4-Amino-3-methyl­benzoic acid–1,2-bis­(4-pyrid­yl)ethane (1/1)

Lush, S.F.; Chen, C.W.; Yang, C.; Shen, F.M.

doi:10.1107/S1600536811005381

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o652

doi:10.1107/S1600536811005381

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4-Amino-3-methylbenzoic acid–1,2-bis(4-pyridyl)ethane (1/1)

Shie Fu Lush,^a Chong Wei Chen,^b Chieh Yang ^b and Fwu Ming Shen ^c ^*

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

(Received 2 February 2011; accepted 14 February 2011; online 19 February 2011)

In the crystal structure of the title 1:1 adduct, C₁₂H₁₂N₂·C₈H₉NO₂, the 4-amino-3-methylbenzoic acid molecules and 1,2-bis(4-pyridyl)ethane molecules are linked by intermolecular O—H⋯N, N—H⋯O and N—H⋯N hydrogen bonds, forming a two-dimensional supramolecular network parallel to (001). In the 1,2-bis(4-pyridyl)ethane molecule, the two pyridine rings are twisted to each other by a dihedral angle of 12.12 (8)°. The non-H atoms of the 4-amino-3-methylbenzoic acid molecule are almost coplanar, the maximum atomic deviation being 0.029 (1) Å. Weak C—H⋯π interactions are present in the crystal structure.

Related literature

For related structures, see: Bowes et al. (2003 ); Ferguson et al. (1999 ); Shen & Lush (2010 ). For hydrogen-bond motifs, see: Etter et al. (1990 ).

Experimental

Crystal data

C₁₂H₁₂N₂·C₈H₉NO₂
M_r = 335.40
Monoclinic, P 2₁ /c
a = 8.0695 (3) Å
b = 13.0677 (5) Å
c = 17.6138 (10) Å
β = 99.501 (5)°
V = 1831.89 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 297 K
0.60 × 0.18 × 0.12 mm

Data collection

Oxford Diffraction Gemini-S CCD diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.919, T_max = 1.000
8821 measured reflections
4277 independent reflections
1870 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.082
S = 1.03
4277 reflections
232 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N2	0.821 (9)	1.826 (11)	2.6407 (18)	171.6 (15)
N1—H1B⋯O2ⁱ	0.860 (11)	2.113 (12)	2.951 (2)	164.5 (14)
N1—H1C⋯N3ⁱⁱ	0.860 (7)	2.288 (9)	3.084 (2)	153.8 (14)
C12—H12A⋯Cgⁱⁱⁱ	0.93	2.76	3.540 (2)	141
Symmetry codes: (i) x-1, y, z; (ii) x-2, y+1, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005381/xu5156sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005381/xu5156Isup2.hkl

checkCIF report

Comment top

The 1,2-bis(4-pyridyl)ethane is a versatile building block for the purposes of crystal engineering. Each of the pyridyl N atoms acts as a hydrogen bond acceptor, forming linear hydrogen associations (Ferguson et al., 1999). Other structures related with 1,2-bis(4-pyridyl)ethane and Lewis acid were reported by Bowes et al. (2003) and Shen & Lush (2010). We present here the crystal structure of the 4-amino-3-methybenzoic acid and 1,2-bis(4-pyridyl)ethane 1:1 adduct.

The structure of the title compound comprises 4-amino-3-methybenzoic acid molecule and 1,2-bis(4-pyridyl)ethane molecule, with no proton transfer. In the structure, the molecules associate 4-amino-3-methybenzoic acid and 1,2-bis(4-pyridyl)ethane via carboxylic and pyridine group O—H···N [O···N 2.640 (18) Å] C²₂(19) (Etter et al., 1990), forming linear hydrogen bonding parallel to [0 0 1], further connect a two dimensional network via amine and carboxylic N—H···O and N—H···N [2.951 (2) and 3.084 (2) Å], respectively. Furthermore, C—H···π ring stacking interaction is present in the structure. The distance between C12—H(12 A)···Cg3 ⁱⁱⁱ(C2—C7) is 3.540 (2) Å [symmetry code: (iii) = 1-X,-1/2+Y,3/2-Z].

Related literature top

For related structures, see: Bowes et al. (2003); Ferguson et al. (1999); Shen & Lush (2010). For hydrogen-bond motifs, see: Etter et al. (1990).

Experimental top

The 4-amino-3-methybenzoic acid (151 mg, 1 mmol) and 1,2-bis(4-pyridyl)ethane (184 mg, 1 mmol) were dissolved in 20 ml methanol, the solution was refluxed for 30 min. The filtered solution was transferred to a 25 ml tube, at room temperature colorless crystals were formed after several days (yield 59.12%).

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: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. The molecular packing for the title compound. Hydrogen bonds are shown as dashed lines.

4-Amino-3-methylbenzoic acid–1,2-bis(4-pyridyl)ethane (1/1) top

Crystal data top

C₁₂H₁₂N₂·C₈H₉NO₂	F(000) = 712
M_r = 335.40	D_x = 1.216 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2506 reflections
a = 8.0695 (3) Å	θ = 3.0–29.0°
b = 13.0677 (5) Å	µ = 0.08 mm⁻¹
c = 17.6138 (10) Å	T = 297 K
β = 99.501 (5)°	Parallelepiped, colorless
V = 1831.89 (15) Å³	0.60 × 0.18 × 0.12 mm
Z = 4

Data collection top

Oxford Diffraction Gemini-S CCD diffractometer	4277 independent reflections
Radiation source: fine-focus sealed tube	1870 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 29.1°, θ_min = 3.0°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −10→10
T_min = 0.919, T_max = 1.000	k = −17→16
8821 measured reflections	l = −24→20

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.025P)²] where P = (F_o² + 2F_c²)/3
4277 reflections	(Δ/σ)_max < 0.001
232 parameters	Δρ_max = 0.15 e Å⁻³
3 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₂H₁₂N₂·C₈H₉NO₂	V = 1831.89 (15) Å³
M_r = 335.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.0695 (3) Å	µ = 0.08 mm⁻¹
b = 13.0677 (5) Å	T = 297 K
c = 17.6138 (10) Å	0.60 × 0.18 × 0.12 mm
β = 99.501 (5)°

Data collection top

Oxford Diffraction Gemini-S CCD diffractometer	4277 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1870 reflections with I > 2σ(I)
T_min = 0.919, T_max = 1.000	R_int = 0.025
8821 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	3 restraints
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.15 e Å⁻³
4277 reflections	Δρ_min = −0.22 e Å⁻³
232 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 e.s.d.'s 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	0.63037 (17)	0.47008 (10)	0.62737 (9)	0.0552 (6)
N3	1.58754 (19)	0.08351 (11)	0.60868 (10)	0.0692 (7)
C9	0.7078 (2)	0.47692 (12)	0.56699 (11)	0.0553 (7)
C10	0.8385 (2)	0.41502 (12)	0.55562 (10)	0.0521 (7)
C11	0.8957 (2)	0.34059 (12)	0.60903 (11)	0.0482 (7)
C12	0.8172 (2)	0.33448 (13)	0.67191 (11)	0.0650 (8)
C13	0.6872 (2)	0.39953 (15)	0.67901 (11)	0.0683 (8)
C14	1.0359 (2)	0.26912 (12)	0.59857 (12)	0.0705 (8)
C15	1.2064 (2)	0.30811 (12)	0.62896 (11)	0.0660 (7)
C16	1.3425 (2)	0.23093 (12)	0.62204 (11)	0.0506 (7)
C17	1.4071 (2)	0.16866 (14)	0.68217 (11)	0.0639 (8)
C18	1.5274 (2)	0.09729 (14)	0.67281 (12)	0.0710 (8)
C19	1.5251 (2)	0.14425 (15)	0.55151 (12)	0.0808 (9)
C20	1.4039 (2)	0.21762 (13)	0.55528 (11)	0.0686 (8)
O1	0.34436 (14)	0.56570 (8)	0.63298 (7)	0.0542 (5)
O2	0.47629 (14)	0.71109 (8)	0.61635 (7)	0.0664 (5)
N1	−0.25914 (19)	0.86901 (13)	0.64324 (10)	0.0628 (7)
C1	0.34970 (19)	0.66628 (12)	0.62564 (9)	0.0399 (4)
C2	0.18870 (19)	0.71739 (11)	0.63001 (9)	0.0399 (4)
C3	0.04752 (18)	0.66405 (11)	0.64278 (9)	0.0427 (6)
C4	−0.09994 (19)	0.71458 (11)	0.64585 (9)	0.0451 (6)
C5	−0.11212 (19)	0.82069 (12)	0.63671 (9)	0.0421 (6)
C6	0.0301 (2)	0.87564 (11)	0.62414 (9)	0.0465 (6)
C7	0.17592 (19)	0.82300 (11)	0.62061 (9)	0.0461 (6)
C8	0.0217 (2)	0.99081 (11)	0.61582 (12)	0.0818 (9)
H9A	0.67140	0.52660	0.53020	0.0660*
H10A	0.88840	0.42320	0.51200	0.0620*
H12A	0.85190	0.28610	0.71000	0.0780*
H13A	0.63640	0.39370	0.72250	0.0820*
H14A	1.01960	0.20490	0.62390	0.0850*
H14B	1.02920	0.25500	0.54410	0.0850*
H15A	1.21180	0.32640	0.68270	0.0790*
H15B	1.22680	0.36960	0.60110	0.0790*
H17A	1.36980	0.17460	0.72920	0.0770*
H18A	1.56900	0.05610	0.71470	0.0850*
H19A	1.56560	0.13720	0.50530	0.0970*
H20A	1.36450	0.25770	0.51250	0.0820*
H1A	0.4380 (9)	0.5416 (12)	0.6323 (10)	0.082 (7)*
H1B	−0.3449 (12)	0.8295 (10)	0.6418 (10)	0.075 (7)*
H1C	−0.2717 (19)	0.9312 (4)	0.6273 (8)	0.055 (6)*
H3A	0.05290	0.59340	0.64930	0.0510*
H4A	−0.19370	0.67760	0.65420	0.0540*
H7A	0.26980	0.85930	0.61160	0.0550*
H8A	0.12810	1.01620	0.60650	0.1230*
H8B	−0.00420	1.02060	0.66230	0.1230*
H8C	−0.06420	1.00870	0.57340	0.1230*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0437 (9)	0.0556 (9)	0.0657 (11)	0.0178 (7)	0.0069 (9)	0.0008 (8)
N3	0.0678 (11)	0.0797 (11)	0.0613 (12)	0.0363 (9)	0.0146 (9)	0.0079 (10)
C9	0.0509 (12)	0.0498 (10)	0.0631 (14)	0.0097 (9)	0.0032 (10)	0.0069 (10)
C10	0.0460 (11)	0.0559 (11)	0.0560 (13)	0.0066 (9)	0.0135 (9)	−0.0026 (10)
C11	0.0385 (10)	0.0426 (11)	0.0617 (13)	0.0093 (8)	0.0030 (10)	−0.0118 (10)
C12	0.0609 (13)	0.0670 (12)	0.0668 (14)	0.0282 (10)	0.0097 (11)	0.0173 (11)
C13	0.0588 (13)	0.0887 (14)	0.0608 (14)	0.0230 (11)	0.0196 (10)	0.0105 (12)
C14	0.0474 (12)	0.0566 (11)	0.1053 (17)	0.0179 (10)	0.0062 (11)	−0.0171 (11)
C15	0.0442 (11)	0.0605 (11)	0.0922 (16)	0.0139 (10)	0.0082 (11)	−0.0143 (11)
C16	0.0388 (11)	0.0516 (11)	0.0611 (14)	0.0114 (9)	0.0077 (10)	−0.0091 (10)
C17	0.0597 (13)	0.0812 (13)	0.0535 (14)	0.0216 (11)	0.0173 (10)	−0.0002 (11)
C18	0.0713 (14)	0.0834 (15)	0.0572 (15)	0.0318 (11)	0.0071 (12)	0.0163 (11)
C19	0.0877 (16)	0.1022 (16)	0.0580 (15)	0.0442 (14)	0.0285 (12)	0.0109 (13)
C20	0.0699 (14)	0.0747 (13)	0.0617 (15)	0.0361 (11)	0.0127 (11)	0.0150 (11)
O1	0.0387 (8)	0.0491 (7)	0.0761 (9)	0.0153 (6)	0.0130 (7)	−0.0007 (6)
O2	0.0306 (7)	0.0689 (8)	0.1025 (10)	−0.0004 (6)	0.0192 (7)	0.0135 (7)
N1	0.0418 (10)	0.0476 (10)	0.1012 (14)	0.0112 (9)	0.0184 (10)	−0.0012 (10)
C1	0.0324 (7)	0.0430 (7)	0.0442 (7)	0.0040 (5)	0.0058 (5)	−0.0032 (6)
C2	0.0324 (7)	0.0430 (7)	0.0442 (7)	0.0040 (5)	0.0058 (5)	−0.0032 (6)
C3	0.0354 (10)	0.0332 (8)	0.0604 (12)	0.0031 (8)	0.0109 (8)	−0.0035 (8)
C4	0.0313 (10)	0.0403 (10)	0.0651 (13)	−0.0011 (8)	0.0123 (8)	−0.0038 (8)
C5	0.0316 (9)	0.0430 (10)	0.0519 (12)	0.0085 (8)	0.0072 (8)	−0.0072 (9)
C6	0.0411 (11)	0.0378 (9)	0.0606 (13)	0.0039 (9)	0.0088 (9)	−0.0002 (9)
C7	0.0354 (10)	0.0444 (10)	0.0594 (12)	−0.0042 (8)	0.0109 (9)	0.0003 (9)
C8	0.0647 (14)	0.0445 (11)	0.138 (2)	0.0047 (9)	0.0217 (13)	0.0091 (11)

Geometric parameters (Å, º) top

O1—C1	1.3221 (19)	C13—H13A	0.9300
O2—C1	1.2118 (19)	C14—H14A	0.9700
O1—H1A	0.821 (9)	C14—H14B	0.9700
N2—C13	1.323 (2)	C15—H15B	0.9700
N2—C9	1.322 (2)	C15—H15A	0.9700
N3—C18	1.313 (3)	C17—H17A	0.9300
N3—C19	1.315 (3)	C18—H18A	0.9300
N1—C5	1.366 (2)	C19—H19A	0.9300
N1—H1C	0.860 (7)	C20—H20A	0.9300
N1—H1B	0.860 (11)	C1—C2	1.474 (2)
C9—C10	1.370 (2)	C2—C3	1.385 (2)
C10—C11	1.379 (2)	C2—C7	1.392 (2)
C11—C12	1.366 (3)	C3—C4	1.370 (2)
C11—C14	1.502 (2)	C4—C5	1.398 (2)
C12—C13	1.372 (2)	C5—C6	1.402 (2)
C14—C15	1.482 (2)	C6—C7	1.373 (2)
C15—C16	1.511 (2)	C6—C8	1.513 (2)
C16—C17	1.369 (3)	C3—H3A	0.9300
C16—C20	1.360 (3)	C4—H4A	0.9300
C17—C18	1.376 (2)	C7—H7A	0.9300
C19—C20	1.379 (2)	C8—H8A	0.9600
C9—H9A	0.9300	C8—H8B	0.9600
C10—H10A	0.9300	C8—H8C	0.9600
C12—H12A	0.9300

C1—O1—H1A	109.6 (10)	H15A—C15—H15B	108.00
C9—N2—C13	116.35 (14)	C14—C15—H15A	109.00
C18—N3—C19	115.24 (16)	C16—C17—H17A	120.00
H1B—N1—H1C	120.4 (14)	C18—C17—H17A	120.00
C5—N1—H1B	115.2 (8)	N3—C18—H18A	118.00
C5—N1—H1C	117.8 (10)	C17—C18—H18A	118.00
N2—C9—C10	123.71 (16)	C20—C19—H19A	118.00
C9—C10—C11	119.73 (16)	N3—C19—H19A	118.00
C10—C11—C12	116.53 (15)	C16—C20—H20A	120.00
C10—C11—C14	121.95 (16)	C19—C20—H20A	120.00
C12—C11—C14	121.52 (16)	O2—C1—C2	123.92 (14)
C11—C12—C13	120.11 (17)	O1—C1—O2	122.37 (14)
N2—C13—C12	123.55 (17)	O1—C1—C2	113.71 (13)
C11—C14—C15	114.53 (14)	C1—C2—C7	119.45 (14)
C14—C15—C16	112.66 (14)	C3—C2—C7	118.13 (14)
C15—C16—C17	121.57 (16)	C1—C2—C3	122.42 (13)
C15—C16—C20	121.90 (16)	C2—C3—C4	120.46 (14)
C17—C16—C20	116.51 (16)	C3—C4—C5	121.25 (14)
C16—C17—C18	119.77 (17)	N1—C5—C4	119.65 (15)
N3—C18—C17	124.36 (18)	N1—C5—C6	121.45 (15)
N3—C19—C20	124.59 (18)	C4—C5—C6	118.85 (14)
C16—C20—C19	119.53 (17)	C5—C6—C8	120.01 (14)
C10—C9—H9A	118.00	C7—C6—C8	121.27 (14)
N2—C9—H9A	118.00	C5—C6—C7	118.72 (14)
C9—C10—H10A	120.00	C2—C7—C6	122.58 (14)
C11—C10—H10A	120.00	C2—C3—H3A	120.00
C11—C12—H12A	120.00	C4—C3—H3A	120.00
C13—C12—H12A	120.00	C3—C4—H4A	119.00
C12—C13—H13A	118.00	C5—C4—H4A	119.00
N2—C13—H13A	118.00	C2—C7—H7A	119.00
C11—C14—H14A	109.00	C6—C7—H7A	119.00
C11—C14—H14B	109.00	C6—C8—H8A	109.00
H14A—C14—H14B	108.00	C6—C8—H8B	109.00
C15—C14—H14A	109.00	C6—C8—H8C	109.00
C15—C14—H14B	109.00	H8A—C8—H8B	109.00
C16—C15—H15A	109.00	H8A—C8—H8C	110.00
C14—C15—H15B	109.00	H8B—C8—H8C	110.00
C16—C15—H15B	109.00

C13—N2—C9—C10	0.9 (3)	C16—C17—C18—N3	0.0 (3)
C9—N2—C13—C12	−1.0 (3)	N3—C19—C20—C16	0.6 (3)
C19—N3—C18—C17	0.4 (3)	O1—C1—C2—C3	1.7 (2)
C18—N3—C19—C20	−0.7 (3)	O1—C1—C2—C7	−177.92 (14)
N2—C9—C10—C11	0.0 (3)	O2—C1—C2—C3	−178.20 (16)
C9—C10—C11—C12	−0.9 (2)	O2—C1—C2—C7	2.2 (2)
C9—C10—C11—C14	178.60 (16)	C1—C2—C3—C4	−179.52 (15)
C10—C11—C12—C13	0.8 (3)	C7—C2—C3—C4	0.1 (2)
C14—C11—C12—C13	−178.66 (16)	C1—C2—C7—C6	−179.85 (15)
C10—C11—C14—C15	87.8 (2)	C3—C2—C7—C6	0.5 (2)
C12—C11—C14—C15	−92.8 (2)	C2—C3—C4—C5	−0.4 (2)
C11—C12—C13—N2	0.1 (3)	C3—C4—C5—N1	−177.34 (16)
C11—C14—C15—C16	176.12 (16)	C3—C4—C5—C6	0.0 (2)
C14—C15—C16—C17	−96.3 (2)	N1—C5—C6—C7	177.88 (16)
C14—C15—C16—C20	81.9 (2)	N1—C5—C6—C8	−1.3 (2)
C15—C16—C17—C18	178.08 (16)	C4—C5—C6—C7	0.6 (2)
C20—C16—C17—C18	−0.1 (2)	C4—C5—C6—C8	−178.64 (15)
C15—C16—C20—C19	−178.34 (16)	C5—C6—C7—C2	−0.9 (2)
C17—C16—C20—C19	−0.1 (2)	C8—C6—C7—C2	178.32 (16)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2	0.821 (9)	1.826 (11)	2.6407 (18)	171.6 (15)
N1—H1B···O2ⁱ	0.860 (11)	2.113 (12)	2.951 (2)	164.5 (14)
N1—H1C···N3ⁱⁱ	0.860 (7)	2.288 (9)	3.084 (2)	153.8 (14)
C12—H12A···Cgⁱⁱⁱ	0.93	2.76	3.540 (2)	141

Symmetry codes: (i) x−1, y, z; (ii) x−2, y+1, z; (iii) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₂N₂·C₈H₉NO₂
M_r	335.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	297
a, b, c (Å)	8.0695 (3), 13.0677 (5), 17.6138 (10)
β (°)	99.501 (5)
V (Å³)	1831.89 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.60 × 0.18 × 0.12

Data collection
Diffractometer	Oxford Diffraction Gemini-S CCD diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.919, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8821, 4277, 1870
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.683

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.082, 1.03
No. of reflections	4277
No. of parameters	232
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.22

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2	0.821 (9)	1.826 (11)	2.6407 (18)	171.6 (15)
N1—H1B···O2ⁱ	0.860 (11)	2.113 (12)	2.951 (2)	164.5 (14)
N1—H1C···N3ⁱⁱ	0.860 (7)	2.288 (9)	3.084 (2)	153.8 (14)
C12—H12A···Cgⁱⁱⁱ	0.93	2.76	3.540 (2)	141

Symmetry codes: (i) x−1, y, z; (ii) x−2, y+1, z; (iii) −x+1, y−1/2, −z+3/2.

Acknowledgements

This work was supported financially by Yuanpei University, Taiwan.

References

Bowes, K. F., Ferguson, G., Lough, A. J. & Glidewell, C. (2003). Acta Cryst. B59, 100–117. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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