N-(4a-Morpholino-2,3,4,4a,9,9a-hexa­hydro-1H-xanthen-9-yl)­phenyl­amine

Bhaskaran, S.; Selvanayagam, S.; Velmurugan, D.; Ravikumar, K.; Anniyappan, M.; Muralidharan, D.; Perumal, P.T.

doi:10.1107/S1600536803017173

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N-(4a-Morpholino-2,3,4,4a,9,9a-hexahydro-1H-xanthen-9-yl)phenylamine

S. Bhaskaran, S. Selvanayagam, D. Velmurugan, K. Ravikumar, M. Anniyappan, D. Muralidharan and P. T. Perumal

In the title compound, C₂₃H₂₈N₂O₂, the pyran ring in the xanthene moiety adopts a half-chair conformation. The molecular structure is influenced by intramolecular N—H

N and C—H

O hydrogen bonds and the crystal structure is stabilized by C—H

O and C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803017173/ci6248sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803017173/ci6248Isup2.hkl Contains datablock I

CCDC reference: 222863

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.068
wR factor = 0.179
Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .....       0.97

Alert level B
CELLV02_ALERT_1_B  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 4
            Calculated cell volume su =      13.00
            Cell volume su given      =      18.00
DIFMX01_ALERT_2_B  The maximum difference density is > 0.1*ZMAX*1.00
            _refine_diff_density_max given =      0.966
            Test value =      0.800
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ..........       0.97 e/A   3  

Alert level C
DIFMX02_ALERT_1_C  The minimum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ..       2.79
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ...          ?

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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

An X-ray study of the title compound, (I), was of interest because xanthene derivatives have been well documented as biogenic precursors (Vinod & Gupta, 1979) and neuroleptic (Lassen et al., 1980) and antiallergic (Pfister, 1980) agents. They possess antiviral activity (Carr et al., 1976). These derivatives act as a potent human CCRI receptor antagonists (Naya et al., 2003).

In the title molecule (Fig. 1), bond lengths in the aromatic rings (C and E), the cyclohexane ring (A) and the morpholine ring (D) have normal values (Allen et al., 1987). The geometry of the pyran ring in the xanthene moiety (Table 1) is comparable to that observed in other xanthene derivatives (Jeyakanthan et al., 1999; Miao et al., 1996). The sum of the bond angles around N15 of 337.2 (2)° is indicative of sp³ character of the atom. The aromatic rings E and C are almost perpendicular to each other with a dihedral angle of 85.5 (1)°. The pyran ring in the xanthene moiety adopts a half-chair conformation with asymmetry parameter DC₂(C7—C2) = 0.003 (1) (Nardelli, 1983). The cyclohexane ring (A) and the morpholine ring (D) both adopt chair conformations. The molecular structure is influenced by weak N—H···N and C—H···O hydrogen bonds. The crystal structure is stabilized by C—H···O interactions and C—H···π interactions involving the symmetry-related aromatic ring C (Table 2 and Fig. 2).

Experimental top

A solution of 0.3 g of cyclohexanone, 0.27 g of morpholine and catalytic amount of InCl₃ in 20 ml of acetonitrile was refluxed for 3 h. The reaction mixture was cooled to room temperature under a nitrogen atmosphere and 0.6 g of o-hydroxybenzylideneaniline was added. The reaction mixture was stirred at ambient temperature for 20 min. After completion of the reaction, the reaction mixture was quenched by addition of water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na₂SO₄, filtered and concentrated under vacuum. The crude crystalline product was recrystallized using ethyl acetate to yield the title compound. The melting point of the title compound is 429–431 K.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1990)'; software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of title compound, showing 30% probability displacement ellipsoids. H atoms have been omitted for clarity.
	Fig. 2. The packing of the molecules, viewed down the a axis.

N-(4a-Morpholino-2,3,4,4a,9,9a-hexahydro-1H-xanthen-9-yl)phenylamine top

Crystal data top

C₂₃H₂₈N₂O₂	Z = 2
M_r = 364.47	F(000) = 392
Triclinic, P1	D_x = 1.254 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6452 (7) Å	Cell parameters from 2317 reflections
b = 10.1247 (8) Å	θ = 2.4–27.2°
c = 11.1168 (9) Å	µ = 0.08 mm⁻¹
α = 81.359 (1)°	T = 293 K
β = 80.165 (1)°	Block, colourless
γ = 64.920 (1)°	0.26 × 0.20 × 0.16 mm
V = 965.11 (18) Å³

Data collection top

CCD area-detector diffractometer	3415 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.014
Graphite monochromator	θ_max = 28.0°, θ_min = 1.9°
ω scans	h = −12→12
6035 measured reflections	k = −11→13
4223 independent reflections	l = −14→14

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.179	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.088P)² + 0.492P] where P = (F_o² + 2F_c²)/3
4223 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.97 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₃H₂₈N₂O₂	γ = 64.920 (1)°
M_r = 364.47	V = 965.11 (18) Å³
Triclinic, P1	Z = 2
a = 9.6452 (7) Å	Mo Kα radiation
b = 10.1247 (8) Å	µ = 0.08 mm⁻¹
c = 11.1168 (9) Å	T = 293 K
α = 81.359 (1)°	0.26 × 0.20 × 0.16 mm
β = 80.165 (1)°

Data collection top

CCD area-detector diffractometer	3415 reflections with I > 2σ(I)
6035 measured reflections	R_int = 0.014
4223 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.179	H-atom parameters constrained
S = 1.02	Δρ_max = 0.97 e Å⁻³
4223 reflections	Δρ_min = −0.35 e Å⁻³
244 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
O1	0.63667 (15)	0.25375 (14)	0.17134 (11)	0.0347 (3)
C2	0.7884 (2)	0.1737 (2)	0.20895 (16)	0.0308 (4)
C3	0.8958 (2)	0.1738 (2)	0.09030 (18)	0.0385 (5)
H3A	1.0016	0.1146	0.1057	0.046*
H3B	0.8726	0.1295	0.0291	0.046*
C4	0.8796 (3)	0.3276 (3)	0.0403 (2)	0.0505 (6)
H4A	0.9529	0.3224	−0.0324	0.061*
H4B	0.7767	0.3847	0.0173	0.061*
C5	0.9088 (3)	0.4018 (3)	0.1363 (2)	0.0556 (6)
H5A	0.8952	0.5006	0.1044	0.067*
H5B	1.0143	0.3485	0.1548	0.067*
C6	0.7984 (3)	0.4073 (2)	0.2534 (2)	0.0437 (5)
H6A	0.6937	0.4683	0.2360	0.052*
H6B	0.8218	0.4520	0.3141	0.052*
C7	0.8086 (2)	0.2550 (2)	0.30666 (17)	0.0333 (4)
H7	0.9114	0.1984	0.3326	0.040*
C8	0.6889 (2)	0.2674 (2)	0.41974 (17)	0.0374 (4)
H8	0.6817	0.3485	0.4624	0.045*
C9	0.5305 (2)	0.3101 (2)	0.38125 (17)	0.0330 (4)
C10	0.3968 (2)	0.3610 (2)	0.46364 (18)	0.0371 (4)
H10	0.4052	0.3641	0.5452	0.045*
C11	0.2532 (2)	0.4067 (2)	0.4277 (2)	0.0437 (5)
H11	0.1659	0.4380	0.4849	0.052*
C12	0.2387 (2)	0.4061 (2)	0.3068 (2)	0.0468 (5)
H12	0.1414	0.4411	0.2816	0.056*
C13	0.3687 (2)	0.3536 (2)	0.2228 (2)	0.0409 (5)
H13	0.3589	0.3519	0.1414	0.049*
C14	0.5143 (2)	0.30333 (19)	0.26049 (17)	0.0320 (4)
N15	0.79895 (17)	0.02740 (17)	0.26236 (14)	0.0315 (4)
C16	0.9542 (2)	−0.0761 (2)	0.2889 (2)	0.0413 (5)
H16A	0.9949	−0.0319	0.3376	0.050*
H16B	1.0223	−0.0999	0.2130	0.050*
C17	0.9471 (3)	−0.2134 (2)	0.3580 (2)	0.0487 (5)
H17A	1.0500	−0.2811	0.3756	0.058*
H17B	0.8828	−0.1892	0.4356	0.058*
O18	0.88758 (19)	−0.28253 (16)	0.29196 (16)	0.0530 (4)
C19	0.7387 (3)	−0.1820 (3)	0.2638 (2)	0.0519 (6)
H19A	0.6702	−0.1563	0.3394	0.062*
H19B	0.6983	−0.2286	0.2172	0.062*
C20	0.7407 (3)	−0.0447 (2)	0.1912 (2)	0.0421 (5)
H20A	0.8063	−0.0688	0.1141	0.050*
H20B	0.6373	0.0208	0.1732	0.050*
N21	0.7352 (2)	0.1391 (2)	0.50510 (16)	0.0445 (4)
H21	0.7949	0.0562	0.4772	0.053*
C22	0.6874 (2)	0.1424 (3)	0.63196 (18)	0.0419 (5)
C23	0.6910 (3)	0.0140 (3)	0.6964 (2)	0.0498 (5)
H23	0.7175	−0.0681	0.6548	0.060*
C24	0.6557 (3)	0.0060 (3)	0.8213 (2)	0.0578 (7)
H24	0.6600	−0.0822	0.8631	0.069*
C25	0.6145 (3)	0.1239 (3)	0.8861 (2)	0.0600 (7)
H25	0.5907	0.1168	0.9708	0.072*
C26	0.6090 (3)	0.2535 (3)	0.8234 (2)	0.0556 (6)
H26	0.5805	0.3353	0.8658	0.067*
C27	0.6459 (3)	0.2627 (3)	0.6965 (2)	0.0476 (5)
H27	0.6425	0.3506	0.6549	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0352 (7)	0.0364 (7)	0.0269 (6)	−0.0094 (6)	−0.0044 (5)	−0.0023 (5)
C2	0.0300 (9)	0.0298 (9)	0.0293 (9)	−0.0105 (7)	0.0004 (7)	−0.0023 (7)
C3	0.0438 (11)	0.0405 (11)	0.0313 (10)	−0.0199 (9)	0.0063 (8)	−0.0075 (8)
C4	0.0680 (16)	0.0482 (13)	0.0369 (11)	−0.0323 (12)	0.0127 (10)	−0.0044 (9)
C5	0.0713 (17)	0.0500 (13)	0.0543 (14)	−0.0389 (13)	0.0132 (12)	−0.0104 (11)
C6	0.0539 (13)	0.0390 (11)	0.0416 (11)	−0.0229 (10)	0.0022 (9)	−0.0105 (9)
C7	0.0318 (9)	0.0367 (10)	0.0305 (9)	−0.0137 (8)	−0.0012 (7)	−0.0039 (7)
C8	0.0359 (10)	0.0451 (11)	0.0275 (9)	−0.0139 (9)	−0.0018 (7)	−0.0030 (8)
C9	0.0325 (9)	0.0305 (9)	0.0314 (9)	−0.0100 (7)	−0.0017 (7)	−0.0004 (7)
C10	0.0386 (10)	0.0341 (10)	0.0340 (10)	−0.0132 (8)	0.0027 (8)	−0.0026 (8)
C11	0.0328 (10)	0.0356 (10)	0.0572 (13)	−0.0121 (8)	0.0056 (9)	−0.0060 (9)
C12	0.0301 (10)	0.0389 (11)	0.0687 (15)	−0.0091 (9)	−0.0111 (10)	−0.0066 (10)
C13	0.0412 (11)	0.0348 (10)	0.0457 (11)	−0.0111 (9)	−0.0138 (9)	−0.0045 (9)
C14	0.0328 (9)	0.0255 (8)	0.0337 (9)	−0.0091 (7)	−0.0032 (7)	−0.0005 (7)
N15	0.0281 (8)	0.0305 (8)	0.0335 (8)	−0.0110 (6)	−0.0029 (6)	−0.0002 (6)
C16	0.0317 (10)	0.0345 (10)	0.0532 (12)	−0.0102 (8)	−0.0047 (9)	−0.0010 (9)
C17	0.0445 (12)	0.0335 (10)	0.0595 (14)	−0.0079 (9)	−0.0111 (10)	0.0022 (10)
O18	0.0551 (10)	0.0327 (8)	0.0683 (11)	−0.0156 (7)	−0.0080 (8)	−0.0019 (7)
C19	0.0524 (13)	0.0433 (12)	0.0667 (15)	−0.0265 (11)	−0.0116 (11)	0.0023 (11)
C20	0.0451 (11)	0.0399 (11)	0.0449 (12)	−0.0207 (9)	−0.0092 (9)	0.0001 (9)
N21	0.0517 (11)	0.0376 (9)	0.0367 (9)	−0.0119 (8)	−0.0042 (8)	−0.0021 (7)
C22	0.0309 (10)	0.0601 (13)	0.0322 (10)	−0.0170 (9)	−0.0076 (8)	0.0028 (9)
C23	0.0455 (12)	0.0528 (13)	0.0524 (13)	−0.0200 (11)	−0.0090 (10)	−0.0049 (10)
C24	0.0557 (15)	0.0605 (15)	0.0574 (15)	−0.0298 (12)	−0.0132 (12)	0.0205 (12)
C25	0.0594 (15)	0.093 (2)	0.0260 (10)	−0.0330 (14)	−0.0065 (10)	0.0065 (12)
C26	0.0514 (14)	0.0619 (15)	0.0546 (14)	−0.0198 (12)	−0.0090 (11)	−0.0153 (12)
C27	0.0436 (12)	0.0476 (12)	0.0519 (13)	−0.0222 (10)	−0.0098 (10)	0.0104 (10)

Geometric parameters (Å, º) top

O1—C14	1.369 (2)	C13—C14	1.392 (3)
O1—C2	1.440 (2)	C13—H13	0.93
C2—N15	1.479 (2)	N15—C20	1.465 (3)
C2—C3	1.532 (2)	N15—C16	1.468 (2)
C2—C7	1.540 (3)	C16—C17	1.506 (3)
C3—C4	1.524 (3)	C16—H16A	0.97
C3—H3A	0.97	C16—H16B	0.97
C3—H3B	0.97	C17—O18	1.414 (3)
C4—C5	1.519 (3)	C17—H17A	0.97
C4—H4A	0.97	C17—H17B	0.97
C4—H4B	0.97	O18—C19	1.420 (3)
C5—C6	1.527 (3)	C19—C20	1.505 (3)
C5—H5A	0.97	C19—H19A	0.97
C5—H5B	0.97	C19—H19B	0.97
C6—C7	1.534 (3)	C20—H20A	0.97
C6—H6A	0.97	C20—H20B	0.97
C6—H6B	0.97	N21—C22	1.408 (3)
C7—C8	1.535 (3)	N21—H21	0.86
C7—H7	0.98	C22—C23	1.378 (3)
C8—N21	1.439 (3)	C22—C27	1.381 (3)
C8—C9	1.521 (3)	C23—C24	1.371 (4)
C8—H8	0.98	C23—H23	0.93
C9—C14	1.393 (3)	C24—C25	1.364 (4)
C9—C10	1.394 (3)	C24—H24	0.93
C10—C11	1.372 (3)	C25—C26	1.374 (4)
C10—H10	0.93	C25—H25	0.93
C11—C12	1.376 (3)	C26—C27	1.394 (3)
C11—H11	0.93	C26—H26	0.93
C12—C13	1.382 (3)	C27—H27	0.93
C12—H12	0.93

C14—O1—C2	118.1 (1)	C12—C13—C14	119.8 (2)
O1—C2—N15	107.33 (14)	C12—C13—H13	120.1
O1—C2—C3	103.46 (15)	C14—C13—H13	120.1
N15—C2—C3	114.86 (15)	O1—C14—C13	116.00 (17)
O1—C2—C7	108.99 (14)	O1—C14—C9	123.27 (17)
N15—C2—C7	109.78 (14)	C13—C14—C9	120.68 (18)
C3—C2—C7	112.01 (15)	C20—N15—C16	107.9 (2)
C4—C3—C2	112.25 (16)	C20—N15—C2	115.0 (2)
C4—C3—H3A	109.2	C16—N15—C2	114.3 (1)
C2—C3—H3A	109.2	N15—C16—C17	109.55 (17)
C4—C3—H3B	109.2	N15—C16—H16A	109.8
C2—C3—H3B	109.2	C17—C16—H16A	109.8
H3A—C3—H3B	107.9	N15—C16—H16B	109.8
C5—C4—C3	110.25 (19)	C17—C16—H16B	109.8
C5—C4—H4A	109.6	H16A—C16—H16B	108.2
C3—C4—H4A	109.6	O18—C17—C16	112.42 (19)
C5—C4—H4B	109.6	O18—C17—H17A	109.1
C3—C4—H4B	109.6	C16—C17—H17A	109.1
H4A—C4—H4B	108.1	O18—C17—H17B	109.1
C4—C5—C6	110.77 (19)	C16—C17—H17B	109.1
C4—C5—H5A	109.5	H17A—C17—H17B	107.9
C6—C5—H5A	109.5	C17—O18—C19	108.99 (17)
C4—C5—H5B	109.5	O18—C19—C20	112.28 (18)
C6—C5—H5B	109.5	O18—C19—H19A	109.1
H5A—C5—H5B	108.1	C20—C19—H19A	109.1
C5—C6—C7	112.50 (18)	O18—C19—H19B	109.1
C5—C6—H6A	109.1	C20—C19—H19B	109.1
C7—C6—H6A	109.1	H19A—C19—H19B	107.9
C5—C6—H6B	109.1	N15—C20—C19	109.22 (18)
C7—C6—H6B	109.1	N15—C20—H20A	109.8
H6A—C6—H6B	107.8	C19—C20—H20A	109.8
C6—C7—C8	110.36 (16)	N15—C20—H20B	109.8
C6—C7—C2	110.82 (15)	C19—C20—H20B	109.8
C8—C7—C2	111.22 (15)	H20A—C20—H20B	108.3
C6—C7—H7	108.1	C22—N21—C8	123.27 (18)
C8—C7—H7	108.1	C22—N21—H21	118.4
C2—C7—H7	108.1	C8—N21—H21	118.4
N21—C8—C9	113.15 (17)	C23—C22—C27	118.2 (2)
N21—C8—C7	112.77 (17)	C23—C22—N21	117.2 (2)
C9—C8—C7	110.48 (15)	C27—C22—N21	124.6 (2)
N21—C8—H8	106.7	C24—C23—C22	120.6 (2)
C9—C8—H8	106.7	C24—C23—H23	119.7
C7—C8—H8	106.7	C22—C23—H23	119.7
C14—C9—C10	117.68 (18)	C25—C24—C23	121.8 (2)
C14—C9—C8	120.62 (16)	C25—C24—H24	119.1
C10—C9—C8	121.67 (17)	C23—C24—H24	119.1
C11—C10—C9	121.80 (19)	C24—C25—C26	118.6 (2)
C11—C10—H10	119.1	C24—C25—H25	120.7
C9—C10—H10	119.1	C26—C25—H25	120.7
C10—C11—C12	119.79 (19)	C25—C26—C27	120.2 (2)
C10—C11—H11	120.1	C25—C26—H26	119.9
C12—C11—H11	120.1	C27—C26—H26	119.9
C11—C12—C13	120.1 (2)	C22—C27—C26	120.6 (2)
C11—C12—H12	119.9	C22—C27—H27	119.7
C13—C12—H12	119.9	C26—C27—H27	119.7

C14—O1—C2—N15	73.21 (18)	C12—C13—C14—O1	−179.76 (18)
C14—O1—C2—C3	−164.95 (15)	C12—C13—C14—C9	−2.3 (3)
C14—O1—C2—C7	−45.6 (2)	C10—C9—C14—O1	−179.21 (17)
O1—C2—C3—C4	63.5 (2)	C8—C9—C14—O1	2.6 (3)
N15—C2—C3—C4	−179.82 (17)	C10—C9—C14—C13	3.5 (3)
C7—C2—C3—C4	−53.7 (2)	C8—C9—C14—C13	−174.70 (18)
C2—C3—C4—C5	56.5 (3)	O1—C2—N15—C20	45.73 (19)
C3—C4—C5—C6	−57.4 (3)	C3—C2—N15—C20	−68.7 (2)
C4—C5—C6—C7	56.8 (3)	C7—C2—N15—C20	164.05 (16)
C5—C6—C7—C8	−176.72 (19)	O1—C2—N15—C16	171.42 (15)
C5—C6—C7—C2	−53.1 (2)	C3—C2—N15—C16	57.0 (2)
O1—C2—C7—C6	−62.82 (19)	C7—C2—N15—C16	−70.27 (19)
N15—C2—C7—C6	179.89 (15)	C20—N15—C16—C17	−58.2 (2)
C3—C2—C7—C6	51.0 (2)	C2—N15—C16—C17	172.44 (17)
O1—C2—C7—C8	60.34 (19)	N15—C16—C17—O18	59.0 (2)
N15—C2—C7—C8	−56.9 (2)	C16—C17—O18—C19	−57.4 (2)
C3—C2—C7—C8	174.20 (16)	C17—O18—C19—C20	57.9 (3)
C6—C7—C8—N21	−152.43 (18)	C16—N15—C20—C19	58.6 (2)
C2—C7—C8—N21	84.2 (2)	C2—N15—C20—C19	−172.46 (17)
C6—C7—C8—C9	79.8 (2)	O18—C19—C20—N15	−59.9 (3)
C2—C7—C8—C9	−43.6 (2)	C9—C8—N21—C22	−82.1 (2)
N21—C8—C9—C14	−114.40 (19)	C7—C8—N21—C22	151.6 (2)
C7—C8—C9—C14	13.1 (3)	C8—N21—C22—C23	157.2 (2)
N21—C8—C9—C10	67.5 (2)	C8—N21—C22—C27	−26.6 (3)
C7—C8—C9—C10	−165.00 (17)	C27—C22—C23—C24	−0.7 (3)
C14—C9—C10—C11	−1.6 (3)	N21—C22—C23—C24	175.8 (2)
C8—C9—C10—C11	176.58 (18)	C22—C23—C24—C25	0.7 (4)
C9—C10—C11—C12	−1.6 (3)	C23—C24—C25—C26	−0.2 (4)
C10—C11—C12—C13	2.8 (3)	C24—C25—C26—C27	−0.4 (4)
C11—C12—C13—C14	−0.9 (3)	C23—C22—C27—C26	0.1 (3)
C2—O1—C14—C13	−167.60 (16)	N21—C22—C27—C26	−176.1 (2)
C2—O1—C14—C9	15.0 (3)	C25—C26—C27—C22	0.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···N15	0.86	2.44	2.949 (3)	118
C20—H20B···O1	0.97	2.35	2.737 (2)	103
C11—H11···O18ⁱ	0.93	2.82	3.458 (3)	126
C12—H12···O18ⁱⁱ	0.93	2.83	3.524 (3)	132
C27—H27···CgCⁱⁱⁱ	0.93	2.87	3.704 (3)	150

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₈N₂O₂
M_r	364.47
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.6452 (7), 10.1247 (8), 11.1168 (9)
α, β, γ (°)	81.359 (1), 80.165 (1), 64.920 (1)
V (Å³)	965.11 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.26 × 0.20 × 0.16

Data collection
Diffractometer	CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6035, 4223, 3415
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.179, 1.02
No. of reflections	4223
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.97, −0.35

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1990)', SHELXL97 and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) top

O1—C14	1.369 (2)	C8—C9	1.521 (3)
O1—C2	1.440 (2)	C9—C14	1.393 (3)
C2—N15	1.479 (2)	N15—C20	1.465 (3)
C2—C7	1.540 (3)	N15—C16	1.468 (2)
C7—C8	1.535 (3)	C17—O18	1.414 (3)
C8—N21	1.439 (3)	O18—C19	1.420 (3)

C20—N15—C16	107.9 (2)	C16—N15—C2	114.3 (1)
C20—N15—C2	115.0 (2)

O1—C2—N15—C16	171.42 (15)	C7—C8—N21—C22	151.6 (2)
C3—C2—N15—C16	57.0 (2)	C8—N21—C22—C27	−26.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···N15	0.86	2.44	2.949 (3)	118
C20—H20B···O1	0.97	2.35	2.737 (2)	103
C11—H11···O18ⁱ	0.93	2.82	3.458 (3)	126
C12—H12···O18ⁱⁱ	0.93	2.83	3.524 (3)	132
C27—H27···CgCⁱⁱⁱ	0.93	2.87	3.704 (3)	150

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

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