How the oxazole fragment influences the conformation of the tetra­oxazocane ring in a cyclo­hexanespiro-3′-(1,2,4,5,7-tetra­oxazocane): single-crystal X-ray and theoretical study

Khalilov, L.M.; Mescheryakova, E.S.; Bikmukhametov, K.S.; Makhmudiyarova, N.N.; Shangaraev, K.R.; Tulyabaev, A.R.

doi:10.1107/S2053229619012592

How the oxazole fragment influences the conformation of the tetraoxazocane ring in a cyclohexanespiro-3′-(1,2,4,5,7-tetraoxazocane): single-crystal X-ray and theoretical study

L. M. Khalilov, E. S. Mescheryakova, K. S. Bikmukhametov, N. N. Makhmudiyarova, K. R. Shangaraev and A. R. Tulyabaev

Single crystals of (2S,5R)-2-isopropyl-5-methyl-7-(5-methylisoxazol-3-yl)cyclohexanespiro-3′-(1,2,4,5,7-tetraoxazocane), C₁₆H₂₆N₂O₅, have been studied via X-ray diffraction. The tetraoxazocane ring adopts a boat–chair conformation in the crystalline state, which is due to intramolecular interactions. Conformational analysis of the tetraoxazocane fragment performed at the B3LYP/6-31G(d,2p) level of theory showed that there are three minima on the potential energy surface, one of which corresponds to the conformation realized in the solid state, but not to a global minimum. Analysis of the geometry and the topological parameters of the electron density at the (3,−1) bond critical points (BCPs), and the charge transfer in the tetraoxazocane ring indicated that there are stereoelectronic effects in the O—C—O and N—C—O fragments. There is a two-cross hyperconjugation in the N—C—O fragment between the lone electron pair of the N atom (lpN) and the antibonding orbital of a C—O bond (σ*_C—O) and vice versa between lpO and σ*_C—N. The oxazole substituent has a considerable effect on the geometry and the topological parameters of the electron density at the (3,−1) BCPs of the tetraoxazocane ring. The crystal structure is stabilized via intermolecular C—H

N and C—H

O hydrogen bonds, which is unambiguously confirmed with PIXEL calculations, a quantum theory of atoms in molecules (QTAIM) topological analysis of the electron density at the (3,−1) BCPs and a Hirshfeld analysis of the electrostatic potential. The molecules form zigzag chains in the crystal due to intermolecular C—H

N interactions being electrostatic in origin. The molecules are further stacked due to C—H

O hydrogen bonds. The dispersion component in the total stabilization energy of the crystal lattice is 68.09%.

Keywords: oxazole; tetraoxazocane; crystal structure; two-cross hyperconjugation; PIXEL; quantum chemistry; AIM.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619012592/ku3248sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619012592/ku3248Isup2.hkl Contains datablock I

CCDC reference: 1952562

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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(2S,5R)-2-Isopropyl-5-methyl-7-(5-methylisoxazol-3-yl)cyclohexanespiro-3'-(1,2,4,5,7-tetraoxazocane) top

Crystal data top

C₁₆H₂₆N₂O₅	F(000) = 352.0
M_r = 326.39	D_x = 1.284 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 6.4074 (4) Å	Cell parameters from 1493 reflections
b = 8.1772 (8) Å	θ = 2.5–26.3°
c = 16.3291 (9) Å	µ = 0.10 mm⁻¹
β = 99.241 (5)°	T = 293 K
V = 844.46 (11) Å³	Plank, colourless
Z = 2	0.75 × 0.23 × 0.11 mm

Data collection top

Agilent Xcalibur Eos diffractometer	3147 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2379 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 16.1709 pixels mm^-1	θ_max = 28.9°, θ_min = 2.5°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −10→9
T_min = 0.704, T_max = 1.000	l = −21→20
5338 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.056	w = 1/[σ²(F_o²) + (0.0514P)² + 0.1884P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.128	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.25 e Å⁻³
3147 reflections	Δρ_min = −0.16 e Å⁻³
212 parameters	Absolute structure: Flack x determined using 656 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.5 (8)
Primary atom site location: structure-invariant direct methods

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.

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

	x	y	z	U_iso*/U_eq
O7	−0.9126 (4)	−0.9809 (4)	−0.28427 (15)	0.0371 (7)
O13	−0.5739 (3)	−0.8689 (4)	−0.24519 (16)	0.0386 (7)
O8	−0.9905 (4)	−0.8626 (4)	−0.35081 (16)	0.0459 (8)
O12	−0.5929 (4)	−0.7332 (4)	−0.30505 (17)	0.0459 (7)
O16	−0.5834 (5)	−1.3525 (4)	−0.4259 (2)	0.0557 (9)
C14	−0.6042 (6)	−1.0921 (6)	−0.4075 (2)	0.0380 (10)
C1	−0.7741 (5)	−0.8959 (5)	−0.2211 (2)	0.0316 (9)
C4	−1.0387 (7)	−0.9002 (7)	−0.0910 (3)	0.0518 (13)
H4A	−0.948458	−0.853095	−0.043452	0.062*
H4B	−1.172796	−0.927703	−0.074106	0.062*
C6	−0.7285 (6)	−1.0176 (6)	−0.1475 (2)	0.0380 (10)
H6	−0.643455	−0.956015	−0.102574	0.046*
N10	−0.6885 (5)	−0.9355 (5)	−0.41200 (19)	0.0415 (9)
C3	−1.0762 (6)	−0.7738 (6)	−0.1602 (2)	0.0428 (11)
H3	−1.179184	−0.819318	−0.205252	0.051*
N15	−0.7190 (5)	−1.2155 (6)	−0.4394 (2)	0.0549 (11)
C2	−0.8720 (6)	−0.7416 (6)	−0.1940 (2)	0.0386 (10)
H2A	−0.901144	−0.667672	−0.240947	0.046*
H2B	−0.771694	−0.688321	−0.151564	0.046*
C11	−0.5603 (7)	−0.7982 (6)	−0.3840 (3)	0.0478 (11)
H11A	−0.587664	−0.712172	−0.425233	0.057*
H11B	−0.413037	−0.829402	−0.380108	0.057*
C17	−0.3915 (6)	−1.3016 (7)	−0.3880 (2)	0.0461 (12)
C5	−0.9375 (7)	−1.0539 (6)	−0.1167 (3)	0.0480 (12)
H5A	−1.033720	−1.107423	−0.160436	0.058*
H5B	−0.911250	−1.128158	−0.069797	0.058*
C9	−0.9127 (6)	−0.9151 (7)	−0.4236 (2)	0.0483 (12)
H9A	−0.953409	−0.835479	−0.467299	0.058*
H9B	−0.979222	−1.018170	−0.441895	0.058*
C20	−0.5953 (6)	−1.1690 (6)	−0.1606 (3)	0.0430 (11)
H20	−0.479007	−1.131949	−0.188375	0.052*
C18	−0.3952 (6)	−1.1416 (6)	−0.3751 (2)	0.0430 (11)
H18	−0.284448	−1.075902	−0.350161	0.052*
C21	−0.4967 (8)	−1.2403 (8)	−0.0772 (3)	0.0720 (16)
H21A	−0.430521	−1.154539	−0.042158	0.108*
H21B	−0.392731	−1.320597	−0.085466	0.108*
H21C	−0.604739	−1.290871	−0.051358	0.108*
C23	−1.1679 (8)	−0.6172 (8)	−0.1313 (3)	0.0646 (15)
H23A	−1.297831	−0.641094	−0.111568	0.097*
H23B	−1.194734	−0.541725	−0.176809	0.097*
H23C	−1.069202	−0.569678	−0.087307	0.097*
C19	−0.2301 (7)	−1.4310 (7)	−0.3677 (3)	0.0614 (14)
H19A	−0.252948	−1.487000	−0.318251	0.092*
H19B	−0.091796	−1.382563	−0.358950	0.092*
H19C	−0.240672	−1.507487	−0.412814	0.092*
C22	−0.7126 (9)	−1.3014 (7)	−0.2145 (3)	0.0641 (14)
H22A	−0.826947	−1.341715	−0.188796	0.096*
H22B	−0.617305	−1.389338	−0.220925	0.096*
H22C	−0.767770	−1.256802	−0.268034	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O7	0.0343 (13)	0.043 (2)	0.0323 (13)	−0.0025 (12)	0.0005 (11)	0.0018 (13)
O13	0.0302 (12)	0.0411 (19)	0.0442 (14)	−0.0016 (13)	0.0050 (10)	0.0096 (14)
O8	0.0391 (13)	0.055 (2)	0.0413 (15)	0.0067 (14)	0.0010 (11)	0.0038 (15)
O12	0.0540 (16)	0.038 (2)	0.0485 (16)	−0.0069 (15)	0.0160 (13)	0.0054 (15)
O16	0.0534 (17)	0.050 (2)	0.0598 (18)	−0.0056 (16)	−0.0027 (14)	−0.0102 (17)
C14	0.0344 (19)	0.049 (3)	0.031 (2)	−0.007 (2)	0.0081 (16)	−0.006 (2)
C1	0.0240 (15)	0.034 (3)	0.0363 (19)	−0.0046 (16)	0.0024 (13)	−0.0031 (19)
C4	0.051 (2)	0.056 (4)	0.053 (2)	0.002 (2)	0.0230 (19)	0.003 (3)
C6	0.0368 (19)	0.040 (3)	0.036 (2)	0.0008 (18)	0.0023 (16)	−0.001 (2)
N10	0.0344 (16)	0.051 (3)	0.0393 (18)	−0.0036 (17)	0.0053 (13)	0.0010 (18)
C3	0.040 (2)	0.050 (3)	0.038 (2)	0.008 (2)	0.0045 (17)	−0.008 (2)
N15	0.0425 (18)	0.054 (3)	0.063 (2)	−0.004 (2)	−0.0073 (17)	−0.010 (2)
C2	0.0383 (19)	0.039 (3)	0.0369 (19)	0.0006 (19)	0.0025 (16)	−0.0008 (19)
C11	0.050 (2)	0.045 (3)	0.053 (2)	−0.008 (2)	0.023 (2)	0.004 (2)
C17	0.039 (2)	0.059 (4)	0.038 (2)	−0.004 (2)	0.0017 (18)	0.001 (2)
C5	0.053 (2)	0.047 (3)	0.047 (2)	0.001 (2)	0.019 (2)	0.003 (2)
C9	0.045 (2)	0.062 (4)	0.036 (2)	0.004 (2)	0.0026 (17)	0.001 (2)
C20	0.047 (2)	0.038 (3)	0.045 (2)	0.0048 (19)	0.0101 (18)	0.004 (2)
C18	0.034 (2)	0.052 (3)	0.043 (2)	−0.010 (2)	0.0043 (17)	−0.007 (2)
C21	0.081 (3)	0.069 (4)	0.063 (3)	0.027 (3)	0.001 (3)	0.014 (3)
C23	0.067 (3)	0.073 (4)	0.056 (3)	0.018 (3)	0.015 (2)	−0.003 (3)
C19	0.064 (3)	0.061 (4)	0.057 (3)	0.007 (3)	0.001 (2)	−0.003 (3)
C22	0.083 (3)	0.039 (3)	0.071 (3)	0.003 (3)	0.017 (3)	−0.004 (3)

Geometric parameters (Å, º) top

O7—O8	1.480 (4)	C2—H2B	0.9700
O7—C1	1.429 (4)	C11—H11A	0.9700
O13—O12	1.471 (4)	C11—H11B	0.9700
O13—C1	1.418 (4)	C17—C18	1.326 (7)
O8—C9	1.427 (5)	C17—C19	1.480 (7)
O12—C11	1.440 (5)	C5—H5A	0.9700
O16—N15	1.414 (5)	C5—H5B	0.9700
O16—C17	1.350 (5)	C9—H9A	0.9700
C14—N10	1.387 (6)	C9—H9B	0.9700
C14—N15	1.307 (6)	C20—H20	0.9800
C14—C18	1.418 (6)	C20—C21	1.523 (6)
C1—C6	1.551 (5)	C20—C22	1.516 (7)
C1—C2	1.506 (6)	C18—H18	0.9300
C4—H4A	0.9700	C21—H21A	0.9600
C4—H4B	0.9700	C21—H21B	0.9600
C4—C3	1.522 (6)	C21—H21C	0.9600
C4—C5	1.505 (7)	C23—H23A	0.9600
C6—H6	0.9800	C23—H23B	0.9600
C6—C5	1.534 (5)	C23—H23C	0.9600
C6—C20	1.539 (6)	C19—H19A	0.9600
N10—C11	1.423 (6)	C19—H19B	0.9600
N10—C9	1.428 (5)	C19—H19C	0.9600
C3—H3	0.9800	C22—H22A	0.9600
C3—C2	1.523 (5)	C22—H22B	0.9600
C3—C23	1.515 (7)	C22—H22C	0.9600
C2—H2A	0.9700

C1—O7—O8	108.0 (3)	O16—C17—C19	115.7 (5)
C1—O13—O12	108.6 (2)	C18—C17—O16	109.8 (4)
C9—O8—O7	107.1 (3)	C18—C17—C19	134.4 (4)
C11—O12—O13	107.9 (3)	C4—C5—C6	111.6 (4)
C17—O16—N15	108.6 (4)	C4—C5—H5A	109.3
N10—C14—C18	128.3 (4)	C4—C5—H5B	109.3
N15—C14—N10	120.2 (4)	C6—C5—H5A	109.3
N15—C14—C18	111.4 (4)	C6—C5—H5B	109.3
O7—C1—C6	105.4 (3)	H5A—C5—H5B	108.0
O7—C1—C2	112.3 (3)	O8—C9—N10	113.8 (3)
O13—C1—O7	111.1 (3)	O8—C9—H9A	108.8
O13—C1—C6	104.4 (3)	O8—C9—H9B	108.8
O13—C1—C2	112.9 (3)	N10—C9—H9A	108.8
C2—C1—C6	110.2 (3)	N10—C9—H9B	108.8
H4A—C4—H4B	107.8	H9A—C9—H9B	107.7
C3—C4—H4A	109.1	C6—C20—H20	107.2
C3—C4—H4B	109.1	C21—C20—C6	110.1 (4)
C5—C4—H4A	109.1	C21—C20—H20	107.2
C5—C4—H4B	109.1	C22—C20—C6	114.9 (4)
C5—C4—C3	112.6 (3)	C22—C20—H20	107.2
C1—C6—H6	105.3	C22—C20—C21	110.0 (4)
C5—C6—C1	108.2 (3)	C14—C18—H18	127.4
C5—C6—H6	105.3	C17—C18—C14	105.2 (4)
C5—C6—C20	115.0 (4)	C17—C18—H18	127.4
C20—C6—C1	116.6 (3)	C20—C21—H21A	109.5
C20—C6—H6	105.3	C20—C21—H21B	109.5
C14—N10—C11	120.8 (3)	C20—C21—H21C	109.5
C14—N10—C9	119.3 (4)	H21A—C21—H21B	109.5
C11—N10—C9	117.8 (4)	H21A—C21—H21C	109.5
C4—C3—H3	107.9	H21B—C21—H21C	109.5
C4—C3—C2	110.2 (3)	C3—C23—H23A	109.5
C2—C3—H3	107.9	C3—C23—H23B	109.5
C23—C3—C4	111.5 (4)	C3—C23—H23C	109.5
C23—C3—H3	107.9	H23A—C23—H23B	109.5
C23—C3—C2	111.4 (4)	H23A—C23—H23C	109.5
C14—N15—O16	104.9 (3)	H23B—C23—H23C	109.5
C1—C2—C3	112.6 (4)	C17—C19—H19A	109.5
C1—C2—H2A	109.1	C17—C19—H19B	109.5
C1—C2—H2B	109.1	C17—C19—H19C	109.5
C3—C2—H2A	109.1	H19A—C19—H19B	109.5
C3—C2—H2B	109.1	H19A—C19—H19C	109.5
H2A—C2—H2B	107.8	H19B—C19—H19C	109.5
O12—C11—H11A	108.6	C20—C22—H22A	109.5
O12—C11—H11B	108.6	C20—C22—H22B	109.5
N10—C11—O12	114.8 (3)	C20—C22—H22C	109.5
N10—C11—H11A	108.6	H22A—C22—H22B	109.5
N10—C11—H11B	108.6	H22A—C22—H22C	109.5
H11A—C11—H11B	107.5	H22B—C22—H22C	109.5

O7—O8—C9—N10	−54.7 (5)	N10—C14—N15—O16	178.4 (3)
O7—C1—C6—C5	−63.1 (4)	N10—C14—C18—C17	−177.6 (4)
O7—C1—C6—C20	68.4 (4)	C3—C4—C5—C6	56.4 (5)
O7—C1—C2—C3	59.2 (4)	N15—O16—C17—C18	0.9 (5)
O13—O12—C11—N10	52.2 (4)	N15—O16—C17—C19	179.0 (4)
O13—C1—C6—C5	179.7 (3)	N15—C14—N10—C11	−174.6 (4)
O13—C1—C6—C20	−48.7 (4)	N15—C14—N10—C9	22.1 (6)
O13—C1—C2—C3	−174.3 (3)	N15—C14—C18—C17	−1.0 (5)
O8—O7—C1—O13	−76.8 (3)	C2—C1—C6—C5	58.3 (4)
O8—O7—C1—C6	170.8 (2)	C2—C1—C6—C20	−170.2 (3)
O8—O7—C1—C2	50.8 (4)	C11—N10—C9—O8	−57.7 (6)
O12—O13—C1—O7	76.7 (4)	C17—O16—N15—C14	−1.5 (4)
O12—O13—C1—C6	−170.2 (3)	C5—C4—C3—C2	−52.9 (5)
O12—O13—C1—C2	−50.5 (4)	C5—C4—C3—C23	−177.1 (4)
O16—C17—C18—C14	0.0 (5)	C5—C6—C20—C21	−72.6 (5)
C14—N10—C11—O12	−104.1 (4)	C5—C6—C20—C22	52.2 (5)
C14—N10—C9—O8	106.1 (5)	C9—N10—C11—O12	59.5 (5)
C1—O7—O8—C9	115.9 (3)	C20—C6—C5—C4	169.8 (3)
C1—O13—O12—C11	−113.5 (3)	C18—C14—N10—C11	1.8 (6)
C1—C6—C5—C4	−57.8 (5)	C18—C14—N10—C9	−161.6 (4)
C1—C6—C20—C21	159.1 (4)	C18—C14—N15—O16	1.5 (5)
C1—C6—C20—C22	−76.1 (5)	C23—C3—C2—C1	178.5 (3)
C4—C3—C2—C1	54.2 (4)	C19—C17—C18—C14	−177.5 (5)
C6—C1—C2—C3	−58.0 (4)

Topological parameters of electron density at the (3,-1) BCPs of (I) top

Bond	ρ(r) (e a.u.^-3)	-∇²ρ(r) (e a.u.^-5)
C1—O7	0.2556	0.6574	0.1954
O7—O8	0.2573	0.0619	0.0550
O8—C9	0.2541	0.5902	0.1526
C9—N10	0.2866	0.9809	0.0647
N10—C11	0.2907	1.0025	0.0582
C11—O12	0.2485	0.6356	0.1358
O12—O13	0.2635	0.0830	0.0498
O13—C1	0.2605	0.6306	0.1987
N10—C14	0.3112	1.941	0.0104
C14—N15	0.3652	0.7925	0.4275
N15—O16	0.3020	–0.4618	0.0213
O16—C17	0.2950	–0.2951	0.0525
C17—C18	0.3530	–1.0674	0.6134
C18—C14	0.3034	–0.9470	0.0615
C17—C19	0.2688	–0.7340	0.0220

The energies of stereoelectronic interactions obtained within NBO theory for (I) top

Interacting fragments	E_int	Interacting fragments	E_int
lp(O7) → σ*(C1—O13)	14.61	lp(O13) → σ*(C1—O7)	15.70
lp(O7) → σ*(O8—C9)	1.21	lp(O13) → σ*(C11—O12)	1.53
lp(O8) → σ*(C1—O7)	1.20	lp(O12) → σ*(C1—O13)	1.30
lp(O8) → σ*(C9—N10)	9.23	lp(O12) → σ*(N10—C11)	8.34
lp(N10) → σ*(O8—C9)	14.27	lp(N10) → σ*( C11—O12)	16.06
lp(N10) → σ*(C14—N15)	46.77	lp(N15) → σ*(C14—C18)	5.87
lp(N15) → σ*(O16—C17)	4.92	lp(O16) → σ*(C17—C18)	36.01
lp(O16) → σ*(C14—N15)	12.79

Theoretical energetic parameters (kcal mol^-1) for conformational transformations of (I) top

Conformer	-E₀ (Hartree)	ΔE⁰₀ (kcal mol^-1) (ΔE⁼₀)
TS1	1110.7557	5.82
TS2	1110.7325	20.40
TS3	1110.6819	52.13
Chair–chair	1110.7650	0.00
Boat–chair	1110.7624	1.62
Twist–boat–chair	1110.7596	3.39

Topological parameters of electron density at the (3,-1) BCPs for intermolecular interactions in the crystal of (I) top

Interaction	ρ(r) (e a.u.^-3)	∇²ρ(r) (e a.u.^-5)	ε	E (kcal mol^-1)	Symmetry code
C9—H9A···N15	0.0115	0.0358	0.0457	2.2	-x+1, y-1/2, -z
C18—H18···O8	0.0095	0.0386	0.9807	2.35	x+1, y, z
C11—H11B···O8	0.0081	0.0274	0.1013	1.66	x+1, y, z
C18—H18···O7	0.0091	0.0383	2.8719	2.32	x+1, y, z
H5A···H20	0.0050	0.0097	0.0962	0.35	x+1, y, z
H22A···H19C	0.0039	0.0142	0.2630	0.05	x+1, y, z
C3—H3···O13	0.0097	0.0347	0.0949	2.19	x+1, y, z
H4B···H21A	0.0021	0.0066	0.0925	0.21	x+1, y, z
H23B···H2B	0.0050	0.0175	0.1337	0.69	x+1, y, z
C19—H19C···N15	0.0036	0.0122	0.1494	0.5	x+1, y, z
C19—H19A···H23C—C23	0.0045	0.0162	0.2247	0.60	x-1, y+1, z
C21—H21B···C23	0.0053	0.0194	0.5203	0.78	x-1, y+1, z
C19—H19B···O8	0.0016	0.0074	0.4765	0.28	x-1, y+1, z
C19—H19C···N15	0.0057	0.0187	0.4230	0.94	-x+2, y-1/2, -z
C19—H19C···N10	0.0060	0.0214	0.2796	1.13	-x+2, y-1/2, -z
C11—H11A···?	0.0031	0.0107	2.9861	0.47	-x+2, y-1/2, -z
C22—H22B···O12	0.0028	0.0117	0.3131	0.44	x, y-1, z
C19—H19A···O12	0.0060	0.0219	0.1909	1.13	x, y-1, z
C11—H11A···O16	0.0047	0.0183	0.0406	0.87	x, y-1, z
H23C···H22A	0.0030	0.0101	0.1043	0.37	x, y-1, z
H2A···H22A	0.0040	0.0140	0.3840	0.56	x, y-1, z

Interaction energies (kcal mol^-1) obtained from PIXEL calculations for various molecular pairs in the crystal of (I) top

D—H···A	-E_Coul	-E_Pol	-E_Disp	E_Rep	-E_Tot	Symmetry code
C3—H3···O13	5.31	2.10	12.0	8.68	10.76	x+1, y, z
C18—H18···O7	5.31	2.10	12.0	8.68	10.76	x+1, y, z
C18—H18···O8	5.31	2.10	12.0	8.68	10.76	x+1, y, z
C11—H11B···O8	5.31	2.10	12.0	8.68	10.76	x+1, y, z
C19—H19C···N15	1.89	1.03	5.62	3.97	4.57	-x+2, y-1/2, -z
C19—H19C···N10	1.89	1.03	5.62	3.97	4.57	-x+2, y-1/2, -z
C19—H19C···C14	1.89	1.03	5.62	3.97	4.57	-x+2, y-1/2, -z
C11—H11A···O16	1.31	0.86	5.54	3.49	4.25	x, y-1, z
C9—H9A···N15	1.98	0.76	2.29	2.22	2.82	-x+1, y-1/2, -z
C19—H19A···H23C—C23	0.62	0.29	3.94	2.10	2.75	x-1, y+1, z
C21—H21B···C23	0.62	0.29	3.94	2.10	2.75	x-1, y+1, z
C23—H23A···C4	0.50	0.19	3.42	1.65	2.44	-x+1, y-1/2, -z+1
C5—H5A···H23A—C23	0.50	0.19	3.42	1.65	2.44	-x+1, y-1/2, -z+1

Topological parameters of electron density at the (3,-1) BCPs for intramolecular interactions in the crystal of (I) top

Interaction	ρ(r) (e a.u.^-3)	∇²ρ(r) (e a.u.^-5)	ε	E (kcal mol^-1)
C22—H22C···N15	0.0059	0.0190	0.4068	0.97
C22—H22C···O7	0.0109	0.0441	0.1658	2.79
C20—H20···C18	0.0034	0.0107	0.4853	0.47

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How the oxazole fragment influences the conformation of the tetra­oxazocane ring in a cyclo­hexanespiro-3′-(1,2,4,5,7-tetra­oxazocane): single-crystal X-ray and theoretical study

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How the oxazole fragment influences the conformation of the tetraoxazocane ring in a cyclohexanespiro-3′-(1,2,4,5,7-tetraoxazocane): single-crystal X-ray and theoretical study