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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 68| Part 2| February 2012| Page o535
doi:10.1107/S1600536812002905

1-[Amino­(4-chloro­phen­yl)meth­yl]-6-bromo­naphthalen-2-ol

A. S. Praveen,a H. S. Yathirajan,a* William T. A. Harrisonb and Alexandra M. Z. Slawinc

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, bDepartment of Chemistry, University of Aberdeen, Aberdeen AB24 3UE, Scotland, and cSchool of Chemistry, University of St Andrews, St Andrews KY16 9ST, Scotland
*Correspondence e-mail: yathirajan@hotmail.com

(Received 16 January 2012; accepted 23 January 2012; online 31 January 2012)

In the title compound, C17H13BrClNO, the dihedral angle between the naphthol ring system and the chloro­benzene ring is 76.59 (11)°. This twisted conformation is supported by an intra­molecular O—H⋯N hydrogen bond. In the crystal, [100] chains arise, with adjacent mol­ecules linked by an N—H⋯O hydrogen bond, a C—H⋯π inter­action and an aromatic π–π stacking contact [centroid-to-centroid separation = 3.783 (2) Å]. Weak C—H⋯O inter­actions also occur.

Related literature

For related naphthol–oxazine derivatives and their anti­microbial activity, see: Mayekar et al. (2011[Mayekar, A. N., Yathirajan, H. S., Narayana, B., Sarojini, B. K., Suchetha Kumari, N. & Harrison, W. T. A. (2011). Int. J. Chem. 3, 74-86.]).

[Scheme 1]

Experimental

Crystal data

  • C17H13BrClNO

  • Mr = 361.64

  • Triclinic, [P \overline 1]

  • a = 4.8026 (15) Å

  • b = 10.785 (3) Å

  • c = 15.086 (4) Å

  • α = 67.64 (2)°

  • β = 79.43 (2)°

  • γ = 85.32 (2)°

  • V = 710.3 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 3.08 mm−1

  • T = 73 K

  • 0.12 × 0.10 × 0.10 mm
Data collection

  • Rigaku Mercury CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2009[Rigaku (2009). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.709, Tmax = 0.748

  • 4392 measured reflections

  • 2426 independent reflections

  • 2222 reflections with I > 2σ(I)

  • Rint = 0.043
Refinement

  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.082

  • S = 1.05

  • 2426 reflections

  • 199 parameters

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

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.42 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12–C17 benzene ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1O⋯N1 0.90 (3) 1.76 (3) 2.601 (3) 155 (3)
N1—H2N⋯O1i 0.84 (3) 2.26 (3) 3.043 (3) 155 (3)
C8—H8⋯O1ii 0.95 2.57 3.510 (4) 171
C11—H11⋯Cg1i 1.00 2.80 3.682 (3) 148
Symmetry codes: (i) x+1, y, z; (ii) -x-1, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2009[Rigaku (2009). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812002905/bq2335sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812002905/bq2335Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812002905/bq2335Isup3.cml

checkCIF report


Comment top

As part of our ongoing studies of naphthol–oxazines (Mayekar et al., 2011), we now describe the synthesis and crystal structure of the title compound, (I), (Fig. 1).

The naphthol ring system (C1–C10) in (I) is almost planar (r.m.s. deviation = 0.007 Å) and the Br atom deviates from the mean plane by 0.012 (1) Å. The dihedral angle between the naphthol and chlorobenzene rings is 76.59 (11)°. Atom C11 is a stereogenic centre: in the arbitrarily chosen asymmetric molecule, it has R configuration, but crystal symmetry generates a racemic mixture. The C1—C10—C11—C12 torsion angle is 100.0 (3)° and the twisted conformation of the molecule is supported by an intramolecular O—H···N hydrogen bond (Table 1).

In the crystal, the molecules are linked into [100] chains (Fig. 2), with adjacent molecules linked by an N—H···O hydrogen bond, a C—H···π interaction and a weak π–π stacking contact [centroid–centroid separation = 3.783 (2) Å] between the phenol and bromobenzene rings. A weak C—H···O interaction also occur.

Related literature top

For related naphthol–oxazine derivatives and their antimicrobial activity, see: Mayekar et al. (2011).

Experimental top

8-Bromo-1,3-bis(4-chlorophenyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine (1 mmol) (Mayekar et al., 2011), was suspended in 20% HCl (20 ml) and the mixture was stirred and refluxed for 6 h, whereby the crystalline hydrochloride salt separated out, which was filtered off and washed with ethyl acetate. The solid was suspended in water and the mixture was treated with conc. NH4OH (3 ml) and extracted with ethyl acetate. After drying (over anhydrous Na2SO4) and evaporation of the solvent, the crude product was obtained, which was further purified by recrystallization. Colourless prisms of (I) were grown from the slow evaporation of an ethyl acetate solution (M.p. 413–415 K). Anal. Calcd. for C17H13BrClNO: C 56.30; H 3.61; N 3.86%; Found: C 56.26; H 3.63; N 3.81%.

Refinement top

The N- and O-bound H atoms were located in a difference map. Their positions were freely refined with the constraint Uiso(H) = 1.2Ueq(N,O) applied. The C-bound H atoms were geometrically placed (C—H = 0.95 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku, 2009); cell refinement: CrystalClear (Rigaku, 2009); data reduction: CrystalClear (Rigaku, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids for non-H atoms. The O—H···N hydrogen bond is indicated by a double-dashed line.
[Figure 2] Fig. 2. Part of a [100] chain of molecules linked by N—H···O hydrogen bonds (double dashed lines), C—H···π interactions (blue open lines) and aromatic π–π stacking interactions (pink open lines). F1 is the centroid of the C1–C6 ring, F2 is the centroid of the C1/C6–C10 ring and F3 is the centroid of the C12–C17 ring. Atoms with a * suffix are at the symmetry position (x + 1, y, z).
1-[Amino(4-chlorophenyl)methyl]-6-bromonaphthalen-2-ol top
Crystal data top
C17H13BrClNOZ = 2
Mr = 361.64F(000) = 364
Triclinic, P1Dx = 1.691 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.8026 (15) ÅCell parameters from 2706 reflections
b = 10.785 (3) Åθ = 2.0–28.5°
c = 15.086 (4) ŵ = 3.08 mm−1
α = 67.64 (2)°T = 73 K
β = 79.43 (2)°Prism, colourless
γ = 85.32 (2)°0.12 × 0.10 × 0.10 mm
V = 710.3 (4) Å3
Data collection top
Rigaku Mercury CCD
diffractometer		2426 independent reflections
Radiation source: fine-focus sealed tube2222 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2009)		h = −5→4
Tmin = 0.709, Tmax = 0.748k = −12→10
4392 measured reflectionsl = −17→17
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0351P)2]
where P = (Fo2 + 2Fc2)/3
2426 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.39 e Å−3
0 restraintsΔρmin = −0.42 e Å−3
Crystal data top
C17H13BrClNOγ = 85.32 (2)°
Mr = 361.64V = 710.3 (4) Å3
Triclinic, P1Z = 2
a = 4.8026 (15) ÅMo Kα radiation
b = 10.785 (3) ŵ = 3.08 mm−1
c = 15.086 (4) ÅT = 73 K
α = 67.64 (2)°0.12 × 0.10 × 0.10 mm
β = 79.43 (2)°
Data collection top
Rigaku Mercury CCD
diffractometer		2426 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2009)		2222 reflections with I > 2σ(I)
Tmin = 0.709, Tmax = 0.748Rint = 0.043
4392 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.39 e Å−3
2426 reflectionsΔρmin = −0.42 e Å−3
199 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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*/Ueq
C10.3027 (6)0.3901 (3)0.3133 (2)0.0134 (6)
C20.5552 (6)0.3781 (3)0.2503 (2)0.0145 (6)
H20.64130.45710.20200.017*
C30.6762 (6)0.2570 (3)0.2573 (2)0.0173 (6)
H30.84470.25190.21450.021*
C40.5505 (6)0.1395 (3)0.3281 (2)0.0166 (6)
C50.3108 (6)0.1435 (3)0.3906 (2)0.0169 (6)
H50.22970.06260.43800.020*
C60.1816 (6)0.2684 (3)0.3853 (2)0.0151 (6)
C7−0.0704 (6)0.2745 (3)0.4498 (2)0.0164 (6)
H7−0.15290.19380.49690.020*
C8−0.1952 (6)0.3941 (3)0.4448 (2)0.0162 (6)
H8−0.36440.39660.48810.019*
C9−0.0740 (6)0.5139 (3)0.3759 (2)0.0142 (6)
C100.1691 (6)0.5154 (3)0.3095 (2)0.0130 (6)
C110.2826 (6)0.6491 (3)0.2339 (2)0.0145 (6)
H110.48490.63600.20760.017*
C120.1154 (5)0.7008 (3)0.1501 (2)0.0131 (6)
C130.1219 (6)0.6284 (3)0.0903 (2)0.0190 (7)
H130.22850.54700.10350.023*
C14−0.0228 (6)0.6719 (3)0.0123 (2)0.0208 (7)
H14−0.01590.6213−0.02760.025*
C15−0.1785 (6)0.7909 (3)−0.0065 (2)0.0177 (6)
C16−0.1916 (6)0.8636 (3)0.0518 (2)0.0177 (7)
H16−0.30050.94430.03890.021*
C17−0.0441 (6)0.8183 (3)0.1297 (2)0.0161 (6)
H17−0.05300.86890.16980.019*
Cl1−0.35388 (15)0.84899 (8)−0.10638 (5)0.0249 (2)
Br10.72536 (6)−0.02865 (3)0.33594 (2)0.02405 (14)
O1−0.2084 (4)0.6319 (2)0.37570 (15)0.0169 (5)
H1O−0.070 (6)0.692 (3)0.345 (2)0.020*
N10.2704 (5)0.7469 (3)0.2819 (2)0.0165 (5)
H1N0.322 (6)0.827 (3)0.240 (2)0.020*
H2N0.387 (6)0.725 (3)0.321 (2)0.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0138 (14)0.0130 (14)0.0145 (16)−0.0014 (12)−0.0055 (12)−0.0047 (12)
C20.0184 (15)0.0143 (15)0.0103 (15)−0.0028 (12)−0.0043 (12)−0.0025 (12)
C30.0168 (15)0.0195 (15)0.0168 (17)0.0000 (13)−0.0032 (12)−0.0079 (13)
C40.0187 (15)0.0134 (14)0.0200 (17)0.0031 (12)−0.0079 (13)−0.0073 (13)
C50.0197 (16)0.0143 (14)0.0172 (17)−0.0024 (12)−0.0062 (13)−0.0048 (13)
C60.0190 (15)0.0143 (14)0.0126 (16)−0.0024 (12)−0.0059 (12)−0.0037 (13)
C70.0160 (15)0.0181 (15)0.0122 (16)−0.0037 (12)−0.0034 (12)−0.0014 (13)
C80.0126 (14)0.0232 (16)0.0126 (16)−0.0020 (13)−0.0019 (12)−0.0063 (13)
C90.0136 (14)0.0145 (14)0.0155 (16)0.0029 (12)−0.0071 (12)−0.0054 (13)
C100.0143 (14)0.0104 (13)0.0137 (15)0.0002 (11)−0.0062 (12)−0.0024 (12)
C110.0134 (14)0.0119 (14)0.0189 (16)0.0003 (12)−0.0034 (12)−0.0062 (13)
C120.0092 (14)0.0123 (14)0.0114 (15)−0.0044 (11)0.0029 (11)0.0014 (12)
C130.0210 (16)0.0148 (15)0.0186 (17)−0.0001 (13)−0.0045 (13)−0.0029 (13)
C140.0252 (17)0.0189 (16)0.0172 (17)−0.0056 (14)0.0001 (13)−0.0064 (14)
C150.0127 (14)0.0241 (16)0.0128 (16)−0.0036 (12)−0.0036 (12)−0.0017 (13)
C160.0136 (15)0.0161 (15)0.0211 (18)0.0006 (12)−0.0021 (12)−0.0051 (13)
C170.0157 (15)0.0162 (15)0.0168 (16)−0.0024 (12)−0.0019 (12)−0.0065 (13)
Cl10.0262 (4)0.0295 (4)0.0186 (4)0.0006 (4)−0.0098 (3)−0.0059 (4)
Br10.0327 (2)0.01573 (19)0.0253 (2)0.00657 (14)−0.00654 (15)−0.00993 (15)
O10.0136 (10)0.0140 (10)0.0218 (12)0.0029 (8)−0.0019 (9)−0.0063 (9)
N10.0194 (14)0.0112 (12)0.0198 (15)0.0006 (11)−0.0084 (11)−0.0047 (11)
Geometric parameters (Å, º) top
C1—C21.427 (4)C10—C111.525 (4)
C1—C61.432 (4)C11—N11.482 (3)
C1—C101.434 (4)C11—C121.522 (4)
C2—C31.360 (4)C11—H111.0000
C2—H20.9500C12—C171.385 (4)
C3—C41.403 (4)C12—C131.395 (4)
C3—H30.9500C13—C141.384 (4)
C4—C51.357 (4)C13—H130.9500
C4—Br11.906 (3)C14—C151.390 (4)
C5—C61.416 (4)C14—H140.9500
C5—H50.9500C15—C161.374 (4)
C6—C71.421 (4)C15—Cl11.741 (3)
C7—C81.359 (4)C16—C171.391 (4)
C7—H70.9500C16—H160.9500
C8—C91.403 (4)C17—H170.9500
C8—H80.9500O1—H1O0.90 (3)
C9—O11.378 (3)N1—H1N0.88 (3)
C9—C101.388 (4)N1—H2N0.84 (3)
C2—C1—C6117.0 (2)C1—C10—C11122.0 (2)
C2—C1—C10124.0 (3)N1—C11—C12110.7 (2)
C6—C1—C10118.9 (2)N1—C11—C10108.7 (2)
C3—C2—C1122.0 (3)C12—C11—C10111.4 (2)
C3—C2—H2119.0N1—C11—H11108.6
C1—C2—H2119.0C12—C11—H11108.6
C2—C3—C4119.6 (3)C10—C11—H11108.6
C2—C3—H3120.2C17—C12—C13117.9 (3)
C4—C3—H3120.2C17—C12—C11122.8 (2)
C5—C4—C3121.6 (3)C13—C12—C11119.4 (2)
C5—C4—Br1119.9 (2)C14—C13—C12121.7 (3)
C3—C4—Br1118.5 (2)C14—C13—H13119.1
C4—C5—C6120.0 (3)C12—C13—H13119.1
C4—C5—H5120.0C13—C14—C15118.8 (3)
C6—C5—H5120.0C13—C14—H14120.6
C5—C6—C7120.8 (3)C15—C14—H14120.6
C5—C6—C1119.9 (2)C16—C15—C14120.7 (3)
C7—C6—C1119.3 (2)C16—C15—Cl1120.0 (2)
C8—C7—C6120.9 (3)C14—C15—Cl1119.3 (2)
C8—C7—H7119.5C15—C16—C17119.5 (3)
C6—C7—H7119.5C15—C16—H16120.2
C7—C8—C9120.0 (2)C17—C16—H16120.2
C7—C8—H8120.0C12—C17—C16121.3 (3)
C9—C8—H8120.0C12—C17—H17119.3
O1—C9—C10120.7 (3)C16—C17—H17119.3
O1—C9—C8117.1 (2)C9—O1—H1O102.5 (18)
C10—C9—C8122.2 (2)C11—N1—H1N112 (2)
C9—C10—C1118.6 (3)C11—N1—H2N110 (2)
C9—C10—C11119.4 (2)H1N—N1—H2N105 (3)
C6—C1—C2—C30.4 (4)C2—C1—C10—C9−179.1 (3)
C10—C1—C2—C3179.3 (3)C6—C1—C10—C9−0.2 (4)
C1—C2—C3—C40.2 (4)C2—C1—C10—C112.1 (4)
C2—C3—C4—C5−0.4 (4)C6—C1—C10—C11−179.0 (2)
C2—C3—C4—Br1180.0 (2)C9—C10—C11—N143.5 (3)
C3—C4—C5—C60.0 (4)C1—C10—C11—N1−137.8 (3)
Br1—C4—C5—C6179.6 (2)C9—C10—C11—C12−78.8 (3)
C4—C5—C6—C7179.6 (3)C1—C10—C11—C12100.0 (3)
C4—C5—C6—C10.6 (4)N1—C11—C12—C17−5.3 (4)
C2—C1—C6—C5−0.8 (4)C10—C11—C12—C17115.8 (3)
C10—C1—C6—C5−179.8 (2)N1—C11—C12—C13174.4 (2)
C2—C1—C6—C7−179.7 (2)C10—C11—C12—C13−64.5 (3)
C10—C1—C6—C71.3 (4)C17—C12—C13—C140.7 (4)
C5—C6—C7—C8−179.9 (3)C11—C12—C13—C14−179.1 (3)
C1—C6—C7—C8−1.0 (4)C12—C13—C14—C150.0 (4)
C6—C7—C8—C9−0.5 (4)C13—C14—C15—C16−0.7 (4)
C7—C8—C9—O1−179.0 (2)C13—C14—C15—Cl1178.3 (2)
C7—C8—C9—C101.6 (4)C14—C15—C16—C170.8 (4)
O1—C9—C10—C1179.3 (2)Cl1—C15—C16—C17−178.2 (2)
C8—C9—C10—C1−1.3 (4)C13—C12—C17—C16−0.5 (4)
O1—C9—C10—C11−1.9 (4)C11—C12—C17—C16179.2 (3)
C8—C9—C10—C11177.5 (2)C15—C16—C17—C12−0.2 (4)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C12–C17 benzene ring.
D—H···AD—HH···AD···AD—H···A
O1—H1O···N10.90 (3)1.76 (3)2.601 (3)155 (3)
N1—H2N···O1i0.84 (3)2.26 (3)3.043 (3)155 (3)
C8—H8···O1ii0.952.573.510 (4)171
C11—H11···Cg1i1.002.803.682 (3)148
Symmetry codes: (i) x+1, y, z; (ii) −x−1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC17H13BrClNO
Mr361.64
Crystal system, space groupTriclinic, P1
Temperature (K)73
a, b, c (Å)4.8026 (15), 10.785 (3), 15.086 (4)
α, β, γ (°)67.64 (2), 79.43 (2), 85.32 (2)
V (Å3)710.3 (4)
Z2
Radiation typeMo Kα
µ (mm−1)3.08
Crystal size (mm)0.12 × 0.10 × 0.10
Data collection
DiffractometerRigaku Mercury CCD
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2009)
Tmin, Tmax0.709, 0.748
No. of measured, independent and
observed [I > 2σ(I)] reflections		4392, 2426, 2222
Rint0.043
(sin θ/λ)max (Å−1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.082, 1.05
No. of reflections2426
No. of parameters199
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.39, −0.42

Computer programs: CrystalClear (Rigaku, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C12–C17 benzene ring.
D—H···AD—HH···AD···AD—H···A
O1—H1O···N10.90 (3)1.76 (3)2.601 (3)155 (3)
N1—H2N···O1i0.84 (3)2.26 (3)3.043 (3)155 (3)
C8—H8···O1ii0.952.573.510 (4)171
C11—H11···Cg1i1.002.803.682 (3)148
Symmetry codes: (i) x+1, y, z; (ii) −x−1, −y+1, −z+1.
 

Acknowledgements

ASP thanks the University of Mysore for research facilities.

References

First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationMayekar, A. N., Yathirajan, H. S., Narayana, B., Sarojini, B. K., Suchetha Kumari, N. & Harrison, W. T. A. (2011). Int. J. Chem. 3, 74–86.  CrossRef CAS Google Scholar
 First citationRigaku (2009). CrystalClear. Rigaku Corporation, Tokyo, Japan.  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 68| Part 2| February 2012| Page o535
doi:10.1107/S1600536812002905
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