#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:08:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180467 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/36/7213615.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7213615
loop_
_publ_author_name
'Nowak, Anna M.'
'Kurc, Teresa'
'Janczak, Jan'
'Videnova-Adrabinska, Veneta'
_publ_section_title
;
 Synthesis and structural analysis of alkylammonium sulfoisophthalates:
 cation size and geometry effects on the hydrogen bonded network
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              591
_journal_paper_doi               10.1039/c3ce41526k
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C8 H5 O7 S, C6 H16 N, H2 O'
_chemical_formula_sum            'C14 H23 N O8 S'
_chemical_formula_weight         365.39
_chemical_name_systematic
; 
 ? 
;
_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                 105.892(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1122(3)
_cell_length_b                   9.5655(2)
_cell_length_c                   14.8057(5)
_cell_measurement_reflns_used    1282
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.67
_cell_volume                     1786.03(9)
_computing_cell_refinement
;
Oxford Diffraction Poland (2006). CrysAlis Red, 
Version 171.32.6, Wrocław, Poland
;
_computing_data_collection
;
Oxford Diffraction Poland (2006). CrysAlis CCD, 
Version 171.32.6, Wrocław, Poland
;
_computing_data_reduction
;
Oxford Diffraction Poland (2006). CrysAlis Red, 
Version 171.32.6, Wrocław, Poland
;
_computing_molecular_graphics
;
Brandenburg & Putz (2006). Diamond 3.0. Crystal and Molecular
Structure Visualisation, University of Bonn, Germany
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean \w-scan
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'KUMA KM-4 with area CCD detector'
_diffrn_measurement_method       '1024x1024 with blocks 2x2'
_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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24104
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.9577
_exptl_absorpt_correction_T_min  0.9412
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Oxford Diffraction Poland (2006). CrysAlis Red, 
Version 171.32.6, Wrocław, Poland
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      1.355
_exptl_crystal_density_method    floatation
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4427
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0377
_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)+(0.0310P)²+0.9582P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0980
_reflns_number_gt                2848
_reflns_number_total             4427
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c3ce41526k.txt
_cod_data_source_block           3
_cod_original_cell_volume        1786.03(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7213615
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.34321(3) 0.29202(5) 0.10823(3) 0.03864(13) Uani 1 1 d .
O1 O 0.33921(12) 0.2411(2) 0.01683(11) 0.0790(6) Uani 1 1 d .
O2 O 0.38971(10) 0.42861(14) 0.12873(12) 0.0598(4) Uani 1 1 d .
O3 O 0.39288(11) 0.19313(14) 0.18113(11) 0.0587(4) Uani 1 1 d .
C1 C 0.21017(12) 0.30633(17) 0.11393(12) 0.0321(4) Uani 1 1 d .
C2 C 0.15230(13) 0.18630(17) 0.11521(13) 0.0357(4) Uani 1 1 d .
H2 H 0.1826 0.0995 0.1109 0.043 Uiso 1 1 calc R
C3 C 0.04933(13) 0.19383(16) 0.12289(13) 0.0341(4) Uani 1 1 d .
C4 C 0.00436(13) 0.32347(17) 0.12913(13) 0.0353(4) Uani 1 1 d .
H4 H -0.0642 0.3294 0.1353 0.042 Uiso 1 1 calc R
C5 C 0.06180(13) 0.44394(16) 0.12613(12) 0.0337(4) Uani 1 1 d .
C6 C 0.16494(13) 0.43527(17) 0.11808(12) 0.0336(4) Uani 1 1 d .
H6 H 0.2032 0.5163 0.1155 0.040 Uiso 1 1 calc R
C7 C -0.00811(14) 0.06080(18) 0.12653(14) 0.0397(4) Uani 1 1 d .
O4 O 0.03541(12) -0.05071(13) 0.12322(13) 0.0687(5) Uani 1 1 d .
O5 O -0.10331(10) 0.07320(13) 0.13401(12) 0.0536(4) Uani 1 1 d D
H5O H -0.1318(18) -0.0034(13) 0.1336(18) 0.080 Uiso 1 1 d D
C8 C 0.01269(15) 0.58236(18) 0.13291(13) 0.0399(4) Uani 1 1 d .
O6 O -0.07278(11) 0.59551(14) 0.14746(12) 0.0592(4) Uani 1 1 d .
O7 O 0.07268(13) 0.68676(13) 0.12233(14) 0.0651(5) Uani 1 1 d D
H7O H 0.041(2) 0.7609(16) 0.122(2) 0.098 Uiso 1 1 d D
C11 C 0.67655(14) 0.3761(2) 0.22476(14) 0.0459(5) Uani 1 1 d .
H11 H 0.7461 0.3882 0.2702 0.069 Uiso 1 1 calc R
C12 C 0.66793(18) 0.2274(2) 0.19010(16) 0.0618(6) Uani 1 1 d .
H121 H 0.6005 0.2139 0.1449 0.093 Uiso 1 1 calc R
H122 H 0.6740 0.1649 0.2420 0.093 Uiso 1 1 calc R
H123 H 0.7237 0.2086 0.1612 0.093 Uiso 1 1 calc R
C13 C 0.6666(2) 0.4813(3) 0.14737(18) 0.0714(7) Uani 1 1 d .
H131 H 0.6000 0.4686 0.1009 0.107 Uiso 1 1 calc R
H132 H 0.7235 0.4685 0.1189 0.107 Uiso 1 1 calc R
H133 H 0.6699 0.5740 0.1729 0.107 Uiso 1 1 calc R
N1 N 0.59244(12) 0.40740(17) 0.27351(11) 0.0367(3) Uani 1 1 d .
H1N H 0.6004(16) 0.498(2) 0.2934(14) 0.055 Uiso 1 1 d .
H2N H 0.5304(18) 0.401(2) 0.2317(15) 0.055 Uiso 1 1 d .
C14 C 0.58750(16) 0.3190(2) 0.35572(14) 0.0472(5) Uani 1 1 d .
H14 H 0.5741 0.2218 0.3348 0.071 Uiso 1 1 calc R
C15 C 0.6911(2) 0.3256(3) 0.43159(16) 0.0712(7) Uani 1 1 d .
H151 H 0.7475 0.2943 0.4068 0.107 Uiso 1 1 calc R
H152 H 0.6872 0.2664 0.4829 0.107 Uiso 1 1 calc R
H153 H 0.7044 0.4201 0.4534 0.107 Uiso 1 1 calc R
C16 C 0.49507(19) 0.3704(3) 0.38912(17) 0.0714(7) Uani 1 1 d .
H161 H 0.4857 0.3104 0.4382 0.107 Uiso 1 1 calc R
H162 H 0.4318 0.3695 0.3377 0.107 Uiso 1 1 calc R
H163 H 0.5089 0.4640 0.4127 0.107 Uiso 1 1 calc R
O1W O 0.80589(11) 0.83913(15) 0.14242(11) 0.0517(4) Uani 1 1 d D
H1W H 0.7576(14) 0.825(3) 0.0947(11) 0.078 Uiso 1 1 d D
H2W H 0.8390(18) 0.7656(15) 0.1482(18) 0.078 Uiso 1 1 d D
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
O1 S1 O2 114.43(11)
O1 S1 O3 112.11(11)
O2 S1 O3 110.96(9)
O1 S1 C1 106.88(8)
O2 S1 C1 106.58(8)
O3 S1 C1 105.20(8)
C6 C1 C2 119.98(15)
C6 C1 S1 120.80(12)
C2 C1 S1 119.21(12)
C1 C2 C3 120.62(15)
C1 C2 H2 119.7
C3 C2 H2 119.7
C2 C3 C4 119.52(15)
C2 C3 C7 118.19(14)
C4 C3 C7 122.27(15)
C5 C4 C3 119.82(15)
C5 C4 H4 120.1
C3 C4 H4 120.1
C4 C5 C6 120.20(15)
C4 C5 C8 119.31(15)
C6 C5 C8 120.49(15)
C1 C6 C5 119.83(15)
C1 C6 H6 120.1
C5 C6 H6 120.1
O4 C7 O5 124.06(16)
O4 C7 C3 120.06(16)
O5 C7 C3 115.88(15)
C7 O5 H5O 111.5(18)
O6 C8 O7 124.18(17)
O6 C8 C5 123.10(17)
O7 C8 C5 112.71(16)
C8 O7 H7O 110(2)
C13 C11 N1 108.09(17)
C13 C11 C12 112.94(19)
N1 C11 C12 110.79(16)
C13 C11 H11 108.3
N1 C11 H11 108.3
C12 C11 H11 108.3
C11 C12 H121 109.5
C11 C12 H122 109.5
H121 C12 H122 109.5
C11 C12 H123 109.5
H121 C12 H123 109.5
H122 C12 H123 109.5
C11 C13 H131 109.5
C11 C13 H132 109.5
H131 C13 H132 109.5
C11 C13 H133 109.5
H131 C13 H133 109.5
H132 C13 H133 109.5
C14 N1 C11 118.55(15)
C14 N1 H1N 107.4(13)
C11 N1 H1N 108.1(13)
C14 N1 H2N 107.3(14)
C11 N1 H2N 107.9(14)
H1N N1 H2N 107.1(19)
N1 C14 C15 110.56(17)
N1 C14 C16 107.39(18)
C15 C14 C16 112.45(19)
N1 C14 H14 108.8
C15 C14 H14 108.8
C16 C14 H14 108.8
C14 C15 H151 109.5
C14 C15 H152 109.5
H151 C15 H152 109.5
C14 C15 H153 109.5
H151 C15 H153 109.5
H152 C15 H153 109.5
C14 C16 H161 109.5
C14 C16 H162 109.5
H161 C16 H162 109.5
C14 C16 H163 109.5
H161 C16 H163 109.5
H162 C16 H163 109.5
H1W O1W H2W 102(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4257(16)
S1 O2 1.4387(14)
S1 O3 1.4488(14)
S1 C1 1.7746(16)
C1 C6 1.377(2)
C1 C2 1.379(2)
C2 C3 1.388(2)
C2 H2 0.9300
C3 C4 1.387(2)
C3 C7 1.487(2)
C4 C5 1.384(2)
C4 H4 0.9300
C5 C6 1.392(2)
C5 C8 1.488(2)
C6 H6 0.9300
C7 O4 1.217(2)
C7 O5 1.289(2)
O5 H5O 0.822(5)
C8 O6 1.204(2)
C8 O7 1.307(2)
O7 H7O 0.820(5)
C11 C13 1.504(3)
C11 N1 1.504(2)
C11 C12 1.506(3)
C11 H11 0.9800
C12 H121 0.9600
C12 H122 0.9600
C12 H123 0.9600
C13 H131 0.9600
C13 H132 0.9600
C13 H133 0.9600
N1 C14 1.498(2)
N1 H1N 0.91(2)
N1 H2N 0.88(2)
C14 C15 1.508(3)
C14 C16 1.511(3)
C14 H14 0.9800
C15 H151 0.9600
C15 H152 0.9600
C15 H153 0.9600
C16 H161 0.9600
C16 H162 0.9600
C16 H163 0.9600
O1W H1W 0.82(2)
O1W H2W 0.82(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5O O1W 0.82(1) 1.74(1) 2.555(2) 175(3) 1_445
O7 H7O O4 0.82(2) 1.80(1) 2.559(2) 153(3) 1_565
N1 H1N O3 0.91(2) 1.90(2) 2.808(2) 173(2) 2_655
N1 H2N O2 0.88(2) 2.06(2) 2.929(2) 168(2) .
O1W H1W O1 0.82(1) 1.90(1) 2.704(2) 169(3) 3_665
O1W H2W O6 0.82(1) 2.00(1) 2.811(2) 172(3) 1_655
