3,5-Bis[(pyridin-4-yl)meth­oxy]benzoic acid

Lin, H.; Zhang, Y.-P.

doi:10.1107/S1600536812049550

organic compounds

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ISSN: 2056-9890

Volume 69| Part 1| January 2013| Page o77

https://doi.org/10.1107/S1600536812049550

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3,5-Bis[(pyridin-4-yl)methoxy]benzoic acid

Hong Lin ^a ^* and Yi-Ping Zhang ^b

^aJinhua Professional Technical College, No. 1188 Wuzhou Street, Jinhua, Zhejiang 321017, People's Republic of China, and ^bZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China
^*Correspondence e-mail: jh_ll@126.com

(Received 12 November 2012; accepted 3 December 2012; online 12 December 2012)

Single crystals of the title compound, C₁₉H₁₆N₂O₄, were obtained under hydrothermal conditions by an unintended recrystallization of the employed microcrystalline starting material. The [(pyridin-4-yl)methoxy]benzoic acid unit is nearly planar, with a maximum deviation from the least-squares plane of 0.194 (2) Å. This plane is inclined by 35.82 (6)° to that defined by the second (pyridin-4-yl)methoxy group [in which the largest deviation from the least-squares plane is 0.013 (2) Å]. In the crystal, molecules are linked by O—H⋯N hydrogen bonds involving the acid hydroxy group and a pyridine N atom into chains parallel to [-201].

Related literature

For compounds with metal-organic framework structures derived from the title compound, see: Xu et al. (2009 ).

Experimental

Crystal data

C₁₉H₁₆N₂O₄
M_r = 336.34
Monoclinic, P 2₁ /c
a = 11.1523 (6) Å
b = 11.2120 (6) Å
c = 13.9255 (7) Å
β = 102.827 (3)°
V = 1697.79 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.38 × 0.33 × 0.21 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.965, T_max = 0.980
25948 measured reflections
3936 independent reflections
2980 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.132
S = 1.04
3936 reflections
226 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.26 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
O2—H1A⋯N2ⁱ	0.85	1.83	2.6736 (16)	171
Symmetry code: (i) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812049550/wm2702sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049550/wm2702Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812049550/wm2702Isup3.cml

checkCIF report

Comment top

MOFs derived from the 3,5-bis(pyridin-4-ylmethoxy)benzoic acid ligand have been synthesized recently (Xu et al., 2009). During hydrothermal syntheses intended for crystal growth of related systems, crystals of the educt 3,5-bis(pyridin-4-yl-methoxy)benzoic acid, (I), have been unexpectedly obtained.

The molecular structure of (I) is presented in Fig. 1. Atoms O1—O4, C1—C6, C12—C19 and N2 are nearly coplanar (r.m.s. deviation = 0.098 Å; largest deviation from the least-squares plane 0.194 (2) Å); atoms C7—C11, C18 and N1 of the second pyridyl moiety are in another plane (r.m.s. deviation = 0.003 Å; largest deviation from the least-squares plane 0.013 (2) Å). The dihedral angle between the two planes is 35.82 (6)°.

The carboxylic O—H group and neighbouring pyridyl N atoms are involved in O—H···N hydrogen-bonding interactions (Table 1), forming chains extending parallel to [201] (Fig. 2). There are no significant π···π interactions between the aromatic planes of adjacent chains.

Related literature top

For compounds with metal-organic framework structures derived from the title compound, see: Xu et al. (2009).

Experimental top

3,5-bis(pyridin-4-yl-methoxy)benzoic acid was obtained commercially. A mixture of 3,5-bis(pyridin-4-yl-methoxy)benzoic acid (0.5 mmol), CdCl₂^.2.5H₂O (0.25 mmol), and NaOH (0.5 mmol) in H₂O (16 ml) was sealed in a 25 ml stainless steel reactor with a telflon liner and heated at 433 K for 72 h, and then cooled to room temperature at a speed of 5 Kh^-1. Colourless single crystals of (I) were obtained by slow evaporation of the filtrate over a few days.

Structure description top

For compounds with metal-organic framework structures derived from the title compound, see: Xu et al. (2009).

Computing details top

Data collection: SMART (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the one-dimensional chain-like structure of (I).

3,5-Bis[(pyridin-4-yl)methoxy]benzoic acid top

Crystal data top

C₁₉H₁₆N₂O₄	F(000) = 704
M_r = 336.34	D_x = 1.316 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9997 reflections
a = 11.1523 (6) Å	θ = 1.9–27.6°
b = 11.2120 (6) Å	µ = 0.09 mm⁻¹
c = 13.9255 (7) Å	T = 296 K
β = 102.827 (3)°	Block, colourless
V = 1697.79 (15) Å³	0.38 × 0.33 × 0.21 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3936 independent reflections
Radiation source: fine-focus sealed tube	2980 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 27.6°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −13→14
T_min = 0.965, T_max = 0.980	k = −14→14
25948 measured reflections	l = −18→18

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0639P)² + 0.2876P] where P = (F_o² + 2F_c²)/3
3936 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.26 e Å⁻³
1 restraint	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₉H₁₆N₂O₄	V = 1697.79 (15) Å³
M_r = 336.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.1523 (6) Å	µ = 0.09 mm⁻¹
b = 11.2120 (6) Å	T = 296 K
c = 13.9255 (7) Å	0.38 × 0.33 × 0.21 mm
β = 102.827 (3)°

Data collection top

Bruker SMART CCD diffractometer	3936 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	2980 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.980	R_int = 0.025
25948 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	1 restraint
wR(F²) = 0.132	H-atom parameters constrained
S = 1.04	Δρ_max = 0.26 e Å⁻³
3936 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	0.68638 (16)	−0.22020 (13)	0.06179 (12)	0.0777 (4)
N2	−0.01294 (12)	0.70984 (13)	−0.08773 (10)	0.0647 (4)
O1	0.89003 (10)	0.51053 (12)	0.36115 (10)	0.0864 (4)
O2	0.78235 (10)	0.67629 (10)	0.32201 (9)	0.0756 (4)
H1A	0.8458	0.7098	0.3565	0.091*
O3	0.61952 (9)	0.19740 (9)	0.14886 (9)	0.0684 (3)
O4	0.38875 (8)	0.55619 (8)	0.10585 (7)	0.0537 (3)
C1	0.69258 (11)	0.49686 (12)	0.25395 (9)	0.0448 (3)
C2	0.70848 (11)	0.37573 (12)	0.23705 (10)	0.0482 (3)
H2A	0.7807	0.3368	0.2672	0.058*
C3	0.61508 (12)	0.31505 (12)	0.17484 (10)	0.0495 (3)
C4	0.50609 (12)	0.37228 (12)	0.13026 (10)	0.0491 (3)
H4A	0.4432	0.3302	0.0890	0.059*
C5	0.49235 (11)	0.49207 (12)	0.14796 (9)	0.0441 (3)
C6	0.58568 (11)	0.55589 (12)	0.21024 (9)	0.0447 (3)
H6A	0.5761	0.6366	0.2221	0.054*
C7	0.79339 (18)	−0.16440 (16)	0.08353 (15)	0.0779 (5)
H7A	0.8616	−0.2048	0.0720	0.093*
C8	0.81162 (14)	−0.05037 (14)	0.12215 (12)	0.0618 (4)
H8A	0.8892	−0.0155	0.1348	0.074*
C9	0.71223 (12)	0.00998 (12)	0.14135 (9)	0.0473 (3)
C10	0.59962 (14)	−0.04711 (14)	0.11926 (11)	0.0578 (4)
H10A	0.5298	−0.0094	0.1307	0.069*
C11	0.59181 (16)	−0.16036 (15)	0.08012 (13)	0.0687 (4)
H11A	0.5151	−0.1971	0.0657	0.082*
C12	−0.00017 (14)	0.59958 (16)	−0.11826 (12)	0.0647 (4)
H12A	−0.0621	0.5683	−0.1678	0.078*
C13	0.09988 (13)	0.52908 (15)	−0.08048 (10)	0.0558 (4)
H13A	0.1048	0.4520	−0.1040	0.067*
C14	0.19354 (11)	0.57435 (12)	−0.00677 (9)	0.0445 (3)
C15	0.18240 (13)	0.68999 (13)	0.02401 (10)	0.0511 (3)
H15A	0.2440	0.7243	0.0722	0.061*
C16	0.07743 (14)	0.75435 (14)	−0.01820 (12)	0.0612 (4)
H16A	0.0700	0.8321	0.0031	0.073*
C17	0.79843 (12)	0.56116 (13)	0.31786 (11)	0.0541 (3)
C18	0.72785 (12)	0.13267 (12)	0.18610 (11)	0.0522 (3)
H18A	0.7424	0.1273	0.2573	0.063*
H18B	0.7976	0.1723	0.1691	0.063*
C19	0.29911 (11)	0.49396 (12)	0.03536 (10)	0.0497 (3)
H19A	0.2697	0.4258	0.0664	0.060*
H19B	0.3359	0.4649	−0.0171	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0886 (11)	0.0541 (8)	0.0904 (10)	0.0016 (8)	0.0201 (9)	−0.0160 (7)
N2	0.0505 (7)	0.0672 (8)	0.0686 (8)	0.0100 (6)	−0.0036 (6)	0.0160 (7)
O1	0.0504 (6)	0.0758 (8)	0.1111 (10)	0.0056 (6)	−0.0290 (6)	−0.0171 (7)
O2	0.0566 (6)	0.0573 (7)	0.0939 (8)	−0.0075 (5)	−0.0237 (6)	−0.0146 (6)
O3	0.0498 (6)	0.0426 (5)	0.0982 (8)	0.0087 (4)	−0.0150 (5)	−0.0135 (5)
O4	0.0401 (5)	0.0459 (5)	0.0648 (6)	0.0070 (4)	−0.0104 (4)	−0.0112 (4)
C1	0.0367 (6)	0.0487 (7)	0.0453 (6)	−0.0037 (5)	0.0014 (5)	−0.0028 (5)
C2	0.0371 (6)	0.0481 (7)	0.0538 (7)	0.0041 (5)	−0.0016 (5)	0.0013 (6)
C3	0.0427 (7)	0.0416 (7)	0.0598 (8)	0.0021 (5)	0.0017 (6)	−0.0033 (6)
C4	0.0365 (6)	0.0461 (7)	0.0585 (8)	−0.0002 (5)	−0.0030 (5)	−0.0074 (6)
C5	0.0352 (6)	0.0446 (7)	0.0489 (7)	0.0030 (5)	0.0014 (5)	−0.0028 (5)
C6	0.0415 (7)	0.0406 (7)	0.0484 (7)	−0.0010 (5)	0.0022 (5)	−0.0041 (5)
C7	0.0740 (11)	0.0671 (11)	0.0956 (13)	0.0193 (9)	0.0255 (10)	−0.0133 (9)
C8	0.0506 (8)	0.0611 (9)	0.0731 (10)	0.0059 (7)	0.0121 (7)	−0.0047 (7)
C9	0.0500 (7)	0.0447 (7)	0.0442 (6)	0.0053 (6)	0.0044 (5)	0.0015 (5)
C10	0.0510 (8)	0.0553 (8)	0.0660 (9)	0.0029 (6)	0.0107 (7)	−0.0058 (7)
C11	0.0667 (10)	0.0596 (10)	0.0772 (10)	−0.0100 (8)	0.0107 (8)	−0.0104 (8)
C12	0.0496 (8)	0.0758 (11)	0.0586 (8)	0.0018 (7)	−0.0094 (6)	0.0037 (8)
C13	0.0458 (7)	0.0594 (9)	0.0556 (8)	0.0010 (6)	−0.0027 (6)	−0.0052 (6)
C14	0.0368 (6)	0.0499 (7)	0.0444 (6)	0.0030 (5)	0.0038 (5)	0.0013 (5)
C15	0.0459 (7)	0.0497 (8)	0.0533 (7)	0.0037 (6)	0.0014 (6)	0.0009 (6)
C16	0.0577 (9)	0.0513 (8)	0.0718 (9)	0.0105 (7)	0.0083 (7)	0.0068 (7)
C17	0.0425 (7)	0.0551 (8)	0.0578 (8)	−0.0030 (6)	−0.0037 (6)	−0.0074 (6)
C18	0.0453 (7)	0.0486 (7)	0.0569 (8)	0.0060 (6)	−0.0008 (6)	−0.0031 (6)
C19	0.0370 (7)	0.0485 (7)	0.0571 (7)	0.0037 (5)	−0.0036 (6)	−0.0084 (6)

Geometric parameters (Å, º) top

N1—C7	1.322 (2)	C7—H7A	0.9300
N1—C11	1.322 (2)	C8—C9	1.375 (2)
N2—C12	1.325 (2)	C8—H8A	0.9300
N2—C16	1.330 (2)	C9—C10	1.382 (2)
O1—C17	1.2066 (17)	C9—C18	1.5043 (19)
O2—C17	1.3063 (18)	C10—C11	1.377 (2)
O2—H1A	0.8500	C10—H10A	0.9300
O3—C3	1.3716 (17)	C11—H11A	0.9300
O3—C18	1.4060 (16)	C12—C13	1.373 (2)
O4—C5	1.3765 (14)	C12—H12A	0.9300
O4—C19	1.4192 (14)	C13—C14	1.3879 (18)
C1—C6	1.3812 (17)	C13—H13A	0.9300
C1—C2	1.3964 (19)	C14—C15	1.3798 (19)
C1—C17	1.4962 (17)	C14—C19	1.4953 (17)
C2—C3	1.3776 (18)	C15—C16	1.3897 (19)
C2—H2A	0.9300	C15—H15A	0.9300
C3—C4	1.3926 (18)	C16—H16A	0.9300
C4—C5	1.3802 (19)	C18—H18A	0.9700
C4—H4A	0.9300	C18—H18B	0.9700
C5—C6	1.3952 (17)	C19—H19A	0.9700
C6—H6A	0.9300	C19—H19B	0.9700
C7—C8	1.384 (2)

C7—N1—C11	115.73 (15)	C9—C10—H10A	120.3
C12—N2—C16	117.75 (13)	N1—C11—C10	124.16 (16)
C17—O2—H1A	110.9	N1—C11—H11A	117.9
C3—O3—C18	118.52 (10)	C10—C11—H11A	117.9
C5—O4—C19	115.70 (10)	N2—C12—C13	123.37 (14)
C6—C1—C2	121.42 (11)	N2—C12—H12A	118.3
C6—C1—C17	121.41 (12)	C13—C12—H12A	118.3
C2—C1—C17	117.12 (11)	C12—C13—C14	119.14 (14)
C3—C2—C1	118.66 (12)	C12—C13—H13A	120.4
C3—C2—H2A	120.7	C14—C13—H13A	120.4
C1—C2—H2A	120.7	C15—C14—C13	117.94 (12)
O3—C3—C2	125.05 (12)	C15—C14—C19	124.19 (12)
O3—C3—C4	113.87 (11)	C13—C14—C19	117.87 (12)
C2—C3—C4	121.07 (12)	C14—C15—C16	118.82 (13)
C5—C4—C3	119.29 (12)	C14—C15—H15A	120.6
C5—C4—H4A	120.4	C16—C15—H15A	120.6
C3—C4—H4A	120.4	N2—C16—C15	122.96 (14)
O4—C5—C4	123.23 (11)	N2—C16—H16A	118.5
O4—C5—C6	115.90 (11)	C15—C16—H16A	118.5
C4—C5—C6	120.87 (11)	O1—C17—O2	123.51 (13)
C1—C6—C5	118.69 (12)	O1—C17—C1	122.63 (14)
C1—C6—H6A	120.7	O2—C17—C1	113.86 (12)
C5—C6—H6A	120.7	O3—C18—C9	107.95 (11)
N1—C7—C8	124.98 (16)	O3—C18—H18A	110.1
N1—C7—H7A	117.5	C9—C18—H18A	110.1
C8—C7—H7A	117.5	O3—C18—H18B	110.1
C9—C8—C7	118.36 (15)	C9—C18—H18B	110.1
C9—C8—H8A	120.8	H18A—C18—H18B	108.4
C7—C8—H8A	120.8	O4—C19—C14	110.32 (11)
C8—C9—C10	117.45 (13)	O4—C19—H19A	109.6
C8—C9—C18	120.43 (13)	C14—C19—H19A	109.6
C10—C9—C18	122.12 (12)	O4—C19—H19B	109.6
C11—C10—C9	119.32 (14)	C14—C19—H19B	109.6
C11—C10—H10A	120.3	H19A—C19—H19B	108.1

C6—C1—C2—C3	0.4 (2)	C18—C9—C10—C11	−178.76 (14)
C17—C1—C2—C3	−176.99 (13)	C7—N1—C11—C10	0.0 (3)
C18—O3—C3—C2	−1.4 (2)	C9—C10—C11—N1	0.1 (3)
C18—O3—C3—C4	177.06 (13)	C16—N2—C12—C13	1.3 (3)
C1—C2—C3—O3	177.65 (14)	N2—C12—C13—C14	−0.3 (3)
C1—C2—C3—C4	−0.7 (2)	C12—C13—C14—C15	−1.1 (2)
O3—C3—C4—C5	−177.79 (13)	C12—C13—C14—C19	177.87 (14)
C2—C3—C4—C5	0.8 (2)	C13—C14—C15—C16	1.5 (2)
C19—O4—C5—C4	−5.20 (19)	C19—C14—C15—C16	−177.46 (13)
C19—O4—C5—C6	174.18 (11)	C12—N2—C16—C15	−0.9 (2)
C3—C4—C5—O4	178.92 (13)	C14—C15—C16—N2	−0.5 (2)
C3—C4—C5—C6	−0.4 (2)	C6—C1—C17—O1	175.83 (15)
C2—C1—C6—C5	−0.1 (2)	C2—C1—C17—O1	−6.8 (2)
C17—C1—C6—C5	177.20 (12)	C6—C1—C17—O2	−4.3 (2)
O4—C5—C6—C1	−179.31 (11)	C2—C1—C17—O2	173.04 (13)
C4—C5—C6—C1	0.1 (2)	C3—O3—C18—C9	−176.09 (13)
C11—N1—C7—C8	−0.7 (3)	C8—C9—C18—O3	147.29 (14)
N1—C7—C8—C9	1.1 (3)	C10—C9—C18—O3	−33.63 (18)
C7—C8—C9—C10	−0.9 (2)	C5—O4—C19—C14	−178.29 (11)
C7—C8—C9—C18	178.20 (15)	C15—C14—C19—O4	−3.97 (19)
C8—C9—C10—C11	0.3 (2)	C13—C14—C19—O4	177.08 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1A···N2ⁱ	0.85	1.83	2.6736 (16)	171

Symmetry code: (i) x+1, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆N₂O₄
M_r	336.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.1523 (6), 11.2120 (6), 13.9255 (7)
β (°)	102.827 (3)
V (Å³)	1697.79 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.38 × 0.33 × 0.21

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.965, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	25948, 3936, 2980
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.132, 1.04
No. of reflections	3936
No. of parameters	226
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.25

Computer programs: SMART (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1A···N2ⁱ	0.85	1.83	2.6736 (16)	170.9

Symmetry code: (i) x+1, −y+3/2, z+1/2.

References

Bruker (2006). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, G. J., Zhao, Y. H., Shao, K. Z., Lan, Y. Q., Wang, X. L., Su, Z. M. & Yan, L. K. (2009). CrystEngComm, 11, 1842–1847. Web of Science CSD CrossRef CAS Google Scholar

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Volume 69| Part 1| January 2013| Page o77

https://doi.org/10.1107/S1600536812049550

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