#------------------------------------------------------------------------------
#$Date: 2016-02-20 01:53:41 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/18/2101836.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_2101836
loop_
_publ_author_name
'Ferguson, George'
_publ_section_title
;
 Crystal Engineering Using Bisphenols and Trisphenols. Complexes with
 Hexamethylenetetramine (HMTA): Strings, Multiple Helices and
 Chains-of-Rings in the Crystal Structures of the Adducts of HTMA with
 4,4'-Thiodiphenol (1/1), 4,4'-Sulfonyldiphenol (1/1),
 4,4'-Isopropylidenediphenol (1/1), 1,1,1-Tris(4-hydroxyphenyl)ethane
 (1/2) and 1,3,5-Trihydroxybenzene (2/3)
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              521
_journal_page_last               533
_journal_paper_doi               10.1107/S0108768196014048
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C12 H10 O2 S, C6 H12 N4 '
_chemical_formula_sum            'C18 H22 N4 O2 S'
_chemical_formula_weight         358.46
_chemical_name_systematic        ?
_space_group_IT_number           31
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac -2'
_symmetry_space_group_name_H-M   'P m n 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.029(2)
_cell_length_b                   9.7954(8)
_cell_length_c                   5.9817(11)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294.0(10)
_cell_measurement_theta_max      21.60
_cell_measurement_theta_min      8.95
_cell_volume                     880.6(2)
_computing_cell_refinement       'SET4 and CELDIM (Enraf-Nonius, 1992)'
_computing_data_collection       'CAD4 (Enraf-Nonius, 1992)'
_computing_data_reduction
'DATRD2 in NRCVAX94 (Gabe, Le Page, Charland, Lee & White, 1989)'
_computing_molecular_graphics
'NRCVAX94, PLATON (Spek, 1995a) and PLUTON (Spek 1995b)'
_computing_publication_material
'NRCVAX94, SHELXL93  and WordPerfect macro PREPCIF'
_computing_structure_refinement  'NRCVAX94 and SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1986)'
_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           'Molybdenum K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1096
_diffrn_reflns_theta_max         26.91
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        '2.7, allowed for by scaling'
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.170
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.29(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.100
_refine_ls_goodness_of_fit_obs   1.234
_refine_ls_hydrogen_treatment
'riding (SHELXL defaults, C-H 0.93 to 0.97, O-H 0.82\%A)'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1096
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.099
_refine_ls_restrained_S_obs      1.233
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_obs          0.0323
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0420P)²+0.0837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0863
_refine_ls_wR_factor_obs         0.0819
_reflns_number_observed          818
_reflns_number_total             1096
_reflns_observed_criterion       >2\s(I)
_cod_data_source_file            ab0361.cif
_cod_data_source_block           4c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+0.0837P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+0.0837P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2101836
_cod_database_fobs_code          2101836
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, z'
'x+1/2, -y, z+1/2'
'-x+1/2, -y, z+1/2'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0410(5) 0.0341(5) 0.0562(8) 0.000 0.000 0.0124(6)
O1 0.0497(13) 0.091(2) 0.0471(14) 0.0299(12) -0.0027(13) -0.008(2)
C11 0.0299(12) 0.0311(13) 0.040(2) -0.0064(11) 0.0022(12) 0.0051(13)
C12 0.0374(14) 0.0439(15) 0.032(2) -0.0056(12) 0.0030(13) -0.0045(13)
C13 0.0373(14) 0.0455(14) 0.037(2) 0.0018(12) 0.004(2) -0.004(2)
C14 0.0276(13) 0.0460(15) 0.042(2) 0.0031(13) 0.0036(13) 0.000(2)
C15 0.0355(14) 0.052(2) 0.033(2) -0.0035(14) 0.0004(14) -0.0057(14)
C16 0.0351(14) 0.038(2) 0.039(2) -0.0011(12) 0.0066(15) -0.0079(14)
N1 0.0355(12) 0.0388(12) 0.0377(14) 0.0025(9) 0.0003(12) -0.0043(12)
C2 0.046(2) 0.055(2) 0.042(2) 0.0066(14) -0.012(2) 0.001(2)
N3 0.048(2) 0.057(2) 0.027(2) 0.000 0.000 -0.006(2)
C4 0.051(3) 0.042(3) 0.053(3) 0.000 0.000 -0.017(2)
N5 0.054(2) 0.031(2) 0.040(2) 0.000 0.000 0.003(2)
C6 0.040(2) 0.048(2) 0.043(2) -0.0100(14) 0.0081(15) 0.000(2)
C7 0.046(2) 0.035(2) 0.044(3) 0.000 0.000 -0.011(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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
S1 0.0000 0.55486(10) 0.0000(2) 0.0438(3) Uani d S 1 S
O1 0.30569(14) 0.2224(3) 0.3064(4) 0.0625(7) Uani d . 1 O
C11 0.0914(2) 0.4535(3) 0.0913(5) 0.0338(6) Uani d . 1 C
C12 0.1296(2) 0.3595(3) -0.0521(5) 0.0376(7) Uani d . 1 C
C13 0.2020(2) 0.2821(3) 0.0150(6) 0.0400(7) Uani d . 1 C
C14 0.2364(2) 0.2978(3) 0.2270(5) 0.0387(7) Uani d . 1 C
C15 0.1990(2) 0.3915(3) 0.3717(5) 0.0402(7) Uani d . 1 C
C16 0.1270(2) 0.4684(3) 0.3052(5) 0.0376(7) Uani d . 1 C
N1 0.41862(14) 0.0862(2) 0.0276(5) 0.0374(6) Uani d . 1 N
C2 0.4208(2) 0.0782(3) -0.2193(6) 0.0479(8) Uani d . 1 C
N3 0.5000 0.0065(4) -0.2996(6) 0.0442(9) Uani d S 1 N
C4 0.5000 -0.1320(4) -0.2015(9) 0.0487(12) Uani d S 1 C
N5 0.5000 -0.1285(3) 0.0415(7) 0.0417(9) Uani d S 1 N
C6 0.4215(2) -0.0554(3) 0.1160(5) 0.0436(8) Uani d . 1 C
C7 0.5000 0.1557(4) 0.1022(8) 0.0419(10) Uani d S 1 C
H1 0.3308 0.1844 0.2019 0.094 Uiso calc R 1 H
H12 0.1065 0.3482 -0.1951 0.045 Uiso calc R 1 H
H13 0.2273 0.2195 -0.0831 0.048 Uiso calc R 1 H
H15 0.2224 0.4027 0.5144 0.048 Uiso calc R 1 H
H16 0.1019 0.5309 0.4038 0.045 Uiso calc R 1 H
H2A 0.3680 0.0310 -0.2717 0.057 Uiso calc R 1 H
H2B 0.4200 0.1698 -0.2808 0.057 Uiso calc R 1 H
H4A 0.4478 -0.1810 -0.2530 0.058 Uiso calc PR 0.50 H
H4B 0.5522 -0.1810 -0.2530(9) 0.058 Uiso calc PR 0.50 H
H6A 0.4209 -0.0525 0.2781 0.052 Uiso calc R 1 H
H6B 0.3688 -0.1041 0.0672 0.052 Uiso calc R 1 H
H7A 0.5000 0.1607 0.2642 0.050 Uiso calc SR 1 H
H7B 0.5000 0.2484 0.0450(8) 0.050 Uiso calc SR 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
4 3 -1
-4 3 1
0 4 -1
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
C11 S1 C11 . 2 101.0(2)
C12 C11 C16 . . 118.6(3)
C12 C11 S1 . . 120.1(2)
C16 C11 S1 . . 121.3(2)
C11 C12 C13 . . 120.7(3)
C14 C13 C12 . . 120.0(3)
O1 C14 C13 . . 123.2(3)
O1 C14 C15 . . 117.0(3)
C13 C14 C15 . . 119.8(3)
C16 C15 C14 . . 120.2(3)
C15 C16 C11 . . 120.6(3)
C7 N1 C2 . . 108.0(3)
C7 N1 C6 . . 107.5(3)
C2 N1 C6 . . 107.8(2)
N3 C2 N1 . . 111.8(3)
C2 N3 C2 2_655 . 108.8(3)
C2 N3 C4 . . 108.1(2)
C2 N3 C4 2_655 . 108.1(2)
N5 C4 N3 . . 112.1(4)
C6 N5 C6 2_655 . 108.9(3)
C6 N5 C4 . . 108.6(2)
C6 N5 C4 2_655 . 108.6(2)
N5 C6 N1 . . 112.1(3)
N1 C7 N1 . 2_655 112.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C11 1.781(3)
O1 C14 1.362(3)
C11 C12 1.383(4)
C11 C16 1.395(4)
C12 C13 1.385(4)
C13 C14 1.379(4)
C14 C15 1.382(4)
C15 C16 1.377(4)
N1 C2 1.479(4)
N1 C6 1.485(4)
N1 C7 1.469(3)
C2 N3 1.464(4)
N3 C4 1.477(5)
C4 N5 1.454(6)
N5 C6 1.450(3)
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
C11 S1 C11 C12 2 . 93.0(2)
C11 S1 C11 C16 2 . -88.3(2)
C16 C11 C12 C13 . . -0.2(4)
S1 C11 C12 C13 . . 178.6(2)
C11 C12 C13 C14 . . 0.3(4)
C12 C13 C14 O1 . . 178.0(3)
C12 C13 C14 C15 . . -0.4(4)
O1 C14 C15 C16 . . -178.1(2)
C13 C14 C15 C16 . . 0.5(4)
C14 C15 C16 C11 . . -0.4(4)
C12 C11 C16 C15 . . 0.3(4)
S1 C11 C16 C15 . . -178.5(2)
C7 N1 C2 N3 . . 57.9(3)
C6 N1 C2 N3 . . -58.0(3)
N1 C2 N3 C2 . 2_655 -58.8(4)
N1 C2 N3 C4 . . 58.4(4)
C2 N3 C4 N5 2_655 . 58.8(2)
C2 N3 C4 N5 . . -58.8(2)
N3 C4 N5 C6 . 2_655 -59.1(2)
N3 C4 N5 C6 . . 59.1(2)
C6 N5 C6 N1 2_655 . 59.2(4)
C4 N5 C6 N1 . . -58.9(4)
C7 N1 C6 N5 . . -58.1(3)
C2 N1 C6 N5 . . 58.2(3)
C2 N1 C7 N1 . 2_655 -58.0(4)
C6 N1 C7 N1 . 2_655 58.1(4)
