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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 2| February 2009| Page o323
doi:10.1107/S160053680900018X

Benzyl­tri­butyl­ammonium 6,7-di­hydroxy­naphthalene-2-sulfonate

Kazuya Utaa and Jin Mizuguchia*

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

(Received 3 January 2009; accepted 4 January 2009; online 17 January 2009)

The title mol­ecular salt, C19H34N+·C10H7O5S−, is a charge-control agent used for toners in electrophotography. There are two formula units in the asymmetric unit. Both anions form inversion dimers connected by pairs of O—H⋯O hydrogen bonds between the –OH group of one anion and a sulfonic O atom of the neighboring one. The two dimers A and B are characterized by a step between the least-squares planes of the naphthalene atoms of 0.85 and 2.30 Å. Further O—H⋯O bonds link the dimers into a two-dimensional network propagating in (110) such that dimer A is hydrogen-bonded to four B units and vice versa. One of the tert-butyl chains in one of the cations is disordered over two sets of sites in a 0.56:0.44 ratio.

Related literature

For the function of charge-control agents, see: Nash et al. (2001[Nash, R. J., Grande, M. L. & Muller, R. N. (2001). Proceedings of the 7th International Conference on Advances in Non-Impact Printing Technology, pp. 358-364.]). For background and related structures, see: Mizuguchi et al. (2007[Mizuguchi, J., Sato, Y., Uta, K. & Sato, K. (2007). Acta Cryst. E63, o2509-o2510.]); Uta & Mizuguchi (2009a[Uta, K. & Mizuguchi, J. (2009a). Acta Cryst. E65, o320.],b[Uta, K. & Mizuguchi, J. (2009b). Acta Cryst. E65, o322.]); Sato et al. (2009[Sato, Y., Uta, K. & Mizuguchi, J. (2009). Acta Cryst. E65, o321.]); Uta et al. (2009[Uta, K., Sato, Y. & Mizuguchi, J. (2009). Acta Cryst. E65, o319.]).

[Scheme 1]

Experimental

Crystal data

  • C19H34N·C10H7O5S

  • Mr = 515.70

  • Triclinic, [P \overline 1]

  • a = 8.6720 (2) Å

  • b = 17.1110 (3) Å

  • c = 18.8201 (4) Å

  • α = 86.4785 (11)°

  • β = 83.9245 (12)°

  • γ = 85.4033 (11)°

  • V = 2764.08 (10) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 1.35 mm−1

  • T = 296.1 K

  • 0.38 × 0.33 × 0.15 mm
Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.650, Tmax = 0.817

  • 22714 measured reflections

  • 9189 independent reflections

  • 6913 reflections with F2 > 2σ(F2)

  • Rint = 0.038
Refinement

  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.211

  • S = 1.12

  • 9189 reflections

  • 659 parameters

  • H-atom parameters constrained

  • Δρmax = 0.61 e Å−3

  • Δρmin = −0.47 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O4—H4O⋯O3i 0.82 1.85 2.670 (3) 174
O5—H5O⋯O8ii 0.82 1.83 2.625 (3) 163
O9—H9O⋯O2 0.82 1.85 2.650 (3) 165
O10—H10O⋯O6iii 0.82 1.93 2.705 (3) 158
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x-1, y+1, z; (iii) -x+2, -y+1, -z.

Data collection: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2006[Rigaku/MSC (2006). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); program(s) used to solve structure: SIR2004 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory. Tennessee, USA.]); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks General, I. DOI: 10.1107/S160053680900018X/hb2892sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900018X/hb2892Isup2.hkl

checkCIF report


Comment top

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, 2009a), 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 was characterized by a hydrogen-bonded dimer of the anions through O—H···O hydrogen bonding. In addition to these isomers, we have newly studied a similar ammonium sulfonate which includes two hydroxy groups in the naphthalene sulfonate as in the title compound: benzyltributylammonium 4,6-dihydroxynaphthalene-2-sulfonate which forms a two-dimensional hydrogen-bond network (Uta & Mizuguchi, 2009b).

There are two independent molecules in the asymmetric unit. The ions have no crystallographically imposed symmetry. Both anions form inversion dimers (A: composed of two anions of C20—C21/S2/O1—O5; B: composed of two anions of C49—C58/S1/O6—O9) through O—H···O intermoleclar hydrogen bonds (Table 1) between the –OH group of one anion and the sulfonic O atom of the neighboring one (Figs. 2 and 4). Dimer units A and B are characterized by a step of about 0.85 and 2.30Å (Figs. 3 and 5, respectively). Then, units A and B constitute a two-dimentional O—H···O hydrogen-bond network. Unit A is hydrogen-bonded to four units B and vice versa, as shown in Fig. 6. The present network is quite similart to that of benzyltributylammonium 4,6-dihydroxynaphthalene-2-sulfonate (Uta & Mizuguchi, 2009b) and ensures a high thermal stability of compound (I) as characterized by a melting point of 478 K.

Related literature top

For the function of charge-control agents, see: Nash et al. (2001). For background and related structures, see: Mizuguchi et al. (2007); Uta & Mizuguchi (2009a,b); Sato et al. (2009); Uta et al. (2009).

Experimental top

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 of (I) were obtained in the form of plates.

Refinement top

C43 and C44 were found to be disordered over two sites each in a 0.56:0.44 ratio. 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).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 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/MSC, 2006).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), showing 30% probability displacement ellipsoids and only the major disorder components. H atoms are omitted for clarity.
[Figure 2] Fig. 2. Hydrogen-bonded dimer unit A: (top view). The molecules are related by the symmetry operation (1–x, 2–y, 1–z).
[Figure 3] Fig. 3. Hydrogen-bonded dimer unit A (side view).
[Figure 4] Fig. 4. Hydrogen-bonded dimer unit B: (top view). The molecules are related by the symmetry operation (1–x, 1–y, –z).
[Figure 5] Fig. 5. Hydrogen-bonded dimer unit B (side view).
[Figure 6] Fig. 6. Two-dimensional hydrogen-bond network. Unit A is hydrogen-bonded to four units B and vice versa.
(I) top
Crystal data top
C19H34N·C10H7O5SZ = 4
Mr = 515.70F(000) = 1112.00
Triclinic, P1Dx = 1.239 Mg m−3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54187 Å
a = 8.6720 (2) ÅCell parameters from 19472 reflections
b = 17.1110 (3) Åθ = 3.4–68.2°
c = 18.8201 (4) ŵ = 1.35 mm−1
α = 86.4785 (11)°T = 296 K
β = 83.9245 (12)°Plate, colourless
γ = 85.4033 (11)°0.38 × 0.33 × 0.15 mm
V = 2764.08 (10) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer		6913 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.038
ω scansθmax = 68.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −10→10
Tmin = 0.650, Tmax = 0.817k = −20→20
22714 measured reflectionsl = −22→22
9189 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.068 w = 1/[σ2(Fo2) + (0.0999P)2 + 1.4745P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.211(Δ/σ)max < 0.001
S = 1.12Δρmax = 0.61 e Å−3
9189 reflectionsΔρmin = −0.47 e Å−3
659 parameters
Crystal data top
C19H34N·C10H7O5Sγ = 85.4033 (11)°
Mr = 515.70V = 2764.08 (10) Å3
Triclinic, P1Z = 4
a = 8.6720 (2) ÅCu Kα radiation
b = 17.1110 (3) ŵ = 1.35 mm−1
c = 18.8201 (4) ÅT = 296 K
α = 86.4785 (11)°0.38 × 0.33 × 0.15 mm
β = 83.9245 (12)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		9189 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		6913 reflections with F2 > 2σ(F2)
Tmin = 0.650, Tmax = 0.817Rint = 0.038
22714 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.068659 parameters
wR(F2) = 0.211H-atom parameters constrained
S = 1.12Δρmax = 0.61 e Å−3
9189 reflectionsΔρmin = −0.47 e Å−3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S11.06446 (11)0.30094 (5)0.11704 (4)0.0569 (2)
S20.58851 (11)0.80242 (5)0.37619 (4)0.0604 (2)
O10.4657 (3)0.75257 (16)0.39950 (19)0.0995 (10)
O20.6913 (3)0.77255 (16)0.31646 (13)0.0838 (8)
O30.6737 (3)0.82138 (16)0.43377 (14)0.0904 (9)
O40.2201 (2)1.21344 (13)0.43914 (12)0.0658 (6)
O50.1545 (2)1.23589 (13)0.30645 (12)0.0664 (6)
O61.2260 (2)0.31041 (15)0.09176 (14)0.0737 (7)
O70.9746 (3)0.28047 (14)0.06196 (13)0.0738 (7)
O81.0478 (3)0.24769 (14)0.18053 (13)0.0783 (7)
O90.6544 (3)0.73906 (14)0.18398 (13)0.0732 (7)
O100.6797 (2)0.71063 (13)0.04788 (13)0.0702 (6)
N10.3094 (3)0.70872 (17)0.60694 (16)0.0627 (7)
N20.1740 (3)0.78694 (18)0.11548 (17)0.0662 (7)
C10.6084 (5)0.5710 (2)0.6532 (2)0.0953 (14)
C20.6471 (6)0.4967 (3)0.6813 (3)0.1109 (17)
C30.5748 (7)0.4337 (3)0.6631 (3)0.1093 (18)
C40.4656 (6)0.4441 (2)0.6158 (2)0.0959 (14)
C50.4267 (5)0.5184 (2)0.5869 (2)0.0814 (11)
C60.4952 (4)0.5832 (2)0.6058 (2)0.0729 (10)
C70.4579 (4)0.6643 (2)0.5736 (2)0.0713 (10)
C80.3072 (4)0.7096 (2)0.6879 (2)0.0726 (10)
C90.4293 (5)0.7555 (2)0.7149 (2)0.0913 (13)
C100.4066 (8)0.7511 (4)0.7975 (3)0.134 (2)
C110.4371 (8)0.6768 (4)0.8316 (3)0.146 (2)
C120.1647 (4)0.6689 (2)0.5951 (2)0.0719 (10)
C130.1264 (5)0.6646 (2)0.5198 (2)0.0882 (12)
C14−0.0225 (6)0.6144 (2)0.5252 (3)0.1162 (18)
C15−0.0912 (9)0.6129 (3)0.4583 (4)0.165 (3)
C160.3079 (4)0.7909 (2)0.5720 (2)0.0670 (9)
C170.1710 (4)0.8469 (2)0.5970 (2)0.0767 (11)
C180.1949 (5)0.9283 (2)0.5637 (2)0.0859 (12)
C190.0728 (6)0.9900 (2)0.5897 (3)0.1003 (15)
C200.5001 (3)0.89379 (18)0.34448 (16)0.0521 (7)
C210.4674 (4)0.90556 (19)0.27309 (17)0.0590 (8)
C220.3912 (4)0.9741 (2)0.25050 (17)0.0602 (8)
C230.3447 (3)1.03487 (18)0.29811 (16)0.0518 (7)
C240.2667 (4)1.10708 (19)0.27670 (17)0.0556 (8)
C250.2266 (3)1.16439 (18)0.32395 (17)0.0536 (7)
C260.2623 (3)1.15214 (18)0.39592 (16)0.0516 (7)
C270.3366 (3)1.08346 (18)0.41786 (16)0.0522 (7)
C280.3800 (3)1.02278 (17)0.37003 (16)0.0492 (7)
C290.4578 (3)0.95124 (18)0.39170 (16)0.0519 (7)
C30−0.1203 (5)0.9258 (2)0.1822 (2)0.0953 (14)
C31−0.1546 (6)1.0006 (3)0.2059 (3)0.1098 (16)
C32−0.0852 (6)1.0629 (3)0.1713 (3)0.1077 (17)
C330.0191 (6)1.0519 (2)0.1126 (3)0.1010 (15)
C340.0551 (5)0.9773 (2)0.0875 (2)0.0889 (12)
C35−0.0126 (4)0.9128 (2)0.1231 (2)0.0740 (10)
C360.0205 (4)0.8301 (2)0.0976 (2)0.0747 (10)
C370.1923 (5)0.7879 (2)0.1945 (2)0.0801 (11)
C380.0830 (6)0.7426 (2)0.2445 (2)0.0954 (14)
C390.1169 (8)0.7492 (3)0.3230 (2)0.129 (2)
C400.0779 (6)0.8273 (3)0.3513 (2)0.1071 (16)
C410.3142 (5)0.8264 (2)0.0779 (2)0.0894 (12)
C420.3321 (6)0.8312 (3)−0.0018 (3)0.1211 (16)
C43A0.4120 (10)0.8997 (5)−0.0503 (6)0.121 (2)0.56
C43B0.4814 (11)0.8811 (7)−0.0068 (6)0.121 (2)0.44
C44A0.5731 (11)0.8811 (7)−0.0371 (7)0.135 (3)0.56
C44B0.5504 (18)0.8968 (10)−0.0794 (7)0.135 (3)0.44
C450.1714 (4)0.7040 (2)0.0916 (2)0.0675 (9)
C460.3091 (4)0.6478 (2)0.1063 (2)0.0774 (11)
C470.2877 (5)0.5676 (2)0.0830 (3)0.0982 (15)
C480.4076 (6)0.5046 (2)0.1005 (3)0.1076 (16)
C490.9868 (3)0.39446 (18)0.14593 (16)0.0508 (7)
C500.9904 (4)0.4139 (2)0.21721 (17)0.0595 (8)
C510.9259 (4)0.4844 (2)0.23940 (17)0.0633 (9)
C520.8575 (3)0.54087 (19)0.19191 (16)0.0522 (7)
C530.7862 (4)0.6136 (2)0.21372 (17)0.0586 (8)
C540.7252 (3)0.66777 (19)0.16591 (17)0.0546 (7)
C550.7366 (3)0.65187 (19)0.09207 (17)0.0531 (7)
C560.7997 (3)0.58110 (19)0.07014 (16)0.0530 (7)
C570.8606 (3)0.52288 (18)0.11910 (16)0.0495 (7)
C580.9237 (3)0.44814 (19)0.09809 (16)0.0537 (7)
H10.65920.61390.66540.113*
H20.72750.48980.71250.140*
H30.59520.38310.68330.133*
H40.41800.40140.60240.116*
H4O0.24641.20170.47920.079*
H50.35460.52520.55360.099*
H5O0.14021.23830.26400.080*
H7A0.45010.66030.52310.088*
H7B0.54560.69520.57800.088*
H8A0.31940.65520.70670.088*
H8B0.20470.73060.70700.088*
H9A0.41890.81010.69720.112*
H9B0.53340.73400.69790.112*
H9O0.65470.74350.22710.088*
H10A0.47500.78620.81540.164*
H10B0.30150.76860.81350.164*
H10O0.68940.69640.00670.084*
H11A0.42290.68080.88270.211*
H11B0.54330.65780.81780.211*
H11C0.36820.64100.81770.211*
H12A0.17470.61530.61590.089*
H12B0.07590.69550.62180.089*
H13A0.21310.63880.49150.108*
H13B0.10440.71680.49920.108*
H14A0.00520.56180.54260.141*
H14B−0.10220.63780.55950.141*
H15A−0.17720.58170.46420.261*
H15B−0.01120.58790.42330.261*
H15C−0.11780.66430.44000.261*
H16A0.30990.78690.52060.081*
H16B0.40390.81330.58030.081*
H17A0.16300.84890.64880.093*
H17B0.07580.82930.58380.093*
H18A0.29600.94400.57310.103*
H18B0.19670.92710.51170.103*
H19A0.09451.04050.56570.154*
H19B0.07170.99380.64000.154*
H19C−0.02750.97690.57840.154*
H210.49680.86670.24050.072*
H220.36880.98090.20310.074*
H240.24211.11550.22980.067*
H270.35821.07610.46540.065*
H290.48070.94300.43910.063*
H30−0.16740.88270.20630.114*
H31−0.22771.00970.24460.136*
H32−0.10711.11310.18730.134*
H330.06791.09460.08920.125*
H340.12380.96970.04630.109*
H36A0.01810.83240.04650.088*
H36B−0.06390.79910.11870.088*
H37A0.18200.84180.20770.095*
H37B0.29770.76720.20160.095*
H38A0.09310.68780.23340.117*
H38B−0.02300.76290.23960.117*
H39A0.05730.71090.35250.156*
H39B0.22550.73430.32610.156*
H40A0.10390.82780.39880.162*
H40B−0.03300.84140.35030.162*
H40C0.13320.86590.32110.162*
H41A0.31090.87960.09370.106*
H41B0.40810.79870.09400.106*
H42A0.22830.8302−0.01630.145*0.56
H42B0.38840.7825−0.01620.145*0.56
H42C0.24430.8594−0.02210.145*0.44
H42D0.35420.7802−0.02210.145*0.44
H43A0.39750.8966−0.10040.145*0.56
H43B0.37350.9512−0.03450.145*0.56
H43C0.45180.93060.01500.145*0.44
H43D0.55900.85280.02050.145*0.44
H44A0.60630.8293−0.05210.202*0.56
H44B0.58260.88330.01310.202*0.56
H44C0.63690.9185−0.06350.202*0.56
H44D0.64630.9209−0.07830.202*0.44
H44E0.48010.9314−0.10490.202*0.44
H44F0.57050.8483−0.10320.202*0.44
H45A0.16220.70660.04060.082*
H45B0.07830.68140.11520.082*
H46A0.40340.66710.08020.095*
H46B0.32300.64540.15690.095*
H47A0.18670.55110.10520.123*
H47B0.28220.56960.03160.123*
H48A0.38680.45580.08360.163*
H48B0.41080.49940.15200.163*
H48C0.50840.51940.07920.163*
H501.03930.37890.24920.072*
H510.92810.49570.28700.077*
H530.78030.62500.26190.072*
H560.80510.57140.02190.066*
H580.91960.43490.05150.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0768 (5)0.0443 (4)0.0498 (4)0.0076 (3)−0.0151 (3)−0.0049 (3)
S20.0794 (6)0.0453 (4)0.0546 (4)0.0155 (4)−0.0090 (4)−0.0117 (3)
O10.102 (2)0.0561 (16)0.133 (2)0.0040 (15)0.0016 (19)0.0149 (16)
O20.105 (2)0.0779 (17)0.0630 (14)0.0423 (15)−0.0065 (13)−0.0240 (12)
O30.135 (2)0.0674 (16)0.0721 (16)0.0379 (16)−0.0467 (16)−0.0252 (13)
O40.0897 (17)0.0481 (12)0.0592 (13)0.0168 (11)−0.0166 (11)−0.0132 (10)
O50.0882 (17)0.0492 (12)0.0586 (13)0.0190 (11)−0.0112 (11)−0.0022 (10)
O60.0719 (16)0.0735 (16)0.0750 (16)0.0124 (13)−0.0089 (12)−0.0193 (12)
O70.1001 (19)0.0590 (14)0.0665 (15)0.0061 (13)−0.0287 (13)−0.0181 (11)
O80.128 (2)0.0514 (13)0.0545 (13)0.0067 (14)−0.0172 (14)0.0034 (10)
O90.0933 (18)0.0566 (14)0.0659 (14)0.0228 (13)−0.0050 (12)−0.0144 (11)
O100.0866 (17)0.0588 (14)0.0599 (13)0.0240 (12)−0.0065 (12)−0.0014 (11)
N10.0625 (17)0.0519 (16)0.0715 (18)−0.0035 (14)0.0046 (13)−0.0049 (13)
N20.0636 (18)0.0604 (17)0.0773 (19)−0.0029 (14)−0.0155 (14)−0.0125 (14)
C10.089 (3)0.078 (3)0.117 (3)0.014 (2)−0.020 (2)−0.010 (2)
C20.109 (4)0.098 (3)0.121 (4)0.032 (3)−0.025 (3)−0.002 (3)
C30.119 (4)0.077 (3)0.119 (4)0.032 (3)0.008 (3)0.012 (2)
C40.107 (3)0.056 (2)0.117 (3)0.016 (2)0.006 (3)−0.010 (2)
C50.087 (2)0.064 (2)0.090 (2)0.011 (2)−0.000 (2)−0.013 (2)
C60.074 (2)0.061 (2)0.078 (2)0.0080 (19)0.0072 (19)−0.0026 (18)
C70.064 (2)0.062 (2)0.082 (2)0.0061 (18)0.0124 (18)−0.0014 (18)
C80.080 (2)0.064 (2)0.072 (2)−0.009 (2)0.0058 (19)−0.0076 (18)
C90.107 (3)0.087 (3)0.083 (2)−0.023 (2)−0.011 (2)−0.006 (2)
C100.169 (6)0.125 (5)0.118 (4)−0.029 (4)−0.039 (4)−0.014 (3)
C110.175 (6)0.142 (5)0.134 (5)−0.025 (4)−0.077 (4)0.020 (4)
C120.065 (2)0.055 (2)0.094 (2)−0.0046 (18)0.0016 (19)−0.0078 (19)
C130.097 (3)0.062 (2)0.108 (3)0.001 (2)−0.028 (2)−0.010 (2)
C140.130 (4)0.064 (2)0.162 (5)−0.008 (2)−0.048 (4)−0.007 (3)
C150.172 (6)0.099 (4)0.241 (9)−0.007 (4)−0.108 (6)−0.006 (5)
C160.066 (2)0.0498 (19)0.082 (2)−0.0026 (17)0.0060 (18)−0.0016 (17)
C170.076 (2)0.054 (2)0.097 (2)0.0012 (19)0.003 (2)−0.0078 (19)
C180.082 (2)0.061 (2)0.111 (3)0.002 (2)0.005 (2)−0.002 (2)
C190.110 (3)0.063 (2)0.123 (3)0.009 (2)0.000 (3)−0.009 (2)
C200.0615 (19)0.0443 (17)0.0499 (16)0.0054 (14)−0.0075 (14)−0.0057 (13)
C210.074 (2)0.0485 (18)0.0543 (18)0.0084 (16)−0.0073 (15)−0.0139 (14)
C220.078 (2)0.0541 (19)0.0474 (17)0.0077 (17)−0.0095 (15)−0.0081 (14)
C230.0612 (19)0.0469 (17)0.0473 (16)0.0009 (14)−0.0068 (13)−0.0060 (13)
C240.067 (2)0.0483 (17)0.0503 (17)0.0040 (15)−0.0086 (14)−0.0015 (13)
C250.0591 (19)0.0440 (17)0.0568 (18)0.0039 (14)−0.0082 (14)−0.0003 (13)
C260.0606 (19)0.0427 (16)0.0505 (16)0.0046 (14)−0.0041 (13)−0.0083 (13)
C270.0626 (19)0.0447 (16)0.0485 (16)0.0063 (14)−0.0080 (14)−0.0062 (13)
C280.0548 (18)0.0424 (16)0.0496 (16)0.0036 (14)−0.0048 (13)−0.0052 (12)
C290.0625 (19)0.0439 (16)0.0491 (16)0.0053 (14)−0.0085 (13)−0.0074 (13)
C300.086 (3)0.071 (2)0.123 (3)0.009 (2)0.009 (2)−0.010 (2)
C310.110 (4)0.084 (3)0.132 (4)0.011 (3)0.004 (3)−0.025 (3)
C320.101 (3)0.066 (3)0.158 (5)0.013 (2)−0.028 (3)−0.019 (3)
C330.095 (3)0.061 (2)0.146 (4)−0.000 (2)−0.021 (3)0.006 (2)
C340.088 (3)0.071 (2)0.104 (3)0.005 (2)−0.010 (2)0.006 (2)
C350.070 (2)0.061 (2)0.093 (2)0.0008 (19)−0.018 (2)−0.005 (2)
C360.068 (2)0.072 (2)0.086 (2)0.0037 (19)−0.0206 (19)−0.011 (2)
C370.087 (2)0.072 (2)0.086 (2)0.001 (2)−0.027 (2)−0.023 (2)
C380.128 (4)0.075 (2)0.083 (2)−0.006 (2)−0.007 (2)−0.018 (2)
C390.206 (6)0.100 (3)0.080 (3)0.035 (4)−0.036 (3)−0.013 (2)
C400.120 (4)0.109 (3)0.090 (3)0.016 (3)−0.004 (2)−0.029 (2)
C410.072 (2)0.062 (2)0.132 (3)−0.010 (2)0.003 (2)−0.013 (2)
C420.123 (3)0.091 (3)0.136 (3)−0.010 (2)0.045 (3)−0.001 (2)
C43A0.116 (4)0.094 (4)0.141 (5)−0.000 (3)0.026 (3)0.011 (3)
C43B0.116 (4)0.094 (4)0.141 (5)−0.000 (3)0.026 (3)0.011 (3)
C44A0.115 (4)0.115 (6)0.159 (7)−0.004 (4)0.030 (5)0.041 (6)
C44B0.115 (4)0.115 (6)0.159 (7)−0.004 (4)0.030 (5)0.041 (6)
C450.071 (2)0.060 (2)0.074 (2)−0.0047 (18)−0.0136 (18)−0.0160 (17)
C460.074 (2)0.065 (2)0.096 (2)0.001 (2)−0.016 (2)−0.018 (2)
C470.091 (3)0.068 (2)0.140 (4)0.002 (2)−0.026 (2)−0.028 (2)
C480.113 (4)0.070 (2)0.140 (4)0.003 (2)−0.019 (3)−0.016 (2)
C490.0613 (19)0.0457 (17)0.0454 (15)0.0009 (14)−0.0073 (13)−0.0057 (12)
C500.077 (2)0.0514 (18)0.0494 (17)0.0053 (16)−0.0125 (15)−0.0016 (14)
C510.086 (2)0.061 (2)0.0434 (16)0.0049 (18)−0.0112 (16)−0.0067 (14)
C520.0586 (19)0.0503 (18)0.0473 (16)−0.0008 (15)−0.0040 (13)−0.0058 (13)
C530.070 (2)0.0566 (19)0.0483 (17)0.0015 (16)−0.0030 (14)−0.0108 (14)
C540.0562 (19)0.0487 (18)0.0573 (18)0.0043 (15)−0.0000 (14)−0.0099 (14)
C550.0569 (18)0.0491 (17)0.0521 (17)0.0045 (14)−0.0063 (13)−0.0028 (13)
C560.0609 (19)0.0517 (18)0.0449 (16)0.0076 (15)−0.0069 (13)−0.0048 (13)
C570.0529 (17)0.0491 (17)0.0457 (15)0.0014 (14)−0.0051 (12)−0.0041 (12)
C580.066 (2)0.0505 (18)0.0443 (16)0.0042 (15)−0.0085 (14)−0.0058 (13)
Geometric parameters (Å, º) top
S1—O61.450 (2)C4—H40.929
S1—O71.437 (2)C5—H50.927
S1—O81.459 (2)C7—H7A0.967
S1—C491.779 (3)C7—H7B0.974
S2—O11.433 (3)C8—H8A0.977
S2—O21.451 (2)C8—H8B0.972
S2—O31.441 (3)C9—H9A0.973
S2—C201.783 (3)C9—H9B0.976
O4—C261.370 (3)C10—H10A0.976
O5—C251.366 (3)C10—H10B0.959
O9—C541.367 (3)C11—H11A0.962
O10—C551.361 (3)C11—H11B0.966
N1—C71.536 (4)C11—H11C0.955
N1—C81.523 (5)C12—H12A0.974
N1—C121.517 (5)C12—H12B0.971
N1—C161.514 (4)C13—H13A0.967
N2—C361.529 (4)C13—H13B0.965
N2—C371.514 (5)C14—H14A0.960
N2—C411.525 (5)C14—H14B0.974
N2—C451.517 (4)C15—H15A0.945
C1—C21.377 (7)C15—H15B0.994
C1—C61.391 (6)C15—H15C0.945
C2—C31.368 (8)C16—H16A0.972
C3—C41.361 (8)C16—H16B0.975
C4—C51.382 (6)C17—H17A0.973
C5—C61.381 (6)C17—H17B0.962
C6—C71.503 (5)C18—H18A0.975
C8—C91.514 (6)C18—H18B0.978
C9—C101.544 (8)C19—H19A0.972
C10—C111.407 (9)C19—H19B0.950
C12—C131.497 (6)C19—H19C0.964
C13—C141.598 (7)C21—H210.934
C14—C151.451 (10)C22—H220.931
C16—C171.518 (5)C24—H240.929
C17—C181.512 (5)C27—H270.932
C18—C191.500 (6)C29—H290.934
C20—C211.402 (4)C30—H300.940
C20—C291.368 (4)C31—H310.926
C21—C221.367 (4)C32—H320.925
C22—C231.420 (4)C33—H330.937
C23—C241.418 (4)C34—H340.935
C23—C281.418 (4)C36—H36A0.963
C24—C251.364 (4)C36—H36B0.975
C25—C261.421 (4)C37—H37A0.965
C26—C271.357 (4)C37—H37B0.973
C27—C281.418 (4)C38—H38A0.968
C28—C291.409 (4)C38—H38B0.968
C30—C311.381 (7)C39—H39A0.976
C30—C351.392 (6)C39—H39B0.963
C31—C321.363 (7)C40—H40A0.946
C32—C331.364 (8)C40—H40B0.975
C33—C341.390 (6)C40—H40C0.969
C34—C351.393 (6)C41—H41A0.972
C35—C361.517 (5)C41—H41B0.977
C37—C381.491 (6)C42—H42A0.970
C38—C391.549 (7)C42—H42B0.970
C39—C401.470 (7)C42—H42C0.970
C41—C421.488 (7)C42—H42D0.970
C42—C43A1.598 (10)C43A—H43A0.970
C42—C43B1.598 (13)C43A—H43B0.970
C43A—C44A1.451 (13)C43B—H43C0.970
C43B—C44B1.451 (17)C43B—H43D0.970
C45—C461.511 (5)C44A—H44A0.960
C46—C471.496 (6)C44A—H44B0.960
C47—C481.485 (6)C44A—H44C0.960
C49—C501.406 (4)C44B—H44D0.960
C49—C581.370 (4)C44B—H44E0.960
C50—C511.360 (4)C44B—H44F0.960
C51—C521.413 (4)C45—H45A0.970
C52—C531.409 (4)C45—H45B0.975
C52—C571.420 (4)C46—H46A0.978
C53—C541.367 (4)C46—H46B0.971
C54—C551.424 (4)C47—H47A0.984
C55—C561.358 (4)C47—H47B0.973
C56—C571.423 (4)C48—H48A0.949
C57—C581.413 (4)C48—H48B0.971
O4—H4O0.820C48—H48C0.969
O5—H5O0.820C50—H500.931
O9—H9O0.820C51—H510.931
O10—H10O0.820C53—H530.934
C1—H10.938C56—H560.928
C2—H20.954C58—H580.924
C3—H30.935
O2···O92.650 (3)O6···H11Bviii2.864
O3···O4i2.670 (3)O6···H44Aiii2.797
O4···O3i2.670 (3)O6···H48Avi2.936
O5···O8ii2.625 (3)O6···H56iii2.871
O6···O10iii2.705 (3)O7···H36Aix2.887
O8···O5iv2.625 (3)O7···H42Aix2.911
O9···O22.650 (3)O7···H45Aix2.360
O10···O6iii2.705 (3)O8···H5Oiv1.830
S1···H10Oiii2.989O8···H8Bv2.897
O1···H3v2.985O8···H24iv2.877
O1···H4v2.745O8···H32iv2.748
O1···H7A2.727O9···H212.696
O1···H16A2.598O9···H36Bvi2.854
O1···H39B2.666O9···H41B2.945
O2···H9O1.849O10···H41B2.780
O2···H30vi2.950O10···H43D2.614
O2···H38Bvi2.731O10···H44A2.765
O2···H40Bvi2.893O10···H46A2.567
O2···H532.804C15···H39A2.798
O3···H4Oi1.853C25···H9Bi2.799
O3···H27i2.641C25···H17Bvii2.986
O3···H40Bvi2.878C26···H17Bvii2.911
O4···H7Bi2.643C27···H16Bi2.975
O4···H14Bvii2.666C27···H19Cvii2.941
O4···H17Bvii2.807C33···H44Dx2.973
O5···H9Bi2.787C44B···H10Axi2.976
O5···H12Bvii2.538C55···H46A2.912
O5···H17Bvii2.950C56···H48C2.800
O5···H50ii2.768C57···H47Avi2.889
O6···H10Oiii1.927
O6—S1—O7113.17 (15)C14—C13—H13A110.7
O6—S1—O8112.23 (16)C14—C13—H13B111.4
O6—S1—C49105.71 (15)H13A—C13—H13B109.3
O7—S1—O8112.32 (16)C13—C14—H14A109.3
O7—S1—C49107.42 (15)C13—C14—H14B108.5
O8—S1—C49105.34 (14)C15—C14—H14A109.9
O1—S2—O2112.94 (18)C15—C14—H14B106.9
O1—S2—O3112.85 (19)H14A—C14—H14B108.2
O1—S2—C20107.19 (16)C14—C15—H15A110.4
O2—S2—O3111.74 (17)C14—C15—H15B107.3
O2—S2—C20106.23 (14)C14—C15—H15C111.0
O3—S2—C20105.25 (15)H15A—C15—H15B107.9
C7—N1—C8111.3 (2)H15A—C15—H15C112.2
C7—N1—C12111.7 (2)H15B—C15—H15C107.9
C7—N1—C16105.9 (2)N1—C16—H16A108.4
C8—N1—C12104.8 (2)N1—C16—H16B108.1
C8—N1—C16111.7 (2)C17—C16—H16A108.6
C12—N1—C16111.5 (2)C17—C16—H16B108.8
C36—N2—C37111.3 (2)H16A—C16—H16B106.8
C36—N2—C41111.9 (2)C16—C17—H17A109.7
C36—N2—C45106.1 (2)C16—C17—H17B110.2
C37—N2—C41105.0 (3)C18—C17—H17A108.9
C37—N2—C45111.8 (2)C18—C17—H17B109.7
C41—N2—C45110.8 (2)H17A—C17—H17B108.6
C2—C1—C6120.6 (4)C17—C18—H18A109.8
C1—C2—C3120.6 (5)C17—C18—H18B109.2
C2—C3—C4119.8 (5)C19—C18—H18A108.3
C3—C4—C5120.0 (4)C19—C18—H18B108.6
C4—C5—C6121.2 (4)H18A—C18—H18B106.6
C1—C6—C5117.7 (3)C18—C19—H19A109.7
C1—C6—C7119.9 (3)C18—C19—H19B110.2
C5—C6—C7122.2 (3)C18—C19—H19C109.5
N1—C7—C6116.1 (3)H19A—C19—H19B109.3
N1—C8—C9115.9 (3)H19A—C19—H19C108.1
C8—C9—C10108.4 (4)H19B—C19—H19C110.0
C9—C10—C11116.4 (5)C20—C21—H21120.5
N1—C12—C13117.9 (3)C22—C21—H21119.3
C12—C13—C14105.6 (3)C21—C22—H22119.3
C13—C14—C15113.9 (4)C23—C22—H22119.5
N1—C16—C17115.8 (2)C23—C24—H24119.6
C16—C17—C18109.6 (3)C25—C24—H24119.4
C17—C18—C19114.1 (3)C26—C27—H27119.1
S2—C20—C21120.7 (2)C28—C27—H27119.8
S2—C20—C29119.0 (2)C20—C29—H29119.6
C21—C20—C29120.2 (2)C28—C29—H29119.4
C20—C21—C22120.2 (2)C31—C30—H30120.8
C21—C22—C23121.2 (3)C35—C30—H30118.9
C22—C23—C24123.0 (2)C30—C31—H31120.7
C22—C23—C28118.2 (2)C32—C31—H31118.6
C24—C23—C28118.8 (2)C31—C32—H32120.8
C23—C24—C25121.0 (2)C33—C32—H32119.1
O5—C25—C24124.0 (2)C32—C33—H33120.2
O5—C25—C26116.0 (2)C34—C33—H33119.4
C24—C25—C26120.1 (2)C33—C34—H34120.7
O4—C26—C25116.0 (2)C35—C34—H34119.2
O4—C26—C27123.9 (2)N2—C36—H36A108.5
C25—C26—C27120.1 (2)N2—C36—H36B108.0
C26—C27—C28121.2 (2)C35—C36—H36A108.3
C23—C28—C27118.8 (2)C35—C36—H36B107.8
C23—C28—C29119.2 (2)H36A—C36—H36B107.5
C27—C28—C29122.0 (2)N2—C37—H37A108.3
C20—C29—C28121.0 (2)N2—C37—H37B107.7
C31—C30—C35120.3 (4)C38—C37—H37A108.3
C30—C31—C32120.7 (5)C38—C37—H37B107.8
C31—C32—C33120.1 (5)H37A—C37—H37B107.4
C32—C33—C34120.4 (4)C37—C38—H38A110.2
C33—C34—C35120.1 (4)C37—C38—H38B109.8
C30—C35—C34118.3 (3)C39—C38—H38A109.0
C30—C35—C36119.1 (3)C39—C38—H38B108.8
C34—C35—C36122.5 (3)H38A—C38—H38B108.3
N2—C36—C35116.5 (3)C38—C39—H39A107.5
N2—C37—C38116.9 (3)C38—C39—H39B108.1
C37—C38—C39110.7 (4)C40—C39—H39A109.0
C38—C39—C40114.8 (4)C40—C39—H39B109.5
N2—C41—C42117.6 (4)H39A—C39—H39B107.7
C41—C42—C43A124.7 (5)C39—C40—H40A110.7
C41—C42—C43B93.5 (5)C39—C40—H40B109.7
C42—C43A—C44A100.0 (7)C39—C40—H40C109.5
C42—C43B—C44B113.8 (10)H40A—C40—H40B109.4
N2—C45—C46116.6 (3)H40A—C40—H40C109.9
C45—C46—C47110.8 (3)H40B—C40—H40C107.6
C46—C47—C48116.5 (4)N2—C41—H41A108.5
S1—C49—C50120.6 (2)N2—C41—H41B108.2
S1—C49—C58119.6 (2)C42—C41—H41A107.6
C50—C49—C58119.8 (2)C42—C41—H41B107.9
C49—C50—C51120.2 (3)H41A—C41—H41B106.6
C50—C51—C52121.7 (3)C41—C42—H42A106.2
C51—C52—C53123.0 (2)C41—C42—H42B106.1
C51—C52—C57118.2 (2)C41—C42—H42C113.0
C53—C52—C57118.9 (2)C41—C42—H42D113.0
C52—C53—C54121.4 (2)C43A—C42—H42A106.1
O9—C54—C53124.0 (2)C43A—C42—H42B106.2
O9—C54—C55116.2 (2)C43B—C42—H42C113.0
C53—C54—C55119.9 (2)C43B—C42—H42D113.0
O10—C55—C54115.8 (2)H42A—C42—H42B106.4
O10—C55—C56124.4 (2)H42C—C42—H42D110.4
C54—C55—C56119.8 (2)C42—C43A—H43A111.8
C55—C56—C57121.4 (2)C42—C43A—H43B111.8
C52—C57—C56118.5 (2)C44A—C43A—H43A111.8
C52—C57—C58118.9 (2)C44A—C43A—H43B111.8
C56—C57—C58122.6 (2)H43A—C43A—H43B109.5
C49—C58—C57121.2 (2)C42—C43B—H43C108.8
C26—O4—H4O109.5C42—C43B—H43D108.8
C25—O5—H5O109.5C44B—C43B—H43C108.8
C54—O9—H9O109.5C44B—C43B—H43D108.8
C55—O10—H10O109.5H43C—C43B—H43D107.7
C2—C1—H1120.2C43A—C44A—H44A109.5
C6—C1—H1119.2C43A—C44A—H44B109.5
C1—C2—H2118.7C43A—C44A—H44C109.5
C3—C2—H2120.7H44A—C44A—H44B109.5
C2—C3—H3122.2H44A—C44A—H44C109.5
C4—C3—H3118.0H44B—C44A—H44C109.5
C3—C4—H4120.2C43B—C44B—H44D109.5
C5—C4—H4119.8C43B—C44B—H44E109.5
C4—C5—H5119.9C43B—C44B—H44F109.5
C6—C5—H5118.8H44D—C44B—H44E109.5
N1—C7—H7A108.8H44D—C44B—H44F109.5
N1—C7—H7B108.4H44E—C44B—H44F109.5
C6—C7—H7A108.3N2—C45—H45A108.6
C6—C7—H7B107.6N2—C45—H45B108.5
H7A—C7—H7B107.3C46—C45—H45A108.2
N1—C8—H8A107.7C46—C45—H45B107.6
N1—C8—H8B108.1H45A—C45—H45B107.0
C9—C8—H8A108.9C45—C46—H46A109.3
C9—C8—H8B109.1C45—C46—H46B109.9
H8A—C8—H8B106.8C47—C46—H46A109.2
C8—C9—H9A110.5C47—C46—H46B110.1
C8—C9—H9B110.5H46A—C46—H46B107.5
C10—C9—H9A109.4C46—C47—H47A108.8
C10—C9—H9B110.4C46—C47—H47B109.8
H9A—C9—H9B107.7C48—C47—H47A107.2
C9—C10—H10A109.2C48—C47—H47B107.8
C9—C10—H10B109.6H47A—C47—H47B106.2
C11—C10—H10A106.5C47—C48—H48A111.5
C11—C10—H10B107.0C47—C48—H48B109.3
H10A—C10—H10B107.7C47—C48—H48C108.9
C10—C11—H11A109.8H48A—C48—H48B109.5
C10—C11—H11B109.5H48A—C48—H48C109.7
C10—C11—H11C109.5H48B—C48—H48C107.8
H11A—C11—H11B108.8C49—C50—H50120.1
H11A—C11—H11C109.7C51—C50—H50119.7
H11B—C11—H11C109.4C50—C51—H51118.8
N1—C12—H12A108.1C52—C51—H51119.5
N1—C12—H12B108.4C52—C53—H53119.3
C13—C12—H12A107.5C54—C53—H53119.3
C13—C12—H12B107.6C55—C56—H56118.7
H12A—C12—H12B106.8C57—C56—H56119.8
C12—C13—H13A109.8C49—C58—H58119.6
C12—C13—H13B109.9C57—C58—H58119.2
O6—S1—C49—C50−90.7 (3)C22—C23—C28—C27178.9 (3)
O6—S1—C49—C5889.0 (3)C22—C23—C28—C29−0.6 (4)
O7—S1—C49—C50148.2 (2)C24—C23—C28—C27−0.3 (4)
O7—S1—C49—C58−32.1 (3)C24—C23—C28—C29−179.9 (3)
O8—S1—C49—C5028.3 (3)C28—C23—C24—C250.4 (4)
O8—S1—C49—C58−152.0 (2)C23—C24—C25—O5178.4 (3)
O1—S2—C20—C21−87.9 (3)C23—C24—C25—C26−0.3 (4)
O1—S2—C20—C2989.1 (3)O5—C25—C26—O40.1 (3)
O2—S2—C20—C2133.1 (3)O5—C25—C26—C27−178.7 (2)
O2—S2—C20—C29−149.9 (2)C24—C25—C26—O4178.9 (3)
O3—S2—C20—C21151.8 (2)C24—C25—C26—C270.1 (3)
O3—S2—C20—C29−31.3 (3)O4—C26—C27—C28−178.7 (2)
C7—N1—C8—C966.4 (4)C25—C26—C27—C28−0.0 (4)
C8—N1—C7—C651.8 (4)C26—C27—C28—C230.1 (3)
C7—N1—C12—C13−64.1 (3)C26—C27—C28—C29179.7 (3)
C12—N1—C7—C6−65.0 (4)C23—C28—C29—C200.2 (4)
C7—N1—C16—C17−179.5 (3)C27—C28—C29—C20−179.3 (3)
C16—N1—C7—C6173.4 (3)C31—C30—C35—C34−2.0 (7)
C8—N1—C12—C13175.2 (3)C31—C30—C35—C36−178.9 (4)
C12—N1—C8—C9−172.7 (3)C35—C30—C31—C320.8 (8)
C8—N1—C16—C17−58.1 (4)C30—C31—C32—C330.1 (7)
C16—N1—C8—C9−51.8 (4)C31—C32—C33—C340.3 (7)
C12—N1—C16—C1758.8 (4)C32—C33—C34—C35−1.6 (8)
C16—N1—C12—C1354.2 (4)C33—C34—C35—C302.4 (7)
C36—N2—C37—C3867.2 (4)C33—C34—C35—C36179.2 (4)
C37—N2—C36—C3552.3 (4)C30—C35—C36—N2−104.5 (4)
C36—N2—C41—C42−61.7 (4)C34—C35—C36—N278.8 (5)
C41—N2—C36—C35−64.9 (4)N2—C37—C38—C39179.8 (3)
C36—N2—C45—C46−177.6 (3)C37—C38—C39—C4069.5 (6)
C45—N2—C36—C35174.1 (3)N2—C41—C42—C43A149.6 (5)
C37—N2—C41—C42177.4 (3)N2—C41—C42—C43B176.0 (5)
C41—N2—C37—C38−171.5 (3)C41—C42—C43A—C44A70.8 (9)
C37—N2—C45—C46−56.1 (4)C41—C42—C43B—C44B176.3 (10)
C45—N2—C37—C38−51.3 (4)N2—C45—C46—C47177.5 (3)
C41—N2—C45—C4660.7 (4)C45—C46—C47—C48−174.4 (4)
C45—N2—C41—C4256.5 (4)S1—C49—C50—C51−177.7 (2)
C2—C1—C6—C5−1.6 (6)S1—C49—C58—C57179.8 (2)
C2—C1—C6—C7−178.0 (4)C50—C49—C58—C57−0.5 (5)
C6—C1—C2—C3−0.0 (7)C58—C49—C50—C512.7 (5)
C1—C2—C3—C41.2 (8)C49—C50—C51—C52−1.7 (5)
C2—C3—C4—C5−0.7 (8)C50—C51—C52—C53178.3 (3)
C3—C4—C5—C6−0.9 (7)C50—C51—C52—C57−1.4 (5)
C4—C5—C6—C12.1 (6)C51—C52—C53—C54178.1 (3)
C4—C5—C6—C7178.4 (4)C51—C52—C57—C56−176.6 (3)
C1—C6—C7—N1−101.7 (4)C51—C52—C57—C583.4 (4)
C5—C6—C7—N182.0 (4)C53—C52—C57—C563.8 (4)
N1—C8—C9—C10178.8 (3)C53—C52—C57—C58−176.2 (3)
C8—C9—C10—C1167.1 (7)C57—C52—C53—C54−2.3 (5)
N1—C12—C13—C14175.9 (3)C52—C53—C54—O9179.8 (3)
C12—C13—C14—C15171.8 (4)C52—C53—C54—C55−1.6 (5)
N1—C16—C17—C18173.7 (3)O9—C54—C55—O101.9 (4)
C16—C17—C18—C19−175.0 (4)O9—C54—C55—C56−177.3 (3)
S2—C20—C21—C22176.1 (2)C53—C54—C55—O10−176.9 (3)
S2—C20—C29—C28−176.5 (2)C53—C54—C55—C563.9 (5)
C21—C20—C29—C280.5 (5)O10—C55—C56—C57178.5 (3)
C29—C20—C21—C22−0.8 (5)C54—C55—C56—C57−2.4 (5)
C20—C21—C22—C230.4 (5)C55—C56—C57—C52−1.5 (4)
C21—C22—C23—C24179.5 (3)C55—C56—C57—C58178.5 (3)
C21—C22—C23—C280.3 (5)C52—C57—C58—C49−2.6 (4)
C22—C23—C24—C25−178.8 (3)C56—C57—C58—C49177.5 (3)
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, y+1, z; (iii) −x+2, −y+1, −z; (iv) x+1, y−1, z; (v) −x+1, −y+1, −z+1; (vi) x+1, y, z; (vii) −x, −y+2, −z+1; (viii) −x+2, −y+1, −z+1; (ix) −x+1, −y+1, −z; (x) −x+1, −y+2, −z; (xi) x, y, z−1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4O···O3i0.821.852.670 (3)174
O5—H5O···O8ii0.821.832.625 (3)163
O9—H9O···O20.821.852.650 (3)165
O10—H10O···O6iii0.821.932.705 (3)158
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, y+1, z; (iii) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formulaC19H34N·C10H7O5S
Mr515.70
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)8.6720 (2), 17.1110 (3), 18.8201 (4)
α, β, γ (°)86.4785 (11), 83.9245 (12), 85.4033 (11)
V (Å3)2764.08 (10)
Z4
Radiation typeCu Kα
µ (mm−1)1.35
Crystal size (mm)0.38 × 0.33 × 0.15
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.650, 0.817
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections		22714, 9189, 6913
Rint0.038
(sin θ/λ)max (Å−1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.211, 1.12
No. of reflections9189
No. of parameters659
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.61, −0.47

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2006), SIR2004 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4O···O3i0.8201.8532.670 (3)174
O5—H5O···O8ii0.8201.8302.625 (3)163
O9—H9O···O20.8201.8492.650 (3)165
O10—H10O···O6iii0.8201.9272.705 (3)158
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, y+1, z; (iii) −x+2, −y+1, −z.
 

Acknowledgements

The authors express their sincere thanks to Mr O. Yamate at Orient Chemical Industries, Ltd for the sample preparation.

References

First citationBurla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.  CrossRef IUCr Journals Google Scholar
 First citationBurnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory. Tennessee, USA.  Google Scholar
 First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationMizuguchi, J., Sato, Y., Uta, K. & Sato, K. (2007). Acta Cryst. E63, o2509–o2510.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationNash, R. J., Grande, M. L. & Muller, R. N. (2001). Proceedings of the 7th International Conference on Advances in Non-Impact Printing Technology, pp. 358–364.  Google Scholar
 First citationRigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationRigaku/MSC (2006). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
 First citationSato, Y., Uta, K. & Mizuguchi, J. (2009). Acta Cryst. E65, o321.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationUta, K. & Mizuguchi, J. (2009a). Acta Cryst. E65, o320.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationUta, K. & Mizuguchi, J. (2009b). Acta Cryst. E65, o322.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationUta, K., Sato, Y. & Mizuguchi, J. (2009). Acta Cryst. E65, o319.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 2| February 2009| Page o323
doi:10.1107/S160053680900018X
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