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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 64| Part 7| July 2008| Pages o1238-o1239
doi:10.1107/S1600536808016528

A low-temperature phase of the 1:1 complex of 2-(6-di­ethylamino-3-di­ethyl­iminio-3H-xanthen-9-yl)benzoate with ethyl gallate at 93 K

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 8 May 2008; accepted 30 May 2008; online 7 June 2008)

The title compound, C28H30N2O3·C9H10O5, is a well known red leuco complex of 2-(6-diethylamino-3-diethyl­iminio-3H-xanthen-9-yl)benzoate (rhodamine B base abbreviated to RBB, a leuco dye) with ethyl gallate (EG, developer). The structure of the complex at room temperature has recently been reported by Sekiguchi, Takayama, Gotanda & Sano [Chem. Lett. (2007[Sekiguchi, Y., Takayama, S., Gotanda, T. & Sano, K. (2007). Chem. Lett. 36, 1010-1011.]), 36, 1010–1011]. We have found a new phase of the material with two discrete base/developer complexes (RBB-A/EG-A and RBB-B/EG-B) in the asymmetric unit at 93 K. There are no significant differences between the two developer mol­ecules EG-A and EG-B. The lactone ring of RBB is opened in each mol­ecule to form a zwitterionic structure. However, the xanthene system is almost flat in RBB-A (r.m.s. deviation 0.0234 Å) but is less so in RBB-B (r.m.s. deviation 0.1095 Å). Furthermore, the ethyl groups of the xanthene diethyl­amino substituents lie on the same side of the xanthene plane in RBB-A but on opposite sides in RBB-B. Dimeric dye/developer complexes are formed through inter- and intra­molecular O—H⋯O hydrogen bonds and are linked further into dimers by additional O—H⋯O hydrogen bonds involving either EG-A or EG-B developer mol­ecules.

Related literature

For general background literature on leuco dyes, see: Muthyala (1997[Muthyala, R. (1997). Chemistry and Applications of Leuco Dyes. New York, London: Plenum Press.]). For the structure of the 1:1 RBB/EG complex at room temperature, see: Sekiguchi et al. (2007[Sekiguchi, Y., Takayama, S., Gotanda, T. & Sano, K. (2007). Chem. Lett. 36, 1010-1011.]). For the related structure of n-propyl gallate, see: Iwata et al. (2005[Iwata, S., Hitachi, A., Makino, T. & Mizuguchi, J. (2005). Acta Cryst. E61, o2587-o2589.]); Hitachi et al. (2005[Hitachi, A., Makino, T., Iwata, S. & Mizuguchi, J. (2005). Acta Cryst. E61, o2590-o2592.]); Mizuguchi et al. (2005[Mizuguchi, J., Hitachi, A., Iwata, S. & Makino, T. (2005). Acta Cryst. E61, o2593-o2595.]).

[Scheme 1]

Experimental

Crystal data

  • C28H30N2O3·C9H10O5

  • Mr = 640.71

  • Triclinic, [P \overline 1]

  • a = 11.3689 (2) Å

  • b = 16.3654 (3) Å

  • c = 17.6518 (3) Å

  • α = 94.1760 (7)°

  • β = 96.1440 (7)°

  • γ = 93.7790 (7)°

  • V = 3247.69 (10) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.76 mm−1

  • T = 93 K

  • 0.20 × 0.20 × 0.20 mm
Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.810, Tmax = 0.860

  • 29633 measured reflections

  • 11011 independent reflections

  • 7318 reflections with F2 > 2σ(F2)

  • Rint = 0.039
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.115

  • S = 0.94

  • 11011 reflections

  • 881 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O6A—H6AO⋯O2A 0.94 (2) 2.72 (2) 3.4413 (18) 133.8 (18)
O6A—H6AO⋯O3A 0.94 (2) 1.72 (2) 2.6303 (17) 162 (2)
O6A—H6AO⋯O5A 0.94 (2) 2.53 (2) 2.8733 (19) 102.2 (17)
O5A—H5AO⋯O2A 0.92 (2) 1.66 (2) 2.5690 (19) 167 (2)
O5A—H5AO⋯O3A 0.92 (2) 2.62 (2) 3.1884 (18) 120.4 (18)
O4A—H4AO⋯O7Ai 0.92 (2) 1.86 (2) 2.779 (2) 178.8 (10)
O6B—H6BO⋯O2B 0.94 (2) 2.72 (2) 3.4156 (18) 131.4 (16)
O6B—H6BO⋯O3B 0.94 (2) 1.68 (2) 2.5811 (17) 159 (2)
O6B—H6BO⋯O5B 0.94 (2) 2.55 (2) 2.8799 (19) 101.0 (15)
O5B—H5BO⋯O2B 0.94 (2) 1.64 (2) 2.5636 (18) 166 (2)
O5B—H5BO⋯O3B 0.94 (2) 2.66 (2) 3.2473 (18) 121.5 (19)
O4B—H4BO⋯O7Bii 0.97 (2) 1.83 (2) 2.7957 (19) 175 (2)
Symmetry codes: (i) -x+3, -y+1, -z+1; (ii) -x+3, -y+2, -z+2.

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., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); 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/S1600536808016528/sj2498sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808016528/sj2498Isup2.hkl

checkCIF report


Comment top

The coloration of colorless leuco dyes by reaction with acidic developers is well known (Muthyala, 1997) and is used in practice in thermal or rewritable papers. The coloration is usually interpreted as arising from the opening of the lactone ring due to proton transfer from the developer, acting as a proton donor, to the leuco dye, a proton acceptor. The title compound [C28H30N2O3, C9H10N2O5] is a typical example of a leuco coloration system composed of 2-(6-diethylamino-3-diethyliminio-3H-xanthen-9-yl)benzoate [rhodamine B base (RBB): a leuco dye] with ethyl gallate (EG: a developer). The structure of the 1:1 dye:developer complex at room temperature has recently been reported by Sekiguchi et al. (2007). They found a dimer structure, in which two RBBs are connected by a sub dimer of EG through OH···O intermolecular hydrogen bonds. We have found a new phase of the material at 93 K with two discrete base/developer complexes RBB-A/EG-A and RBB-B/EG-B in the asymmetric unit, Fig. 1.

The lactone rings of each RBB are opened to form zwitterionic structures and the benzene rings with the anionic carboxylate substituents are twisted to be nearly perpendicular to the xanthene planes with dihedral angles: 84.68 (7)°) between the O1A/C4A/C5A/C7A/C12A/C13A and C14A-C19A planes of RBB-A and 73.09 (7)° between the O1B/C4B/C5B/C7B/C12B/C13B and C14B-C19B planes of RBB-B. There are no significant differences between the two developer molecules EG-A and EG-B. The xanthene moiety is nearly flat in RBB-A (deviation from the least-squares plane, 0.0234Å) and the ethyl groups of the diethylamino substituents at each extremity of the xanthene lie on the same side of the xanthene plane. On the other hand, in RBB-B, the xanthene moiety deviates slightly from planarity by 0.1095Å and the ethyl groups of the diethylamino substituents lie on opposite sides of the xanthene plane. By comparison, the room temperature phase (Sekiguchi et al., 2007) crystallises with only one type of the molecule (eqivalent to RBB-A) in the asymmetric unit and with the ethyl groups of the diethylamino substituents all on the same side of the xanthene plane.

The dye/developer complexes are formed through intermolecular O5—H5O···O2, O6—H6O···O2, O5—H5O···O3 and O6—H6O···O3 hydrogen bonds with the planar configuration of this section of the molecule supported by intramolecular O6—H6O···O5 interactions, Figs. 2 & 3. In addition, O4—H4···O7 hydrogen-bonds form centrosymmetric RBB-A···EG-A···EG-A···RBB-A (Fig. 4), and RBB-B···EG-B···EG-B···RBB-B dimers. These are similar to those found in n-propyl gallate (Iwata et al., 2005; Hitachi et al., 2005; Mizuguchi et al., 2005).

Related literature top

For general background literature on leuco dyes, see: Muthyala (1997). For the structure of the 1:1 RBB/EG complex at room temperature, see: Sekiguchi et al. (2007). For the related structure of n-propyl gallate, see: Iwata et al. (2005); Hitachi et al. (2005); Mizuguchi et al. (2005).

Experimental top

Rhodamine B base and 4-hydroxybenzophenone were purchased from Sigma-Aldrich Corp. and and Wako Pure Chemical Industries, Ltd., respectively. Single crystals of (I) were grown by recrystallization from a toluene solution which included an equimolar quantity of both chemicals. After 24 h, a number of red crystals were obtained in the form of blocks.

Refinement top

H4AO, H4BO, H5AO, H5BO, H6AO, and H6BO were located in electron density maps and were refined with isotropic displacement parameters. All the rest of the H atoms were placed in geometrically idealized position and constrained to ride on their parent atoms, with C—H = 0.93, 0.96, and 0.97 Å, and Uiso(H) = 1.2 and 1.5 Ueq(C), respectively.

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., 2005); 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 structure of (I), showing 50% displacement ellipsoids and the atom numbering scheme.
[Figure 2] Fig. 2. O—H···O intra- and intermolecular hydrogen bonds leading to the formation of the RBB-A/EG-A complex. For clarity only the C29A···C34A benzene ring and its substituents are shown for the RBB-A unit.
[Figure 3] Fig. 3. O—H···O intra- and intermolecular hydrogen bonds leading to the formation of the RBB-B/EG-B complex. For clarity only the C29B···C34B benzene ring and its substituents are shown for the RBB-B unit.
[Figure 4] Fig. 4. Hydrogen-bonded RBB-A···EG-A···EG-A···RBB-A dimers formed by linking two RBB/EG complexes.
2-(6-diethylamino-3-diethyliminio-3H-xanthen-9-yl)benzoate–ethyl 3,4,5-trihydroxybenzoate (1/1) top
Crystal data top
C28H30N2O3·C9H10O5Z = 4
Mr = 640.71F(000) = 1360.00
Triclinic, P1Dx = 1.310 Mg m−3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54187 Å
a = 11.3689 (2) ÅCell parameters from 23114 reflections
b = 16.3654 (3) Åθ = 3.0–68.5°
c = 17.6518 (3) ŵ = 0.76 mm−1
α = 94.1760 (7)°T = 93 K
β = 96.1440 (7)°Block, red
γ = 93.7790 (7)°0.20 × 0.20 × 0.20 mm
V = 3247.69 (10) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer		7318 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.039
ω scansθmax = 68.3°
Absorption correction: multi-scan
(Higashi, 1995)		h = −13→13
Tmin = 0.810, Tmax = 0.860k = −19→19
29633 measured reflectionsl = −19→19
11011 independent reflections
Refinement top
Refinement on F20 restraints
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0668P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max = 0.001
11011 reflectionsΔρmax = 0.23 e Å−3
881 parametersΔρmin = −0.25 e Å−3
Crystal data top
C28H30N2O3·C9H10O5γ = 93.7790 (7)°
Mr = 640.71V = 3247.69 (10) Å3
Triclinic, P1Z = 4
a = 11.3689 (2) ÅCu Kα radiation
b = 16.3654 (3) ŵ = 0.76 mm−1
c = 17.6518 (3) ÅT = 93 K
α = 94.1760 (7)°0.20 × 0.20 × 0.20 mm
β = 96.1440 (7)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		11011 independent reflections
Absorption correction: multi-scan
(Higashi, 1995)		7318 reflections with F2 > 2σ(F2)
Tmin = 0.810, Tmax = 0.860Rint = 0.039
29633 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 0.94Δρmax = 0.23 e Å−3
11011 reflectionsΔρmin = −0.25 e Å−3
881 parameters
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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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*/Ueq
O1B0.87836 (10)0.98739 (7)0.42995 (7)0.0229 (3)
O2B0.90792 (11)0.95942 (8)0.79262 (7)0.0281 (3)
O3B0.93454 (11)1.01742 (8)0.68439 (7)0.0267 (3)
O1A0.88374 (11)0.47147 (7)−0.06554 (7)0.0240 (3)
O2A0.89121 (11)0.48936 (8)0.30288 (7)0.0297 (3)
O3A0.92734 (11)0.51496 (8)0.18428 (7)0.0293 (3)
O6A1.13694 (12)0.58483 (8)0.23956 (8)0.0291 (3)
O5A1.09716 (13)0.43281 (8)0.30792 (8)0.0338 (3)
O4A1.25444 (12)0.39351 (8)0.42047 (8)0.0324 (3)
O7A1.57886 (13)0.62783 (9)0.45684 (9)0.0469 (4)
O8A1.50522 (11)0.71810 (8)0.37821 (8)0.0317 (3)
O6B1.13331 (12)1.08929 (8)0.74789 (8)0.0288 (3)
O5B1.12346 (12)0.92278 (8)0.79090 (8)0.0290 (3)
O4B1.29851 (12)0.87659 (8)0.88819 (8)0.0302 (3)
O7B1.56742 (12)1.13800 (8)0.97180 (8)0.0333 (3)
O8B1.48988 (11)1.22678 (8)0.89288 (8)0.0322 (3)
N2B0.71903 (14)1.23884 (9)0.37466 (9)0.0277 (4)
N1B0.97157 (14)0.71094 (9)0.43325 (9)0.0274 (4)
N2A0.81195 (14)0.74802 (9)−0.10608 (9)0.0268 (3)
N1A0.95787 (14)0.19150 (9)−0.04933 (9)0.0288 (4)
C9B0.74323 (16)1.18196 (11)0.42495 (11)0.0256 (4)
C8B0.80925 (16)1.11476 (11)0.40636 (11)0.0240 (4)
C7B0.81752 (16)1.05203 (11)0.45422 (11)0.0219 (4)
C12B0.76375 (16)1.05087 (11)0.52263 (11)0.0219 (4)
C11B0.70771 (16)1.12247 (11)0.54336 (11)0.0257 (4)
C10B0.69800 (17)1.18574 (12)0.49776 (11)0.0280 (4)
C13B0.76693 (16)0.98015 (11)0.56424 (11)0.0220 (4)
C4B0.82581 (15)0.91354 (11)0.53678 (11)0.0214 (4)
C5B0.88086 (16)0.91770 (11)0.46921 (11)0.0215 (4)
C6B0.93269 (16)0.85388 (11)0.43505 (11)0.0237 (4)
C1B0.93259 (16)0.77761 (11)0.46880 (11)0.0247 (4)
C2B0.88574 (16)0.77399 (11)0.54089 (11)0.0252 (4)
C3B0.83370 (16)0.83817 (11)0.57228 (11)0.0242 (4)
C14B0.69254 (16)0.97331 (10)0.62840 (11)0.0222 (4)
C15B0.56987 (16)0.96165 (11)0.60911 (11)0.0268 (4)
C16B0.49399 (17)0.95451 (11)0.66448 (12)0.0298 (5)
C17B0.53913 (17)0.95787 (11)0.74086 (12)0.0282 (4)
C18B0.66080 (16)0.96716 (11)0.76036 (12)0.0270 (4)
C19B0.73859 (16)0.97497 (11)0.70563 (11)0.0221 (4)
C20B0.87033 (16)0.98517 (11)0.72922 (11)0.0213 (4)
C27B0.64851 (18)1.30864 (12)0.39121 (12)0.0353 (5)
C28B0.51632 (19)1.28710 (14)0.36980 (13)0.0500 (6)
C25B0.74973 (17)1.22856 (12)0.29529 (11)0.0308 (5)
C26B0.87317 (18)1.26447 (12)0.28673 (12)0.0359 (5)
C23B0.96527 (18)0.62858 (11)0.46230 (12)0.0311 (5)
C24B1.08162 (19)0.61184 (12)0.50674 (12)0.0419 (5)
C21B1.01170 (19)0.71283 (12)0.35719 (11)0.0334 (5)
C22B0.90840 (19)0.70483 (12)0.29420 (12)0.0391 (5)
C9A0.80213 (16)0.68192 (11)−0.06451 (11)0.0249 (4)
C8A0.84590 (16)0.60628 (11)−0.08668 (11)0.0239 (4)
C7A0.83537 (16)0.54155 (11)−0.04116 (11)0.0230 (4)
C12A0.77610 (16)0.54502 (11)0.02534 (11)0.0222 (4)
C11A0.73357 (16)0.62160 (11)0.04646 (11)0.0269 (4)
C10A0.74587 (16)0.68720 (11)0.00457 (11)0.0264 (4)
C13A0.76571 (16)0.47473 (11)0.06661 (11)0.0232 (4)
C4A0.81712 (16)0.40392 (11)0.04120 (11)0.0230 (4)
C5A0.87533 (16)0.40257 (11)−0.02569 (11)0.0224 (4)
C6A0.92214 (16)0.33482 (11)−0.05662 (11)0.0241 (4)
C1A0.91606 (16)0.26098 (11)−0.01902 (11)0.0256 (4)
C2A0.86306 (16)0.26195 (11)0.05052 (11)0.0262 (4)
C3A0.81486 (16)0.32957 (11)0.07845 (11)0.0247 (4)
C14A0.68673 (16)0.47247 (11)0.12900 (11)0.0233 (4)
C15A0.56556 (17)0.45371 (11)0.10668 (12)0.0292 (4)
C16A0.48590 (17)0.44929 (12)0.16068 (12)0.0319 (5)
C17A0.52564 (17)0.46464 (11)0.23766 (12)0.0300 (4)
C18A0.64616 (17)0.48172 (11)0.26028 (12)0.0277 (4)
C19A0.72793 (16)0.48491 (11)0.20708 (11)0.0230 (4)
C20A0.85903 (16)0.49799 (11)0.23319 (12)0.0235 (4)
C27A0.75459 (17)0.82365 (11)−0.08670 (12)0.0330 (5)
C28A0.62064 (18)0.81610 (13)−0.10645 (13)0.0409 (5)
C25A0.86617 (17)0.74497 (12)−0.17806 (11)0.0298 (4)
C26A0.77640 (19)0.72455 (13)−0.24777 (11)0.0387 (5)
C23A0.95564 (18)0.11495 (12)−0.01047 (12)0.0344 (5)
C24A0.84570 (18)0.05831 (12)−0.03624 (12)0.0368 (5)
C21A0.98746 (18)0.18428 (12)−0.12816 (12)0.0348 (5)
C22A0.88023 (19)0.18476 (12)−0.18812 (12)0.0386 (5)
C29A1.39147 (17)0.59375 (11)0.38322 (11)0.0246 (4)
C34A1.30914 (16)0.61475 (11)0.32518 (11)0.0250 (4)
C33A1.21080 (16)0.56133 (11)0.29828 (11)0.0252 (4)
C32A1.19155 (17)0.48701 (11)0.33185 (11)0.0257 (4)
C31A1.27562 (17)0.46701 (11)0.39004 (11)0.0258 (4)
C30A1.37478 (17)0.51900 (11)0.41521 (11)0.0275 (4)
C35A1.50052 (18)0.64666 (12)0.41029 (12)0.0306 (5)
C36A1.61415 (18)0.77074 (13)0.39752 (13)0.0410 (5)
C37A1.60159 (19)0.84407 (13)0.35256 (13)0.0471 (6)
C29B1.39195 (16)1.09548 (11)0.88757 (11)0.0230 (4)
C34B1.30324 (16)1.11904 (11)0.83478 (11)0.0247 (4)
C33B1.21358 (16)1.06213 (11)0.80066 (11)0.0235 (4)
C32B1.20951 (16)0.98077 (11)0.82163 (11)0.0224 (4)
C31B1.30135 (17)0.95803 (11)0.87335 (11)0.0238 (4)
C30B1.39119 (16)1.01438 (11)0.90654 (11)0.0252 (4)
C35B1.49108 (17)1.15383 (11)0.92221 (11)0.0262 (4)
C36B1.58894 (19)1.28594 (12)0.91921 (13)0.0406 (5)
C37B1.5856 (2)1.35179 (14)0.86645 (14)0.0554 (7)
H6BO1.0703 (19)1.0521 (13)0.7266 (12)0.052 (7)*
H5BO1.049 (2)0.9436 (15)0.7960 (14)0.089 (9)*
H5AO1.029 (2)0.4605 (14)0.3091 (13)0.078 (9)*
H6AO1.067 (2)0.5509 (14)0.2251 (13)0.076 (8)*
H4BO1.348 (2)0.8715 (14)0.9351 (14)0.081 (9)*
H4AO1.3091 (19)0.3857 (13)0.4612 (12)0.057 (7)*
H8B0.84691.11280.36210.029*
H11B0.67631.12650.58990.031*
H10B0.66151.23210.51410.034*
H6B0.96760.86030.39030.028*
H2B0.89130.72650.56660.030*
H3B0.80210.83310.61830.029*
H15B0.53890.95870.55800.032*
H16B0.41250.94740.65060.036*
H17B0.48830.95390.77860.034*
H18B0.69100.96820.81150.032*
H27A0.67371.35420.36300.042*
H27B0.66301.32620.44530.042*
H28A0.50171.26890.31650.075*
H28B0.47371.33480.37980.075*
H28C0.49011.24410.39960.075*
H25A0.69271.25480.26210.037*
H25B0.74361.17050.27870.037*
H26A0.87991.32200.30290.054*
H26B0.88761.25710.23420.054*
H26C0.93041.23710.31770.054*
H23A0.94630.58730.41970.037*
H23B0.90230.62460.49520.037*
H24A1.14340.61350.47370.063*
H24B1.07430.55850.52590.063*
H24C1.10080.65290.54870.063*
H21A1.06230.66820.34920.040*
H21B1.05840.76410.35440.040*
H22A0.85320.66040.30290.059*
H22B0.93740.69400.24560.059*
H22C0.86930.75510.29430.059*
H8A0.88160.6000−0.13160.029*
H11A0.69590.62720.09060.032*
H10A0.71730.73670.02090.032*
H6A0.95750.3369−0.10160.029*
H2A0.86160.21510.07730.031*
H3A0.77920.32750.12330.030*
H15A0.53820.44410.05500.035*
H16A0.40570.43600.14520.038*
H17A0.47210.46350.27390.036*
H18A0.67270.49120.31210.033*
H27C0.78800.8677−0.11360.040*
H27D0.77280.8388−0.03230.040*
H28D0.60170.8054−0.16070.061*
H28E0.58870.8664−0.09000.061*
H28F0.58690.7717−0.08110.061*
H25C0.92410.7040−0.17670.036*
H25D0.90780.7978−0.18250.036*
H26D0.73050.6745−0.24190.058*
H26E0.81710.7179−0.29250.058*
H26F0.72470.7684−0.25310.058*
H23C0.95970.12850.04420.041*
H23D1.02520.0863−0.02020.041*
H24D0.77660.0889−0.03520.055*
H24E0.84100.0151−0.00250.055*
H24F0.84980.0350−0.08730.055*
H21C1.02560.1336−0.13660.042*
H21D1.04400.2294−0.13490.042*
H22D0.81880.1456−0.17730.058*
H22E0.90310.1704−0.23790.058*
H22F0.85130.2386−0.18690.058*
H34A1.31990.66480.30420.030*
H30A1.43040.50420.45340.033*
H36A1.68190.74180.38440.049*
H36B1.62540.78730.45180.049*
H37A1.58470.82650.29920.071*
H37B1.67410.87860.36080.071*
H37C1.53790.87430.36880.071*
H34B1.30401.17330.82220.030*
H30B1.45080.99830.94140.030*
H36C1.66311.25990.91910.049*
H36D1.58221.30830.97080.049*
H37D1.59431.32910.81580.083*
H37E1.64911.39290.88300.083*
H37F1.51111.37620.86620.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1B0.0235 (7)0.0198 (6)0.0263 (8)0.0035 (5)0.0056 (5)0.0030 (5)
O2B0.0230 (7)0.0336 (8)0.0277 (8)0.0003 (6)0.0005 (6)0.0079 (6)
O3B0.0199 (7)0.0332 (7)0.0264 (8)−0.0033 (6)0.0022 (6)0.0035 (6)
O1A0.0270 (7)0.0206 (6)0.0251 (8)0.0004 (5)0.0055 (6)0.0029 (5)
O2A0.0295 (7)0.0341 (8)0.0250 (8)0.0019 (6)−0.0011 (6)0.0053 (6)
O3A0.0216 (7)0.0382 (8)0.0271 (8)−0.0027 (6)0.0015 (6)0.0020 (6)
O6A0.0264 (7)0.0280 (7)0.0312 (9)0.0000 (6)−0.0048 (6)0.0043 (6)
O5A0.0246 (8)0.0245 (7)0.0494 (10)−0.0009 (6)−0.0070 (7)0.0012 (6)
O4A0.0312 (8)0.0278 (7)0.0373 (9)−0.0014 (6)−0.0038 (7)0.0106 (6)
O7A0.0369 (9)0.0469 (9)0.0520 (10)−0.0111 (7)−0.0197 (8)0.0210 (8)
O8A0.0266 (7)0.0290 (7)0.0375 (9)−0.0048 (6)−0.0042 (6)0.0065 (6)
O6B0.0253 (7)0.0249 (7)0.0335 (9)−0.0012 (6)−0.0085 (6)0.0051 (6)
O5B0.0230 (7)0.0248 (7)0.0372 (9)−0.0003 (6)−0.0022 (6)−0.0005 (6)
O4B0.0327 (8)0.0239 (7)0.0327 (9)−0.0003 (6)−0.0039 (6)0.0076 (6)
O7B0.0295 (8)0.0345 (8)0.0337 (9)−0.0001 (6)−0.0082 (6)0.0070 (6)
O8B0.0296 (7)0.0244 (7)0.0387 (9)−0.0072 (6)−0.0108 (6)0.0057 (6)
N2B0.0309 (9)0.0271 (9)0.0268 (10)0.0075 (7)0.0060 (7)0.0045 (7)
N1B0.0361 (9)0.0227 (8)0.0257 (10)0.0074 (7)0.0095 (7)0.0044 (7)
N2A0.0303 (9)0.0240 (8)0.0275 (10)0.0031 (7)0.0068 (7)0.0063 (7)
N1A0.0339 (9)0.0242 (9)0.0284 (10)0.0057 (7)0.0029 (8)0.0019 (7)
C9B0.0229 (10)0.0238 (10)0.0300 (13)0.0001 (8)0.0018 (8)0.0042 (8)
C8B0.0235 (10)0.0239 (10)0.0247 (12)−0.0007 (8)0.0039 (8)0.0024 (8)
C7B0.0186 (9)0.0185 (9)0.0274 (12)−0.0001 (7)0.0004 (8)−0.0013 (8)
C12B0.0202 (10)0.0234 (10)0.0211 (11)−0.0010 (8)0.0010 (8)0.0002 (8)
C11B0.0248 (10)0.0278 (10)0.0247 (12)0.0013 (8)0.0051 (8)0.0005 (8)
C10B0.0299 (11)0.0241 (10)0.0313 (13)0.0050 (8)0.0071 (9)0.0025 (9)
C13B0.0178 (9)0.0241 (10)0.0222 (11)−0.0034 (8)−0.0036 (8)0.0015 (8)
C4B0.0186 (9)0.0210 (9)0.0237 (12)−0.0019 (8)0.0009 (8)0.0011 (8)
C5B0.0208 (10)0.0207 (9)0.0222 (12)−0.0009 (7)−0.0020 (8)0.0052 (8)
C6B0.0235 (10)0.0249 (10)0.0235 (12)0.0015 (8)0.0047 (8)0.0044 (8)
C1B0.0219 (10)0.0236 (10)0.0281 (12)0.0024 (8)−0.0011 (8)0.0028 (8)
C2B0.0262 (10)0.0232 (10)0.0264 (12)−0.0002 (8)0.0027 (9)0.0053 (8)
C3B0.0259 (10)0.0237 (10)0.0227 (12)−0.0002 (8)0.0022 (8)0.0029 (8)
C14B0.0222 (10)0.0169 (9)0.0277 (12)−0.0001 (7)0.0030 (8)0.0033 (8)
C15B0.0240 (10)0.0305 (11)0.0251 (12)−0.0014 (8)−0.0009 (8)0.0052 (9)
C16B0.0205 (10)0.0313 (11)0.0374 (14)−0.0017 (8)0.0023 (9)0.0065 (9)
C17B0.0243 (10)0.0328 (11)0.0291 (13)0.0017 (9)0.0096 (9)0.0046 (9)
C18B0.0260 (11)0.0278 (10)0.0268 (12)−0.0010 (8)0.0019 (9)0.0043 (9)
C19B0.0203 (10)0.0181 (9)0.0274 (12)−0.0012 (7)0.0011 (8)0.0033 (8)
C20B0.0195 (10)0.0211 (9)0.0222 (12)0.0009 (8)0.0004 (8)−0.0015 (8)
C27B0.0443 (13)0.0273 (11)0.0377 (14)0.0122 (10)0.0101 (10)0.0081 (9)
C28B0.0410 (14)0.0589 (16)0.0525 (17)0.0226 (12)0.0041 (12)0.0061 (13)
C25B0.0330 (12)0.0292 (11)0.0316 (13)0.0077 (9)0.0045 (9)0.0056 (9)
C26B0.0402 (13)0.0307 (11)0.0380 (14)0.0004 (10)0.0082 (10)0.0064 (10)
C23B0.0391 (12)0.0211 (10)0.0335 (13)0.0048 (9)0.0054 (10)0.0011 (9)
C24B0.0508 (14)0.0310 (12)0.0430 (15)0.0057 (11)−0.0029 (11)0.0056 (10)
C21B0.0445 (13)0.0272 (11)0.0319 (13)0.0107 (9)0.0130 (10)0.0042 (9)
C22B0.0576 (15)0.0273 (11)0.0326 (14)0.0036 (10)0.0062 (11)0.0006 (9)
C9A0.0190 (10)0.0260 (10)0.0285 (12)−0.0020 (8)−0.0010 (8)0.0038 (8)
C8A0.0232 (10)0.0266 (10)0.0209 (11)−0.0032 (8)0.0023 (8)0.0007 (8)
C7A0.0198 (10)0.0214 (10)0.0266 (12)0.0001 (8)0.0001 (8)−0.0009 (8)
C12A0.0202 (10)0.0259 (10)0.0196 (11)−0.0024 (8)−0.0003 (8)0.0020 (8)
C11A0.0248 (10)0.0292 (11)0.0270 (12)0.0013 (8)0.0061 (8)0.0011 (9)
C10A0.0283 (11)0.0234 (10)0.0279 (12)0.0032 (8)0.0049 (9)0.0015 (8)
C13A0.0195 (9)0.0259 (10)0.0220 (12)−0.0039 (8)−0.0036 (8)0.0012 (8)
C4A0.0194 (10)0.0233 (10)0.0247 (12)−0.0027 (8)−0.0020 (8)0.0028 (8)
C5A0.0203 (10)0.0227 (10)0.0234 (12)−0.0016 (8)−0.0015 (8)0.0041 (8)
C6A0.0238 (10)0.0259 (10)0.0218 (12)−0.0000 (8)0.0005 (8)0.0011 (8)
C1A0.0224 (10)0.0243 (10)0.0288 (12)0.0010 (8)−0.0025 (8)0.0022 (8)
C2A0.0265 (10)0.0240 (10)0.0272 (12)−0.0015 (8)−0.0013 (9)0.0058 (8)
C3A0.0254 (10)0.0267 (10)0.0211 (12)−0.0013 (8)0.0004 (8)0.0023 (8)
C14A0.0211 (10)0.0220 (10)0.0271 (12)0.0004 (8)0.0023 (8)0.0050 (8)
C15A0.0274 (11)0.0330 (11)0.0260 (12)−0.0026 (9)−0.0013 (9)0.0050 (9)
C16A0.0201 (10)0.0348 (12)0.0408 (14)−0.0012 (9)0.0022 (9)0.0071 (10)
C17A0.0271 (11)0.0331 (11)0.0315 (13)0.0019 (9)0.0092 (9)0.0066 (9)
C18A0.0323 (11)0.0254 (10)0.0258 (12)0.0029 (9)0.0040 (9)0.0036 (8)
C19A0.0262 (10)0.0191 (9)0.0234 (12)0.0012 (8)0.0004 (8)0.0027 (8)
C20A0.0229 (10)0.0196 (10)0.0272 (13)0.0003 (8)−0.0003 (9)0.0015 (8)
C27A0.0382 (12)0.0241 (11)0.0387 (14)0.0028 (9)0.0097 (10)0.0074 (9)
C28A0.0404 (13)0.0380 (13)0.0497 (15)0.0147 (10)0.0162 (11)0.0136 (11)
C25A0.0304 (11)0.0270 (11)0.0344 (13)0.0037 (9)0.0090 (9)0.0082 (9)
C26A0.0434 (13)0.0420 (13)0.0317 (14)0.0103 (11)0.0042 (10)0.0023 (10)
C23A0.0385 (13)0.0273 (11)0.0381 (14)0.0100 (9)0.0004 (10)0.0057 (9)
C24A0.0422 (13)0.0293 (11)0.0407 (14)0.0063 (10)0.0091 (11)0.0043 (10)
C21A0.0412 (13)0.0285 (11)0.0369 (14)0.0080 (10)0.0114 (10)0.0027 (9)
C22A0.0486 (14)0.0323 (12)0.0336 (14)0.0002 (10)0.0037 (11)−0.0019 (10)
C29A0.0245 (10)0.0243 (10)0.0244 (12)0.0002 (8)0.0025 (8)−0.0001 (8)
C34A0.0260 (10)0.0225 (10)0.0264 (12)0.0027 (8)0.0030 (9)0.0010 (8)
C33A0.0232 (10)0.0270 (10)0.0254 (12)0.0054 (8)0.0018 (8)0.0001 (8)
C32A0.0226 (10)0.0211 (10)0.0320 (13)0.0010 (8)0.0011 (9)−0.0036 (8)
C31A0.0275 (11)0.0218 (10)0.0286 (12)0.0021 (8)0.0048 (9)0.0028 (8)
C30A0.0258 (10)0.0292 (11)0.0264 (12)0.0016 (8)−0.0034 (9)0.0039 (9)
C35A0.0330 (12)0.0283 (11)0.0304 (13)0.0018 (9)0.0009 (9)0.0068 (9)
C36A0.0332 (12)0.0380 (13)0.0480 (15)−0.0121 (10)−0.0067 (11)0.0081 (11)
C37A0.0322 (12)0.0424 (13)0.0659 (18)−0.0087 (10)−0.0017 (12)0.0191 (12)
C29B0.0217 (10)0.0239 (10)0.0232 (11)0.0010 (8)0.0024 (8)0.0026 (8)
C34B0.0238 (10)0.0214 (10)0.0288 (12)0.0024 (8)0.0018 (8)0.0026 (8)
C33B0.0209 (10)0.0246 (10)0.0254 (12)0.0042 (8)0.0016 (8)0.0037 (8)
C32B0.0207 (10)0.0224 (10)0.0238 (12)0.0014 (8)0.0026 (8)−0.0013 (8)
C31B0.0270 (10)0.0203 (10)0.0247 (12)0.0023 (8)0.0046 (8)0.0034 (8)
C30B0.0230 (10)0.0293 (10)0.0228 (12)0.0038 (8)−0.0020 (8)0.0032 (8)
C35B0.0252 (11)0.0242 (10)0.0297 (13)0.0029 (8)0.0030 (9)0.0038 (9)
C36B0.0363 (13)0.0327 (12)0.0479 (15)−0.0137 (10)−0.0092 (11)0.0056 (10)
C37B0.0402 (14)0.0499 (15)0.0739 (19)−0.0140 (12)−0.0099 (13)0.0287 (13)
Geometric parameters (Å, º) top
O1B—C7B1.369 (2)C21B—H21B0.970
O1B—C5B1.377 (2)C22B—H22A0.960
O2B—C20B1.266 (2)C22B—H22B0.960
O3B—C20B1.254 (2)C22B—H22C0.960
O1A—C7A1.366 (2)C9A—C8A1.409 (2)
O1A—C5A1.375 (2)C9A—C10A1.436 (2)
O2A—C20A1.266 (2)C8A—C7A1.382 (2)
O3A—C20A1.255 (2)C8A—H8A0.930
O6A—C33A1.357 (2)C7A—C12A1.414 (2)
O6A—H6AO0.94 (2)C12A—C11A1.412 (2)
O5A—C32A1.356 (2)C12A—C13A1.411 (2)
O5A—H5AO0.92 (2)C11A—C10A1.355 (2)
O4A—C31A1.370 (2)C11A—H11A0.930
O4A—H4AO0.92 (2)C10A—H10A0.930
O7A—C35A1.216 (2)C13A—C4A1.398 (2)
O8A—C35A1.336 (2)C13A—C14A1.495 (2)
O8A—C36A1.455 (2)C4A—C5A1.413 (2)
O6B—C33B1.353 (2)C4A—C3A1.425 (2)
O6B—H6BO0.94 (2)C5A—C6A1.365 (2)
O5B—C32B1.357 (2)C6A—C1A1.422 (2)
O5B—H5BO0.94 (2)C6A—H6A0.930
O4B—C31B1.376 (2)C1A—C2A1.424 (2)
O4B—H4BO0.97 (2)C2A—C3A1.351 (2)
O7B—C35B1.219 (2)C2A—H2A0.930
O8B—C35B1.336 (2)C3A—H3A0.930
O8B—C36B1.449 (2)C14A—C15A1.399 (2)
N2B—C9B1.354 (2)C14A—C19A1.403 (2)
N2B—C27B1.468 (2)C15A—C16A1.386 (3)
N2B—C25B1.480 (2)C15A—H15A0.930
N1B—C1B1.343 (2)C16A—C17A1.385 (2)
N1B—C23B1.477 (2)C16A—H16A0.930
N1B—C21B1.465 (2)C17A—C18A1.390 (2)
N2A—C9A1.356 (2)C17A—H17A0.930
N2A—C27A1.472 (2)C18A—C19A1.392 (2)
N2A—C25A1.469 (2)C18A—H18A0.930
N1A—C1A1.357 (2)C19A—C20A1.509 (2)
N1A—C23A1.471 (2)C27A—C28A1.520 (2)
N1A—C21A1.465 (2)C27A—H27C0.970
C9B—C8B1.410 (2)C27A—H27D0.970
C9B—C10B1.433 (2)C28A—H28D0.960
C8B—C7B1.378 (2)C28A—H28E0.960
C8B—H8B0.930C28A—H28F0.960
C7B—C12B1.411 (2)C25A—C26A1.515 (2)
C12B—C11B1.414 (2)C25A—H25C0.970
C12B—C13B1.416 (2)C25A—H25D0.970
C11B—C10B1.360 (2)C26A—H26D0.960
C11B—H11B0.930C26A—H26E0.960
C10B—H10B0.930C26A—H26F0.960
C13B—C4B1.400 (2)C23A—C24A1.514 (2)
C13B—C14B1.490 (2)C23A—H23C0.970
C4B—C5B1.409 (2)C23A—H23D0.970
C4B—C3B1.427 (2)C24A—H24D0.960
C5B—C6B1.366 (2)C24A—H24E0.960
C6B—C1B1.422 (2)C24A—H24F0.960
C6B—H6B0.930C21A—C22A1.527 (2)
C1B—C2B1.435 (2)C21A—H21C0.970
C2B—C3B1.352 (2)C21A—H21D0.970
C2B—H2B0.930C22A—H22D0.960
C3B—H3B0.930C22A—H22E0.960
C14B—C15B1.397 (2)C22A—H22F0.960
C14B—C19B1.405 (2)C29A—C34A1.390 (2)
C15B—C16B1.377 (2)C29A—C30A1.394 (2)
C15B—H15B0.930C29A—C35A1.479 (2)
C16B—C17B1.386 (2)C34A—C33A1.392 (2)
C16B—H16B0.930C34A—H34A0.930
C17B—C18B1.385 (2)C33A—C32A1.406 (2)
C17B—H17B0.930C32A—C31A1.398 (2)
C18B—C19B1.385 (2)C31A—C30A1.380 (2)
C18B—H18B0.930C30A—H30A0.930
C19B—C20B1.506 (2)C36A—C37A1.492 (3)
C27B—C28B1.521 (2)C36A—H36A0.970
C27B—H27A0.970C36A—H36B0.970
C27B—H27B0.970C37A—H37A0.960
C28B—H28A0.960C37A—H37B0.960
C28B—H28B0.960C37A—H37C0.960
C28B—H28C0.960C29B—C34B1.392 (2)
C25B—C26B1.512 (2)C29B—C30B1.392 (2)
C25B—H25A0.970C29B—C35B1.477 (2)
C25B—H25B0.970C34B—C33B1.390 (2)
C26B—H26A0.960C34B—H34B0.930
C26B—H26B0.960C33B—C32B1.407 (2)
C26B—H26C0.960C32B—C31B1.400 (2)
C23B—C24B1.516 (2)C31B—C30B1.381 (2)
C23B—H23A0.970C30B—H30B0.930
C23B—H23B0.970C36B—C37B1.474 (3)
C24B—H24A0.960C36B—H36C0.970
C24B—H24B0.960C36B—H36D0.970
C24B—H24C0.960C37B—H37D0.960
C21B—C22B1.520 (2)C37B—H37E0.960
C21B—H21A0.970C37B—H37F0.960
O2B···O5B2.5636 (18)O4A···O7Ai2.779 (2)
O3B···O6B2.5811 (17)O7A···O4Ai2.779 (2)
O2A···O5A2.5690 (19)O6B···O3B2.5811 (17)
O3A···O6A2.6303 (17)O5B···O2B2.5636 (18)
O6A···O3A2.6303 (17)O4B···O7Bii2.7957 (19)
O5A···O2A2.5690 (19)O7B···O4Bii2.7957 (19)
C7B—O1B—C5B120.28 (14)C13A—C4A—C3A124.15 (18)
C7A—O1A—C5A120.36 (14)C5A—C4A—C3A115.50 (16)
C33A—O6A—H6AO116.1 (15)O1A—C5A—C4A120.19 (16)
C32A—O5A—H5AO108.2 (14)O1A—C5A—C6A115.71 (17)
C31A—O4A—H4AO112.7 (13)C4A—C5A—C6A124.05 (17)
C35A—O8A—C36A116.30 (15)C5A—C6A—C1A119.04 (18)
C33B—O6B—H6BO117.3 (13)C5A—C6A—H6A120.5
C32B—O5B—H5BO108.4 (14)C1A—C6A—H6A120.5
C31B—O4B—H4BO108.8 (14)N1A—C1A—C6A120.83 (17)
C35B—O8B—C36B116.75 (14)N1A—C1A—C2A121.22 (16)
C9B—N2B—C27B122.96 (16)C6A—C1A—C2A117.94 (16)
C9B—N2B—C25B121.36 (15)C1A—C2A—C3A121.38 (17)
C27B—N2B—C25B115.26 (15)C1A—C2A—H2A119.3
C1B—N1B—C23B123.73 (16)C3A—C2A—H2A119.3
C1B—N1B—C21B121.62 (15)C4A—C3A—C2A121.98 (18)
C23B—N1B—C21B114.30 (15)C4A—C3A—H3A119.0
C9A—N2A—C27A121.28 (16)C2A—C3A—H3A119.0
C9A—N2A—C25A122.30 (15)C13A—C14A—C15A116.74 (16)
C27A—N2A—C25A115.95 (15)C13A—C14A—C19A123.83 (15)
C1A—N1A—C23A121.87 (16)C15A—C14A—C19A119.38 (18)
C1A—N1A—C21A121.48 (15)C14A—C15A—C16A120.74 (18)
C23A—N1A—C21A115.77 (15)C14A—C15A—H15A119.6
N2B—C9B—C8B121.31 (17)C16A—C15A—H15A119.6
N2B—C9B—C10B121.14 (17)C15A—C16A—C17A120.03 (17)
C8B—C9B—C10B117.48 (17)C15A—C16A—H16A120.0
C9B—C8B—C7B119.55 (18)C17A—C16A—H16A120.0
C9B—C8B—H8B120.2C16A—C17A—C18A119.49 (19)
C7B—C8B—H8B120.2C16A—C17A—H17A120.3
O1B—C7B—C8B115.67 (17)C18A—C17A—H17A120.3
O1B—C7B—C12B120.71 (16)C17A—C18A—C19A121.39 (18)
C8B—C7B—C12B123.58 (17)C17A—C18A—H18A119.3
C7B—C12B—C11B115.51 (17)C19A—C18A—H18A119.3
C7B—C12B—C13B119.58 (16)C14A—C19A—C18A118.90 (16)
C11B—C12B—C13B124.90 (18)C14A—C19A—C20A120.64 (17)
C12B—C11B—C10B122.45 (18)C18A—C19A—C20A120.40 (17)
C12B—C11B—H11B118.8O2A—C20A—O3A125.32 (16)
C10B—C11B—H11B118.8O2A—C20A—C19A116.83 (17)
C9B—C10B—C11B120.88 (18)O3A—C20A—C19A117.84 (17)
C9B—C10B—H10B119.6N2A—C27A—C28A113.88 (14)
C11B—C10B—H10B119.5N2A—C27A—H27C108.8
C12B—C13B—C4B118.65 (17)N2A—C27A—H27D108.8
C12B—C13B—C14B119.22 (16)C28A—C27A—H27C108.8
C4B—C13B—C14B121.43 (16)C28A—C27A—H27D108.8
C13B—C4B—C5B120.14 (17)H27C—C27A—H27D107.7
C13B—C4B—C3B124.36 (18)C27A—C28A—H28D109.5
C5B—C4B—C3B115.49 (16)C27A—C28A—H28E109.5
O1B—C5B—C4B120.50 (16)C27A—C28A—H28F109.5
O1B—C5B—C6B115.06 (17)H28D—C28A—H28E109.5
C4B—C5B—C6B124.31 (17)H28D—C28A—H28F109.5
C5B—C6B—C1B119.11 (18)H28E—C28A—H28F109.5
C5B—C6B—H6B120.4N2A—C25A—C26A112.96 (15)
C1B—C6B—H6B120.5N2A—C25A—H25C109.0
N1B—C1B—C6B121.08 (17)N2A—C25A—H25D109.0
N1B—C1B—C2B121.41 (16)C26A—C25A—H25C109.0
C6B—C1B—C2B117.48 (16)C26A—C25A—H25D109.0
C1B—C2B—C3B121.37 (17)H25C—C25A—H25D107.8
C1B—C2B—H2B119.3C25A—C26A—H26D109.5
C3B—C2B—H2B119.3C25A—C26A—H26E109.5
C4B—C3B—C2B121.89 (18)C25A—C26A—H26F109.5
C4B—C3B—H3B119.1H26D—C26A—H26E109.5
C2B—C3B—H3B119.1H26D—C26A—H26F109.5
C13B—C14B—C15B117.01 (16)H26E—C26A—H26F109.5
C13B—C14B—C19B124.05 (16)N1A—C23A—C24A113.03 (16)
C15B—C14B—C19B118.90 (17)N1A—C23A—H23C109.0
C14B—C15B—C16B121.18 (17)N1A—C23A—H23D109.0
C14B—C15B—H15B119.4C24A—C23A—H23C109.0
C16B—C15B—H15B119.4C24A—C23A—H23D109.0
C15B—C16B—C17B119.98 (17)H23C—C23A—H23D107.8
C15B—C16B—H16B120.0C23A—C24A—H24D109.5
C17B—C16B—H16B120.0C23A—C24A—H24E109.5
C16B—C17B—C18B119.23 (19)C23A—C24A—H24F109.5
C16B—C17B—H17B120.4H24D—C24A—H24E109.5
C18B—C17B—H17B120.4H24D—C24A—H24F109.5
C17B—C18B—C19B121.70 (18)H24E—C24A—H24F109.5
C17B—C18B—H18B119.1N1A—C21A—C22A113.73 (17)
C19B—C18B—H18B119.2N1A—C21A—H21C108.8
C14B—C19B—C18B118.97 (16)N1A—C21A—H21D108.8
C14B—C19B—C20B120.97 (17)C22A—C21A—H21C108.8
C18B—C19B—C20B120.06 (16)C22A—C21A—H21D108.8
O2B—C20B—O3B124.95 (16)H21C—C21A—H21D107.7
O2B—C20B—C19B117.26 (16)C21A—C22A—H22D109.5
O3B—C20B—C19B117.78 (16)C21A—C22A—H22E109.5
N2B—C27B—C28B112.09 (15)C21A—C22A—H22F109.5
N2B—C27B—H27A109.2H22D—C22A—H22E109.5
N2B—C27B—H27B109.2H22D—C22A—H22F109.5
C28B—C27B—H27A109.2H22E—C22A—H22F109.5
C28B—C27B—H27B109.2C34A—C29A—C30A119.76 (16)
H27A—C27B—H27B107.9C34A—C29A—C35A122.05 (17)
C27B—C28B—H28A109.5C30A—C29A—C35A118.13 (16)
C27B—C28B—H28B109.5C29A—C34A—C33A120.45 (17)
C27B—C28B—H28C109.5C29A—C34A—H34A119.8
H28A—C28B—H28B109.5C33A—C34A—H34A119.8
H28A—C28B—H28C109.5O6A—C33A—C34A116.93 (16)
H28B—C28B—H28C109.5O6A—C33A—C32A123.01 (15)
N2B—C25B—C26B113.12 (14)C34A—C33A—C32A120.06 (16)
N2B—C25B—H25A109.0O5A—C32A—C33A122.47 (16)
N2B—C25B—H25B109.0O5A—C32A—C31A118.98 (16)
C26B—C25B—H25A109.0C33A—C32A—C31A118.50 (16)
C26B—C25B—H25B109.0O4A—C31A—C32A116.68 (15)
H25A—C25B—H25B107.8O4A—C31A—C30A121.98 (16)
C25B—C26B—H26A109.5C32A—C31A—C30A121.34 (17)
C25B—C26B—H26B109.5C29A—C30A—C31A119.83 (17)
C25B—C26B—H26C109.5C29A—C30A—H30A120.1
H26A—C26B—H26B109.5C31A—C30A—H30A120.1
H26A—C26B—H26C109.5O7A—C35A—O8A122.74 (17)
H26B—C26B—H26C109.5O7A—C35A—C29A124.11 (18)
N1B—C23B—C24B111.32 (15)O8A—C35A—C29A113.15 (16)
N1B—C23B—H23A109.4O8A—C36A—C37A106.78 (16)
N1B—C23B—H23B109.4O8A—C36A—H36A110.4
C24B—C23B—H23A109.4O8A—C36A—H36B110.4
C24B—C23B—H23B109.4C37A—C36A—H36A110.4
H23A—C23B—H23B108.0C37A—C36A—H36B110.4
C23B—C24B—H24A109.5H36A—C36A—H36B108.6
C23B—C24B—H24B109.5C36A—C37A—H37A109.5
C23B—C24B—H24C109.5C36A—C37A—H37B109.5
H24A—C24B—H24B109.5C36A—C37A—H37C109.5
H24A—C24B—H24C109.5H37A—C37A—H37B109.5
H24B—C24B—H24C109.5H37A—C37A—H37C109.5
N1B—C21B—C22B112.00 (17)H37B—C37A—H37C109.5
N1B—C21B—H21A109.2C34B—C29B—C30B119.96 (15)
N1B—C21B—H21B109.2C34B—C29B—C35B121.61 (16)
C22B—C21B—H21A109.2C30B—C29B—C35B118.38 (16)
C22B—C21B—H21B109.2C29B—C34B—C33B120.49 (16)
H21A—C21B—H21B107.9C29B—C34B—H34B119.8
C21B—C22B—H22A109.5C33B—C34B—H34B119.7
C21B—C22B—H22B109.5O6B—C33B—C34B116.78 (16)
C21B—C22B—H22C109.5O6B—C33B—C32B123.26 (15)
H22A—C22B—H22B109.5C34B—C33B—C32B119.95 (16)
H22A—C22B—H22C109.5O5B—C32B—C33B122.60 (16)
H22B—C22B—H22C109.5O5B—C32B—C31B118.89 (16)
N2A—C9A—C8A122.07 (17)C33B—C32B—C31B118.43 (15)
N2A—C9A—C10A120.35 (16)O4B—C31B—C32B116.59 (15)
C8A—C9A—C10A117.58 (17)O4B—C31B—C30B121.92 (16)
C9A—C8A—C7A119.43 (18)C32B—C31B—C30B121.48 (17)
C9A—C8A—H8A120.3C29B—C30B—C31B119.58 (16)
C7A—C8A—H8A120.3C29B—C30B—H30B120.2
O1A—C7A—C8A115.54 (17)C31B—C30B—H30B120.2
O1A—C7A—C12A120.98 (16)O7B—C35B—O8B122.68 (15)
C8A—C7A—C12A123.45 (17)O7B—C35B—C29B124.46 (17)
C7A—C12A—C11A115.86 (17)O8B—C35B—C29B112.86 (15)
C7A—C12A—C13A119.47 (16)O8B—C36B—C37B107.23 (16)
C11A—C12A—C13A124.65 (18)O8B—C36B—H36C110.3
C12A—C11A—C10A122.18 (18)O8B—C36B—H36D110.3
C12A—C11A—H11A118.9C37B—C36B—H36C110.3
C10A—C11A—H11A118.9C37B—C36B—H36D110.3
C9A—C10A—C11A121.38 (17)H36C—C36B—H36D108.5
C9A—C10A—H10A119.3C36B—C37B—H37D109.5
C11A—C10A—H10A119.3C36B—C37B—H37E109.5
C12A—C13A—C4A118.63 (17)C36B—C37B—H37F109.5
C12A—C13A—C14A120.20 (16)H37D—C37B—H37E109.5
C4A—C13A—C14A120.58 (16)H37D—C37B—H37F109.5
C13A—C4A—C5A120.35 (17)H37E—C37B—H37F109.5
C7B—O1B—C5B—C4B−3.1 (2)C14B—C19B—C20B—O3B22.2 (2)
C7B—O1B—C5B—C6B172.93 (14)C18B—C19B—C20B—O2B23.2 (2)
C5B—O1B—C7B—C8B−172.94 (14)C18B—C19B—C20B—O3B−157.74 (17)
C5B—O1B—C7B—C12B4.6 (2)N2A—C9A—C8A—C7A178.73 (16)
C7A—O1A—C5A—C4A−0.4 (2)N2A—C9A—C10A—C11A179.06 (16)
C7A—O1A—C5A—C6A177.32 (14)C8A—C9A—C10A—C11A−1.0 (2)
C5A—O1A—C7A—C8A−178.16 (14)C10A—C9A—C8A—C7A−1.2 (2)
C5A—O1A—C7A—C12A0.2 (2)C9A—C8A—C7A—O1A−177.84 (14)
C35A—O8A—C36A—C37A177.21 (17)C9A—C8A—C7A—C12A3.9 (2)
C36A—O8A—C35A—O7A4.5 (2)O1A—C7A—C12A—C11A177.77 (15)
C36A—O8A—C35A—C29A−175.36 (16)O1A—C7A—C12A—C13A−0.7 (2)
C35B—O8B—C36B—C37B165.84 (17)C8A—C7A—C12A—C11A−4.0 (2)
C36B—O8B—C35B—O7B3.9 (2)C8A—C7A—C12A—C13A177.50 (16)
C36B—O8B—C35B—C29B−175.40 (16)C7A—C12A—C11A—C10A1.7 (2)
C9B—N2B—C27B—C28B−87.6 (2)C7A—C12A—C13A—C4A1.4 (2)
C27B—N2B—C9B—C8B178.66 (15)C7A—C12A—C13A—C14A−169.81 (15)
C27B—N2B—C9B—C10B1.6 (2)C11A—C12A—C13A—C4A−176.87 (16)
C9B—N2B—C25B—C26B−89.2 (2)C11A—C12A—C13A—C14A11.9 (2)
C25B—N2B—C9B—C8B6.5 (2)C13A—C12A—C11A—C10A−179.93 (16)
C25B—N2B—C9B—C10B−170.61 (15)C12A—C11A—C10A—C9A0.7 (2)
C27B—N2B—C25B—C26B98.01 (18)C12A—C13A—C4A—C5A−1.7 (2)
C25B—N2B—C27B—C28B85.0 (2)C12A—C13A—C4A—C3A178.79 (16)
C1B—N1B—C23B—C24B−96.8 (2)C12A—C13A—C14A—C15A81.0 (2)
C23B—N1B—C1B—C6B−175.11 (16)C12A—C13A—C14A—C19A−101.5 (2)
C23B—N1B—C1B—C2B2.8 (2)C4A—C13A—C14A—C15A−90.1 (2)
C1B—N1B—C21B—C22B−79.9 (2)C4A—C13A—C14A—C19A87.4 (2)
C21B—N1B—C1B—C6B−2.3 (2)C14A—C13A—C4A—C5A169.51 (15)
C21B—N1B—C1B—C2B175.63 (16)C14A—C13A—C4A—C3A−10.0 (2)
C23B—N1B—C21B—C22B93.53 (19)C13A—C4A—C5A—O1A1.2 (2)
C21B—N1B—C23B—C24B89.91 (19)C13A—C4A—C5A—C6A−176.33 (16)
C9A—N2A—C27A—C28A−73.2 (2)C13A—C4A—C3A—C2A178.16 (17)
C27A—N2A—C9A—C8A173.33 (15)C5A—C4A—C3A—C2A−1.4 (2)
C27A—N2A—C9A—C10A−6.7 (2)C3A—C4A—C5A—O1A−179.26 (14)
C9A—N2A—C25A—C26A93.2 (2)C3A—C4A—C5A—C6A3.2 (2)
C25A—N2A—C9A—C8A1.5 (2)O1A—C5A—C6A—C1A−179.54 (14)
C25A—N2A—C9A—C10A−178.48 (15)C4A—C5A—C6A—C1A−1.9 (2)
C27A—N2A—C25A—C26A−79.03 (19)C5A—C6A—C1A—N1A177.70 (16)
C25A—N2A—C27A—C28A99.11 (19)C5A—C6A—C1A—C2A−1.3 (2)
C1A—N1A—C23A—C24A93.3 (2)N1A—C1A—C2A—C3A−175.92 (16)
C23A—N1A—C1A—C6A178.26 (15)C6A—C1A—C2A—C3A3.0 (2)
C23A—N1A—C1A—C2A−2.8 (2)C1A—C2A—C3A—C4A−1.7 (2)
C1A—N1A—C21A—C22A−66.2 (2)C13A—C14A—C15A—C16A179.23 (17)
C21A—N1A—C1A—C6A−13.0 (2)C13A—C14A—C19A—C18A179.76 (17)
C21A—N1A—C1A—C2A165.94 (16)C13A—C14A—C19A—C20A−2.8 (2)
C23A—N1A—C21A—C22A103.19 (18)C15A—C14A—C19A—C18A−2.7 (2)
C21A—N1A—C23A—C24A−76.1 (2)C15A—C14A—C19A—C20A174.71 (16)
N2B—C9B—C8B—C7B−170.64 (16)C19A—C14A—C15A—C16A1.6 (2)
N2B—C9B—C10B—C11B170.33 (16)C14A—C15A—C16A—C17A0.9 (2)
C8B—C9B—C10B—C11B−6.9 (2)C15A—C16A—C17A—C18A−2.1 (2)
C10B—C9B—C8B—C7B6.5 (2)C16A—C17A—C18A—C19A0.9 (2)
C9B—C8B—C7B—O1B176.91 (14)C17A—C18A—C19A—C14A1.5 (2)
C9B—C8B—C7B—C12B−0.5 (2)C17A—C18A—C19A—C20A−175.93 (16)
O1B—C7B—C12B—C11B177.48 (14)C14A—C19A—C20A—O2A−163.72 (16)
O1B—C7B—C12B—C13B−3.7 (2)C14A—C19A—C20A—O3A15.0 (2)
C8B—C7B—C12B—C11B−5.2 (2)C18A—C19A—C20A—O2A13.7 (2)
C8B—C7B—C12B—C13B173.66 (16)C18A—C19A—C20A—O3A−167.57 (16)
C7B—C12B—C11B—C10B4.9 (2)C34A—C29A—C30A—C31A−1.2 (2)
C7B—C12B—C13B—C4B1.2 (2)C30A—C29A—C34A—C33A−0.6 (2)
C7B—C12B—C13B—C14B−169.33 (15)C34A—C29A—C35A—O7A−174.4 (2)
C11B—C12B—C13B—C4B179.95 (14)C34A—C29A—C35A—O8A5.5 (2)
C11B—C12B—C13B—C14B9.4 (2)C35A—C29A—C34A—C33A176.44 (18)
C13B—C12B—C11B—C10B−173.88 (17)C30A—C29A—C35A—O7A2.7 (3)
C12B—C11B—C10B—C9B1.0 (2)C30A—C29A—C35A—O8A−177.43 (17)
C12B—C13B—C4B—C5B0.3 (2)C35A—C29A—C30A—C31A−178.35 (18)
C12B—C13B—C4B—C3B−178.75 (16)C29A—C34A—C33A—O6A−177.54 (17)
C12B—C13B—C14B—C15B69.8 (2)C29A—C34A—C33A—C32A2.6 (2)
C12B—C13B—C14B—C19B−112.6 (2)O6A—C33A—C32A—O5A0.0 (2)
C4B—C13B—C14B—C15B−100.5 (2)O6A—C33A—C32A—C31A177.44 (17)
C4B—C13B—C14B—C19B77.1 (2)C34A—C33A—C32A—O5A179.93 (17)
C14B—C13B—C4B—C5B170.59 (15)C34A—C33A—C32A—C31A−2.7 (2)
C14B—C13B—C4B—C3B−8.4 (2)O5A—C32A—C31A—O4A−1.6 (2)
C13B—C4B—C5B—O1B0.6 (2)O5A—C32A—C31A—C30A178.38 (18)
C13B—C4B—C5B—C6B−174.98 (16)C33A—C32A—C31A—O4A−179.07 (17)
C13B—C4B—C3B—C2B176.06 (16)C33A—C32A—C31A—C30A0.9 (2)
C5B—C4B—C3B—C2B−3.0 (2)O4A—C31A—C30A—C29A−179.02 (17)
C3B—C4B—C5B—O1B179.72 (14)C32A—C31A—C30A—C29A1.0 (3)
C3B—C4B—C5B—C6B4.1 (2)C34B—C29B—C30B—C31B−0.7 (2)
O1B—C5B—C6B—C1B−175.98 (14)C30B—C29B—C34B—C33B−0.0 (2)
C4B—C5B—C6B—C1B−0.2 (2)C34B—C29B—C35B—O7B175.68 (19)
C5B—C6B—C1B—N1B173.16 (16)C34B—C29B—C35B—O8B−5.0 (2)
C5B—C6B—C1B—C2B−4.8 (2)C35B—C29B—C34B—C33B177.35 (18)
N1B—C1B—C2B—C3B−172.05 (16)C30B—C29B—C35B—O7B−6.9 (3)
C6B—C1B—C2B—C3B5.9 (2)C30B—C29B—C35B—O8B172.40 (17)
C1B—C2B—C3B—C4B−2.0 (2)C35B—C29B—C30B—C31B−178.20 (18)
C13B—C14B—C15B—C16B179.90 (16)C29B—C34B—C33B—O6B−177.61 (17)
C13B—C14B—C19B—C18B−179.28 (16)C29B—C34B—C33B—C32B2.5 (2)
C13B—C14B—C19B—C20B0.8 (2)O6B—C33B—C32B—O5B−0.6 (3)
C15B—C14B—C19B—C18B−1.7 (2)O6B—C33B—C32B—C31B176.04 (18)
C15B—C14B—C19B—C20B178.41 (16)C34B—C33B—C32B—O5B179.29 (18)
C19B—C14B—C15B—C16B2.1 (2)C34B—C33B—C32B—C31B−4.0 (2)
C14B—C15B—C16B—C17B−0.8 (2)O5B—C32B—C31B—O4B1.3 (2)
C15B—C16B—C17B—C18B−1.0 (2)O5B—C32B—C31B—C30B−179.88 (18)
C16B—C17B—C18B—C19B1.4 (2)C33B—C32B—C31B—O4B−175.53 (17)
C17B—C18B—C19B—C14B−0.1 (2)C33B—C32B—C31B—C30B3.3 (2)
C17B—C18B—C19B—C20B179.85 (16)O4B—C31B—C30B—C29B177.84 (18)
C14B—C19B—C20B—O2B−156.93 (16)C32B—C31B—C30B—C29B−0.9 (3)
Symmetry codes: (i) −x+3, −y+1, −z+1; (ii) −x+3, −y+2, −z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6A—H6AO···O2A0.94 (2)2.72 (2)3.4413 (18)133.8 (18)
O6A—H6AO···O3A0.94 (2)1.72 (2)2.6303 (17)162 (2)
O6A—H6AO···O5A0.94 (2)2.53 (2)2.8733 (19)102.2 (17)
O5A—H5AO···O2A0.92 (2)1.66 (2)2.5690 (19)167 (2)
O5A—H5AO···O3A0.92 (2)2.62 (2)3.1884 (18)120.4 (18)
O4A—H4AO···O7Ai0.92 (2)1.86 (2)2.779 (2)178.8 (10)
O6B—H6BO···O2B0.94 (2)2.72 (2)3.4156 (18)131.4 (16)
O6B—H6BO···O3B0.94 (2)1.68 (2)2.5811 (17)159 (2)
O6B—H6BO···O5B0.94 (2)2.55 (2)2.8799 (19)101.0 (15)
O5B—H5BO···O2B0.94 (2)1.64 (2)2.5636 (18)166 (2)
O5B—H5BO···O3B0.94 (2)2.66 (2)3.2473 (18)121.5 (19)
O4B—H4BO···O7Bii0.97 (2)1.83 (2)2.7957 (19)175 (2)
Symmetry codes: (i) −x+3, −y+1, −z+1; (ii) −x+3, −y+2, −z+2.

Experimental details

Crystal data
Chemical formulaC28H30N2O3·C9H10O5
Mr640.71
Crystal system, space groupTriclinic, P1
Temperature (K)93
a, b, c (Å)11.3689 (2), 16.3654 (3), 17.6518 (3)
α, β, γ (°)94.1760 (7), 96.1440 (7), 93.7790 (7)
V (Å3)3247.69 (10)
Z4
Radiation typeCu Kα
µ (mm−1)0.76
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(Higashi, 1995)
Tmin, Tmax0.810, 0.860
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections		29633, 11011, 7318
Rint0.039
(sin θ/λ)max (Å−1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.115, 0.94
No. of reflections11011
No. of parameters881
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.23, −0.25

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2006), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6A—H6AO···O2A0.94 (2)2.72 (2)3.4413 (18)133.8 (18)
O6A—H6AO···O3A0.94 (2)1.72 (2)2.6303 (17)162 (2)
O6A—H6AO···O5A0.94 (2)2.53 (2)2.8733 (19)102.2 (17)
O5A—H5AO···O2A0.92 (2)1.66 (2)2.5690 (19)167 (2)
O5A—H5AO···O3A0.92 (2)2.62 (2)3.1884 (18)120.4 (18)
O4A—H4AO···O7Ai0.92 (2)1.86 (2)2.779 (2)178.8 (10)
O6B—H6BO···O2B0.94 (2)2.72 (2)3.4156 (18)131.4 (16)
O6B—H6BO···O3B0.94 (2)1.68 (2)2.5811 (17)159 (2)
O6B—H6BO···O5B0.94 (2)2.55 (2)2.8799 (19)101.0 (15)
O5B—H5BO···O2B0.94 (2)1.64 (2)2.5636 (18)166 (2)
O5B—H5BO···O3B0.94 (2)2.66 (2)3.2473 (18)121.5 (19)
O4B—H4BO···O7Bii0.97 (2)1.83 (2)2.7957 (19)175 (2)
Symmetry codes: (i) −x+3, −y+1, −z+1; (ii) −x+3, −y+2, −z+2.
 

Acknowledgements

The author acknowledges Mr K. Sato for experimental assistance.

References

First citationBurla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388.  Web of Science CrossRef CAS 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 citationHitachi, A., Makino, T., Iwata, S. & Mizuguchi, J. (2005). Acta Cryst. E61, o2590–o2592.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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 First citationMuthyala, R. (1997). Chemistry and Applications of Leuco Dyes. New York, London: Plenum Press.  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 citationSekiguchi, Y., Takayama, S., Gotanda, T. & Sano, K. (2007). Chem. Lett. 36, 1010–1011.  Web of Science CSD CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 64| Part 7| July 2008| Pages o1238-o1239
doi:10.1107/S1600536808016528
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