#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/26/2202660.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_2202660
loop_
_publ_author_name
'Gott, Andrew L.'
'McGowan, Patrick C.'
_publ_section_title
;
 1,4,7-Tris(p-toluenesulfonyl)-1,4,7-triazacyclononane
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1702
_journal_page_last               o1703
_journal_paper_doi               10.1107/S1600536803022384
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C27 H33 N3 O6 S3'
_chemical_formula_moiety         'C27 H33 N3 O6 S3'
_chemical_formula_sum            'C27 H33 N3 O6 S3'
_chemical_formula_weight         591.74
_chemical_name_systematic
;
1,4,7-tris(p-toluenesulphonyl)-1,4,7-triazacyclononane
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                101.5528(8)
_cell_angle_beta                 113.5558(8)
_cell_angle_gamma                96.3429(6)
_cell_formula_units_Z            2
_cell_length_a                   10.3019(2)
_cell_length_b                   12.3216(2)
_cell_length_c                   12.6131(2)
_cell_measurement_reflns_used    29674
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.8
_cell_volume                     1405.18(4)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1996)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'XSeed (Barbour, 1999)'
_computing_publication_material  'local program'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       area-detector
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.1268
_diffrn_reflns_av_sigmaI/netI    0.0796
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29674
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.79
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.9667
_exptl_absorpt_correction_T_min  0.9320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.953
_refine_diff_density_min         -1.272
_refine_ls_extinction_coef       0.047(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         6402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0408
_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)+(0.0762P)²+0.4075P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1335
_reflns_number_gt                5459
_reflns_number_total             6402
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg6000.cif
_cod_data_source_block           I
_cod_original_cell_volume        1405.22(4)
_cod_database_code               2202660
_cod_database_fobs_code          2202660
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 0.48822(4) 0.33243(3) 0.22081(4) 0.02576(14) Uani d . 1 . . S
S4 0.83908(4) -0.00535(3) 0.23646(3) 0.02527(14) Uani d . 1 . . S
S7 0.33381(5) -0.14779(4) 0.16906(4) 0.03064(15) Uani d . 1 . . S
O11 0.63193(14) 0.37106(10) 0.23413(12) 0.0324(3) Uani d . 1 . . O
O12 0.45738(14) 0.35860(11) 0.32327(11) 0.0318(3) Uani d . 1 . . O
O41 0.82573(14) -0.04532(11) 0.11719(11) 0.0322(3) Uani d . 1 . . O
O42 0.84549(13) -0.08322(10) 0.30824(11) 0.0310(3) Uani d . 1 . . O
O71 0.43276(17) -0.21330(12) 0.15010(14) 0.0431(4) Uani d . 1 . . O
O72 0.21284(15) -0.13421(11) 0.06850(11) 0.0378(3) Uani d . 1 . . O
N1 0.45143(15) 0.19480(11) 0.17298(12) 0.0253(3) Uani d . 1 . . N
N4 0.70007(15) 0.05222(12) 0.22742(12) 0.0248(3) Uani d . 1 . . N
N7 0.42815(16) -0.01995(12) 0.24801(13) 0.0289(3) Uani d . 1 . . N
C2 0.51233(18) 0.13933(15) 0.09309(15) 0.0271(3) Uani d . 1 . . C
H2A 0.4995 0.1799 0.0305 0.032 Uiso calc R 1 . . H
H2B 0.4554 0.0608 0.0521 0.032 Uiso calc R 1 . . H
C3 0.67133(18) 0.13517(14) 0.15477(15) 0.0263(3) Uani d . 1 . . C
H3A 0.7074 0.1159 0.0929 0.032 Uiso calc R 1 . . H
H3B 0.7266 0.2115 0.2076 0.032 Uiso calc R 1 . . H
C5 0.68379(19) 0.08199(15) 0.34071(14) 0.0276(4) Uani d . 1 . . C
H5A 0.6531 0.1554 0.3489 0.033 Uiso calc R 1 . . H
H5B 0.7787 0.0911 0.4095 0.033 Uiso calc R 1 . . H
C6 0.5734(2) -0.00796(16) 0.34421(16) 0.0327(4) Uani d . 1 . . C
H6A 0.6036 -0.0815 0.3355 0.039 Uiso calc R 1 . . H
H6B 0.5701 0.0128 0.4230 0.039 Uiso calc R 1 . . H
C8 0.3470(2) 0.06908(15) 0.26399(16) 0.0290(4) Uani d . 1 . . C
H8A 0.4034 0.1231 0.3442 0.035 Uiso calc R 1 . . H
H8B 0.2538 0.0337 0.2606 0.035 Uiso calc R 1 . . H
C9 0.31693(18) 0.13343(15) 0.16844(16) 0.0279(4) Uani d . 1 . . C
H9A 0.2607 0.0793 0.0882 0.034 Uiso calc R 1 . . H
H9B 0.2572 0.1883 0.1797 0.034 Uiso calc R 1 . . H
C11 0.37034(19) 0.39008(14) 0.11166(15) 0.0281(4) Uani d . 1 . . C
C12 0.3769(2) 0.38062(17) 0.00178(18) 0.0376(4) Uani d . 1 . . C
H12 0.4386 0.3374 -0.0183 0.045 Uiso calc R 1 . . H
C13 0.2811(2) 0.45412(15) 0.14099(17) 0.0324(4) Uani d . 1 . . C
H13 0.2767 0.4604 0.2157 0.039 Uiso calc R 1 . . H
C14 0.2916(2) 0.43552(18) -0.07774(18) 0.0397(4) Uani d . 1 . . C
H14 0.2941 0.4279 -0.1533 0.048 Uiso calc R 1 . . H
C15 0.1983(2) 0.50902(16) 0.06064(18) 0.0354(4) Uani d . 1 . . C
H15 0.1371 0.5528 0.0810 0.042 Uiso calc R 1 . . H
C16 0.2031(2) 0.50115(16) -0.04922(18) 0.0348(4) Uani d . 1 . . C
C17 0.1151(2) 0.56421(19) -0.1339(2) 0.0437(5) Uani d . 1 . . C
H17A 0.0154 0.5203 -0.1802 0.065 Uiso calc R 1 . . H
H17B 0.1579 0.5750 -0.1888 0.065 Uiso calc R 1 . . H
H17C 0.1149 0.6382 -0.0876 0.065 Uiso calc R 1 . . H
C41 0.99340(18) 0.10614(15) 0.31701(15) 0.0269(3) Uani d . 1 . . C
C42 1.07821(19) 0.11897(15) 0.43807(16) 0.0305(4) Uani d . 1 . . C
H42 1.0601 0.0631 0.4754 0.037 Uiso calc R 1 . . H
C43 1.02154(19) 0.18701(16) 0.26112(16) 0.0307(4) Uani d . 1 . . C
H43 0.9654 0.1773 0.1778 0.037 Uiso calc R 1 . . H
C44 1.18978(19) 0.21384(16) 0.50442(16) 0.0319(4) Uani d . 1 . . C
H44 1.2483 0.2218 0.5870 0.038 Uiso calc R 1 . . H
C45 1.1325(2) 0.28142(16) 0.32901(17) 0.0327(4) Uani d . 1 . . C
H45 1.1516 0.3367 0.2914 0.039 Uiso calc R 1 . . H
C46 1.21725(19) 0.29733(15) 0.45199(17) 0.0300(4) Uani d . 1 . . C
C47 1.3314(2) 0.40341(16) 0.52600(19) 0.0383(4) Uani d . 1 . . C
H47A 1.2861 0.4637 0.5500 0.057 Uiso calc R 1 . . H
H47B 1.3791 0.4270 0.4785 0.057 Uiso calc R 1 . . H
H47C 1.4032 0.3887 0.5978 0.057 Uiso calc R 1 . . H
C71 0.26464(19) -0.20670(14) 0.25741(15) 0.0278(4) Uani d . 1 . . C
C72 0.12291(19) -0.20614(15) 0.24088(16) 0.0314(4) Uani d . 1 . . C
H72 0.0630 -0.1721 0.1835 0.038 Uiso calc R 1 . . H
C73 0.3529(2) -0.25481(16) 0.34303(17) 0.0321(4) Uani d . 1 . . C
H73 0.4502 -0.2538 0.3552 0.039 Uiso calc R 1 . . H
C74 0.0699(2) -0.25599(16) 0.30935(17) 0.0335(4) Uani d . 1 . . C
H74 -0.0269 -0.2556 0.2983 0.040 Uiso calc R 1 . . H
C75 0.2988(2) -0.30423(16) 0.41064(17) 0.0327(4) Uani d . 1 . . C
H75 0.3596 -0.3369 0.4690 0.039 Uiso calc R 1 . . H
C76 0.1562(2) -0.30655(15) 0.39405(16) 0.0311(4) Uani d . 1 . . C
C77 0.0959(2) -0.36358(18) 0.46476(19) 0.0403(5) Uani d . 1 . . C
H77A 0.0457 -0.4417 0.4180 0.060 Uiso calc R 1 . . H
H77B 0.0275 -0.3220 0.4817 0.060 Uiso calc R 1 . . H
H77C 0.1753 -0.3641 0.5405 0.060 Uiso calc R 1 . . H
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
_geom_angle_publ_flag
O12 S1 O11 119.47(8) yes
O12 S1 N1 106.29(7) ?
O11 S1 N1 106.81(7) yes
O12 S1 C11 106.94(8) ?
O11 S1 C11 106.96(8) ?
N1 S1 C11 110.24(8) yes
O41 S4 O42 119.77(8) ?
O41 S4 N4 107.68(7) ?
O42 S4 N4 106.39(7) ?
O41 S4 C41 108.25(8) ?
O42 S4 C41 108.20(8) ?
N4 S4 C41 105.71(8) ?
O71 S7 O72 120.17(9) ?
O71 S7 N7 107.04(8) ?
O72 S7 N7 106.24(8) ?
O71 S7 C71 107.63(8) ?
O72 S7 C71 107.49(8) ?
N7 S7 C71 107.73(8) ?
C9 N1 C2 118.66(13) ?
C9 N1 S1 117.15(11) ?
C2 N1 S1 119.59(11) yes
C3 N4 C5 116.22(13) yes
C3 N4 S4 115.67(11) ?
C5 N4 S4 114.89(10) ?
C6 N7 C8 117.34(14) ?
C6 N7 S7 118.29(12) ?
C8 N7 S7 117.42(12) ?
N1 C2 C3 115.41(13) yes
N1 C2 H2A 108.4 ?
C3 C2 H2A 108.4 ?
N1 C2 H2B 108.4 ?
C3 C2 H2B 108.4 ?
H2A C2 H2B 107.5 ?
N4 C3 C2 113.94(14) yes
N4 C3 H3A 108.8 ?
C2 C3 H3A 108.8 ?
N4 C3 H3B 108.8 ?
C2 C3 H3B 108.8 ?
H3A C3 H3B 107.7 ?
N4 C5 C6 111.89(14) ?
N4 C5 H5A 109.2 ?
C6 C5 H5A 109.2 ?
N4 C5 H5B 109.2 ?
C6 C5 H5B 109.2 ?
H5A C5 H5B 107.9 ?
N7 C6 C5 111.47(14) ?
N7 C6 H6A 109.3 ?
C5 C6 H6A 109.3 ?
N7 C6 H6B 109.3 ?
C5 C6 H6B 109.3 ?
H6A C6 H6B 108.0 ?
N7 C8 C9 112.19(14) ?
N7 C8 H8A 109.2 ?
C9 C8 H8A 109.2 ?
N7 C8 H8B 109.2 ?
C9 C8 H8B 109.2 ?
H8A C8 H8B 107.9 ?
N1 C9 C8 112.33(14) ?
N1 C9 H9A 109.1 ?
C8 C9 H9A 109.1 ?
N1 C9 H9B 109.1 ?
C8 C9 H9B 109.1 ?
H9A C9 H9B 107.9 ?
C13 C11 C12 120.28(16) ?
C13 C11 S1 118.94(14) ?
C12 C11 S1 120.50(14) ?
C14 C12 C11 118.97(18) ?
C14 C12 H12 120.5 ?
C11 C12 H12 120.5 ?
C11 C13 C15 119.63(17) ?
C11 C13 H13 120.2 ?
C15 C13 H13 120.2 ?
C16 C14 C12 121.51(18) ?
C16 C14 H14 119.2 ?
C12 C14 H14 119.2 ?
C13 C15 C16 121.20(18) ?
C13 C15 H15 119.4 ?
C16 C15 H15 119.4 ?
C14 C16 C15 118.39(17) ?
C14 C16 C17 121.29(18) ?
C15 C16 C17 120.31(18) ?
C16 C17 H17A 109.5 ?
C16 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C16 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
C42 C41 C43 120.33(16) ?
C42 C41 S4 119.88(13) ?
C43 C41 S4 119.53(13) ?
C41 C42 C44 119.74(16) ?
C41 C42 H42 120.1 ?
C44 C42 H42 120.1 ?
C45 C43 C41 119.05(16) ?
C45 C43 H43 120.5 ?
C41 C43 H43 120.5 ?
C42 C44 C46 121.13(17) ?
C42 C44 H44 119.4 ?
C46 C44 H44 119.4 ?
C43 C45 C46 121.53(16) ?
C43 C45 H45 119.2 ?
C46 C45 H45 119.2 ?
C44 C46 C45 118.19(17) ?
C44 C46 C47 120.86(17) ?
C45 C46 C47 120.92(16) ?
C46 C47 H47A 109.5 ?
C46 C47 H47B 109.5 ?
H47A C47 H47B 109.5 ?
C46 C47 H47C 109.5 ?
H47A C47 H47C 109.5 ?
H47B C47 H47C 109.5 ?
C73 C71 C72 120.20(16) ?
C73 C71 S7 119.34(13) ?
C72 C71 S7 120.45(13) ?
C71 C72 C74 119.27(16) ?
C71 C72 H72 120.4 ?
C74 C72 H72 120.4 ?
C75 C73 C71 119.99(17) ?
C75 C73 H73 120.0 ?
C71 C73 H73 120.0 ?
C72 C74 C76 121.20(17) ?
C72 C74 H74 119.4 ?
C76 C74 H74 119.4 ?
C73 C75 C76 120.81(17) ?
C73 C75 H75 119.6 ?
C76 C75 H75 119.6 ?
C75 C76 C74 118.51(16) ?
C75 C76 C77 120.84(17) ?
C74 C76 C77 120.65(17) ?
C76 C77 H77A 109.5 ?
C76 C77 H77B 109.5 ?
H77A C77 H77B 109.5 ?
C76 C77 H77C 109.5 ?
H77A C77 H77C 109.5 ?
H77B C77 H77C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O12 . 1.4349(13) ?
S1 O11 . 1.4353(13) yes
S1 N1 . 1.6277(14) yes
S1 C11 . 1.7664(17) yes
S4 O41 . 1.4310(12) ?
S4 O42 . 1.4350(12) ?
S4 N4 . 1.6411(14) ?
S4 C41 . 1.7647(18) ?
S7 O71 . 1.4309(14) ?
S7 O72 . 1.4342(14) ?
S7 N7 . 1.6364(15) ?
S7 C71 . 1.7667(17) ?
N1 C9 . 1.477(2) ?
N1 C2 . 1.483(2) yes
N4 C3 . 1.482(2) ?
N4 C5 . 1.483(2) ?
N7 C6 . 1.470(2) ?
N7 C8 . 1.481(2) ?
C2 C3 . 1.519(2) yes
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C5 C6 . 1.518(2) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C8 C9 . 1.522(2) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C11 C13 . 1.386(2) ?
C11 C12 . 1.397(3) ?
C12 C14 . 1.390(3) ?
C12 H12 . 0.9500 ?
C13 C15 . 1.387(3) ?
C13 H13 . 0.9500 ?
C14 C16 . 1.387(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.391(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.510(3) ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C41 C42 . 1.388(2) ?
C41 C43 . 1.398(2) ?
C42 C44 . 1.389(3) ?
C42 H42 . 0.9500 ?
C43 C45 . 1.385(3) ?
C43 H43 . 0.9500 ?
C44 C46 . 1.391(3) ?
C44 H44 . 0.9500 ?
C45 C46 . 1.402(3) ?
C45 H45 . 0.9500 ?
C46 C47 . 1.502(3) ?
C47 H47A . 0.9800 ?
C47 H47B . 0.9800 ?
C47 H47C . 0.9800 ?
C71 C73 . 1.391(2) ?
C71 C72 . 1.391(3) ?
C72 C74 . 1.392(3) ?
C72 H72 . 0.9500 ?
C73 C75 . 1.386(3) ?
C73 H73 . 0.9500 ?
C74 C76 . 1.396(3) ?
C74 H74 . 0.9500 ?
C75 C76 . 1.395(3) ?
C75 H75 . 0.9500 ?
C76 C77 . 1.508(3) ?
C77 H77A . 0.9800 ?
C77 H77B . 0.9800 ?
C77 H77C . 0.9800 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 490460
2 PubChem 564157
