(E)-4-(4-Methyl­styr­yl)pyridine–(E)-but-2-enedioic acid (2/1)

Bu, T.-J.; Li, B.; Wu, L.-X.

doi:10.1107/S1600536807033260

(E)-4-(4-Methylstyryl)pyridine–(E)-but-2-enedioic acid (2/1)

In the title compound, 2C₁₄H₁₃N·C₄H₄O₂, the asymmetric unit consists of two crystallographically independent (E)-4-(4-methylstyryl)pyridine and one (E)-but-2-enedioic acid molecules, which are linked through O—H

N hydrogen bonds to form a linear arrangement.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033260/dn2213sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033260/dn2213Isup2.hkl Contains datablock I

CCDC reference: 657741

checkCIF report

Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.005 Å
R factor = 0.052
wR factor = 0.141
Data-to-parameter ratio = 8.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         84 PerFi

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C8     -   C14     ..       6.08 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.38
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C14 H13 N

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.48
           From the CIF: _reflns_number_total               3033
           Count of symmetry unique reflns         3042
           Completeness (_total/calc)             99.70%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

(E)-4-(4-methylstyryl)pyridine and its ramifications have attracted extensive attention because of their photophysical, photochemical and electrochemical properties (Chung et al., 1991; Yam et al., 1998). They are also be used widely for building up supramolecular networks through covalent bonds with metals (Ayyappan et al., 2004; Lin et al., 2000). We report here the crystal structure of the title compound, (I).

The asymmetric unit of (I) contains two independent (E)-4-(4-methylstyryl)pyridine and one (E)-but-2-enedioic acid molecules and they are linked by stong O - H ··· N hydrogen bonds into a linear arrangement (Fig.1). The three molecules are all nearly planar and the diheral angles of (E)-but-2-enedioic acid molecule and two (E)-4-(4-methylstyryl)pyridine molecules are 4.86 (5)° and 16.51 (7)°, respectively.

Related literature top

For general background, see: Chung et al. (1991); Yam et al. (1998). For related structures, see: Ayyappan et al. (2004); Lin et al. (2000).

Experimental top

A mixture of 4-methylpyridine (0.93 g, 10 mmol)and 4-methylbenzaldehyde (0.96 g, 10 mmol) in Acetic anhydride (50 ml) was heated to 413 K for 6 h. After cooling, filtration and drying, (E)-4-(4-methylstyryl)pyridine was obtained. (E)-but-2-enedioic acid was used as purchased without further purification. (E)-4-(4-methylstyryl)pyridine (0.39 g, 2 mmol) and (E)-but-2-enedioic acid (0.12 g, 1 mmol) were dissolved in DMF (30 ml), the mixture was stirred for 2 h at room temperature. The filtrate was stand at room temperature for two months, colorless crystals suitable for single-crystal X-ray measurement were obtained

Structure description top

For general background, see: Chung et al. (1991); Yam et al. (1998). For related structures, see: Ayyappan et al. (2004); Lin et al. (2000).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The asymmetric unit of (I), with the atom- numbering scheme. Displacement ellipsoids of non-H atoms are drawn at the 30% probalility level. O - H ··· N hydrogen bonds are indicated by dashed lines. H atoms are represented as small spheres of arbitrary radii.

(E)-4-(4-Methylstyryl)pyridine–(E)-but-2-enedioic acid (2/1) top

Crystal data top

2C₁₄H₁₃N·C₄H₄O₄	F(000) = 1072
M_r = 506.58	D_x = 1.268 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 9893 reflections
a = 21.952 (1) Å	θ = 3.8–54.9°
b = 7.3477 (3) Å	µ = 0.08 mm⁻¹
c = 17.0000 (7) Å	T = 291 K
β = 104.610 (2)°	Block, colourless
V = 2653.4 (2) Å³	0.25 × 0.24 × 0.23 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	3033 independent reflections
Radiation source: fine-focus sealed tube	2450 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −28→28
T_min = 0.979, T_max = 0.981	k = −9→9
12115 measured reflections	l = −22→21

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1053P)²] where P = (F_o² + 2F_c²)/3
3033 reflections	(Δ/σ)_max = 0.024
347 parameters	Δρ_max = 0.34 e Å⁻³
2 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

2C₁₄H₁₃N·C₄H₄O₄	V = 2653.4 (2) Å³
M_r = 506.58	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 21.952 (1) Å	µ = 0.08 mm⁻¹
b = 7.3477 (3) Å	T = 291 K
c = 17.0000 (7) Å	0.25 × 0.24 × 0.23 mm
β = 104.610 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3033 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2450 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.981	R_int = 0.026
12115 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	2 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.00	Δρ_max = 0.34 e Å⁻³
3033 reflections	Δρ_min = −0.38 e Å⁻³
347 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
C15	0.60752 (15)	0.6051 (5)	0.34113 (19)	0.0475 (8)
H15	0.5903	0.5805	0.3847	0.057*
C16	0.56773 (14)	0.6125 (5)	0.2632 (2)	0.0469 (7)
H16	0.5247	0.5945	0.2550	0.056*
C17	0.59308 (16)	0.6471 (4)	0.19811 (19)	0.0426 (7)
C18	0.65698 (16)	0.6731 (5)	0.2138 (2)	0.0509 (8)
H18	0.6756	0.6968	0.1714	0.061*
C19	0.69323 (16)	0.6642 (5)	0.2921 (2)	0.0503 (8)
H19	0.7364	0.6813	0.3013	0.060*
C20	0.55604 (15)	0.6522 (4)	0.11228 (18)	0.0439 (7)
H20	0.5785	0.6646	0.0730	0.053*
C21	0.49369 (15)	0.6406 (4)	0.08599 (19)	0.0432 (7)
H21	0.4707	0.6305	0.1249	0.052*
C22	0.45867 (17)	0.6426 (4)	0.0007 (2)	0.0463 (7)
C23	0.39503 (16)	0.6076 (5)	−0.0194 (2)	0.0508 (8)
H23	0.3752	0.5854	0.0219	0.061*
C24	0.35978 (17)	0.6046 (5)	−0.0993 (2)	0.0528 (8)
H24	0.3169	0.5792	−0.1106	0.063*
C25	0.38713 (17)	0.6386 (4)	−0.1625 (2)	0.0488 (9)
C26	0.3479 (2)	0.6359 (6)	−0.2505 (2)	0.0645 (11)
H26A	0.3148	0.5475	−0.2563	0.097*
H26B	0.3743	0.6045	−0.2857	0.097*
H26C	0.3298	0.7540	−0.2650	0.097*
C27	0.45072 (17)	0.6768 (5)	−0.1433 (2)	0.0528 (8)
H27	0.4701	0.7017	−0.1848	0.063*
C28	0.48591 (16)	0.6788 (5)	−0.0640 (2)	0.0534 (8)
H28	0.5287	0.7047	−0.0530	0.064*
N2	0.66980 (12)	0.6322 (4)	0.35565 (15)	0.0429 (6)
C1	0.90157 (14)	0.5770 (4)	1.00260 (17)	0.0405 (6)
H1	0.8618	0.5307	1.0005	0.049*
C2	0.94592 (15)	0.5850 (4)	1.07603 (17)	0.0427 (7)
H2	0.9354	0.5465	1.1231	0.051*
C3	1.00631 (14)	0.6502 (4)	1.08064 (18)	0.0414 (7)
C4	1.01803 (13)	0.7114 (4)	1.00812 (17)	0.0435 (7)
H4	1.0573	0.7590	1.0080	0.052*
C5	0.97168 (14)	0.7011 (4)	0.93701 (18)	0.0416 (7)
H5	0.9803	0.7419	0.8892	0.050*
C6	1.05832 (15)	0.6634 (5)	1.15393 (19)	0.0450 (7)
H6	1.0948	0.7226	1.1497	0.054*
C7	1.05689 (15)	0.5970 (4)	1.22547 (19)	0.0448 (7)
H7	1.0202	0.5387	1.2294	0.054*
C8	1.10877 (16)	0.6076 (4)	1.29986 (18)	0.0431 (7)
C9	1.09635 (15)	0.5528 (5)	1.37169 (19)	0.0496 (8)
H9	1.0566	0.5082	1.3712	0.059*
C10	1.14133 (15)	0.5627 (5)	1.44370 (18)	0.0458 (7)
H10	1.1310	0.5240	1.4908	0.055*
C11	1.20160 (15)	0.6274 (4)	1.44981 (19)	0.0411 (7)
C12	1.2495 (2)	0.6363 (5)	1.5301 (2)	0.0601 (10)
H12A	1.2286	0.6551	1.5727	0.090*
H12B	1.2780	0.7353	1.5296	0.090*
H12C	1.2727	0.5242	1.5394	0.090*
C13	1.21454 (16)	0.6831 (5)	1.3776 (2)	0.0491 (8)
H13	1.2544	0.7269	1.3782	0.059*
C14	1.16861 (18)	0.6742 (5)	1.3042 (2)	0.0524 (8)
H14	1.1784	0.7140	1.2569	0.063*
C29	0.86448 (15)	0.6534 (4)	0.73719 (18)	0.0410 (7)
C30	0.82186 (14)	0.6520 (4)	0.65343 (17)	0.0396 (7)
H30	0.8396	0.6712	0.6099	0.048*
C31	0.76064 (15)	0.6252 (4)	0.63758 (18)	0.0417 (7)
H31	0.7427	0.6083	0.6811	0.050*
C32	0.71838 (13)	0.6204 (4)	0.55357 (17)	0.0396 (7)
N1	0.91506 (12)	0.6349 (3)	0.93414 (14)	0.0363 (5)
O1	0.83709 (10)	0.6285 (3)	0.79486 (12)	0.0462 (5)
H1A	0.8624	0.6449	0.8388	0.069*
O2	0.92070 (10)	0.6735 (4)	0.74538 (13)	0.0568 (6)
O3	0.74528 (10)	0.6312 (4)	0.49519 (13)	0.0488 (6)
H3	0.7190	0.6548	0.4528	0.073*
O4	0.66121 (11)	0.6046 (4)	0.54446 (15)	0.0623 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C15	0.0463 (17)	0.063 (2)	0.0318 (15)	0.0077 (14)	0.0067 (13)	−0.0051 (14)
C16	0.0359 (16)	0.0521 (17)	0.0466 (17)	0.0040 (12)	−0.0009 (13)	−0.0070 (14)
C17	0.0474 (17)	0.0378 (15)	0.0364 (15)	0.0037 (12)	−0.0012 (12)	−0.0046 (12)
C18	0.0479 (17)	0.064 (2)	0.0386 (16)	−0.0007 (15)	0.0075 (13)	−0.0005 (14)
C19	0.0410 (16)	0.067 (2)	0.0397 (17)	−0.0015 (14)	0.0033 (13)	0.0002 (14)
C20	0.0434 (17)	0.0549 (19)	0.0300 (14)	0.0017 (13)	0.0033 (12)	−0.0010 (12)
C21	0.0415 (16)	0.0472 (17)	0.0379 (15)	0.0023 (12)	0.0044 (13)	−0.0026 (13)
C22	0.0475 (17)	0.0399 (15)	0.0425 (17)	0.0016 (12)	−0.0055 (13)	−0.0022 (13)
C23	0.0495 (18)	0.0551 (19)	0.0440 (17)	0.0007 (14)	0.0045 (14)	−0.0001 (14)
C24	0.0426 (17)	0.0528 (19)	0.054 (2)	0.0020 (14)	−0.0047 (14)	−0.0045 (15)
C25	0.053 (2)	0.0395 (18)	0.0427 (18)	0.0021 (13)	−0.0086 (15)	−0.0037 (13)
C26	0.067 (2)	0.069 (3)	0.0405 (19)	0.0032 (17)	−0.0161 (17)	−0.0050 (16)
C27	0.0517 (18)	0.0572 (19)	0.0474 (19)	0.0003 (15)	0.0083 (15)	0.0081 (15)
C28	0.0417 (16)	0.0551 (19)	0.057 (2)	−0.0011 (14)	0.0001 (15)	0.0048 (16)
N2	0.0395 (14)	0.0538 (15)	0.0313 (13)	0.0044 (11)	0.0011 (10)	−0.0059 (11)
C1	0.0396 (14)	0.0480 (16)	0.0318 (14)	0.0002 (12)	0.0054 (11)	0.0000 (12)
C2	0.0487 (16)	0.0478 (16)	0.0286 (14)	0.0045 (13)	0.0043 (12)	0.0037 (12)
C3	0.0414 (15)	0.0398 (16)	0.0367 (16)	0.0076 (12)	−0.0019 (12)	−0.0091 (12)
C4	0.0379 (14)	0.0484 (16)	0.0423 (17)	−0.0037 (13)	0.0066 (13)	−0.0050 (13)
C5	0.0418 (15)	0.0453 (16)	0.0378 (15)	0.0014 (12)	0.0103 (13)	0.0006 (13)
C6	0.0427 (16)	0.0513 (17)	0.0363 (15)	−0.0025 (13)	0.0013 (13)	−0.0024 (13)
C7	0.0437 (15)	0.0439 (16)	0.0445 (18)	0.0014 (13)	0.0069 (14)	−0.0007 (13)
C8	0.0499 (17)	0.0396 (16)	0.0337 (15)	0.0079 (13)	−0.0006 (13)	−0.0020 (12)
C9	0.0435 (16)	0.0543 (19)	0.0467 (18)	−0.0002 (14)	0.0037 (14)	−0.0020 (15)
C10	0.0492 (17)	0.0552 (18)	0.0311 (14)	0.0028 (14)	0.0063 (12)	0.0009 (13)
C11	0.0435 (16)	0.0387 (16)	0.0351 (15)	0.0058 (12)	−0.0010 (13)	−0.0010 (12)
C12	0.058 (2)	0.062 (2)	0.049 (2)	0.0056 (16)	−0.0080 (17)	−0.0022 (16)
C13	0.0457 (17)	0.0525 (18)	0.0475 (18)	−0.0027 (14)	0.0089 (14)	0.0020 (15)
C14	0.071 (2)	0.0507 (18)	0.0362 (17)	0.0089 (16)	0.0157 (16)	0.0067 (13)
C29	0.0411 (16)	0.0510 (17)	0.0287 (14)	0.0015 (13)	0.0048 (12)	−0.0077 (12)
C30	0.0381 (16)	0.0531 (17)	0.0269 (14)	0.0014 (12)	0.0069 (12)	−0.0012 (12)
C31	0.0368 (15)	0.0555 (19)	0.0319 (15)	0.0043 (12)	0.0070 (12)	0.0029 (13)
C32	0.0305 (14)	0.0493 (17)	0.0357 (15)	0.0032 (12)	0.0022 (11)	0.0019 (13)
N1	0.0340 (12)	0.0419 (13)	0.0289 (11)	0.0027 (9)	0.0006 (9)	−0.0017 (9)
O1	0.0397 (11)	0.0734 (15)	0.0235 (9)	0.0009 (10)	0.0044 (8)	0.0016 (10)
O2	0.0336 (11)	0.1018 (19)	0.0336 (10)	−0.0073 (11)	0.0058 (9)	−0.0056 (12)
O3	0.0359 (10)	0.0776 (16)	0.0285 (11)	0.0020 (10)	0.0002 (8)	−0.0010 (10)
O4	0.0340 (11)	0.106 (2)	0.0431 (12)	0.0028 (12)	0.0025 (9)	0.0082 (13)

Geometric parameters (Å, º) top

C15—N2	1.341 (4)	C3—C6	1.465 (4)
C15—C16	1.392 (4)	C4—C5	1.372 (4)
C15—H15	0.9300	C4—H4	0.9300
C16—C17	1.382 (5)	C5—N1	1.324 (4)
C16—H16	0.9300	C5—H5	0.9300
C17—C18	1.374 (5)	C6—C7	1.318 (4)
C17—C20	1.481 (4)	C6—H6	0.9300
C18—C19	1.369 (5)	C7—C8	1.475 (4)
C18—H18	0.9300	C7—H7	0.9300
C19—N2	1.329 (4)	C8—C9	1.377 (5)
C19—H19	0.9300	C8—C14	1.386 (5)
C20—C21	1.331 (4)	C9—C10	1.367 (4)
C20—H20	0.9300	C9—H9	0.9300
C21—C22	1.460 (4)	C10—C11	1.385 (5)
C21—H21	0.9300	C10—H10	0.9300
C22—C23	1.376 (5)	C11—C13	1.390 (5)
C22—C28	1.404 (5)	C11—C12	1.500 (4)
C23—C24	1.383 (5)	C12—H12A	0.9600
C23—H23	0.9300	C12—H12B	0.9600
C24—C25	1.380 (6)	C12—H12C	0.9600
C24—H24	0.9300	C13—C14	1.394 (5)
C25—C27	1.380 (5)	C13—H13	0.9300
C25—C26	1.527 (5)	C14—H14	0.9300
C26—H26A	0.9600	C29—O2	1.216 (4)
C26—H26B	0.9600	C29—O1	1.286 (4)
C26—H26C	0.9600	C29—C30	1.494 (4)
C27—C28	1.373 (5)	C30—C31	1.317 (4)
C27—H27	0.9300	C30—H30	0.9300
C28—H28	0.9300	C31—C32	1.494 (4)
C1—N1	1.341 (4)	C31—H31	0.9300
C1—C2	1.377 (4)	C32—O4	1.231 (4)
C1—H1	0.9300	C32—O3	1.279 (4)
C2—C3	1.393 (5)	O1—H1A	0.8200
C2—H2	0.9300	O3—H3	0.8200
C3—C4	1.396 (4)

N2—C15—C16	122.3 (3)	C2—C3—C6	126.6 (3)
N2—C15—H15	118.8	C4—C3—C6	116.9 (3)
C16—C15—H15	118.8	C5—C4—C3	120.0 (3)
C17—C16—C15	119.1 (3)	C5—C4—H4	120.0
C17—C16—H16	120.4	C3—C4—H4	120.0
C15—C16—H16	120.4	N1—C5—C4	122.2 (3)
C18—C17—C16	117.9 (3)	N1—C5—H5	118.9
C18—C17—C20	117.9 (3)	C4—C5—H5	118.9
C16—C17—C20	124.2 (3)	C7—C6—C3	124.4 (3)
C19—C18—C17	119.8 (3)	C7—C6—H6	117.8
C19—C18—H18	120.1	C3—C6—H6	117.8
C17—C18—H18	120.1	C6—C7—C8	125.4 (3)
N2—C19—C18	123.3 (3)	C6—C7—H7	117.3
N2—C19—H19	118.3	C8—C7—H7	117.3
C18—C19—H19	118.3	C9—C8—C14	117.0 (3)
C21—C20—C17	126.3 (3)	C9—C8—C7	117.5 (3)
C21—C20—H20	116.9	C14—C8—C7	125.5 (3)
C17—C20—H20	116.9	C10—C9—C8	121.2 (3)
C20—C21—C22	124.9 (3)	C10—C9—H9	119.4
C20—C21—H21	117.6	C8—C9—H9	119.4
C22—C21—H21	117.6	C9—C10—C11	123.1 (3)
C23—C22—C28	116.6 (3)	C9—C10—H10	118.5
C23—C22—C21	119.5 (3)	C11—C10—H10	118.5
C28—C22—C21	124.0 (3)	C10—C11—C13	116.0 (3)
C22—C23—C24	121.9 (3)	C10—C11—C12	121.4 (3)
C22—C23—H23	119.1	C13—C11—C12	122.6 (3)
C24—C23—H23	119.1	C11—C12—H12A	109.5
C25—C24—C23	121.1 (3)	C11—C12—H12B	109.5
C25—C24—H24	119.5	H12A—C12—H12B	109.5
C23—C24—H24	119.5	C11—C12—H12C	109.5
C27—C25—C24	117.7 (3)	H12A—C12—H12C	109.5
C27—C25—C26	121.5 (4)	H12B—C12—H12C	109.5
C24—C25—C26	120.8 (3)	C11—C13—C14	121.0 (3)
C25—C26—H26A	109.5	C11—C13—H13	119.5
C25—C26—H26B	109.5	C14—C13—H13	119.5
H26A—C26—H26B	109.5	C8—C14—C13	121.7 (3)
C25—C26—H26C	109.5	C8—C14—H14	119.2
H26A—C26—H26C	109.5	C13—C14—H14	119.2
H26B—C26—H26C	109.5	O2—C29—O1	125.9 (3)
C28—C27—C25	121.3 (4)	O2—C29—C30	118.9 (3)
C28—C27—H27	119.3	O1—C29—C30	115.1 (3)
C25—C27—H27	119.3	C31—C30—C29	123.9 (3)
C27—C28—C22	121.4 (3)	C31—C30—H30	118.1
C27—C28—H28	119.3	C29—C30—H30	118.1
C22—C28—H28	119.3	C30—C31—C32	123.7 (3)
C19—N2—C15	117.5 (3)	C30—C31—H31	118.2
N1—C1—C2	120.9 (3)	C32—C31—H31	118.2
N1—C1—H1	119.6	O4—C32—O3	124.3 (3)
C2—C1—H1	119.6	O4—C32—C31	119.3 (3)
C1—C2—C3	120.7 (3)	O3—C32—C31	116.3 (3)
C1—C2—H2	119.6	C5—N1—C1	119.7 (3)
C3—C2—H2	119.6	C29—O1—H1A	109.5
C2—C3—C4	116.5 (3)	C32—O3—H3	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.74	2.548 (3)	169
O3—H3···N2	0.82	1.74	2.528 (3)	161

Experimental details

Crystal data
Chemical formula	2C₁₄H₁₃N·C₄H₄O₄
M_r	506.58
Crystal system, space group	Monoclinic, Cc
Temperature (K)	291
a, b, c (Å)	21.952 (1), 7.3477 (3), 17.0000 (7)
β (°)	104.610 (2)
V (Å³)	2653.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.24 × 0.23

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.979, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	12115, 3033, 2450
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.141, 1.00
No. of reflections	3033
No. of parameters	347
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.38

Computer programs: RAPID-AUTO (Rigaku, 1998), RAPID-AUTO, CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.