#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:26:53 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180299 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/13/7151381.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_7151381
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            'C30 H29 N S6'
_chemical_formula_weight         595.90
_chemical_melting_point          494.6(5)
_chemical_name_systematic
; 
9-{pyrrolo[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           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.64(1)
_cell_angle_beta                 95.44(1)
_cell_angle_gamma                108.73(1)
_cell_formula_units_Z            2
_cell_length_a                   9.226(1)
_cell_length_b                   12.541(1)
_cell_length_c                   12.760(2)
_cell_measurement_reflns_used    994
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      12.0
_cell_volume                     1360.9(3)
_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      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16870
_diffrn_reflns_theta_full        29.06
_diffrn_reflns_theta_max         29.06
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_T_max  0.9028
_exptl_absorpt_correction_T_min  0.7839
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'XPREP (SHELXTL)'
_exptl_crystal_colour            amber
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         7114
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0305
_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)+(0.0468P)²+0.4770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0846
_reflns_number_gt                6268
_reflns_number_total             7114
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b211153p.txt
_cod_data_source_block           (33)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 '221--222\% C' was changed to
'494.6(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_cell_volume        1360.9(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151381
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.47516(4) 0.50781(3) 0.85912(3) 0.02301(8) Uani 1 1 d . . .
S2 S 0.21178(4) 0.55763(3) 0.95141(3) 0.02214(8) Uani 1 1 d . . .
S3 S 0.47304(4) 0.85141(3) 0.52063(2) 0.01853(8) Uani 1 1 d . . .
S4 S 0.22162(4) 0.91370(3) 0.60675(3) 0.01914(8) Uani 1 1 d . A .
S5 S 0.33813(4) 0.81890(3) 0.29028(3) 0.02331(8) Uani 1 1 d D . .
S6 S 0.04461(4) 0.89030(3) 0.38945(3) 0.02363(8) Uani 1 1 d . A .
N N 0.13658(18) 0.22540(11) 0.87137(11) 0.0335(3) Uani 1 1 d . . .
H1N H 0.084(3) 0.151(2) 0.8550(19) 0.054(7) Uiso 1 1 d . . .
C1 C 0.71958(16) 0.74469(12) 0.86554(11) 0.0210(3) Uani 1 1 d . . .
H1 H 0.722(2) 0.6992(15) 0.9164(14) 0.025(4) Uiso 1 1 d . . .
C2 C 0.85503(16) 0.79676(13) 0.82682(11) 0.0237(3) Uani 1 1 d . . .
H2 H 0.949(2) 0.7840(16) 0.8514(15) 0.029(5) Uiso 1 1 d . . .
C3 C 0.85402(16) 0.86637(13) 0.75298(11) 0.0234(3) Uani 1 1 d . . .
H3 H 0.947(2) 0.9049(16) 0.7249(14) 0.027(4) Uiso 1 1 d . . .
C4 C 0.71806(15) 0.88500(12) 0.71894(11) 0.0200(2) Uani 1 1 d . . .
H4 H 0.715(2) 0.9351(16) 0.6699(14) 0.027(4) Uiso 1 1 d . . .
C5 C 0.30394(15) 0.96844(11) 0.85611(11) 0.0195(2) Uani 1 1 d . . .
H5 H 0.307(2) 1.0189(15) 0.8089(14) 0.024(4) Uiso 1 1 d . . .
C6 C 0.24450(16) 0.98516(12) 0.95151(11) 0.0225(3) Uani 1 1 d . . .
H6 H 0.207(2) 1.0454(15) 0.9679(14) 0.024(4) Uiso 1 1 d . . .
C7 C 0.24545(16) 0.91378(12) 1.02350(11) 0.0224(3) Uani 1 1 d . . .
H7 H 0.211(2) 0.9258(15) 1.0878(15) 0.027(4) Uiso 1 1 d . . .
C8 C 0.30530(16) 0.82560(11) 1.00008(10) 0.0196(2) Uani 1 1 d . . .
H8 H 0.316(2) 0.7795(15) 1.0513(14) 0.021(4) Uiso 1 1 d . . .
C9 C 0.44021(15) 0.72005(11) 0.87996(10) 0.0166(2) Uani 1 1 d . . .
C10 C 0.44015(14) 0.86407(10) 0.73535(10) 0.0156(2) Uani 1 1 d . . .
C11 C 0.36426(14) 0.87990(11) 0.83104(10) 0.0159(2) Uani 1 1 d . . .
C12 C 0.36440(14) 0.80684(11) 0.90443(10) 0.0162(2) Uani 1 1 d . . .
C13 C 0.58237(15) 0.76365(11) 0.83274(10) 0.0169(2) Uani 1 1 d . . .
C14 C 0.58189(15) 0.83573(11) 0.75879(10) 0.0166(2) Uani 1 1 d . . .
C15 C 0.38435(15) 0.61089(11) 0.89623(10) 0.0181(2) Uani 1 1 d . . .
C16 C 0.31772(18) 0.39002(12) 0.86905(11) 0.0238(3) Uani 1 1 d . . .
C17 C 0.19236(17) 0.41320(12) 0.91129(11) 0.0231(3) Uani 1 1 d . . .
C18 C 0.2810(2) 0.27196(13) 0.84436(12) 0.0295(3) Uani 1 1 d . . .
H18 H 0.332(2) 0.2322(17) 0.8138(15) 0.029(5) Uiso 1 1 d . . .
C19 C 0.0798(2) 0.31001(13) 0.91144(13) 0.0297(3) Uani 1 1 d . . .
H19 H -0.012(3) 0.2956(18) 0.9280(17) 0.040(6) Uiso 1 1 d . . .
C20 C 0.38650(14) 0.87502(10) 0.63614(10) 0.0163(2) Uani 1 1 d . . .
C21 C 0.31850(15) 0.84735(11) 0.42642(10) 0.0184(2) Uani 1 1 d . A .
C22 C 0.20160(15) 0.87481(11) 0.46596(10) 0.0187(2) Uani 1 1 d . . .
C23A C 0.3140(3) 0.66683(14) 0.26955(13) 0.0245(4) Uani 0.911(4) 1 d PD A 1
H231 H 0.3210 0.6385 0.1938 0.032 Uiso 0.911(4) 1 d PR A 1
H232 H 0.3996 0.6577 0.3157 0.032 Uiso 0.911(4) 1 d PR A 1
C24A C 0.1606(2) 0.59479(14) 0.29618(13) 0.0257(4) Uani 0.911(4) 1 d PD A 1
H241 H 0.1565 0.6204 0.3731 0.033 Uiso 0.911(4) 1 d PR A 1
H242 H 0.0755 0.6080 0.2533 0.033 Uiso 0.911(4) 1 d PR A 1
C25A C 0.1355(2) 0.46592(15) 0.27312(14) 0.0302(4) Uani 0.911(4) 1 d PD A 1
H251 H 0.1272 0.4379 0.1949 0.039 Uiso 0.911(4) 1 d PR A 1
H252 H 0.2257 0.4530 0.3099 0.039 Uiso 0.911(4) 1 d PR A 1
C26A C -0.0113(3) 0.3979(2) 0.31138(17) 0.0343(5) Uani 0.911(4) 1 d PD A 1
H261 H -0.0049 0.4275 0.3882 0.052 Uiso 0.911(4) 1 d PR A 1
H262 H -0.0217 0.3165 0.2993 0.052 Uiso 0.911(4) 1 d PR A 1
H263 H -0.1015 0.4062 0.2714 0.052 Uiso 0.911(4) 1 d PR A 1
C23B C 0.388(2) 0.6860(13) 0.2811(15) 0.026(4) Uiso 0.089(4) 1 d PD A 2
H233 H 0.3923 0.6580 0.2045 0.034 Uiso 0.089(4) 1 calc PR A 2
H234 H 0.4948 0.7082 0.3208 0.034 Uiso 0.089(4) 1 calc PR A 2
C24B C 0.2864(17) 0.5854(13) 0.3214(13) 0.027(4) Uiso 0.089(4) 1 d PD A 2
H243 H 0.2753 0.6129 0.3964 0.035 Uiso 0.089(4) 1 d PR A 2
H244 H 0.3398 0.5286 0.3224 0.035 Uiso 0.089(4) 1 d PR A 2
C25B C 0.1264(17) 0.5248(17) 0.2564(14) 0.029(4) Uiso 0.089(4) 1 d PD A 2
H253 H 0.0761 0.5823 0.2484 0.038 Uiso 0.089(4) 1 d PR A 2
H254 H 0.1357 0.4882 0.1837 0.038 Uiso 0.089(4) 1 d PR A 2
C26B C 0.027(3) 0.4350(19) 0.3080(18) 0.027(5) Uiso 0.089(4) 1 d PD A 2
H26A H -0.0751 0.3979 0.2635 0.041 Uiso 0.089(4) 1 calc PR A 2
H26B H 0.0163 0.4711 0.3796 0.041 Uiso 0.089(4) 1 calc PR A 2
H26C H 0.0762 0.3771 0.3147 0.041 Uiso 0.089(4) 1 calc PR A 2
C27 C -0.12088(16) 0.80517(13) 0.44279(12) 0.0241(3) Uani 1 1 d . . .
H271 H -0.112(2) 0.8379(16) 0.5190(15) 0.027(4) Uiso 1 1 d . . .
H272 H -0.208(2) 0.8174(17) 0.4063(16) 0.033(5) Uiso 1 1 d . . .
C28 C -0.14636(17) 0.67752(13) 0.42061(12) 0.0262(3) Uani 1 1 d . A .
H281 H -0.059(2) 0.6651(16) 0.4554(15) 0.030(5) Uiso 1 1 d . . .
H282 H -0.150(2) 0.6493(15) 0.3424(15) 0.025(4) Uiso 1 1 d . . .
C29 C -0.29430(19) 0.60935(15) 0.45801(15) 0.0324(3) Uani 1 1 d . . .
H291 H -0.384(2) 0.6257(18) 0.4230(16) 0.041(5) Uiso 1 1 d . . .
H292 H -0.288(3) 0.6365(19) 0.5353(18) 0.046(6) Uiso 1 1 d . . .
C30 C -0.3251(2) 0.48024(16) 0.43428(17) 0.0383(4) Uani 1 1 d . A .
H301 H -0.339(3) 0.447(2) 0.360(2) 0.057(7) Uiso 1 1 d . . .
H302 H -0.419(3) 0.4367(19) 0.4583(18) 0.047(6) Uiso 1 1 d . . .
H303 H -0.237(3) 0.461(2) 0.4669(19) 0.055(6) Uiso 1 1 d . . .
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 0.00 -1.00 0.1000
0.00 0.00 1.00 0.1000
-1.00 0.00 0.00 0.1800
1.00 0.00 0.00 0.1800
0.00 1.00 0.00 0.1800
0.00 -1.00 0.00 0.1800
-1.00 1.00 0.00 0.2300
0.00 -1.00 -1.00 0.1400
0.00 1.00 1.00 0.1400
0.00 1.00 -1.00 0.2000
0.00 -1.00 1.00 0.2000
1.00 -1.00 0.00 0.2600
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 94.86(7) . . ?
C17 S2 C15 94.83(7) . . ?
C21 S3 C20 96.38(6) . . ?
C22 S4 C20 96.63(6) . . ?
C21 S5 C23A 100.53(7) . . ?
C21 S5 C23B 101.0(6) . . ?
C23A S5 C23B 20.1(6) . . ?
C22 S6 C27 102.54(6) . . ?
C19 N C18 111.13(13) . . ?
C2 C1 C13 120.70(12) . . ?
C3 C2 C1 119.88(13) . . ?
C2 C3 C4 119.97(13) . . ?
C3 C4 C14 121.00(12) . . ?
C6 C5 C11 120.99(12) . . ?
C7 C6 C5 119.93(13) . . ?
C6 C7 C8 119.87(13) . . ?
C7 C8 C12 121.09(12) . . ?
C15 C9 C13 123.08(12) . . ?
C15 C9 C12 124.19(12) . . ?
C13 C9 C12 112.71(11) . . ?
C20 C10 C14 123.16(11) . . ?
C20 C10 C11 123.89(11) . . ?
C14 C10 C11 112.94(10) . . ?
C5 C11 C12 118.95(12) . . ?
C5 C11 C10 123.20(11) . . ?
C12 C11 C10 117.67(11) . . ?
C8 C12 C11 119.17(12) . . ?
C8 C12 C9 122.93(11) . . ?
C11 C12 C9 117.68(11) . . ?
C1 C13 C14 119.40(12) . . ?
C1 C13 C9 122.59(11) . . ?
C14 C13 C9 117.77(11) . . ?
C4 C14 C13 119.02(12) . . ?
C4 C14 C10 122.93(11) . . ?
C13 C14 C10 117.79(11) . . ?
C9 C15 S1 122.29(10) . . ?
C9 C15 S2 123.15(10) . . ?
S1 C15 S2 114.52(7) . . ?
C18 C16 C17 107.77(14) . . ?
C18 C16 S1 135.09(13) . . ?
C17 C16 S1 117.15(11) . . ?
C19 C17 C16 108.38(14) . . ?
C19 C17 S2 134.82(13) . . ?
C16 C17 S2 116.80(11) . . ?
N C18 C16 106.40(15) . . ?
N C19 C17 106.31(15) . . ?
C10 C20 S4 124.20(10) . . ?
C10 C20 S3 124.03(10) . . ?
S4 C20 S3 111.77(7) . . ?
C22 C21 S5 126.14(10) . . ?
C22 C21 S3 116.90(10) . . ?
S5 C21 S3 116.76(8) . . ?
C21 C22 S6 125.55(10) . . ?
C21 C22 S4 116.40(10) . . ?
S6 C22 S4 117.64(8) . . ?
C24A C23A S5 112.51(12) . . ?
C23A C24A C25A 112.83(14) . . ?
C26A C25A C24A 111.26(15) . . ?
C24B C23B S5 119.3(13) . . ?
C25B C24B C23B 115.4(14) . . ?
C26B C25B C24B 112.0(15) . . ?
C28 C27 S6 113.84(10) . . ?
C27 C28 C29 111.56(13) . . ?
C30 C29 C28 112.76(15) . . ?
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 1.7400(15) . ?
S1 C15 1.7785(13) . ?
S2 C17 1.7431(14) . ?
S2 C15 1.7787(14) . ?
S3 C21 1.7574(13) . ?
S3 C20 1.7681(13) . ?
S4 C22 1.7564(13) . ?
S4 C20 1.7654(13) . ?
S5 C21 1.7526(13) . ?
S5 C23A 1.8176(16) . ?
S5 C23B 1.857(14) . ?
S6 C22 1.7507(13) . ?
S6 C27 1.8242(15) . ?
N C19 1.374(2) . ?
N C18 1.375(2) . ?
C1 C2 1.390(2) . ?
C1 C13 1.4002(18) . ?
C2 C3 1.389(2) . ?
C3 C4 1.3912(19) . ?
C4 C14 1.3952(18) . ?
C5 C6 1.3934(19) . ?
C5 C11 1.3989(18) . ?
C6 C7 1.387(2) . ?
C7 C8 1.3892(19) . ?
C8 C12 1.3980(18) . ?
C9 C15 1.3584(18) . ?
C9 C13 1.4771(18) . ?
C9 C12 1.4792(17) . ?
C10 C20 1.3600(17) . ?
C10 C14 1.4785(17) . ?
C10 C11 1.4801(17) . ?
C11 C12 1.4157(17) . ?
C13 C14 1.4124(17) . ?
C16 C18 1.381(2) . ?
C16 C17 1.412(2) . ?
C17 C19 1.375(2) . ?
C21 C22 1.3490(19) . ?
C23A C24A 1.519(3) . ?
C24A C25A 1.530(2) . ?
C25A C26A 1.525(3) . ?
C23B C24B 1.514(16) . ?
C24B C25B 1.511(16) . ?
C25B C26B 1.497(17) . ?
C27 C28 1.514(2) . ?
C28 C29 1.527(2) . ?
C29 C30 1.523(2) . ?
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
C26A C25A C24A C23A 174.22(15) . . . . ?
C25A C24A C23A S5 176.87(11) . . . . ?
C24A C23A S5 C21 57.43(13) . . . . ?
C23A S5 C21 C22 -113.02(14) . . . . ?
S5 C21 C22 S6 -1.08(19) . . . . ?
C21 C22 S6 C27 131.87(13) . . . . ?
C22 S6 C27 C28 -65.80(12) . . . . ?
S6 C27 C28 C29 -174.89(11) . . . . ?
C27 C28 C29 C30 178.61(14) . . . . ?
