Crystal structure and energetic features of the cocrystal of carbamazepine with 3,5-di­nitro­benzoic acid

Pawlędzio, S.; Trzybiński, D.; Woźniak, K.

doi:10.1107/S2053229619009896

Crystal structure and energetic features of the cocrystal of carbamazepine with 3,5-dinitrobenzoic acid

S. Pawlędzio, D. Trzybiński and K. Woźniak

The synthesis and detailed description of the crystal structure and energetic features of the 1:1 cocrystal of carbamazepine (5H-dibenzo[b,f]azepine-5-carboxamide, CBZ) with 3,5-dinitrobenzoic acid (35DNBA), i.e. C₁₅H₁₂N₂O·C₇H₄N₂O₆, are reported. The CBZ and 35DNBA molecules are packed in alternately arranged layers. Two characteristic R₂²(8) and R₂²(16) hydrogen-bond ring motifs have been found. The supramolecular architecture, besides the network of hydrogen bonds, is also stabilized by numerous C—H

π, C=O

π, N—O

C and C=O

N weak intermolecular contacts involving neighbouring molecules in the crystal network. Identified interactions have been discussed in detail on the basis of a structural and energetic analysis. The latter approach, performed using the Pixel and CrystalExplorer programs, yielded additional information about the lattice energy and energetic landscape of the respective interactions in the crystal of CBZ·3DNBA with the evaluation of electrostatic, polarization, repulsion and dispersion terms.

Keywords: carbamazepine; cocrystal; hydrogen bonds; nitro group interactions; crystal structure; crystal engineering; energy calculations; energy frameworks.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619009896/yf3179sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619009896/yf3179Isup2.hkl Contains datablock I
	Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619009896/yf3179sup3.pdf Additional figures, beta/tau angles and geometric parameters

CCDC reference: 1889542

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), PLATON (Spek, 2009) and CrystalExplorer17 (Turner et al., 2017).

5H-Dibenzo[b,f]azepine-5-carboxamide–3,5-dinitrobenzoic acid (1/1) top

Crystal data top

C₁₅H₁₂N₂O·C₇H₄N₂O₆	F(000) = 928
M_r = 448.39	D_x = 1.434 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.7545 (3) Å	Cell parameters from 13769 reflections
b = 6.47168 (18) Å	θ = 2.5–32.1°
c = 30.0313 (9) Å	µ = 0.11 mm⁻¹
β = 96.456 (3)°	T = 100 K
V = 2076.92 (11) Å³	, clear yellowish colourless
Z = 4	0.50 × 0.20 × 0.12 mm

Data collection top

Agilent SuperNova Dual Source diffractometer with an Eos detector	7052 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	5960 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 8.0013 pixels mm^-1	θ_max = 32.4°, θ_min = 3.2°
ω scans	h = −16→15
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	k = −9→9
T_min = 0.969, T_max = 0.991	l = −42→44
37711 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0494P)² + 0.8471P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
7052 reflections	Δρ_max = 0.42 e Å⁻³
310 parameters	Δρ_min = −0.35 e Å⁻³
3 restraints

Special details top

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.

Refinement. A good-quality single crystal of the investigated system was selected for X-ray diffraction data collection. The crystal was mounted with paratone-N oil to the MiTeGen micromount. Diffraction data were collected on the Agilent Technologies SuperNova Single Source Eos diffractometer with Mo Kα radiation (λ = 0.71073 Å) at T = 100 (2) K. The lattice parameters were obtained by least-squares fit to the optimized setting angles of the reflections collected by using the CrysAlis CCD software (Rigaku OD, 2015). Data were reduced using the CrysAlis RED program (Rigaku OD, 2015). The Gaussian absorption correction (Rigaku OD, 2015) using the multi-faceted crystal model was applied. The structural determination procedure was carried out using the SHELX package (Sheldrick, 2008). The structure was solved with direct methods, and then least-squares refinements were carried out based on full-matrix least-squares on F² using the SHELXL97 program (Sheldrick, 2008).

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

	x	y	z	U_iso*/U_eq
O17	0.10440 (6)	0.02924 (12)	0.35591 (2)	0.01730 (14)
N1	0.28829 (7)	0.08894 (14)	0.32812 (3)	0.01593 (15)
N18	0.28560 (8)	−0.04098 (15)	0.39997 (3)	0.01876 (17)
C2	0.22537 (8)	0.12375 (15)	0.28401 (3)	0.01481 (17)
C3	0.15547 (9)	0.30246 (16)	0.27508 (3)	0.01695 (18)
H3	0.153755	0.403736	0.296973	0.020*
C4	0.08803 (9)	0.32883 (16)	0.23313 (3)	0.01816 (18)
H4	0.041591	0.448572	0.226778	0.022*
C5	0.09024 (9)	0.17564 (17)	0.20072 (3)	0.01933 (19)
H5	0.043938	0.191990	0.172869	0.023*
C6	0.16117 (10)	−0.00108 (16)	0.20980 (3)	0.01977 (19)
H6	0.161717	−0.102545	0.187898	0.024*
C7	0.23238 (9)	−0.02988 (16)	0.25154 (3)	0.01728 (18)
C8	0.30825 (11)	−0.21648 (17)	0.25925 (4)	0.0241 (2)
H8	0.278834	−0.333070	0.243298	0.029*
C9	0.41549 (12)	−0.24077 (19)	0.28657 (4)	0.0272 (2)
H9	0.450827	−0.372070	0.287437	0.033*
C10	0.48255 (10)	−0.08454 (19)	0.31497 (4)	0.0241 (2)
C11	0.61353 (11)	−0.0958 (2)	0.32451 (4)	0.0336 (3)
H11	0.656127	−0.206915	0.313729	0.040*
C12	0.67987 (11)	0.0544 (3)	0.34952 (4)	0.0386 (4)
H12	0.766345	0.043295	0.355524	0.046*
C13	0.61860 (11)	0.2220 (3)	0.36581 (4)	0.0360 (3)
H13	0.664077	0.324238	0.382172	0.043*
C14	0.48866 (10)	0.2370 (2)	0.35761 (4)	0.0261 (2)
H14	0.446905	0.349052	0.368370	0.031*
C15	0.42232 (9)	0.08219 (17)	0.33314 (3)	0.01948 (19)
C16	0.22185 (9)	0.02271 (15)	0.36142 (3)	0.01433 (16)
O26	0.48023 (9)	−0.26301 (19)	0.50061 (4)	0.0435 (3)
O27	0.52666 (9)	−0.2631 (2)	0.43212 (3)	0.0472 (3)
O29	0.81208 (9)	−0.48446 (13)	0.61477 (3)	0.02671 (18)
O30	1.00582 (8)	−0.43955 (13)	0.60251 (3)	0.02557 (17)
O32	1.11081 (7)	−0.18870 (11)	0.45930 (2)	0.01769 (14)
O33	0.95548 (7)	−0.07446 (12)	0.40894 (2)	0.01860 (14)
N25	0.55571 (9)	−0.26580 (19)	0.47285 (4)	0.0318 (2)
N28	0.89281 (9)	−0.43074 (13)	0.59133 (3)	0.02014 (17)
C19	0.68964 (10)	−0.27536 (18)	0.48902 (4)	0.0220 (2)
C20	0.77467 (10)	−0.21567 (16)	0.46003 (3)	0.01936 (19)
H20	0.747784	−0.171036	0.431113	0.023*
C21	0.90158 (9)	−0.22456 (15)	0.47554 (3)	0.01550 (17)
C22	0.94029 (9)	−0.29444 (14)	0.51878 (3)	0.01598 (17)
H22	1.024961	−0.301556	0.529183	0.019*
C23	0.85085 (10)	−0.35304 (15)	0.54597 (3)	0.01766 (18)
C24	0.72394 (10)	−0.34432 (17)	0.53230 (3)	0.0214 (2)
H24	0.664876	−0.382617	0.551115	0.026*
C31	0.99973 (9)	−0.16011 (14)	0.44667 (3)	0.01486 (16)
H18A	0.2430 (12)	−0.095 (2)	0.4199 (4)	0.022 (3)*
H18B	0.3640 (9)	−0.071 (2)	0.4010 (5)	0.028 (4)*
H33	1.0109 (15)	−0.041 (3)	0.3924 (6)	0.059 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O17	0.0133 (3)	0.0228 (3)	0.0160 (3)	0.0006 (3)	0.0027 (2)	0.0024 (3)
N1	0.0121 (3)	0.0226 (4)	0.0132 (3)	0.0014 (3)	0.0019 (3)	0.0012 (3)
N18	0.0149 (4)	0.0255 (4)	0.0158 (4)	0.0011 (3)	0.0014 (3)	0.0051 (3)
C2	0.0128 (4)	0.0192 (4)	0.0126 (4)	−0.0004 (3)	0.0024 (3)	0.0002 (3)
C3	0.0160 (4)	0.0200 (4)	0.0150 (4)	0.0012 (3)	0.0025 (3)	−0.0010 (3)
C4	0.0156 (4)	0.0222 (5)	0.0167 (4)	0.0019 (3)	0.0018 (3)	0.0025 (3)
C5	0.0177 (4)	0.0265 (5)	0.0135 (4)	−0.0035 (4)	0.0009 (3)	0.0019 (3)
C6	0.0236 (5)	0.0214 (5)	0.0148 (4)	−0.0033 (4)	0.0043 (3)	−0.0031 (3)
C7	0.0190 (4)	0.0181 (4)	0.0155 (4)	−0.0005 (3)	0.0053 (3)	0.0001 (3)
C8	0.0335 (6)	0.0190 (5)	0.0210 (5)	0.0045 (4)	0.0087 (4)	0.0002 (4)
C9	0.0324 (6)	0.0249 (5)	0.0261 (5)	0.0126 (4)	0.0115 (4)	0.0064 (4)
C10	0.0190 (5)	0.0330 (6)	0.0215 (5)	0.0086 (4)	0.0072 (4)	0.0119 (4)
C11	0.0195 (5)	0.0532 (8)	0.0299 (6)	0.0145 (5)	0.0102 (4)	0.0215 (5)
C12	0.0139 (5)	0.0700 (10)	0.0319 (6)	0.0025 (5)	0.0024 (4)	0.0277 (6)
C13	0.0205 (5)	0.0596 (9)	0.0264 (6)	−0.0125 (5)	−0.0037 (4)	0.0150 (6)
C14	0.0193 (5)	0.0376 (6)	0.0206 (5)	−0.0057 (4)	−0.0008 (4)	0.0059 (4)
C15	0.0130 (4)	0.0291 (5)	0.0166 (4)	0.0015 (4)	0.0025 (3)	0.0070 (4)
C16	0.0148 (4)	0.0144 (4)	0.0138 (4)	0.0006 (3)	0.0020 (3)	−0.0010 (3)
O26	0.0224 (4)	0.0604 (7)	0.0506 (6)	0.0068 (4)	0.0171 (4)	0.0166 (5)
O27	0.0216 (4)	0.0818 (9)	0.0371 (5)	0.0051 (5)	−0.0017 (4)	0.0222 (5)
O29	0.0416 (5)	0.0233 (4)	0.0171 (3)	−0.0024 (3)	0.0114 (3)	0.0012 (3)
O30	0.0329 (4)	0.0250 (4)	0.0180 (3)	0.0046 (3)	−0.0009 (3)	0.0010 (3)
O32	0.0167 (3)	0.0186 (3)	0.0176 (3)	0.0005 (3)	0.0014 (2)	0.0011 (2)
O33	0.0170 (3)	0.0243 (4)	0.0147 (3)	0.0008 (3)	0.0028 (2)	0.0046 (3)
N25	0.0184 (4)	0.0414 (6)	0.0362 (5)	0.0043 (4)	0.0065 (4)	0.0150 (5)
N28	0.0326 (5)	0.0148 (4)	0.0135 (4)	0.0025 (3)	0.0048 (3)	−0.0006 (3)
C19	0.0168 (4)	0.0256 (5)	0.0241 (5)	0.0036 (4)	0.0046 (4)	0.0065 (4)
C20	0.0188 (4)	0.0218 (5)	0.0178 (4)	0.0031 (4)	0.0034 (3)	0.0047 (3)
C21	0.0180 (4)	0.0143 (4)	0.0146 (4)	0.0011 (3)	0.0038 (3)	0.0002 (3)
C22	0.0198 (4)	0.0133 (4)	0.0149 (4)	0.0018 (3)	0.0023 (3)	−0.0015 (3)
C23	0.0255 (5)	0.0147 (4)	0.0133 (4)	0.0029 (4)	0.0041 (3)	0.0009 (3)
C24	0.0236 (5)	0.0205 (5)	0.0214 (5)	0.0029 (4)	0.0089 (4)	0.0040 (4)
C31	0.0176 (4)	0.0134 (4)	0.0136 (4)	0.0002 (3)	0.0024 (3)	−0.0010 (3)

Geometric parameters (Å, º) top

O17—C16	1.2560 (11)	C12—H12	0.9300
N1—C2	1.4359 (12)	C12—C13	1.386 (2)
N1—C15	1.4330 (12)	C13—H13	0.9300
N1—C16	1.3619 (12)	C13—C14	1.3948 (16)
N18—C16	1.3424 (12)	C14—H14	0.9300
N18—H18A	0.868 (8)	C14—C15	1.3908 (16)
N18—H18B	0.862 (9)	O26—N25	1.2273 (14)
C2—C3	1.3890 (14)	O27—N25	1.2282 (15)
C2—C7	1.4004 (13)	O29—N28	1.2277 (12)
C3—H3	0.9300	O30—N28	1.2253 (12)
C3—C4	1.3917 (13)	O32—C31	1.2261 (12)
C4—H4	0.9300	O33—C31	1.3025 (11)
C4—C5	1.3915 (15)	O33—H33	0.846 (9)
C5—H5	0.9300	N25—C19	1.4687 (14)
C5—C6	1.3848 (15)	N28—C23	1.4747 (12)
C6—H6	0.9300	C19—C20	1.3864 (14)
C6—C7	1.4060 (14)	C19—C24	1.3845 (14)
C7—C8	1.4612 (15)	C20—H20	0.9300
C8—H8	0.9300	C20—C21	1.3928 (14)
C8—C9	1.3472 (17)	C21—C22	1.3937 (13)
C9—H9	0.9300	C21—C31	1.4986 (13)
C9—C10	1.4599 (18)	C22—H22	0.9300
C10—C11	1.4074 (15)	C22—C23	1.3829 (14)
C10—C15	1.4004 (16)	C23—C24	1.3814 (15)
C11—H11	0.9300	C24—H24	0.9300
C11—C12	1.378 (2)

C15—N1—C2	117.77 (7)	C12—C13—C14	119.91 (13)
C16—N1—C2	119.67 (8)	C14—C13—H13	120.0
C16—N1—C15	121.18 (8)	C13—C14—H14	120.4
C16—N18—H18A	117.5 (9)	C15—C14—C13	119.16 (12)
C16—N18—H18B	120.2 (10)	C15—C14—H14	120.4
H18A—N18—H18B	118.3 (14)	C10—C15—N1	119.10 (10)
C3—C2—N1	119.83 (8)	C14—C15—N1	118.93 (10)
C3—C2—C7	121.81 (9)	C14—C15—C10	121.91 (10)
C7—C2—N1	118.31 (9)	O17—C16—N1	119.72 (8)
C2—C3—H3	120.2	O17—C16—N18	122.17 (9)
C2—C3—C4	119.51 (9)	N18—C16—N1	118.07 (8)
C4—C3—H3	120.2	C31—O33—H33	114.1 (14)
C3—C4—H4	120.1	O26—N25—O27	124.24 (11)
C5—C4—C3	119.85 (9)	O26—N25—C19	118.36 (11)
C5—C4—H4	120.1	O27—N25—C19	117.40 (10)
C4—C5—H5	119.9	O29—N28—C23	117.62 (9)
C6—C5—C4	120.19 (9)	O30—N28—O29	124.99 (9)
C6—C5—H5	119.9	O30—N28—C23	117.39 (9)
C5—C6—H6	119.4	C20—C19—N25	118.18 (9)
C5—C6—C7	121.20 (9)	C24—C19—N25	118.16 (10)
C7—C6—H6	119.4	C24—C19—C20	123.66 (10)
C2—C7—C6	117.39 (9)	C19—C20—H20	121.0
C2—C7—C8	123.32 (9)	C19—C20—C21	117.99 (9)
C6—C7—C8	119.29 (9)	C21—C20—H20	121.0
C7—C8—H8	115.9	C20—C21—C22	120.25 (9)
C9—C8—C7	128.13 (11)	C20—C21—C31	121.50 (8)
C9—C8—H8	115.9	C22—C21—C31	118.24 (9)
C8—C9—H9	116.3	C21—C22—H22	120.5
C8—C9—C10	127.42 (10)	C23—C22—C21	118.97 (9)
C10—C9—H9	116.3	C23—C22—H22	120.5
C11—C10—C9	120.03 (11)	C22—C23—N28	118.56 (9)
C15—C10—C9	122.79 (10)	C24—C23—N28	118.54 (9)
C15—C10—C11	117.18 (12)	C24—C23—C22	122.89 (9)
C10—C11—H11	119.3	C19—C24—H24	121.9
C12—C11—C10	121.30 (13)	C23—C24—C19	116.24 (9)
C12—C11—H11	119.3	C23—C24—H24	121.9
C11—C12—H12	119.8	O32—C31—O33	125.55 (9)
C11—C12—C13	120.45 (11)	O32—C31—C21	120.28 (8)
C13—C12—H12	119.8	O33—C31—C21	114.17 (8)
C12—C13—H13	120.0

N1—C2—C3—C4	−175.76 (9)	C15—N1—C16—O17	−179.52 (9)
N1—C2—C7—C6	174.50 (9)	C15—N1—C16—N18	2.83 (14)
N1—C2—C7—C8	−4.88 (14)	C15—C10—C11—C12	−1.97 (16)
C2—N1—C15—C10	−69.20 (12)	C16—N1—C2—C3	77.77 (12)
C2—N1—C15—C14	113.56 (11)	C16—N1—C2—C7	−99.54 (11)
C2—N1—C16—O17	−13.22 (14)	C16—N1—C15—C10	97.36 (11)
C2—N1—C16—N18	169.14 (9)	C16—N1—C15—C14	−79.89 (13)
C2—C3—C4—C5	0.58 (15)	O26—N25—C19—C20	−160.53 (12)
C2—C7—C8—C9	−29.72 (17)	O26—N25—C19—C24	19.74 (18)
C3—C2—C7—C6	−2.75 (14)	O27—N25—C19—C20	20.14 (18)
C3—C2—C7—C8	177.87 (10)	O27—N25—C19—C24	−159.60 (12)
C3—C4—C5—C6	−1.21 (15)	O29—N28—C23—C22	−179.10 (9)
C4—C5—C6—C7	−0.17 (15)	O29—N28—C23—C24	0.13 (14)
C5—C6—C7—C2	2.10 (15)	O30—N28—C23—C22	−0.14 (13)
C5—C6—C7—C8	−178.49 (10)	O30—N28—C23—C24	179.09 (9)
C6—C7—C8—C9	150.91 (12)	N25—C19—C20—C21	179.86 (10)
C7—C2—C3—C4	1.45 (15)	N25—C19—C24—C23	179.31 (10)
C7—C8—C9—C10	−0.5 (2)	N28—C23—C24—C19	−178.36 (9)
C8—C9—C10—C11	−149.86 (12)	C19—C20—C21—C22	0.86 (15)
C8—C9—C10—C15	29.08 (18)	C19—C20—C21—C31	−179.13 (10)
C9—C10—C11—C12	177.04 (11)	C20—C19—C24—C23	−0.41 (17)
C9—C10—C15—N1	7.26 (15)	C20—C21—C22—C23	−0.47 (14)
C9—C10—C15—C14	−175.58 (10)	C20—C21—C31—O32	−172.63 (9)
C10—C11—C12—C13	−0.30 (18)	C20—C21—C31—O33	7.65 (13)
C11—C10—C15—N1	−173.77 (9)	C21—C22—C23—N28	178.78 (8)
C11—C10—C15—C14	3.39 (15)	C21—C22—C23—C24	−0.42 (15)
C11—C12—C13—C14	1.25 (18)	C22—C21—C31—O32	7.38 (14)
C12—C13—C14—C15	0.13 (17)	C22—C21—C31—O33	−172.34 (9)
C13—C14—C15—N1	174.64 (9)	C22—C23—C24—C19	0.84 (16)
C13—C14—C15—C10	−2.52 (16)	C24—C19—C20—C21	−0.42 (17)
C15—N1—C2—C3	−115.47 (10)	C31—C21—C22—C23	179.52 (9)
C15—N1—C2—C7	67.22 (12)

The geometry of hydrogen bonds and other intermolecular contacts identified in the CBZ.35DNBA cocrystal top

Cg1 and Cg2 denote the geometric centres of gravity of the C10–C15 and C19–C24 aromatic rings, respectively (Fig. 1).

Hydrogen bonds
	D—H	H···A	D···A	D—H···A
N18–H18A···O32ⁱ	0.867 (12)	2.041 (13)	2.8940 (11)	167.5 (12)
N18—H18B···O27	0.862 (10)	2.261 (12)	3.0260 (14)	147.9 (12)
O33—H33···O17ⁱⁱ	0.846 (17)	1.633 (17)	2.4749 (9)	173.3 (18)
C12—H12···O33	0.93	2.56	3.3876 (14)	148.0

Y—X···CgI contacts	X···CgI	Y—X···CgI
N25—O27···Cg1	3.515 (1)	138.76 (9)
C4—H4···Cg1ⁱⁱⁱ	2.77	138.0
C11—H11···Cg1^iv	2.90	148.0
C31═O32···Cg2^v	3.3288 (8)	99.08 (6)
C16—O17···N28^v	3.0418 (11)	90.53
C31—O32···N28^vi	2.8924 (11)	90.62
N28—O30···C31^vi	2.9796 (12)	83.39
N28—O29···C16^v	3.1037 (13)	88.19

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

The values of lattice energy and energies for the pairs of adjacent molecules for investigated system top

Interactions in brackets denote the shortest intermolecular contacts identified among respective pair of molecules. Cg1 and Cg2 denote the geometric centres of gravity of the C10–C15 and C19–C24 aromatic rings, respectively (Fig. 1).

Energy (kJ mol^-1)		E_tot	E_ele	E_pol	E_dis	E_rep
Lattice		-123.2	-82.8	-36.2	-115.2	111.1
Pair 1	(O33—H33···O17)	-83.8	-140.8	-34.1	-13.3	165.0
Pair 2	(N18—H18B···O27)	-18.1	-14.9	-2.8	-20.2	28.1
Pair 3	(C11—H11···Cg1)	-24.6	-9.9	-4.1	-28.7	22.3
Pair 4	(C4—H4···Cg1)	-23.5	-6.5	-1.3	-34.8	23.5
Pair 5	(C31═O32···Cg2)	-28.3	-12.5	-5.7	-24.5	16.9
Pair 6	(C31—O32···N28)	-41.5	-27.1	-4.7	-45.7	49.3
Pair 7	(C16—O17···N28)	-21.6	-3.1	-4.1	-36.9	27.3

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Crystal structure and energetic features of the cocrystal of carbamazepine with 3,5-di­nitro­benzoic acid

Supporting information

Crystal structure and energetic features of the cocrystal of carbamazepine with 3,5-dinitrobenzoic acid