#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/25/2222537.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_2222537
loop_
_publ_author_name
'Li, Yu-Feng'
'Jian, Fang-Fang'
_publ_section_title
;
 2,2'-[(Biphenyl-4,4'-diyl)di(ethene-1,2-diyl)]dibenzenesulfonic
 acid--4-methylpiperidine--water (1/2/2)
;
_journal_coeditor_code           AT2832
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1931
_journal_paper_doi               10.1107/S1600536809026932
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C28 H22 O6 S2, 2(C6 H13 N1), 2(H2 O1)'
_chemical_formula_moiety         'C28 H22 O6 S2, 2C6 H13 N1, 2H2 O1'
_chemical_formula_sum            'C40 H52 N2 O8 S2'
_chemical_formula_weight         752.96
_chemical_name_systematic
;
2,2'-[(Biphenyl-4,4'-diyl)di(ethene-1,2-diyl)]dibenzenesulfonic
acid--4-methylpiperidine--water (1/2/2)
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.76(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.852(3)
_cell_length_b                   9.7240(19)
_cell_length_c                   14.765(3)
_cell_measurement_temperature    293(2)
_cell_volume                     2006.8(8)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0881
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4436
_diffrn_reflns_theta_full        26.97
_diffrn_reflns_theta_max         26.97
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.266
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4264
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1814
_refine_ls_R_factor_gt           0.0599
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0935P)²+0.2207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.2036
_reflns_number_gt                1779
_reflns_number_total             4264
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2832.cif
_cod_data_source_block           I
_cod_original_cell_volume        2006.8(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222537
_cod_database_fobs_code          2222537
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.16287(7) 0.72108(11) 0.45278(7) 0.0650(4) Uani d . 1 . .
O O1 0.11710(19) 0.6177(3) 0.49284(19) 0.0777(8) Uani d . 1 . .
O O2 0.2213(2) 0.8160(3) 0.5239(2) 0.0963(10) Uani d . 1 . .
H H2A 0.1872 0.8610 0.5464 0.144 Uiso calc R 1 . .
O O3 0.0962(2) 0.7896(3) 0.3708(2) 0.0946(10) Uani d . 1 . .
C C1 0.2421(2) 0.6277(4) 0.4076(2) 0.0547(9) Uani d . 1 . .
C C2 0.2274(3) 0.6354(4) 0.3096(3) 0.0685(11) Uani d . 1 . .
H H2B 0.1789 0.6909 0.2704 0.082 Uiso calc R 1 . .
C C3 0.2841(3) 0.5616(5) 0.2699(3) 0.0813(13) Uani d . 1 . .
H H3B 0.2744 0.5689 0.2045 0.098 Uiso calc R 1 . .
C C4 0.3556(3) 0.4763(5) 0.3275(3) 0.0797(13) Uani d . 1 . .
H H4A 0.3918 0.4229 0.3004 0.096 Uiso calc R 1 . .
C C5 0.3726(3) 0.4712(4) 0.4253(3) 0.0673(11) Uani d . 1 . .
H H5A 0.4222 0.4164 0.4637 0.081 Uiso calc R 1 . .
C C6 0.3174(2) 0.5464(4) 0.4686(2) 0.0549(9) Uani d . 1 . .
C C7 0.3396(2) 0.5464(4) 0.5737(2) 0.0572(10) Uani d . 1 . .
H H7A 0.3073 0.6108 0.5979 0.069 Uiso calc R 1 . .
C C8 0.4005(2) 0.4653(4) 0.6378(3) 0.0593(10) Uani d . 1 . .
H H8A 0.4296 0.3958 0.6143 0.071 Uiso calc R 1 . .
C C9 0.4261(2) 0.4755(4) 0.7428(2) 0.0527(9) Uani d . 1 . .
C C10 0.4910(3) 0.3842(5) 0.8026(3) 0.0808(13) Uani d . 1 . .
H H10A 0.5164 0.3147 0.7752 0.097 Uiso calc R 1 . .
C C11 0.5191(3) 0.3931(5) 0.9011(3) 0.0785(13) Uani d . 1 . .
H H11A 0.5627 0.3292 0.9382 0.094 Uiso calc R 1 . .
C C12 0.4847(2) 0.4936(4) 0.9467(2) 0.0502(9) Uani d . 1 . .
C C13 0.4184(3) 0.5858(4) 0.8868(3) 0.0680(11) Uani d . 1 . .
H H13A 0.3927 0.6548 0.9142 0.082 Uiso calc R 1 . .
C C14 0.3906(3) 0.5760(4) 0.7881(3) 0.0679(11) Uani d . 1 . .
H H14A 0.3466 0.6390 0.7506 0.081 Uiso calc R 1 . .
C C17 0.1822(5) 0.2643(6) 0.1068(3) 0.131(2) Uani d . 1 . .
H H17A 0.1298 0.2262 0.1227 0.196 Uiso calc R 1 . .
H H17B 0.1970 0.3543 0.1346 0.196 Uiso calc R 1 . .
H H17C 0.2372 0.2060 0.1317 0.196 Uiso calc R 1 . .
C C15 0.0653(3) 0.3594(5) -0.0460(4) 0.0913(15) Uani d . 1 . .
H H15A 0.0749 0.4489 -0.0152 0.110 Uiso calc R 1 . .
H H15B 0.0127 0.3150 -0.0327 0.110 Uiso calc R 1 . .
C C16 0.0386(3) 0.3788(6) -0.1540(4) 0.0992(16) Uani d . 1 . .
H H16A 0.0216 0.2909 -0.1863 0.119 Uiso calc R 1 . .
H H16B -0.0163 0.4394 -0.1773 0.119 Uiso calc R 1 . .
N N2 0.1191(3) 0.4378(4) -0.1755(2) 0.0859(11) Uani d . 1 . .
H H2C 0.1167 0.5144 -0.2053 0.103 Uiso calc R 1 . .
C C18 0.2061(4) 0.3503(5) -0.1398(3) 0.0917(14) Uani d . 1 . .
H H18A 0.2582 0.3927 -0.1554 0.110 Uiso calc R 1 . .
H H18B 0.1935 0.2609 -0.1706 0.110 Uiso calc R 1 . .
C C19 0.2335(3) 0.3339(5) -0.0337(3) 0.0815(13) Uani d . 1 . .
H H19A 0.2516 0.4229 -0.0033 0.098 Uiso calc R 1 . .
H H19B 0.2890 0.2741 -0.0111 0.098 Uiso calc R 1 . .
C C20 0.1544(3) 0.2747(4) -0.0032(3) 0.0777(12) Uani d . 1 . .
H H20A 0.1410 0.1815 -0.0297 0.093 Uiso calc R 1 . .
O O1W -0.0458(3) 0.4739(4) 0.3645(2) 0.0939(11) Uani d . 1 . .
H H2 -0.082(3) 0.537(4) 0.380(3) 0.074(16) Uiso d D 1 . .
H H1 0.009(3) 0.512(7) 0.410(4) 0.17(3) Uiso d D 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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 S1 O2 . . 112.82(19) ?
O3 S1 O1 . . 112.34(19) ?
O2 S1 O1 . . 113.35(19) ?
O3 S1 C1 . . 105.87(18) ?
O2 S1 C1 . . 106.64(17) ?
O1 S1 C1 . . 105.03(16) ?
S1 O2 H2A . . 109.5 ?
C2 C1 C6 . . 120.2(4) ?
C2 C1 S1 . . 118.1(3) ?
C6 C1 S1 . . 121.7(3) ?
C3 C2 C1 . . 120.8(4) ?
C3 C2 H2B . . 119.6 ?
C1 C2 H2B . . 119.6 ?
C2 C3 C4 . . 120.0(4) ?
C2 C3 H3B . . 120.0 ?
C4 C3 H3B . . 120.0 ?
C5 C4 C3 . . 119.6(4) ?
C5 C4 H4A . . 120.2 ?
C3 C4 H4A . . 120.2 ?
C4 C5 C6 . . 122.0(4) ?
C4 C5 H5A . . 119.0 ?
C6 C5 H5A . . 119.0 ?
C5 C6 C1 . . 117.3(3) ?
C5 C6 C7 . . 121.5(3) ?
C1 C6 C7 . . 121.2(3) ?
C8 C7 C6 . . 127.4(4) ?
C8 C7 H7A . . 116.3 ?
C6 C7 H7A . . 116.3 ?
C7 C8 C9 . . 125.7(4) ?
C7 C8 H8A . . 117.2 ?
C9 C8 H8A . . 117.2 ?
C14 C9 C10 . . 116.1(3) ?
C14 C9 C8 . . 123.5(3) ?
C10 C9 C8 . . 120.3(3) ?
C11 C10 C9 . . 122.0(4) ?
C11 C10 H10A . . 119.0 ?
C9 C10 H10A . . 119.0 ?
C10 C11 C12 . . 122.1(3) ?
C10 C11 H11A . . 118.9 ?
C12 C11 H11A . . 118.9 ?
C11 C12 C13 . . 116.2(3) ?
C11 C12 C12 . 3_667 123.0(4) ?
C13 C12 C12 . 3_667 120.8(4) ?
C14 C13 C12 . . 121.3(3) ?
C14 C13 H13A . . 119.4 ?
C12 C13 H13A . . 119.4 ?
C13 C14 C9 . . 122.2(3) ?
C13 C14 H14A . . 118.9 ?
C9 C14 H14A . . 118.9 ?
C20 C17 H17A . . 109.5 ?
C20 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C20 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C20 C15 C16 . . 113.0(4) ?
C20 C15 H15A . . 109.0 ?
C16 C15 H15A . . 109.0 ?
C20 C15 H15B . . 109.0 ?
C16 C15 H15B . . 109.0 ?
H15A C15 H15B . . 107.8 ?
N2 C16 C15 . . 109.6(4) ?
N2 C16 H16A . . 109.8 ?
C15 C16 H16A . . 109.8 ?
N2 C16 H16B . . 109.8 ?
C15 C16 H16B . . 109.8 ?
H16A C16 H16B . . 108.2 ?
C16 N2 C18 . . 112.2(4) ?
C16 N2 H2C . . 123.9 ?
C18 N2 H2C . . 123.9 ?
N2 C18 C19 . . 109.3(3) ?
N2 C18 H18A . . 109.8 ?
C19 C18 H18A . . 109.8 ?
N2 C18 H18B . . 109.8 ?
C19 C18 H18B . . 109.8 ?
H18A C18 H18B . . 108.3 ?
C18 C19 C20 . . 113.1(4) ?
C18 C19 H19A . . 109.0 ?
C20 C19 H19A . . 109.0 ?
C18 C19 H19B . . 109.0 ?
C20 C19 H19B . . 109.0 ?
H19A C19 H19B . . 107.8 ?
C15 C20 C19 . . 109.2(3) ?
C15 C20 C17 . . 111.4(4) ?
C19 C20 C17 . . 112.4(4) ?
C15 C20 H20A . . 107.9 ?
C19 C20 H20A . . 107.9 ?
C17 C20 H20A . . 107.9 ?
H2 O1W H1 . . 90(3) ?
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 O3 . 1.442(3) ?
S1 O2 . 1.446(3) ?
S1 O1 . 1.447(3) ?
S1 C1 . 1.784(4) ?
O2 H2A . 0.8200 ?
C1 C2 . 1.392(5) ?
C1 C6 . 1.417(5) ?
C2 C3 . 1.378(6) ?
C2 H2B . 0.9300 ?
C3 C4 . 1.389(6) ?
C3 H3B . 0.9300 ?
C4 C5 . 1.379(5) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.404(5) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.473(5) ?
C7 C8 . 1.326(5) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.469(5) ?
C8 H8A . 0.9300 ?
C9 C14 . 1.384(5) ?
C9 C10 . 1.387(5) ?
C10 C11 . 1.373(5) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.380(5) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.402(5) ?
C12 C12 3_667 1.488(6) ?
C13 C14 . 1.377(5) ?
C13 H13A . 0.9300 ?
C14 H14A . 0.9300 ?
C17 C20 . 1.537(5) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C15 C20 . 1.504(6) ?
C15 C16 . 1.519(6) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 N2 . 1.455(6) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
N2 C18 . 1.487(5) ?
N2 H2C . 0.8600 ?
C18 C19 . 1.488(5) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 C20 . 1.508(6) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 H20A . 0.9800 ?
O1W H2 . 0.90(4) ?
O1W H1 . 0.94(6) ?
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
O1W H1 O1 . 0.94(6) 1.95(6) 2.881(5) 171(6) yes
N2 H2C O1W 3_565 0.8600 2.2300 2.767(4) 120.00 yes
N2 H2C O3 4_575 0.8600 2.2800 2.787(5) 117.00 yes
C2 H2B O3 . 0.9300 2.4200 2.838(5) 107.00 yes
C7 H7A O2 . 0.9300 2.4200 3.103(5) 130.00 yes
