#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/55/2105511.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_2105511
loop_
_publ_author_name
'Ferguson, G.'
'Glidewell, C.'
'Gregson, R. M.'
'Meehan, P. R.'
_publ_section_title
;
 Crystal Engineering Using Bis- and Tris-phenols. Adducts with
 1,4,8,11-Tetraazacyclotetradecane (Cyclam): Isolated Ladders in the
 Adduct with 4,4'-Thiodiphenol, Tethered Ladders in the Adduct with
 4,4'-Sulfonyldiphenol and Two Interwoven Three-Dimensional Networks in
 the Adduct with 1,1,1-Tris(4-hydroxyphenyl)ethane
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              139
_journal_page_last               150
_journal_paper_doi               10.1107/S0108768197010136
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C34 H44 N4 O4 S2 '
_chemical_formula_sum            'C34 H44 N4 O4 S2'
_chemical_formula_weight         636.85
_chemical_name_systematic
;
4,4'-Thiodiphenol-1,4,8,11-tetraazacyclotetradecane (2/1)
;
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 103.127(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.1602(12)
_cell_length_b                   10.8084(12)
_cell_length_c                   14.001(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294.0(10)
_cell_measurement_theta_max      17.89
_cell_measurement_theta_min      10.31
_cell_volume                     1644.7(4)
_computing_cell_refinement       'SET4 and CELDIM (Enraf-Nonius, 1992)'
_computing_data_collection       'CAD4 (Enraf-Nonius, 1992)'
_computing_data_reduction        'DATRD2 in NRCVAX96 (Gabe et al., 1989)'
_computing_molecular_graphics
'NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1996a), PLUTON (Spek 1996b)'
_computing_publication_material
'NRCVAX96, SHELXL93  and WordPerfect macro PRPCIF97 (Ferguson, 1997)'
_computing_structure_refinement  'NRCVAX96 and SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SOLVER in NRCVAX96'
_diffrn_ambient_temperature      294.0(10)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.006
_diffrn_reflns_av_sigmaI/netI    0.0645
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4130
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         2.40
_diffrn_standards_decay_%        'no decay, variation 0.5'
_diffrn_standards_interval_time  720
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_type   'Gaussian (north et al., 1968)'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.192
_refine_ls_extinction_coef       0.0013(9)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   0.964
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.964
_refine_ls_restrained_S_obs      1.192
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          -0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;calc w = 1/[\s^2^(Fo^2^) + (0.0550P)^2^], where P = (Fo^2^ +
2Fc^2^)/3
;
_refine_ls_wR_factor_all         0.1160
_refine_ls_wR_factor_ref         0.1029
_reflns_number_gt                2023
_reflns_number_total             3747
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ab0380.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1644.7(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2105511
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_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_type_symbol
S1 0.55042(5) 0.18244(6) -0.41081(5) 0.0574(2) Uani d . 1 S
O1 0.19678(12) 0.05855(15) -0.16811(10) 0.0549(4) Uani d . 1 O
O2 1.01827(15) -0.0778(2) -0.24402(13) 0.0559(4) Uani d . 1 O
C11 0.4520(2) 0.1362(2) -0.3339(2) 0.0421(5) Uani d . 1 C
C12 0.4569(2) 0.1952(2) -0.2456(2) 0.0488(6) Uani d . 1 C
C13 0.3752(2) 0.1658(2) -0.1884(2) 0.0483(6) Uani d . 1 C
C14 0.2813(2) 0.0799(2) -0.21933(15) 0.0415(5) Uani d . 1 C
C15 0.2794(2) 0.0186(2) -0.3075(2) 0.0484(6) Uani d . 1 C
C16 0.3636(2) 0.0455(2) -0.3634(2) 0.0477(5) Uani d . 1 C
C21 0.6911(2) 0.1050(2) -0.35868(14) 0.0424(5) Uani d . 1 C
C22 0.6989(2) -0.0224(2) -0.3606(2) 0.0482(6) Uani d . 1 C
C23 0.8087(2) -0.0823(2) -0.3220(2) 0.0482(5) Uani d . 1 C
C24 0.9141(2) -0.0143(2) -0.28236(15) 0.0417(5) Uani d . 1 C
C25 0.9069(2) 0.1138(2) -0.28223(15) 0.0438(5) Uani d . 1 C
C26 0.7960(2) 0.1725(2) -0.31893(14) 0.0431(5) Uani d . 1 C
N31 0.1724(2) 0.0845(2) 0.01429(14) 0.0610(6) Uani d . 1 N
C32 0.1420(3) 0.2076(3) 0.0489(2) 0.0863(10) Uani d . 1 C
C33 0.0174(3) 0.2486(3) -0.0061(2) 0.0882(10) Uani d . 1 C
N34 -0.0765(2) 0.1606(2) 0.00709(14) 0.0628(6) Uani d . 1 N
C35 -0.2000(3) 0.1943(3) -0.0494(2) 0.0921(11) Uani d . 1 C
C36 -0.2979(3) 0.1025(4) -0.0365(2) 0.0983(12) Uani d . 1 C
C37 -0.2829(2) -0.0238(4) -0.0755(2) 0.0956(11) Uani d . 1 C
H2 1.0751 -0.0285 -0.2232 0.087(10) Uiso d . 1 H
H12 0.5162 0.2557 -0.2243 0.059 Uiso calc R 1 H
H13 0.3830 0.2041 -0.1278 0.058 Uiso calc R 1 H
H15 0.2201 -0.0418 -0.3292 0.058 Uiso calc R 1 H
H16 0.3608 0.0023 -0.4213 0.057 Uiso calc R 1 H
H22 0.6293 -0.0686 -0.3882 0.058 Uiso calc R 1 H
H23 0.8121 -0.1682 -0.3226 0.058 Uiso calc R 1 H
H25 0.9771 0.1604 -0.25731 0.053 Uiso calc R 1 H
H26 0.7918 0.2584 -0.31690 0.052 Uiso calc R 1 H
H31A 0.1837 0.0927 -0.04703 0.073 Uiso calc R 1 H
H31E 0.1074 0.0342 0.01121 0.073 Uiso calc PR 0.81(3) H
H32A 0.2032 0.2674 0.0396 0.104 Uiso calc R 1 H
H32B 0.1438 0.2036 0.1184 0.104 Uiso calc R 1 H
H33A -0.0007 0.3294 0.0173 0.106 Uiso calc R 1 H
H33B 0.0166 0.2557 -0.0753 0.106 Uiso calc R 1 H
H34A -0.0773 0.1567 0.07115 0.075 Uiso calc R 1 H
H34E -0.0570 0.0850 -0.01167 0.075 Uiso calc PR 0.19(3) H
H35A -0.1989 0.1991 -0.1184 0.111 Uiso calc R 1 H
H35B -0.2212 0.2755 -0.0289 0.111 Uiso calc R 1 H
H36A -0.2967 0.0959 0.0328 0.118 Uiso calc R 1 H
H36B -0.3779 0.1345 -0.0694 0.118 Uiso calc R 1 H
H37A -0.3553 -0.0732 -0.0749 0.115 Uiso calc R 1 H
H37B -0.2742 -0.0178 -0.1427 0.115 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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-3 -3 -3
-3 3 -3
-4 3 0
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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
S1 C11 C12 . . 120.6(2) yes
S1 C11 C16 . . 121.0(2) yes
C11 S1 C21 . . 103.21(9) yes
C11 C12 C13 . . 121.0(2) yes
C11 C16 C15 . . 120.6(2) yes
C12 C11 C16 . . 118.3(2) yes
C12 C13 C14 . . 121.5(2) yes
C13 C14 C15 . . 116.8(2) yes
C14 C15 C16 . . 121.6(2) yes
O1 C14 C13 . . 121.6(2) yes
O1 C14 C15 . . 121.6(2) yes
S1 C21 C22 . . 120.9(2) yes
S1 C21 C26 . . 120.1(2) yes
C21 C22 C23 . . 120.9(2) yes
C21 C26 C25 . . 120.7(2) yes
C22 C21 C26 . . 118.9(2) yes
C22 C23 C24 . . 120.2(2) yes
C23 C24 C25 . . 118.9(2) yes
C24 C25 C26 . . 120.4(2) yes
O2 C24 C23 . . 117.6(2) yes
O2 C24 C25 . . 123.5(2) yes
N31 C32 C33 . . 110.7(2) yes
N31 C37 C36 3 . 109.9(2) yes
C32 N31 C37 . 3 115.5(2) yes
N34 C33 C32 . . 110.7(2) yes
N34 C35 C36 . . 112.7(2) yes
C33 N34 C35 . . 112.5(2) yes
C35 C36 C37 . . 114.2(2) yes
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 C11 . 1.776(2) yes
S1 C21 . 1.783(2) yes
O1 C14 . 1.328(2) yes
O2 C24 . 1.352(2) yes
C11 C12 . 1.381(3) yes
C11 C16 . 1.386(3) yes
C12 C13 . 1.381(3) yes
C13 C14 . 1.393(3) yes
C14 C15 . 1.397(3) yes
C15 C16 . 1.383(3) yes
C21 C22 . 1.380(3) yes
C21 C26 . 1.385(3) yes
C22 C23 . 1.382(3) yes
C23 C24 . 1.392(3) yes
C24 C25 . 1.386(3) yes
C25 C26 . 1.382(3) yes
N31 C32 . 1.481(3) yes
N31 C37 3 1.484(3) yes
C32 C33 . 1.496(4) yes
C33 N34 . 1.458(3) yes
N34 C35 . 1.471(3) yes
C35 C36 . 1.516(4) yes
C36 C37 . 1.494(4) yes
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
O2 H2 O1 1_655 0.83 1.69 2.512(2) 172 yes
N31 H31A O1 . 0.90 1.77 2.644(2) 162 yes
N31 H31E N34 . 0.90 2.46 2.877(3) 109 yes
N31 H31E N34 3_555 0.90 2.14 2.847(3) 135 yes
N34 H34A O2 3_655 0.90 2.51 3.354(3) 157 yes
C36 H36A O1 3_555 0.97 2.58 3.323(4) 133 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C21 S1 C11 C12 . . 81.9(2) yes
C21 S1 C11 C16 . . -102.0(2) yes
C16 C11 C12 C13 . . -0.7(3) yes
S1 C11 C12 C13 . . 175.5(2) yes
C11 C12 C13 C14 . . -3.0(3) yes
C12 C13 C14 O1 . . -174.6(2) yes
C12 C13 C14 C15 . . 4.5(3) yes
O1 C14 C15 C16 . . 176.6(2) yes
C13 C14 C15 C16 . . -2.6(3) yes
C14 C15 C16 C11 . . -0.9(3) yes
C12 C11 C16 C15 . . 2.6(3) yes
S1 C11 C16 C15 . . -173.6(2) yes
C11 S1 C21 C22 . . 66.3(2) yes
C11 S1 C21 C26 . . -116.3(2) yes
C26 C21 C22 C23 . . 1.2(3) yes
S1 C21 C22 C23 . . 178.6(2) yes
C21 C22 C23 C24 . . -1.4(3) yes
C22 C23 C24 O2 . . 178.8(2) yes
C22 C23 C24 C25 . . 0.1(3) yes
O2 C24 C25 C26 . . -177.2(2) yes
C23 C24 C25 C26 . . 1.4(3) yes
C24 C25 C26 C21 . . -1.7(3) yes
C22 C21 C26 C25 . . 0.4(3) yes
S1 C21 C26 C25 . . -177.12(15) yes
C37 N31 C32 C33 3 . -169.0(2) yes
N31 C32 C33 N34 . . 59.5(3) yes
C32 C33 N34 C35 . . -177.4(2) yes
C33 N34 C35 C36 . . 179.6(2) yes
N34 C35 C36 C37 . . -64.8(3) yes
C35 C36 C37 N31 . 3 68.9(3) yes
