4′-(4-Methyl­benzo­yl)-1′-methyl­dispiro­[indole-3(2H),2′-pyrrolidine-3′,3′′(2′′H)-indole]-2,2′′-dione

Palani, K.; Ponnuswamy, M.N.; Suresh Babu, A.R.; Raghunathan, R.; Ravikumar, K.

doi:10.1107/S1600536805039565

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4′-(4-Methylbenzoyl)-1′-methyldispiro[indole-3(2H),2′-pyrrolidine-3′,3′′(2′′H)-indole]-2,2′′-dione

K. Palani, M. N. Ponnuswamy, A. R. Suresh Babu, R. Raghunathan and K. Ravikumar

In the title compound, C₂₇H₂₃N₃O₃, the central pyrrolidine ring adopts an envelope conformation. In the crystal structure, the molecules exist as centrosymmetric N—H

O hydrogen-bonded dimers. The dimers are linked via C—H

O and C—H

π hydrogen bonds, forming a chain along the b axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039565/ci6685sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039565/ci6685Isup2.hkl Contains datablock I

CCDC reference: 296528

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.051
wR factor = 0.135
Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.58 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.22 Ratio
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H3     ...          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The spiro-pyrrolidine ring system is a frequently encountered structural motif in many pharmacologically relevant alkaloids (Cordel, 1981). It is also found in phermones, antibiotics (Gore et al., 1991) and antitumour agents (Tietz or Tietze et al., 1988; Araki et al., 2002). Several optically active pyrrolidines have been used as intermediates in controlled asymmetric syntheses (Suzuki et al., 1994). In view of this importance, the crystal structure of the title compound, (I), has been determined and the results are presented here.

A ZORTEP (Zsolnai, 1997) plot of the molecule is shown in Fig.1. The slightly longer N—C and C—C bond lengths (Table 1) in the pyrrolidine ring are due to the bulky substituents and the steric interactions between them (Seshadri et al., 2003; Abdul Ajees et al., 2002). The N2—C3 and C3—O1 bond lengths show electron delocalization over atoms N2, C3 and O2. A similar situation is also observed for atoms N3, C11 and O2. In the oxindole ring systems, the variations in endocyclic angles are due to the fusion of five- and six-membered rings (Govind et al., 2003).

The asymmetry parameters [ΔC_s(C2) = 0.065 (1); Nardelli, 1995] and puckering parameters [q₂ = 0.468 (2) Å and ϕ₂ = 225.6 (2)°; Cremer & Pople, 1975] reveal that the pyrrolidine ring adopts an envelope conformation. Atom C2 deviates from the N1/C10/C18/C26 plane by 0.698 (2) Å. The methyl group attached at N1 is in the equatorial position, as evidenced by the C1—N1—C26—C18 torsion angle of −152.44 (19)°. The benzoyl group is bisectionally attached to the pyrrolidine ring, C26—C18—C19—C20 = −175.89 (16)°.

An intramolecular C–H···π interaction involving the C12–C17 benzene ring is observed the molecular structure. In the crystal structure, symmetry-related molecules form N—H···O hydrogen-bonded dimers, which are linked via C—H···O and C—H···π hydrogen bonds (Table 2), forming a chain along the b axis (Fig. 2). In Table 2, Cg1 and Cg2 denote the centroids of the C12—C17 and C4—C9 benzene rings, respectively.

Experimental top

A mixture of (E)-3-(4'-methylphenacylidine)oxindole (1 mmol), isatin (indole-2,3-dione) (1 mmol), and sarcosine (N-methylglycine) (1 mmol) was refluxed in aqueous methonal for 3 h. On completion of the reaction the solvent was evaporated in vaccum and the resulting crude product was purified by coloumn chromatography using an n-hexane–ethylacetate mixture (7:3) as eluent. The title compound was recrystallized from a methanol–chloroform mixture (2:1 v/v).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. A view of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. The dashed line indicates a C—H···π interaction.
	Fig. 2. The crystal packing of (I), viewed approximately down the a axis. Only H atoms involved in hydrogen bonding (dashed lines) are shown.

4'-(4-Methylbenzoyl)-1'-methyldispiro[indole-3(2H),2'-pyrrolidine- 3',3''(2''H)-indole]-2,2''-dione top

Crystal data top

C₂₇H₂₃N₃O₃	Z = 2
M_r = 437.48	F(000) = 460
Triclinic, P1	D_x = 1.320 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6158 (10) Å	Cell parameters from 4387 reflections
b = 10.3812 (11) Å	θ = 2.5–28.0°
c = 11.7099 (12) Å	µ = 0.09 mm⁻¹
α = 105.047 (2)°	T = 293 K
β = 94.850 (2)°	Block, colourless
γ = 100.087 (2)°	0.20 × 0.19 × 0.19 mm
V = 1101.0 (2) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3781 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 28.0°, θ_min = 1.8°
ω scans	h = −12→9
7012 measured reflections	k = −13→13
4904 independent reflections	l = −15→13

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0665P)² + 0.1767P] where P = (F_o² + 2F_c²)/3
4904 reflections	(Δ/σ)_max = 0.001
379 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₇H₂₃N₃O₃	γ = 100.087 (2)°
M_r = 437.48	V = 1101.0 (2) Å³
Triclinic, P1	Z = 2
a = 9.6158 (10) Å	Mo Kα radiation
b = 10.3812 (11) Å	µ = 0.09 mm⁻¹
c = 11.7099 (12) Å	T = 293 K
α = 105.047 (2)°	0.20 × 0.19 × 0.19 mm
β = 94.850 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3781 reflections with I > 2σ(I)
7012 measured reflections	R_int = 0.020
4904 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.24 e Å⁻³
4904 reflections	Δρ_min = −0.15 e Å⁻³
379 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
N1	0.63714 (16)	0.30668 (15)	0.15789 (13)	0.0525 (4)
N2	0.83133 (18)	0.41969 (17)	−0.04095 (14)	0.0583 (4)
N3	1.03679 (16)	0.13138 (15)	0.13756 (12)	0.0487 (3)
O1	0.86853 (17)	0.54478 (13)	0.15471 (12)	0.0702 (4)
O2	1.09286 (13)	0.35499 (13)	0.13967 (11)	0.0584 (3)
O3	0.78470 (16)	0.27544 (17)	0.47132 (13)	0.0776 (4)
C1	0.5279 (3)	0.3641 (3)	0.1064 (2)	0.0726 (6)
C2	0.76198 (18)	0.29728 (16)	0.09513 (14)	0.0446 (4)
C3	0.83034 (19)	0.43747 (17)	0.07745 (16)	0.0516 (4)
C4	0.7751 (2)	0.2300 (2)	−0.22793 (17)	0.0637 (5)
C5	0.7237 (2)	0.0922 (3)	−0.27417 (18)	0.0678 (6)
C6	0.6779 (2)	0.0114 (2)	−0.20231 (18)	0.0609 (5)
C7	0.68232 (18)	0.06838 (18)	−0.07988 (16)	0.0508 (4)
C8	0.73532 (17)	0.20610 (16)	−0.03155 (14)	0.0443 (4)
C9	0.78111 (18)	0.28463 (18)	−0.10642 (15)	0.0499 (4)
C10	0.85935 (17)	0.25423 (15)	0.18593 (13)	0.0425 (4)
C11	1.01119 (18)	0.25840 (17)	0.15321 (13)	0.0443 (4)
C12	0.9085 (2)	−0.09739 (18)	0.14537 (16)	0.0557 (5)
C13	0.7809 (2)	−0.16624 (19)	0.16469 (17)	0.0608 (5)
C14	0.6713 (2)	−0.1001 (2)	0.19527 (17)	0.0598 (5)
C15	0.6871 (2)	0.03768 (19)	0.20708 (16)	0.0521 (4)
C16	0.81234 (17)	0.10775 (15)	0.18481 (13)	0.0418 (3)
C17	0.92243 (18)	0.04011 (16)	0.15553 (13)	0.0432 (4)
C18	0.8434 (2)	0.35721 (18)	0.30517 (14)	0.0509 (4)
C19	0.8766 (2)	0.30602 (18)	0.41338 (15)	0.0538 (4)
C20	1.0254 (2)	0.29234 (17)	0.44430 (13)	0.0505 (4)
C21	1.0476 (2)	0.1983 (2)	0.50597 (17)	0.0614 (5)
C23	1.3006 (2)	0.2573 (2)	0.50769 (17)	0.0689 (6)
C22	1.1831 (2)	0.1810 (2)	0.53583 (18)	0.0687 (6)
C24	1.2784 (3)	0.3513 (2)	0.44792 (18)	0.0700 (6)
C25	1.1430 (2)	0.3690 (2)	0.41587 (16)	0.0602 (5)
C26	0.6905 (2)	0.3781 (2)	0.28429 (17)	0.0645 (5)
C27	1.4487 (3)	0.2386 (4)	0.5434 (3)	0.1076 (10)
H27A	1.5101	0.2613	0.4880	0.161*
H27B	1.4451	0.1454	0.5429	0.161*
H27C	1.4850	0.2971	0.6222	0.161*
H1A	0.558 (3)	0.466 (3)	0.115 (2)	0.101 (8)*
H1B	0.496 (3)	0.314 (2)	0.022 (2)	0.092 (8)*
H1C	0.444 (3)	0.355 (2)	0.148 (2)	0.093 (8)*
H2	0.867 (2)	0.489 (2)	−0.069 (2)	0.075 (6)*
H3	1.118 (2)	0.1129 (19)	0.1193 (17)	0.060 (5)*
H4	0.805 (2)	0.288 (2)	−0.276 (2)	0.079 (7)*
H5	0.719 (2)	0.051 (2)	−0.357 (2)	0.076 (6)*
H6	0.640 (2)	−0.088 (2)	−0.2360 (18)	0.065 (6)*
H7	0.6460 (19)	0.0110 (19)	−0.0310 (17)	0.057 (5)*
H12	0.987 (2)	−0.1400 (19)	0.1281 (16)	0.059 (5)*
H13	0.767 (2)	−0.263 (2)	0.1568 (18)	0.068 (6)*
H14	0.581 (2)	−0.153 (2)	0.2070 (18)	0.069 (6)*
H15	0.612 (2)	0.082 (2)	0.2263 (17)	0.064 (6)*
H18	0.9127 (19)	0.4418 (19)	0.3147 (15)	0.050 (5)*
H21	0.966 (2)	0.150 (2)	0.5313 (18)	0.065 (6)*
H22	1.195 (2)	0.116 (2)	0.577 (2)	0.078 (6)*
H24	1.355 (2)	0.404 (2)	0.426 (2)	0.079 (7)*
H25	1.133 (2)	0.438 (2)	0.3731 (18)	0.063 (5)*
H26A	0.690 (2)	0.479 (2)	0.3017 (19)	0.077 (6)*
H26B	0.625 (2)	0.338 (2)	0.3344 (19)	0.069 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0574 (9)	0.0592 (9)	0.0501 (8)	0.0330 (7)	0.0130 (7)	0.0155 (6)
N2	0.0694 (10)	0.0561 (9)	0.0554 (9)	0.0133 (8)	0.0046 (7)	0.0269 (7)
N3	0.0477 (8)	0.0572 (9)	0.0493 (8)	0.0255 (7)	0.0137 (6)	0.0169 (6)
O1	0.1022 (11)	0.0426 (7)	0.0655 (8)	0.0228 (7)	−0.0002 (8)	0.0130 (6)
O2	0.0579 (8)	0.0621 (8)	0.0599 (8)	0.0093 (6)	0.0085 (6)	0.0273 (6)
O3	0.0756 (10)	0.1171 (13)	0.0607 (8)	0.0405 (9)	0.0270 (7)	0.0416 (8)
C1	0.0710 (14)	0.0875 (17)	0.0698 (14)	0.0476 (13)	0.0084 (12)	0.0201 (12)
C2	0.0516 (9)	0.0429 (8)	0.0440 (8)	0.0209 (7)	0.0063 (7)	0.0131 (6)
C3	0.0604 (11)	0.0457 (9)	0.0539 (10)	0.0217 (8)	0.0016 (8)	0.0175 (8)
C4	0.0583 (11)	0.0898 (15)	0.0473 (10)	0.0195 (10)	0.0087 (9)	0.0233 (10)
C5	0.0575 (12)	0.0956 (17)	0.0433 (10)	0.0208 (11)	0.0061 (9)	0.0037 (10)
C6	0.0481 (10)	0.0655 (12)	0.0586 (11)	0.0175 (9)	0.0008 (8)	−0.0027 (9)
C7	0.0459 (9)	0.0541 (10)	0.0522 (10)	0.0180 (8)	0.0053 (7)	0.0097 (8)
C8	0.0405 (8)	0.0511 (9)	0.0440 (8)	0.0192 (7)	0.0044 (6)	0.0120 (7)
C9	0.0460 (9)	0.0612 (11)	0.0468 (9)	0.0183 (8)	0.0042 (7)	0.0183 (8)
C10	0.0514 (9)	0.0428 (8)	0.0377 (8)	0.0193 (7)	0.0075 (7)	0.0119 (6)
C11	0.0492 (9)	0.0516 (9)	0.0350 (8)	0.0153 (7)	0.0034 (7)	0.0149 (7)
C12	0.0704 (12)	0.0514 (10)	0.0520 (10)	0.0329 (9)	0.0072 (9)	0.0131 (8)
C13	0.0817 (14)	0.0422 (10)	0.0614 (11)	0.0170 (9)	0.0019 (10)	0.0190 (8)
C14	0.0639 (12)	0.0572 (11)	0.0636 (11)	0.0114 (9)	0.0065 (9)	0.0277 (9)
C15	0.0519 (10)	0.0558 (10)	0.0579 (10)	0.0206 (8)	0.0138 (8)	0.0237 (8)
C16	0.0508 (9)	0.0426 (8)	0.0364 (7)	0.0195 (7)	0.0071 (6)	0.0118 (6)
C17	0.0514 (9)	0.0469 (9)	0.0358 (7)	0.0207 (7)	0.0060 (6)	0.0124 (6)
C18	0.0678 (11)	0.0472 (10)	0.0409 (8)	0.0258 (9)	0.0095 (8)	0.0082 (7)
C19	0.0703 (12)	0.0542 (10)	0.0396 (8)	0.0228 (9)	0.0121 (8)	0.0096 (7)
C20	0.0644 (11)	0.0539 (10)	0.0321 (8)	0.0156 (8)	0.0053 (7)	0.0082 (7)
C21	0.0658 (12)	0.0723 (13)	0.0539 (11)	0.0182 (10)	0.0120 (9)	0.0272 (9)
C23	0.0637 (12)	0.0968 (16)	0.0417 (10)	0.0176 (11)	−0.0003 (9)	0.0133 (10)
C22	0.0725 (14)	0.0878 (15)	0.0567 (11)	0.0278 (11)	0.0061 (10)	0.0327 (11)
C24	0.0646 (13)	0.0875 (15)	0.0469 (10)	−0.0053 (11)	−0.0007 (9)	0.0164 (10)
C25	0.0740 (13)	0.0593 (11)	0.0410 (9)	0.0043 (9)	−0.0022 (9)	0.0126 (8)
C26	0.0797 (14)	0.0737 (13)	0.0513 (10)	0.0476 (11)	0.0161 (10)	0.0137 (9)
C27	0.0696 (16)	0.173 (3)	0.0881 (18)	0.0309 (17)	0.0008 (13)	0.0486 (19)

Geometric parameters (Å, º) top

N1—C1	1.456 (2)	C12—C13	1.375 (3)
N1—C2	1.464 (2)	C12—C17	1.383 (2)
N1—C26	1.474 (2)	C12—H12	0.95 (2)
N2—C3	1.351 (2)	C13—C14	1.378 (3)
N2—C9	1.389 (2)	C13—H13	0.96 (2)
N2—H2	0.89 (2)	C14—C15	1.381 (3)
N3—C11	1.352 (2)	C14—H14	0.98 (2)
N3—C17	1.389 (2)	C15—C16	1.375 (2)
N3—H3	0.87 (2)	C15—H15	0.93 (2)
O1—C3	1.213 (2)	C16—C17	1.389 (2)
O2—C11	1.215 (2)	C18—C19	1.527 (2)
O3—C19	1.207 (2)	C18—C26	1.531 (3)
C1—H1A	1.02 (3)	C18—H18	0.979 (18)
C1—H1B	0.99 (3)	C19—C20	1.487 (3)
C1—H1C	0.98 (3)	C20—C25	1.381 (3)
C2—C8	1.511 (2)	C20—C21	1.390 (2)
C2—C10	1.559 (2)	C21—C22	1.375 (3)
C2—C3	1.561 (2)	C21—H21	0.96 (2)
C4—C5	1.374 (3)	C23—C24	1.375 (3)
C4—C9	1.380 (3)	C23—C22	1.378 (3)
C4—H4	0.95 (2)	C23—C27	1.509 (3)
C5—C6	1.381 (3)	C22—H22	0.94 (2)
C5—H5	0.95 (2)	C24—C25	1.381 (3)
C6—C7	1.395 (3)	C24—H24	0.93 (2)
C6—H6	0.99 (2)	C25—H25	0.98 (2)
C7—C8	1.378 (2)	C26—H26A	1.02 (2)
C7—H7	0.971 (19)	C26—H26B	1.01 (2)
C8—C9	1.392 (2)	C27—H27A	0.96
C10—C16	1.505 (2)	C27—H27B	0.96
C10—C11	1.537 (2)	C27—H27C	0.96
C10—C18	1.560 (2)

C1—N1—C2	115.72 (15)	C12—C13—C14	121.24 (17)
C1—N1—C26	113.69 (15)	C12—C13—H13	120.0 (12)
C2—N1—C26	106.97 (14)	C14—C13—H13	118.8 (12)
C3—N2—C9	112.11 (15)	C13—C14—C15	120.50 (19)
C3—N2—H2	121.0 (14)	C13—C14—H14	118.9 (12)
C9—N2—H2	126.7 (14)	C15—C14—H14	120.5 (12)
C11—N3—C17	112.96 (14)	C16—C15—C14	119.23 (17)
C11—N3—H3	121.2 (13)	C16—C15—H15	120.1 (12)
C17—N3—H3	125.8 (13)	C14—C15—H15	120.6 (12)
N1—C1—H1A	113.9 (15)	C15—C16—C17	119.55 (15)
N1—C1—H1B	111.0 (14)	C15—C16—C10	131.74 (14)
H1A—C1—H1B	110 (2)	C17—C16—C10	108.71 (14)
N1—C1—H1C	109.5 (15)	C12—C17—C16	121.64 (17)
H1A—C1—H1C	105 (2)	C12—C17—N3	129.36 (15)
H1B—C1—H1C	107 (2)	C16—C17—N3	108.98 (14)
N1—C2—C8	116.46 (14)	C19—C18—C26	114.89 (16)
N1—C2—C10	99.79 (12)	C19—C18—C10	112.14 (13)
C8—C2—C10	115.90 (12)	C26—C18—C10	103.46 (14)
N1—C2—C3	111.53 (12)	C19—C18—H18	107.4 (10)
C8—C2—C3	101.67 (13)	C26—C18—H18	111.0 (10)
C10—C2—C3	111.97 (13)	C10—C18—H18	107.7 (10)
O1—C3—N2	125.84 (17)	O3—C19—C20	120.72 (16)
O1—C3—C2	126.54 (16)	O3—C19—C18	121.26 (17)
N2—C3—C2	107.50 (15)	C20—C19—C18	118.01 (15)
C5—C4—C9	117.5 (2)	C25—C20—C21	118.26 (18)
C5—C4—H4	122.7 (14)	C25—C20—C19	123.46 (16)
C9—C4—H4	119.8 (14)	C21—C20—C19	118.28 (17)
C4—C5—C6	121.42 (19)	C22—C21—C20	120.5 (2)
C4—C5—H5	119.8 (13)	C22—C21—H21	121.2 (12)
C6—C5—H5	118.8 (13)	C20—C21—H21	118.2 (12)
C5—C6—C7	120.44 (19)	C24—C23—C22	117.9 (2)
C5—C6—H6	121.2 (12)	C24—C23—C27	121.6 (2)
C7—C6—H6	118.3 (12)	C22—C23—C27	120.5 (2)
C8—C7—C6	119.00 (18)	C21—C22—C23	121.4 (2)
C8—C7—H7	121.4 (11)	C21—C22—H22	118.6 (14)
C6—C7—H7	119.5 (11)	C23—C22—H22	120.0 (14)
C7—C8—C9	119.10 (16)	C23—C24—C25	121.6 (2)
C7—C8—C2	132.56 (15)	C23—C24—H24	120.3 (14)
C9—C8—C2	108.29 (14)	C25—C24—H24	118.2 (14)
C4—C9—N2	127.20 (17)	C24—C25—C20	120.35 (19)
C4—C9—C8	122.51 (18)	C24—C25—H25	118.1 (12)
N2—C9—C8	110.29 (15)	C20—C25—H25	121.5 (12)
C16—C10—C11	102.30 (12)	N1—C26—C18	106.12 (13)
C16—C10—C2	112.98 (13)	N1—C26—H26A	110.8 (12)
C11—C10—C2	111.81 (12)	C18—C26—H26A	110.1 (13)
C16—C10—C18	113.14 (13)	N1—C26—H26B	107.8 (12)
C11—C10—C18	116.54 (14)	C18—C26—H26B	113.4 (12)
C2—C10—C18	100.56 (12)	H26A—C26—H26B	108.6 (17)
O2—C11—N3	125.46 (16)	C23—C27—H27A	109.5
O2—C11—C10	127.45 (15)	C23—C27—H27B	109.5
N3—C11—C10	107.05 (14)	H27A—C27—H27B	109.5
C13—C12—C17	117.79 (17)	C23—C27—H27C	109.5
C13—C12—H12	122.5 (11)	H27A—C27—H27C	109.5
C17—C12—H12	119.7 (11)	H27B—C27—H27C	109.5

C1—N1—C2—C8	−62.7 (2)	C18—C10—C11—N3	124.07 (14)
C26—N1—C2—C8	169.46 (14)	C17—C12—C13—C14	−1.1 (3)
C1—N1—C2—C10	171.77 (17)	C12—C13—C14—C15	0.1 (3)
C26—N1—C2—C10	43.95 (16)	C13—C14—C15—C16	1.8 (3)
C1—N1—C2—C3	53.3 (2)	C14—C15—C16—C17	−2.5 (2)
C26—N1—C2—C3	−74.49 (16)	C14—C15—C16—C10	177.72 (16)
C9—N2—C3—O1	179.98 (17)	C11—C10—C16—C15	179.72 (17)
C9—N2—C3—C2	−3.7 (2)	C2—C10—C16—C15	−59.9 (2)
N1—C2—C3—O1	53.9 (2)	C18—C10—C16—C15	53.5 (2)
C8—C2—C3—O1	178.67 (17)	C11—C10—C16—C17	−0.04 (16)
C10—C2—C3—O1	−57.0 (2)	C2—C10—C16—C17	120.32 (14)
N1—C2—C3—N2	−122.37 (15)	C18—C10—C16—C17	−126.23 (15)
C8—C2—C3—N2	2.42 (16)	C13—C12—C17—C16	0.3 (3)
C10—C2—C3—N2	126.77 (14)	C13—C12—C17—N3	−178.00 (16)
C9—C4—C5—C6	0.9 (3)	C15—C16—C17—C12	1.5 (2)
C4—C5—C6—C7	0.2 (3)	C10—C16—C17—C12	−178.68 (14)
C5—C6—C7—C8	−1.1 (3)	C15—C16—C17—N3	−179.85 (14)
C6—C7—C8—C9	0.8 (2)	C10—C16—C17—N3	−0.05 (17)
C6—C7—C8—C2	−176.32 (16)	C11—N3—C17—C12	178.62 (16)
N1—C2—C8—C7	−61.6 (2)	C11—N3—C17—C16	0.14 (18)
C10—C2—C8—C7	55.4 (2)	C16—C10—C18—C19	36.3 (2)
C3—C2—C8—C7	177.03 (17)	C11—C10—C18—C19	−81.93 (19)
N1—C2—C8—C9	121.07 (15)	C2—C10—C18—C19	157.04 (15)
C10—C2—C8—C9	−122.01 (15)	C16—C10—C18—C26	−88.11 (17)
C3—C2—C8—C9	−0.35 (16)	C11—C10—C18—C26	153.69 (15)
C5—C4—C9—N2	178.71 (17)	C2—C10—C18—C26	32.66 (17)
C5—C4—C9—C8	−1.1 (3)	C26—C18—C19—O3	5.2 (3)
C3—N2—C9—C4	−176.23 (17)	C10—C18—C19—O3	−112.55 (19)
C3—N2—C9—C8	3.6 (2)	C26—C18—C19—C20	−175.90 (16)
C7—C8—C9—C4	0.3 (3)	C10—C18—C19—C20	66.3 (2)
C2—C8—C9—C4	178.06 (16)	O3—C19—C20—C25	−154.50 (18)
C7—C8—C9—N2	−179.60 (14)	C18—C19—C20—C25	26.6 (2)
C2—C8—C9—N2	−1.81 (18)	O3—C19—C20—C21	25.0 (3)
N1—C2—C10—C16	74.44 (15)	C18—C19—C20—C21	−153.94 (17)
C8—C2—C10—C16	−51.46 (18)	C25—C20—C21—C22	−1.0 (3)
C3—C2—C10—C16	−167.45 (13)	C19—C20—C21—C22	179.49 (18)
N1—C2—C10—C11	−170.79 (12)	C20—C21—C22—C23	1.1 (3)
C8—C2—C10—C11	63.31 (18)	C24—C23—C22—C21	−0.3 (3)
C3—C2—C10—C11	−52.68 (17)	C27—C23—C22—C21	178.8 (2)
N1—C2—C10—C18	−46.44 (15)	C22—C23—C24—C25	−0.5 (3)
C8—C2—C10—C18	−172.34 (14)	C27—C23—C24—C25	−179.6 (2)
C3—C2—C10—C18	71.66 (16)	C23—C24—C25—C20	0.5 (3)
C17—N3—C11—O2	−178.02 (15)	C21—C20—C25—C24	0.2 (3)
C17—N3—C11—C10	−0.16 (17)	C19—C20—C25—C24	179.69 (17)
C16—C10—C11—O2	177.92 (15)	C1—N1—C26—C18	−152.49 (19)
C2—C10—C11—O2	56.7 (2)	C2—N1—C26—C18	−23.5 (2)
C18—C10—C11—O2	−58.1 (2)	C19—C18—C26—N1	−129.77 (17)
C16—C10—C11—N3	0.12 (15)	C10—C18—C26—N1	−7.2 (2)
C2—C10—C11—N3	−121.06 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.90 (2)	1.99 (2)	2.879 (2)	170 (2)
C13—H13···O1ⁱⁱ	0.97 (2)	2.37 (2)	3.232 (2)	149 (2)
C7—H7···Cg1	0.98 (2)	2.87 (2)	3.551 (3)	128 (1)
C12—H12···Cg2ⁱⁱⁱ	0.95 (2)	2.75 (2)	3.613 (3)	153 (1)

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

Experimental details

Crystal data
Chemical formula	C₂₇H₂₃N₃O₃
M_r	437.48
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.6158 (10), 10.3812 (11), 11.7099 (12)
α, β, γ (°)	105.047 (2), 94.850 (2), 100.087 (2)
V (Å³)	1101.0 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.19 × 0.19

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7012, 4904, 3781
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.135, 1.01
No. of reflections	4904
No. of parameters	379
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.15

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997), PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

N1—C1	1.456 (2)	O1—C3	1.213 (2)
N1—C2	1.464 (2)	O2—C11	1.215 (2)
N1—C26	1.474 (2)	O3—C19	1.207 (2)
N2—C3	1.351 (2)	C2—C10	1.559 (2)
N2—C9	1.389 (2)	C10—C18	1.560 (2)
N3—C11	1.352 (2)	C18—C26	1.531 (3)
N3—C17	1.389 (2)

C1—N1—C2	115.72 (15)	C8—C2—C10	115.90 (12)
C1—N1—C26	113.69 (15)	C11—C10—C18	116.54 (14)
C2—N1—C26	106.97 (14)	C2—C10—C18	100.56 (12)
N1—C2—C10	99.79 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.90 (2)	1.99 (2)	2.879 (2)	170 (2)
C13—H13···O1ⁱⁱ	0.97 (2)	2.37 (2)	3.232 (2)	149 (2)
C7—H7···Cg1	0.98 (2)	2.87 (2)	3.551 (3)	128 (1)
C12—H12···Cg2ⁱⁱⁱ	0.95 (2)	2.75 (2)	3.613 (3)	153 (1)

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

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