data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Manuel Almeida'
_publ_contact_author_email       MALMEIDA@ITN.PT

_publ_section_title              
;
A unique co-crystallisation motif for bis(4-pyridyl)acetylene
involving S...spC interactions with a fused 1,3-dithiole ring
;
loop_
_publ_author_name
'Manuel Almeida'
'Sandra Isabel Godinho Dias'
'Sandra Rabaca'
'Isabel C. Santos'
'John Wallis'

# Attachment 'cocrystal.cif'

data_os4py4
_database_code_depnum_ccdc_archive 'CCDC 767260'
#TrackingRef 'cocrystal.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H24 N6 O2 S8'
_chemical_formula_weight         901.15

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'
O O 0.0106 0.0060 '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   C2/c

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

_cell_length_a                   31.9495(6)
_cell_length_b                   7.3661(2)
_cell_length_c                   20.7736(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.1160(10)
_cell_angle_gamma                90.00
_cell_volume                     3999.09(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4778
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      26.09

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1848
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8423
_exptl_absorpt_correction_T_max  0.9164
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-AXS APEX- CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15741
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         25.68
_reflns_number_total             3762
_reflns_number_gt                3037
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART, (Bruker, 2004)'
_computing_cell_refinement       'Bruker SMART, (Bruker, 2004)'
_computing_data_reduction        'Bruker SAINT, (Bruker, 2004)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP3(Farrugia,1997)
_computing_publication_material  'WinGX (Farrugia, 1999)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0373P)^2^+2.5911P] where P=(Fo^2^+2Fc^2^)/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_number_reflns         3762
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 0.31389(2) 0.12911(7) 0.13143(4) 0.02311(15) Uani 1 1 d . . .
S2 S 0.42209(2) 0.00928(8) 0.23142(3) 0.02603(15) Uani 1 1 d . . .
S3 S 0.310040(19) 0.09290(8) -0.01668(3) 0.02434(15) Uani 1 1 d . . .
S4 S 0.42642(2) -0.03841(7) 0.09082(4) 0.02392(15) Uani 1 1 d . . .
O1 O 0.36541(6) 0.0741(2) 0.28437(10) 0.0352(4) Uani 1 1 d . . .
C1 C 0.36661(8) 0.0706(3) 0.22781(14) 0.0253(5) Uani 1 1 d . . .
C2 C 0.34332(8) 0.0721(3) 0.08526(13) 0.0197(5) Uani 1 1 d . . .
C3 C 0.39235(8) 0.0178(3) 0.13038(13) 0.0207(5) Uani 1 1 d . . .
C4 C 0.35796(7) 0.1996(3) -0.02269(13) 0.0187(5) Uani 1 1 d . . .
C5 C 0.40659(8) 0.1388(3) 0.02093(13) 0.0200(5) Uani 1 1 d . . .
C6 C 0.33770(7) 0.3552(3) -0.07811(13) 0.0166(4) Uani 1 1 d . . .
C7 C 0.36432(8) 0.5198(3) -0.05934(13) 0.0188(5) Uani 1 1 d . . .
H7 H 0.3979 0.5315 -0.0125 0.023 Uiso 1 1 calc R . .
C8 C 0.34084(8) 0.6644(3) -0.11014(14) 0.0233(5) Uani 1 1 d . . .
H8 H 0.3591 0.7756 -0.0965 0.028 Uiso 1 1 calc R . .
C9 C 0.26960(8) 0.4986(3) -0.19543(14) 0.0250(5) Uani 1 1 d . . .
H9 H 0.2366 0.4895 -0.2435 0.030 Uiso 1 1 calc R . .
C10 C 0.28951(8) 0.3466(3) -0.14850(13) 0.0204(5) Uani 1 1 d . . .
H10 H 0.2704 0.2369 -0.1642 0.024 Uiso 1 1 calc R . .
C11 C 0.44759(7) 0.1994(3) 0.01233(13) 0.0186(5) Uani 1 1 d . . .
C12 C 0.43987(8) 0.1923(3) -0.06014(14) 0.0225(5) Uani 1 1 d . . .
H12 H 0.4078 0.1558 -0.1056 0.027 Uiso 1 1 calc R . .
C13 C 0.47964(8) 0.2393(3) -0.06543(15) 0.0274(5) Uani 1 1 d . . .
H13 H 0.4737 0.2342 -0.1157 0.033 Uiso 1 1 calc R . .
C14 C 0.53245(8) 0.2998(3) 0.06464(15) 0.0261(5) Uani 1 1 d . . .
H14 H 0.5648 0.3389 0.1088 0.031 Uiso 1 1 calc R . .
C15 C 0.49532(8) 0.2554(3) 0.07684(14) 0.0224(5) Uani 1 1 d . . .
H15 H 0.5023 0.2630 0.1278 0.027 Uiso 1 1 calc R . .
N1 N 0.29384(7) 0.6584(2) -0.17762(12) 0.0264(4) Uani 1 1 d . . .
N2 N 0.52590(7) 0.2915(2) -0.00424(12) 0.0264(5) Uani 1 1 d . . .
N3 N 0.39687(8) 0.5063(3) 0.24239(13) 0.0327(5) Uani 1 1 d . . .
C16 C 0.26766(8) 0.7179(3) 0.03004(14) 0.0260(5) Uani 1 1 d . . .
C17 C 0.31089(8) 0.6447(3) 0.10198(14) 0.0234(5) Uani 1 1 d . . .
C18 C 0.35335(9) 0.5808(3) 0.10565(15) 0.0294(5) Uani 1 1 d . . .
H18 H 0.3539 0.5827 0.0604 0.035 Uiso 1 1 calc R . .
C19 C 0.39460(9) 0.5145(3) 0.17662(17) 0.0333(6) Uani 1 1 d . . .
H19 H 0.4233 0.4719 0.1784 0.040 Uiso 1 1 calc R . .
C20 C 0.35565(9) 0.5670(3) 0.23759(15) 0.0304(5) Uani 1 1 d . . .
H20 H 0.3562 0.5623 0.2838 0.037 Uiso 1 1 calc R . .
C21 C 0.31241(9) 0.6361(3) 0.17000(14) 0.0257(5) Uani 1 1 d . . .
H21 H 0.2842 0.6770 0.1701 0.031 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0235(3) 0.0224(3) 0.0254(3) 0.0032(2) 0.0152(3) 0.0020(2)
S2 0.0247(3) 0.0270(3) 0.0198(3) 0.0035(2) 0.0090(2) 0.0025(2)
S3 0.0164(3) 0.0325(3) 0.0198(3) 0.0042(2) 0.0079(2) -0.0073(2)
S4 0.0230(3) 0.0218(3) 0.0296(3) 0.0085(2) 0.0166(3) 0.0057(2)
O1 0.0432(10) 0.0394(10) 0.0255(10) 0.0009(8) 0.0213(9) 0.0048(8)
C1 0.0299(12) 0.0191(12) 0.0248(14) 0.0011(9) 0.0145(11) -0.0002(9)
C2 0.0220(11) 0.0157(11) 0.0211(12) 0.0019(9) 0.0122(10) -0.0035(8)
C3 0.0222(11) 0.0170(11) 0.0203(12) 0.0031(9) 0.0107(10) -0.0008(8)
C4 0.0177(10) 0.0206(11) 0.0175(12) 0.0000(9) 0.0099(9) -0.0046(8)
C5 0.0202(10) 0.0169(11) 0.0201(12) 0.0015(9) 0.0099(9) -0.0014(8)
C6 0.0163(10) 0.0199(11) 0.0160(11) -0.0002(8) 0.0106(9) -0.0005(8)
C7 0.0155(10) 0.0229(11) 0.0188(12) -0.0009(9) 0.0104(9) -0.0026(8)
C8 0.0237(11) 0.0193(11) 0.0297(14) -0.0013(10) 0.0169(10) -0.0039(9)
C9 0.0167(10) 0.0334(13) 0.0195(13) 0.0048(10) 0.0073(9) 0.0009(9)
C10 0.0186(10) 0.0231(12) 0.0186(12) -0.0023(9) 0.0102(9) -0.0056(8)
C11 0.0164(10) 0.0129(10) 0.0246(13) 0.0016(8) 0.0108(9) 0.0011(8)
C12 0.0189(10) 0.0209(11) 0.0257(13) -0.0036(9) 0.0116(10) -0.0019(8)
C13 0.0315(12) 0.0282(13) 0.0301(14) -0.0022(10) 0.0221(11) -0.0002(10)
C14 0.0182(11) 0.0222(12) 0.0310(14) -0.0003(10) 0.0102(10) -0.0019(9)
C15 0.0201(10) 0.0228(11) 0.0220(13) 0.0011(9) 0.0107(10) 0.0010(9)
N1 0.0233(9) 0.0250(10) 0.0273(12) 0.0067(8) 0.0125(9) 0.0028(8)
N2 0.0222(9) 0.0240(11) 0.0363(13) -0.0002(9) 0.0186(9) -0.0007(8)
N3 0.0323(11) 0.0251(11) 0.0318(13) 0.0024(9) 0.0133(10) 0.0001(8)
C16 0.0327(12) 0.0208(12) 0.0217(12) -0.0013(9) 0.0141(10) -0.0113(9)
C17 0.0290(12) 0.0142(11) 0.0222(13) -0.0013(9) 0.0120(10) -0.0080(9)
C18 0.0397(13) 0.0229(12) 0.0301(14) -0.0034(10) 0.0226(12) -0.0070(10)
C19 0.0324(13) 0.0234(13) 0.0438(17) -0.0020(11) 0.0218(12) -0.0033(10)
C20 0.0396(14) 0.0261(13) 0.0242(13) 0.0019(10) 0.0176(11) -0.0040(10)
C21 0.0305(12) 0.0219(12) 0.0249(13) -0.0001(9) 0.0161(11) -0.0023(9)

_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 1.737(2) . ?
S1 C1 1.775(2) . ?
S2 C3 1.737(2) . ?
S2 C1 1.789(2) . ?
S3 C2 1.746(2) . ?
S3 C4 1.788(2) . ?
S4 C3 1.749(2) . ?
S4 C5 1.776(2) . ?
O1 C1 1.198(3) . ?
C2 C3 1.343(3) . ?
C4 C5 1.347(3) . ?
C4 C6 1.483(3) . ?
C5 C11 1.488(3) . ?
C6 C10 1.387(3) . ?
C6 C7 1.402(3) . ?
C7 C8 1.379(3) . ?
C7 H7 0.9500 . ?
C8 N1 1.342(3) . ?
C8 H8 0.9500 . ?
C9 N1 1.339(3) . ?
C9 C10 1.376(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.380(3) . ?
C11 C15 1.393(3) . ?
C12 C13 1.381(3) . ?
C12 H12 0.9500 . ?
C13 N2 1.337(3) . ?
C13 H13 0.9500 . ?
C14 N2 1.323(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N3 C19 1.327(3) . ?
N3 C20 1.339(3) . ?
C16 C16 1.198(5) 7_565 ?
C16 C17 1.434(3) . ?
C17 C21 1.387(3) . ?
C17 C18 1.396(3) . ?
C18 C19 1.383(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.381(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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 95.75(11) . . ?
C3 S2 C1 95.74(11) . . ?
C2 S3 C4 100.06(10) . . ?
C3 S4 C5 100.62(10) . . ?
O1 C1 S1 123.79(18) . . ?
O1 C1 S2 123.68(18) . . ?
S1 C1 S2 112.52(14) . . ?
C3 C2 S1 118.11(18) . . ?
C3 C2 S3 121.66(17) . . ?
S1 C2 S3 120.20(12) . . ?
C2 C3 S2 117.52(17) . . ?
C2 C3 S4 122.26(18) . . ?
S2 C3 S4 120.21(12) . . ?
C5 C4 C6 126.74(18) . . ?
C5 C4 S3 120.63(16) . . ?
C6 C4 S3 112.63(14) . . ?
C4 C5 C11 125.00(19) . . ?
C4 C5 S4 121.66(16) . . ?
C11 C5 S4 113.18(14) . . ?
C10 C6 C7 117.42(19) . . ?
C10 C6 C4 120.50(18) . . ?
C7 C6 C4 121.91(19) . . ?
C8 C7 C6 118.7(2) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
N1 C8 C7 124.3(2) . . ?
N1 C8 H8 117.9 . . ?
C7 C8 H8 117.9 . . ?
N1 C9 C10 124.1(2) . . ?
N1 C9 H9 117.9 . . ?
C10 C9 H9 117.9 . . ?
C9 C10 C6 119.38(19) . . ?
C9 C10 H10 120.3 . . ?
C6 C10 H10 120.3 . . ?
C12 C11 C15 118.05(19) . . ?
C12 C11 C5 120.17(19) . . ?
C15 C11 C5 121.7(2) . . ?
C11 C12 C13 118.8(2) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
N2 C13 C12 124.1(2) . . ?
N2 C13 H13 117.9 . . ?
C12 C13 H13 117.9 . . ?
N2 C14 C15 124.5(2) . . ?
N2 C14 H14 117.7 . . ?
C15 C14 H14 117.7 . . ?
C14 C15 C11 118.2(2) . . ?
C14 C15 H15 120.9 . . ?
C11 C15 H15 120.9 . . ?
C9 N1 C8 116.08(19) . . ?
C14 N2 C13 116.23(18) . . ?
C19 N3 C20 116.0(2) . . ?
C16 C16 C17 178.4(3) 7_565 . ?
C21 C17 C18 117.7(2) . . ?
C21 C17 C16 121.8(2) . . ?
C18 C17 C16 120.4(2) . . ?
C19 C18 C17 118.5(2) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
N3 C19 C18 124.6(2) . . ?
N3 C19 H19 117.7 . . ?
C18 C19 H19 117.7 . . ?
N3 C20 C21 124.4(2) . . ?
N3 C20 H20 117.8 . . ?
C21 C20 H20 117.8 . . ?
C20 C21 C17 118.7(2) . . ?
C20 C21 H21 120.6 . . ?
C17 C21 H21 120.6 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.061