#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:26:53 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180299 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/13/7151382.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_7151382
loop_
_publ_author_name
'Christensen, Christian A.'
'Bryce, Martin R.'
'Batsanov, Andrei S.'
'Becher, Jan'
_publ_section_title
;
 New strategies and building blocks for functionalised
 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene derivatives,
 including pyrrolo-annelated derivatives and π-extended systems with
 intramolecular charge-transferThis paper is Molecular Saddles Part 10.
 For Part 9 see reference 5c.Electronic supplementary information (ESI)
 available: NOE spectra for compound 23. See
 http://www.rsc.org/suppdata/ob/b2/b211153p/
;
_journal_issue                   3
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              511
_journal_paper_doi               10.1039/b211153p
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C31 H31 N S6'
_chemical_formula_weight         609.93
_chemical_melting_point          487.6(5)
_chemical_name_systematic
; 
9-{N-methylpyrrolo[3,4-d]-1,3-dithiol-2-ylidene}-10-{4,5-
bis(butylsulfanyl)-1,3-dithiol-2-ylidene}-9,10-dihydroanthracene
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.73(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.276(3)
_cell_length_b                   9.688(2)
_cell_length_c                   25.605(5)
_cell_measurement_reflns_used    415
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.5
_cell_measurement_theta_min      12.0
_cell_volume                     2992.0(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'SMART 1K CCD area detector'
_diffrn_measurement_method       'ω 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  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            35752
_diffrn_reflns_theta_full        29.19
_diffrn_reflns_theta_max         29.19
_diffrn_reflns_theta_min         1.62
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.480
_exptl_absorpt_correction_T_max  0.9149
_exptl_absorpt_correction_T_min  0.8476
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'XPREP (SHELXTL, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         7991
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0488
_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)+(0.0516P)²+1.5583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1331
_reflns_number_gt                5753
_reflns_number_total             7991
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b211153p.txt
_cod_data_source_block           (34)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '214--215\% C' was changed to
'487.6(5)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7151382
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.56009(6) 0.95497(6) 0.67125(3) 0.06389(18) Uani 1 1 d . . .
S2 S 0.56554(5) 0.67583(7) 0.72058(3) 0.06125(17) Uani 1 1 d . . .
S3 S 0.13789(5) 0.75594(7) 0.48078(2) 0.06031(17) Uani 1 1 d . . .
S4 S 0.15084(5) 0.47973(6) 0.52732(2) 0.05435(15) Uani 1 1 d . A .
S5 S 0.11825(6) 0.65830(11) 0.36882(3) 0.0866(3) Uani 1 1 d . . .
S6 S 0.12222(6) 0.33670(10) 0.42154(3) 0.0823(2) Uani 1 1 d . A .
N N 0.86266(18) 0.8015(3) 0.70503(9) 0.0713(6) Uani 1 1 d . . .
C1 C 0.3164(2) 1.0475(2) 0.64843(10) 0.0578(6) Uani 1 1 d . . .
H1 H 0.3757 1.0776 0.6739 0.069 Uiso 1 1 d R . .
C2 C 0.2432(3) 1.1434(2) 0.62101(12) 0.0693(7) Uani 1 1 d . . .
H2 H 0.2547 1.2369 0.6279 0.083 Uiso 1 1 d R . .
C3 C 0.1539(2) 1.1010(3) 0.58397(13) 0.0723(8) Uani 1 1 d . . .
H3 H 0.1051 1.1659 0.5661 0.087 Uiso 1 1 d R . .
C4 C 0.1372(2) 0.9625(3) 0.57293(11) 0.0602(6) Uani 1 1 d . . .
H4 H 0.0760 0.9344 0.5482 0.072 Uiso 1 1 d R . .
C5 C 0.15510(18) 0.5174(2) 0.64719(9) 0.0495(5) Uani 1 1 d . . .
H5 H 0.0963 0.4906 0.6208 0.059 Uiso 1 1 d R . .
C6 C 0.1779(2) 0.4446(2) 0.69456(10) 0.0570(6) Uani 1 1 d . . .
H6 H 0.1352 0.3686 0.6997 0.068 Uiso 1 1 d R . .
C7 C 0.2641(2) 0.4851(2) 0.73379(10) 0.0577(6) Uani 1 1 d . . .
H7 H 0.2797 0.4357 0.7653 0.069 Uiso 1 1 d R . .
C8 C 0.3275(2) 0.6005(2) 0.72667(8) 0.0515(5) Uani 1 1 d . . .
H8 H 0.3842 0.6284 0.7539 0.062 Uiso 1 1 d R . .
C9 C 0.37139(18) 0.7981(2) 0.66911(8) 0.0437(4) Uani 1 1 d . . .
C10 C 0.19513(15) 0.7141(2) 0.58918(8) 0.0426(4) Uani 1 1 d . . .
C11 C 0.21960(16) 0.6311(2) 0.63854(8) 0.0410(4) Uani 1 1 d . . .
C12 C 0.30723(17) 0.67372(19) 0.67882(8) 0.0426(4) Uani 1 1 d . . .
C13 C 0.30141(18) 0.9063(2) 0.63811(8) 0.0456(4) Uani 1 1 d . . .
C14 C 0.21130(17) 0.8634(2) 0.59897(8) 0.0457(4) Uani 1 1 d . . .
C15 C 0.48247(19) 0.8090(2) 0.68530(8) 0.0480(5) Uani 1 1 d . . .
C16 C 0.6897(2) 0.8752(3) 0.68815(10) 0.0599(6) Uani 1 1 d . . .
C17 C 0.6917(2) 0.7428(3) 0.71031(9) 0.0577(6) Uani 1 1 d . . .
C18 C 0.7968(2) 0.9102(3) 0.68518(12) 0.0719(7) Uani 1 1 d . . .
H18 H 0.8197 0.9925 0.6723 0.086 Uiso 1 1 d R . .
C19 C 0.7992(2) 0.6985(3) 0.72037(10) 0.0677(7) Uani 1 1 d . . .
H19 H 0.8246 0.6141 0.7350 0.081 Uiso 1 1 d R . .
C20 C 0.16473(16) 0.6587(2) 0.54025(8) 0.0448(4) Uani 1 1 d . . .
C21 C 0.13627(18) 0.6170(3) 0.43710(9) 0.0609(6) Uani 1 1 d . A .
C22 C 0.14140(17) 0.4903(3) 0.45796(9) 0.0579(6) Uani 1 1 d . . .
C23A C 0.2538(4) 0.7236(6) 0.36487(17) 0.0770(12) Uani 0.67 1 d P A 1
H231 H 0.2532 0.7561 0.3291 0.100 Uiso 0.67 1 d PR A 1
H232 H 0.2704 0.8017 0.3886 0.100 Uiso 0.67 1 d PR A 1
C24A C 0.3442(3) 0.6176(5) 0.37959(19) 0.0715(11) Uani 0.67 1 d P A 1
H241 H 0.3252 0.5372 0.3573 0.093 Uiso 0.67 1 d PR A 1
H242 H 0.3477 0.5893 0.4161 0.093 Uiso 0.67 1 d PR A 1
C23B C 0.2533(9) 0.6240(13) 0.3536(4) 0.086(3) Uiso 0.33 1 d P A 2
H233 H 0.2724 0.5283 0.3616 0.111 Uiso 0.33 1 d PR A 2
H234 H 0.2498 0.6378 0.3159 0.111 Uiso 0.33 1 d PR A 2
C24B C 0.3458(8) 0.7174(11) 0.3848(4) 0.076(2) Uiso 0.33 1 d P A 2
H243 H 0.3462 0.7102 0.4225 0.098 Uiso 0.33 1 d PR A 2
H244 H 0.3320 0.8127 0.3742 0.098 Uiso 0.33 1 d PR A 2
C25 C 0.4590(3) 0.6683(4) 0.37325(18) 0.1060(12) Uani 1 1 d . . .
H251 H 0.4425 0.6414 0.3366 0.138 Uiso 0.67 1 d PR A 1
H252 H 0.5004 0.7523 0.3741 0.138 Uiso 0.67 1 d PR A 1
H253 H 0.4738 0.7564 0.3902 0.138 Uiso 0.33 1 d PR A 2
H254 H 0.4617 0.6784 0.3364 0.138 Uiso 0.33 1 d PR A 2
C26 C 0.5406(3) 0.5686(5) 0.3976(2) 0.1245(15) Uani 1 1 d . A .
H261 H 0.5489 0.5742 0.4354 0.187 Uiso 1 1 d R . .
H262 H 0.6102 0.5873 0.3876 0.187 Uiso 1 1 d R . .
H263 H 0.5161 0.4779 0.3860 0.187 Uiso 1 1 d R . .
C27 C 0.2307(3) 0.2252(3) 0.45595(12) 0.0763(8) Uani 1 1 d . . .
H271 H 0.2258 0.2213 0.4931 0.099 Uiso 1 1 d R A .
H272 H 0.2184 0.1328 0.4416 0.099 Uiso 1 1 d R . .
C28 C 0.3462(2) 0.2705(3) 0.45122(12) 0.0767(8) Uani 1 1 d . A .
H281 H 0.3614 0.3590 0.4686 0.100 Uiso 1 1 d R . .
H282 H 0.3495 0.2825 0.4141 0.100 Uiso 1 1 d R . .
C29 C 0.4348(3) 0.1694(4) 0.47581(16) 0.1012(11) Uani 1 1 d . . .
H291 H 0.4316 0.1573 0.5130 0.132 Uiso 1 1 d R A .
H292 H 0.4198 0.0808 0.4585 0.132 Uiso 1 1 d R . .
C30 C 0.5489(3) 0.2154(6) 0.47151(19) 0.1325(17) Uani 1 1 d . A .
H301 H 0.5528 0.2270 0.4348 0.199 Uiso 1 1 d R . .
H302 H 0.6016 0.1471 0.4870 0.199 Uiso 1 1 d R . .
H303 H 0.5654 0.3014 0.4898 0.199 Uiso 1 1 d R . .
C31 C 0.9827(3) 0.7964(4) 0.70980(14) 0.0938(11) Uani 1 1 d . . .
H311 H 1.0175 0.8344 0.7434 0.136(9) Uiso 1 1 d R . .
H312 H 1.0039 0.8490 0.6817 0.136(9) Uiso 1 1 d R . .
H313 H 1.0056 0.7024 0.7075 0.136(9) Uiso 1 1 d R . .
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -2.00 -1.00 0.1000
0.00 1.00 0.00 0.1000
-1.00 0.00 1.00 0.1400
1.00 0.00 -1.00 0.1400
0.00 0.00 -1.00 0.1800
0.00 0.00 1.00 0.1800
1.00 0.00 -4.00 0.1400
-1.00 0.00 -1.00 0.2400
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
C16 S1 C15 95.49(12) . . ?
C17 S2 C15 95.42(12) . . ?
C21 S3 C20 96.81(12) . . ?
C22 S4 C20 96.77(12) . . ?
C21 S5 C23A 100.86(16) . . ?
C21 S5 C23B 102.8(4) . . ?
C23A S5 C23B 32.5(4) . . ?
C22 S6 C27 103.56(13) . . ?
C19 N C18 109.9(2) . . ?
C19 N C31 125.0(3) . . ?
C18 N C31 125.2(3) . . ?
C2 C1 C13 120.5(3) . . ?
C3 C2 C1 120.6(2) . . ?
C2 C3 C4 120.1(2) . . ?
C3 C4 C14 120.7(3) . . ?
C6 C5 C11 120.8(2) . . ?
C7 C6 C5 119.8(2) . . ?
C6 C7 C8 120.4(2) . . ?
C7 C8 C12 120.6(2) . . ?
C15 C9 C12 123.19(18) . . ?
C15 C9 C13 123.87(19) . . ?
C12 C9 C13 112.91(18) . . ?
C20 C10 C14 123.54(19) . . ?
C20 C10 C11 123.59(19) . . ?
C14 C10 C11 112.83(18) . . ?
C5 C11 C12 119.57(18) . . ?
C5 C11 C10 122.15(19) . . ?
C12 C11 C10 118.19(18) . . ?
C8 C12 C11 118.73(19) . . ?
C8 C12 C9 123.0(2) . . ?
C11 C12 C9 118.19(17) . . ?
C1 C13 C14 118.7(2) . . ?
C1 C13 C9 123.1(2) . . ?
C14 C13 C9 118.06(18) . . ?
C4 C14 C13 119.3(2) . . ?
C4 C14 C10 122.4(2) . . ?
C13 C14 C10 118.21(17) . . ?
C9 C15 S1 123.17(16) . . ?
C9 C15 S2 123.18(16) . . ?
S1 C15 S2 113.61(13) . . ?
C18 C16 C17 107.7(2) . . ?
C18 C16 S1 135.5(2) . . ?
C17 C16 S1 116.8(2) . . ?
C19 C17 C16 107.9(2) . . ?
C19 C17 S2 135.1(2) . . ?
C16 C17 S2 116.90(19) . . ?
N C18 C16 107.2(3) . . ?
C17 C19 N 107.4(3) . . ?
C10 C20 S4 124.35(16) . . ?
C10 C20 S3 124.20(17) . . ?
S4 C20 S3 111.42(12) . . ?
C22 C21 S3 117.25(18) . . ?
C22 C21 S5 126.3(2) . . ?
S3 C21 S5 116.30(17) . . ?
C21 C22 S6 125.27(19) . . ?
C21 C22 S4 116.5(2) . . ?
S6 C22 S4 117.72(16) . . ?
C24A C23A S5 113.0(3) . . ?
C23A C24A C25 113.8(4) . . ?
C24B C23B S5 113.3(8) . . ?
C25 C24B C23B 108.7(8) . . ?
C26 C25 C24A 108.5(4) . . ?
C26 C25 C24B 134.2(5) . . ?
C24A C25 C24B 37.0(4) . . ?
C28 C27 S6 113.8(2) . . ?
C29 C28 C27 113.1(3) . . ?
C30 C29 C28 112.8(4) . . ?
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 C16 1.749(3) . ?
S1 C15 1.779(2) . ?
S2 C17 1.744(3) . ?
S2 C15 1.783(2) . ?
S3 C21 1.748(3) . ?
S3 C20 1.769(2) . ?
S4 C22 1.761(2) . ?
S4 C20 1.767(2) . ?
S5 C21 1.767(2) . ?
S5 C23A 1.801(5) . ?
S5 C23B 1.803(11) . ?
S6 C22 1.749(3) . ?
S6 C27 1.811(3) . ?
N C19 1.367(4) . ?
N C18 1.367(4) . ?
N C31 1.457(4) . ?
C1 C2 1.389(3) . ?
C1 C13 1.399(3) . ?
C2 C3 1.372(4) . ?
C3 C4 1.379(4) . ?
C4 C14 1.403(3) . ?
C5 C6 1.386(3) . ?
C5 C11 1.398(3) . ?
C6 C7 1.373(4) . ?
C7 C8 1.393(3) . ?
C8 C12 1.398(3) . ?
C9 C15 1.354(3) . ?
C9 C12 1.486(3) . ?
C9 C13 1.487(3) . ?
C10 C20 1.350(3) . ?
C10 C14 1.475(3) . ?
C10 C11 1.481(3) . ?
C11 C12 1.407(3) . ?
C13 C14 1.410(3) . ?
C16 C18 1.373(4) . ?
C16 C17 1.401(4) . ?
C17 C19 1.366(4) . ?
C21 C22 1.335(4) . ?
C23A C24A 1.507(7) . ?
C24A C25 1.529(5) . ?
C23B C24B 1.552(14) . ?
C24B C25 1.548(10) . ?
C25 C26 1.446(6) . ?
C27 C28 1.511(4) . ?
C28 C29 1.510(5) . ?
C29 C30 1.494(6) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C26 C25 C24A C23A 169.5(4) . . . . ?
C25 C24A C23A S5 176.5(3) . . . . ?
C24A C23A S5 C21 61.9(4) . . . . ?
C23A S5 C21 C22 -109.1(3) . . . . ?
S5 C21 C22 S6 -4.4(3) . . . . ?
C21 C22 S6 C27 137.3(2) . . . . ?
C22 S6 C27 C28 -67.9(2) . . . . ?
S6 C27 C28 C29 -174.7(2) . . . . ?
C27 C28 C29 C30 -179.4(3) . . . . ?
C26 C25 C24B C23B -89.3(9) . . . . ?
C25 C24B C23B S5 173.9(6) . . . . ?
C24B C23B S5 C21 -62.8(8) . . . . ?
C23B S5 C21 C22 -76.0(4) . . . . ?
