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organic compounds
Benzyltributylammonium 4,6-dihydroxynaphthalene-2-sulfonate
aDepartment of Applied Physics, Graduate School of Engineering, Yokohama National University, 79-5 Tokiwadai, Hodogaya-ku, 240-8501 Yokohama, Japan
*Correspondence e-mail: mizu-j@ynu.ac.jp
The title molecular salt, C19H34N+·C10H7O5S−, is a charge-control agent used for toners in with a high melting point of 508 K. In the the anions form inversion dimers, linked by pairs of O—H⋯O hydrogen bonds. Further O—H⋯O links between dimers generate anionic sheets propagating in (010). One of the n-butyl chains of the cation is disordered over two sets of sites in a 0.53:0.47 ratio.
Related literature
For background on charge-control agents, see: Nash et al. (2001) and Uta et al. (2009
). For the structures of benzyltributylammonium 4-hydroxynaphthalene-1-sulfonate, benzyltributylammonium 6-hydroxynaphthalene-2-sulfonate, benzyltributylammonium 4-hydroxynaphthalene-2-sulfonate and benzyltributylammonium 7-hydroxynaphthalene-1-sulfonate, see: Mizuguchi et al. (2007
), Uta et al. (2009
), Uta & Mizuguchi (2009
) and Sato et al. (2009
), respectively.
Experimental
Crystal data
|
Refinement
|
|
Data collection: PROCESS-AUTO (Rigaku, 2006); cell PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2006
); program(s) used to solve structure: SIR2004 (Burla et al., 2003
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: ORTEPIII (Burnett & Johnson, 1996
); software used to prepare material for publication: CrystalStructure.
Supporting information
10.1107/S1600536809000415/hb2891sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809000415/hb2891Isup2.hkl
The title compound was obtained from Orient Chemical Industries Ltd., and was recrystallized from an methanol solution. After 48 h, a number of colourless crystals were obtained in the form of blocks of (I).
C18 and C19 were found to be disordered over two sites each. The site occupancies for C18A/C18B and C19A/C19B are 0.53/0.47. These atoms were refined anisotropically. All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 Å (aromatic), 0.96 Å (methyl), or 0.97 Å (methylene), and O—H = 0.82 Å; Uiso(H) = 1.2Ueq(parent atom). The deepest hole is located 0.79Å from atom S1. The high R value of the present analysis can presumably be attributed to the poor crystallinity of the sample, although its size is sufficient.
Data collection: PROCESS-AUTO (Rigaku, 2006); cell
PROCESS-AUTO (Rigaku, 2006); data reduction: CrystalStructure (Rigaku, 2006); program(s) used to solve structure: SIR2004 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure (Rigaku, 2006).C19H34N+·C10H7O5S− | F(000) = 2224.00 |
Mr = 515.70 | Dx = 1.214 Mg m−3 |
Orthorhombic, Pbca | Cu Kα radiation, λ = 1.54187 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 29523 reflections |
a = 18.6976 (3) Å | θ = 3.3–68.2° |
b = 15.3045 (2) Å | µ = 1.32 mm−1 |
c = 19.7287 (3) Å | T = 296 K |
V = 5645.51 (14) Å3 | Block, colourless |
Z = 8 | 0.50 × 0.45 × 0.40 mm |
Rigaku R-AXIS RAPID diffractometer | 2937 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.070 |
ω scans | θmax = 68.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −22→22 |
Tmin = 0.425, Tmax = 0.517 | k = −18→18 |
49979 measured reflections | l = −23→23 |
5149 independent reflections |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.196 | w = 1/[σ2(Fo2) + (0.3P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.547 | (Δ/σ)max < 0.001 |
S = 1.49 | Δρmax = 0.46 e Å−3 |
5149 reflections | Δρmin = −1.55 e Å−3 |
332 parameters |
C19H34N+·C10H7O5S− | V = 5645.51 (14) Å3 |
Mr = 515.70 | Z = 8 |
Orthorhombic, Pbca | Cu Kα radiation |
a = 18.6976 (3) Å | µ = 1.32 mm−1 |
b = 15.3045 (2) Å | T = 296 K |
c = 19.7287 (3) Å | 0.50 × 0.45 × 0.40 mm |
Rigaku R-AXIS RAPID diffractometer | 5149 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2937 reflections with F2 > 2σ(F2) |
Tmin = 0.425, Tmax = 0.517 | Rint = 0.070 |
49979 measured reflections |
R[F2 > 2σ(F2)] = 0.196 | 332 parameters |
wR(F2) = 0.547 | H-atom parameters constrained |
S = 1.49 | Δρmax = 0.46 e Å−3 |
5149 reflections | Δρmin = −1.55 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.57640 (9) | −0.08254 (12) | 0.11259 (8) | 0.0863 (7) | |
O1 | 0.5860 (2) | −0.1387 (3) | 0.0538 (2) | 0.1069 (16) | |
O2 | 0.6038 (2) | 0.0070 (3) | 0.1008 (2) | 0.0958 (13) | |
O3 | 0.6031 (2) | −0.1202 (3) | 0.1753 (2) | 0.0985 (14) | |
O4 | 0.3225 (2) | −0.0388 (3) | 0.0178 (2) | 0.1020 (14) | |
O5 | 0.1550 (2) | −0.0580 (3) | 0.2110 (2) | 0.1031 (14) | |
N1 | 0.4640 (2) | 0.2386 (3) | 0.1198 (2) | 0.0886 (15) | |
C1 | 0.6461 (4) | 0.2299 (6) | 0.1023 (4) | 0.120 (2) | |
C2 | 0.7111 (5) | 0.2710 (8) | 0.0881 (6) | 0.141 (3) | |
C3 | 0.7168 (7) | 0.3210 (8) | 0.0321 (7) | 0.161 (4) | |
C4 | 0.6604 (6) | 0.3332 (8) | −0.0113 (7) | 0.157 (3) | |
C5 | 0.5955 (5) | 0.2916 (7) | 0.0026 (5) | 0.134 (3) | |
C6 | 0.5872 (3) | 0.2396 (5) | 0.0600 (4) | 0.098 (2) | |
C7 | 0.5181 (3) | 0.1910 (5) | 0.0727 (3) | 0.098 (2) | |
C8 | 0.4935 (4) | 0.2484 (5) | 0.1924 (3) | 0.100 (2) | |
C9 | 0.5092 (5) | 0.1646 (6) | 0.2294 (3) | 0.121 (2) | |
C10 | 0.5168 (6) | 0.1769 (6) | 0.3031 (4) | 0.134 (3) | |
C11 | 0.5276 (6) | 0.0902 (6) | 0.3404 (5) | 0.144 (3) | |
C12 | 0.4475 (4) | 0.3312 (4) | 0.0937 (3) | 0.0960 (19) | |
C13 | 0.4049 (4) | 0.3341 (4) | 0.0280 (4) | 0.105 (2) | |
C14 | 0.4016 (5) | 0.4253 (5) | 0.0017 (4) | 0.117 (2) | |
C15 | 0.3534 (6) | 0.4327 (7) | −0.0593 (5) | 0.146 (3) | |
C16 | 0.3975 (3) | 0.1816 (5) | 0.1193 (4) | 0.102 (2) | |
C17 | 0.3383 (4) | 0.2173 (5) | 0.1649 (5) | 0.136 (3) | |
C18A | 0.2950 (11) | 0.1572 (10) | 0.1998 (15) | 0.136 (3) | 0.53 |
C18B | 0.2741 (8) | 0.1655 (15) | 0.1599 (12) | 0.123 (6) | 0.47 |
C19A | 0.2290 (14) | 0.2034 (18) | 0.230 (2) | 0.190 (7) | 0.53 |
C19B | 0.2168 (17) | 0.163 (2) | 0.217 (2) | 0.190 (7) | 0.47 |
C20 | 0.4837 (3) | −0.0710 (4) | 0.1227 (3) | 0.0823 (17) | |
C21 | 0.4407 (3) | −0.0583 (4) | 0.0648 (3) | 0.0859 (16) | |
C22 | 0.3669 (3) | −0.0524 (4) | 0.0723 (3) | 0.0809 (15) | |
C23 | 0.3341 (3) | −0.0600 (3) | 0.1368 (2) | 0.0770 (14) | |
C24 | 0.2586 (3) | −0.0569 (4) | 0.1444 (3) | 0.0860 (17) | |
C25 | 0.2293 (3) | −0.0607 (4) | 0.2068 (3) | 0.0840 (16) | |
C26 | 0.2706 (4) | −0.0672 (4) | 0.2650 (3) | 0.0964 (19) | |
C27 | 0.3450 (3) | −0.0732 (4) | 0.2580 (3) | 0.0898 (18) | |
C28 | 0.3771 (3) | −0.0692 (4) | 0.1947 (2) | 0.0793 (15) | |
C29 | 0.4536 (3) | −0.0750 (4) | 0.1870 (3) | 0.0824 (16) | |
H1 | 0.6421 | 0.1954 | 0.1409 | 0.144* | |
H2 | 0.7500 | 0.2639 | 0.1170 | 0.169* | |
H3 | 0.7603 | 0.3480 | 0.0227 | 0.193* | |
H4 | 0.6653 | 0.3686 | −0.0494 | 0.188* | |
H4O | 0.3466 | −0.0336 | −0.0167 | 0.122* | |
H5 | 0.5572 | 0.2987 | −0.0270 | 0.161* | |
H5O | 0.1428 | −0.0617 | 0.2508 | 0.124* | |
H7A | 0.5294 | 0.1347 | 0.0925 | 0.118* | |
H7B | 0.4952 | 0.1802 | 0.0294 | 0.118* | |
H8A | 0.5372 | 0.2824 | 0.1903 | 0.119* | |
H8B | 0.4592 | 0.2816 | 0.2188 | 0.119* | |
H9A | 0.4709 | 0.1234 | 0.2208 | 0.145* | |
H9B | 0.5531 | 0.1397 | 0.2116 | 0.145* | |
H10A | 0.4742 | 0.2054 | 0.3205 | 0.160* | |
H10B | 0.5573 | 0.2148 | 0.3119 | 0.160* | |
H11A | 0.4981 | 0.0461 | 0.3202 | 0.217* | |
H11B | 0.5147 | 0.0972 | 0.3872 | 0.217* | |
H11C | 0.5769 | 0.0731 | 0.3373 | 0.217* | |
H12A | 0.4210 | 0.3624 | 0.1284 | 0.115* | |
H12B | 0.4923 | 0.3619 | 0.0868 | 0.115* | |
H13A | 0.4274 | 0.2966 | −0.0055 | 0.126* | |
H13B | 0.3569 | 0.3125 | 0.0360 | 0.126* | |
H14A | 0.4493 | 0.4444 | −0.0105 | 0.140* | |
H14B | 0.3841 | 0.4636 | 0.0372 | 0.140* | |
H15A | 0.3689 | 0.3924 | −0.0935 | 0.218* | |
H15B | 0.3554 | 0.4912 | −0.0768 | 0.218* | |
H15C | 0.3051 | 0.4192 | −0.0463 | 0.218* | |
H16A | 0.4101 | 0.1233 | 0.1343 | 0.123* | |
H16B | 0.3796 | 0.1773 | 0.0733 | 0.123* | |
H17A | 0.3603 | 0.2553 | 0.1983 | 0.163* | 0.53 |
H17B | 0.3073 | 0.2534 | 0.1372 | 0.163* | 0.53 |
H17C | 0.3547 | 0.2175 | 0.2116 | 0.163* | 0.47 |
H17D | 0.3277 | 0.2771 | 0.1521 | 0.163* | 0.47 |
H18A | 0.3224 | 0.1302 | 0.2359 | 0.163* | 0.53 |
H18B | 0.2796 | 0.1116 | 0.1690 | 0.163* | 0.53 |
H18C | 0.2891 | 0.1056 | 0.1525 | 0.148* | 0.47 |
H18D | 0.2497 | 0.1839 | 0.1189 | 0.148* | 0.47 |
H19A | 0.2411 | 0.2277 | 0.2733 | 0.284* | 0.53 |
H19B | 0.1909 | 0.1620 | 0.2352 | 0.284* | 0.53 |
H19C | 0.2140 | 0.2494 | 0.2000 | 0.284* | 0.53 |
H19D | 0.2180 | 0.2174 | 0.2419 | 0.284* | 0.47 |
H19E | 0.2269 | 0.1158 | 0.2476 | 0.284* | 0.47 |
H19F | 0.1702 | 0.1554 | 0.1977 | 0.284* | 0.47 |
H21 | 0.4614 | −0.0538 | 0.0221 | 0.103* | |
H24 | 0.2294 | −0.0523 | 0.1065 | 0.103* | |
H26 | 0.2494 | −0.0675 | 0.3076 | 0.116* | |
H27 | 0.3732 | −0.0800 | 0.2964 | 0.108* | |
H29 | 0.4826 | −0.0815 | 0.2249 | 0.099* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0805 (10) | 0.1074 (13) | 0.0711 (11) | 0.0042 (7) | −0.0076 (6) | −0.0044 (7) |
O1 | 0.091 (2) | 0.143 (4) | 0.087 (2) | 0.019 (2) | −0.004 (2) | −0.046 (2) |
O2 | 0.091 (2) | 0.104 (3) | 0.092 (2) | −0.019 (2) | 0.003 (2) | 0.011 (2) |
O3 | 0.084 (2) | 0.134 (3) | 0.077 (2) | 0.004 (2) | −0.015 (2) | 0.015 (2) |
O4 | 0.090 (2) | 0.151 (4) | 0.065 (2) | −0.001 (2) | −0.004 (2) | 0.012 (2) |
O5 | 0.076 (2) | 0.145 (3) | 0.088 (3) | 0.001 (2) | 0.008 (2) | 0.002 (2) |
N1 | 0.089 (3) | 0.095 (3) | 0.082 (3) | 0.004 (2) | 0.003 (2) | −0.010 (2) |
C1 | 0.108 (5) | 0.152 (7) | 0.100 (5) | −0.010 (5) | −0.010 (4) | −0.016 (4) |
C2 | 0.105 (5) | 0.191 (10) | 0.127 (7) | −0.024 (6) | 0.005 (5) | −0.034 (7) |
C3 | 0.130 (8) | 0.159 (9) | 0.195 (13) | −0.013 (7) | 0.046 (9) | −0.017 (9) |
C4 | 0.126 (7) | 0.178 (9) | 0.165 (9) | −0.004 (7) | 0.033 (7) | 0.033 (8) |
C5 | 0.124 (6) | 0.173 (8) | 0.106 (6) | 0.012 (6) | 0.019 (5) | 0.017 (6) |
C6 | 0.090 (4) | 0.110 (5) | 0.094 (4) | 0.007 (3) | 0.004 (3) | −0.020 (3) |
C7 | 0.084 (3) | 0.117 (5) | 0.093 (4) | 0.005 (3) | 0.010 (3) | −0.021 (3) |
C8 | 0.114 (5) | 0.107 (4) | 0.077 (4) | 0.004 (3) | 0.004 (3) | −0.016 (3) |
C9 | 0.150 (7) | 0.128 (6) | 0.085 (5) | 0.017 (5) | −0.010 (4) | −0.004 (4) |
C10 | 0.176 (8) | 0.128 (6) | 0.097 (6) | 0.036 (6) | −0.006 (5) | −0.006 (4) |
C11 | 0.155 (8) | 0.176 (9) | 0.102 (6) | 0.032 (6) | 0.013 (6) | 0.008 (5) |
C12 | 0.096 (4) | 0.095 (4) | 0.097 (4) | −0.000 (3) | 0.001 (3) | 0.004 (3) |
C13 | 0.110 (4) | 0.102 (4) | 0.104 (5) | −0.000 (4) | −0.009 (4) | 0.013 (3) |
C14 | 0.125 (6) | 0.117 (5) | 0.108 (5) | 0.002 (4) | 0.004 (5) | 0.013 (4) |
C15 | 0.161 (9) | 0.136 (7) | 0.140 (8) | 0.023 (6) | 0.003 (7) | 0.018 (6) |
C16 | 0.081 (3) | 0.108 (5) | 0.119 (6) | −0.012 (3) | 0.011 (3) | −0.012 (4) |
C17 | 0.116 (5) | 0.117 (5) | 0.175 (8) | −0.009 (4) | 0.052 (5) | −0.006 (5) |
C18A | 0.116 (5) | 0.117 (5) | 0.175 (8) | −0.009 (4) | 0.052 (5) | −0.006 (5) |
C18B | 0.097 (10) | 0.158 (15) | 0.114 (13) | −0.013 (9) | −0.007 (8) | −0.011 (11) |
C19A | 0.150 (11) | 0.131 (17) | 0.288 (18) | −0.026 (10) | 0.112 (12) | −0.067 (15) |
C19B | 0.150 (11) | 0.131 (17) | 0.288 (18) | −0.026 (10) | 0.112 (12) | −0.067 (15) |
C20 | 0.092 (4) | 0.096 (3) | 0.059 (3) | −0.003 (3) | −0.007 (2) | −0.001 (2) |
C21 | 0.084 (3) | 0.101 (3) | 0.074 (3) | 0.004 (3) | −0.008 (3) | −0.003 (3) |
C22 | 0.069 (3) | 0.104 (4) | 0.070 (3) | −0.002 (3) | −0.012 (2) | −0.002 (2) |
C23 | 0.085 (3) | 0.092 (3) | 0.054 (2) | −0.006 (2) | 0.002 (2) | 0.003 (2) |
C24 | 0.071 (3) | 0.113 (4) | 0.074 (3) | 0.002 (3) | −0.000 (2) | 0.004 (3) |
C25 | 0.075 (3) | 0.098 (4) | 0.079 (3) | −0.010 (3) | 0.001 (2) | 0.002 (3) |
C26 | 0.105 (4) | 0.122 (5) | 0.062 (3) | 0.001 (3) | 0.005 (3) | 0.005 (3) |
C27 | 0.082 (3) | 0.122 (5) | 0.065 (3) | −0.007 (3) | 0.002 (2) | −0.000 (3) |
C28 | 0.086 (3) | 0.096 (3) | 0.055 (2) | 0.009 (3) | −0.001 (2) | 0.003 (2) |
C29 | 0.075 (3) | 0.103 (4) | 0.069 (3) | 0.003 (2) | −0.009 (2) | 0.001 (2) |
S1—O1 | 1.455 (5) | C4—H4 | 0.930 |
S1—O2 | 1.481 (5) | C5—H5 | 0.930 |
S1—O3 | 1.453 (4) | C7—H7A | 0.970 |
S1—C20 | 1.753 (7) | C7—H7B | 0.970 |
O4—C22 | 1.375 (7) | C8—H8A | 0.970 |
O5—C25 | 1.392 (7) | C8—H8B | 0.970 |
N1—C7 | 1.555 (9) | C9—H9A | 0.970 |
N1—C8 | 1.543 (8) | C9—H9B | 0.970 |
N1—C12 | 1.540 (9) | C10—H10A | 0.970 |
N1—C16 | 1.519 (9) | C10—H10B | 0.970 |
C1—C2 | 1.398 (14) | C11—H11A | 0.960 |
C1—C6 | 1.388 (11) | C11—H11B | 0.960 |
C2—C3 | 1.348 (19) | C11—H11C | 0.960 |
C3—C4 | 1.372 (19) | C12—H12A | 0.970 |
C4—C5 | 1.399 (16) | C12—H12B | 0.970 |
C5—C6 | 1.394 (13) | C13—H13A | 0.970 |
C6—C7 | 1.511 (10) | C13—H13B | 0.970 |
C8—C9 | 1.504 (11) | C14—H14A | 0.970 |
C9—C10 | 1.473 (11) | C14—H14B | 0.970 |
C10—C11 | 1.530 (13) | C15—H15A | 0.960 |
C12—C13 | 1.522 (11) | C15—H15B | 0.960 |
C13—C14 | 1.491 (10) | C15—H15C | 0.960 |
C14—C15 | 1.507 (14) | C16—H16A | 0.970 |
C16—C17 | 1.527 (12) | C16—H16B | 0.970 |
C17—C18A | 1.40 (2) | C17—H17A | 0.970 |
C17—C18B | 1.44 (2) | C17—H17B | 0.970 |
C18A—C19A | 1.54 (3) | C17—H17C | 0.970 |
C18B—C19B | 1.56 (4) | C17—H17D | 0.970 |
C20—C21 | 1.411 (9) | C18A—H18A | 0.970 |
C20—C29 | 1.389 (8) | C18A—H18B | 0.970 |
C21—C22 | 1.389 (8) | C18B—H18C | 0.970 |
C22—C23 | 1.416 (8) | C18B—H18D | 0.970 |
C23—C24 | 1.421 (8) | C19A—H19A | 0.960 |
C23—C28 | 1.405 (8) | C19A—H19B | 0.960 |
C24—C25 | 1.347 (9) | C19A—H19C | 0.960 |
C25—C26 | 1.387 (9) | C19B—H19D | 0.960 |
C26—C27 | 1.401 (10) | C19B—H19E | 0.960 |
C27—C28 | 1.387 (8) | C19B—H19F | 0.960 |
C28—C29 | 1.440 (9) | C21—H21 | 0.930 |
O4—H4O | 0.820 | C24—H24 | 0.930 |
O5—H5O | 0.820 | C26—H26 | 0.930 |
C1—H1 | 0.930 | C27—H27 | 0.930 |
C2—H2 | 0.930 | C29—H29 | 0.930 |
C3—H3 | 0.930 | ||
O2···O4i | 2.758 (6) | O5···H12Avi | 2.482 |
O3···O5ii | 2.623 (6) | O5···H17Avi | 2.883 |
O4···O2i | 2.758 (6) | O5···H17Dvi | 2.797 |
O5···O3iii | 2.623 (6) | C2···H19Aii | 2.869 |
S1···H4Oi | 2.967 | C4···H18Dvii | 2.713 |
S1···H5Oii | 2.984 | C7···H21i | 2.837 |
O1···H3iv | 2.946 | C10···H19Fii | 2.888 |
O1···H13Ai | 2.609 | C11···H19Fii | 2.944 |
O1···H7Bi | 2.323 | C21···H7Bi | 2.895 |
O1···H16Bi | 2.655 | C23···H18B | 2.888 |
O2···H4Oi | 1.943 | C23···H18C | 2.688 |
O2···H21i | 2.807 | C24···H18B | 2.653 |
O2···H7A | 2.403 | C24···H18C | 2.556 |
O3···H5Oii | 1.865 | C25···H17Dvi | 2.909 |
O3···H8Bv | 2.825 | C25···H18B | 2.897 |
O3···H26ii | 2.871 | C25···H18C | 2.979 |
O4···H15Cvi | 2.777 | C25···H19E | 2.820 |
O5···H11Ciii | 2.659 | C26···H19E | 2.937 |
O1—S1—O2 | 112.3 (2) | C9—C10—H10A | 109.2 |
O1—S1—O3 | 113.7 (3) | C9—C10—H10B | 109.2 |
O1—S1—C20 | 105.8 (2) | C11—C10—H10A | 109.2 |
O2—S1—O3 | 112.4 (2) | C11—C10—H10B | 109.2 |
O2—S1—C20 | 105.4 (2) | H10A—C10—H10B | 107.9 |
O3—S1—C20 | 106.4 (2) | C10—C11—H11A | 109.5 |
C7—N1—C8 | 111.6 (5) | C10—C11—H11B | 109.5 |
C7—N1—C12 | 111.2 (5) | C10—C11—H11C | 109.5 |
C7—N1—C16 | 105.2 (5) | H11A—C11—H11B | 109.5 |
C8—N1—C12 | 107.0 (5) | H11A—C11—H11C | 109.5 |
C8—N1—C16 | 110.8 (5) | H11B—C11—H11C | 109.5 |
C12—N1—C16 | 111.3 (5) | N1—C12—H12A | 108.6 |
C2—C1—C6 | 121.4 (8) | N1—C12—H12B | 108.6 |
C1—C2—C3 | 119.3 (10) | C13—C12—H12A | 108.6 |
C2—C3—C4 | 121.9 (11) | C13—C12—H12B | 108.6 |
C3—C4—C5 | 118.9 (11) | H12A—C12—H12B | 107.6 |
C4—C5—C6 | 121.0 (9) | C12—C13—H13A | 109.6 |
C1—C6—C5 | 117.5 (7) | C12—C13—H13B | 109.6 |
C1—C6—C7 | 121.7 (7) | C14—C13—H13A | 109.6 |
C5—C6—C7 | 120.6 (7) | C14—C13—H13B | 109.6 |
N1—C7—C6 | 115.1 (6) | H13A—C13—H13B | 108.1 |
N1—C8—C9 | 115.9 (6) | C13—C14—H14A | 109.2 |
C8—C9—C10 | 112.9 (7) | C13—C14—H14B | 109.2 |
C9—C10—C11 | 112.2 (7) | C15—C14—H14A | 109.2 |
N1—C12—C13 | 114.5 (5) | C15—C14—H14B | 109.2 |
C12—C13—C14 | 110.2 (6) | H14A—C14—H14B | 107.9 |
C13—C14—C15 | 111.9 (7) | C14—C15—H15A | 109.5 |
N1—C16—C17 | 112.7 (6) | C14—C15—H15B | 109.5 |
C16—C17—C18A | 118.2 (10) | C14—C15—H15C | 109.5 |
C16—C17—C18B | 111.5 (11) | H15A—C15—H15B | 109.5 |
C17—C18A—C19A | 110.4 (15) | H15A—C15—H15C | 109.5 |
C17—C18B—C19B | 122 (2) | H15B—C15—H15C | 109.5 |
S1—C20—C21 | 119.1 (4) | N1—C16—H16A | 109.1 |
S1—C20—C29 | 120.1 (4) | N1—C16—H16B | 109.1 |
C21—C20—C29 | 120.8 (6) | C17—C16—H16A | 109.1 |
C20—C21—C22 | 119.3 (5) | C17—C16—H16B | 109.1 |
O4—C22—C21 | 121.7 (5) | H16A—C16—H16B | 107.8 |
O4—C22—C23 | 117.0 (5) | C16—C17—H17A | 107.8 |
C21—C22—C23 | 121.3 (5) | C16—C17—H17B | 107.8 |
C22—C23—C24 | 121.5 (5) | C16—C17—H17C | 109.3 |
C22—C23—C28 | 119.4 (5) | C16—C17—H17D | 109.3 |
C24—C23—C28 | 119.0 (5) | C18A—C17—H17A | 107.8 |
C23—C24—C25 | 120.0 (5) | C18A—C17—H17B | 107.8 |
O5—C25—C24 | 117.3 (5) | C18B—C17—H17C | 109.3 |
O5—C25—C26 | 120.5 (5) | C18B—C17—H17D | 109.3 |
C24—C25—C26 | 122.2 (6) | H17A—C17—H17B | 107.1 |
C25—C26—C27 | 118.4 (6) | H17C—C17—H17D | 108.0 |
C26—C27—C28 | 121.1 (6) | C17—C18A—H18A | 109.6 |
C23—C28—C27 | 119.2 (6) | C17—C18A—H18B | 109.6 |
C23—C28—C29 | 119.2 (5) | C19A—C18A—H18A | 109.6 |
C27—C28—C29 | 121.6 (5) | C19A—C18A—H18B | 109.6 |
C20—C29—C28 | 119.8 (5) | H18A—C18A—H18B | 108.1 |
C22—O4—H4O | 109.5 | C17—C18B—H18C | 106.8 |
C25—O5—H5O | 109.5 | C17—C18B—H18D | 106.8 |
C2—C1—H1 | 119.3 | C19B—C18B—H18C | 106.8 |
C6—C1—H1 | 119.3 | C19B—C18B—H18D | 106.8 |
C1—C2—H2 | 120.4 | H18C—C18B—H18D | 106.6 |
C3—C2—H2 | 120.4 | C18A—C19A—H19A | 109.5 |
C2—C3—H3 | 119.1 | C18A—C19A—H19B | 109.5 |
C4—C3—H3 | 119.1 | C18A—C19A—H19C | 109.5 |
C3—C4—H4 | 120.6 | H19A—C19A—H19B | 109.5 |
C5—C4—H4 | 120.6 | H19A—C19A—H19C | 109.5 |
C4—C5—H5 | 119.5 | H19B—C19A—H19C | 109.5 |
C6—C5—H5 | 119.5 | C18B—C19B—H19D | 109.5 |
N1—C7—H7A | 108.5 | C18B—C19B—H19E | 109.5 |
N1—C7—H7B | 108.5 | C18B—C19B—H19F | 109.5 |
C6—C7—H7A | 108.5 | H19D—C19B—H19E | 109.5 |
C6—C7—H7B | 108.5 | H19D—C19B—H19F | 109.5 |
H7A—C7—H7B | 107.5 | H19E—C19B—H19F | 109.5 |
N1—C8—H8A | 108.3 | C20—C21—H21 | 120.4 |
N1—C8—H8B | 108.3 | C22—C21—H21 | 120.3 |
C9—C8—H8A | 108.3 | C23—C24—H24 | 120.0 |
C9—C8—H8B | 108.3 | C25—C24—H24 | 120.0 |
H8A—C8—H8B | 107.4 | C25—C26—H26 | 120.8 |
C8—C9—H9A | 109.0 | C27—C26—H26 | 120.8 |
C8—C9—H9B | 109.0 | C26—C27—H27 | 119.5 |
C10—C9—H9A | 109.0 | C28—C27—H27 | 119.5 |
C10—C9—H9B | 109.0 | C20—C29—H29 | 120.1 |
H9A—C9—H9B | 107.8 | C28—C29—H29 | 120.1 |
O1—S1—C20—C21 | −41.9 (6) | C12—C13—C14—C15 | −173.9 (7) |
O1—S1—C20—C29 | 137.6 (5) | N1—C16—C17—C18A | −144.5 (14) |
O2—S1—C20—C21 | 77.2 (5) | N1—C16—C17—C18B | 175.9 (11) |
O2—S1—C20—C29 | −103.3 (5) | C16—C17—C18A—C19A | −167.5 (18) |
O3—S1—C20—C21 | −163.2 (5) | C16—C17—C18B—C19B | 156.7 (19) |
O3—S1—C20—C29 | 16.3 (6) | S1—C20—C21—C22 | 177.5 (5) |
C7—N1—C8—C9 | −61.7 (8) | S1—C20—C29—C28 | −177.4 (4) |
C8—N1—C7—C6 | −64.9 (7) | C21—C20—C29—C28 | 2.1 (9) |
C7—N1—C12—C13 | 68.9 (7) | C29—C20—C21—C22 | −2.0 (10) |
C12—N1—C7—C6 | 54.5 (7) | C20—C21—C22—O4 | 179.0 (6) |
C7—N1—C16—C17 | 178.5 (6) | C20—C21—C22—C23 | −0.8 (10) |
C16—N1—C7—C6 | 175.0 (6) | O4—C22—C23—C24 | 2.2 (9) |
C8—N1—C12—C13 | −169.1 (6) | O4—C22—C23—C28 | −176.5 (5) |
C12—N1—C8—C9 | 176.5 (6) | C21—C22—C23—C24 | −177.9 (6) |
C8—N1—C16—C17 | 57.9 (8) | C21—C22—C23—C28 | 3.3 (9) |
C16—N1—C8—C9 | 55.1 (8) | C22—C23—C24—C25 | −177.2 (6) |
C12—N1—C16—C17 | −61.0 (8) | C22—C23—C28—C27 | 177.5 (6) |
C16—N1—C12—C13 | −48.0 (8) | C22—C23—C28—C29 | −3.1 (8) |
C2—C1—C6—C5 | 0.2 (10) | C24—C23—C28—C27 | −1.3 (9) |
C2—C1—C6—C7 | 176.1 (9) | C24—C23—C28—C29 | 178.1 (5) |
C6—C1—C2—C3 | −0.0 (16) | C28—C23—C24—C25 | 1.5 (9) |
C1—C2—C3—C4 | 0.3 (15) | C23—C24—C25—O5 | −179.6 (5) |
C2—C3—C4—C5 | −0.9 (18) | C23—C24—C25—C26 | 0.4 (8) |
C3—C4—C5—C6 | 1.1 (17) | O5—C25—C26—C27 | 177.5 (6) |
C4—C5—C6—C1 | −0.8 (14) | C24—C25—C26—C27 | −2.5 (10) |
C4—C5—C6—C7 | −176.7 (9) | C25—C26—C27—C28 | 2.7 (10) |
C1—C6—C7—N1 | 88.7 (9) | C26—C27—C28—C23 | −0.8 (9) |
C5—C6—C7—N1 | −95.5 (9) | C26—C27—C28—C29 | 179.8 (4) |
N1—C8—C9—C10 | −163.2 (7) | C23—C28—C29—C20 | 0.4 (7) |
C8—C9—C10—C11 | 176.1 (8) | C27—C28—C29—C20 | 179.8 (4) |
N1—C12—C13—C14 | −171.3 (6) |
Symmetry codes: (i) −x+1, −y, −z; (ii) x+1/2, y, −z+1/2; (iii) x−1/2, y, −z+1/2; (iv) −x+3/2, y−1/2, z; (v) −x+1, y−1/2, −z+1/2; (vi) −x+1/2, y−1/2, z; (vii) x+1/2, −y+1/2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4O···O2i | 0.82 | 1.94 | 2.758 (6) | 172 |
O5—H5O···O3iii | 0.82 | 1.87 | 2.623 (6) | 153 |
Symmetry codes: (i) −x+1, −y, −z; (iii) x−1/2, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H34N+·C10H7O5S− |
Mr | 515.70 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 296 |
a, b, c (Å) | 18.6976 (3), 15.3045 (2), 19.7287 (3) |
V (Å3) | 5645.51 (14) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 1.32 |
Crystal size (mm) | 0.50 × 0.45 × 0.40 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.425, 0.517 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 49979, 5149, 2937 |
Rint | 0.070 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.196, 0.547, 1.49 |
No. of reflections | 5149 |
No. of parameters | 332 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.46, −1.55 |
Computer programs: PROCESS-AUTO (Rigaku, 2006), CrystalStructure (Rigaku, 2006), SIR2004 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4O···O2i | 0.82 | 1.94 | 2.758 (6) | 172 |
O5—H5O···O3ii | 0.82 | 1.87 | 2.623 (6) | 153 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x−1/2, y, −z+1/2. |
Acknowledgements
The authors express their sincere thanks to Mr O. Yamate at Orient Chemical Industries, Ltd for the sample preparation.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Compound (I) is a charge-control-agent used for toners in electrophotography. The background of the present study has been set out in our previous paper (Uta et al., 2009). We have previously investigated the crystal structure of the following four isomers in connection with the mechanism of their high melting points: benzyltributylammonium 4-hydroxynaphthalene-1-sulfonate (Mizuguchi et al., 2007), benzyltributylammonium 6-hydroxynaphthalene-2-sulfonate (Uta et al., 2009, benzyltributylammonium 4-hydroxynaphthalene-2-sulfonate (Uta & Mizuguchi, 2009), and benzyltributylammonium 7-hydroxynaphthalene-1-sulfonate (Sato et al., 2009). The melting points of these isomers are 462, 433, 451 and 439 K, respectively. Except for benzyltributylammonium 4-hydroxynaphthalene-2-sulfonate, the anions in the ammonium sulfates form chains of O—H···O intermolecular hydrogen bonds between the –OH group of one anion and the sulfonic O atom of the neighboring one. The present hydrogen-bond network is found to be responsible for the high thermal stability of these compounds. On the other hand, benzyltributylammonium 4-hydroxynaphthalene-2-sulfonate which forms a two-dimensional hydrogen-bond network (Uta & Mizuguchi, 2009). The present paper deals with the structure of the title compound, (I), which includes two hydroxy groups in the naphthalene sulfonate (Fig. 1).
The ions in (I) have no crystallographically imposed symmetry. Fig. 2 shows a pseudo-dimer unit connected by O—H···O intermolecular hydrogen-bonded between the OH group of one anion and the sulfonic O atom of the neighboring one. Then, the dimer units consitute a two-dimensional hydrogen-bond network as shown in Fig. 3. There are four hydrogen bonds per molecule in the network, which contibutes to the high thermal stability of compound (I) as characterized by a melting point of 478 K.