N-(1-Adamantyl)-4-hydroxy-2-(2-methyl­propyl)-2-oxo-1,2-di­hydro­quinoline-3-carbox­amide

Shishkina, S.V.; Shishkin, O.V.; Ukrainets, I.V.; Amer, M.; Sidorenko, L.V.

doi:10.1107/S1600536801005591

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N-(1-Adamantyl)-4-hydroxy-2-(2-methylpropyl)-2-oxo-1,2-dihydroquinoline-3-carboxamide

S. V. Shishkina, O. V. Shishkin, I. V. Ukrainets, M. Amer and L. V. Sidorenko

In the title compound, C₂₄H₃₀N₂O₃·0.5C₃H₈O, the formation of intramolecular O—H

O and N—H

O hydrogen bonds causes considerable changes in the bond lengths within the amidopyridine fragment. This fact probably results in the unusual reactivity of the ether group in this type of compound.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801005591/om6005sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801005591/om6005Isup2.hkl Contains datablock I

CCDC reference: 165651

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
Disorder in solvent or counterion
R factor = 0.069
wR factor = 0.212
Data-to-parameter ratio = 23.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



PLAT_701  Alert B Bond    Calc    1.562(9), Rep    1.537(5), Dev.      2.78 Sigma
                     C2S  -C1SB    3.567   1.555


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           30.08
         From the CIF: _reflns_number_total               6505
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         6995
         Completeness (_total/calc)             92.99%
          Alert C: < 95% complete

WEIGH_01  Alert C Extra text has been found in the
          _refine_ls_weighting_scheme field. This should be in the
          _refine_ls_weighting_details field.
          Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.0991P)^2^] wher
          Weighting scheme identified as calc

PLAT_202  Alert C  Isotropic non-H Atoms in Anion/Solvent     =          1

PLAT_302  Alert C Anion/Solvent Disorder .......................      43.00 Perc.

PLAT_701  Alert C Bond    Calc   1.537(17), Rep    1.562(5), Dev.      1.47 Sigma
                     C2S  -C1SA    3.567   1.555

PLAT_711  Alert C BOND    Unknown or Inconsistent Label ........       O1SA
                           O1SA   C2S

PLAT_711  Alert C BOND    Unknown or Inconsistent Label ........       O1SA
                           C2S    O1SA

PLAT_712  Alert C ANGLE   Unknown or Inconsistent Label ........       O1SA
                           O1SA   C2S    C1SB

PLAT_712  Alert C ANGLE   Unknown or Inconsistent Label ........       O1SA
                           O1SA   C2S    C1SB

PLAT_712  Alert C ANGLE   Unknown or Inconsistent Label ........       O1SA
                           O1SA   C2S    C1SA

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           30.08
         From the CIF: _reflns_number_total               6505
         From the CIF: _diffrn_reflns_limit_ max hkl   20.    0.   15.
         From the CIF: _diffrn_reflns_limit_ min hkl  -21.  -19.    0.
         TEST1: Expected hkl limits for theta max
         Calculated maximum hkl   21.   19.   17.
         Calculated minimum hkl  -21.  -19.  -17.
          ALERT: Expected hkl max differ from CIF values


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 10 Alert Level C = Please check

Comment top

Earlier, we demonstrated that intramolecular hydrogen bonds in the ethyl ethers of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid results in the marked lengthening of the C═O bond of the 3-carboethoxy group (Ukrainets et al., 2000). This fact, probably, determines an unusual reactivity of these compounds. A similar situation is observed for heteryl (Shishkina et al., 2000) and arylalkyl (Ukrainets et al., 2000) amides of this acid. In this paper, we report results of the X-ray diffraction study of the adamantyl-1-amide of 1-isobutyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid, (I).

The quinolone fragment and the C10, O1, O3, C14, O2, N2 and C15 atoms are coplanar within 0.04 Å. The isopropyl group of the alkyl substituent at the N1 atom is arranged nearly orthogonal with respect to the pyridone ring [the C5—N1—C10—C11 torsion angle is -79.1 (2)°] and has an +ac orientation relatively to the N1—C10 bond (the N1—C10—C11—H11 torsion angle is 64.3°). It should be noted some difference between values of the C—C bonds within isopropyl group. The C11—C12 bond [1.553 (4) Å] is longer than the C11—C13 bond [1.540 (4) Å].

The adamantane fragment is arranged with respect to the amide group in such a way that the C14—N2 and C16—C15 bonds have an ap orientation [the C14—N2—C15—C16 torsion angle is 178.9 (2)°]. Repulsion between the bulky adamantane substituent and the carbonyl group, probably, causes some elongation of the N2—C15 bond [1.489 (3) Å] with respect to its mean value 1.469 Å (Burgi & Dunitz, 1994).

The formation of the N2—H2N···O1 and O3—H3O···O2 intramolecular hydrogen bonds (H2N···O1 1.98 Å, N2—H2N···O1 138°; H3O···O2 1.75 Å and O3—H3O···O2 148°) results in an elongation of the O1—C6, O2—C14, C7—C8 and C7—C14 bonds (Table 1) compared with their mean values of 1.210, 1.330 and 1.465 Å (Burgi & Dunitz, 1994), respectively.

The presence of shortened intramolecular contacts O1···H10A = 2.29 Å (the van der Waals radii sum is 2.45 Å; Zefirov & Zorky, 1995), H10B···C4 = 2.66 Å (2.87 Å), H10B···H4 = 2.17 Å (2.32 Å), H11.·C4 = 2.82 Å, H11···H4 = 2.25 Å, probably causes the elongation of the N1—C5, N1—C6 and N1—C10 bonds (mean values are 1.371, 1.355 and 1.469 Å, respectively).

In the crystal phase, compound (I) exists as the solvate with 2-propanol in a 2:1 ratio. The molecules of the solvent are disordered over two positions with equal populations with respect to the centre of symmetry.

Experimental top

Crystals of (I) were grown by slow evaporation from an 2-propanol solution.

Computing details top

Data collection: P3 (Siemens, 1989); cell refinement: P3; data reduction: XDISK (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1991); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. View of the title compound. The non-H atoms are shown with displacement ellipsoids drawn at the 50% probability level and H atoms have been omitted for clarity.

N-(1-Adamantyl)-4-hydroxy-2-(2-methylpropyl)-2-oxo-1,2-dihydroquinoline-3- carboxamide top

Crystal data top

C₂₄H₃₀N₂O₃·0.5C₃H₈O	F(000) = 916
M_r = 424.55	D_x = 1.185 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.140 (4) Å	Cell parameters from 24 reflections
b = 13.655 (3) Å	θ = 10–11°
c = 12.286 (3) Å	µ = 0.08 mm⁻¹
β = 110.51 (3)°	T = 293 K
V = 2379 (1) Å³	Needles, colourless
Z = 4	0.40 × 0.20 × 0.20 mm

Data collection top

Siemens P3/PC diffractometer	R_int = 0.038
Radiation source: fine-focus sealed tube	θ_max = 30.1°, θ_min = 2.1°
Graphite monochromator	h = −21→20
θ–2θ scans	k = −19→0
6801 measured reflections	l = 0→15
6505 independent reflections	2 standard reflections every 98 reflections
2175 reflections with I > 2σ(I)	intensity decay: 5%

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)] = 0.069	Hydrogen site location: difference Fourier map
wR(F²) = 0.212	H-atom parameters constrained
S = 0.91	Calculated w = 1/[σ²(F_o²) + (0.0991P)²] where P = (F_o² + 2F_c²)/3
6505 reflections	(Δ/σ)_max = 0.042
280 parameters	Δρ_max = 0.41 e Å⁻³
3 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₄H₃₀N₂O₃·0.5C₃H₈O	V = 2379 (1) Å³
M_r = 424.55	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.140 (4) Å	µ = 0.08 mm⁻¹
b = 13.655 (3) Å	T = 293 K
c = 12.286 (3) Å	0.40 × 0.20 × 0.20 mm
β = 110.51 (3)°

Data collection top

Siemens P3/PC diffractometer	R_int = 0.038
6801 measured reflections	2 standard reflections every 98 reflections
6505 independent reflections	intensity decay: 5%
2175 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.069	3 restraints
wR(F²) = 0.212	H-atom parameters constrained
S = 0.91	Δρ_max = 0.41 e Å⁻³
6505 reflections	Δρ_min = −0.27 e Å⁻³
280 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	−0.14254 (12)	1.07656 (12)	1.04873 (16)	0.0479 (5)
N2	−0.29127 (12)	0.80550 (14)	0.92103 (17)	0.0558 (5)
H2N	−0.3186	0.8616	0.9139	0.067*
O1	−0.28282 (10)	1.00092 (11)	0.94872 (16)	0.0654 (5)
O2	−0.15162 (10)	0.72237 (11)	1.00499 (13)	0.0598 (5)
O3	−0.00378 (10)	0.80816 (11)	1.12200 (14)	0.0603 (5)
H3O	−0.0398	0.7623	1.0950	0.090*
C1	0.09968 (15)	0.97757 (19)	1.20844 (19)	0.0561 (6)
H1	0.1299	0.9172	1.2252	0.067*
C2	0.15016 (17)	1.0624 (2)	1.2483 (2)	0.0618 (7)
H2	0.2143	1.0595	1.2916	0.074*
C3	0.10377 (16)	1.1536 (2)	1.2226 (2)	0.0602 (7)
H3	0.1378	1.2108	1.2496	0.072*
C4	0.00752 (16)	1.15955 (18)	1.1573 (2)	0.0550 (6)
H4	−0.0218	1.2204	1.1410	0.066*
C5	−0.04576 (14)	1.07287 (16)	1.11575 (18)	0.0456 (5)
C6	−0.19718 (15)	0.99120 (16)	1.00735 (19)	0.0476 (5)
C7	−0.14824 (14)	0.89628 (16)	1.03338 (18)	0.0459 (5)
C8	−0.05199 (15)	0.89248 (16)	1.09774 (17)	0.0452 (5)
C9	0.00149 (15)	0.98192 (17)	1.14186 (18)	0.0462 (5)
C10	−0.19022 (16)	1.17321 (17)	1.0127 (2)	0.0558 (6)
H10A	−0.2473	1.1629	0.9462	0.067*
H10B	−0.1491	1.2150	0.9878	0.067*
C11	−0.21649 (17)	1.22776 (18)	1.1074 (2)	0.0650 (7)
H11	−0.1581	1.2445	1.1710	0.078*
C12	−0.26767 (19)	1.3245 (2)	1.0548 (3)	0.0878 (9)
H12A	−0.2283	1.3623	1.0241	0.132*
H12B	−0.2803	1.3614	1.1143	0.132*
H12C	−0.3260	1.3095	0.9936	0.132*
C13	−0.2777 (2)	1.1649 (3)	1.1574 (3)	0.0903 (9)
H13A	−0.2942	1.2024	1.2135	0.135*
H13B	−0.2429	1.1078	1.1941	0.135*
H13C	−0.3340	1.1452	1.0957	0.135*
C14	−0.19831 (15)	0.80273 (17)	0.98503 (18)	0.0479 (5)
C15	−0.35104 (14)	0.72114 (16)	0.86153 (19)	0.0484 (6)
C16	−0.45272 (15)	0.76266 (19)	0.8021 (2)	0.0643 (7)
H16A	−0.4749	0.7908	0.8603	0.077*
H16B	−0.4522	0.8138	0.7476	0.077*
C17	−0.51946 (16)	0.6788 (2)	0.7374 (2)	0.0716 (8)
H17	−0.5831	0.7053	0.7003	0.086*
C18	−0.48559 (17)	0.6358 (2)	0.6436 (2)	0.0755 (8)
H18A	−0.4850	0.6863	0.5883	0.091*
H18B	−0.5281	0.5842	0.6019	0.091*
C19	−0.38528 (17)	0.5941 (2)	0.7023 (2)	0.0655 (7)
H19	−0.3633	0.5658	0.6430	0.079*
C20	−0.31711 (15)	0.67719 (18)	0.7672 (2)	0.0549 (6)
H20A	−0.2539	0.6512	0.8029	0.066*
H20B	−0.3155	0.7278	0.7126	0.066*
C21	−0.35384 (17)	0.64023 (18)	0.9482 (2)	0.0585 (6)
H21A	−0.3749	0.6678	1.0076	0.070*
H21B	−0.2911	0.6136	0.9858	0.070*
C22	−0.42213 (18)	0.55736 (19)	0.8827 (2)	0.0661 (7)
H22	−0.4236	0.5062	0.9380	0.079*
C23	−0.38620 (19)	0.51380 (19)	0.7910 (3)	0.0704 (7)
H23A	−0.4268	0.4603	0.7512	0.085*
H23B	−0.3230	0.4881	0.8284	0.085*
C24	−0.52204 (18)	0.5996 (2)	0.8240 (3)	0.0794 (9)
H24A	−0.5650	0.5478	0.7840	0.095*
H24B	−0.5444	0.6273	0.8824	0.095*
O1S	−0.0781 (5)	0.4599 (7)	0.9098 (7)	0.196 (3)*	0.50
C1SA	0.0538 (14)	0.5971 (9)	1.011 (3)	0.308 (10)*	0.50
H1S1	0.0917	0.5949	0.9624	0.461*	0.50
H1S2	0.0938	0.6068	1.0902	0.461*	0.50
H1S3	0.0096	0.6501	0.9865	0.461*	0.50
C1SB	−0.0243 (8)	0.5845 (6)	0.9085 (8)	0.160 (4)*	0.50
H1S4	−0.0915	0.5902	0.8729	0.240*	0.50
H1S5	0.0025	0.5702	0.8500	0.240*	0.50
H1S6	0.0013	0.6450	0.9463	0.240*	0.50
C2S	0.0000	0.5000	1.0000	0.204 (4)*
H2SB	0.0384	0.4720	0.9603	0.306*	0.50
H2SA	−0.0384	0.5280	1.0397	0.306*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0475 (11)	0.0407 (11)	0.0516 (11)	−0.0010 (8)	0.0127 (9)	−0.0081 (8)
N2	0.0487 (11)	0.0405 (11)	0.0662 (12)	−0.0027 (9)	0.0052 (9)	−0.0075 (9)
O1	0.0440 (9)	0.0490 (10)	0.0880 (13)	0.0034 (7)	0.0040 (8)	−0.0133 (9)
O2	0.0555 (9)	0.0487 (10)	0.0610 (10)	0.0015 (8)	0.0026 (8)	0.0005 (8)
O3	0.0551 (9)	0.0472 (10)	0.0648 (11)	0.0016 (8)	0.0038 (8)	0.0071 (8)
C1	0.0464 (13)	0.0681 (17)	0.0427 (12)	−0.0024 (11)	0.0019 (10)	0.0017 (11)
C2	0.0481 (13)	0.084 (2)	0.0445 (13)	−0.0094 (14)	0.0053 (11)	−0.0054 (13)
C3	0.0532 (14)	0.0757 (19)	0.0536 (14)	−0.0220 (13)	0.0210 (12)	−0.0156 (13)
C4	0.0584 (14)	0.0515 (15)	0.0571 (13)	−0.0087 (11)	0.0226 (12)	−0.0105 (11)
C5	0.0455 (12)	0.0541 (14)	0.0385 (11)	−0.0046 (10)	0.0164 (10)	−0.0047 (10)
C6	0.0455 (12)	0.0468 (14)	0.0466 (12)	−0.0008 (11)	0.0111 (10)	−0.0104 (10)
C7	0.0470 (12)	0.0458 (13)	0.0400 (11)	−0.0065 (10)	0.0093 (10)	−0.0057 (10)
C8	0.0511 (13)	0.0466 (14)	0.0348 (11)	0.0029 (11)	0.0115 (10)	0.0037 (9)
C9	0.0458 (12)	0.0575 (14)	0.0335 (11)	−0.0029 (11)	0.0114 (9)	−0.0016 (10)
C10	0.0554 (13)	0.0434 (13)	0.0607 (14)	−0.0032 (11)	0.0106 (11)	−0.0040 (11)
C11	0.0524 (13)	0.0592 (16)	0.0790 (17)	0.0006 (12)	0.0176 (12)	−0.0165 (14)
C12	0.0704 (17)	0.0661 (19)	0.121 (3)	0.0171 (15)	0.0255 (17)	−0.0074 (17)
C13	0.101 (2)	0.085 (2)	0.101 (2)	−0.0087 (18)	0.0553 (19)	−0.0143 (18)
C14	0.0486 (12)	0.0465 (14)	0.0417 (12)	−0.0001 (11)	0.0072 (10)	0.0006 (10)
C15	0.0438 (11)	0.0454 (13)	0.0491 (13)	−0.0064 (10)	0.0077 (10)	−0.0067 (10)
C16	0.0452 (13)	0.0629 (16)	0.0764 (17)	0.0061 (12)	0.0108 (12)	−0.0035 (14)
C17	0.0393 (13)	0.0793 (19)	0.0813 (19)	−0.0031 (13)	0.0026 (13)	−0.0074 (16)
C18	0.0621 (16)	0.0829 (19)	0.0641 (17)	−0.0255 (14)	0.0003 (13)	−0.0115 (15)
C19	0.0627 (15)	0.0713 (18)	0.0607 (15)	−0.0131 (13)	0.0193 (12)	−0.0248 (14)
C20	0.0476 (12)	0.0582 (15)	0.0538 (13)	−0.0069 (11)	0.0115 (11)	0.0018 (11)
C21	0.0613 (15)	0.0613 (16)	0.0521 (14)	−0.0027 (12)	0.0189 (12)	−0.0007 (12)
C22	0.0674 (16)	0.0617 (16)	0.0709 (17)	−0.0149 (13)	0.0267 (13)	0.0072 (13)
C23	0.0693 (16)	0.0518 (16)	0.0872 (19)	−0.0135 (13)	0.0236 (14)	−0.0119 (14)
C24	0.0580 (16)	0.085 (2)	0.098 (2)	−0.0214 (14)	0.0305 (15)	−0.0124 (18)

Geometric parameters (Å, º) top

N1—C5	1.408 (3)	C11—C12	1.553 (4)
N1—C6	1.417 (3)	C15—C21	1.545 (3)
N1—C10	1.495 (3)	C15—C20	1.544 (3)
N2—C14	1.351 (3)	C15—C16	1.561 (3)
N2—C15	1.489 (2)	C16—C17	1.549 (3)
O1—C6	1.250 (3)	C17—C24	1.528 (4)
O2—C14	1.282 (3)	C17—C18	1.534 (4)
O3—C8	1.340 (2)	C18—C19	1.544 (4)
C1—C2	1.380 (3)	C19—C23	1.550 (4)
C1—C9	1.425 (3)	C19—C20	1.553 (3)
C2—C3	1.410 (4)	C21—C22	1.554 (4)
C3—C4	1.398 (3)	C22—C23	1.532 (4)
C4—C5	1.423 (3)	C22—C24	1.541 (4)
C5—C9	1.413 (3)	O1SA—C2S	1.417 (4)
C6—C7	1.472 (3)	C1SA—C2S	1.537 (5)
C7—C8	1.394 (3)	C1SB—C2S	1.562 (5)
C7—C14	1.498 (3)	C2Sⁱ—O1SA	1.417 (5)
C8—C9	1.461 (3)	C2Sⁱ—C1SB	1.537 (5)
C10—C11	1.546 (3)	C2Sⁱ—C1SA	1.562 (5)
C11—C13	1.540 (4)

C5—N1—C6	122.53 (17)	O2—C14—C7	119.07 (18)
C5—N1—C10	120.03 (17)	N2—C14—C7	119.09 (19)
C6—N1—C10	117.35 (17)	N2—C15—C21	111.95 (18)
C14—N2—C15	126.45 (18)	N2—C15—C20	111.37 (18)
C2—C1—C9	120.4 (2)	C21—C15—C20	109.62 (19)
C1—C2—C3	119.5 (2)	N2—C15—C16	106.19 (17)
C4—C3—C2	121.1 (2)	C21—C15—C16	108.74 (18)
C3—C4—C5	120.3 (2)	C20—C15—C16	108.85 (19)
N1—C5—C9	120.31 (18)	C17—C16—C15	109.31 (19)
N1—C5—C4	121.5 (2)	C24—C17—C18	110.4 (2)
C9—C5—C4	118.14 (19)	C24—C17—C16	109.7 (2)
O1—C6—N1	118.47 (19)	C18—C17—C16	109.8 (2)
O1—C6—C7	124.08 (19)	C17—C18—C19	108.9 (2)
N1—C6—C7	117.42 (18)	C18—C19—C23	109.9 (2)
C8—C7—C6	120.18 (19)	C18—C19—C20	109.8 (2)
C8—C7—C14	118.45 (19)	C23—C19—C20	108.9 (2)
C6—C7—C14	121.24 (18)	C15—C20—C19	109.48 (18)
O3—C8—C7	122.54 (19)	C15—C21—C22	109.8 (2)
O3—C8—C9	116.62 (18)	C23—C22—C24	110.1 (2)
C7—C8—C9	120.84 (19)	C23—C22—C21	108.7 (2)
C5—C9—C1	120.7 (2)	C24—C22—C21	109.6 (2)
C5—C9—C8	118.68 (18)	C22—C23—C19	109.6 (2)
C1—C9—C8	120.6 (2)	C17—C24—C22	109.28 (19)
N1—C10—C11	115.3 (2)	O1SAⁱ—C2S—C1SB	101.5 (5)
C13—C11—C10	112.4 (2)	O1SAⁱ—C2S—C1SB	101.5 (5)
C13—C11—C12	111.0 (2)	C1SBⁱ—C2S—C1SA	126.2 (10)
C10—C11—C12	108.6 (2)	O1SA—C2S—C1SA	132.2 (10)
O2—C14—N2	121.84 (19)	C1SBⁱ—C2S—C1SA	126.2 (10)

C9—C1—C2—C3	0.1 (3)	C15—N2—C14—C7	176.7 (2)
C1—C2—C3—C4	−0.1 (3)	C8—C7—C14—O2	0.6 (3)
C2—C3—C4—C5	0.3 (3)	C6—C7—C14—O2	176.4 (2)
C6—N1—C5—C9	1.7 (3)	C8—C7—C14—N2	−179.0 (2)
C10—N1—C5—C9	−174.70 (19)	C6—C7—C14—N2	−3.2 (3)
C6—N1—C5—C4	−179.4 (2)	C14—N2—C15—C20	−62.7 (3)
C10—N1—C5—C4	4.2 (3)	C14—N2—C15—C21	60.4 (3)
C3—C4—C5—N1	−179.30 (19)	C14—N2—C15—C16	178.9 (2)
C3—C4—C5—C9	−0.3 (3)	N2—C15—C16—C17	179.7 (2)
C5—N1—C6—O1	179.74 (19)	C20—C15—C16—C17	59.7 (3)
C10—N1—C6—O1	−3.8 (3)	C21—C15—C16—C17	−59.7 (3)
C5—N1—C6—C7	−2.1 (3)	C15—C16—C17—C24	60.8 (3)
C10—N1—C6—C7	174.33 (19)	C15—C16—C17—C18	−60.7 (3)
O1—C6—C7—C8	178.8 (2)	C24—C17—C18—C19	−60.4 (3)
N1—C6—C7—C8	0.8 (3)	C16—C17—C18—C19	60.7 (3)
O1—C6—C7—C14	3.1 (3)	C17—C18—C19—C23	59.2 (3)
N1—C6—C7—C14	−174.91 (19)	C17—C18—C19—C20	−60.5 (3)
C6—C7—C8—O3	−178.76 (19)	N2—C15—C20—C19	−176.31 (18)
C14—C7—C8—O3	−2.9 (3)	C21—C15—C20—C19	59.3 (2)
C6—C7—C8—C9	1.0 (3)	C16—C15—C20—C19	−59.6 (2)
C14—C7—C8—C9	176.79 (19)	C18—C19—C20—C15	60.5 (3)
N1—C5—C9—C1	179.23 (19)	C23—C19—C20—C15	−59.8 (3)
C4—C5—C9—C1	0.3 (3)	N2—C15—C21—C22	176.34 (19)
N1—C5—C9—C8	0.2 (3)	C20—C15—C21—C22	−59.6 (2)
C4—C5—C9—C8	−178.81 (19)	C16—C15—C21—C22	59.3 (2)
C2—C1—C9—C5	−0.1 (3)	C15—C21—C22—C23	60.5 (3)
C2—C1—C9—C8	178.9 (2)	C15—C21—C22—C24	−60.0 (3)
O3—C8—C9—C5	178.27 (19)	C24—C22—C23—C19	58.7 (3)
C7—C8—C9—C5	−1.5 (3)	C21—C22—C23—C19	−61.4 (3)
O3—C8—C9—C1	−0.8 (3)	C18—C19—C23—C22	−58.9 (3)
C7—C8—C9—C1	179.46 (19)	C20—C19—C23—C22	61.4 (3)
C5—N1—C10—C11	−79.1 (2)	C18—C17—C24—C22	60.3 (3)
C6—N1—C10—C11	104.3 (2)	C16—C17—C24—C22	−60.9 (3)
N1—C10—C11—C13	−55.2 (3)	C23—C22—C24—C17	−59.3 (3)
N1—C10—C11—C12	−178.3 (2)	C21—C22—C24—C17	60.3 (3)
C15—N2—C14—O2	−2.9 (4)

Symmetry code: (i) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1	0.86	1.98	2.687 (2)	138
O3—H3O···O2	0.82	1.75	2.489 (2)	148

Experimental details

Crystal data
Chemical formula	C₂₄H₃₀N₂O₃·0.5C₃H₈O
M_r	424.55
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.140 (4), 13.655 (3), 12.286 (3)
β (°)	110.51 (3)
V (Å³)	2379 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Siemens P3/PC diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6801, 6505, 2175
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.212, 0.91
No. of reflections	6505
No. of parameters	280
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.27

Computer programs: P3 (Siemens, 1989), P3, XDISK (Siemens, 1991), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1991), SHELXL97.

Selected bond lengths (Å) top

N1—C5	1.408 (3)	O2—C14	1.282 (3)
N1—C6	1.417 (3)	O3—C8	1.340 (2)
N1—C10	1.495 (3)	C6—C7	1.472 (3)
N2—C14	1.351 (3)	C7—C8	1.394 (3)
N2—C15	1.489 (2)	C7—C14	1.498 (3)
O1—C6	1.250 (3)	C8—C9	1.461 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1	0.86	1.98	2.687 (2)	138.3
O3—H3O···O2	0.82	1.75	2.489 (2)	148.3

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