Benzoic acid–3,4-bis­[(pyridin-3-ylmeth­yl)amino]­cyclo­but-3-ene-1,2-dione (1/2)

Lemmerer, A.; Bourne, S.A.

doi:10.1107/S1600536812000220

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o384

doi:10.1107/S1600536812000220

Open

access

Benzoic acid–3,4-bis[(pyridin-3-ylmethyl)amino]cyclobut-3-ene-1,2-dione (1/2)

Andreas Lemmerer ^a ^* and Susan A. Bourne ^b

^aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Johannesburg, PO Wits 2050, South Africa, and ^bCentre for Supramolecular Chemistry Research, Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa
^*Correspondence e-mail: andreas.lemmerer@wits.ac.za

(Received 23 December 2011; accepted 3 January 2012; online 14 January 2012)

In the title co-crystal, C₁₆H₁₄N₄O₂·2C₇H₆O₂, the 3,4-bis[(pyridin-3-ylmethyl)amino]cyclobut-3-ene-1,2-dione squareamide molecules assemble into chains along the b axis via N—H⋯O hydrogen bonds. The benzoic acid molecules then hydrogen bond to the pyridine rings via O—H⋯N hydrogen bonds, supported by weaker C—H⋯O hydrogen bonds, forming extended ribbons. The asymmetric unit consists of a half squareamide molecule, sitting on a special position around a twofold axis, and one benzoic acid molecule on a general position.

Related literature

For the synthesis of related squareamides and co-crystals, see: Liu et al. (2002 ).

Experimental

Crystal data

C₁₆H₁₄N₄O₂·2C₇H₆O₂
M_r = 538.55
Monoclinic, C 2/c
a = 24.617 (5) Å
b = 6.0285 (12) Å
c = 17.806 (4) Å
β = 93.08 (3)°
V = 2638.6 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.49 × 0.16 × 0.14 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: integration (XPREP; Bruker, 2004 ) T_min = 0.944, T_max = 0.989
15016 measured reflections
3166 independent reflections
2110 reflections with I > 2σ(I)
R_int = 0.076

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.116
S = 0.99
3166 reflections
190 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.915 (16)	1.889 (17)	2.7697 (15)	161.0 (13)
O2—H2⋯N2	1.07 (2)	1.57 (2)	2.6380 (15)	178.0 (17)
C2—H2A⋯O3	0.95	2.68	3.3341 (18)	127
Symmetry code: (i) x, y-1, z.

Data collection: COLLECT (Nonius, 2000 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812000220/fy2039sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812000220/fy2039Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812000220/fy2039Isup3.mol

checkCIF report

Comment top

The title compound is a further example of co-crystals formed by squareamide molecules, in this case 3,4-bis[(pyridin-3-ylmethyl)amino]cyclobut-3-ene-1,2-dione, with carboxylic acid containing co-former molecules. Related co-crystals where the squaureamide molecule has the pyridine N atom in the 4 position are reported by Liu et al. (2002). The asymmetric unit consists of one half squareamide molecule, sitting around a twofold axis, and one complete benzoic acid molecule, on a general position (Fig. 1). The squareamide self-assembles into chains using the two N—H···O hydrogen bonds formed from the two amine N—-H groups to the diketones. The pyridine rings then act as hydrogen bond acceptors to the carboxylic acid functional group of the two benzoic acid molecules (Fig. 2).

Related literature top

For the synthesis of related squareamides and co-crystals, see: Liu et al. (2002).

Experimental top

The title squareamide compound was synthesized according to literature procedures (Liu et al., 2002) by double condensation of diethyl squarate with 1-(pyridin-3-yl)methanamine in ethanol by stirring for 12 h. The resulting solid was filtered and dried. The squareamide was then dissolved in a 1:2 stoichiometric ratio with benzoic acid in a 1/1 v/v mixture of methanol and water. Plate-like, colourless crystals were harvested after a few days by slow evaporation at ambient conditions.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of (I) showing the atom numbering scheme. Displacement ellipsoids are shown at the 50% probability level. Atoms with superscript i are generated by the symmetry operation (-x, y, -z + 1/2).
	Fig. 2. Hydrogen bonding diagram of the ribbons of (I). Intermolecular N—H···O and O—H···N hydrogen bonds are shown as dashed red lines.

Benzoic acid–3,4-bis[(pyridin-3-ylmethyl)amino]cyclobut-3-ene-1,2-dione (1/2) top

Crystal data top

C₁₆H₁₄N₄O₂·2C₇H₆O₂	F(000) = 1128
M_r = 538.55	D_x = 1.356 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 16004 reflections
a = 24.617 (5) Å	θ = 0.2–28.3°
b = 6.0285 (12) Å	µ = 0.10 mm⁻¹
c = 17.806 (4) Å	T = 173 K
β = 93.08 (3)°	Plate, colourless
V = 2638.6 (9) Å³	0.49 × 0.16 × 0.14 mm
Z = 4

Data collection top

Nonius KappaCCD area-detector diffractometer	2110 reflections with I > 2σ(I)
2.0° ω scans	R_int = 0.076
Absorption correction: integration (XPREP; Bruker, 2004)	θ_max = 28.0°, θ_min = 2.3°
T_min = 0.944, T_max = 0.989	h = −32→26
15016 measured reflections	k = −7→7
3166 independent reflections	l = −23→21

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0659P)² + ] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.044	(Δ/σ)_max < 0.001
wR(F²) = 0.116	Δρ_max = 0.23 e Å⁻³
S = 0.99	Δρ_min = −0.24 e Å⁻³
3166 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
190 parameters	Extinction coefficient: 0.0097 (11)
0 restraints

Crystal data top

C₁₆H₁₄N₄O₂·2C₇H₆O₂	V = 2638.6 (9) Å³
M_r = 538.55	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 24.617 (5) Å	µ = 0.10 mm⁻¹
b = 6.0285 (12) Å	T = 173 K
c = 17.806 (4) Å	0.49 × 0.16 × 0.14 mm
β = 93.08 (3)°

Data collection top

Nonius KappaCCD area-detector diffractometer	3166 independent reflections
Absorption correction: integration (XPREP; Bruker, 2004)	2110 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.989	R_int = 0.076
15016 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.23 e Å⁻³
3166 reflections	Δρ_min = −0.24 e Å⁻³
190 parameters

Special details top

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004).

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.

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

	x	y	z	U_iso*/U_eq
C1	0.09548 (5)	0.7538 (2)	0.57965 (7)	0.0286 (3)
C2	0.10973 (5)	0.5561 (2)	0.54679 (7)	0.0333 (3)
H2A	0.0814	0.4569	0.5308	0.04*
C3	0.20066 (6)	0.6353 (3)	0.55968 (8)	0.0417 (4)
H3	0.2373	0.5946	0.5526	0.05*
C4	0.19060 (6)	0.8346 (3)	0.59354 (8)	0.0430 (4)
H4	0.2198	0.929	0.61	0.052*
C5	0.13726 (6)	0.8956 (2)	0.60321 (7)	0.0366 (3)
H5	0.1293	1.0337	0.6259	0.044*
C6	0.03667 (5)	0.8124 (2)	0.58837 (7)	0.0307 (3)
H6A	0.0312	0.9723	0.5777	0.037*
H6B	0.0136	0.7275	0.5513	0.037*
C7	0.00897 (5)	0.91990 (19)	0.71280 (7)	0.0261 (3)
C8	0.01001 (5)	1.16213 (19)	0.71131 (7)	0.0293 (3)
N1	0.02002 (4)	0.76350 (17)	0.66414 (6)	0.0298 (3)
H1	0.0195 (6)	0.616 (3)	0.6757 (8)	0.041 (4)*
N2	0.16108 (5)	0.49629 (19)	0.53623 (6)	0.0384 (3)
O1	0.02247 (4)	1.30418 (13)	0.66529 (5)	0.0373 (3)
C9	0.14385 (5)	−0.1060 (2)	0.36020 (7)	0.0350 (3)
C10	0.18500 (6)	−0.0836 (2)	0.31016 (8)	0.0423 (4)
H10	0.208	0.0431	0.3128	0.051*
C11	0.19255 (7)	−0.2448 (3)	0.25655 (9)	0.0513 (4)
H11	0.2201	−0.2273	0.2217	0.062*
C12	0.16006 (8)	−0.4312 (3)	0.25359 (9)	0.0573 (5)
H12	0.1657	−0.543	0.2172	0.069*
C13	0.11934 (8)	−0.4557 (3)	0.30324 (10)	0.0559 (5)
H13	0.0972	−0.5848	0.3013	0.067*
C14	0.11075 (6)	−0.2923 (3)	0.35590 (8)	0.0452 (4)
H14	0.0821	−0.3078	0.3892	0.054*
C15	0.13450 (6)	0.0665 (2)	0.41783 (8)	0.0374 (4)
O2	0.17883 (4)	0.18069 (17)	0.43789 (6)	0.0443 (3)
H2	0.1708 (7)	0.309 (3)	0.4774 (11)	0.080 (6)*
O3	0.09068 (4)	0.09691 (18)	0.44435 (6)	0.0484 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0315 (7)	0.0303 (7)	0.0247 (6)	0.0022 (5)	0.0069 (5)	0.0042 (5)
C2	0.0308 (7)	0.0342 (7)	0.0355 (7)	0.0025 (6)	0.0083 (6)	−0.0004 (5)
C3	0.0282 (8)	0.0576 (9)	0.0400 (8)	0.0050 (7)	0.0092 (6)	0.0049 (7)
C4	0.0339 (8)	0.0501 (9)	0.0452 (8)	−0.0078 (7)	0.0033 (6)	0.0024 (7)
C5	0.0401 (8)	0.0324 (7)	0.0376 (8)	−0.0007 (6)	0.0065 (6)	0.0003 (6)
C6	0.0320 (7)	0.0289 (7)	0.0319 (7)	0.0048 (5)	0.0081 (5)	0.0008 (5)
C7	0.0227 (6)	0.0211 (6)	0.0353 (7)	0.0006 (5)	0.0073 (5)	0.0000 (5)
C8	0.0282 (7)	0.0219 (6)	0.0384 (7)	0.0012 (5)	0.0084 (5)	0.0004 (5)
N1	0.0355 (6)	0.0203 (6)	0.0348 (6)	0.0017 (5)	0.0130 (5)	0.0013 (4)
N2	0.0335 (7)	0.0443 (7)	0.0384 (7)	0.0092 (5)	0.0103 (5)	−0.0012 (5)
O1	0.0468 (6)	0.0225 (5)	0.0440 (5)	−0.0014 (4)	0.0159 (4)	0.0046 (4)
C9	0.0308 (7)	0.0419 (8)	0.0324 (7)	0.0077 (6)	0.0018 (6)	0.0064 (6)
C10	0.0372 (8)	0.0459 (8)	0.0445 (9)	0.0044 (6)	0.0093 (7)	0.0008 (6)
C11	0.0507 (10)	0.0624 (11)	0.0417 (9)	0.0148 (8)	0.0099 (7)	−0.0028 (8)
C12	0.0702 (12)	0.0560 (11)	0.0441 (9)	0.0146 (9)	−0.0110 (9)	−0.0100 (7)
C13	0.0640 (12)	0.0507 (10)	0.0510 (10)	−0.0084 (8)	−0.0155 (9)	−0.0003 (8)
C14	0.0393 (9)	0.0593 (10)	0.0367 (8)	−0.0032 (7)	−0.0025 (6)	0.0077 (7)
C15	0.0310 (8)	0.0460 (9)	0.0356 (8)	0.0100 (6)	0.0066 (6)	0.0074 (6)
O2	0.0331 (6)	0.0490 (6)	0.0518 (6)	0.0063 (5)	0.0112 (5)	−0.0115 (5)
O3	0.0322 (6)	0.0669 (7)	0.0472 (6)	0.0120 (5)	0.0133 (5)	0.0027 (5)

Geometric parameters (Å, º) top

C1—C2	1.3816 (18)	C8—C8ⁱ	1.488 (3)
C1—C5	1.3849 (19)	N1—H1	0.915 (16)
C1—C6	1.5061 (18)	C9—C14	1.387 (2)
C2—N2	1.3374 (17)	C9—C10	1.391 (2)
C2—H2A	0.95	C9—C15	1.487 (2)
C3—N2	1.3351 (19)	C10—C11	1.382 (2)
C3—C4	1.373 (2)	C10—H10	0.95
C3—H3	0.95	C11—C12	1.378 (2)
C4—C5	1.383 (2)	C11—H11	0.95
C4—H4	0.95	C12—C13	1.380 (3)
C5—H5	0.95	C12—H12	0.95
C6—N1	1.4612 (16)	C13—C14	1.384 (2)
C6—H6A	0.99	C13—H13	0.95
C6—H6B	0.99	C14—H14	0.95
C7—N1	1.3187 (16)	C15—O3	1.2146 (16)
C7—C7ⁱ	1.419 (2)	C15—O2	1.3231 (17)
C7—C8	1.4607 (17)	O2—H2	1.07 (2)
C8—O1	1.2354 (15)

C2—C1—C5	117.35 (12)	C7—N1—C6	122.71 (11)
C2—C1—C6	120.89 (12)	C7—N1—H1	122.9 (9)
C5—C1—C6	121.76 (12)	C6—N1—H1	114.3 (9)
N2—C2—C1	123.74 (13)	C3—N2—C2	117.80 (12)
N2—C2—H2A	118.1	C14—C9—C10	119.28 (14)
C1—C2—H2A	118.1	C14—C9—C15	119.46 (13)
N2—C3—C4	122.74 (13)	C10—C9—C15	121.26 (13)
N2—C3—H3	118.6	C11—C10—C9	120.24 (15)
C4—C3—H3	118.6	C11—C10—H10	119.9
C3—C4—C5	118.83 (14)	C9—C10—H10	119.9
C3—C4—H4	120.6	C12—C11—C10	120.03 (16)
C5—C4—H4	120.6	C12—C11—H11	120
C4—C5—C1	119.53 (13)	C10—C11—H11	120
C4—C5—H5	120.2	C11—C12—C13	120.19 (15)
C1—C5—H5	120.2	C11—C12—H12	119.9
N1—C6—C1	111.52 (10)	C13—C12—H12	119.9
N1—C6—H6A	109.3	C12—C13—C14	120.03 (16)
C1—C6—H6A	109.3	C12—C13—H13	120
N1—C6—H6B	109.3	C14—C13—H13	120
C1—C6—H6B	109.3	C13—C14—C9	120.20 (16)
H6A—C6—H6B	108	C13—C14—H14	119.9
N1—C7—C7ⁱ	134.35 (7)	C9—C14—H14	119.9
N1—C7—C8	134.30 (12)	O3—C15—O2	123.58 (13)
C7ⁱ—C7—C8	91.35 (7)	O3—C15—C9	123.19 (14)
O1—C8—C7	135.25 (12)	O2—C15—C9	113.22 (12)
O1—C8—C8ⁱ	136.11 (7)	C15—O2—H2	111.9 (10)
C7—C8—C8ⁱ	88.64 (7)

C5—C1—C2—N2	−0.52 (19)	C4—C3—N2—C2	−0.2 (2)
C6—C1—C2—N2	178.76 (11)	C1—C2—N2—C3	0.8 (2)
N2—C3—C4—C5	−0.7 (2)	C14—C9—C10—C11	0.3 (2)
C3—C4—C5—C1	0.9 (2)	C15—C9—C10—C11	−179.30 (13)
C2—C1—C5—C4	−0.35 (19)	C9—C10—C11—C12	−1.5 (2)
C6—C1—C5—C4	−179.62 (12)	C10—C11—C12—C13	1.1 (2)
C2—C1—C6—N1	98.57 (14)	C11—C12—C13—C14	0.5 (2)
C5—C1—C6—N1	−82.19 (14)	C12—C13—C14—C9	−1.6 (2)
N1—C7—C8—O1	−1.8 (3)	C10—C9—C14—C13	1.2 (2)
C7ⁱ—C7—C8—O1	178.55 (15)	C15—C9—C14—C13	−179.17 (13)
N1—C7—C8—C8ⁱ	178.45 (15)	C14—C9—C15—O3	−25.7 (2)
C7ⁱ—C7—C8—C8ⁱ	−1.20 (14)	C10—C9—C15—O3	153.96 (14)
C7ⁱ—C7—N1—C6	178.04 (17)	C14—C9—C15—O2	153.46 (12)
C8—C7—N1—C6	−1.5 (2)	C10—C9—C15—O2	−26.92 (18)
C1—C6—N1—C7	110.22 (13)

Symmetry code: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱⁱ	0.915 (16)	1.889 (17)	2.7697 (15)	161.0 (13)
O2—H2···N2	1.07 (2)	1.57 (2)	2.6380 (15)	178.0 (17)
C2—H2A···O3	0.95	2.68	3.3341 (18)	127

Symmetry code: (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₄O₂·2C₇H₆O₂
M_r	538.55
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	24.617 (5), 6.0285 (12), 17.806 (4)
β (°)	93.08 (3)
V (Å³)	2638.6 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.49 × 0.16 × 0.14

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Integration (XPREP; Bruker, 2004)
T_min, T_max	0.944, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	15016, 3166, 2110
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.116, 0.99
No. of reflections	3166
No. of parameters	190
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.24

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.915 (16)	1.889 (17)	2.7697 (15)	161.0 (13)
O2—H2···N2	1.07 (2)	1.57 (2)	2.6380 (15)	178.0 (17)
C2—H2A···O3	0.95	2.68	3.3341 (18)	127

Symmetry code: (i) x, y−1, z.

Acknowledgements

This work was supported by the University of the Witwatersrand, which is thanked for providing the infrastructure required to do this work.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2004). XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Liu, Y., Lam, A. H. W., Fowler, F. W. & Lauher, J. W. (2002). Mol. Cryst. Liq. Cryst. 389, 39–46. CrossRef CAS Google Scholar
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o384

doi:10.1107/S1600536812000220

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Benzoic acid–3,4-bis­­[(pyridin-3-ylmeth­yl)amino]­cyclo­but-3-ene-1,2-dione (1/2)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Benzoic acid–3,4-bis[(pyridin-3-ylmethyl)amino]cyclobut-3-ene-1,2-dione (1/2)