2-(4-Chloro-1H-indol-3-yl)acetonitrile

Pan, M.-L.; Li, X.; Luo, Y.-H.

doi:10.1107/S1600536811054079

organic compounds

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Volume 68| Part 1| January 2012| Page o203

doi:10.1107/S1600536811054079

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2-(4-Chloro-1H-indol-3-yl)acetonitrile

Mei-Ling Pan,^a ^* Xiang Li ^a and Yang-Hui Luo ^a

^aCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: nantongpml@163.com

(Received 4 December 2011; accepted 15 December 2011; online 21 December 2011)

The title compound, C₁₀H₇ClN₂, contains two approximately planar molecules, A and B (r.m.s. deviations = 0.039 and 0.064 Å, respectively) in the asymmetric unit. In the crystal, N—H⋯N hydrogen bonds link the molecules into C(7) chains of alternating A and B molecules propagating along the a-axis direction. The crystal used for the data collection was found to be a racemic twin.

Related literature

For a related structure, see: Ge et al. (2012 ).

Experimental

Crystal data

C₁₀H₇ClN₂
M_r = 190.63
Orthorhombic, P c a 2₁
a = 7.5091 (15) Å
b = 11.041 (2) Å
c = 21.380 (4) Å
V = 1772.6 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 293 K
0.33 × 0.25 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.893, T_max = 0.927
17075 measured reflections
4057 independent reflections
2753 reflections with I > 2σ(I)
R_int = 0.058
2 standard reflections every 150 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.111
S = 1.03
4057 reflections
236 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 1968 Friedel pairs
Flack parameter: 0.66 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N4	0.86	2.42	3.089 (6)	135
N2—H2A⋯N3ⁱ	0.86	2.21	3.058 (6)	170
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+2, z]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811054079/hb6554sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811054079/hb6554Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811054079/hb6554Isup3.cml

checkCIF report

Related literature top

For a related structure, see: Ge et al. (2012).

Experimental top

The title compound 3-(cyanomethyl)indole-4-chlorine was purchased commercially from ChemFuture PharmaTech, Ltd (Nanjing, Jiangsu). and were used as received without further purification. Colourles prisms were obstained by slow evaporation of a methanol solution.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing 30% displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound, showing the structure from the a axis. Hydrogen bonds are shown as dashed lines.

2-(4-Chloro-1H-indol-3-yl)acetonitrile top

Crystal data top

C₁₀H₇ClN₂	F(000) = 784
M_r = 190.63	D_x = 1.429 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4057 reflections
a = 7.5091 (15) Å	θ = 2.5–27.5°
b = 11.041 (2) Å	µ = 0.38 mm⁻¹
c = 21.380 (4) Å	T = 293 K
V = 1772.6 (6) Å³	Prism, colourless
Z = 8	0.33 × 0.25 × 0.20 mm

Data collection top

Rigaku SCXmini diffractometer	2753 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.058
Graphite monochromator	θ_max = 27.5°, θ_min = 3.3°
CCD_Profile_fitting scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −14→14
T_min = 0.893, T_max = 0.927	l = −27→27
17075 measured reflections	2 standard reflections every 150 reflections
4057 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.048	w = 1/[σ²(F_o²) + (0.0469P)² + 0.1573P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.111	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.27 e Å⁻³
4057 reflections	Δρ_min = −0.22 e Å⁻³
236 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008)
1 restraint	Extinction coefficient: 0
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1968 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.66 (10)

Crystal data top

C₁₀H₇ClN₂	V = 1772.6 (6) Å³
M_r = 190.63	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 7.5091 (15) Å	µ = 0.38 mm⁻¹
b = 11.041 (2) Å	T = 293 K
c = 21.380 (4) Å	0.33 × 0.25 × 0.20 mm

Data collection top

Rigaku SCXmini diffractometer	2753 reflections with I > 2σ(I)
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	R_int = 0.058
T_min = 0.893, T_max = 0.927	2 standard reflections every 150 reflections
17075 measured reflections	intensity decay: none
4057 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.111	Δρ_max = 0.27 e Å⁻³
S = 1.03	Δρ_min = −0.22 e Å⁻³
4057 reflections	Absolute structure: Flack (1983), 1968 Friedel pairs
236 parameters	Absolute structure parameter: 0.66 (10)
1 restraint

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

	x	y	z	U_iso*/U_eq
Cl1	0.57185 (18)	0.47362 (9)	−0.10226 (5)	0.0585 (3)
N1	0.3359 (6)	0.4908 (3)	0.1147 (2)	0.0451 (11)
H1A	0.3006	0.4743	0.1520	0.054*
N3	0.4392 (5)	0.9029 (3)	0.05314 (18)	0.0781 (11)
C1	0.3547 (5)	0.6055 (3)	0.0894 (2)	0.0470 (11)
H1B	0.3234	0.6773	0.1093	0.056*
C2	0.4252 (4)	0.5977 (3)	0.0317 (2)	0.0372 (8)
C3	0.4428 (6)	0.4720 (4)	0.0164 (2)	0.0356 (8)
C4	0.4979 (4)	0.4026 (3)	−0.03431 (17)	0.0399 (7)
C5	0.4984 (6)	0.2769 (3)	−0.0313 (2)	0.0528 (12)
H5A	0.5375	0.2322	−0.0656	0.063*
C6	0.4413 (6)	0.2172 (4)	0.0222 (3)	0.0571 (13)
H6A	0.4426	0.1330	0.0233	0.069*
C7	0.3829 (4)	0.2803 (3)	0.07360 (19)	0.0521 (9)
H7A	0.3450	0.2411	0.1097	0.062*
C8	0.3834 (5)	0.4034 (3)	0.0688 (2)	0.0412 (10)
C9	0.4689 (6)	0.7050 (3)	−0.00949 (18)	0.0454 (10)
H9A	0.5898	0.6971	−0.0249	0.055*
H9B	0.3894	0.7056	−0.0452	0.055*
C10	0.4518 (6)	0.8176 (3)	0.0240 (2)	0.0491 (10)
Cl2	0.31981 (19)	1.02214 (9)	0.39526 (5)	0.0628 (4)
N2	0.0887 (6)	1.0076 (3)	0.1779 (2)	0.0540 (13)
H2A	0.0441	1.0232	0.1417	0.065*
N4	0.1867 (6)	0.5920 (3)	0.23876 (19)	0.0798 (11)
C11	0.1204 (5)	0.8969 (4)	0.20034 (19)	0.0454 (10)
H11A	0.1048	0.8260	0.1775	0.054*
C12	0.1782 (4)	0.9000 (3)	0.26055 (19)	0.0401 (8)
C13	0.1928 (6)	1.0261 (4)	0.2749 (2)	0.0385 (9)
C14	0.2470 (4)	1.0945 (3)	0.32694 (17)	0.0442 (8)
C15	0.2436 (6)	1.2171 (3)	0.3253 (2)	0.0531 (11)
H15A	0.2807	1.2608	0.3601	0.064*
C16	0.1853 (6)	1.2786 (4)	0.2721 (3)	0.0618 (14)
H16A	0.1840	1.3628	0.2720	0.074*
C17	0.1308 (4)	1.2175 (4)	0.2208 (2)	0.0594 (10)
H17A	0.0889	1.2594	0.1861	0.071*
C18	0.1377 (5)	1.0878 (3)	0.2203 (2)	0.0422 (10)
C19	0.2208 (6)	0.7932 (3)	0.30169 (19)	0.0468 (10)
H19A	0.3417	0.8005	0.3172	0.056*
H19B	0.1410	0.7926	0.3374	0.056*
C20	0.2024 (7)	0.6794 (4)	0.2670 (3)	0.0579 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0658 (7)	0.0684 (5)	0.0413 (6)	−0.0070 (6)	0.0135 (6)	−0.0086 (8)
N1	0.050 (3)	0.056 (2)	0.029 (3)	−0.0015 (13)	0.004 (2)	0.0031 (12)
N3	0.124 (3)	0.050 (2)	0.060 (2)	−0.011 (2)	−0.015 (2)	−0.0052 (17)
C1	0.037 (2)	0.043 (2)	0.061 (3)	0.0015 (15)	0.0014 (18)	−0.013 (2)
C2	0.0324 (18)	0.0367 (19)	0.042 (2)	−0.0052 (15)	−0.0034 (17)	−0.0017 (16)
C3	0.030 (2)	0.0480 (19)	0.029 (2)	0.001 (2)	−0.0011 (15)	−0.004 (2)
C4	0.0335 (17)	0.0480 (18)	0.0383 (19)	−0.0033 (16)	0.0004 (14)	−0.0022 (15)
C5	0.050 (2)	0.037 (2)	0.072 (3)	0.0072 (18)	−0.005 (2)	−0.018 (2)
C6	0.050 (2)	0.047 (2)	0.074 (3)	−0.001 (2)	−0.008 (2)	0.005 (2)
C7	0.049 (2)	0.057 (2)	0.051 (2)	−0.0046 (16)	−0.0075 (17)	0.014 (2)
C8	0.042 (2)	0.046 (2)	0.036 (2)	0.0043 (15)	−0.0130 (18)	−0.0005 (16)
C9	0.051 (2)	0.045 (2)	0.040 (2)	−0.0052 (17)	−0.0022 (19)	−0.0067 (16)
C10	0.064 (3)	0.036 (2)	0.047 (2)	−0.0061 (19)	−0.0045 (19)	−0.0002 (19)
Cl2	0.0702 (8)	0.0734 (6)	0.0447 (7)	0.0137 (6)	−0.0164 (6)	−0.0136 (9)
N2	0.056 (3)	0.071 (3)	0.035 (3)	0.0072 (15)	−0.009 (3)	0.0068 (14)
N4	0.122 (3)	0.043 (2)	0.074 (3)	−0.005 (2)	0.009 (2)	−0.0032 (18)
C11	0.050 (2)	0.056 (2)	0.030 (2)	0.0035 (18)	0.0019 (16)	0.0035 (17)
C12	0.0360 (19)	0.054 (2)	0.031 (2)	0.0018 (17)	0.0026 (17)	−0.0042 (17)
C13	0.033 (2)	0.0450 (18)	0.038 (2)	0.003 (2)	0.0077 (16)	0.000 (2)
C14	0.0391 (19)	0.0499 (19)	0.044 (2)	0.0003 (17)	0.0050 (16)	−0.0071 (17)
C15	0.048 (2)	0.053 (2)	0.058 (3)	−0.001 (2)	0.006 (2)	−0.007 (2)
C16	0.066 (3)	0.033 (2)	0.087 (4)	−0.001 (2)	0.022 (3)	0.002 (2)
C17	0.051 (2)	0.061 (2)	0.066 (3)	0.0055 (19)	0.008 (2)	0.023 (2)
C18	0.032 (2)	0.041 (2)	0.053 (3)	0.0096 (15)	0.002 (2)	0.0007 (18)
C19	0.049 (2)	0.045 (2)	0.046 (3)	0.0065 (17)	0.0035 (19)	0.0020 (17)
C20	0.075 (3)	0.052 (2)	0.046 (3)	0.003 (2)	0.009 (2)	0.008 (2)

Geometric parameters (Å, º) top

Cl1—C4	1.742 (4)	Cl2—C14	1.752 (4)
N1—C1	1.385 (5)	N2—C18	1.319 (6)
N1—C8	1.421 (6)	N2—C11	1.335 (5)
N1—H1A	0.8600	N2—H2A	0.8601
N3—C10	1.132 (5)	N4—C20	1.144 (6)
C1—C2	1.346 (5)	C11—C12	1.359 (5)
C1—H1B	0.9300	C11—H11A	0.9300
C2—C3	1.432 (4)	C12—C13	1.430 (5)
C2—C9	1.511 (5)	C12—C19	1.506 (5)
C3—C4	1.391 (5)	C13—C14	1.405 (6)
C3—C8	1.424 (6)	C13—C18	1.413 (6)
C4—C5	1.390 (5)	C14—C15	1.354 (5)
C5—C6	1.388 (7)	C15—C16	1.395 (7)
C5—H5A	0.9300	C15—H15A	0.9300
C6—C7	1.373 (7)	C16—C17	1.351 (7)
C6—H6A	0.9300	C16—H16A	0.9300
C7—C8	1.364 (5)	C17—C18	1.434 (6)
C7—H7A	0.9300	C17—H17A	0.9300
C9—C10	1.441 (5)	C19—C20	1.466 (6)
C9—H9A	0.9700	C19—H19A	0.9700
C9—H9B	0.9700	C19—H19B	0.9700

C1—N1—C8	109.0 (4)	C18—N2—C11	108.5 (5)
C1—N1—H1A	125.9	C18—N2—H2A	126.4
C8—N1—H1A	125.1	C11—N2—H2A	125.2
C2—C1—N1	109.9 (4)	N2—C11—C12	112.0 (4)
C2—C1—H1B	125.1	N2—C11—H11A	124.0
N1—C1—H1B	125.1	C12—C11—H11A	124.0
C1—C2—C3	107.9 (3)	C11—C12—C13	104.6 (4)
C1—C2—C9	124.7 (3)	C11—C12—C19	127.0 (3)
C3—C2—C9	127.4 (4)	C13—C12—C19	128.4 (4)
C4—C3—C8	114.4 (3)	C14—C13—C18	118.7 (4)
C4—C3—C2	137.6 (4)	C14—C13—C12	135.7 (4)
C8—C3—C2	107.9 (4)	C18—C13—C12	105.6 (4)
C3—C4—C5	121.0 (3)	C15—C14—C13	120.7 (4)
C3—C4—Cl1	119.8 (3)	C15—C14—Cl2	118.9 (3)
C5—C4—Cl1	119.2 (3)	C13—C14—Cl2	120.4 (3)
C6—C5—C4	120.7 (4)	C14—C15—C16	120.9 (4)
C6—C5—H5A	119.6	C14—C15—H15A	119.5
C4—C5—H5A	119.6	C16—C15—H15A	119.5
C7—C6—C5	121.2 (4)	C17—C16—C15	120.9 (4)
C7—C6—H6A	119.4	C17—C16—H16A	119.5
C5—C6—H6A	119.4	C15—C16—H16A	119.5
C6—C7—C8	116.4 (4)	C16—C17—C18	119.6 (4)
C6—C7—H7A	121.8	C16—C17—H17A	120.2
C8—C7—H7A	121.8	C18—C17—H17A	120.2
C7—C8—C3	126.2 (4)	N2—C18—C13	109.1 (4)
C7—C8—N1	128.6 (4)	N2—C18—C17	131.7 (4)
C3—C8—N1	105.1 (3)	C13—C18—C17	119.0 (4)
C10—C9—C2	111.5 (3)	C20—C19—C12	110.8 (4)
C10—C9—H9A	109.3	C20—C19—H19A	109.5
C2—C9—H9A	109.3	C12—C19—H19A	109.5
C10—C9—H9B	109.3	C20—C19—H19B	109.5
C2—C9—H9B	109.3	C12—C19—H19B	109.5
H9A—C9—H9B	108.0	H19A—C19—H19B	108.1
N3—C10—C9	176.5 (5)	N4—C20—C19	178.4 (5)

C8—N1—C1—C2	−4.9 (5)	C18—N2—C11—C12	5.0 (6)
N1—C1—C2—C3	3.9 (5)	N2—C11—C12—C13	−3.6 (5)
N1—C1—C2—C9	−178.4 (4)	N2—C11—C12—C19	177.7 (4)
C1—C2—C3—C4	177.3 (5)	C11—C12—C13—C14	−178.4 (5)
C9—C2—C3—C4	−0.2 (8)	C19—C12—C13—C14	0.3 (8)
C1—C2—C3—C8	−1.5 (4)	C11—C12—C13—C18	0.9 (4)
C9—C2—C3—C8	−179.1 (4)	C19—C12—C13—C18	179.6 (4)
C8—C3—C4—C5	−2.0 (5)	C18—C13—C14—C15	1.2 (6)
C2—C3—C4—C5	179.2 (5)	C12—C13—C14—C15	−179.6 (5)
C8—C3—C4—Cl1	179.3 (3)	C18—C13—C14—Cl2	−179.0 (3)
C2—C3—C4—Cl1	0.5 (7)	C12—C13—C14—Cl2	0.3 (7)
C3—C4—C5—C6	1.0 (6)	C13—C14—C15—C16	0.4 (6)
Cl1—C4—C5—C6	179.7 (4)	Cl2—C14—C15—C16	−179.5 (4)
C4—C5—C6—C7	0.0 (7)	C14—C15—C16—C17	0.0 (7)
C5—C6—C7—C8	0.4 (6)	C15—C16—C17—C18	−1.8 (7)
C6—C7—C8—C3	−1.7 (6)	C11—N2—C18—C13	−4.2 (6)
C6—C7—C8—N1	−177.9 (4)	C11—N2—C18—C17	−179.0 (4)
C4—C3—C8—C7	2.5 (6)	C14—C13—C18—N2	−178.5 (4)
C2—C3—C8—C7	−178.3 (4)	C12—C13—C18—N2	2.0 (5)
C4—C3—C8—N1	179.4 (4)	C14—C13—C18—C17	−3.0 (6)
C2—C3—C8—N1	−1.4 (4)	C12—C13—C18—C17	177.5 (3)
C1—N1—C8—C7	−179.4 (4)	C16—C17—C18—N2	177.7 (5)
C1—N1—C8—C3	3.8 (5)	C16—C17—C18—C13	3.4 (6)
C1—C2—C9—C10	8.9 (6)	C11—C12—C19—C20	3.4 (6)
C3—C2—C9—C10	−173.9 (4)	C13—C12—C19—C20	−174.9 (4)
C2—C9—C10—N3	21 (9)	C12—C19—C20—N4	−3 (20)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N4	0.86	2.42	3.089 (6)	135
N2—H2A···N3ⁱ	0.86	2.21	3.058 (6)	170

Symmetry code: (i) x−1/2, −y+2, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₇ClN₂
M_r	190.63
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	7.5091 (15), 11.041 (2), 21.380 (4)
V (Å³)	1772.6 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.33 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.893, 0.927
No. of measured, independent and observed [I > 2σ(I)] reflections	17075, 4057, 2753
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.111, 1.03
No. of reflections	4057
No. of parameters	236
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.22
Absolute structure	Flack (1983), 1968 Friedel pairs
Absolute structure parameter	0.66 (10)

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N4	0.86	2.42	3.089 (6)	135
N2—H2A···N3ⁱ	0.86	2.21	3.058 (6)	170

Symmetry code: (i) x−1/2, −y+2, z.

Acknowledgements

The authors are grateful to the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ge, Y.-H., Pan, M.-L., Xu, J. & Luo, Y.-H. (2012). Acta Cryst. E68, o141. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar