(E)-N-(2,3,4-Trimeth­oxy-6-methyl­benzyl­idene)naphthalen-1-amine

Wang, C.-Y.

doi:10.1107/S160053680803910X

organic compounds

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Volume 65| Part 1| January 2009| Page o56

doi:10.1107/S160053680803910X

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(E)-N-(2,3,4-Trimethoxy-6-methylbenzylidene)naphthalen-1-amine

Cheng-Yun Wang ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: zhanghuiwfu@163.com

(Received 18 November 2008; accepted 21 November 2008; online 10 December 2008)

In the title compound, C₂₁H₂₁NO₃, the dihedral angle between the naphthalene ring system and the substituted benzene ring is 55.7 (2)°. The molecules are linked into a zigzag chain running along the b axis by C—H⋯O hydrogen bonds.

Related literature

For a related structure, see: Zhang (2008 ).

Experimental

Crystal data

C₂₁H₂₁NO₃
M_r = 335.39
Orthorhombic, P b c a
a = 10.9225 (14) Å
b = 14.7630 (16) Å
c = 22.514 (2) Å
V = 3630.3 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.23 × 0.19 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.981, T_max = 0.994
17242 measured reflections
3195 independent reflections
1918 reflections with I > 2σ(I)
R_int = 0.071

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.166
S = 1.07
3195 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O3ⁱ	0.93	2.56	3.489 (4)	178
Symmetry code: (i) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803910X/ci2730sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803910X/ci2730Isup2.hkl

checkCIF report

Comment top

The preparation, properties and applications of Schiff bases are important in the development of coordination chemistry. In this paper, the crystal structure of the title compound is reported.

Bond lengths and angles of the title molecule (Fig.1) agree with those observed in a related compound, (E)-N-(2,3,4-trimethoxy-6-methylbenzylidene)aniline (Zhang, 2008). The dihedral angle between the naphthalene ring system and the substituted benzene ring is 55.7 (2)°. One of the methoxy groups is coplanar (C10—O3—C5—C6 = 2.4 (4)°) with the attached ring whereas the other two methoxy groups are twisted (C8—O1—C3—C4 = -78.3 (4)° and C9—O2—C4—C3 = 109.1 (3)°).

The molecules are linked into a zigzag chain running along the b axis by C—H···O hydrogen bonds (Table 1).

Related literature top

For a related structure, see: Zhang (2008).

Experimental top

A mixture of 1-naphthylamine (0.715 g, 5 mmol) and 2,3,4-trimethoxy-6-methylbenzaldehyde (1.04 g, 5 mmol) in ethanol (30 ml) was refluxed for 2 h. After cooling, the precipitate obtained was filtered and dried. The crude product was (20 mg) was dissolved in ethanol (20 ml) and the solution was filtered to remove impurities, and then left for crystallization at room temperature. Single crystals suitable for X-ray crystal structure determination were obtained after a week.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.

(E)-N-(2,3,4-Trimethoxy-6-methylbenzylidene)naphthalen-1-amine top

Crystal data top

C₂₁H₂₁NO₃	F(000) = 1424
M_r = 335.39	D_x = 1.227 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3424 reflections
a = 10.9225 (14) Å	θ = 2.5–25.3°
b = 14.7630 (16) Å	µ = 0.08 mm⁻¹
c = 22.514 (2) Å	T = 298 K
V = 3630.3 (7) Å³	Plate, light yellow
Z = 8	0.23 × 0.19 × 0.08 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3195 independent reflections
Radiation source: fine-focus sealed tube	1918 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −12→8
T_min = 0.981, T_max = 0.994	k = −17→15
17242 measured reflections	l = −26→25

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.166	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0824P)²] where P = (F_o² + 2F_c²)/3
3195 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₁H₂₁NO₃	V = 3630.3 (7) Å³
M_r = 335.39	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.9225 (14) Å	µ = 0.08 mm⁻¹
b = 14.7630 (16) Å	T = 298 K
c = 22.514 (2) Å	0.23 × 0.19 × 0.08 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3195 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	1918 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.994	R_int = 0.071
17242 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.166	H-atom parameters constrained
S = 1.07	Δρ_max = 0.19 e Å⁻³
3195 reflections	Δρ_min = −0.25 e Å⁻³
226 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

	x	y	z	U_iso*/U_eq
N1	0.1079 (2)	0.32182 (15)	0.65758 (10)	0.0437 (6)
O1	−0.20286 (18)	0.26652 (12)	0.57093 (9)	0.0494 (6)
O2	−0.34730 (17)	0.11513 (12)	0.58640 (8)	0.0463 (5)
O3	−0.29401 (19)	−0.00497 (13)	0.67264 (8)	0.0521 (6)
C1	0.0044 (3)	0.30050 (17)	0.63498 (12)	0.0404 (7)
H1	−0.0271	0.3393	0.6063	0.048*
C2	−0.0689 (2)	0.22122 (17)	0.64990 (12)	0.0374 (7)
C3	−0.1715 (3)	0.20404 (17)	0.61366 (11)	0.0360 (7)
C4	−0.2445 (2)	0.12749 (19)	0.62117 (11)	0.0354 (7)
C5	−0.2172 (3)	0.06808 (17)	0.66764 (12)	0.0382 (7)
C6	−0.1196 (3)	0.08606 (19)	0.70516 (12)	0.0429 (8)
H6	−0.1040	0.0467	0.7365	0.051*
C7	−0.0440 (3)	0.16116 (18)	0.69743 (12)	0.0397 (7)
C8	−0.1737 (5)	0.2453 (3)	0.51222 (15)	0.1067 (17)
H8A	−0.1021	0.2076	0.5114	0.160*
H8B	−0.1579	0.3001	0.4905	0.160*
H8C	−0.2409	0.2136	0.4943	0.160*
C9	−0.3371 (3)	0.0441 (2)	0.54325 (14)	0.0654 (10)
H9A	−0.2605	0.0495	0.5227	0.098*
H9B	−0.4032	0.0487	0.5153	0.098*
H9C	−0.3408	−0.0136	0.5629	0.098*
C10	−0.2751 (4)	−0.0653 (2)	0.72126 (16)	0.0843 (13)
H10A	−0.1990	−0.0969	0.7160	0.126*
H10B	−0.3410	−0.1083	0.7229	0.126*
H10C	−0.2725	−0.0315	0.7576	0.126*
C11	0.0612 (3)	0.1741 (2)	0.73974 (14)	0.0616 (10)
H11A	0.1370	0.1649	0.7190	0.092*
H11B	0.0548	0.1313	0.7717	0.092*
H11C	0.0590	0.2345	0.7555	0.092*
C12	0.1640 (3)	0.40259 (17)	0.63702 (12)	0.0367 (7)
C13	0.1017 (3)	0.48289 (18)	0.63178 (13)	0.0450 (8)
H13	0.0191	0.4855	0.6415	0.054*
C14	0.1619 (3)	0.56103 (19)	0.61192 (15)	0.0539 (9)
H14	0.1181	0.6148	0.6086	0.065*
C15	0.2820 (3)	0.56022 (19)	0.59751 (14)	0.0530 (8)
H15	0.3198	0.6130	0.5843	0.064*
C16	0.3507 (3)	0.47867 (18)	0.60249 (13)	0.0423 (7)
C17	0.2925 (3)	0.39934 (17)	0.62421 (11)	0.0375 (7)
C18	0.3634 (3)	0.32002 (19)	0.63141 (13)	0.0463 (8)
H18	0.3272	0.2681	0.6469	0.056*
C19	0.4841 (3)	0.3187 (2)	0.61596 (15)	0.0582 (9)
H19	0.5294	0.2659	0.6209	0.070*
C20	0.5401 (3)	0.3956 (2)	0.59289 (15)	0.0613 (9)
H20	0.6220	0.3934	0.5818	0.074*
C21	0.4760 (3)	0.4741 (2)	0.58642 (14)	0.0562 (9)
H21	0.5148	0.5252	0.5713	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0416 (16)	0.0425 (14)	0.0471 (15)	−0.0020 (12)	−0.0009 (13)	0.0028 (11)
O1	0.0476 (13)	0.0498 (12)	0.0507 (13)	0.0062 (10)	−0.0107 (10)	0.0102 (10)
O2	0.0382 (12)	0.0539 (12)	0.0468 (12)	0.0001 (9)	−0.0099 (10)	−0.0034 (10)
O3	0.0574 (15)	0.0524 (12)	0.0465 (12)	−0.0163 (11)	−0.0104 (10)	0.0093 (10)
C1	0.0432 (19)	0.0409 (16)	0.0370 (16)	0.0035 (14)	−0.0001 (15)	−0.0002 (12)
C2	0.0364 (17)	0.0391 (15)	0.0367 (16)	0.0038 (13)	−0.0001 (14)	−0.0028 (13)
C3	0.0373 (17)	0.0377 (15)	0.0332 (15)	0.0073 (13)	0.0001 (14)	0.0003 (12)
C4	0.0285 (15)	0.0461 (16)	0.0315 (15)	0.0027 (13)	−0.0040 (13)	−0.0034 (12)
C5	0.0368 (18)	0.0422 (16)	0.0357 (16)	−0.0041 (13)	−0.0011 (14)	0.0002 (13)
C6	0.0488 (19)	0.0471 (17)	0.0328 (16)	−0.0029 (15)	−0.0055 (15)	0.0091 (13)
C7	0.0406 (18)	0.0445 (16)	0.0341 (15)	−0.0010 (14)	−0.0075 (14)	0.0040 (13)
C8	0.198 (5)	0.085 (3)	0.038 (2)	0.004 (3)	0.004 (3)	0.012 (2)
C9	0.062 (2)	0.087 (2)	0.0472 (19)	−0.015 (2)	−0.0120 (18)	−0.0113 (18)
C10	0.102 (3)	0.079 (3)	0.072 (2)	−0.041 (2)	−0.030 (2)	0.036 (2)
C11	0.057 (2)	0.071 (2)	0.057 (2)	−0.0187 (17)	−0.0196 (18)	0.0195 (17)
C12	0.0378 (17)	0.0367 (15)	0.0357 (16)	0.0000 (13)	−0.0035 (14)	−0.0031 (12)
C13	0.0394 (18)	0.0420 (17)	0.0534 (19)	0.0042 (14)	−0.0036 (15)	−0.0067 (13)
C14	0.051 (2)	0.0357 (17)	0.075 (2)	0.0031 (15)	−0.0084 (19)	−0.0022 (15)
C15	0.053 (2)	0.0359 (17)	0.070 (2)	−0.0102 (15)	−0.0104 (18)	0.0042 (15)
C16	0.0410 (18)	0.0396 (16)	0.0462 (17)	−0.0063 (14)	−0.0066 (15)	−0.0045 (13)
C17	0.0373 (17)	0.0382 (16)	0.0369 (16)	−0.0005 (14)	−0.0074 (14)	−0.0061 (12)
C18	0.045 (2)	0.0382 (16)	0.0555 (19)	0.0033 (14)	−0.0038 (16)	−0.0039 (14)
C19	0.044 (2)	0.054 (2)	0.077 (2)	0.0105 (16)	−0.0064 (19)	−0.0060 (17)
C20	0.0356 (19)	0.063 (2)	0.085 (3)	−0.0022 (17)	0.0030 (19)	−0.0095 (19)
C21	0.0411 (19)	0.0558 (19)	0.072 (2)	−0.0134 (16)	−0.0018 (18)	0.0003 (16)

Geometric parameters (Å, º) top

N1—C1	1.279 (4)	C10—H10A	0.96
N1—C12	1.418 (3)	C10—H10B	0.96
O1—C3	1.376 (3)	C10—H10C	0.96
O1—C8	1.395 (4)	C11—H11A	0.96
O2—C4	1.381 (3)	C11—H11B	0.96
O2—C9	1.434 (3)	C11—H11C	0.96
O3—C5	1.371 (3)	C12—C13	1.372 (4)
O3—C10	1.426 (3)	C12—C17	1.434 (4)
C1—C2	1.457 (4)	C13—C14	1.401 (4)
C1—H1	0.93	C13—H13	0.93
C2—C3	1.410 (4)	C14—C15	1.351 (4)
C2—C7	1.416 (4)	C14—H14	0.93
C3—C4	1.393 (4)	C15—C16	1.423 (4)
C4—C5	1.397 (4)	C15—H15	0.93
C5—C6	1.386 (4)	C16—C21	1.417 (4)
C6—C7	1.393 (4)	C16—C17	1.419 (4)
C6—H6	0.93	C17—C18	1.413 (4)
C7—C11	1.505 (4)	C18—C19	1.364 (4)
C8—H8A	0.96	C18—H18	0.93
C8—H8B	0.96	C19—C20	1.390 (4)
C8—H8C	0.96	C19—H19	0.93
C9—H9A	0.96	C20—C21	1.362 (4)
C9—H9B	0.96	C20—H20	0.93
C9—H9C	0.96	C21—H21	0.93

C1—N1—C12	117.3 (2)	O3—C10—H10C	109.5
C3—O1—C8	117.1 (2)	H10A—C10—H10C	109.5
C4—O2—C9	114.7 (2)	H10B—C10—H10C	109.5
C5—O3—C10	117.8 (2)	C7—C11—H11A	109.5
N1—C1—C2	126.3 (3)	C7—C11—H11B	109.5
N1—C1—H1	116.9	H11A—C11—H11B	109.5
C2—C1—H1	116.9	C7—C11—H11C	109.5
C3—C2—C7	118.5 (2)	H11A—C11—H11C	109.5
C3—C2—C1	116.6 (2)	H11B—C11—H11C	109.5
C7—C2—C1	124.9 (3)	C13—C12—N1	122.7 (3)
O1—C3—C4	119.1 (2)	C13—C12—C17	119.8 (3)
O1—C3—C2	118.8 (2)	N1—C12—C17	117.4 (2)
C4—C3—C2	122.0 (2)	C12—C13—C14	120.4 (3)
O2—C4—C3	120.2 (2)	C12—C13—H13	119.8
O2—C4—C5	121.0 (2)	C14—C13—H13	119.8
C3—C4—C5	118.6 (2)	C15—C14—C13	121.6 (3)
O3—C5—C6	124.8 (2)	C15—C14—H14	119.2
O3—C5—C4	115.2 (2)	C13—C14—H14	119.2
C6—C5—C4	120.0 (3)	C14—C15—C16	120.0 (3)
C5—C6—C7	122.2 (2)	C14—C15—H15	120.0
C5—C6—H6	118.9	C16—C15—H15	120.0
C7—C6—H6	118.9	C21—C16—C17	118.7 (3)
C6—C7—C2	118.6 (3)	C21—C16—C15	121.9 (3)
C6—C7—C11	118.3 (2)	C17—C16—C15	119.3 (3)
C2—C7—C11	123.0 (3)	C18—C17—C16	118.6 (3)
O1—C8—H8A	109.5	C18—C17—C12	122.8 (3)
O1—C8—H8B	109.5	C16—C17—C12	118.7 (2)
H8A—C8—H8B	109.5	C19—C18—C17	120.8 (3)
O1—C8—H8C	109.5	C19—C18—H18	119.6
H8A—C8—H8C	109.5	C17—C18—H18	119.6
H8B—C8—H8C	109.5	C18—C19—C20	120.6 (3)
O2—C9—H9A	109.5	C18—C19—H19	119.7
O2—C9—H9B	109.5	C20—C19—H19	119.7
H9A—C9—H9B	109.5	C21—C20—C19	120.6 (3)
O2—C9—H9C	109.5	C21—C20—H20	119.7
H9A—C9—H9C	109.5	C19—C20—H20	119.7
H9B—C9—H9C	109.5	C20—C21—C16	120.6 (3)
O3—C10—H10A	109.5	C20—C21—H21	119.7
O3—C10—H10B	109.5	C16—C21—H21	119.7
H10A—C10—H10B	109.5

C12—N1—C1—C2	−179.6 (2)	C1—C2—C7—C6	−177.7 (3)
N1—C1—C2—C3	−171.3 (3)	C3—C2—C7—C11	−178.5 (3)
N1—C1—C2—C7	8.5 (4)	C1—C2—C7—C11	1.7 (4)
C8—O1—C3—C4	−78.3 (4)	C1—N1—C12—C13	47.2 (4)
C8—O1—C3—C2	103.9 (3)	C1—N1—C12—C17	−135.8 (3)
C7—C2—C3—O1	174.0 (2)	N1—C12—C13—C14	179.2 (3)
C1—C2—C3—O1	−6.2 (4)	C17—C12—C13—C14	2.3 (4)
C7—C2—C3—C4	−3.7 (4)	C12—C13—C14—C15	−0.2 (5)
C1—C2—C3—C4	176.1 (2)	C13—C14—C15—C16	−0.2 (5)
C9—O2—C4—C3	109.1 (3)	C14—C15—C16—C21	178.3 (3)
C9—O2—C4—C5	−76.4 (3)	C14—C15—C16—C17	−1.7 (4)
O1—C3—C4—O2	−0.5 (4)	C21—C16—C17—C18	2.8 (4)
C2—C3—C4—O2	177.2 (2)	C15—C16—C17—C18	−177.2 (3)
O1—C3—C4—C5	−175.2 (2)	C21—C16—C17—C12	−176.2 (3)
C2—C3—C4—C5	2.5 (4)	C15—C16—C17—C12	3.8 (4)
C10—O3—C5—C6	2.4 (4)	C13—C12—C17—C18	176.9 (3)
C10—O3—C5—C4	−176.5 (3)	N1—C12—C17—C18	−0.1 (4)
O2—C4—C5—O3	4.6 (4)	C13—C12—C17—C16	−4.1 (4)
C3—C4—C5—O3	179.2 (2)	N1—C12—C17—C16	178.8 (2)
O2—C4—C5—C6	−174.4 (2)	C16—C17—C18—C19	−2.2 (4)
C3—C4—C5—C6	0.2 (4)	C12—C17—C18—C19	176.8 (3)
O3—C5—C6—C7	179.4 (3)	C17—C18—C19—C20	0.1 (5)
C4—C5—C6—C7	−1.7 (4)	C18—C19—C20—C21	1.3 (5)
C5—C6—C7—C2	0.6 (4)	C19—C20—C21—C16	−0.7 (5)
C5—C6—C7—C11	−178.9 (3)	C17—C16—C21—C20	−1.4 (5)
C3—C2—C7—C6	2.1 (4)	C15—C16—C21—C20	178.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3ⁱ	0.93	2.56	3.489 (4)	178

Symmetry code: (i) −x−1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁NO₃
M_r	335.39
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	10.9225 (14), 14.7630 (16), 22.514 (2)
V (Å³)	3630.3 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.23 × 0.19 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.981, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	17242, 3195, 1918
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.166, 1.07
No. of reflections	3195
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.25

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3ⁱ	0.93	2.56	3.489 (4)	178

Symmetry code: (i) −x−1/2, y+1/2, z.

References

Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, H. (2008). Acta Cryst. E64, o1219. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 1| January 2009| Page o56

doi:10.1107/S160053680803910X

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