N,N,N′,N′-Tetra­isobutyl­pyridine-2,6-dicarboxamide

Pojarová, M.; Dušek, M.; Makrlík, E.; Babain, V.A.; Vaňura, P.

doi:10.1107/S1600536811040608

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages o2896-o2897

doi:10.1107/S1600536811040608

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N,N,N′,N′-Tetraisobutylpyridine-2,6-dicarboxamide

Michaela Pojarová,^a ^* Michal Dušek,^a Emanuel Makrlík,^b Vasily A. Babain ^c and Petr Vaňura ^d

^aInstitute of Physics, AS CR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic, ^bFaculty of Environmental Sciences, Czech University of Life Sciences, Prague, Kamýcká 129, 165 21 Prague 6, Czech Republic, ^cKhlopin Radium Institute, Research and Production Association, 2nd Murinskiy Prospect b. 28, 194021 St Petersburg, Russian Federation, and ^dDepartment of Analytical Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic
^*Correspondence e-mail: pojarova@fzu.cz

(Received 26 September 2011; accepted 3 October 2011; online 8 October 2011)

In the title compound, C₂₃H₃₉N₃O₂, the amide O atoms are displaced by 1.020 (1) and 1.211 (1) Å from the mean plane of the central pyridine ring. In the crystal, molecules are connected by weak C—H⋯O hydrogen bonds between methylene groups in the isobutyl substituents and the amide O atoms.

Related literature

The title compound has been investigated for its extractive properties towards trivalent metals in a synergistic mixture with chlorinated cobalt dicarbollide. For further information, see: Alyapyshev et al. (2004 , 2006 ); Romanovskiy et al. (2006 ); Babain et al. (2007 ); Makrlík et al. (2009 , 2011 ). For further synthetic details, see: Nikitskaya et al. (1958 ); Shimada et al. (2004 ).

Experimental

Crystal data

C₂₃H₃₉N₃O₂
M_r = 389.57
Monoclinic, P 2₁ /c
a = 10.5247 (2) Å
b = 17.7765 (3) Å
c = 12.8773 (2) Å
β = 96.877 (2)°
V = 2391.91 (7) Å³
Z = 4
Cu Kα radiation
μ = 0.54 mm⁻¹
T = 120 K
0.49 × 0.42 × 0.23 mm

Data collection

Agilent Xcalibur Atlas Gemini ultra diffractometer
Absorption correction: analytical (CrysAlis PRO; Agilent, 2011 ) T_min = 0.929, T_max = 0.962
31214 measured reflections
4272 independent reflections
3867 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.112
S = 1.05
4272 reflections
261 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O2ⁱ	0.97	2.57	3.5226 (15)	166
C11—H11A⋯O1ⁱⁱ	0.97	2.55	3.4790 (15)	160
Symmetry codes: (i) x-1, y, z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ) and DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811040608/hb6423sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811040608/hb6423Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811040608/hb6423Isup3.cml

checkCIF report

Comment top

The title compound, (I), shown in Figure 1 and Scheme 1, has been investigated in a synergistic mixtures with the dicarbollylcobaltate anion and its halogen derivatives for significant extraction properties towards trivalent metal cations (Alyapyshev et al.,2004). It consists of pyridine ring with a di-isobutylamide groups in position 2 and 6. This molecule lacks of crystallographic symmetry and the asymmetric unit contains one molecule. While at first impression, the amide groups seem to be related by a mirror plane, closer look reveales their differences. The carbon atoms of carbonyl groups do not lay in a plane of the pyridine ring and they differ in the distance to this plane (0.062 Å for C6 and 0.234 Å for C15). The molecules form bands along the c axis (Fig. 2) via system of hydrogen bonds (Table 1).

Related literature top

The title compound has been investigated for its extractive properties towards trivalent metals in a synergistic mixture with chlorinated cobalt dicarbollide. For further information, see: Alyapyshev et al. (2004, 2006); Romanovskiy et al. (2006); Babain et al. (2007); Makrlík et al. (2009, 2011). For further synthetic details, see: Nikitskaya et al. (1958); Shimada et al. (2004).

Experimental top

The title compound was synthesized as described in Shimada et al. (2004), and Nikitskaya et al. (1958). Colourless prisms were prepared by slow evaporation from an acetonitrile solution.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. View of the N,N,N',N'-tetraisobutyl-2,6-dipicolinamide, together with atom-labelling scheme. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. Projection along the b axis with highlighted hydrogen bonds between the molecules in the bands in direction of c axis.

N,N,N',N'-Tetraisobutylpyridine-2,6-dicarboxamide top

Crystal data top

C₂₃H₃₉N₃O₂	F(000) = 856
M_r = 389.57	D_x = 1.082 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 15197 reflections
a = 10.5247 (2) Å	θ = 3.5–67.0°
b = 17.7765 (3) Å	µ = 0.54 mm⁻¹
c = 12.8773 (2) Å	T = 120 K
β = 96.877 (2)°	Prism, colourless
V = 2391.91 (7) Å³	0.49 × 0.42 × 0.23 mm
Z = 4

Data collection top

Agilent Xcalibur Atlas Gemini ultra diffractometer	4272 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	3867 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.039
Detector resolution: 10.3784 pixels mm^-1	θ_max = 67.1°, θ_min = 4.2°
Rotation method data acquisition using ω scans	h = −12→12
Absorption correction: analytical (CrysAlis PRO; Agilent, 2011)	k = −20→21
T_min = 0.929, T_max = 0.962	l = −15→15
31214 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0596P)² + 0.5367P] where P = (F_o² + 2F_c²)/3
4272 reflections	(Δ/σ)_max < 0.001
261 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₃H₃₉N₃O₂	V = 2391.91 (7) Å³
M_r = 389.57	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 10.5247 (2) Å	µ = 0.54 mm⁻¹
b = 17.7765 (3) Å	T = 120 K
c = 12.8773 (2) Å	0.49 × 0.42 × 0.23 mm
β = 96.877 (2)°

Data collection top

Agilent Xcalibur Atlas Gemini ultra diffractometer	4272 independent reflections
Absorption correction: analytical (CrysAlis PRO; Agilent, 2011)	3867 reflections with I > 2σ(I)
T_min = 0.929, T_max = 0.962	R_int = 0.039
31214 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.05	Δρ_max = 0.20 e Å⁻³
4272 reflections	Δρ_min = −0.14 e Å⁻³
261 parameters

Special details top

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The hydrogen atoms were localized from the difference Fourier map. Despite of that, all hydrogen atoms connected to C were constrained to ideal positions. The isotropic temperature parameters of hydrogen atoms were calculated as 1.2*U_eq of the parent atom.

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

	x	y	z	U_iso*/U_eq
C1	0.59347 (11)	0.14933 (7)	0.60811 (8)	0.0311 (3)
C2	0.60691 (12)	0.08382 (7)	0.55206 (9)	0.0371 (3)
H2	0.5408	0.0668	0.5033	0.044*
C3	0.72048 (12)	0.04424 (7)	0.57014 (10)	0.0402 (3)
H3	0.7308	−0.0011	0.5361	0.048*
C4	0.81870 (12)	0.07328 (7)	0.63991 (10)	0.0371 (3)
H4	0.8965	0.0482	0.6529	0.045*
C5	0.79847 (11)	0.14055 (7)	0.68995 (9)	0.0319 (3)
C6	0.47213 (11)	0.19491 (7)	0.58800 (9)	0.0329 (3)
N2	0.40863 (9)	0.21191 (6)	0.66956 (7)	0.0332 (2)
C7	0.30023 (11)	0.26406 (7)	0.65316 (9)	0.0363 (3)
H7A	0.2221	0.2366	0.6604	0.044*
H7B	0.2939	0.2832	0.5822	0.044*
C8	0.31001 (12)	0.33034 (8)	0.72858 (10)	0.0396 (3)
H8	0.3019	0.3115	0.7990	0.048*
C9	0.19691 (14)	0.38209 (9)	0.69475 (12)	0.0509 (4)
H9A	0.2051	0.4023	0.6267	0.061*
H9B	0.1958	0.4225	0.7441	0.061*
H9C	0.1187	0.3540	0.6922	0.061*
C10	0.43658 (14)	0.37205 (8)	0.73123 (12)	0.0492 (3)
H10A	0.5058	0.3383	0.7532	0.059*
H10B	0.4381	0.4133	0.7795	0.059*
H10C	0.4457	0.3909	0.6627	0.059*
C11	0.43174 (11)	0.17506 (7)	0.77252 (9)	0.0337 (3)
H11A	0.4472	0.2134	0.8261	0.040*
H11B	0.5083	0.1444	0.7748	0.040*
C12	0.32074 (12)	0.12556 (7)	0.79723 (10)	0.0383 (3)
H12	0.2446	0.1573	0.7971	0.046*
C13	0.29120 (17)	0.06398 (9)	0.71727 (12)	0.0577 (4)
H13A	0.3641	0.0315	0.7176	0.069*
H13B	0.2715	0.0859	0.6491	0.069*
H13C	0.2191	0.0353	0.7342	0.069*
C14	0.35334 (15)	0.09285 (8)	0.90645 (11)	0.0492 (3)
H14A	0.2806	0.0662	0.9261	0.059*
H14B	0.3756	0.1328	0.9553	0.059*
H14C	0.4244	0.0589	0.9068	0.059*
C15	0.90910 (11)	0.17978 (7)	0.75374 (10)	0.0352 (3)
N3	0.89638 (9)	0.20256 (6)	0.85171 (8)	0.0351 (2)
C16	0.99475 (11)	0.25225 (7)	0.90474 (10)	0.0375 (3)
H16A	1.0630	0.2581	0.8610	0.045*
H16B	1.0309	0.2288	0.9696	0.045*
C17	0.94382 (13)	0.32978 (7)	0.92891 (10)	0.0407 (3)
H17	0.8868	0.3241	0.9833	0.049*
C18	0.86814 (15)	0.36539 (9)	0.83386 (12)	0.0528 (4)
H18A	0.9224	0.3715	0.7796	0.063*
H18B	0.8369	0.4137	0.8526	0.063*
H18C	0.7972	0.3336	0.8092	0.063*
C19	1.05650 (15)	0.37855 (8)	0.97250 (11)	0.0505 (4)
H19A	1.1168	0.3817	0.9223	0.061*
H19B	1.0973	0.3567	1.0361	0.061*
H19C	1.0265	0.4281	0.9867	0.061*
C20	0.78661 (11)	0.18394 (7)	0.90704 (9)	0.0357 (3)
H20A	0.7305	0.1502	0.8638	0.043*
H20B	0.7390	0.2296	0.9166	0.043*
C21	0.82297 (11)	0.14717 (7)	1.01368 (9)	0.0355 (3)
H21	0.8725	0.1832	1.0598	0.043*
C22	0.69990 (13)	0.12864 (8)	1.05952 (10)	0.0417 (3)
H22A	0.6509	0.1738	1.0644	0.050*
H22B	0.7204	0.1073	1.1280	0.050*
H22C	0.6508	0.0932	1.0151	0.050*
C23	0.90338 (13)	0.07718 (8)	1.00455 (12)	0.0479 (3)
H23A	0.8561	0.0417	0.9589	0.057*
H23B	0.9241	0.0550	1.0725	0.057*
H23C	0.9808	0.0905	0.9765	0.057*
N1	0.68718 (9)	0.17810 (6)	0.67644 (7)	0.0313 (2)
O1	0.43906 (9)	0.21594 (6)	0.49754 (6)	0.0446 (2)
O2	1.00544 (8)	0.19100 (6)	0.71057 (8)	0.0493 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0313 (6)	0.0360 (6)	0.0262 (5)	−0.0027 (5)	0.0038 (4)	0.0022 (4)
C2	0.0380 (6)	0.0393 (6)	0.0333 (6)	−0.0044 (5)	0.0017 (5)	−0.0033 (5)
C3	0.0435 (7)	0.0359 (6)	0.0420 (7)	−0.0001 (5)	0.0077 (5)	−0.0060 (5)
C4	0.0333 (6)	0.0390 (6)	0.0398 (6)	0.0034 (5)	0.0074 (5)	0.0010 (5)
C5	0.0288 (6)	0.0388 (6)	0.0286 (6)	−0.0008 (5)	0.0061 (4)	0.0018 (5)
C6	0.0320 (6)	0.0379 (6)	0.0277 (6)	−0.0019 (5)	−0.0008 (5)	−0.0007 (5)
N2	0.0284 (5)	0.0426 (6)	0.0275 (5)	0.0028 (4)	−0.0008 (4)	0.0013 (4)
C7	0.0281 (6)	0.0455 (7)	0.0340 (6)	0.0033 (5)	−0.0010 (5)	0.0020 (5)
C8	0.0372 (7)	0.0482 (7)	0.0340 (6)	0.0029 (5)	0.0067 (5)	0.0000 (5)
C9	0.0511 (8)	0.0551 (8)	0.0475 (8)	0.0133 (7)	0.0104 (6)	−0.0011 (6)
C10	0.0484 (8)	0.0493 (8)	0.0498 (8)	−0.0065 (6)	0.0057 (6)	−0.0062 (6)
C11	0.0301 (6)	0.0429 (7)	0.0273 (6)	0.0001 (5)	0.0002 (5)	0.0012 (5)
C12	0.0304 (6)	0.0401 (7)	0.0440 (7)	−0.0004 (5)	0.0035 (5)	0.0019 (5)
C13	0.0676 (10)	0.0462 (8)	0.0541 (9)	−0.0115 (7)	−0.0138 (7)	0.0009 (7)
C14	0.0543 (8)	0.0517 (8)	0.0430 (7)	−0.0097 (7)	0.0122 (6)	0.0033 (6)
C15	0.0274 (6)	0.0416 (7)	0.0367 (6)	0.0023 (5)	0.0038 (5)	−0.0011 (5)
N3	0.0262 (5)	0.0459 (6)	0.0329 (5)	−0.0011 (4)	0.0019 (4)	−0.0031 (4)
C16	0.0293 (6)	0.0433 (7)	0.0384 (6)	−0.0012 (5)	−0.0020 (5)	−0.0018 (5)
C17	0.0454 (7)	0.0428 (7)	0.0346 (6)	0.0012 (6)	0.0076 (5)	0.0022 (5)
C18	0.0537 (8)	0.0545 (8)	0.0510 (8)	0.0108 (7)	0.0092 (7)	0.0135 (6)
C19	0.0655 (9)	0.0442 (7)	0.0423 (7)	−0.0099 (7)	0.0081 (7)	−0.0019 (6)
C20	0.0281 (6)	0.0470 (7)	0.0318 (6)	0.0005 (5)	0.0022 (5)	0.0002 (5)
C21	0.0345 (6)	0.0388 (6)	0.0314 (6)	−0.0003 (5)	−0.0027 (5)	−0.0028 (5)
C22	0.0443 (7)	0.0485 (7)	0.0323 (6)	0.0010 (6)	0.0040 (5)	0.0024 (5)
C23	0.0421 (7)	0.0436 (7)	0.0568 (8)	0.0036 (6)	0.0010 (6)	0.0029 (6)
N1	0.0294 (5)	0.0378 (5)	0.0268 (5)	−0.0005 (4)	0.0036 (4)	0.0000 (4)
O1	0.0461 (5)	0.0595 (6)	0.0272 (4)	0.0104 (4)	0.0001 (4)	0.0047 (4)
O2	0.0304 (5)	0.0735 (7)	0.0459 (5)	−0.0086 (4)	0.0117 (4)	−0.0119 (5)

Geometric parameters (Å, º) top

C1—N1	1.3419 (15)	C13—H13B	0.9600
C1—C2	1.3862 (17)	C13—H13C	0.9600
C1—C6	1.5084 (16)	C14—H14A	0.9600
C2—C3	1.3825 (18)	C14—H14B	0.9600
C2—H2	0.9300	C14—H14C	0.9600
C3—C4	1.3856 (18)	C15—O2	1.2295 (15)
C3—H3	0.9300	C15—N3	1.3469 (16)
C4—C5	1.3868 (18)	N3—C20	1.4660 (15)
C4—H4	0.9300	N3—C16	1.4660 (16)
C5—N1	1.3412 (15)	C16—C17	1.5242 (18)
C5—C15	1.5125 (17)	C16—H16A	0.9700
C6—O1	1.2332 (14)	C16—H16B	0.9700
C6—N2	1.3450 (16)	C17—C18	1.5165 (19)
N2—C7	1.4655 (15)	C17—C19	1.521 (2)
N2—C11	1.4726 (15)	C17—H17	0.9800
C7—C8	1.5225 (18)	C18—H18A	0.9600
C7—H7A	0.9700	C18—H18B	0.9600
C7—H7B	0.9700	C18—H18C	0.9600
C8—C10	1.5214 (19)	C19—H19A	0.9600
C8—C9	1.5261 (19)	C19—H19B	0.9600
C8—H8	0.9800	C19—H19C	0.9600
C9—H9A	0.9600	C20—C21	1.5276 (17)
C9—H9B	0.9600	C20—H20A	0.9700
C9—H9C	0.9600	C20—H20B	0.9700
C10—H10A	0.9600	C21—C23	1.5172 (18)
C10—H10B	0.9600	C21—C22	1.5225 (18)
C10—H10C	0.9600	C21—H21	0.9800
C11—C12	1.5262 (17)	C22—H22A	0.9600
C11—H11A	0.9700	C22—H22B	0.9600
C11—H11B	0.9700	C22—H22C	0.9600
C12—C13	1.510 (2)	C23—H23A	0.9600
C12—C14	1.5226 (19)	C23—H23B	0.9600
C12—H12	0.9800	C23—H23C	0.9600
C13—H13A	0.9600

N1—C1—C2	123.28 (11)	H13B—C13—H13C	109.5
N1—C1—C6	116.65 (10)	C12—C14—H14A	109.5
C2—C1—C6	119.93 (10)	C12—C14—H14B	109.5
C3—C2—C1	118.68 (11)	H14A—C14—H14B	109.5
C3—C2—H2	120.7	C12—C14—H14C	109.5
C1—C2—H2	120.7	H14A—C14—H14C	109.5
C2—C3—C4	118.85 (12)	H14B—C14—H14C	109.5
C2—C3—H3	120.6	O2—C15—N3	123.68 (11)
C4—C3—H3	120.6	O2—C15—C5	116.89 (11)
C3—C4—C5	118.58 (11)	N3—C15—C5	119.40 (10)
C3—C4—H4	120.7	C15—N3—C20	124.05 (10)
C5—C4—H4	120.7	C15—N3—C16	118.27 (10)
N1—C5—C4	123.31 (11)	C20—N3—C16	117.60 (10)
N1—C5—C15	116.39 (10)	N3—C16—C17	113.20 (10)
C4—C5—C15	119.92 (10)	N3—C16—H16A	108.9
O1—C6—N2	124.00 (11)	C17—C16—H16A	108.9
O1—C6—C1	117.54 (10)	N3—C16—H16B	108.9
N2—C6—C1	118.44 (10)	C17—C16—H16B	108.9
C6—N2—C7	118.72 (10)	H16A—C16—H16B	107.8
C6—N2—C11	124.00 (10)	C18—C17—C19	111.77 (12)
C7—N2—C11	116.93 (9)	C18—C17—C16	112.09 (11)
N2—C7—C8	113.93 (10)	C19—C17—C16	108.24 (11)
N2—C7—H7A	108.8	C18—C17—H17	108.2
C8—C7—H7A	108.8	C19—C17—H17	108.2
N2—C7—H7B	108.8	C16—C17—H17	108.2
C8—C7—H7B	108.8	C17—C18—H18A	109.5
H7A—C7—H7B	107.7	C17—C18—H18B	109.5
C10—C8—C7	112.56 (10)	H18A—C18—H18B	109.5
C10—C8—C9	111.31 (12)	C17—C18—H18C	109.5
C7—C8—C9	107.08 (11)	H18A—C18—H18C	109.5
C10—C8—H8	108.6	H18B—C18—H18C	109.5
C7—C8—H8	108.6	C17—C19—H19A	109.5
C9—C8—H8	108.6	C17—C19—H19B	109.5
C8—C9—H9A	109.5	H19A—C19—H19B	109.5
C8—C9—H9B	109.5	C17—C19—H19C	109.5
H9A—C9—H9B	109.5	H19A—C19—H19C	109.5
C8—C9—H9C	109.5	H19B—C19—H19C	109.5
H9A—C9—H9C	109.5	N3—C20—C21	113.98 (10)
H9B—C9—H9C	109.5	N3—C20—H20A	108.8
C8—C10—H10A	109.5	C21—C20—H20A	108.8
C8—C10—H10B	109.5	N3—C20—H20B	108.8
H10A—C10—H10B	109.5	C21—C20—H20B	108.8
C8—C10—H10C	109.5	H20A—C20—H20B	107.7
H10A—C10—H10C	109.5	C23—C21—C22	111.16 (11)
H10B—C10—H10C	109.5	C23—C21—C20	111.30 (11)
N2—C11—C12	113.34 (9)	C22—C21—C20	107.93 (10)
N2—C11—H11A	108.9	C23—C21—H21	108.8
C12—C11—H11A	108.9	C22—C21—H21	108.8
N2—C11—H11B	108.9	C20—C21—H21	108.8
C12—C11—H11B	108.9	C21—C22—H22A	109.5
H11A—C11—H11B	107.7	C21—C22—H22B	109.5
C13—C12—C14	111.00 (12)	H22A—C22—H22B	109.5
C13—C12—C11	112.09 (11)	C21—C22—H22C	109.5
C14—C12—C11	108.62 (10)	H22A—C22—H22C	109.5
C13—C12—H12	108.3	H22B—C22—H22C	109.5
C14—C12—H12	108.3	C21—C23—H23A	109.5
C11—C12—H12	108.3	C21—C23—H23B	109.5
C12—C13—H13A	109.5	H23A—C23—H23B	109.5
C12—C13—H13B	109.5	C21—C23—H23C	109.5
H13A—C13—H13B	109.5	H23A—C23—H23C	109.5
C12—C13—H13C	109.5	H23B—C23—H23C	109.5
H13A—C13—H13C	109.5	C5—N1—C1	117.21 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2ⁱ	0.97	2.57	3.5226 (15)	166
C11—H11A···O1ⁱⁱ	0.97	2.55	3.4790 (15)	160

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

Experimental details

Crystal data
Chemical formula	C₂₃H₃₉N₃O₂
M_r	389.57
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	10.5247 (2), 17.7765 (3), 12.8773 (2)
β (°)	96.877 (2)
V (Å³)	2391.91 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.54
Crystal size (mm)	0.49 × 0.42 × 0.23

Data collection
Diffractometer	Agilent Xcalibur Atlas Gemini ultra diffractometer
Absorption correction	Analytical (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.929, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	31214, 4272, 3867
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.112, 1.05
No. of reflections	4272
No. of parameters	261
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.14

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006) and DIAMOND (Brandenburg & Putz, 2005), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2ⁱ	0.97	2.57	3.5226 (15)	166
C11—H11A···O1ⁱⁱ	0.97	2.55	3.4790 (15)	160

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

Acknowledgements

This study was supported financially by the Institutional Research Plan No. AVOZ10100521 of the Institute of Physics, the project Praemium Academiae of the Academy of Science of the Czech Republic and by the Grant Agency of Faculty of Environmental Sciences, Czech University of Life Sciences, Prague (project No. 42900/1312/3114 "Environmental Aspects of Sustainable Developement of Society") and by the Czech Ministry of Education, Youth and Sports (project MSM 6046137307).

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