Crystal structure of 3-(morpholin-4-yl)-1-phenyl-3-(pyridin-2-yl)propan-1-one

Ahamed, F.M.M.; Padusha, M.S.A.; Gunasekaran, B.

doi:10.1107/S2056989014026292

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 1| January 2015| Pages o24-o25

https://doi.org/10.1107/S2056989014026292

Open

access

Crystal structure of 3-(morpholin-4-yl)-1-phenyl-3-(pyridin-2-yl)propan-1-one

F. M. Mashood Ahamed,^a M. Syed Ali Padusha ^a and B. Gunasekaran ^b ^*

^aPG and Research Dept of Chemistry, Jamal Mohamed College (Autonomous), Tiruchirappalli, Tamil Nadu 620 020, India, and ^bDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203 Tamil Nadu, India
^*Correspondence e-mail: phdguna@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 26 November 2014; accepted 30 November 2014; online 1 January 2015)

In the title compound C₁₈H₂₀N₂O₂, the morpholine ring adopts a chair conformation with the exocyclic N—C bond in an equatorial orientation. The N atom of the morpholine ring and the C atom of the carbonyl group are in an anti conformation about the central C—C bond [torsion angle = −162.92 (11)°] and the dihedral angle between the planes of the benzene ring and the pyridine ring is 83.30 (5)°. In the crystal, pairs of very weak C—H⋯π interactions link the molecules into inversion dimers.

Keywords: crystal structure; morpholin-4-yl; pyridin-2-yl; propan-1-one; biological activity.

CCDC reference: 1036843

1. Related literature

For background to the biological activity of morpholine derivatives, see: Panneerselvam et al. (2009 ); Subhashini et al. (2013 ); Sawant et al. (2013 ); Dave & Sasaki (2006 ); For related structures, see: Chen et al. (2011 ); Meti et al. (2013 );

2. Experimental

2.1. Crystal data

C₁₈H₂₀N₂O₂
M_r = 296.36
Orthorhombic, P b c a
a = 12.4554 (6) Å
b = 8.2204 (4) Å
c = 30.6681 (17) Å
V = 3140.1 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.20 × 0.15 × 0.10 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.954, T_max = 0.975
16093 measured reflections
3812 independent reflections
2547 reflections with I > 2σ(I)
R_int = 0.028

2.3. Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.111
S = 1.03
3812 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C10–C14/N1 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg2ⁱ	0.93	2.90	3.780 (6)	159
Symmetry code: (i) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1036843

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989014026292/hb7328sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989014026292/hb7328Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989014026292/hb7328Isup3.cml

checkCIF report

Comment top

Morpholines are six-membered heterocycles featuring both cyclic amine and ether functional group. These compounds possess important applications in pharmaceuticals and in industries (Panneerselvam et al., 2009; Subhashini et al., 2013). Chiral morpholine derivatives have found numerous applications in asymmetric synthesis as chiral auxiliaries as well as chiral ligands (Sawant et al., 2013; Dave & Sasaki 2006).

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Chen et al., 2011; Meti et al., 2013). The morpholine (N2/O2/C15—C18)ring adopts a chair conformation [Q = 0.5756 (3) Å, Θ = 179.09 (3)°, φ = 332.57 (5)°]. The phenyl ring makes a dihedral angles of 83.30 (5) ° with the pyridine ring. In the crystal, a weak C—H···π interaction is observed.

Related literature top

For background to the biological activity of morpholine derivatives, see: Panneerselvam et al. (2009); Subhashini et al. (2013); Sawant et al. (2013); Dave & Sasaki (2006); For related structures, see: Chen et al. (2011); Meti et al. (2013);

Experimental top

To an ethanolic solution of acetophenone (3.0 ml, 0.025 mol) taken in a round bottom flask, morpholine (2.1 ml, 0.025 mol) and pyridine-2-carboldehyde (2.6 ml, 0.025 mol) were added. The reaction mixture was kept over a magnetic stirrer and stirred well in an ice cold condition for 3 hr. The colourless solid formed was filtered and washed several times with petroleum ether (40–60%). The crude solid obtained was dried and recrystallized using absolute alcohol. The recrystallized product was dried over vacuum. The yield is 78% and MP is 445 K.

Structure description top

For background to the biological activity of morpholine derivatives, see: Panneerselvam et al. (2009); Subhashini et al. (2013); Sawant et al. (2013); Dave & Sasaki (2006); For related structures, see: Chen et al. (2011); Meti et al. (2013);

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms.

3-(Morpholin-4-yl)-1-phenyl-3-(pyridin-2-yl)propan-1-one top

Crystal data top

C₁₈H₂₀N₂O₂	F(000) = 1264
M_r = 296.36	D_x = 1.254 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3812 reflections
a = 12.4554 (6) Å	θ = 1.3–28.4°
b = 8.2204 (4) Å	µ = 0.08 mm⁻¹
c = 30.6681 (17) Å	T = 295 K
V = 3140.1 (3) Å³	Block, colourless
Z = 8	0.20 × 0.15 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	3812 independent reflections
Radiation source: fine-focus sealed tube	2547 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 0 pixels mm^-1	θ_max = 28.4°, θ_min = 1.3°
ω and φ scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→10
T_min = 0.954, T_max = 0.975	l = −35→40
16093 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0416P)² + 0.6298P] where P = (F_o² + 2F_c²)/3
3812 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₈H₂₀N₂O₂	V = 3140.1 (3) Å³
M_r = 296.36	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.4554 (6) Å	µ = 0.08 mm⁻¹
b = 8.2204 (4) Å	T = 295 K
c = 30.6681 (17) Å	0.20 × 0.15 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	3812 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2547 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.975	R_int = 0.028
16093 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	Δρ_max = 0.14 e Å⁻³
3812 reflections	Δρ_min = −0.16 e Å⁻³
199 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.42802 (13)	−0.1732 (2)	0.02138 (5)	0.0604 (4)
H1	0.5020	−0.1642	0.0182	0.073*
C2	0.36782 (16)	−0.2413 (2)	−0.01152 (6)	0.0746 (5)
H2	0.4013	−0.2768	−0.0369	0.089*
C3	0.25900 (16)	−0.2571 (2)	−0.00707 (5)	0.0680 (5)
H3	0.2186	−0.3050	−0.0291	0.082*
C4	0.21022 (13)	−0.2020 (2)	0.02998 (6)	0.0653 (5)
H4	0.1362	−0.2121	0.0330	0.078*
C5	0.26935 (12)	−0.13170 (19)	0.06292 (5)	0.0529 (4)
H5	0.2350	−0.0932	0.0878	0.063*
C6	0.37980 (11)	−0.11808 (15)	0.05909 (4)	0.0412 (3)
C7	0.44770 (10)	−0.04735 (16)	0.09421 (4)	0.0417 (3)
C8	0.39381 (10)	0.03707 (17)	0.13181 (4)	0.0429 (3)
H8A	0.3510	−0.0418	0.1477	0.051*
H8B	0.3453	0.1190	0.1204	0.051*
C9	0.47105 (9)	0.11758 (15)	0.16326 (4)	0.0364 (3)
H9	0.5269	0.0372	0.1697	0.044*
C10	0.52724 (10)	0.26260 (15)	0.14299 (4)	0.0368 (3)
C11	0.51464 (16)	0.4990 (2)	0.10454 (6)	0.0666 (5)
H11	0.4726	0.5746	0.0898	0.080*
C12	0.62216 (16)	0.5287 (2)	0.10752 (6)	0.0678 (5)
H12	0.6520	0.6215	0.0951	0.081*
C13	0.68473 (13)	0.4190 (2)	0.12904 (5)	0.0610 (5)
H13	0.7585	0.4344	0.1313	0.073*
C14	0.63651 (11)	0.28526 (18)	0.14735 (5)	0.0452 (3)
H14	0.6775	0.2099	0.1627	0.054*
C15	0.33073 (11)	0.2736 (2)	0.20287 (5)	0.0532 (4)
H15A	0.2787	0.2424	0.1809	0.064*
H15B	0.3602	0.3787	0.1949	0.064*
C16	0.27665 (12)	0.2851 (2)	0.24674 (6)	0.0662 (5)
H16A	0.2195	0.3651	0.2453	0.079*
H16B	0.2447	0.1808	0.2539	0.079*
C17	0.43388 (14)	0.2128 (2)	0.28202 (5)	0.0632 (4)
H17A	0.4040	0.1078	0.2898	0.076*
H17B	0.4846	0.2440	0.3045	0.076*
C18	0.49150 (11)	0.19882 (18)	0.23921 (4)	0.0462 (3)
H18A	0.5247	0.3021	0.2320	0.055*
H18B	0.5477	0.1176	0.2415	0.055*
N1	0.46563 (10)	0.36867 (15)	0.12143 (4)	0.0526 (3)
N2	0.41661 (8)	0.15290 (13)	0.20488 (4)	0.0394 (3)
O1	0.54495 (8)	−0.05833 (15)	0.09246 (4)	0.0655 (3)
O2	0.35010 (10)	0.32957 (14)	0.27995 (4)	0.0678 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0564 (9)	0.0742 (11)	0.0506 (9)	−0.0007 (8)	0.0083 (8)	−0.0126 (8)
C2	0.0842 (13)	0.0925 (14)	0.0470 (10)	−0.0019 (11)	0.0067 (9)	−0.0220 (9)
C3	0.0815 (12)	0.0728 (11)	0.0497 (9)	−0.0123 (10)	−0.0134 (9)	−0.0073 (9)
C4	0.0567 (9)	0.0784 (12)	0.0607 (10)	−0.0166 (9)	−0.0049 (8)	−0.0085 (9)
C5	0.0495 (9)	0.0615 (9)	0.0477 (8)	−0.0098 (7)	0.0030 (7)	−0.0074 (7)
C6	0.0473 (7)	0.0366 (7)	0.0399 (7)	−0.0009 (6)	0.0012 (6)	0.0008 (6)
C7	0.0410 (7)	0.0392 (7)	0.0449 (8)	0.0005 (6)	0.0027 (6)	0.0003 (6)
C8	0.0379 (7)	0.0446 (7)	0.0461 (8)	−0.0049 (6)	0.0040 (6)	−0.0039 (6)
C9	0.0328 (6)	0.0363 (7)	0.0402 (7)	0.0024 (5)	0.0011 (5)	0.0002 (6)
C10	0.0376 (7)	0.0382 (7)	0.0346 (6)	−0.0004 (5)	0.0020 (5)	−0.0025 (5)
C11	0.0910 (13)	0.0498 (9)	0.0589 (10)	−0.0004 (9)	−0.0032 (9)	0.0166 (8)
C12	0.0926 (13)	0.0549 (10)	0.0559 (10)	−0.0279 (10)	0.0183 (9)	0.0017 (8)
C13	0.0555 (9)	0.0663 (10)	0.0613 (10)	−0.0229 (8)	0.0155 (8)	−0.0162 (9)
C14	0.0389 (7)	0.0512 (8)	0.0456 (8)	−0.0027 (6)	0.0030 (6)	−0.0067 (7)
C15	0.0404 (7)	0.0569 (9)	0.0624 (10)	0.0062 (7)	0.0048 (7)	−0.0090 (8)
C16	0.0500 (9)	0.0641 (10)	0.0844 (12)	−0.0057 (8)	0.0237 (9)	−0.0198 (9)
C17	0.0810 (11)	0.0612 (10)	0.0473 (9)	−0.0109 (9)	0.0080 (8)	−0.0065 (8)
C18	0.0483 (8)	0.0451 (8)	0.0453 (8)	−0.0029 (7)	−0.0002 (6)	−0.0014 (6)
N1	0.0530 (7)	0.0496 (7)	0.0553 (7)	0.0018 (6)	−0.0067 (6)	0.0125 (6)
N2	0.0355 (5)	0.0409 (6)	0.0419 (6)	−0.0012 (5)	0.0040 (5)	−0.0024 (5)
O1	0.0412 (6)	0.0847 (9)	0.0707 (8)	0.0064 (5)	0.0016 (5)	−0.0247 (6)
O2	0.0733 (7)	0.0648 (7)	0.0654 (7)	−0.0114 (6)	0.0215 (6)	−0.0235 (6)

Geometric parameters (Å, º) top

C1—C2	1.376 (2)	C11—N1	1.338 (2)
C1—C6	1.380 (2)	C11—C12	1.364 (3)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.368 (3)	C12—C13	1.362 (2)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.366 (2)	C13—C14	1.373 (2)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.377 (2)	C14—H14	0.9300
C4—H4	0.9300	C15—N2	1.4604 (17)
C5—C6	1.3852 (19)	C15—C16	1.508 (2)
C5—H5	0.9300	C15—H15A	0.9700
C6—C7	1.4878 (19)	C15—H15B	0.9700
C7—O1	1.2159 (15)	C16—O2	1.417 (2)
C7—C8	1.5039 (19)	C16—H16A	0.9700
C8—C9	1.5146 (18)	C16—H16B	0.9700
C8—H8A	0.9700	C17—O2	1.419 (2)
C8—H8B	0.9700	C17—C18	1.500 (2)
C9—N2	1.4741 (16)	C17—H17A	0.9700
C9—C10	1.5157 (18)	C17—H17B	0.9700
C9—H9	0.9800	C18—N2	1.4565 (17)
C10—N1	1.3365 (17)	C18—H18A	0.9700
C10—C14	1.3803 (17)	C18—H18B	0.9700

C2—C1—C6	120.73 (15)	C13—C12—C11	118.42 (15)
C2—C1—H1	119.6	C13—C12—H12	120.8
C6—C1—H1	119.6	C11—C12—H12	120.8
C3—C2—C1	120.36 (16)	C12—C13—C14	118.55 (15)
C3—C2—H2	119.8	C12—C13—H13	120.7
C1—C2—H2	119.8	C14—C13—H13	120.7
C4—C3—C2	119.47 (16)	C13—C14—C10	119.99 (15)
C4—C3—H3	120.3	C13—C14—H14	120.0
C2—C3—H3	120.3	C10—C14—H14	120.0
C3—C4—C5	120.76 (15)	N2—C15—C16	109.39 (13)
C3—C4—H4	119.6	N2—C15—H15A	109.8
C5—C4—H4	119.6	C16—C15—H15A	109.8
C4—C5—C6	120.18 (14)	N2—C15—H15B	109.8
C4—C5—H5	119.9	C16—C15—H15B	109.8
C6—C5—H5	119.9	H15A—C15—H15B	108.2
C1—C6—C5	118.48 (13)	O2—C16—C15	111.65 (12)
C1—C6—C7	119.19 (12)	O2—C16—H16A	109.3
C5—C6—C7	122.33 (12)	C15—C16—H16A	109.3
O1—C7—C6	120.35 (13)	O2—C16—H16B	109.3
O1—C7—C8	120.85 (12)	C15—C16—H16B	109.3
C6—C7—C8	118.80 (11)	H16A—C16—H16B	108.0
C7—C8—C9	113.98 (10)	O2—C17—C18	111.37 (13)
C7—C8—H8A	108.8	O2—C17—H17A	109.4
C9—C8—H8A	108.8	C18—C17—H17A	109.4
C7—C8—H8B	108.8	O2—C17—H17B	109.4
C9—C8—H8B	108.8	C18—C17—H17B	109.4
H8A—C8—H8B	107.7	H17A—C17—H17B	108.0
N2—C9—C8	110.20 (10)	N2—C18—C17	110.24 (12)
N2—C9—C10	114.37 (10)	N2—C18—H18A	109.6
C8—C9—C10	112.07 (11)	C17—C18—H18A	109.6
N2—C9—H9	106.6	N2—C18—H18B	109.6
C8—C9—H9	106.6	C17—C18—H18B	109.6
C10—C9—H9	106.6	H18A—C18—H18B	108.1
N1—C10—C14	121.74 (13)	C10—N1—C11	116.89 (13)
N1—C10—C9	116.80 (11)	C18—N2—C15	108.87 (11)
C14—C10—C9	121.45 (12)	C18—N2—C9	112.48 (10)
N1—C11—C12	124.40 (17)	C15—N2—C9	115.74 (11)
N1—C11—H11	117.8	C16—O2—C17	109.40 (12)
C12—C11—H11	117.8

C6—C1—C2—C3	−0.8 (3)	N1—C11—C12—C13	0.0 (3)
C1—C2—C3—C4	1.2 (3)	C11—C12—C13—C14	−1.1 (2)
C2—C3—C4—C5	−0.3 (3)	C12—C13—C14—C10	1.3 (2)
C3—C4—C5—C6	−0.9 (3)	N1—C10—C14—C13	−0.4 (2)
C2—C1—C6—C5	−0.5 (2)	C9—C10—C14—C13	−179.19 (13)
C2—C1—C6—C7	179.11 (16)	N2—C15—C16—O2	59.10 (17)
C4—C5—C6—C1	1.3 (2)	O2—C17—C18—N2	−58.71 (16)
C4—C5—C6—C7	−178.26 (14)	C14—C10—N1—C11	−0.6 (2)
C1—C6—C7—O1	−10.1 (2)	C9—C10—N1—C11	178.23 (13)
C5—C6—C7—O1	169.48 (15)	C12—C11—N1—C10	0.8 (3)
C1—C6—C7—C8	170.08 (13)	C17—C18—N2—C15	57.48 (15)
C5—C6—C7—C8	−10.3 (2)	C17—C18—N2—C9	−172.87 (12)
O1—C7—C8—C9	5.6 (2)	C16—C15—N2—C18	−57.27 (15)
C6—C7—C8—C9	−174.59 (11)	C16—C15—N2—C9	174.89 (11)
C7—C8—C9—N2	−162.92 (11)	C8—C9—N2—C18	168.06 (11)
C7—C8—C9—C10	68.50 (15)	C10—C9—N2—C18	−64.62 (14)
N2—C9—C10—N1	−79.35 (15)	C8—C9—N2—C15	−65.92 (14)
C8—C9—C10—N1	47.00 (15)	C10—C9—N2—C15	61.40 (14)
N2—C9—C10—C14	99.47 (14)	C15—C16—O2—C17	−58.86 (18)
C8—C9—C10—C14	−134.18 (13)	C18—C17—O2—C16	58.37 (16)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C10–C14/N1 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg2ⁱ	0.93	2.90	3.780 (6)	159

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C10–C14/N1 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg2ⁱ	0.93	2.90	3.780 (6)	159

Symmetry code: (i) −x, −y+1, −z.

Acknowledgements

FMMA acknowledges the PG and Research Department of Chemistry and the Management of Jamal Mohamed College (Autonomous) for their kind support.

References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, X.-Y., Zhao, M.-M., Qian, X. & Hou, S.-G. (2011). Acta Cryst. E67, o3484. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dave, R. & Sasaki, N. A. (2006). Tetrahedron Asymmetry, 17, 388–401. Web of Science CrossRef CAS Google Scholar
Meti, G. Y., Kamble, R. R., Ravi, A. J., Arunkashi, H. K. & Devarajegowda, H. C. (2013). Acta Cryst. E69, o129. CSD CrossRef IUCr Journals Google Scholar
Panneerselvam, P., Priya, M., Gnanarupa, , Kumar, N., Ramesh, & Saravanan, G. (2009). Indian J. Pharm. Sci. 71, 428–432. Google Scholar
Sawant, R. T., Stevenson, J., Odell, L. R. & Arvidsson, P. I. (2013). Tetrahedron Asymmetry, 24, 134–141. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. 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
Subhashini, N. J. P., Amanaganti, J., Boddu, L. & Acharya Nagarjuna, P. (2013). J. Chem. Pharm. Res. 5, 140–147. CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 1| January 2015| Pages o24-o25

https://doi.org/10.1107/S2056989014026292

Open

access