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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o321.
Published online 2009 January 17. doi:  10.1107/S1600536809001056
PMCID: PMC2968364

Benzyl­tributyl­ammonium 7-hydroxy­naphthalene-1-sulfonate

Abstract

The title compound, C19H34N+·C10H7O4S, is a charge-control agent used for toners in electrophotography. The anions form one-dimensional chains by O—H(...)O hydrogen bonds in a zigzag fashion along the c axis between the OH group of one anion and the sulfonate O atom of a neighboring anion. One of the n-butyl chains of the cation is disordered over two sites in a 0.77:0.23 ratio.

Related literature

For the function of charge-control agents, see: Nash et al. (2001 [triangle]) and for the structure of benzyl­tributyl­ammonium 4-hydroxy­naphthalene-1-sulfonate, benzyl­tributyl­ammonium 6-hydroxy­naphthalene-2-sulfonate, and benzyl­tributyl­ammonium 4-hydroxy­naphthalene-2-sulfonate see: Mizuguchi et al. (2007 [triangle]), Uta et al. (2009 [triangle]), and Uta & Mizuguchi (2009 [triangle]), respectively.

An external file that holds a picture, illustration, etc.
Object name is e-65-0o321-scheme1.jpg

Experimental

Crystal data

  • C19H34N+·C10H7O4S
  • M r = 499.70
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o321-efi1.jpg
  • a = 19.8286 (6) Å
  • b = 8.8549 (2) Å
  • c = 16.7501 (4) Å
  • β = 104.7570 (13)°
  • V = 2843.98 (13) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 1.27 mm−1
  • T = 296.1 K
  • 0.39 × 0.36 × 0.04 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.650, T max = 0.951
  • 24641 measured reflections
  • 5082 independent reflections
  • 2591 reflections with F 2 > 2σ(F 2)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.080
  • wR(F 2) = 0.291
  • S = 1.02
  • 5082 reflections
  • 328 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.71 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 [triangle]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2006 [triangle]); program(s) used to solve structure: SIR2004 (Burla et al., 2003 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]); software used to prepare material for publication: CrystalStructure.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001056/bt2845sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001056/bt2845Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

The title compound 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 three isomers of compound (I) 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-4-sulfonate (Uta & Mizuguchi, 2009)]. The anions in the two former isomers are found to form chains of O—H···O intermolecular hydrogen bonds between the OH group of one anion and the sulfonate O atom of the neighboring one. The present hydrogen-bond network ensures a high thermal stability of these compounds as characterized by the melting points of 462 and 433K, respectively. On the other hand, the last isomer was characterized by a hydrogen-bonded dimer of the anions through O–H···O hydrogen bonding (melting point: 451 K). The present paper describes again one-dimensional chains of O—H···O intermoleclar hydrogen bonds.

Fig. 1 shows the ORTEPIII plot of the title compound. The ions have no crystallographically imposed symmetry. Fig. 2 shows a hydrogen-bonded chain along the c axis between the OH group of one anion and the sulfonic O atom of the neighboring one. The present linear chain is typically characterized by a zigzag form which is simlar to the one in benzyltributylammonium 4-hydroxynaphthalene-1-sulfonate (Mizuguchi et al., 2007) rather than the one in benzyltributylammonium 6-hydroxynaphthalene-2-sulfonate, Uta et al., 2009).

Experimental

The title compound was obtained from Orient Chemical Industries, Ltd, and was recrystallized from an acetone solution. After 48 h, a number of colorless crystals were obtained in the form of platelets. The title compound has a melting point of 439 K.

Refinement

C15 was found to be disordered over two sites. The site occupancies for C15A/C15B refined to 0.77 (1)/0.23 (1). 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 (aromatic), 0.96 (methyl), or 0.97Å (methylene), and O—H = 0.82Å, and with Uiso(H) = 1.2Ueq(parent atom).

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and only the major component of the disordered atoms.
Fig. 2.
View of the hydrogen-bonded (dashed lines) chain running along the c axis. Only anions are shown for clarity.

Crystal data

C19H34N+·C10H7O4SF(000) = 1080.00
Mr = 499.70Dx = 1.167 Mg m3
Monoclinic, P21/cMelting point: 439 K
Hall symbol: -P 2ybcCu Kα radiation, λ = 1.54187 Å
a = 19.8286 (6) ÅCell parameters from 15029 reflections
b = 8.8549 (2) Åθ = 3.1–68.1°
c = 16.7501 (4) ŵ = 1.26 mm1
β = 104.7570 (13)°T = 296 K
V = 2843.98 (13) Å3Platelet, colorless
Z = 40.39 × 0.36 × 0.04 mm

Data collection

Rigaku R-AXIS RAPID diffractometer2591 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.042
ω scansθmax = 68.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −23→23
Tmin = 0.650, Tmax = 0.951k = −10→10
24641 measured reflectionsl = −19→19
5082 independent reflections

Refinement

Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.080w = 1/[σ2(Fo2) + (0.1837P)2 + 0.0926P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.291(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.22 e Å3
5082 reflectionsΔρmin = −0.71 e Å3
328 parameters

Special details

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)

xyzUiso*/UeqOcc. (<1)
S10.24745 (5)0.42482 (10)0.48273 (6)0.0825 (3)
O10.26341 (15)0.4863 (3)0.40868 (16)0.0995 (8)
O20.20862 (14)0.5287 (2)0.51959 (17)0.1016 (8)
O30.21686 (15)0.2769 (2)0.46891 (16)0.0996 (8)
O40.23117 (15)0.1438 (3)0.75592 (16)0.1015 (8)
N10.19605 (14)0.5894 (2)0.83330 (18)0.0780 (8)
C10.0228 (2)0.5086 (5)0.7653 (3)0.1169 (14)
C2−0.0426 (2)0.5488 (7)0.7173 (5)0.143 (2)
C3−0.0533 (3)0.5852 (6)0.6376 (4)0.140 (2)
C40.0020 (3)0.5824 (6)0.6029 (4)0.148 (2)
C50.0682 (2)0.5447 (6)0.6497 (3)0.1181 (14)
C60.0800 (2)0.5085 (4)0.7324 (2)0.0913 (11)
C70.1511 (2)0.4632 (3)0.7827 (2)0.0884 (10)
C80.15890 (19)0.6643 (3)0.8909 (2)0.0859 (10)
C90.1472 (2)0.5662 (4)0.9600 (2)0.0980 (11)
C100.1022 (2)0.6408 (5)1.0078 (3)0.1144 (14)
C110.0887 (2)0.5487 (6)1.0747 (3)0.1406 (18)
C120.21187 (19)0.7113 (4)0.7765 (2)0.0874 (10)
C130.2501 (2)0.6592 (5)0.7148 (3)0.1122 (13)
C140.2834 (2)0.7853 (6)0.6794 (3)0.1304 (15)
C15A0.3514 (3)0.8302 (9)0.7319 (6)0.1440.77
C15B0.3524 (8)0.7787 (3)0.6626 (18)0.1320.23
C160.26209 (19)0.5147 (4)0.8810 (2)0.0901 (10)
C170.3155 (2)0.6162 (4)0.9349 (2)0.1037 (12)
C180.3768 (2)0.5210 (7)0.9851 (4)0.160 (2)
C190.4343 (3)0.6114 (8)1.0346 (5)0.201 (3)
C200.32863 (19)0.4039 (3)0.5553 (2)0.0806 (9)
C210.33489 (19)0.3335 (3)0.6343 (2)0.0819 (9)
C220.27822 (19)0.2672 (3)0.6588 (2)0.0805 (9)
C230.2876 (2)0.2048 (4)0.7355 (2)0.0850 (9)
C240.3539 (2)0.2060 (5)0.7924 (2)0.1034 (12)
C250.4082 (2)0.2663 (5)0.7697 (3)0.1114 (13)
C260.4020 (2)0.3316 (4)0.6916 (2)0.0989 (11)
C270.4596 (2)0.3959 (6)0.6690 (3)0.1288 (17)
C280.4519 (2)0.4577 (6)0.5935 (4)0.1329 (17)
C290.3867 (2)0.4611 (5)0.5372 (2)0.1058 (12)
H10.02830.48210.82030.139*
H2−0.07960.54920.74240.170*
H3−0.09730.61060.60670.167*
H4−0.00450.60680.54840.177*
H4O0.24340.11030.80320.121*
H50.10550.54220.62510.141*
H7A0.17650.42020.74590.105*
H7B0.14580.38360.82090.105*
H8A0.11430.70080.85850.101*
H8B0.18610.75190.91510.101*
H9A0.12500.47210.93690.117*
H9B0.19160.54110.99750.117*
H10A0.05770.66630.96910.136*
H10B0.12410.73581.02940.136*
H11A0.06870.45161.05480.207*
H11B0.05900.59811.10330.207*
H11C0.13330.52611.11590.207*
H12A0.23820.79010.81020.103*
H12B0.16740.75490.74630.103*
H13A0.28590.58720.74150.132*
H13B0.21830.60790.66970.132*
H14A0.28920.75450.62590.157*0.77
H14B0.25260.87210.67080.157*0.77
H14C0.25100.81170.62740.157*0.23
H14D0.28470.87100.71580.157*0.23
H15A0.38170.74390.74260.216*0.77
H15B0.34560.86960.78310.216*0.77
H15C0.37150.90650.70430.216*0.77
H15D0.38270.71630.70320.198*0.23
H15E0.37150.87870.66490.198*0.23
H15F0.34810.73680.60870.198*0.23
H16A0.28330.46470.84180.106*
H16B0.24950.43610.91520.106*
H17A0.29480.67150.97300.124*
H17B0.33250.68920.90150.124*
H18A0.36030.45281.02080.188*
H18B0.39480.45910.94650.188*
H19A0.45430.67240.99880.294*
H19B0.46970.54621.06660.294*
H19C0.41700.67621.07080.294*
H220.23400.26640.62140.095*
H240.35900.16490.84470.124*
H250.45180.26550.80780.134*
H270.50330.39570.70650.152*
H280.49060.49700.57860.157*
H290.38240.50400.48560.126*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.1011 (7)0.0675 (5)0.0765 (6)0.0067 (4)0.0179 (5)−0.0039 (4)
O10.135 (2)0.0933 (17)0.0707 (16)−0.0029 (15)0.0269 (14)0.0052 (13)
O20.1169 (19)0.0935 (16)0.0903 (18)0.0318 (15)0.0192 (15)−0.0127 (14)
O30.1196 (19)0.0722 (14)0.0969 (19)−0.0055 (13)0.0089 (15)−0.0042 (13)
O40.1150 (19)0.1011 (18)0.0881 (19)0.0086 (15)0.0251 (15)0.0080 (14)
N10.0851 (18)0.0645 (15)0.083 (2)−0.0028 (13)0.0197 (15)−0.0066 (13)
C10.099 (3)0.132 (3)0.122 (3)−0.014 (2)0.034 (2)−0.002 (3)
C20.093 (3)0.157 (4)0.174 (6)−0.011 (3)0.025 (3)−0.018 (4)
C30.108 (3)0.146 (4)0.141 (5)−0.017 (3)−0.015 (3)0.000 (4)
C40.129 (4)0.162 (5)0.135 (5)−0.025 (3)−0.002 (4)0.007 (3)
C50.115 (3)0.141 (3)0.097 (3)−0.021 (2)0.023 (2)−0.011 (3)
C60.099 (2)0.080 (2)0.094 (3)−0.0181 (19)0.023 (2)−0.017 (2)
C70.096 (2)0.0723 (19)0.095 (2)−0.0084 (18)0.022 (2)−0.0098 (19)
C80.102 (2)0.0730 (19)0.090 (2)−0.0015 (18)0.037 (2)−0.0101 (18)
C90.105 (2)0.098 (2)0.094 (3)−0.009 (2)0.032 (2)−0.008 (2)
C100.119 (3)0.120 (3)0.120 (3)−0.018 (2)0.060 (2)−0.011 (2)
C110.136 (3)0.171 (4)0.129 (4)−0.033 (3)0.059 (3)−0.001 (3)
C120.099 (2)0.0720 (19)0.092 (2)−0.0100 (18)0.025 (2)−0.0001 (18)
C130.128 (3)0.107 (2)0.114 (3)−0.013 (2)0.054 (2)0.000 (2)
C140.134 (3)0.119 (3)0.150 (4)−0.021 (2)0.057 (2)0.002 (2)
C15A0.128 (4)0.121 (4)0.180 (8)−0.012 (3)0.034 (4)−0.007 (5)
C15B0.144 (10)0.138 (13)0.132 (14)−0.039 (9)0.069 (10)−0.023 (12)
C160.087 (2)0.081 (2)0.099 (2)0.0024 (19)0.018 (2)−0.001 (2)
C170.095 (2)0.101 (2)0.104 (3)0.008 (2)0.005 (2)0.004 (2)
C180.115 (3)0.158 (4)0.178 (5)0.012 (3)−0.017 (3)−0.048 (4)
C190.130 (4)0.204 (6)0.228 (8)0.025 (4)−0.028 (4)−0.061 (6)
C200.089 (2)0.0734 (19)0.079 (2)0.0018 (16)0.0193 (18)−0.0023 (17)
C210.087 (2)0.0720 (19)0.085 (2)0.0074 (17)0.0179 (19)−0.0082 (17)
C220.091 (2)0.0735 (19)0.074 (2)0.0125 (17)0.0158 (18)0.0022 (17)
C230.097 (2)0.075 (2)0.081 (2)0.0097 (18)0.018 (2)−0.0014 (18)
C240.118 (3)0.101 (2)0.083 (2)0.014 (2)0.011 (2)0.003 (2)
C250.105 (3)0.120 (3)0.097 (3)0.006 (2)0.002 (2)0.007 (2)
C260.089 (2)0.105 (2)0.095 (2)0.008 (2)0.009 (2)0.005 (2)
C270.084 (2)0.175 (5)0.117 (4)−0.003 (2)0.006 (2)0.017 (3)
C280.106 (3)0.163 (4)0.130 (4)−0.019 (3)0.030 (3)0.009 (3)
C290.097 (2)0.115 (3)0.103 (3)−0.004 (2)0.020 (2)−0.002 (2)

Geometric parameters (Å, °)

S1—O11.461 (3)C5—H50.934
S1—O21.436 (3)C7—H7A0.968
S1—O31.438 (2)C7—H7B0.976
S1—C201.762 (3)C8—H8A0.968
O4—C231.362 (5)C8—H8B0.973
N1—C71.542 (4)C9—H9A0.974
N1—C81.508 (5)C9—H9B0.968
N1—C121.523 (4)C10—H10A0.980
N1—C161.503 (4)C10—H10B0.973
C1—C21.386 (7)C11—H11A0.970
C1—C61.383 (7)C11—H11B0.953
C2—C31.337 (11)C11—H11C0.993
C3—C41.366 (11)C12—H12A0.963
C4—C51.387 (7)C12—H12B0.978
C5—C61.383 (7)C13—H13A0.974
C6—C71.500 (5)C13—H13B0.966
C8—C91.513 (5)C14—H14A0.970
C9—C101.495 (6)C14—H14B0.970
C10—C111.466 (7)C14—H14C0.970
C12—C131.501 (6)C14—H14D0.970
C13—C141.496 (7)C15A—H15A0.960
C14—C15A1.465C15A—H15B0.960
C14—C15B1.465C15A—H15C0.960
C16—C171.502 (5)C15B—H15D0.960
C17—C181.542 (6)C15B—H15E0.960
C18—C191.465 (8)C15B—H15F0.960
C20—C211.440 (5)C16—H16A0.972
C20—C291.361 (6)C16—H16B0.973
C21—C221.418 (5)C17—H17A0.974
C21—C261.429 (5)C17—H17B0.969
C22—C231.367 (5)C18—H18A0.965
C23—C241.414 (5)C18—H18B0.981
C24—C251.341 (7)C19—H19A0.965
C25—C261.407 (6)C19—H19B0.960
C26—C271.412 (7)C19—H19C0.960
C27—C281.351 (8)C22—H220.938
C28—C291.393 (6)C24—H240.930
O4—H4O0.821C25—H250.934
C1—H10.930C27—H270.931
C2—H20.934C28—H280.931
C3—H30.922C29—H290.927
C4—H40.915
O1···O4i2.729 (3)O3···H9Bi2.920
O4···O1ii2.729 (3)O3···H16Bi2.254
S1···H3iii2.989O4···H7A2.665
O1···H4Oi1.912O4···H14Bv2.883
O1···H8Biv2.796O4···H14Dv2.789
O1···H12Aiv2.544C15A···H27vi2.861
O1···H24i2.751C15B···H19Civ2.275
O2···H3iii2.914C19···H15Evii2.778
O2···H8Biv2.576C19···H15Fvii2.712
O2···H10Biv2.706C23···H7A2.952
O2···H13B2.571C23···H14Dv2.973
O2···H14A2.876C23···H16A2.924
O3···H3iii2.586C24···H15Bv2.986
O3···H7Bi2.893C24···H16A2.913
O3···H9Ai2.822C29···H15F2.906
O1—S1—O2112.46 (16)C9—C10—H10B108.1
O1—S1—O3112.13 (16)C11—C10—H10A108.9
O1—S1—C20105.50 (18)C11—C10—H10B110.4
O2—S1—O3113.73 (18)H10A—C10—H10B106.8
O2—S1—C20105.46 (17)C10—C11—H11A111.7
O3—S1—C20106.79 (15)C10—C11—H11B112.6
C7—N1—C8111.2 (2)C10—C11—H11C109.8
C7—N1—C12110.7 (2)H11A—C11—H11B109.2
C7—N1—C16106.1 (2)H11A—C11—H11C106.0
C8—N1—C12107.4 (2)H11B—C11—H11C107.2
C8—N1—C16110.8 (2)N1—C12—H12A108.4
C12—N1—C16110.7 (2)N1—C12—H12B107.6
C2—C1—C6120.7 (5)C13—C12—H12A109.4
C1—C2—C3121.8 (6)C13—C12—H12B108.1
C2—C3—C4118.7 (5)H12A—C12—H12B107.4
C3—C4—C5120.7 (6)C12—C13—H13A108.8
C4—C5—C6121.1 (5)C12—C13—H13B109.8
C1—C6—C5116.9 (3)C14—C13—H13A109.1
C1—C6—C7121.7 (4)C14—C13—H13B107.9
C5—C6—C7121.3 (4)H13A—C13—H13B107.8
N1—C7—C6116.4 (2)C13—C14—H14A108.9
N1—C8—C9115.6 (2)C13—C14—H14B108.9
C8—C9—C10112.6 (3)C13—C14—H14C106.1
C9—C10—C11114.4 (4)C13—C14—H14D106.1
N1—C12—C13115.6 (3)C15A—C14—H14A108.9
C12—C13—C14113.3 (3)C15A—C14—H14B108.9
C13—C14—C15A113.3C15B—C14—H14C106.1
C13—C14—C15B125.1C15B—C14—H14D106.1
N1—C16—C17116.2 (2)H14A—C14—H14B107.7
C16—C17—C18109.7 (3)H14C—C14—H14D106.3
C17—C18—C19113.7 (5)C14—C15A—H15A109.5
S1—C20—C21122.0 (2)C14—C15A—H15B109.5
S1—C20—C29118.9 (3)C14—C15A—H15C109.5
C21—C20—C29119.1 (3)H15A—C15A—H15B109.5
C20—C21—C22123.8 (3)H15A—C15A—H15C109.5
C20—C21—C26118.0 (3)H15B—C15A—H15C109.5
C22—C21—C26118.2 (3)C14—C15B—H15D109.5
C21—C22—C23120.8 (3)C14—C15B—H15E109.5
O4—C23—C22118.2 (3)C14—C15B—H15F109.5
O4—C23—C24121.1 (3)H15D—C15B—H15E109.5
C22—C23—C24120.7 (4)H15D—C15B—H15F109.5
C23—C24—C25119.2 (4)H15E—C15B—H15F109.5
C24—C25—C26122.8 (3)N1—C16—H16A107.9
C21—C26—C25118.3 (4)N1—C16—H16B108.0
C21—C26—C27119.6 (4)C17—C16—H16A108.6
C25—C26—C27122.0 (3)C17—C16—H16B108.8
C26—C27—C28120.5 (4)H16A—C16—H16B107.0
C27—C28—C29120.5 (5)C16—C17—H17A110.1
C20—C29—C28122.2 (4)C16—C17—H17B110.4
C23—O4—H4O109.0C18—C17—H17A108.8
C2—C1—H1119.7C18—C17—H17B109.7
C6—C1—H1119.6H17A—C17—H17B108.0
C1—C2—H2117.8C17—C18—H18A109.5
C3—C2—H2120.3C17—C18—H18B108.4
C2—C3—H3120.5C19—C18—H18A109.3
C4—C3—H3120.8C19—C18—H18B108.5
C3—C4—H4119.7H18A—C18—H18B107.3
C5—C4—H4119.6C18—C19—H19A109.8
C4—C5—H5119.9C18—C19—H19B109.9
C6—C5—H5119.1C18—C19—H19C109.4
N1—C7—H7A108.2H19A—C19—H19B109.1
N1—C7—H7B107.9H19A—C19—H19C109.1
C6—C7—H7A108.3H19B—C19—H19C109.5
C6—C7—H7B108.6C21—C22—H22118.9
H7A—C7—H7B107.1C23—C22—H22120.3
N1—C8—H8A108.3C23—C24—H24119.4
N1—C8—H8B108.0C25—C24—H24121.4
C9—C8—H8A108.9C24—C25—H25118.2
C9—C8—H8B108.4C26—C25—H25119.0
H8A—C8—H8B107.4C26—C27—H27119.6
C8—C9—H9A109.2C28—C27—H27119.8
C8—C9—H9B109.7C27—C28—H28119.7
C10—C9—H9A108.7C29—C28—H28119.8
C10—C9—H9B108.8C20—C29—H29118.5
H9A—C9—H9B107.7C28—C29—H29119.3
C9—C10—H10A107.9C14—H14A—C15B80.7
O1—S1—C20—C21−174.5 (2)C8—C9—C10—C11179.1 (3)
O1—S1—C20—C298.0 (3)N1—C12—C13—C14−162.1 (3)
O2—S1—C20—C2166.3 (3)C12—C13—C14—C15A82.9
O2—S1—C20—C29−111.2 (3)C12—C13—C14—C15B140.1
O3—S1—C20—C21−55.1 (3)N1—C16—C17—C18175.1 (4)
O3—S1—C20—C29127.5 (3)C16—C17—C18—C19175.3 (5)
C7—N1—C8—C966.7 (3)S1—C20—C21—C224.1 (5)
C8—N1—C7—C656.5 (4)S1—C20—C21—C26−175.4 (2)
C7—N1—C12—C13−59.3 (3)S1—C20—C29—C28175.7 (4)
C12—N1—C7—C6−62.8 (4)C21—C20—C29—C28−1.8 (6)
C7—N1—C16—C17179.2 (3)C29—C20—C21—C22−178.5 (3)
C16—N1—C7—C6177.1 (3)C29—C20—C21—C262.1 (5)
C8—N1—C12—C13179.1 (2)C20—C21—C22—C23−178.7 (3)
C12—N1—C8—C9−172.1 (2)C20—C21—C26—C25178.5 (3)
C8—N1—C16—C17−60.0 (4)C20—C21—C26—C27−0.9 (6)
C16—N1—C8—C9−51.0 (3)C22—C21—C26—C25−1.0 (5)
C12—N1—C16—C1759.1 (4)C22—C21—C26—C27179.6 (4)
C16—N1—C12—C1358.0 (3)C26—C21—C22—C230.7 (5)
C2—C1—C6—C5−2.3 (6)C21—C22—C23—O4179.5 (3)
C2—C1—C6—C7−179.1 (4)C21—C22—C23—C240.5 (5)
C6—C1—C2—C31.7 (8)O4—C23—C24—C25179.6 (4)
C1—C2—C3—C40.0 (8)C22—C23—C24—C25−1.5 (6)
C2—C3—C4—C5−1.0 (9)C23—C24—C25—C261.2 (7)
C3—C4—C5—C60.2 (6)C24—C25—C26—C210.0 (5)
C4—C5—C6—C11.4 (7)C24—C25—C26—C27179.4 (4)
C4—C5—C6—C7178.2 (4)C21—C26—C27—C28−0.6 (7)
C1—C6—C7—N1−87.5 (4)C25—C26—C27—C28−180.0 (4)
C5—C6—C7—N195.9 (4)C26—C27—C28—C291.0 (9)
N1—C8—C9—C10−172.6 (2)C27—C28—C29—C200.2 (7)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) −x, −y+1, −z+1; (iv) x, −y+3/2, z−1/2; (v) x, y−1, z; (vi) −x+1, y+1/2, −z+3/2; (vii) x, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4—H4O···O1ii0.821.912.729 (3)173

Symmetry codes: (ii) x, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2845).

References

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