N-(2,4-Dimethyl­phen­yl)-2-methyl­benzamide

Gowda, B.T.; Tokarčík, M.; Kožíšek, J.; Rodrigues, V.Z.; Fuess, H.

doi:10.1107/S1600536809009830

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o826

doi:10.1107/S1600536809009830

Open

access

N-(2,4-Dimethylphenyl)-2-methylbenzamide

B. Thimme Gowda,^a ^* Miroslav Tokarčík,^b Jozef Kožíšek,^b Vinola Zeena Rodrigues ^a and Hartmut Fuess ^c

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bFaculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and ^cInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 4 March 2009; accepted 17 March 2009; online 25 March 2009)

In the title compound, C₁₆H₁₇NO, the N—H bond is in an anti conformation with respect to the C=O bonds. The aniline and benzoyl rings are almost coplanar, making a dihedral angle of 4.9 (3)°. The plane of the amide group makes an angle of 61.3 (3)° with the aniline ring and 58.3 (3)° with the benzoyl ring. In the crystal, the molecules are linked by N—H⋯O hydrogen bonds into chains running along the b axis.

Related literature

For related structures, see Gowda et al. (2003 , 2008a ,b ,c ).

Experimental

Crystal data

C₁₆H₁₇NO
M_r = 239.31
Orthorhombic, P b c a
a = 6.0062 (4) Å
b = 9.8036 (6) Å
c = 44.943 (4) Å
V = 2646.4 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.53 × 0.48 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur System diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.958, T_max = 0.991
20129 measured reflections
2467 independent reflections
1863 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.098
wR(F²) = 0.241
S = 1.14
2467 reflections
169 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.90 (3)	1.99 (3)	2.880 (4)	170 (4)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2002 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809009830/bt2892sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009830/bt2892Isup2.hkl

checkCIF report

Comment top

In the present work, as part of our study of substituent effects on the structures of benzanilides (Gowda et al., 2003; 2008a, b, c), the structure of 2-methyl-N-(2,4-dimethylphenyl)benzamide has been determined. The N—H and C=O bonds in the amide segment are anti to each other (Fig. 1), similar to what is observed in 2-methyl-N-(phenyl)benzamide (Gowda et al., 2008a), 2-methyl-N-(4-methylphenyl)benzamide (Gowda et al., 2008c), 2-methyl-N-(2,6-dimethylphenyl)-benzamide (Gowda et al., 2008b) and other benzanilides. Further, the conformation of the amide oxygen is syn to the ortho-methyl group in the benzoyl ring and the amide hydrogen is syn to the ortho-methyl group in the aniline ring. The anilino and benzoyl rings are almost coplanar with a dihedral angle of 4.9 (3)°. The plane of the amide group makes the angles of 61.3 (3)° with the anilino ring and 58.3 (3)° with the benzoyl ring. A packing diagram of the title compound viewed in the bc-plane is shown in Fig. 2. Molecular chains running along the b-axis are generated by N—H···O hydrogen bonds (Table 1).

Related literature top

For related structures, see Gowda et al. (2003, 2008a,b,c).

Experimental top

The title compound was prepared according to the method described by Gowda et al. (2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Plate-like colourless single crystals of the title compound were obtained by slow evaporation from an ethanol solution (0.5 g in about 30 ml of ethanol) at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. The displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Crystal structure of the title compound viewed in the bc-plane. Chains running along the b axis generated by N—H···O# hydrogen bonds are shown by dashed lines. [Symmetry code (#): -x + 1/2, y - 1/2,z]. H atoms not involved in hydrogen bonding have been omitted.

N-(2,4-Dimethylphenyl)-2-methylbenzamide top

Crystal data top

C₁₆H₁₇NO	F(000) = 1024
M_r = 239.31	D_x = 1.201 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7082 reflections
a = 6.0062 (4) Å	θ = 3.2–27.5°
b = 9.8036 (6) Å	µ = 0.08 mm⁻¹
c = 44.943 (4) Å	T = 295 K
V = 2646.4 (3) Å³	Block, colourless
Z = 8	0.53 × 0.48 × 0.12 mm

Data collection top

Oxford Diffraction Xcalibur System diffractometer	2467 independent reflections
Graphite monochromator	1863 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm^-1	R_int = 0.073
ω scans with κ offsets	θ_max = 25.7°, θ_min = 3.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	h = −7→7
T_min = 0.958, T_max = 0.991	k = −11→11
20129 measured reflections	l = −54→54

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)] = 0.098	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.241	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ²(F_o²) + (0.0735P)² + 4.7656P] where P = (F_o² + 2F_c²)/3
2467 reflections	(Δ/σ)_max < 0.001
169 parameters	Δρ_max = 0.24 e Å⁻³
1 restraint	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₆H₁₇NO	V = 2646.4 (3) Å³
M_r = 239.31	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 6.0062 (4) Å	µ = 0.08 mm⁻¹
b = 9.8036 (6) Å	T = 295 K
c = 44.943 (4) Å	0.53 × 0.48 × 0.12 mm

Data collection top

Oxford Diffraction Xcalibur System diffractometer	2467 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	1863 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.991	R_int = 0.073
20129 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.098	1 restraint
wR(F²) = 0.241	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 0.24 e Å⁻³
2467 reflections	Δρ_min = −0.21 e Å⁻³
169 parameters

Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2008). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C1	0.4332 (7)	0.5763 (4)	0.09991 (8)	0.0446 (9)
C2	0.3831 (7)	0.5294 (4)	0.07156 (9)	0.0470 (9)
C3	0.5158 (7)	0.5746 (4)	0.04829 (9)	0.0501 (10)
H3	0.4813	0.5463	0.0291	0.06*
C4	0.6975 (7)	0.6600 (5)	0.05232 (9)	0.0557 (11)
C5	0.7436 (7)	0.7029 (4)	0.08089 (9)	0.0543 (10)
H5	0.8635	0.761	0.0843	0.065*
C6	0.6148 (7)	0.6611 (4)	0.10447 (9)	0.0501 (10)
H6	0.6498	0.6898	0.1236	0.06*
C7	0.1870 (7)	0.6237 (3)	0.14167 (8)	0.0442 (9)
C8	0.0506 (6)	0.5613 (4)	0.16578 (8)	0.0442 (9)
C9	0.0815 (7)	0.5979 (4)	0.19532 (9)	0.0533 (10)
C10	−0.0551 (9)	0.5371 (5)	0.21657 (10)	0.0712 (14)
H10	−0.0356	0.5587	0.2366	0.085*
C11	−0.2191 (9)	0.4454 (5)	0.20853 (12)	0.0743 (14)
H11	−0.311	0.4081	0.2231	0.089*
C12	−0.2471 (9)	0.4092 (5)	0.17960 (11)	0.0711 (13)
H12	−0.3568	0.3468	0.1743	0.085*
C13	−0.1125 (7)	0.4655 (4)	0.15833 (10)	0.0542 (10)
H13	−0.1298	0.4396	0.1386	0.065*
C14	0.1901 (7)	0.4363 (4)	0.06628 (10)	0.0589 (11)
H14A	0.1679	0.4252	0.0453	0.088*
H14B	0.0585	0.4749	0.075	0.088*
H14C	0.2199	0.3492	0.0752	0.088*
C15	0.8378 (9)	0.7033 (5)	0.02654 (11)	0.0769 (15)
H15A	0.9908	0.7082	0.0326	0.115*
H15B	0.7899	0.7913	0.0197	0.115*
H15C	0.823	0.6381	0.0107	0.115*
C16	0.2558 (10)	0.6978 (5)	0.20471 (10)	0.0754 (14)
H16A	0.4004	0.6625	0.1999	0.113*
H16B	0.2459	0.7124	0.2258	0.113*
H16C	0.2331	0.7827	0.1945	0.113*
N1	0.3000 (6)	0.5350 (3)	0.12468 (7)	0.0491 (9)
H1N	0.287 (7)	0.445 (3)	0.1279 (8)	0.059*
O1	0.1884 (5)	0.7473 (3)	0.13756 (6)	0.0638 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.046 (2)	0.0306 (18)	0.057 (2)	0.0064 (17)	0.0054 (18)	0.0037 (16)
C2	0.043 (2)	0.034 (2)	0.064 (2)	0.0031 (17)	0.0023 (18)	0.0020 (17)
C3	0.052 (2)	0.042 (2)	0.057 (2)	0.001 (2)	−0.0008 (19)	−0.0006 (17)
C4	0.045 (2)	0.058 (3)	0.064 (2)	0.001 (2)	0.0058 (19)	0.010 (2)
C5	0.043 (2)	0.041 (2)	0.079 (3)	−0.0051 (19)	−0.001 (2)	0.002 (2)
C6	0.047 (2)	0.042 (2)	0.060 (2)	0.0015 (18)	−0.0027 (19)	−0.0006 (18)
C7	0.048 (2)	0.0267 (18)	0.058 (2)	0.0048 (17)	−0.0024 (18)	0.0022 (15)
C8	0.045 (2)	0.0311 (18)	0.056 (2)	0.0058 (17)	0.0021 (18)	0.0040 (16)
C9	0.055 (3)	0.041 (2)	0.063 (2)	0.013 (2)	−0.003 (2)	0.0011 (18)
C10	0.088 (4)	0.070 (3)	0.056 (2)	0.025 (3)	0.012 (3)	0.002 (2)
C11	0.073 (3)	0.059 (3)	0.091 (4)	0.006 (3)	0.033 (3)	0.012 (3)
C12	0.056 (3)	0.061 (3)	0.096 (4)	−0.004 (2)	0.014 (3)	0.004 (3)
C13	0.060 (3)	0.032 (2)	0.071 (3)	0.001 (2)	0.004 (2)	0.0011 (18)
C14	0.053 (3)	0.044 (2)	0.080 (3)	−0.013 (2)	0.004 (2)	−0.005 (2)
C15	0.069 (3)	0.077 (3)	0.085 (3)	−0.017 (3)	0.015 (3)	0.011 (3)
C16	0.082 (3)	0.076 (3)	0.068 (3)	0.010 (3)	−0.021 (3)	−0.006 (2)
N1	0.064 (2)	0.0178 (15)	0.0659 (19)	0.0033 (15)	0.0112 (17)	0.0033 (13)
O1	0.080 (2)	0.0284 (14)	0.083 (2)	0.0061 (15)	0.0167 (17)	0.0030 (13)

Geometric parameters (Å, º) top

C1—C6	1.387 (5)	C9—C16	1.494 (7)
C1—C2	1.388 (5)	C10—C11	1.382 (7)
C1—N1	1.430 (5)	C10—H10	0.93
C2—C3	1.388 (5)	C11—C12	1.358 (7)
C2—C14	1.494 (5)	C11—H11	0.93
C3—C4	1.387 (6)	C12—C13	1.369 (6)
C3—H3	0.93	C12—H12	0.93
C4—C5	1.380 (6)	C13—H13	0.93
C4—C15	1.494 (6)	C14—H14A	0.96
C5—C6	1.375 (5)	C14—H14B	0.96
C5—H5	0.93	C14—H14C	0.96
C6—H6	0.93	C15—H15A	0.96
C7—O1	1.225 (4)	C15—H15B	0.96
C7—N1	1.342 (5)	C15—H15C	0.96
C7—C8	1.490 (5)	C16—H16A	0.96
C8—C9	1.388 (5)	C16—H16B	0.96
C8—C13	1.398 (5)	C16—H16C	0.96
C9—C10	1.393 (6)	N1—H1N	0.90 (3)

C6—C1—C2	120.3 (4)	C12—C11—C10	120.6 (5)
C6—C1—N1	119.7 (3)	C12—C11—H11	119.7
C2—C1—N1	120.0 (4)	C10—C11—H11	119.7
C3—C2—C1	117.5 (4)	C11—C12—C13	119.3 (5)
C3—C2—C14	121.4 (4)	C11—C12—H12	120.3
C1—C2—C14	121.1 (4)	C13—C12—H12	120.3
C4—C3—C2	123.1 (4)	C12—C13—C8	121.2 (4)
C4—C3—H3	118.4	C12—C13—H13	119.4
C2—C3—H3	118.4	C8—C13—H13	119.4
C5—C4—C3	117.6 (4)	C2—C14—H14A	109.5
C5—C4—C15	121.5 (4)	C2—C14—H14B	109.5
C3—C4—C15	120.9 (4)	H14A—C14—H14B	109.5
C6—C5—C4	120.9 (4)	C2—C14—H14C	109.5
C6—C5—H5	119.6	H14A—C14—H14C	109.5
C4—C5—H5	119.6	H14B—C14—H14C	109.5
C5—C6—C1	120.5 (4)	C4—C15—H15A	109.5
C5—C6—H6	119.7	C4—C15—H15B	109.5
C1—C6—H6	119.7	H15A—C15—H15B	109.5
O1—C7—N1	123.5 (4)	C4—C15—H15C	109.5
O1—C7—C8	121.3 (3)	H15A—C15—H15C	109.5
N1—C7—C8	115.2 (3)	H15B—C15—H15C	109.5
C9—C8—C13	119.8 (4)	C9—C16—H16A	109.5
C9—C8—C7	121.0 (4)	C9—C16—H16B	109.5
C13—C8—C7	119.2 (3)	H16A—C16—H16B	109.5
C8—C9—C10	117.8 (4)	C9—C16—H16C	109.5
C8—C9—C16	122.3 (4)	H16A—C16—H16C	109.5
C10—C9—C16	120.0 (4)	H16B—C16—H16C	109.5
C11—C10—C9	121.3 (4)	C7—N1—C1	122.8 (3)
C11—C10—H10	119.4	C7—N1—H1N	120 (3)
C9—C10—H10	119.4	C1—N1—H1N	117 (3)

C6—C1—C2—C3	−2.3 (5)	N1—C7—C8—C13	−57.5 (5)
N1—C1—C2—C3	179.0 (3)	C13—C8—C9—C10	−0.4 (6)
C6—C1—C2—C14	179.1 (4)	C7—C8—C9—C10	178.8 (4)
N1—C1—C2—C14	0.4 (5)	C13—C8—C9—C16	178.9 (4)
C1—C2—C3—C4	2.0 (6)	C7—C8—C9—C16	−1.9 (6)
C14—C2—C3—C4	−179.4 (4)	C8—C9—C10—C11	−1.3 (6)
C2—C3—C4—C5	−1.2 (6)	C16—C9—C10—C11	179.4 (4)
C2—C3—C4—C15	178.7 (4)	C9—C10—C11—C12	1.8 (7)
C3—C4—C5—C6	0.7 (6)	C10—C11—C12—C13	−0.6 (7)
C15—C4—C5—C6	−179.2 (4)	C11—C12—C13—C8	−1.1 (7)
C4—C5—C6—C1	−1.0 (6)	C9—C8—C13—C12	1.6 (6)
C2—C1—C6—C5	1.9 (6)	C7—C8—C13—C12	−177.6 (4)
N1—C1—C6—C5	−179.4 (3)	O1—C7—N1—C1	−0.2 (6)
O1—C7—C8—C9	−58.6 (5)	C8—C7—N1—C1	177.8 (4)
N1—C7—C8—C9	123.3 (4)	C6—C1—N1—C7	62.0 (5)
O1—C7—C8—C13	120.6 (4)	C2—C1—N1—C7	−119.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.90 (3)	1.99 (3)	2.880 (4)	170 (4)

Symmetry code: (i) −x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇NO
M_r	239.31
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	6.0062 (4), 9.8036 (6), 44.943 (4)
V (Å³)	2646.4 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.53 × 0.48 × 0.12

Data collection
Diffractometer	Oxford Diffraction Xcalibur System diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.958, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	20129, 2467, 1863
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.098, 0.241, 1.14
No. of reflections	2467
No. of parameters	169
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.21

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.90 (3)	1.99 (3)	2.880 (4)	170 (4)

Symmetry code: (i) −x+1/2, y−1/2, z.

Acknowledgements

MT and JK thank the Grant Agency of the Slovak Republic (grant No. VEGA 1/0817/08) and the Structural Funds, Interreg IIIA, for financial support for the purchase of the diffractometer.

References

Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008a). Acta Cryst. E64, o383. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008b). Acta Cryst. E64, o1605. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230. CAS Google Scholar
Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008c). Acta Cryst. E64, o1494. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar