#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/18/2101840.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_2101840
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         '(C6 H6 O3) . 1.5(C6 H12 N4)'
_chemical_formula_sum            'C15 H24 N6 O3'
_chemical_formula_weight         336.40
_chemical_name_systematic        ?
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 96.822(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.598(2)
_cell_length_b                   7.136(2)
_cell_length_c                   19.445(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294.0(10)
_cell_measurement_theta_max      18.01
_cell_measurement_theta_min      10.44
_cell_volume                     3251.3(11)
_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  0.019
_diffrn_reflns_av_sigmaI/netI    0.1110
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3619
_diffrn_reflns_theta_max         27
_diffrn_reflns_theta_min         2
_diffrn_standards_decay_%        2.2
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  1.0
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.923
_refine_ls_goodness_of_fit_obs   1.198
_refine_ls_hydrogen_treatment    'riding (C-H 0.93 to 0.97, O-H 0.82\%A)'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.923
_refine_ls_restrained_S_obs      1.198
_refine_ls_R_factor_all          0.1774
_refine_ls_R_factor_obs          0.0628
_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)+(0.0478P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1392
_refine_ls_wR_factor_obs         0.1138
_reflns_number_observed          1516
_reflns_number_total             3521
_reflns_observed_criterion       >2\s(I)
_cod_data_source_file            ab0361.cif
_cod_data_source_block           6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0478P)^2^] 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^)+(0.0478P)^2^]
where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        3251.2(11)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2101840
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 0.08055(9) -0.0337(3) 0.51823(13) 0.0664(8) Uani d . 1 O
O3 0.21032(8) 0.3343(3) 0.40077(13) 0.0531(7) Uani d . 1 O
O5 0.01941(8) 0.5283(3) 0.41161(12) 0.0568(7) Uani d . 1 O
C1 0.09416(12) 0.1180(4) 0.48081(14) 0.0385(8) Uani d . 1 C
C2 0.14745(12) 0.1411(4) 0.45930(14) 0.0369(7) Uani d . 1 C
C3 0.15785(12) 0.2978(4) 0.42123(14) 0.0344(7) Uani d . 1 C
C4 0.11563(12) 0.4286(4) 0.40377(14) 0.0361(7) Uani d . 1 C
C5 0.06260(12) 0.4041(4) 0.42639(14) 0.0340(7) Uani d . 1 C
C6 0.05156(12) 0.2481(4) 0.46468(14) 0.0391(8) Uani d . 1 C
N11 0.15670(10) -0.2708(3) 0.59019(12) 0.0390(6) Uani d . 1 N
C12 0.19623(12) -0.4015(5) 0.56327(14) 0.0457(8) Uani d . 1 C
N13 0.22300(10) -0.5286(3) 0.61708(12) 0.0385(6) Uani d . 1 N
C14 0.17706(12) -0.6313(4) 0.6464(2) 0.0436(8) Uani d . 1 C
N15 0.13696(10) -0.5070(3) 0.67538(12) 0.0390(6) Uani d . 1 N
C16 0.11240(12) -0.3817(4) 0.6199(2) 0.0447(8) Uani d . 1 C
C17 0.18796(14) -0.1633(4) 0.6470(2) 0.0522(9) Uani d . 1 C
C18 0.25283(12) -0.4129(5) 0.6731(2) 0.0518(9) Uani d . 1 C
C19 0.16913(14) -0.3929(5) 0.7291(2) 0.0529(9) Uani d . 1 C
N10 0.21466(11) -0.2838(4) 0.70277(13) 0.0473(7) Uani d . 1 N
N21 0.02194(10) 0.7951(3) 0.31046(12) 0.0390(6) Uani d . 1 N
C22 -0.02502(13) 0.9154(5) 0.32753(15) 0.0469(9) Uani d . 1 C
N23 -0.04728(11) 1.0347(4) 0.26962(13) 0.0508(8) Uani d . 1 N
C24 0.0000 1.1475(7) 0.2500 0.064(2) Uani d S 1 C
C25 0.0000 0.6807(6) 0.2500 0.0438(12) Uani d S 1 C
C26 -0.06744(13) 0.9155(5) 0.2106(2) 0.0532(9) Uani d . 1 C
H1 0.1094 -0.0949 0.5302 0.100 Uiso calc R 1 H
H3 0.2292 0.2375 0.4025 0.080 Uiso calc R 1 H
H5 0.0298 0.6128 0.3874 0.085 Uiso calc R 1 H
H2 0.17590 0.0522 0.47032 0.044 Uiso calc R 1 H
H4 0.12265 0.5323 0.37708 0.043 Uiso calc R 1 H
H6 0.01582 0.2311 0.47937 0.047 Uiso calc R 1 H
H12A 0.22574 -0.3313 0.54385 0.055 Uiso calc R 1 H
H12B 0.17581 -0.4749 0.52630 0.055 Uiso calc R 1 H
H14A 0.15644 -0.7072 0.6103 0.052 Uiso calc R 1 H
H14B 0.19398 -0.7151 0.6824 0.052 Uiso calc R 1 H
H16A 0.08568 -0.2970 0.6381 0.054 Uiso calc R 1 H
H16B 0.09142 -0.4556 0.5835 0.054 Uiso calc R 1 H
H17A 0.21726 -0.0891 0.6289 0.063 Uiso calc R 1 H
H17B 0.16182 -0.0778 0.6658 0.063 Uiso calc R 1 H
H18A 0.27058 -0.4946 0.7094 0.062 Uiso calc R 1 H
H18B 0.28283 -0.3421 0.6550 0.062 Uiso calc R 1 H
H19A 0.18580 -0.4742 0.7660 0.063 Uiso calc R 1 H
H19B 0.14313 -0.3079 0.7484 0.063 Uiso calc R 1 H
H22A -0.05560 0.8373 0.34069 0.056 Uiso calc R 1 H
H22B -0.01153 0.9935 0.36692 0.056 Uiso calc R 1 H
H24A -0.0141 1.2277 0.2114 0.076 Uiso calc PR 0.50 H
H24B 0.0141 1.2276 0.2886 0.076 Uiso calc PR 0.50 H
H25A 0.0304 0.6006 0.2375 0.053 Uiso calc PR 0.50 H
H25B -0.0304 0.6006 0.2625 0.053 Uiso calc PR 0.50 H
H26A -0.08226 0.9939 0.1718(2) 0.064 Uiso calc R 1 H
H26B -0.09842 0.8375 0.2227 0.064 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'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
8 -2 -4
-4 -2 -7
2 -2 -5
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
O1 C1 C6 . . 116.4(3)
O1 C1 C2 . . 122.5(3)
C2 C1 C6 . . 121.1(3)
C1 C2 C3 . . 119.0(3)
O3 C3 C4 . . 116.9(3)
O3 C3 C2 . . 122.3(3)
C2 C3 C4 . . 120.8(3)
C3 C4 C5 . . 119.3(3)
O5 C5 C6 . . 117.1(2)
O5 C5 C4 . . 122.3(3)
C4 C5 C6 . . 120.5(3)
C1 C6 C5 . . 119.1(3)
C12 N11 C17 . . 108.5(2)
C12 N11 C16 . . 108.0(2)
C16 N11 C17 . . 107.5(2)
N11 C12 N13 . . 112.2(2)
C12 N13 C18 . . 107.9(2)
C12 N13 C14 . . 107.9(2)
C14 N13 C18 . . 107.4(2)
N15 C14 N13 . . 112.8(2)
C14 N15 C19 . . 108.0(2)
C14 N15 C16 . . 107.7(2)
C16 N15 C19 . . 108.2(2)
N15 C16 N11 . . 112.2(2)
N10 C17 N11 . . 112.6(2)
N10 C18 N13 . . 112.5(2)
N10 C19 N15 . . 112.7(2)
C18 N10 C17 . . 108.1(2)
C18 N10 C19 . . 108.4(2)
C17 N10 C19 . . 107.5(2)
C22 N21 C26 . 2 108.5(2)
C22 N21 C25 . . 107.5(2)
C25 N21 C26 . 2 107.5(2)
N21 C22 N23 . . 112.2(2)
C22 N23 C26 . . 108.7(3)
C22 N23 C24 . . 107.9(2)
C24 N23 C26 . . 107.6(2)
N23 C24 N23 2 . 113.2(4)
N21 C25 N21 2 . 112.7(3)
N21 C26 N23 2 . 112.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.364(3)
O3 C3 . 1.370(3)
O5 C5 . 1.355(3)
C1 C2 . 1.382(4)
C1 C6 . 1.377(4)
C2 C3 . 1.379(4)
C3 C4 . 1.378(4)
C4 C5 . 1.386(4)
C5 C6 . 1.381(4)
N11 C12 . 1.460(3)
N11 C16 . 1.482(3)
N11 C17 . 1.470(4)
C12 N13 . 1.470(4)
N13 C14 . 1.478(3)
N13 C18 . 1.477(4)
C14 N15 . 1.459(3)
N15 C16 . 1.467(4)
N15 C19 . 1.463(4)
C17 N10 . 1.466(4)
C18 N10 . 1.455(4)
C19 N10 . 1.467(4)
N21 C22 . 1.470(3)
N21 C26 2 1.471(4)
N21 C25 . 1.474(3)
C22 N23 . 1.459(4)
N23 C24 . 1.463(4)
N23 C26 . 1.462(4)
C24 N23 2 1.463(3)
C25 N21 2 1.474(3)
C26 N21 2 1.471(4)
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
O1 C1 C2 C3 . . 179.6(3)
C6 C1 C2 C3 . . 0.2(4)
C1 C2 C3 O3 . . 177.0(3)
C1 C2 C3 C4 . . -1.0(4)
O3 C3 C4 C5 . . -176.5(3)
C2 C3 C4 C5 . . 1.7(4)
C3 C4 C5 O5 . . 179.4(3)
C3 C4 C5 C6 . . -1.5(4)
O1 C1 C6 C5 . . -179.5(3)
C2 C1 C6 C5 . . -0.1(5)
O5 C5 C6 C1 . . 179.9(3)
C4 C5 C6 C1 . . 0.7(4)
C17 N11 C12 N13 . . 57.7(3)
C16 N11 C12 N13 . . -58.5(3)
N11 C12 N13 C18 . . -57.8(3)
N11 C12 N13 C14 . . 58.0(3)
C12 N13 C14 N15 . . -58.2(3)
C18 N13 C14 N15 . . 57.9(3)
N13 C14 N15 C19 . . -58.2(3)
N13 C14 N15 C16 . . 58.4(3)
C14 N15 C16 N11 . . -58.5(3)
C19 N15 C16 N11 . . 57.9(3)
C12 N11 C16 N15 . . 58.9(3)
C17 N11 C16 N15 . . -58.0(3)
C12 N11 C17 N10 . . -57.7(3)
C16 N11 C17 N10 . . 58.9(3)
C12 N13 C18 N10 . . 58.4(3)
C14 N13 C18 N10 . . -57.7(3)
C14 N15 C19 N10 . . 57.9(3)
C16 N15 C19 N10 . . -58.4(3)
N13 C18 N10 C17 . . -58.2(3)
N13 C18 N10 C19 . . 58.0(3)
N11 C17 N10 C18 . . 57.8(3)
N11 C17 N10 C19 . . -59.1(3)
N15 C19 N10 C18 . . -58.0(3)
N15 C19 N10 C17 . . 58.6(3)
C26 N21 C22 N23 2 . 57.8(3)
C25 N21 C22 N23 . . -58.1(3)
N21 C22 N23 C26 . . 58.8(3)
N21 C22 N23 C24 . . -57.6(3)
C22 N23 C24 N23 . 2 58.5(2)
C26 N23 C24 N23 . 2 -58.5(2)
C22 N21 C25 N21 . 2 58.3(2)
C26 N21 C25 N21 2 2 -58.3(2)
C22 N23 C26 N21 . 2 -58.8(3)
C24 N23 C26 N21 . 2 57.8(3)
