The synthesis and detailed description of the crystal structure and energetic features of the 1:1 cocrystal of carbamazepine (5
H-dibenzo[
b,
f]azepine-5-carboxamide,
CBZ) with 3,5-dinitrobenzoic acid (
35DNBA),
i.e. C
15H
12N
2O·C
7H
4N
2O
6, 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

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.
Supporting information
CCDC reference: 1889542
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).
5
H-Dibenzo[
b,
f]azepine-5-carboxamide–3,5-dinitrobenzoic acid (1/1)
top
Crystal data top
C15H12N2O·C7H4N2O6 | F(000) = 928 |
Mr = 448.39 | Dx = 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 | Rint = 0.029 |
Detector resolution: 8.0013 pixels mm-1 | θmax = 32.4°, θmin = 3.2° |
ω scans | h = −16→15 |
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014) | k = −9→9 |
Tmin = 0.969, Tmax = 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(Fo2) + (0.0494P)2 + 0.8471P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
7052 reflections | Δρmax = 0.42 e Å−3 |
310 parameters | Δρmin = −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 | Uiso*/Ueq | |
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 topCg1 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···Cg1iv | 2.90 | 148.0 | | |
C31═O32···Cg2v | 3.3288 (8) | 99.08 (6) | | |
C16—O17···N28v | 3.0418 (11) | 90.53 | | |
C31—O32···N28vi | 2.8924 (11) | 90.62 | | |
N28—O30···C31vi | 2.9796 (12) | 83.39 | | |
N28—O29···C16v | 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 topInteractions 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) | | Etot | Eele | Epol | Edis | Erep |
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 |