#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/73/2217342.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2217342
loop_
_publ_author_name
'Tanui, Hillary K.'
'Fronczek, Frank R.'
'Vicente, M. Graça H.'
_publ_section_title
;
 Bis(1-tosyl-2-pyrrolyl)ethyne
;
_journal_coeditor_code           TK2223
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o130
_journal_page_last               o130
_journal_paper_doi               10.1107/S1600536807062964
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C24 H20 N2 O4 S2'
_chemical_formula_moiety         'C24 H20 N2 O4 S2'
_chemical_formula_sum            'C24 H20 N2 O4 S2'
_chemical_formula_weight         464.54
_chemical_name_systematic
;
Bis(1-tosyl-2-pyrrolyl)ethyne
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 101.049(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5127(15)
_cell_length_b                   16.822(2)
_cell_length_c                   7.5311(11)
_cell_measurement_reflns_used    3246
_cell_measurement_temperature    90
_cell_measurement_theta_max      32.5
_cell_measurement_theta_min      2.5
_cell_volume                     1058.5(3)
_computing_cell_refinement       'HKL SCALEPACK (Otwinowski & Minor 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
;
HKL DENZO (Otwinowski & Minor 1997) and HKL SCALEPACK (Otwinowski &
Minor 1997)
;
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      90
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device       'Nonius KappaCCD (with Oxford Cryostream)'
_diffrn_measurement_method       'ω scans with κ offsets'
_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  0.019
_diffrn_reflns_av_sigmaI/netI    0.031
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16546
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         32.6
_diffrn_reflns_theta_min         2.7
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(HKL SCALEPACK; Otwinowski & Minor 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.54
_refine_ls_extinction_coef       0.0087(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         3565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.046
_refine_ls_R_factor_gt           0.037
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0457P)²+0.5421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.095
_refine_ls_wR_factor_ref         0.100
_reflns_number_gt                2995
_reflns_number_total             3565
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2223.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2217342
_cod_database_fobs_code          2217342
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.17966(3) 0.588570(17) 0.18361(4) 0.01389(9) Uani d . 1
O O1 0.03490(11) 0.62987(6) 0.10845(12) 0.0205(2) Uani d . 1
O O2 0.21216(11) 0.51113(5) 0.12117(12) 0.01826(19) Uani d . 1
N N1 0.17450(12) 0.58026(6) 0.40533(13) 0.01363(19) Uani d . 1
C C1 0.04720(14) 0.60559(7) 0.48222(16) 0.0155(2) Uani d . 1
H H1 -0.0438 0.6342 0.4222 0.019 Uiso calc R 1
C C2 0.07578(14) 0.58208(7) 0.65906(16) 0.0159(2) Uani d . 1
H H2 0.0083 0.5915 0.7437 0.019 Uiso calc R 1
C C3 0.22451(15) 0.54103(7) 0.69389(15) 0.0154(2) Uani d . 1
H H3 0.2736 0.5181 0.8061 0.018 Uiso calc R 1
C C4 0.28522(14) 0.54024(7) 0.53683(15) 0.0135(2) Uani d . 1
C C5 0.43438(14) 0.51145(7) 0.50710(15) 0.0143(2) Uani d . 1
C C6 0.34514(14) 0.64976(7) 0.17831(15) 0.0141(2) Uani d . 1
C C7 0.33400(15) 0.73131(7) 0.20914(16) 0.0169(2) Uani d . 1
H H7 0.2372 0.7541 0.2306 0.020 Uiso calc R 1
C C8 0.46788(16) 0.77829(7) 0.20758(17) 0.0187(2) Uani d . 1
H H8 0.4622 0.8338 0.2286 0.022 Uiso calc R 1
C C9 0.61100(15) 0.74548(8) 0.17564(16) 0.0183(2) Uani d . 1
C C10 0.61811(15) 0.66412(8) 0.14272(16) 0.0172(2) Uani d . 1
H H10 0.7143 0.6414 0.1193 0.021 Uiso calc R 1
C C11 0.48522(14) 0.61580(7) 0.14388(15) 0.0151(2) Uani d . 1
H H11 0.4903 0.5604 0.1214 0.018 Uiso calc R 1
C C12 0.75453(18) 0.79796(9) 0.1772(2) 0.0262(3) Uani d . 1
H H12A 0.8386 0.7676 0.1351 0.039 Uiso calc R 1
H H12B 0.7946 0.8170 0.3005 0.039 Uiso calc R 1
H H12C 0.7238 0.8435 0.0968 0.039 Uiso calc R 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle
O2 S1 O1 . 121.17(6)
O2 S1 N1 . 107.09(5)
O1 S1 N1 . 104.35(5)
O2 S1 C6 . 108.71(6)
O1 S1 C6 . 109.91(6)
N1 S1 C6 . 104.20(5)
C1 N1 C4 . 108.98(9)
C1 N1 S1 . 123.92(8)
C4 N1 S1 . 126.76(8)
C2 C1 N1 . 108.07(10)
C2 C1 H1 . 126.0
N1 C1 H1 . 126.0
C1 C2 C3 . 107.85(10)
C1 C2 H2 . 126.1
C3 C2 H2 . 126.1
C4 C3 C2 . 108.26(10)
C4 C3 H3 . 125.9
C2 C3 H3 . 125.9
C3 C4 N1 . 106.85(10)
C3 C4 C5 . 129.33(11)
N1 C4 C5 . 123.67(10)
C5 C5 C4 3_666 175.78(16)
C11 C6 C7 . 121.47(11)
C11 C6 S1 . 119.01(9)
C7 C6 S1 . 119.51(9)
C8 C7 C6 . 118.37(11)
C8 C7 H7 . 120.8
C6 C7 H7 . 120.8
C7 C8 C9 . 121.32(12)
C7 C8 H8 . 119.3
C9 C8 H8 . 119.3
C10 C9 C8 . 119.11(11)
C10 C9 C12 . 120.93(12)
C8 C9 C12 . 119.96(12)
C11 C10 C9 . 120.54(12)
C11 C10 H10 . 119.7
C9 C10 H10 . 119.7
C6 C11 C10 . 119.17(11)
C6 C11 H11 . 120.4
C10 C11 H11 . 120.4
C9 C12 H12A . 109.5
C9 C12 H12B . 109.5
H12A C12 H12B . 109.5
C9 C12 H12C . 109.5
H12A C12 H12C . 109.5
H12B C12 H12C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 O2 . 1.4298(10)
S1 O1 . 1.4333(10)
S1 N1 . 1.6845(10)
S1 C6 . 1.7513(12)
N1 C1 . 1.3900(15)
N1 C4 . 1.4016(15)
C1 C2 . 1.3656(17)
C1 H1 . 0.9500
C2 C3 . 1.4218(17)
C2 H2 . 0.9500
C3 C4 . 1.3786(16)
C3 H3 . 0.9500
C4 C5 . 1.4164(16)
C5 C5 3_666 1.206(2)
C6 C11 . 1.3907(17)
C6 C7 . 1.3977(17)
C7 C8 . 1.3888(18)
C7 H7 . 0.9500
C8 C9 . 1.3997(19)
C8 H8 . 0.9500
C9 C10 . 1.3945(18)
C9 C12 . 1.5056(18)
C10 C11 . 1.3944(17)
C10 H10 . 0.9500
C11 H11 . 0.9500
C12 H12A . 0.9800
C12 H12B . 0.9800
C12 H12C . 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C3 H3 O2 1_556 0.95 2.53 3.278(2) 136 y
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
O2 S1 N1 C1 -126.14(10)
O1 S1 N1 C1 3.48(11)
C6 S1 N1 C1 118.78(10)
O2 S1 N1 C4 46.48(11)
O1 S1 N1 C4 176.09(10)
C6 S1 N1 C4 -68.61(11)
C4 N1 C1 C2 -0.14(13)
S1 N1 C1 C2 173.61(9)
N1 C1 C2 C3 -0.01(14)
C1 C2 C3 C4 0.16(14)
C2 C3 C4 N1 -0.24(13)
C2 C3 C4 C5 175.18(12)
C1 N1 C4 C3 0.23(13)
S1 N1 C4 C3 -173.29(9)
C1 N1 C4 C5 -175.51(11)
S1 N1 C4 C5 10.97(17)
O2 S1 C6 C11 -9.04(11)
O1 S1 C6 C11 -143.78(9)
N1 S1 C6 C11 104.90(10)
O2 S1 C6 C7 171.15(9)
O1 S1 C6 C7 36.41(11)
N1 S1 C6 C7 -74.92(10)
C11 C6 C7 C8 -1.01(17)
S1 C6 C7 C8 178.80(9)
C6 C7 C8 C9 0.15(18)
C7 C8 C9 C10 0.76(18)
C7 C8 C9 C12 -179.25(12)
C8 C9 C10 C11 -0.83(18)
C12 C9 C10 C11 179.17(11)
C7 C6 C11 C10 0.93(17)
S1 C6 C11 C10 -178.88(9)
C9 C10 C11 C6 0.01(17)
