# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2010

data_global

_journal_coden_Cambridge         440
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Liu, Shenghua'

_publ_contact_author_name        'Liu, Shenghua'
_publ_contact_author_email       chshliu@mail.ccnu.edu.cn

_publ_section_title              
;
Substituted diethynyldithia[3.3]paracyclophanes
a synthetically more accessible new building blocks
for molecular scaffolding
;

# Attachment '- t.cif'

data_t
_database_code_depnum_ccdc_archive 'CCDC 784609'
#TrackingRef '- t.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H10 Br2 F4 S2'
_chemical_formula_weight         502.18

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'
F F 0.0171 0.0103 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Fdd2

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

_cell_length_a                   25.726(2)
_cell_length_b                   28.737(3)
_cell_length_c                   9.0939(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6723.1(11)
_cell_formula_units_Z            16
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3552
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      23.74

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.985
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3904
_exptl_absorpt_coefficient_mu    5.107
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.4282
_exptl_absorpt_correction_T_max  0.6291
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11877
_diffrn_reflns_av_R_equivalents  0.1818
_diffrn_reflns_av_sigmaI/netI    0.1117
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3157
_reflns_number_gt                2157
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.1073P)^2^+0.0000P] 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    mixed
_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   -0.005(18)
_refine_ls_number_reflns         3157
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0754
_refine_ls_wR_factor_ref         0.1829
_refine_ls_wR_factor_gt          0.1728
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_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
Br1 Br 0.35835(5) 0.04240(3) 1.18538(13) 0.0746(4) Uani 1 1 d . . .
Br2 Br 0.41562(5) 0.16708(4) 0.60783(13) 0.0786(4) Uani 1 1 d . . .
C1 C 0.2528(3) 0.1424(3) 0.9115(14) 0.061(3) Uani 1 1 d . . .
C2 C 0.2496(3) 0.0940(3) 0.9178(12) 0.053(2) Uani 1 1 d . . .
C3 C 0.2606(3) 0.0662(3) 0.7995(11) 0.0504(19) Uani 1 1 d . . .
C4 C 0.2750(3) 0.0838(3) 0.6662(11) 0.0503(18) Uani 1 1 d . . .
C5 C 0.2746(3) 0.1322(3) 0.6563(11) 0.057(2) Uani 1 1 d . . .
C6 C 0.2651(4) 0.1608(2) 0.7738(15) 0.064(3) Uani 1 1 d . . .
C7 C 0.2445(5) 0.1704(4) 1.0457(18) 0.087(4) Uani 1 1 d . . .
H7A H 0.2312 0.1502 1.1225 0.105 Uiso 1 1 calc R . .
H7B H 0.2180 0.1936 1.0254 0.105 Uiso 1 1 calc R . .
C8 C 0.3473(5) 0.1528(3) 1.1554(11) 0.069(3) Uani 1 1 d . . .
H8A H 0.3762 0.1652 1.2114 0.083 Uiso 1 1 calc R . .
H8B H 0.3295 0.1303 1.2172 0.083 Uiso 1 1 calc R . .
C9 C 0.3684(3) 0.1278(2) 1.0224(10) 0.0447(17) Uani 1 1 d . . .
C10 C 0.3720(3) 0.0797(3) 1.0182(10) 0.0475(18) Uani 1 1 d . . .
C11 C 0.3849(3) 0.0576(2) 0.8886(10) 0.0439(17) Uani 1 1 d . . .
H11 H 0.3868 0.0253 0.8886 0.053 Uiso 1 1 calc R . .
C12 C 0.3951(3) 0.0809(3) 0.7586(11) 0.0478(18) Uani 1 1 d . . .
C13 C 0.3977(3) 0.1290(3) 0.7707(10) 0.0464(17) Uani 1 1 d . . .
C14 C 0.3835(3) 0.1521(3) 0.8994(10) 0.0499(19) Uani 1 1 d . . .
H14 H 0.3842 0.1844 0.9020 0.060 Uiso 1 1 calc R . .
C15 C 0.4000(4) 0.0559(3) 0.6120(12) 0.065(3) Uani 1 1 d . . .
H15A H 0.4327 0.0392 0.6099 0.078 Uiso 1 1 calc R . .
H15B H 0.4007 0.0788 0.5337 0.078 Uiso 1 1 calc R . .
C16 C 0.2920(4) 0.0527(4) 0.5436(11) 0.067(2) Uani 1 1 d . . .
H16A H 0.3000 0.0720 0.4591 0.080 Uiso 1 1 calc R . .
H16B H 0.2629 0.0330 0.5168 0.080 Uiso 1 1 calc R . .
F1 F 0.2380(3) 0.0727(2) 1.0502(8) 0.0842(19) Uani 1 1 d . . .
F2 F 0.2587(3) 0.01988(17) 0.8184(8) 0.0824(18) Uani 1 1 d . . .
F3 F 0.2869(3) 0.1517(2) 0.5228(9) 0.090(2) Uani 1 1 d . . .
F4 F 0.2661(3) 0.2058(2) 0.7526(13) 0.111(3) Uani 1 1 d . . .
S3 S 0.34756(10) 0.01541(7) 0.5781(3) 0.0575(5) Uani 1 1 d . . .
S4 S 0.30279(11) 0.19993(7) 1.1141(4) 0.0695(7) Uani 1 1 d . . .

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
Br1 0.1147(9) 0.0641(5) 0.0451(5) 0.0091(4) 0.0029(6) 0.0069(5)
Br2 0.0922(7) 0.0795(7) 0.0641(7) 0.0122(5) 0.0186(6) -0.0214(5)
C1 0.038(4) 0.063(5) 0.083(8) -0.017(5) -0.001(5) 0.011(3)
C2 0.034(4) 0.068(5) 0.056(5) -0.006(4) 0.004(4) -0.005(3)
C3 0.055(4) 0.043(4) 0.054(5) -0.001(4) -0.005(4) -0.002(3)
C4 0.048(4) 0.058(4) 0.045(5) 0.002(4) -0.010(4) -0.003(3)
C5 0.050(4) 0.069(5) 0.053(6) 0.014(4) -0.012(4) -0.003(4)
C6 0.067(5) 0.026(3) 0.100(9) 0.001(4) -0.010(6) 0.007(3)
C7 0.074(6) 0.082(7) 0.106(11) -0.037(7) 0.019(7) 0.000(5)
C8 0.099(7) 0.067(5) 0.041(6) -0.012(4) 0.004(5) 0.013(5)
C9 0.051(4) 0.044(4) 0.038(4) -0.008(3) -0.010(3) 0.004(3)
C10 0.049(4) 0.052(4) 0.041(4) -0.003(3) -0.012(4) 0.006(3)
C11 0.045(4) 0.040(3) 0.047(5) -0.008(3) 0.001(3) -0.001(3)
C12 0.038(4) 0.055(4) 0.050(5) -0.012(4) 0.008(3) -0.001(3)
C13 0.041(4) 0.054(4) 0.044(4) 0.002(3) 0.004(4) -0.003(3)
C14 0.050(4) 0.046(4) 0.054(5) -0.008(3) -0.009(4) -0.001(3)
C15 0.077(6) 0.068(5) 0.051(6) -0.017(5) 0.025(5) -0.013(4)
C16 0.086(7) 0.080(6) 0.035(5) -0.008(4) -0.009(5) 0.002(5)
F1 0.089(4) 0.100(4) 0.063(4) -0.016(3) 0.034(3) -0.026(3)
F2 0.119(4) 0.060(3) 0.068(4) -0.006(3) 0.018(4) -0.018(3)
F3 0.109(5) 0.091(4) 0.071(5) 0.031(4) -0.014(4) -0.005(4)
F4 0.114(5) 0.064(4) 0.155(9) 0.004(4) -0.006(6) 0.016(3)
S3 0.0815(14) 0.0501(10) 0.0410(11) -0.0110(9) 0.0055(11) -0.0020(9)
S4 0.0879(16) 0.0502(11) 0.0704(17) -0.0170(11) 0.0119(14) 0.0034(10)

_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
Br1 C10 1.893(9) . ?
Br2 C13 1.899(9) . ?
C1 C2 1.394(12) . ?
C1 C6 1.396(17) . ?
C1 C7 1.478(16) . ?
C2 C3 1.371(13) . ?
C2 F1 1.383(12) . ?
C3 F2 1.343(9) . ?
C3 C4 1.364(14) . ?
C4 C5 1.392(12) . ?
C4 C16 1.495(13) . ?
C5 C6 1.371(16) . ?
C5 F3 1.375(13) . ?
C6 F4 1.308(10) . ?
C7 S4 1.833(13) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.507(12) . ?
C8 S4 1.813(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.374(13) . ?
C9 C10 1.385(11) . ?
C10 C11 1.380(12) . ?
C11 C12 1.384(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(11) . ?
C12 C15 1.519(13) . ?
C13 C14 1.395(13) . ?
C14 H14 0.9300 . ?
C15 S3 1.808(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 S3 1.813(11) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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 C1 C6 115.4(9) . . ?
C2 C1 C7 120.0(11) . . ?
C6 C1 C7 124.5(9) . . ?
C3 C2 F1 118.0(7) . . ?
C3 C2 C1 122.5(10) . . ?
F1 C2 C1 119.4(9) . . ?
F2 C3 C4 119.5(8) . . ?
F2 C3 C2 118.0(8) . . ?
C4 C3 C2 122.5(7) . . ?
C3 C4 C5 115.2(9) . . ?
C3 C4 C16 121.3(8) . . ?
C5 C4 C16 123.5(9) . . ?
C6 C5 F3 118.9(8) . . ?
C6 C5 C4 123.4(9) . . ?
F3 C5 C4 117.6(9) . . ?
F4 C6 C5 118.4(12) . . ?
F4 C6 C1 120.8(11) . . ?
C5 C6 C1 120.7(7) . . ?
C1 C7 S4 114.4(8) . . ?
C1 C7 H7A 108.7 . . ?
S4 C7 H7A 108.7 . . ?
C1 C7 H7B 108.7 . . ?
S4 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 S4 114.7(7) . . ?
C9 C8 H8A 108.6 . . ?
S4 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
S4 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C14 C9 C10 117.7(8) . . ?
C14 C9 C8 120.9(7) . . ?
C10 C9 C8 121.4(9) . . ?
C11 C10 C9 119.9(8) . . ?
C11 C10 Br1 118.0(5) . . ?
C9 C10 Br1 122.1(7) . . ?
C10 C11 C12 123.5(6) . . ?
C10 C11 H11 118.2 . . ?
C12 C11 H11 118.2 . . ?
C11 C12 C13 115.1(8) . . ?
C11 C12 C15 122.4(7) . . ?
C13 C12 C15 122.4(9) . . ?
C12 C13 C14 121.9(8) . . ?
C12 C13 Br2 121.6(7) . . ?
C14 C13 Br2 116.3(6) . . ?
C9 C14 C13 121.0(7) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C12 C15 S3 113.1(6) . . ?
C12 C15 H15A 109.0 . . ?
S3 C15 H15A 109.0 . . ?
C12 C15 H15B 109.0 . . ?
S3 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C4 C16 S3 117.1(7) . . ?
C4 C16 H16A 108.0 . . ?
S3 C16 H16A 108.0 . . ?
C4 C16 H16B 108.0 . . ?
S3 C16 H16B 108.0 . . ?
H16A C16 H16B 107.3 . . ?
C15 S3 C16 103.7(5) . . ?
C8 S4 C7 104.0(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
C6 C1 C2 C3 3.7(12) . . . . ?
C7 C1 C2 C3 -175.1(9) . . . . ?
C6 C1 C2 F1 179.4(8) . . . . ?
C7 C1 C2 F1 0.6(12) . . . . ?
F1 C2 C3 F2 1.2(12) . . . . ?
C1 C2 C3 F2 177.0(8) . . . . ?
F1 C2 C3 C4 -176.8(8) . . . . ?
C1 C2 C3 C4 -0.9(14) . . . . ?
F2 C3 C4 C5 178.4(8) . . . . ?
C2 C3 C4 C5 -3.6(13) . . . . ?
F2 C3 C4 C16 -4.2(13) . . . . ?
C2 C3 C4 C16 173.7(8) . . . . ?
C3 C4 C5 C6 5.6(13) . . . . ?
C16 C4 C5 C6 -171.7(9) . . . . ?
C3 C4 C5 F3 -177.7(8) . . . . ?
C16 C4 C5 F3 4.9(13) . . . . ?
F3 C5 C6 F4 2.8(14) . . . . ?
C4 C5 C6 F4 179.4(8) . . . . ?
F3 C5 C6 C1 -179.6(8) . . . . ?
C4 C5 C6 C1 -3.0(15) . . . . ?
C2 C1 C6 F4 175.8(8) . . . . ?
C7 C1 C6 F4 -5.5(15) . . . . ?
C2 C1 C6 C5 -1.7(13) . . . . ?
C7 C1 C6 C5 177.0(9) . . . . ?
C2 C1 C7 S4 111.5(10) . . . . ?
C6 C1 C7 S4 -67.1(13) . . . . ?
S4 C8 C9 C14 41.5(12) . . . . ?
S4 C8 C9 C10 -136.7(8) . . . . ?
C14 C9 C10 C11 -6.8(12) . . . . ?
C8 C9 C10 C11 171.4(9) . . . . ?
C14 C9 C10 Br1 174.4(6) . . . . ?
C8 C9 C10 Br1 -7.4(12) . . . . ?
C9 C10 C11 C12 0.3(12) . . . . ?
Br1 C10 C11 C12 179.2(6) . . . . ?
C10 C11 C12 C13 7.5(12) . . . . ?
C10 C11 C12 C15 -169.2(8) . . . . ?
C11 C12 C13 C14 -9.1(12) . . . . ?
C15 C12 C13 C14 167.6(8) . . . . ?
C11 C12 C13 Br2 175.9(6) . . . . ?
C15 C12 C13 Br2 -7.3(11) . . . . ?
C10 C9 C14 C13 5.2(12) . . . . ?
C8 C9 C14 C13 -173.0(8) . . . . ?
C12 C13 C14 C9 3.0(13) . . . . ?
Br2 C13 C14 C9 178.2(6) . . . . ?
C11 C12 C15 S3 48.3(11) . . . . ?
C13 C12 C15 S3 -128.2(8) . . . . ?
C3 C4 C16 S3 -58.6(12) . . . . ?
C5 C4 C16 S3 118.6(9) . . . . ?
C12 C15 S3 C16 71.3(9) . . . . ?
C4 C16 S3 C15 -62.3(9) . . . . ?
C9 C8 S4 C7 70.2(10) . . . . ?
C1 C7 S4 C8 -61.0(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.459
_refine_diff_density_min         -0.995
_refine_diff_density_rms         0.222