Crystallization, structural study and analysis of inter­molecular inter­actions of a 2-amino­benzoxazole–fumaric acid mol­ecular salt

A way to crystallize the 2-amino­benzoxazole–fumaric acid (1:1) co-crystal in the form of a mol­ecular salt was proposed. Its structure was analysed from topological (Hirshfeld surface analysis) and energetic approaches (analysis of the distribution of pairwise inter­action energies).

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2021); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

2-Aminobenzoxazol-3-ium 3-carboxyprop-2-enoate

Crystal data

C7H7N2O^+·C4H3O4^−	Dx = 1.481 Mg m^−3
Mr = 250.21	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbca	Cell parameters from 4322 reflections
a = 7.0694 (1) Å	θ = 3.6–70.5°
b = 12.9543 (2) Å	µ = 1.02 mm^−1
c = 24.5079 (4) Å	T = 293 K
V = 2244.41 (6) Å^3	Needle, clear light colourless
Z = 8	0.16 × 0.14 × 0.12 mm
F(000) = 1040

Data collection

XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer	2129 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	1871 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	Rint = 0.023
ω scans	θmax = 70.0°, θmin = 3.6°
Absorption correction: multi-scan CrysAlisPro; Rigaku OD, 2021)	h = −8→7
Tmin = 0.761, Tmax = 1.000	k = −9→15
7276 measured reflections	l = −29→25

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.035	w = 1/[σ^2(Fo^2) + (0.0485P)^2 + 0.5023P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.096	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.20 e Å^−3
2129 reflections	Δρmin = −0.16 e Å^−3
180 parameters	Extinction correction: SHELXL2016/6 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00154 (19)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.17549 (16)	0.32002 (7)	0.49841 (4)	0.0404 (3)
O3	0.35863 (16)	0.61279 (7)	0.38952 (4)	0.0403 (3)
O2	0.33909 (18)	0.47799 (7)	0.33433 (4)	0.0483 (3)
O4	0.59585 (19)	0.87984 (7)	0.25587 (4)	0.0499 (3)
O5	0.49429 (19)	0.75736 (8)	0.19951 (4)	0.0533 (3)
N1	0.26884 (18)	0.46854 (8)	0.46302 (5)	0.0350 (3)
N2	0.2529 (2)	0.32025 (9)	0.40757 (5)	0.0473 (3)
C7	0.23633 (19)	0.48645 (10)	0.51866 (5)	0.0334 (3)
C8	0.3664 (2)	0.57206 (9)	0.34298 (5)	0.0345 (3)
C1	0.2335 (2)	0.36996 (10)	0.45327 (5)	0.0352 (3)
C2	0.1779 (2)	0.39363 (10)	0.54042 (6)	0.0358 (3)
C11	0.5249 (2)	0.78833 (10)	0.24496 (5)	0.0365 (3)
C10	0.4884 (2)	0.72758 (10)	0.29520 (5)	0.0395 (3)
H10	0.523490	0.755361	0.328689	0.047*
C9	0.4091 (2)	0.63688 (10)	0.29419 (5)	0.0398 (3)
H9	0.376287	0.610288	0.260234	0.048*
C6	0.2553 (2)	0.57237 (11)	0.55113 (6)	0.0427 (4)
H6	0.294549	0.635506	0.537043	0.051*
C3	0.1326 (2)	0.37945 (12)	0.59423 (6)	0.0465 (4)
H3	0.092064	0.316219	0.607875	0.056*
C5	0.2129 (2)	0.55992 (13)	0.60616 (7)	0.0509 (4)
H5	0.225909	0.615872	0.629634	0.061*
C4	0.1516 (3)	0.46617 (13)	0.62683 (6)	0.0524 (4)
H4	0.122296	0.461317	0.663738	0.063*
H1	0.305 (3)	0.5194 (15)	0.4348 (8)	0.064 (6)*
H4A	0.613 (3)	0.9197 (18)	0.2214 (9)	0.091 (7)*
H2A	0.219 (3)	0.2538 (16)	0.4034 (8)	0.059 (5)*
H2B	0.294 (3)	0.3593 (16)	0.3773 (8)	0.070 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0619 (6)	0.0247 (5)	0.0345 (5)	−0.0050 (4)	0.0037 (4)	0.0047 (4)
O3	0.0674 (7)	0.0250 (5)	0.0287 (5)	−0.0012 (4)	0.0088 (4)	−0.0011 (4)
O2	0.0852 (8)	0.0237 (5)	0.0359 (5)	−0.0046 (5)	0.0142 (5)	−0.0037 (4)
O4	0.0817 (9)	0.0348 (5)	0.0332 (5)	−0.0152 (5)	0.0041 (5)	0.0024 (4)
O5	0.0897 (9)	0.0405 (6)	0.0296 (5)	−0.0093 (6)	−0.0004 (5)	−0.0009 (4)
N1	0.0524 (7)	0.0227 (5)	0.0300 (6)	−0.0019 (5)	0.0053 (5)	0.0025 (4)
N2	0.0812 (10)	0.0263 (6)	0.0343 (7)	−0.0064 (6)	0.0067 (6)	−0.0021 (5)
C7	0.0412 (7)	0.0286 (6)	0.0305 (7)	0.0016 (5)	0.0014 (6)	0.0023 (5)
C8	0.0480 (8)	0.0251 (6)	0.0305 (7)	0.0028 (5)	0.0064 (6)	0.0000 (5)
C1	0.0482 (8)	0.0254 (6)	0.0320 (7)	−0.0008 (5)	0.0016 (6)	0.0032 (5)
C2	0.0448 (7)	0.0298 (7)	0.0327 (7)	0.0001 (6)	0.0008 (6)	0.0028 (5)
C11	0.0482 (8)	0.0313 (6)	0.0299 (7)	−0.0007 (6)	0.0033 (6)	0.0007 (5)
C10	0.0562 (9)	0.0355 (7)	0.0268 (7)	−0.0066 (6)	0.0029 (6)	0.0002 (5)
C9	0.0628 (9)	0.0304 (7)	0.0264 (6)	−0.0021 (6)	0.0019 (6)	−0.0006 (5)
C6	0.0558 (9)	0.0304 (7)	0.0419 (8)	0.0017 (6)	0.0014 (7)	−0.0037 (6)
C3	0.0575 (9)	0.0467 (8)	0.0354 (8)	−0.0010 (7)	0.0044 (7)	0.0105 (6)
C5	0.0630 (10)	0.0488 (9)	0.0408 (8)	0.0083 (8)	−0.0001 (7)	−0.0130 (7)
C4	0.0636 (10)	0.0635 (10)	0.0303 (7)	0.0083 (8)	0.0046 (7)	0.0001 (7)

Geometric parameters (Å, º)

O1—C1	1.3456 (16)	C7—C6	1.375 (2)
O1—C2	1.4034 (16)	C8—C9	1.4918 (18)
O3—C8	1.2580 (15)	C2—C3	1.370 (2)
O2—C8	1.2519 (16)	C11—C10	1.4839 (17)
O4—C11	1.3148 (17)	C10—H10	0.9300
O4—H4A	1.00 (2)	C10—C9	1.302 (2)
O5—C11	1.2035 (16)	C9—H9	0.9300
N1—C7	1.4022 (17)	C6—H6	0.9300
N1—C1	1.3231 (17)	C6—C5	1.391 (2)
N1—H1	0.99 (2)	C3—H3	0.9300
N2—C1	1.2991 (18)	C3—C4	1.385 (2)
N2—H2A	0.90 (2)	C5—H5	0.9300
N2—H2B	0.94 (2)	C5—C4	1.385 (2)
C7—C2	1.3785 (19)	C4—H4	0.9300
C1—O1—C2	105.82 (10)	O5—C11—O4	123.88 (12)
C11—O4—H4A	109.9 (13)	O5—C11—C10	124.05 (13)
C7—N1—H1	127.8 (11)	C11—C10—H10	118.7
C1—N1—C7	107.72 (11)	C9—C10—C11	122.53 (13)
C1—N1—H1	124.4 (11)	C9—C10—H10	118.7
C1—N2—H2A	123.0 (12)	C8—C9—H9	117.3
C1—N2—H2B	116.4 (12)	C10—C9—C8	125.44 (13)
H2A—N2—H2B	120.4 (17)	C10—C9—H9	117.3
C2—C7—N1	106.32 (11)	C7—C6—H6	121.8
C6—C7—N1	132.90 (13)	C7—C6—C5	116.49 (14)
C6—C7—C2	120.77 (13)	C5—C6—H6	121.8
O3—C8—C9	119.97 (11)	C2—C3—H3	122.5
O2—C8—O3	123.71 (12)	C2—C3—C4	115.09 (14)
O2—C8—C9	116.32 (11)	C4—C3—H3	122.5
N1—C1—O1	111.91 (11)	C6—C5—H5	119.2
N2—C1—O1	120.18 (12)	C4—C5—C6	121.59 (14)
N2—C1—N1	127.90 (13)	C4—C5—H5	119.2
C7—C2—O1	108.22 (11)	C3—C4—C5	122.02 (14)
C3—C2—O1	127.76 (13)	C3—C4—H4	119.0
C3—C2—C7	124.02 (14)	C5—C4—H4	119.0
O4—C11—C10	112.07 (11)
O1—C2—C3—C4	178.81 (15)	C1—O1—C2—C7	0.54 (15)
O3—C8—C9—C10	19.2 (2)	C1—O1—C2—C3	−179.11 (15)
O2—C8—C9—C10	−161.08 (16)	C1—N1—C7—C2	−0.81 (16)
O4—C11—C10—C9	176.32 (15)	C1—N1—C7—C6	177.88 (16)
O5—C11—C10—C9	−4.1 (3)	C2—O1—C1—N1	−1.09 (16)
N1—C7—C2—O1	0.15 (15)	C2—O1—C1—N2	177.33 (14)
N1—C7—C2—C3	179.82 (14)	C2—C7—C6—C5	0.0 (2)
N1—C7—C6—C5	−178.51 (15)	C2—C3—C4—C5	−0.3 (3)
C7—N1—C1—O1	1.21 (17)	C11—C10—C9—C8	−179.35 (14)
C7—N1—C1—N2	−177.07 (15)	C6—C7—C2—O1	−178.73 (13)
C7—C2—C3—C4	−0.8 (2)	C6—C7—C2—C3	0.9 (2)
C7—C6—C5—C4	−1.1 (2)	C6—C5—C4—C3	1.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1^i	0.93	2.58	3.4929 (17)	167
C3—H3···O5^ii	0.93	2.51	3.2563 (17)	137
N1—H1···O3	0.99 (2)	1.69 (2)	2.6720 (14)	175.8 (17)
O4—H4A···O2^iii	1.00 (2)	1.60 (2)	2.5913 (14)	174 (2)
N2—H2A···O3^iv	0.90 (2)	1.94 (2)	2.8355 (16)	176.4 (18)
N2—H2B···O2	0.94 (2)	1.89 (2)	2.7873 (16)	157.8 (18)

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