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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 71| Part 6| June 2015| Page o429
doi:10.1107/S205698901500955X

Crystal structure of oryzalin

Gihaeng Kang,a Jineun Kim,a* Youngeun Jeona and Tae Ho Kima*

aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
*Correspondence e-mail: thkim@gnu.ac.kr, jekim@gnu.ac.kr

Edited by J. Simpson, University of Otago, New Zealand (Received 12 May 2015; accepted 19 May 2015; online 30 May 2015)

The title compound, C12H18N4O6S (systematic name: 4-di­propyl­amino-3,5-di­nitro­benzene­sulfonamide), is a sulfonamide with herbicidal properties marketed as oryzalin. The dihedral angles between the benzene ring and the mean planes of the nitro groups are 26.15 (11) and 54.80 (9)°. The propyl arms of the di­propyl­amino substituent lie on opposite sides of this ring plane. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds generate a three-dimensional network.

CCDC reference: 1401628

1. Related literature

For information on the toxicity and herbicidal properties of the title compound, see: Naqvi & Leung (1983[Naqvi, S. M. & Leung, T.-S. (1983). Bull. Environ. Contam. Toxicol. 31, 304-308.]). For related crystal structures, see: O'Connell & Maslen (1967[O'Connell, A. M. & Maslen, E. N. (1967). Acta Cryst. 22, 134-145.]); Tremayne et al. (2002[Tremayne, M., Seaton, C. C. & Glidewell, C. (2002). Acta Cryst. B58, 823-834.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C12H18N4O6S

  • Mr = 346.36

  • Triclinic, [P \overline 1]

  • a = 7.6057 (2) Å

  • b = 8.2463 (2) Å

  • c = 12.8657 (2) Å

  • α = 73.901 (1)°

  • β = 86.059 (1)°

  • γ = 83.549 (1)°

  • V = 769.77 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.25 mm−1

  • T = 173 K

  • 0.49 × 0.17 × 0.05 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.888, Tmax = 0.988

  • 14199 measured reflections

  • 3778 independent reflections

  • 3506 reflections with I > 2σ(I)

  • Rint = 0.021

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.090

  • S = 1.05

  • 3778 reflections

  • 218 parameters

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

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.42 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H2N⋯O6i 0.86 (2) 2.529 (19) 2.9956 (15) 114.9 (15)
N1—H2N⋯O2ii 0.86 (2) 2.26 (2) 3.0839 (16) 160.5 (17)
N1—H1N⋯O3iii 0.81 (2) 2.15 (2) 2.9474 (16) 170.0 (19)
C2—H2⋯N1ii 0.95 2.74 3.6843 (17) 171
C9—H9A⋯O4iv 0.98 2.69 3.3192 (18) 122
C10—H10A⋯O2v 0.99 2.59 3.4033 (15) 140
C12—H12C⋯O3vi 0.98 2.71 3.249 (2) 115
C12—H12A⋯O5vii 0.98 2.61 3.492 (2) 150
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y-1, -z+2; (iii) x-1, y, z; (iv) -x+2, -y, -z+1; (v) -x+1, -y, -z+2; (vi) x, y+1, z; (vii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1401628

Crystal structure: contains datablocks global, I. DOI: 10.1107/S205698901500955X/sj5462sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S205698901500955X/sj5462Isup2.hkl

Supporting information file. DOI: 10.1107/S205698901500955X/sj5462Isup3.cml

checkCIF report


Comment top

Oryzalin, C12H18N4O6S, is a sulfonamide herbicide for soybean and crop weeds (Naqvi & Leung, 1983). Its crystal structure is reported herein. In this compound (Scheme 1, Fig. 1), the dihedral angles between the central phenyl ring and the mean planes of two nitro groups are 26.15 (11) and 54.80 (9)°, respectively. All bond lengths and bond angles are normal and comparable to those observed in the crystal structures of similar compounds (O'Connell & Maslen, 1967; Tremayne et al., 2002).

In the crystal structure (Fig. 2), the crystal structure is stabilized by intermolecular N—H···O and C—H···O hydrogen bonds (Table 1), resulting in a three-dimensional architechture.

Related literature top

For information on the toxicity and herbicidal properties of the title compound, see: Naqvi & Leung (1983). For related crystal structures, see: O'Connell & Maslen (1967); Tremayne et al. (2002).

Experimental top

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH2Cl2 gave single crystals suitable for X-ray analysis.

Refinement top

The N-bound H atoms were located in a difference Fourier map and freely refined (N—H = 0.81 (2) - 0.86 (2) Å). The C-bound H atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.98 Å, Uiso = 1.2Ueq(C) for methyl group, d(C—H) = 0.99 Å, Uiso = 1.2Ueq(C) for Csp3—H, and d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for aromatic C—H.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.
[Figure 2] Fig. 2. Crystal packing viewed along the a axis. The intermolecular N—H···O and C—H···O hydrogen bonds are shown as dashed lines.
4-Dipropylamino-3,5-dinitrobenzenesulfonamide top
Crystal data top
C12H18N4O6SZ = 2
Mr = 346.36F(000) = 364
Triclinic, P1Dx = 1.494 Mg m−3
a = 7.6057 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.2463 (2) ÅCell parameters from 9733 reflections
c = 12.8657 (2) Åθ = 2.6–28.3°
α = 73.901 (1)°µ = 0.25 mm−1
β = 86.059 (1)°T = 173 K
γ = 83.549 (1)°Block, red
V = 769.77 (3) Å30.49 × 0.17 × 0.05 mm
Data collection top
Bruker APEXII CCD
diffractometer		3778 independent reflections
Radiation source: fine-focus sealed tube3506 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ϕ and ω scansθmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −10→8
Tmin = 0.888, Tmax = 0.988k = −10→10
14199 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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0441P)2 + 0.3414P]
where P = (Fo2 + 2Fc2)/3
3778 reflections(Δ/σ)max = 0.002
218 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.42 e Å−3
Crystal data top
C12H18N4O6Sγ = 83.549 (1)°
Mr = 346.36V = 769.77 (3) Å3
Triclinic, P1Z = 2
a = 7.6057 (2) ÅMo Kα radiation
b = 8.2463 (2) ŵ = 0.25 mm−1
c = 12.8657 (2) ÅT = 173 K
α = 73.901 (1)°0.49 × 0.17 × 0.05 mm
β = 86.059 (1)°
Data collection top
Bruker APEXII CCD
diffractometer		3778 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		3506 reflections with I > 2σ(I)
Tmin = 0.888, Tmax = 0.988Rint = 0.021
14199 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.29 e Å−3
3778 reflectionsΔρmin = −0.42 e Å−3
218 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 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*/Ueq
S10.29089 (4)−0.28775 (4)1.01726 (2)0.02217 (9)
O60.21891 (13)0.38350 (13)0.79517 (9)0.0345 (2)
O50.27982 (13)0.32749 (13)0.64100 (8)0.0310 (2)
O40.94829 (12)0.02295 (14)0.76530 (8)0.0328 (2)
O30.91096 (14)−0.24191 (14)0.83339 (10)0.0413 (3)
O20.42149 (13)−0.38814 (12)1.09026 (7)0.0293 (2)
O10.13725 (14)−0.20406 (13)1.05726 (8)0.0337 (2)
N10.22714 (17)−0.41143 (15)0.95364 (10)0.0268 (2)
N30.65122 (14)0.20712 (13)0.66209 (8)0.0207 (2)
N40.29355 (13)0.29708 (13)0.73912 (9)0.0221 (2)
N20.85394 (14)−0.09134 (15)0.80100 (8)0.0252 (2)
C10.40261 (16)−0.13002 (15)0.92262 (9)0.0209 (2)
C60.31660 (16)0.03024 (15)0.87675 (9)0.0201 (2)
H60.20120.06210.90210.024*
C50.40260 (15)0.14133 (14)0.79389 (9)0.0189 (2)
C40.57601 (15)0.10563 (14)0.75238 (9)0.0184 (2)
C100.64961 (16)0.39061 (15)0.64526 (10)0.0210 (2)
H10A0.57570.42470.70350.025*
H10B0.59580.45070.57530.025*
C110.83533 (18)0.44270 (17)0.64495 (12)0.0298 (3)
H11A0.88810.38550.71560.036*
H11B0.91040.40620.58800.036*
C120.8312 (2)0.63353 (19)0.62429 (14)0.0386 (3)
H12A0.79000.68980.55140.058*
H12B0.95060.66330.63040.058*
H12C0.75060.67070.67780.058*
C70.74354 (17)0.13316 (16)0.57981 (10)0.0235 (2)
H7A0.73540.00920.60130.028*
H7B0.87040.15240.57510.028*
C80.66410 (19)0.21110 (18)0.46926 (10)0.0298 (3)
H8A0.53350.21320.47720.036*
H8B0.69390.32960.44120.036*
C90.7322 (2)0.1124 (2)0.38841 (12)0.0384 (3)
H9A0.86180.10570.38280.058*
H9B0.68430.17030.31740.058*
H9C0.6943−0.00230.41300.058*
C30.66129 (15)−0.05195 (15)0.81163 (9)0.0207 (2)
C20.57619 (16)−0.16972 (16)0.89134 (10)0.0227 (2)
H20.6365−0.27710.92440.027*
H2N0.312 (3)−0.469 (2)0.9280 (15)0.040 (5)*
H1N0.145 (3)−0.371 (3)0.9149 (16)0.044 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02480 (16)0.02270 (15)0.01851 (14)−0.00303 (11)0.00036 (11)−0.00479 (11)
O60.0289 (5)0.0317 (5)0.0472 (6)0.0089 (4)−0.0057 (4)−0.0212 (5)
O50.0278 (5)0.0336 (5)0.0268 (5)0.0022 (4)−0.0057 (4)−0.0013 (4)
O40.0195 (4)0.0433 (6)0.0375 (5)−0.0035 (4)0.0010 (4)−0.0147 (4)
O30.0284 (5)0.0378 (6)0.0472 (6)0.0141 (4)−0.0041 (5)−0.0002 (5)
O20.0337 (5)0.0318 (5)0.0202 (4)−0.0041 (4)−0.0062 (4)−0.0021 (4)
O10.0338 (5)0.0322 (5)0.0332 (5)−0.0025 (4)0.0117 (4)−0.0093 (4)
N10.0269 (6)0.0247 (5)0.0297 (6)−0.0011 (5)−0.0079 (5)−0.0078 (4)
N30.0221 (5)0.0188 (5)0.0212 (5)−0.0008 (4)0.0033 (4)−0.0067 (4)
N40.0164 (5)0.0198 (5)0.0300 (5)−0.0005 (4)−0.0028 (4)−0.0065 (4)
N20.0197 (5)0.0344 (6)0.0208 (5)0.0053 (4)−0.0031 (4)−0.0087 (4)
C10.0230 (6)0.0219 (5)0.0182 (5)−0.0033 (4)−0.0005 (4)−0.0058 (4)
C60.0186 (5)0.0225 (5)0.0213 (5)−0.0017 (4)−0.0008 (4)−0.0095 (4)
C50.0177 (5)0.0185 (5)0.0213 (5)0.0006 (4)−0.0036 (4)−0.0068 (4)
C40.0181 (5)0.0195 (5)0.0190 (5)−0.0011 (4)−0.0022 (4)−0.0075 (4)
C100.0220 (6)0.0183 (5)0.0232 (5)−0.0013 (4)−0.0008 (4)−0.0069 (4)
C110.0233 (6)0.0284 (6)0.0372 (7)−0.0062 (5)−0.0001 (5)−0.0069 (5)
C120.0386 (8)0.0320 (7)0.0487 (9)−0.0143 (6)−0.0012 (7)−0.0127 (6)
C70.0244 (6)0.0233 (6)0.0229 (6)0.0007 (5)0.0038 (4)−0.0090 (5)
C80.0343 (7)0.0312 (7)0.0231 (6)0.0029 (6)0.0011 (5)−0.0088 (5)
C90.0531 (9)0.0376 (8)0.0278 (7)−0.0050 (7)0.0051 (6)−0.0155 (6)
C30.0169 (5)0.0247 (6)0.0204 (5)0.0023 (4)−0.0015 (4)−0.0077 (4)
C20.0238 (6)0.0221 (5)0.0207 (5)0.0023 (5)−0.0034 (4)−0.0046 (4)
Geometric parameters (Å, º) top
S1—O11.4282 (10)C10—C111.5213 (17)
S1—O21.4375 (10)C10—H10A0.9900
S1—N11.6043 (12)C10—H10B0.9900
S1—C11.7675 (12)C11—C121.519 (2)
O6—N41.2199 (14)C11—H11A0.9900
O5—N41.2264 (14)C11—H11B0.9900
O4—N21.2168 (16)C12—H12A0.9800
O3—N21.2330 (15)C12—H12B0.9800
N1—H2N0.86 (2)C12—H12C0.9800
N1—H1N0.81 (2)C7—C81.5248 (18)
N3—C41.3617 (15)C7—H7A0.9900
N3—C71.4648 (14)C7—H7B0.9900
N3—C101.4666 (15)C8—C91.5208 (19)
N4—C51.4741 (15)C8—H8A0.9900
N2—C31.4701 (15)C8—H8B0.9900
C1—C21.3838 (17)C9—H9A0.9800
C1—C61.3961 (17)C9—H9B0.9800
C6—C51.3786 (17)C9—H9C0.9800
C6—H60.9500C3—C21.3826 (17)
C5—C41.4193 (16)C2—H20.9500
C4—C31.4211 (16)
O1—S1—O2120.49 (6)C12—C11—C10110.85 (11)
O1—S1—N1108.20 (7)C12—C11—H11A109.5
O2—S1—N1106.10 (6)C10—C11—H11A109.5
O1—S1—C1107.20 (6)C12—C11—H11B109.5
O2—S1—C1106.46 (6)C10—C11—H11B109.5
N1—S1—C1107.83 (6)H11A—C11—H11B108.1
S1—N1—H2N114.6 (13)C11—C12—H12A109.5
S1—N1—H1N114.7 (14)C11—C12—H12B109.5
H2N—N1—H1N116.7 (19)H12A—C12—H12B109.5
C4—N3—C7120.12 (10)C11—C12—H12C109.5
C4—N3—C10122.12 (10)H12A—C12—H12C109.5
C7—N3—C10117.72 (10)H12B—C12—H12C109.5
O6—N4—O5124.71 (11)N3—C7—C8111.23 (10)
O6—N4—C5117.62 (10)N3—C7—H7A109.4
O5—N4—C5117.63 (10)C8—C7—H7A109.4
O4—N2—O3123.62 (11)N3—C7—H7B109.4
O4—N2—C3119.83 (11)C8—C7—H7B109.4
O3—N2—C3116.50 (11)H7A—C7—H7B108.0
C2—C1—C6120.07 (11)C9—C8—C7111.89 (12)
C2—C1—S1118.82 (9)C9—C8—H8A109.2
C6—C1—S1121.07 (9)C7—C8—H8A109.2
C5—C6—C1118.64 (11)C9—C8—H8B109.2
C5—C6—H6120.7C7—C8—H8B109.2
C1—C6—H6120.7H8A—C8—H8B107.9
C6—C5—C4124.46 (11)C8—C9—H9A109.5
C6—C5—N4115.18 (10)C8—C9—H9B109.5
C4—C5—N4119.93 (10)H9A—C9—H9B109.5
N3—C4—C5123.91 (10)C8—C9—H9C109.5
N3—C4—C3122.89 (10)H9A—C9—H9C109.5
C5—C4—C3113.13 (10)H9B—C9—H9C109.5
N3—C10—C11111.69 (10)C2—C3—C4123.50 (11)
N3—C10—H10A109.3C2—C3—N2114.89 (10)
C11—C10—H10A109.3C4—C3—N2121.19 (11)
N3—C10—H10B109.3C3—C2—C1119.54 (11)
C11—C10—H10B109.3C3—C2—H2120.2
H10A—C10—H10B107.9C1—C2—H2120.2
O1—S1—C1—C2164.43 (10)C6—C5—C4—C3−5.59 (16)
O2—S1—C1—C234.23 (11)N4—C5—C4—C3−177.72 (10)
N1—S1—C1—C2−79.27 (11)C4—N3—C10—C11114.40 (13)
O1—S1—C1—C6−17.88 (12)C7—N3—C10—C11−63.22 (14)
O2—S1—C1—C6−148.07 (10)N3—C10—C11—C12178.41 (11)
N1—S1—C1—C698.42 (11)C4—N3—C7—C8122.80 (12)
C2—C1—C6—C55.48 (17)C10—N3—C7—C8−59.53 (14)
S1—C1—C6—C5−172.19 (9)N3—C7—C8—C9−168.42 (12)
C1—C6—C5—C4−1.23 (17)N3—C4—C3—C2−168.24 (11)
C1—C6—C5—N4171.23 (10)C5—C4—C3—C28.86 (17)
O6—N4—C5—C654.74 (15)N3—C4—C3—N219.50 (17)
O5—N4—C5—C6−122.95 (12)C5—C4—C3—N2−163.40 (10)
O6—N4—C5—C4−132.43 (12)O4—N2—C3—C2−153.30 (11)
O5—N4—C5—C449.88 (15)O3—N2—C3—C224.18 (16)
C7—N3—C4—C5−133.66 (12)O4—N2—C3—C419.59 (17)
C10—N3—C4—C548.78 (16)O3—N2—C3—C4−162.93 (12)
C7—N3—C4—C343.12 (16)C4—C3—C2—C1−5.24 (18)
C10—N3—C4—C3−134.44 (12)N2—C3—C2—C1167.46 (11)
C6—C5—C4—N3171.47 (11)C6—C1—C2—C3−2.40 (18)
N4—C5—C4—N3−0.66 (17)S1—C1—C2—C3175.32 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H2N···O6i0.86 (2)2.529 (19)2.9956 (15)114.9 (15)
N1—H2N···O2ii0.86 (2)2.26 (2)3.0839 (16)160.5 (17)
N1—H1N···O3iii0.81 (2)2.15 (2)2.9474 (16)170.0 (19)
C2—H2···N1ii0.952.743.6843 (17)171
C9—H9A···O4iv0.982.693.3192 (18)122
C10—H10A···O2v0.992.593.4033 (15)140
C12—H12C···O3vi0.982.713.249 (2)115
C12—H12A···O5vii0.982.613.492 (2)150
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y−1, −z+2; (iii) x−1, y, z; (iv) −x+2, −y, −z+1; (v) −x+1, −y, −z+2; (vi) x, y+1, z; (vii) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H2N···O6i0.86 (2)2.529 (19)2.9956 (15)114.9 (15)
N1—H2N···O2ii0.86 (2)2.26 (2)3.0839 (16)160.5 (17)
N1—H1N···O3iii0.81 (2)2.15 (2)2.9474 (16)170.0 (19)
C2—H2···N1ii0.952.743.6843 (17)171.0
C9—H9A···O4iv0.982.693.3192 (18)122.3
C10—H10A···O2v0.992.593.4033 (15)139.7
C12—H12C···O3vi0.982.713.249 (2)115.0
C12—H12A···O5vii0.982.613.492 (2)149.5
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y−1, −z+2; (iii) x−1, y, z; (iv) −x+2, −y, −z+1; (v) −x+1, −y, −z+2; (vi) x, y+1, z; (vii) −x+1, −y+1, −z+1.
 

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2012R1A1B3003337).

References

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 First citationO'Connell, A. M. & Maslen, E. N. (1967). Acta Cryst. 22, 134–145.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
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 First citationTremayne, M., Seaton, C. C. & Glidewell, C. (2002). Acta Cryst. B58, 823–834.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 71| Part 6| June 2015| Page o429
doi:10.1107/S205698901500955X
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