1,2-Di-2-pyridylethyl­ene–phenyl­succinic acid (1/1)

Huang, Q.-Z.; Shi, H.-Z.

doi:10.1107/S1600536808040245

organic compounds

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Volume 65| Part 1| January 2009| Page o182

doi:10.1107/S1600536808040245

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1,2-Di-2-pyridylethylene–phenylsuccinic acid (1/1)

Qun-Zeng Huang ^a ^* and Heng-Zhen Shi ^a

^aCollege of Chemistry and Pharmacy Engineering, Nanyang Normal University, Nanyang 473061, People's Republic of China
^*Correspondence e-mail: nysyhqz@126.com

(Received 13 November 2008; accepted 29 November 2008; online 20 December 2008)

In the title 1:1 adduct, C₁₀H₁₀O₄·C₁₂H₁₀N₂, the two components are linked by O—H⋯N hydrogen bonds to form a one-dimensional chain. The dihedral angle between the pyridine rings is 15.68 (8)° These chains are further interconnected by weak intermolecular C—H⋯O hydrogen bonds and weak C—H⋯π interactions to generate a three-dimensional network.

Related literature

For (S)- and (R,S)-phenylsuccinic acids, see: Fischer & Profir (2003a ,b ). For weak C—H⋯O hydrogen bonds, see, for example: Bhogala et al. (2005 ); Wang et al. (2008 ). For C—H⋯π interactions, see, for example: Fun & Kia (2008 ).

Experimental

Crystal data

C₁₀H₁₀O₄·C₁₂H₁₀N₂
M_r = 376.40
Triclinic, $[P \overline 1]$
a = 8.6707 (13) Å
b = 10.9714 (17) Å
c = 11.2013 (17) Å
α = 80.801 (2)°
β = 69.696 (2)°
γ = 77.663 (2)°
V = 972.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 291 (2) K
0.34 × 0.33 × 0.29 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.957, T_max = 0.975
7261 measured reflections
3605 independent reflections
2369 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.133
S = 1.03
3605 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯N1	0.82	1.88	2.699 (2)	176
O1—H1⋯N2ⁱ	0.82	1.88	2.683 (2)	165
C2—H2⋯O2ⁱⁱ	0.93	2.56	3.472 (3)	164
C11—H11⋯O3ⁱⁱⁱ	0.93	2.43	3.350 (3)	170
C3—H3⋯Cg1^iv	0.93	2.86	3.650 (4)	143
Symmetry codes: (i) x, y+1, z-1; (ii) x-1, y, z+1; (iii) x+1, y-1, z; (iv) -x, -y+1, -z+1. Cg1 is the centroid of the C15–C20 phenyl ring.

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 I, global. DOI: 10.1107/S1600536808040245/si2134sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040245/si2134Isup2.hkl

checkCIF report

Comment top

The asymmetric unit consists of the two heteromolecular components of the title compound in a (1/1) ratio (Fig.1). These molecules are linked by intermolecular O—H···N hydrogen bonds to form a one-dimensional chain (Table 1, Fig.2). The chains interact with each other via weak intermolecular C—H···O hydrogen bonds and C—H···π interactions (Tab 1). Cg1 is the centroid of the phenyl ring C15 - C20. These hydrogen bonds, albeit rather weak, link the chains into two-dimensional layers structure (Fig. 3), which are further connected by weak intermolecular C—H···π interactions to generate a three-dimensional supramolecular structure (Fig. 4).

Related literature top

For (S)- and (R,S)-phenylsuccinic acids, see: Fischer & Profir (2003a,b). For weak C—H···O hydrogen bonds, see, for example: Bhogala et al. (2005); Wang et al. (2008). For C—H···π interactions, see, for example: Fun & Kia (2008).

Experimental top

1,2-bis(2-pyridyl)ethylene (0.15 mmol), (R)-Phenylsuccinic acid (0.15 mmol), and NaOH (0.1 mmol) were added to a H₂O solution (20 ml) in a Teflonlined stainless steel reactor. The mixture was heated at 450 K for 4 d, and then slowly cooled down to room temperature. Colorless crystals of the title compound were obtained.

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. A view of the heteromolecular components of the title compound with the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the one-dimensional hydrogen-bonding pattern network.
	Fig. 3. The crystal packing of (I), showing the two-dimensional structure.
	Fig. 4. A view of the C—H···π interactions in the crystal structure of the title compound.

1,2-Di-2-pyridylethylene–phenylsuccinic acid (1/1) top

Crystal data top

C₁₀H₁₀O₄·C₁₂H₁₀N₂	Z = 2
M_r = 376.40	F(000) = 396
Triclinic, P1	D_x = 1.286 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6707 (13) Å	Cell parameters from 1614 reflections
b = 10.9714 (17) Å	θ = 2.5–26.0°
c = 11.2013 (17) Å	µ = 0.09 mm⁻¹
α = 80.801 (2)°	T = 291 K
β = 69.696 (2)°	Block, colorless
γ = 77.663 (2)°	0.34 × 0.33 × 0.29 mm
V = 972.0 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3605 independent reflections
Radiation source: fine-focus sealed tube	2369 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −10→10
T_min = 0.957, T_max = 0.975	k = −13→13
7261 measured reflections	l = −13→13

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0553P)² + 0.1924P] where P = (F_o² + 2F_c²)/3
3605 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₀H₁₀O₄·C₁₂H₁₀N₂	γ = 77.663 (2)°
M_r = 376.40	V = 972.0 (3) Å³
Triclinic, P1	Z = 2
a = 8.6707 (13) Å	Mo Kα radiation
b = 10.9714 (17) Å	µ = 0.09 mm⁻¹
c = 11.2013 (17) Å	T = 291 K
α = 80.801 (2)°	0.34 × 0.33 × 0.29 mm
β = 69.696 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3605 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2369 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.975	R_int = 0.022
7261 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.03	Δρ_max = 0.19 e Å⁻³
3605 reflections	Δρ_min = −0.20 e Å⁻³
253 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.47679 (18)	0.96437 (13)	−0.17709 (14)	0.0637 (5)
H1	0.5453	0.9815	−0.2464	0.096*
O2	0.6712 (2)	0.79683 (17)	−0.17226 (16)	0.0896 (7)
O3	0.27415 (18)	0.75636 (14)	0.27577 (13)	0.0620 (4)
O4	0.45071 (18)	0.57475 (13)	0.26650 (13)	0.0618 (4)
H4	0.3867	0.5601	0.3387	0.093*
N1	0.2501 (2)	0.51408 (15)	0.50443 (15)	0.0485 (4)
N2	0.66326 (19)	0.01005 (14)	0.57849 (15)	0.0454 (4)
C1	0.1106 (3)	0.5966 (2)	0.5536 (2)	0.0546 (6)
H1A	0.0995	0.6764	0.5110	0.065*
C2	−0.0168 (3)	0.5695 (2)	0.6635 (2)	0.0567 (6)
H2	−0.1108	0.6295	0.6947	0.068*
C3	−0.0007 (3)	0.4507 (2)	0.7260 (2)	0.0561 (6)
H3	−0.0845	0.4289	0.7999	0.067*
C4	0.1410 (3)	0.3649 (2)	0.6774 (2)	0.0531 (5)
H4A	0.1531	0.2846	0.7187	0.064*
C5	0.2663 (2)	0.39814 (18)	0.56644 (18)	0.0434 (5)
C6	0.4216 (3)	0.31193 (19)	0.5089 (2)	0.0503 (5)
H6	0.4894	0.3386	0.4284	0.060*
C7	0.4745 (2)	0.20028 (18)	0.56004 (19)	0.0470 (5)
H7	0.4071	0.1742	0.6409	0.056*
C8	0.6279 (2)	0.11358 (18)	0.50279 (18)	0.0440 (5)
C9	0.7339 (3)	0.1334 (2)	0.3775 (2)	0.0657 (7)
H9	0.7090	0.2046	0.3256	0.079*
C10	0.8761 (3)	0.0464 (2)	0.3313 (2)	0.0720 (7)
H10	0.9480	0.0595	0.2485	0.086*
C11	0.9108 (3)	−0.0587 (2)	0.4075 (2)	0.0624 (6)
H11	1.0050	−0.1187	0.3775	0.075*
C12	0.8017 (3)	−0.07322 (19)	0.5304 (2)	0.0549 (6)
H12	0.8252	−0.1445	0.5827	0.066*
C13	0.5369 (2)	0.85814 (19)	−0.12306 (19)	0.0462 (5)
C14	0.4165 (2)	0.81888 (18)	0.00741 (18)	0.0427 (5)
H14	0.3682	0.8931	0.0550	0.051*
C15	0.2750 (2)	0.77139 (17)	−0.01329 (17)	0.0399 (5)
C16	0.1120 (2)	0.83595 (19)	0.02700 (19)	0.0488 (5)
H16	0.0881	0.9074	0.0694	0.059*
C17	−0.0154 (3)	0.7948 (2)	0.0046 (2)	0.0588 (6)
H17	−0.1236	0.8394	0.0316	0.071*
C18	0.0169 (3)	0.6883 (2)	−0.0573 (2)	0.0635 (6)
H18	−0.0688	0.6612	−0.0723	0.076*
C19	0.1789 (3)	0.6220 (2)	−0.0970 (2)	0.0603 (6)
H19	0.2018	0.5498	−0.1381	0.072*
C20	0.3064 (3)	0.66335 (19)	−0.07542 (19)	0.0497 (5)
H20	0.4145	0.6186	−0.1026	0.060*
C21	0.5086 (2)	0.7212 (2)	0.08432 (18)	0.0501 (5)
H21A	0.5541	0.6462	0.0396	0.060*
H21B	0.6013	0.7538	0.0899	0.060*
C22	0.3968 (2)	0.68718 (19)	0.21791 (18)	0.0438 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0595 (9)	0.0537 (9)	0.0538 (9)	−0.0004 (7)	−0.0032 (7)	0.0158 (7)
O2	0.0579 (10)	0.0906 (13)	0.0669 (11)	0.0189 (9)	0.0120 (9)	0.0282 (9)
O3	0.0591 (9)	0.0598 (10)	0.0442 (8)	0.0097 (8)	−0.0023 (7)	0.0005 (7)
O4	0.0653 (10)	0.0513 (9)	0.0446 (8)	0.0079 (7)	−0.0029 (7)	0.0062 (7)
N1	0.0520 (10)	0.0422 (10)	0.0428 (9)	−0.0012 (8)	−0.0126 (8)	0.0046 (8)
N2	0.0471 (9)	0.0384 (9)	0.0450 (9)	−0.0050 (7)	−0.0134 (8)	0.0056 (7)
C1	0.0621 (14)	0.0425 (12)	0.0498 (13)	0.0039 (10)	−0.0165 (11)	0.0013 (10)
C2	0.0534 (13)	0.0584 (14)	0.0490 (13)	0.0073 (11)	−0.0135 (10)	−0.0080 (11)
C3	0.0525 (13)	0.0640 (15)	0.0420 (12)	−0.0079 (11)	−0.0068 (10)	0.0006 (11)
C4	0.0551 (13)	0.0464 (12)	0.0479 (12)	−0.0053 (10)	−0.0107 (10)	0.0051 (10)
C5	0.0458 (11)	0.0419 (11)	0.0398 (11)	−0.0055 (9)	−0.0141 (9)	0.0012 (9)
C6	0.0508 (12)	0.0475 (12)	0.0425 (11)	−0.0031 (10)	−0.0098 (9)	0.0052 (9)
C7	0.0514 (12)	0.0457 (12)	0.0387 (11)	−0.0053 (9)	−0.0122 (9)	0.0011 (9)
C8	0.0495 (11)	0.0413 (11)	0.0397 (11)	−0.0062 (9)	−0.0150 (9)	−0.0005 (9)
C9	0.0788 (16)	0.0581 (15)	0.0403 (12)	0.0049 (12)	−0.0092 (11)	0.0063 (11)
C10	0.0762 (17)	0.0708 (17)	0.0427 (13)	0.0047 (13)	0.0013 (12)	−0.0010 (12)
C11	0.0553 (13)	0.0549 (14)	0.0608 (14)	0.0042 (11)	−0.0055 (11)	−0.0083 (12)
C12	0.0521 (12)	0.0431 (12)	0.0600 (14)	−0.0005 (10)	−0.0148 (11)	0.0038 (10)
C13	0.0405 (11)	0.0446 (12)	0.0451 (11)	−0.0064 (9)	−0.0083 (9)	0.0060 (9)
C14	0.0421 (10)	0.0409 (11)	0.0375 (10)	−0.0041 (8)	−0.0072 (8)	0.0005 (8)
C15	0.0393 (10)	0.0417 (11)	0.0325 (10)	−0.0047 (8)	−0.0081 (8)	0.0034 (8)
C16	0.0436 (11)	0.0463 (12)	0.0477 (12)	−0.0027 (9)	−0.0091 (9)	0.0012 (9)
C17	0.0378 (11)	0.0715 (16)	0.0586 (14)	−0.0083 (11)	−0.0134 (10)	0.0115 (12)
C18	0.0639 (15)	0.0765 (17)	0.0579 (14)	−0.0299 (13)	−0.0258 (12)	0.0094 (13)
C19	0.0706 (16)	0.0599 (14)	0.0529 (13)	−0.0190 (12)	−0.0183 (12)	−0.0052 (11)
C20	0.0473 (12)	0.0501 (13)	0.0457 (12)	−0.0033 (10)	−0.0113 (9)	−0.0025 (10)
C21	0.0409 (11)	0.0568 (13)	0.0450 (12)	−0.0067 (9)	−0.0094 (9)	0.0039 (10)
C22	0.0433 (11)	0.0477 (12)	0.0370 (10)	−0.0047 (9)	−0.0117 (9)	−0.0018 (9)

Geometric parameters (Å, º) top

O1—C13	1.315 (2)	C9—H9	0.9300
O1—H1	0.8200	C10—C11	1.365 (3)
O2—C13	1.204 (2)	C10—H10	0.9300
O3—C22	1.209 (2)	C11—C12	1.380 (3)
O4—C22	1.324 (2)	C11—H11	0.9300
O4—H4	0.8200	C12—H12	0.9300
N1—C1	1.347 (2)	C13—C14	1.531 (3)
N1—C5	1.352 (2)	C14—C15	1.529 (3)
N2—C12	1.344 (2)	C14—C21	1.532 (3)
N2—C8	1.352 (2)	C14—H14	0.9800
C1—C2	1.380 (3)	C15—C16	1.391 (3)
C1—H1A	0.9300	C15—C20	1.399 (3)
C2—C3	1.381 (3)	C16—C17	1.389 (3)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.378 (3)	C17—C18	1.383 (3)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.395 (3)	C18—C19	1.390 (3)
C4—H4A	0.9300	C18—H18	0.9300
C5—C6	1.474 (3)	C19—C20	1.387 (3)
C6—C7	1.326 (3)	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.465 (3)	C21—C22	1.513 (3)
C7—H7	0.9300	C21—H21A	0.9700
C8—C9	1.398 (3)	C21—H21B	0.9700
C9—C10	1.382 (3)

C13—O1—H1	109.5	N2—C12—H12	118.2
C22—O4—H4	109.5	C11—C12—H12	118.2
C1—N1—C5	118.17 (17)	O2—C13—O1	123.53 (18)
C12—N2—C8	118.53 (17)	O2—C13—C14	123.50 (18)
N1—C1—C2	123.70 (19)	O1—C13—C14	112.95 (16)
N1—C1—H1A	118.1	C15—C14—C13	108.73 (16)
C2—C1—H1A	118.1	C15—C14—C21	112.41 (16)
C1—C2—C3	118.01 (19)	C13—C14—C21	110.86 (15)
C1—C2—H2	121.0	C15—C14—H14	108.2
C3—C2—H2	121.0	C13—C14—H14	108.2
C4—C3—C2	119.24 (19)	C21—C14—H14	108.2
C4—C3—H3	120.4	C16—C15—C20	118.20 (19)
C2—C3—H3	120.4	C16—C15—C14	120.81 (18)
C3—C4—C5	120.13 (19)	C20—C15—C14	120.98 (17)
C3—C4—H4A	119.9	C17—C16—C15	120.7 (2)
C5—C4—H4A	119.9	C17—C16—H16	119.6
N1—C5—C4	120.74 (17)	C15—C16—H16	119.6
N1—C5—C6	115.87 (17)	C18—C17—C16	120.7 (2)
C4—C5—C6	123.39 (18)	C18—C17—H17	119.7
C7—C6—C5	126.66 (19)	C16—C17—H17	119.7
C7—C6—H6	116.7	C17—C18—C19	119.3 (2)
C5—C6—H6	116.7	C17—C18—H18	120.4
C6—C7—C8	126.93 (19)	C19—C18—H18	120.4
C6—C7—H7	116.5	C20—C19—C18	120.1 (2)
C8—C7—H7	116.5	C20—C19—H19	120.0
N2—C8—C9	120.45 (18)	C18—C19—H19	120.0
N2—C8—C7	116.06 (17)	C19—C20—C15	121.01 (19)
C9—C8—C7	123.49 (18)	C19—C20—H20	119.5
C10—C9—C8	119.6 (2)	C15—C20—H20	119.5
C10—C9—H9	120.2	C22—C21—C14	112.58 (16)
C8—C9—H9	120.2	C22—C21—H21A	109.1
C11—C10—C9	119.9 (2)	C14—C21—H21A	109.1
C11—C10—H10	120.0	C22—C21—H21B	109.1
C9—C10—H10	120.0	C14—C21—H21B	109.1
C10—C11—C12	118.0 (2)	H21A—C21—H21B	107.8
C10—C11—H11	121.0	O3—C22—O4	123.46 (18)
C12—C11—H11	121.0	O3—C22—C21	123.82 (18)
N2—C12—C11	123.6 (2)	O4—C22—C21	112.68 (16)

C5—N1—C1—C2	−0.1 (3)	O2—C13—C14—C15	−104.5 (2)
N1—C1—C2—C3	−0.5 (3)	O1—C13—C14—C15	74.0 (2)
C1—C2—C3—C4	0.6 (3)	O2—C13—C14—C21	19.5 (3)
C2—C3—C4—C5	0.0 (3)	O1—C13—C14—C21	−161.95 (18)
C1—N1—C5—C4	0.7 (3)	C13—C14—C15—C16	−114.07 (19)
C1—N1—C5—C6	−179.70 (18)	C21—C14—C15—C16	122.80 (19)
C3—C4—C5—N1	−0.6 (3)	C13—C14—C15—C20	64.7 (2)
C3—C4—C5—C6	179.8 (2)	C21—C14—C15—C20	−58.5 (2)
N1—C5—C6—C7	171.0 (2)	C20—C15—C16—C17	−0.8 (3)
C4—C5—C6—C7	−9.4 (3)	C14—C15—C16—C17	178.00 (17)
C5—C6—C7—C8	179.33 (19)	C15—C16—C17—C18	0.5 (3)
C12—N2—C8—C9	−0.3 (3)	C16—C17—C18—C19	0.2 (3)
C12—N2—C8—C7	179.38 (18)	C17—C18—C19—C20	−0.5 (3)
C6—C7—C8—N2	173.9 (2)	C18—C19—C20—C15	0.3 (3)
C6—C7—C8—C9	−6.4 (4)	C16—C15—C20—C19	0.4 (3)
N2—C8—C9—C10	−0.2 (3)	C14—C15—C20—C19	−178.39 (18)
C7—C8—C9—C10	−179.9 (2)	C15—C14—C21—C22	−62.5 (2)
C8—C9—C10—C11	0.9 (4)	C13—C14—C21—C22	175.58 (17)
C9—C10—C11—C12	−0.9 (4)	C14—C21—C22—O3	−26.4 (3)
C8—N2—C12—C11	0.3 (3)	C14—C21—C22—O4	155.70 (18)
C10—C11—C12—N2	0.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N1	0.82	1.88	2.699 (2)	176
O1—H1···N2ⁱ	0.82	1.88	2.683 (2)	165
C2—H2···O2ⁱⁱ	0.93	2.56	3.472 (3)	164
C11—H11···O3ⁱⁱⁱ	0.93	2.43	3.350 (3)	170
C3—H3···Cg1^iv	0.93	2.86	3.650 (4)	143

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀O₄·C₁₂H₁₀N₂
M_r	376.40
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	8.6707 (13), 10.9714 (17), 11.2013 (17)
α, β, γ (°)	80.801 (2), 69.696 (2), 77.663 (2)
V (Å³)	972.0 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.34 × 0.33 × 0.29

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.957, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	7261, 3605, 2369
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.133, 1.03
No. of reflections	3605
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

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
O4—H4···N1	0.82	1.88	2.699 (2)	176
O1—H1···N2ⁱ	0.82	1.88	2.683 (2)	165
C2—H2···O2ⁱⁱ	0.93	2.56	3.472 (3)	164
C11—H11···O3ⁱⁱⁱ	0.93	2.43	3.350 (3)	170
C3—H3···Cg1^iv	0.93	2.86	3.650 (4)	143

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

Acknowledgements

The authors thank Nanyang Normal University for supporting this work.

References

Bhogala, B. R., Basavoju, S. & Nangia, A. (2005). Cryst. Growth Des. 5, 1683–1686. Web of Science CSD CrossRef CAS Google Scholar
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