C16' 1.373(6) . ?
C16' C17' 1.407(7) . ?

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
_geom_angle_publ_flag
C2 S1 C1 94.0(2) . . ?
C3 S2 C1 93.7(2) . . ?
C5 N1 C4 110.5(3) . . ?
C5 N1 C6 124.9(4) . . ?
C4 N1 C6 123.0(4) . . ?
C1 C1 S2 122.96(15) 3_587 . ?
C1 C1 S1 120.08(14) 3_587 . ?
S2 C1 S1 117.0(2) . . ?
C4 C2 C3 107.5(4) . . ?
C4 C2 S1 135.6(4) . . ?
C3 C2 S1 117.0(3) . . ?
C5 C3 C2 108.0(4) . . ?
C5 C3 S2 134.3(4) . . ?
C2 C3 S2 117.6(3) . . ?
C2 C4 N1 107.1(4) . . ?
C3 C5 N1 106.8(4) . . ?
N1 C6 C8 110.1(4) . . ?
N1 C6 C7 108.2(4) . . ?
C8 C6 C7 115.3(4) . . ?
C9 C8 C17 119.5(4) . . ?
C9 C8 C6 121.4(4) . . ?
C17 C8 C6 119.1(4) . . ?
C8 C9 C10 121.5(5) . . ?
C11 C10 C9 119.4(5) . . ?
C10 C11 C12 122.1(4) . . ?
C11 C12 C13 122.0(4) . . ?
C11 C12 C17 118.9(4) . . ?
C13 C12 C17 119.1(5) . . ?
C14 C13 C12 121.4(5) . . ?
C13 C14 C15 120.2(4) . . ?
C16 C15 C14 120.4(5) . . ?
C15 C16 C17 121.2(4) . . ?
C16 C17 C12 117.7(4) . . ?
C16 C17 C8 123.7(4) . . ?
C12 C17 C8 118.6(4) . . ?
C2' S1' C1' 93.3(2) . . ?
C3' S2' C1' 93.5(2) . . ?
C4' N1' C5' 109.9(3) . . ?
C4' N1' C6' 125.9(4) . . ?
C5' N1' C6' 122.8(4) . . ?
C1' C1' S2' 120.66(14) 4_556 . ?
C1' C1' S1' 122.31(13) 4_556 . ?
S2' C1' S1' 117.0(2) . . ?
C4' C2' C3' 106.9(4) . . ?
C4' C2' S1' 135.3(4) . . ?
C3' C2' S1' 117.8(4) . . ?
C5' C3' C2' 108.5(4) . . ?
C5' C3' S2' 134.6(4) . . ?
C2' C3' S2' 116.9(4) . . ?
N1' C4' C2' 108.2(4) . . ?
C3' C5' N1' 106.5(4) . . ?
N1' C6' C7' 108.5(3) . . ?
N1' C6' C8' 109.7(4) . . ?
C7' C6' C8' 115.4(4) . . ?
C9' C8' C17' 118.8(4) . . ?
C9' C8' C6' 121.4(4) . . ?
C17' C8' C6' 119.8(4) . . ?
C8' C9' C10' 122.5(5) . . ?
C11' C10' C9' 119.8(5) . . ?
C10' C11' C12' 119.9(4) . . ?
C13' C12' C17' 120.0(5) . . ?
C13' C12' C11' 120.1(5) . . ?
C17' C12' C11' 120.0(5) . . ?
C14' C13' C12' 120.8(5) . . ?
C13' C14' C15' 120.0(5) . . ?
C16' C15' C14' 119.3(5) . . ?
C15' C16' C17' 122.5(4) . . ?
C16' C17' C12' 117.4(4) . . ?
C16' C17' C8' 123.6(4) . . ?
C12' C17' C8' 119.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.111



