5,5-Di­methyl-3-[(5-phenyl-1H-pyrazol-3-yl)­amino]­cyclo­hex-2-en-1-one

Quesada, A.; Cannon, D.; Quiroga, J.; Insuasty, B.; Abonia, R.; Mejía, D.; Cobo, J.; Nogueras, M.; Sánchez, A.; Low, J.N.

doi:10.1107/S1600536801001702

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5,5-Dimethyl-3-[(5-phenyl-1H-pyrazol-3-yl)amino]cyclohex-2-en-1-one

A. Quesada, D. Cannon, J. Quiroga, B. Insuasty, R. Abonia, D. Mejía, J. Cobo, M. Nogueras, A. Sánchez and J. N. Low

The title compound, C₁₇H₁₉N₃O, crystallizes with two molecules in the asymmetric unit. These molecules are hydrogen bonded intra- and intermolecularly via strong and weak hydrogen bonds to form a complex three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801001702/na6045sup1.cif Contains datablocks global, 1
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801001702/na6045Isup2.hkl Contains datablock I

CCDC reference: 159763

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.004 Å
R factor = 0.052
wR factor = 0.123
Data-to-parameter ratio = 9.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.112

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.48
         From the CIF: _reflns_number_total               3597
         Count of symmetry unique reflns         3608
         Completeness (_total/calc)             99.70%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

The title compound, (I), was an intermediate in the prepararation of pyrazolo[3,4-b]quinolin-5-ones. Geometric parameters are given in Table 1 and a view of each individual molecule is given in Fig. 1.

The primary supramolecular structures are a C(9) motif, (Bernstein et al., 1995). involving only molecule 1, N133—H133···O11ⁱⁱ [symmetry code: (ii) x, y - 1, z]. A similar chain perpendicular to the first is formed by molecule 2 and its symmetry-related molecules by the C(9) motif, N233—H233···O21ⁱⁱⁱ [symmetry code: (iii) x - 1/2, -y + 1/2, 1 + z]. These chains are then interlinked by further hydrogen bonds, N131—H131···O21ⁱ and N231—H231···O11, which links the two molecules in the asymmetric unit [symmetry code: (i) 1 - x, 1 - y, z + 1/2]. These along with two weak C—H···N hydrogen bonds combine to form a complex three-dimensional network. The details of the hydrogen bonding is given in Table 2.

Examination of the structure with PLATON (Spek, 2000) showed that there were no solvent-accessible voids in the crystal lattice.

The high R_int value is due to slight interference from one or more small crystallites that it was not possible to remove from the main crystal.

Experimental top

A solution of 5-amino-3-phenylpyrazole (1 mmol) and dimedone (1 mmol) in 15 ml of absolute ethanol was heated to reflux for 25 min. The title compound appeared as a solid which was filtered off and washed with ethanol, dried and recrystallized from ethanol affording yellow crystals suitable for X-ray diffraction; yield 80%.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Figures top

	Fig. 1. A view of molecule 1 with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of molecule 2 with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

5,5-Dimethyl-3-[(5-phenyl-1H-pyrazol-3-yl)amino]cyclohex-2-en-1-one top

Crystal data top

C₁₇H₁₉N₃O	D_x = 1.230 Mg m⁻³
M_r = 281.35	Melting point: 502 K
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
a = 19.0427 (2) Å	Cell parameters from 2770 reflections
b = 9.6024 (4) Å	θ = 2.1–25.0°
c = 16.6135 (7) Å	µ = 0.08 mm⁻¹
V = 3037.87 (18) Å³	T = 150 K
Z = 8	Plate, colourless
F(000) = 1200	0.38 × 0.18 × 0.08 mm

Data collection top

KappaCCD diffractometer	3597 independent reflections
Radiation source: fine-focus sealed X-ray tube	2776 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.112
ϕ and ω scans with κ offsets	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −24→24
T_min = 0.971, T_max = 0.994	k = −11→12
19777 measured reflections	l = −20→21

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0707P)²] where P = (F_o² + 2F_c²)/3
3597 reflections	(Δ/σ)_max = 0.010
383 parameters	Δρ_max = 0.28 e Å⁻³
1 restraint	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₇H₁₉N₃O	V = 3037.87 (18) Å³
M_r = 281.35	Z = 8
Orthorhombic, Pna2₁	Mo Kα radiation
a = 19.0427 (2) Å	µ = 0.08 mm⁻¹
b = 9.6024 (4) Å	T = 150 K
c = 16.6135 (7) Å	0.38 × 0.18 × 0.08 mm

Data collection top

KappaCCD diffractometer	3597 independent reflections
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	2776 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.994	R_int = 0.112
19777 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	1 restraint
wR(F²) = 0.123	H-atom parameters constrained
S = 0.99	Δρ_max = 0.28 e Å⁻³
3597 reflections	Δρ_min = −0.25 e Å⁻³
383 parameters

Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	U_iso*/U_eq
O11	0.43205 (11)	0.9588 (2)	0.35740 (13)	0.0273 (5)
C11	0.39797 (16)	0.8887 (3)	0.40828 (17)	0.0232 (6)
C12	0.40734 (16)	0.7438 (3)	0.41596 (18)	0.0226 (6)
C13	0.37079 (16)	0.6666 (3)	0.47159 (18)	0.0218 (6)
N131	0.37156 (13)	0.5258 (2)	0.47312 (15)	0.0241 (5)
C131	0.39220 (15)	0.4387 (3)	0.40949 (17)	0.0209 (6)
N132	0.40434 (13)	0.3058 (2)	0.42599 (15)	0.0220 (5)
N133	0.41568 (13)	0.2471 (2)	0.35219 (15)	0.0226 (6)
C134	0.41072 (16)	0.3413 (3)	0.29241 (18)	0.0220 (6)
C135	0.39547 (16)	0.4671 (3)	0.32706 (19)	0.0267 (7)
C136	0.41849 (17)	0.3049 (3)	0.20609 (19)	0.0251 (7)
C137	0.4437 (2)	0.4051 (3)	0.1532 (2)	0.0359 (8)
C138	0.4502 (2)	0.3747 (4)	0.0724 (2)	0.0390 (8)
C139	0.43195 (19)	0.2459 (4)	0.0441 (2)	0.0351 (8)
C140	0.40623 (19)	0.1452 (4)	0.0958 (2)	0.0359 (8)
C141	0.39987 (18)	0.1756 (3)	0.1777 (2)	0.0304 (7)
C14	0.32420 (16)	0.7331 (3)	0.53332 (18)	0.0244 (7)
C15	0.33307 (16)	0.8909 (3)	0.54219 (18)	0.0255 (7)
C151	0.39773 (19)	0.9228 (4)	0.5944 (2)	0.0366 (8)
C152	0.26719 (19)	0.9511 (4)	0.5812 (2)	0.0391 (8)
C16	0.34300 (17)	0.9583 (3)	0.45944 (18)	0.0265 (7)
O21	0.69341 (10)	0.6159 (2)	0.10657 (12)	0.0266 (5)
C21	0.66100 (15)	0.6801 (3)	0.16107 (17)	0.0219 (6)
C22	0.58770 (15)	0.6998 (3)	0.15888 (19)	0.0229 (6)
C23	0.55399 (15)	0.7785 (3)	0.21568 (18)	0.0209 (6)
N231	0.48568 (13)	0.8134 (2)	0.21422 (15)	0.0232 (5)
N232	0.37032 (13)	0.8184 (3)	0.16981 (15)	0.0244 (5)
N233	0.33641 (13)	0.8079 (3)	0.09820 (15)	0.0254 (6)
C231	0.43769 (15)	0.7993 (3)	0.15071 (18)	0.0218 (6)
C24	0.59347 (16)	0.8389 (3)	0.28614 (19)	0.0247 (7)
C25	0.66017 (16)	0.7600 (3)	0.30760 (19)	0.0260 (7)
C251	0.6420 (2)	0.6184 (3)	0.3448 (2)	0.0377 (8)
C252	0.70371 (18)	0.8460 (4)	0.3665 (2)	0.0364 (8)
C26	0.70245 (18)	0.7395 (4)	0.23038 (19)	0.0305 (7)
C235	0.44743 (16)	0.7757 (3)	0.06796 (18)	0.0236 (7)
C234	0.38061 (15)	0.7818 (3)	0.03598 (19)	0.0230 (6)
C236	0.35724 (17)	0.7682 (3)	−0.04747 (18)	0.0239 (7)
C237	0.40750 (18)	0.7598 (4)	−0.1087 (2)	0.0327 (8)
C238	0.38757 (19)	0.7458 (4)	−0.1882 (2)	0.0351 (8)
C239	0.31734 (19)	0.7380 (3)	−0.2083 (2)	0.0327 (8)
C240	0.26703 (17)	0.7467 (3)	−0.1487 (2)	0.0323 (7)
C241	0.28650 (17)	0.7621 (3)	−0.06840 (19)	0.0277 (7)
H12	0.4399	0.6980	0.3816	0.027*
H131	0.3579	0.4852	0.5180	0.029*
H133	0.4251	0.1583	0.3446	0.027*
H135	0.3886	0.5540	0.3010	0.032*
H137	0.4564	0.4947	0.1727	0.043*
H138	0.4674	0.4434	0.0362	0.047*
H139	0.4370	0.2254	−0.0115	0.042*
H140	0.3930	0.0563	0.0758	0.043*
H141	0.3827	0.1068	0.2138	0.037*
H14B	0.3335	0.6891	0.5861	0.029*
H14D	0.2747	0.7133	0.5191	0.029*
H15E	0.4060	1.0235	0.5953	0.055*
H15F	0.4389	0.8756	0.5719	0.055*
H15G	0.3895	0.8896	0.6494	0.055*
H15H	0.2715	1.0526	0.5847	0.059*
H15I	0.2617	0.9121	0.6353	0.059*
H15J	0.2261	0.9272	0.5485	0.059*
H16A	0.2976	0.9562	0.4303	0.032*
H16B	0.3562	1.0572	0.4671	0.032*
H22	0.5611	0.6575	0.1171	0.027*
H231	0.4689	0.8499	0.2589	0.028*
H233	0.2907	0.8171	0.0927	0.031*
H24C	0.5621	0.8398	0.3337	0.030*
H24D	0.6059	0.9366	0.2736	0.030*
H25B	0.6854	0.5676	0.3567	0.056*
H25F	0.6136	0.5645	0.3067	0.056*
H25G	0.6155	0.6326	0.3946	0.056*
H25H	0.6780	0.8560	0.4173	0.055*
H25I	0.7126	0.9383	0.3435	0.055*
H25J	0.7485	0.7989	0.3767	0.055*
H26A	0.7221	0.8306	0.2138	0.037*
H26B	0.7424	0.6767	0.2420	0.037*
H235	0.4903	0.7593	0.0403	0.028*
H237	0.4560	0.7638	−0.0954	0.039*
H238	0.4223	0.7415	−0.2291	0.042*
H239	0.3037	0.7267	−0.2629	0.039*
H240	0.2187	0.7423	−0.1626	0.039*
H241	0.2515	0.7684	−0.0278	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O11	0.0321 (12)	0.0237 (10)	0.0261 (11)	−0.0025 (9)	0.0069 (9)	0.0007 (9)
C11	0.0300 (17)	0.0257 (15)	0.0140 (14)	−0.0001 (13)	−0.0024 (12)	−0.0019 (11)
C12	0.0253 (16)	0.0248 (15)	0.0176 (15)	0.0024 (12)	0.0024 (12)	−0.0020 (11)
C13	0.0254 (16)	0.0251 (15)	0.0148 (13)	0.0026 (13)	−0.0022 (12)	−0.0003 (11)
N131	0.0323 (15)	0.0258 (13)	0.0143 (11)	−0.0005 (11)	0.0031 (11)	0.0001 (10)
C131	0.0228 (15)	0.0203 (14)	0.0197 (15)	−0.0008 (11)	−0.0019 (11)	0.0002 (12)
N132	0.0200 (13)	0.0234 (12)	0.0225 (13)	0.0008 (10)	0.0002 (10)	−0.0027 (11)
N133	0.0251 (14)	0.0222 (13)	0.0205 (13)	0.0012 (10)	0.0011 (11)	−0.0028 (10)
C134	0.0220 (16)	0.0232 (15)	0.0209 (15)	−0.0020 (12)	0.0025 (12)	−0.0023 (12)
C135	0.0344 (18)	0.0221 (15)	0.0237 (15)	−0.0006 (13)	0.0023 (12)	0.0012 (12)
C136	0.0281 (18)	0.0256 (15)	0.0215 (15)	0.0030 (13)	0.0017 (12)	−0.0001 (12)
C137	0.051 (2)	0.0284 (17)	0.0279 (18)	−0.0068 (15)	0.0043 (15)	0.0006 (14)
C138	0.051 (2)	0.041 (2)	0.0246 (17)	−0.0066 (17)	0.0050 (15)	0.0056 (15)
C139	0.043 (2)	0.042 (2)	0.0212 (16)	0.0069 (15)	−0.0003 (15)	−0.0023 (13)
C140	0.047 (2)	0.0320 (18)	0.0291 (18)	0.0004 (15)	−0.0023 (15)	−0.0079 (15)
C141	0.039 (2)	0.0263 (16)	0.0262 (17)	0.0002 (14)	0.0028 (13)	−0.0030 (13)
C14	0.0282 (17)	0.0296 (16)	0.0156 (14)	−0.0001 (13)	0.0017 (12)	−0.0001 (12)
C15	0.0298 (17)	0.0274 (16)	0.0194 (15)	0.0014 (13)	0.0030 (13)	−0.0025 (12)
C151	0.048 (2)	0.036 (2)	0.0252 (17)	−0.0056 (15)	−0.0048 (15)	−0.0060 (14)
C152	0.048 (2)	0.0367 (18)	0.0324 (18)	0.0099 (16)	0.0150 (16)	0.0005 (15)
C16	0.0313 (17)	0.0238 (15)	0.0244 (16)	0.0035 (13)	0.0055 (13)	0.0023 (12)
O21	0.0198 (11)	0.0402 (13)	0.0199 (10)	0.0047 (9)	−0.0008 (8)	−0.0060 (9)
C21	0.0204 (15)	0.0270 (15)	0.0184 (14)	0.0004 (12)	0.0009 (12)	0.0003 (12)
C22	0.0211 (15)	0.0277 (15)	0.0198 (14)	−0.0008 (13)	−0.0008 (12)	−0.0030 (12)
C23	0.0182 (15)	0.0226 (14)	0.0220 (15)	−0.0012 (12)	0.0007 (11)	0.0028 (12)
N231	0.0219 (13)	0.0290 (13)	0.0187 (12)	0.0021 (10)	0.0002 (10)	−0.0037 (10)
N232	0.0179 (13)	0.0326 (13)	0.0225 (13)	−0.0004 (11)	−0.0008 (10)	0.0006 (11)
N233	0.0160 (13)	0.0377 (15)	0.0226 (13)	−0.0023 (11)	0.0013 (10)	−0.0013 (11)
C231	0.0197 (16)	0.0252 (14)	0.0205 (15)	−0.0003 (12)	−0.0009 (12)	−0.0010 (12)
C24	0.0244 (16)	0.0288 (16)	0.0208 (15)	−0.0004 (12)	−0.0009 (12)	−0.0052 (12)
C25	0.0254 (17)	0.0331 (17)	0.0195 (16)	0.0045 (13)	−0.0018 (12)	−0.0028 (12)
C251	0.049 (2)	0.0369 (19)	0.0267 (17)	0.0098 (16)	−0.0016 (16)	0.0052 (14)
C252	0.0316 (19)	0.051 (2)	0.0262 (17)	0.0056 (15)	−0.0068 (14)	−0.0105 (15)
C26	0.0231 (17)	0.0470 (19)	0.0215 (17)	0.0029 (14)	−0.0026 (13)	−0.0016 (13)
C235	0.0175 (15)	0.0289 (16)	0.0245 (16)	0.0014 (12)	0.0012 (12)	−0.0015 (12)
C234	0.0184 (16)	0.0247 (15)	0.0258 (16)	0.0002 (12)	0.0006 (13)	−0.0018 (13)
C236	0.0215 (16)	0.0271 (15)	0.0232 (16)	−0.0003 (12)	−0.0021 (12)	0.0014 (12)
C237	0.0202 (17)	0.053 (2)	0.0250 (17)	−0.0031 (14)	0.0007 (14)	0.0004 (14)
C238	0.0292 (19)	0.052 (2)	0.0238 (17)	0.0026 (16)	0.0037 (14)	0.0000 (15)
C239	0.037 (2)	0.0409 (19)	0.0204 (16)	−0.0004 (15)	−0.0036 (14)	0.0014 (14)
C240	0.0218 (17)	0.0445 (19)	0.0307 (18)	−0.0019 (14)	−0.0052 (14)	0.0034 (15)
C241	0.0222 (16)	0.0350 (17)	0.0260 (16)	0.0006 (13)	−0.0020 (13)	0.0025 (13)

Geometric parameters (Å, º) top

O11—C11	1.260 (4)	O21—C21	1.257 (3)
C11—C12	1.409 (4)	C21—C22	1.409 (4)
C11—C16	1.505 (4)	C21—C26	1.508 (4)
C12—C13	1.374 (4)	C22—C23	1.369 (4)
C12—H12	0.9500	C22—H22	0.9500
C13—N131	1.353 (4)	C23—N231	1.344 (4)
C13—C14	1.499 (4)	C23—C24	1.507 (4)
N131—C131	1.404 (4)	N231—C231	1.402 (4)
N131—H131	0.8800	N231—H231	0.8800
C131—N132	1.325 (4)	N232—C231	1.334 (4)
C131—C135	1.398 (4)	N232—N233	1.357 (3)
N132—N133	1.367 (4)	N233—C234	1.356 (4)
N133—C134	1.347 (4)	N233—H233	0.8800
N133—H133	0.8800	C231—C235	1.405 (4)
C134—C135	1.369 (4)	C24—C25	1.521 (4)
C134—C136	1.483 (4)	C24—H24C	0.9900
C135—H135	0.9500	C24—H24D	0.9900
C136—C141	1.375 (5)	C25—C252	1.526 (4)
C136—C137	1.389 (5)	C25—C251	1.532 (5)
C137—C138	1.380 (5)	C25—C26	1.527 (5)
C137—H137	0.9500	C251—H25B	0.9800
C138—C139	1.367 (5)	C251—H25F	0.9800
C138—H138	0.9500	C251—H25G	0.9800
C139—C140	1.383 (5)	C252—H25H	0.9800
C139—H139	0.9500	C252—H25I	0.9800
C140—C141	1.397 (5)	C252—H25J	0.9800
C140—H140	0.9500	C26—H26A	0.9900
C141—H141	0.9500	C26—H26B	0.9900
C14—C15	1.531 (4)	C235—C234	1.380 (4)
C14—H14B	0.9900	C235—H235	0.9500
C14—H14D	0.9900	C234—C236	1.462 (4)
C15—C152	1.525 (4)	C236—C241	1.392 (4)
C15—C16	1.531 (4)	C236—C237	1.399 (4)
C15—C151	1.537 (4)	C237—C238	1.381 (5)
C151—H15E	0.9800	C237—H237	0.9500
C151—H15F	0.9800	C238—C239	1.381 (5)
C151—H15G	0.9800	C238—H238	0.9500
C152—H15H	0.9800	C239—C240	1.380 (5)
C152—H15I	0.9800	C239—H239	0.9500
C152—H15J	0.9800	C240—C241	1.393 (5)
C16—H16A	0.9900	C240—H240	0.9500
C16—H16B	0.9900	C241—H241	0.9500

O11—C11—C12	121.5 (3)	O21—C21—C22	122.3 (3)
O11—C11—C16	120.0 (3)	O21—C21—C26	118.6 (3)
C12—C11—C16	118.4 (3)	C22—C21—C26	119.2 (3)
C13—C12—C11	122.0 (3)	C23—C22—C21	121.4 (3)
C13—C12—H12	119.0	C23—C22—H22	119.3
C11—C12—H12	119.0	C21—C22—H22	119.3
N131—C13—C12	123.1 (3)	N231—C23—C22	125.4 (3)
N131—C13—C14	114.8 (3)	N231—C23—C24	113.6 (3)
C12—C13—C14	122.0 (3)	C22—C23—C24	120.9 (3)
C13—N131—C131	125.8 (2)	C23—N231—C231	128.3 (3)
C13—N131—H131	117.1	C23—N231—H231	115.8
C131—N131—H131	117.1	C231—N231—H231	115.8
N132—C131—C135	112.5 (3)	C231—N232—N233	103.8 (2)
N132—C131—N131	117.8 (3)	N232—N233—C234	112.7 (2)
C135—C131—N131	129.4 (3)	N232—N233—H233	123.6
C131—N132—N133	103.8 (2)	C234—N233—H233	123.6
C134—N133—N132	111.9 (2)	N232—C231—N231	115.7 (3)
C134—N133—H133	124.0	N232—C231—C235	112.4 (3)
N132—N133—H133	124.0	N231—C231—C235	131.7 (3)
N133—C134—C135	107.3 (3)	C23—C24—C25	114.0 (3)
N133—C134—C136	123.2 (3)	C23—C24—H24C	108.8
C135—C134—C136	129.5 (3)	C25—C24—H24C	108.8
C134—C135—C131	104.5 (3)	C23—C24—H24D	108.8
C134—C135—H135	127.8	C25—C24—H24D	108.8
C131—C135—H135	127.8	H24C—C24—H24D	107.6
C141—C136—C137	119.9 (3)	C24—C25—C252	109.5 (3)
C141—C136—C134	121.3 (3)	C24—C25—C251	110.4 (3)
C137—C136—C134	118.9 (3)	C252—C25—C251	110.1 (3)
C138—C137—C136	120.0 (3)	C24—C25—C26	107.9 (3)
C138—C137—H137	120.0	C252—C25—C26	108.8 (3)
C136—C137—H137	120.0	C251—C25—C26	110.1 (3)
C139—C138—C137	120.2 (3)	C25—C251—H25B	109.5
C139—C138—H138	119.9	C25—C251—H25F	109.5
C137—C138—H138	119.9	H25B—C251—H25F	109.5
C138—C139—C140	120.6 (3)	C25—C251—H25G	109.5
C138—C139—H139	119.7	H25B—C251—H25G	109.5
C140—C139—H139	119.7	H25F—C251—H25G	109.5
C139—C140—C141	119.3 (3)	C25—C252—H25H	109.5
C139—C140—H140	120.3	C25—C252—H25I	109.5
C141—C140—H140	120.3	H25H—C252—H25I	109.5
C136—C141—C140	120.0 (3)	C25—C252—H25J	109.5
C136—C141—H141	120.0	H25H—C252—H25J	109.5
C140—C141—H141	120.0	H25I—C252—H25J	109.5
C13—C14—C15	115.0 (2)	C21—C26—C25	114.5 (3)
C13—C14—H14B	108.5	C21—C26—H26A	108.6
C15—C14—H14B	108.5	C25—C26—H26A	108.6
C13—C14—H14D	108.5	C21—C26—H26B	108.6
C15—C14—H14D	108.5	C25—C26—H26B	108.6
H14B—C14—H14D	107.5	H26A—C26—H26B	107.6
C152—C15—C16	108.8 (3)	C234—C235—C231	104.4 (3)
C152—C15—C14	109.0 (3)	C234—C235—H235	127.8
C16—C15—C14	110.2 (2)	C231—C235—H235	127.8
C152—C15—C151	110.1 (3)	N233—C234—C235	106.6 (3)
C16—C15—C151	108.9 (3)	N233—C234—C236	123.4 (3)
C14—C15—C151	109.9 (3)	C235—C234—C236	129.9 (3)
C15—C151—H15E	109.5	C241—C236—C237	118.6 (3)
C15—C151—H15F	109.5	C241—C236—C234	122.4 (3)
H15E—C151—H15F	109.5	C237—C236—C234	119.1 (3)
C15—C151—H15G	109.5	C238—C237—C236	120.9 (3)
H15E—C151—H15G	109.5	C238—C237—H237	119.6
H15F—C151—H15G	109.5	C236—C237—H237	119.6
C15—C152—H15H	109.5	C237—C238—C239	120.2 (3)
C15—C152—H15I	109.5	C237—C238—H238	119.9
H15H—C152—H15I	109.5	C239—C238—H238	119.9
C15—C152—H15J	109.5	C240—C239—C238	119.7 (3)
H15H—C152—H15J	109.5	C240—C239—H239	120.2
H15I—C152—H15J	109.5	C238—C239—H239	120.2
C11—C16—C15	113.9 (2)	C239—C240—C241	120.6 (3)
C11—C16—H16A	108.8	C239—C240—H240	119.7
C15—C16—H16A	108.8	C241—C240—H240	119.7
C11—C16—H16B	108.8	C236—C241—C240	120.1 (3)
C15—C16—H16B	108.8	C236—C241—H241	120.0
H16A—C16—H16B	107.7	C240—C241—H241	120.0

O11—C11—C12—C13	179.6 (3)	O21—C21—C22—C23	−175.2 (3)
C16—C11—C12—C13	−3.8 (4)	C26—C21—C22—C23	3.9 (4)
C11—C12—C13—N131	170.8 (3)	C21—C22—C23—N231	173.5 (3)
C11—C12—C13—C14	−6.4 (5)	C21—C22—C23—C24	−4.3 (4)
C12—C13—N131—C131	−18.0 (5)	C22—C23—N231—C231	−11.7 (5)
C14—C13—N131—C131	159.4 (3)	C24—C23—N231—C231	166.2 (3)
C13—N131—C131—N132	165.7 (3)	C231—N232—N233—C234	0.6 (3)
C13—N131—C131—C135	−21.6 (5)	N233—N232—C231—N231	176.3 (2)
C135—C131—N132—N133	0.0 (3)	N233—N232—C231—C235	−0.4 (3)
N131—C131—N132—N133	173.8 (2)	C23—N231—C231—N232	168.2 (3)
C131—N132—N133—C134	0.1 (3)	C23—N231—C231—C235	−15.9 (5)
N132—N133—C134—C135	−0.1 (3)	N231—C23—C24—C25	157.6 (3)
N132—N133—C134—C136	−178.0 (3)	C22—C23—C24—C25	−24.3 (4)
N133—C134—C135—C131	0.1 (3)	C23—C24—C25—C252	167.9 (3)
C136—C134—C135—C131	177.8 (3)	C23—C24—C25—C251	−70.7 (3)
N132—C131—C135—C134	0.0 (4)	C23—C24—C25—C26	49.6 (3)
N131—C131—C135—C134	−173.0 (3)	O21—C21—C26—C25	−155.8 (3)
N133—C134—C136—C141	30.0 (5)	C22—C21—C26—C25	25.1 (4)
C135—C134—C136—C141	−147.5 (3)	C24—C25—C26—C21	−50.2 (4)
N133—C134—C136—C137	−151.5 (3)	C252—C25—C26—C21	−169.0 (3)
C135—C134—C136—C137	31.1 (5)	C251—C25—C26—C21	70.3 (3)
C141—C136—C137—C138	−0.2 (5)	N232—C231—C235—C234	0.2 (3)
C134—C136—C137—C138	−178.8 (3)	N231—C231—C235—C234	−175.9 (3)
C136—C137—C138—C139	0.0 (6)	N232—N233—C234—C235	−0.5 (3)
C137—C138—C139—C140	0.6 (6)	N232—N233—C234—C236	−179.0 (3)
C138—C139—C140—C141	−0.9 (5)	C231—C235—C234—N233	0.2 (3)
C137—C136—C141—C140	−0.1 (5)	C231—C235—C234—C236	178.6 (3)
C134—C136—C141—C140	178.5 (3)	N233—C234—C236—C241	−9.0 (5)
C139—C140—C141—C136	0.6 (5)	C235—C234—C236—C241	172.9 (3)
N131—C13—C14—C15	169.4 (3)	N233—C234—C236—C237	171.5 (3)
C12—C13—C14—C15	−13.1 (4)	C235—C234—C236—C237	−6.6 (5)
C13—C14—C15—C152	159.2 (3)	C241—C236—C237—C238	0.0 (5)
C13—C14—C15—C16	39.9 (3)	C234—C236—C237—C238	179.5 (3)
C13—C14—C15—C151	−80.1 (3)	C236—C237—C238—C239	−0.8 (6)
O11—C11—C16—C15	−150.5 (3)	C237—C238—C239—C240	1.1 (6)
C12—C11—C16—C15	32.8 (4)	C238—C239—C240—C241	−0.6 (5)
C152—C15—C16—C11	−168.9 (3)	C237—C236—C241—C240	0.5 (5)
C14—C15—C16—C11	−49.5 (4)	C234—C236—C241—C240	−179.0 (3)
C151—C15—C16—C11	71.0 (3)	C239—C240—C241—C236	−0.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N131—H131···O21ⁱ	0.88	2.02	2.881 (3)	167
N133—H133···O11ⁱⁱ	0.88	1.93	2.788 (3)	164
N233—H233···O21ⁱⁱⁱ	0.88	1.98	2.825 (3)	162
N231—H231···O11	0.88	2.07	2.942 (4)	173
C237—H237···N133^iv	0.95	2.59	3.430 (4)	147
C240—H240···N133^v	0.95	2.57	3.479 (4)	160

Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) x, y−1, z; (iii) x−1/2, −y+3/2, z; (iv) −x+1, −y+1, z−1/2; (v) −x+1/2, y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉N₃O
M_r	281.35
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	150
a, b, c (Å)	19.0427 (2), 9.6024 (4), 16.6135 (7)
V (Å³)	3037.87 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.38 × 0.18 × 0.08

Data collection
Diffractometer	KappaCCD diffractometer
Absorption correction	Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)
T_min, T_max	0.971, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	19777, 3597, 2776
R_int	0.112
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.123, 0.99
No. of reflections	3597
No. of parameters	383
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.25

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and PLATON (Spek, 2000), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top

C13—N131	1.353 (4)	N231—C231	1.402 (4)
N131—C131	1.404 (4)	N232—C231	1.334 (4)
C131—N132	1.325 (4)	N232—N233	1.357 (3)
N132—N133	1.367 (4)	N233—C234	1.356 (4)
N133—C134	1.347 (4)

C13—N131—C131	125.8 (2)	C23—N231—C231	128.3 (3)
C131—N132—N133	103.8 (2)	C231—N232—N233	103.8 (2)
C134—N133—N132	111.9 (2)	N232—N233—C234	112.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N131—H131···O21ⁱ	0.88	2.02	2.881 (3)	167
N133—H133···O11ⁱⁱ	0.88	1.93	2.788 (3)	164
N233—H233···O21ⁱⁱⁱ	0.88	1.98	2.825 (3)	162
N231—H231···O11	0.88	2.07	2.942 (4)	173
C237—H237···N133^iv	0.95	2.59	3.430 (4)	147
C240—H240···N133^v	0.95	2.57	3.479 (4)	160

Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) x, y−1, z; (iii) x−1/2, −y+3/2, z; (iv) −x+1, −y+1, z−1/2; (v) −x+1/2, y+1/2, z−1/2.

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