4-Amino­benzoic acid–1,2-bis­(4-pyrid­yl)ethane (2/1)

Shen, F.M.; Lush, S.F.

doi:10.1107/S1600536810020337

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1551

doi:10.1107/S1600536810020337

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4-Aminobenzoic acid–1,2-bis(4-pyridyl)ethane (2/1)

Fwu Ming Shen ^a and Shie Fu Lush ^b ^*

^aDepartment of Biotechnology, Yuanpei University, HsinChu, Taiwan 30015, and ^bDepartment of Medical Laboratory Science Biotechnology, Yuanpei University, HsinChu, Taiwan 30015
^*Correspondence e-mail: lush@mail.ypu.edu.tw

(Received 29 April 2010; accepted 28 May 2010; online 5 June 2010)

In the title compound, C₁₂H₁₂N₂·2C₇H₇NO₂, the 4-aminobenzoic acid molecules are linked by O—H⋯N hydrogen bonds to 1,2-bis(4-pyridyl)ethane, forming linear hydrogen bonded chains parallel to [2 $[\overline{1}]$ 1]. The structure exhibits a hydrogen-bonding network involving COOH⋯N(pyridyl) and amine and carboxylic N—H⋯ O interactions. In addition, π–π stacking interactions [centroid–centroid distance = 3.8622 (14) Å] are also present.

Related literature

For linear hydrogen bonding associations involving 4-aminobenzoic acid, see: Smith et al. (1997 ). For related structures, see: Smith et al. (2000 , 2005 ); Lynch & McClenaghan (2001 ). For hydrogen-bond motifs, see: Etter et al. (1990 ).

Experimental

Crystal data

C₁₂H₁₂N₂·2C₇H₇NO₂
M_r = 458.51
Monoclinic, P 2₁ /c
a = 7.3556 (10) Å
b = 23.230 (3) Å
c = 7.9373 (11) Å
β = 115.579 (2)°
V = 1223.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 297 K
0.76 × 0.34 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SMART; Bruker, 2000 ) T_min = 0.674, T_max = 1.000
6871 measured reflections
2406 independent reflections
1530 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.165
S = 1.03
2406 reflections
162 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.90 (3)	2.14 (3)	3.030 (3)	171 (3)
N1—H1B⋯O1ⁱⁱ	0.93 (3)	2.16 (3)	3.081 (3)	172 (2)
O2—H2A⋯N2ⁱⁱⁱ	0.90	1.72	2.613 (2)	173
Symmetry codes: (i) x+1, y, z+1; (ii) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x-1, y, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020337/pb2029sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810020337/pb2029Isup2.hkl

checkCIF report

Comment top

4-Aminobenzoic acid is a useful ligand for structure extension through both the carboxylic acid and amine functional groups, forming linear hydrogen bonding associations (Smith et al., 2005). Other related reports with 4-aminobenzoic acid and Lewis base such as 4-(4-nitrobenzyl)pyridine (Smith, 1997), 4-aminobenzonitrile (Smith et al., 2000) and 2-amino-4-(4-pyridyl)pyrimidine (Lynch & McClenaghan, 2001).

We present here the crystal structure analysis of the 2:1 4-aminobenzoic acid and 1,2-bis(4-pyridyl)ethane adduct (Fig 1). The structure of the title compound comprises two 4-aminobenzoic acid molecules and one 1,2-bis(4-pyridyl)ethane molecule, with no proton transfer. In the structure, the molecules associate 4-aminobenzoic acid and 1,2-bis(4-pyridyl)ethane via carboxylic and pyridine group O—H···N [ O···N 2.613 (2) Å ] D₂²12( Etter et al., 1990), forming linear hydrogen bonding parallel to [ 2 1 1], further connect into a three dimensional network via amine and carboxylic N—H··· O [N···O 3.030 (3) and 3.081 (3) Å ], respectively.

The title compound's supramolecular structure can be readily analyzed in terms of pyridyl atom N2 acts as hydrogen-bond donor to carboxyl atom O2. Similarly, O1 acts as hydrogen-bond donor to amino group N1, respectively (Table 1 and Fig. 2). Furthermore, p -p ring stacking interaction is between neighboring heteraromatic ring in the structure. The distance between Cg1 (N2/C8—C12)···Cg1ⁱ is 3.8622 (14) Å[ symmetry code: (i) = 2-X,1-Y,1-Z].

Related literature top

For linear hydrogen bonding associations involving 4-aminobenzoic acid, see: Smith et al. (1997). For related structures, see: Smith et al. (2000, 2005); Lynch & McClenaghan (2001). . For hydrogen-bond motifs, see: Etter et al. (1990).

Experimental top

The 4-aminobenzoic acid (0.137 mg, 1.0 mmol) and 1,2-bis(4-pyridyl)ethane (184 mg, 1.0 mmol) were dissolved in 20 ml 50% methanol-water, the solution was refluxed for 30 min. The filtered solution was transferred to a 25 ml tube after one week at room temperature, and colorless transparent crystals formed (yield 60.48%).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The molecular packing for the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

4-Aminobenzoic acid–1,2-bis(4-pyridyl)ethane (2/1) top

Crystal data top

C₁₂H₁₂N₂·2C₇H₇NO₂	F(000) = 484
M_r = 458.51	D_x = 1.239 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2347 reflections
a = 7.3556 (10) Å	θ = 3.0–23.7°
b = 23.230 (3) Å	µ = 0.09 mm⁻¹
c = 7.9373 (11) Å	T = 297 K
β = 115.579 (2)°	Parallelepiped, colorless
V = 1223.3 (3) Å³	0.76 × 0.34 × 0.22 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	2406 independent reflections
Radiation source: fine-focus sealed tube	1530 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
phi and ω scans	θ_max = 26.1°, θ_min = 1.8°
Absorption correction: multi-scan (SMART; Bruker, 2000)	h = −9→5
T_min = 0.674, T_max = 1.000	k = −27→28
6871 measured reflections	l = −9→9

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.165	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0959P)² + 0.0431P] where P = (F_o² + 2F_c²)/3
2406 reflections	(Δ/σ)_max < 0.001
162 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³
0 constraints

Crystal data top

C₁₂H₁₂N₂·2C₇H₇NO₂	V = 1223.3 (3) Å³
M_r = 458.51	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.3556 (10) Å	µ = 0.09 mm⁻¹
b = 23.230 (3) Å	T = 297 K
c = 7.9373 (11) Å	0.76 × 0.34 × 0.22 mm
β = 115.579 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2406 independent reflections
Absorption correction: multi-scan (SMART; Bruker, 2000)	1530 reflections with I > 2σ(I)
T_min = 0.674, T_max = 1.000	R_int = 0.032
6871 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.165	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.21 e Å⁻³
2406 reflections	Δρ_min = −0.23 e Å⁻³
162 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
N2	1.1453 (2)	0.43421 (8)	0.3904 (2)	0.0738 (7)
C8	1.0950 (3)	0.48682 (10)	0.3233 (3)	0.0783 (8)
C9	0.8987 (3)	0.50396 (11)	0.2231 (4)	0.0864 (9)
C10	0.7437 (3)	0.46541 (11)	0.1882 (3)	0.0739 (8)
C11	0.7978 (3)	0.41122 (10)	0.2571 (3)	0.0806 (8)
C12	0.9970 (3)	0.39735 (10)	0.3566 (3)	0.0826 (9)
C13	0.5251 (3)	0.48182 (15)	0.0801 (4)	0.1066 (13)
O1	0.4674 (2)	0.33090 (7)	0.4157 (2)	0.0841 (5)
O2	0.51671 (19)	0.40480 (7)	0.6066 (2)	0.0837 (6)
N1	1.3716 (3)	0.28863 (10)	1.0252 (3)	0.0824 (8)
C1	0.5750 (3)	0.35702 (8)	0.5572 (3)	0.0624 (6)
C2	0.7798 (3)	0.33843 (8)	0.6832 (2)	0.0560 (6)
C3	0.8914 (3)	0.36554 (8)	0.8520 (3)	0.0621 (6)
C4	1.0858 (3)	0.34892 (8)	0.9655 (3)	0.0649 (6)
C5	1.1749 (3)	0.30406 (8)	0.9143 (3)	0.0601 (6)
C6	1.0617 (3)	0.27578 (9)	0.7479 (3)	0.0722 (7)
C7	0.8687 (3)	0.29233 (9)	0.6355 (3)	0.0690 (7)
H8A	1.19710	0.51350	0.34500	0.0940*
H9A	0.87020	0.54150	0.17880	0.1040*
H11A	0.69910	0.38350	0.23650	0.0970*
H12A	1.02950	0.36010	0.40280	0.0990*
H13A	0.44700	0.44670	0.03900	0.1280*
H13B	0.48190	0.50100	0.16510	0.1280*
H1A	1.413 (4)	0.3021 (12)	1.142 (4)	0.108 (9)*
H1B	1.409 (3)	0.2543 (12)	0.988 (3)	0.095 (8)*
H2A	0.38730	0.41220	0.52780	0.1600*
H3A	0.83380	0.39560	0.88940	0.0750*
H4A	1.15800	0.36800	1.07780	0.0780*
H6A	1.11810	0.24500	0.71210	0.0870*
H7A	0.79550	0.27240	0.52510	0.0830*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0497 (10)	0.0777 (12)	0.0824 (12)	0.0081 (8)	0.0176 (9)	0.0039 (9)
C8	0.0490 (11)	0.0770 (14)	0.0935 (16)	−0.0026 (10)	0.0163 (11)	0.0066 (12)
C9	0.0549 (13)	0.0798 (15)	0.1084 (18)	0.0100 (10)	0.0201 (12)	0.0279 (13)
C10	0.0445 (10)	0.0941 (16)	0.0755 (13)	0.0038 (10)	0.0189 (9)	0.0124 (11)
C11	0.0565 (13)	0.0847 (15)	0.0937 (15)	−0.0058 (10)	0.0260 (12)	0.0087 (12)
C12	0.0670 (14)	0.0707 (13)	0.1014 (17)	0.0099 (11)	0.0281 (13)	0.0117 (12)
C13	0.0498 (13)	0.146 (3)	0.110 (2)	0.0138 (13)	0.0212 (13)	0.0438 (17)
O1	0.0607 (8)	0.0805 (10)	0.0741 (9)	−0.0025 (7)	−0.0058 (7)	−0.0085 (8)
O2	0.0553 (8)	0.0796 (10)	0.0888 (11)	0.0151 (7)	0.0052 (7)	−0.0106 (8)
N1	0.0556 (11)	0.0881 (14)	0.0825 (14)	0.0129 (10)	0.0100 (10)	0.0009 (11)
C1	0.0496 (10)	0.0616 (11)	0.0620 (11)	−0.0040 (8)	0.0110 (9)	0.0041 (9)
C2	0.0480 (10)	0.0548 (10)	0.0557 (10)	−0.0022 (8)	0.0134 (8)	0.0004 (8)
C3	0.0574 (11)	0.0591 (11)	0.0592 (11)	0.0088 (8)	0.0152 (9)	−0.0038 (9)
C4	0.0570 (11)	0.0638 (11)	0.0546 (10)	0.0021 (9)	0.0060 (9)	−0.0047 (9)
C5	0.0483 (10)	0.0596 (11)	0.0627 (11)	0.0042 (8)	0.0147 (9)	0.0075 (9)
C6	0.0662 (12)	0.0703 (12)	0.0705 (12)	0.0141 (10)	0.0206 (10)	−0.0085 (10)
C7	0.0628 (12)	0.0690 (12)	0.0593 (11)	0.0029 (9)	0.0114 (9)	−0.0099 (9)

Geometric parameters (Å, º) top

O1—C1	1.220 (3)	C11—H11A	0.9300
O2—C1	1.310 (3)	C12—H12A	0.9300
O2—H2A	0.9000	C13—H13B	0.9700
N2—C12	1.320 (3)	C13—H13A	0.9700
N2—C8	1.321 (3)	C1—C2	1.468 (3)
N1—C5	1.377 (3)	C2—C7	1.390 (3)
N1—H1A	0.90 (3)	C2—C3	1.384 (3)
N1—H1B	0.93 (3)	C3—C4	1.376 (3)
C8—C9	1.373 (4)	C4—C5	1.382 (3)
C9—C10	1.381 (4)	C5—C6	1.386 (3)
C10—C13	1.509 (4)	C6—C7	1.366 (3)
C10—C11	1.362 (3)	C3—H3A	0.9300
C11—C12	1.369 (3)	C4—H4A	0.9300
C13—C13ⁱ	1.436 (4)	C6—H6A	0.9300
C8—H8A	0.9300	C7—H7A	0.9300
C9—H9A	0.9300

O1···N1ⁱⁱ	3.081 (3)	C12···H4A^xi	3.0000
O1···N1ⁱⁱⁱ	3.030 (3)	C13···H9Aⁱ	2.7900
O2···N2^iv	2.613 (2)	H1A···O1^vii	2.14 (3)
O1···H1Aⁱⁱⁱ	2.14 (3)	H1A···H4A	2.3000
O1···H1Bⁱⁱ	2.16 (3)	H1B···H6A	2.3200
O1···H7A	2.5700	H1B···O1^viii	2.16 (3)
O1···H11A	2.9200	H1B···C1^viii	2.81 (3)
O1···H4Aⁱⁱⁱ	2.8000	H2A···C8^iv	2.6900
O2···H3A	2.4500	H2A···C12^iv	2.6200
O2···H8A^v	2.7400	H2A···N2^iv	1.7200
O2···H13B^vi	2.8400	H3A···O2	2.4500
N1···O1^vii	3.030 (3)	H3A···C11^xii	3.0600
N1···O1^viii	3.081 (3)	H4A···H1A	2.3000
N2···O2^ix	2.613 (2)	H4A···C12^xii	3.0000
N2···C1^ix	3.368 (3)	H4A···O1^vii	2.8000
N1···H6A^x	2.9500	H6A···H1B	2.3200
N2···H2A^ix	1.7200	H6A···N1^xiii	2.9500
C1···N2^iv	3.368 (3)	H6A···C4^xiii	2.8700
C3···C9^v	3.567 (3)	H6A···C5^xiii	2.8100
C8···C9^v	3.587 (4)	H7A···O1	2.5700
C9···C8^v	3.587 (4)	H8A···O2^v	2.7400
C9···C3^v	3.567 (3)	H9A···C4^v	2.8700
C1···H1Bⁱⁱ	2.81 (3)	H9A···C13ⁱ	2.7900
C3···H9A^v	2.8600	H9A···C3^v	2.8600
C4···H9A^v	2.8700	H9A···H13Aⁱ	2.2400
C4···H6A^x	2.8700	H11A···O1	2.9200
C5···H6A^x	2.8100	H11A···H13A	2.3500
C7···H12A	3.0300	H12A···C7	3.0300
C8···H2A^ix	2.6900	H13A···H11A	2.3500
C9···H13Aⁱ	2.7500	H13A···C9ⁱ	2.7500
C11···H3A^xi	3.0600	H13A···H9Aⁱ	2.2400
C12···H2A^ix	2.6200	H13B···O2^vi	2.8400

C1—O2—H2A	110.00	C13ⁱ—C13—H13A	108.00
C8—N2—C12	117.08 (19)	C13ⁱ—C13—H13B	108.00
C5—N1—H1A	111 (2)	O2—C1—C2	114.69 (17)
C5—N1—H1B	113.1 (14)	O1—C1—O2	122.1 (2)
H1A—N1—H1B	128 (2)	O1—C1—C2	123.22 (19)
N2—C8—C9	122.9 (2)	C1—C2—C7	120.41 (16)
C8—C9—C10	119.9 (2)	C3—C2—C7	117.52 (19)
C9—C10—C11	116.5 (2)	C1—C2—C3	122.07 (19)
C11—C10—C13	121.1 (2)	C2—C3—C4	121.4 (2)
C9—C10—C13	122.4 (2)	C3—C4—C5	120.6 (2)
C10—C11—C12	120.2 (2)	N1—C5—C4	120.6 (2)
N2—C12—C11	123.3 (2)	C4—C5—C6	118.1 (2)
C10—C13—C13ⁱ	117.1 (2)	N1—C5—C6	121.3 (2)
C9—C8—H8A	118.00	C5—C6—C7	121.1 (2)
N2—C8—H8A	119.00	C2—C7—C6	121.17 (19)
C8—C9—H9A	120.00	C2—C3—H3A	119.00
C10—C9—H9A	120.00	C4—C3—H3A	119.00
C10—C11—H11A	120.00	C3—C4—H4A	120.00
C12—C11—H11A	120.00	C5—C4—H4A	120.00
N2—C12—H12A	118.00	C5—C6—H6A	119.00
C11—C12—H12A	118.00	C7—C6—H6A	119.00
C10—C13—H13B	108.00	C2—C7—H7A	119.00
H13A—C13—H13B	107.00	C6—C7—H7A	119.00
C10—C13—H13A	108.00

C12—N2—C8—C9	0.3 (3)	O2—C1—C2—C3	7.6 (3)
C8—N2—C12—C11	0.0 (3)	O2—C1—C2—C7	−172.38 (19)
N2—C8—C9—C10	−0.2 (4)	C1—C2—C3—C4	−177.7 (2)
C8—C9—C10—C11	−0.3 (4)	C7—C2—C3—C4	2.3 (3)
C8—C9—C10—C13	179.6 (2)	C1—C2—C7—C6	177.6 (2)
C9—C10—C11—C12	0.6 (3)	C3—C2—C7—C6	−2.3 (3)
C13—C10—C11—C12	−179.3 (2)	C2—C3—C4—C5	−0.5 (3)
C9—C10—C13—C13ⁱ	40.3 (4)	C3—C4—C5—N1	178.0 (2)
C11—C10—C13—C13ⁱ	−139.9 (3)	C3—C4—C5—C6	−1.2 (3)
C10—C11—C12—N2	−0.4 (3)	N1—C5—C6—C7	−178.0 (2)
C10—C13—C13ⁱ—C10ⁱ	−180.0 (2)	C4—C5—C6—C7	1.2 (3)
O1—C1—C2—C3	−173.5 (2)	C5—C6—C7—C2	0.6 (3)
O1—C1—C2—C7	6.5 (3)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, −y+1/2, z−1/2; (iii) x−1, y, z−1; (iv) x−1, y, z; (v) −x+2, −y+1, −z+1; (vi) −x+1, −y+1, −z+1; (vii) x+1, y, z+1; (viii) x+1, −y+1/2, z+1/2; (ix) x+1, y, z; (x) x, −y+1/2, z+1/2; (xi) x, y, z−1; (xii) x, y, z+1; (xiii) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^vii	0.90 (3)	2.14 (3)	3.030 (3)	171 (3)
N1—H1B···O1^viii	0.93 (3)	2.16 (3)	3.081 (3)	172 (2)
O2—H2A···N2^iv	0.90	1.72	2.613 (2)	173

Symmetry codes: (iv) x−1, y, z; (vii) x+1, y, z+1; (viii) x+1, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₂N₂·2C₇H₇NO₂
M_r	458.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	297
a, b, c (Å)	7.3556 (10), 23.230 (3), 7.9373 (11)
β (°)	115.579 (2)
V (Å³)	1223.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.76 × 0.34 × 0.22

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SMART; Bruker, 2000)
T_min, T_max	0.674, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6871, 2406, 1530
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.165, 1.03
No. of reflections	2406
No. of parameters	162
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.23

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 1999), SHELXL97 (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top

O1—C1	1.220 (3)	N2—C8	1.321 (3)
O2—C1	1.310 (3)	N1—C5	1.377 (3)
N2—C12	1.320 (3)

C8—N2—C12	117.08 (19)	O1—C1—O2	122.1 (2)
N2—C8—C9	122.9 (2)	O1—C1—C2	123.22 (19)
N2—C12—C11	123.3 (2)	N1—C5—C4	120.6 (2)
O2—C1—C2	114.69 (17)	N1—C5—C6	121.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.90 (3)	2.14 (3)	3.030 (3)	171 (3)
N1—H1B···O1ⁱⁱ	0.93 (3)	2.16 (3)	3.081 (3)	172 (2)
O2—H2A···N2ⁱⁱⁱ	0.9000	1.7200	2.613 (2)	173.00

Symmetry codes: (i) x+1, y, z+1; (ii) x+1, −y+1/2, z+1/2; (iii) x−1, y, z.

Acknowledgements

This work was supported financially by Yuanpei University.

References

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