(3aS,9bR)-Methyl 1-methyl-3-phenyl-1,2,3,3a,4,9b-hexa­hydro­chromeno[4,3-b]pyrrole-3a-carboxyl­ate

Nirmala, S.; Kamala, E.T.S.; Sudha, L.; Ramesh, E.; Raghunathan, R.

doi:10.1107/S1600536808005199

(3aS,9bR)-Methyl 1-methyl-3-phenyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b]pyrrole-3a-carboxylate

S. Nirmala, E. T. S. Kamala, L. Sudha, E. Ramesh and R. Raghunathan

In the title compound, C₂₀H₂₁NO₃, the heterocyclic six-membered ring adopts a half-chair conformation and the pyrrolidine ring adopts an envelope conformation. The molecular conformation is stabilized by C—H

O and C—H

N interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808005199/bt2680sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808005199/bt2680Isup2.hkl Contains datablock I

CCDC reference: 684463

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.047
wR factor = 0.143
Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.61 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.27 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C20

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT793_ALERT_2_G Check the Absolute Configuration of C3     .....          S
PLAT793_ALERT_2_G Check the Absolute Configuration of C4     .....          S
PLAT793_ALERT_2_G Check the Absolute Configuration of C12    .....          S

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   0 ALERT type 5 Informative message, check

Comment top

Chromenopyrrole compounds are used in the treatment of impulsive disorders (Caine, 1993), aggressiveness (Tidey, 1992), parkinson's disease (Carlson, 1993), psychoses, memory disorders (Sokoloff et al., 1990), anxiety and depression (Wilner, 1985). Pyrroles are also very useful precursors in porphyrin synthesis (Sobral & Rocha Gonsalves, 2001a, Sobral & Rocha Gonsalves, 2001b), and as monomers for polymer chemistry (Brockmann & Tour, 1995), with applications ranging from non – linear optical materials (Suslick et al., 1992) to electronic noses (Di Natale et al., 1998).

The bond lengths, bond angles and torsion angles of the title compound are comparable with the similar structure solved earlier (Nirmala et al., 2008). The sum of bond angles around atom N1(331.7°) is in accordance with sp³ hybridization. The aromatic six-membered rings are oriented at an angle of 72.9 (5)° with respect to each other. The six-membered heterocyclic ring of the chromenopyrrole moiety adopts a half-chair conformation with puckering parameters of q₂ = 0.357 (1) Å, q₃= -0.314 (1) Å and ϕ= -157.9 (2)° (Cremer and Pople, 1975). Atom C4 deviates by 0.631 Å from the least – square plane through the remaining five atoms. The pyrrolidine ring adopts an envelope conformation with puckering parameters of q₂ = 0.438 (1) Å and ϕ = -39.8 (2)° (Cremer and Pople, 1975). Atom C12 deviates by 0.659 (4) Å from the least – square plane through the remaining four atoms.

No significant intermolecular π–π interactions are observed between two phenyl rings. Their centroids are separated by 3.9165 (1) Å. The molecular conformation is stabilized C— H···O and C— H···N interactions.

Related literature top

For related literature, see: Brockmann & Tour (1995); Caine (1993); Carlson (1993); Cremer & Pople (1975); Di Natale, Paolesse, Macagnano, Mantini, Goletti, Tarizzo & D'Amico (1998); Nirmala et al. (2008); Sobral & Rocha Gonsalves (2001a,b); Sokoloff et al. (1990); Suslick et al. (1992); Tidey (1992); Wilner (1985).

Experimental top

A solution of (Z)-methyl 2-((2 - formylphenoxy) methyl)-3- phenylacrylate (1 mmol), sarcosine (1 mmol), in anhydrous methanol (10 ml), was refluxed. Completion of the reaction was evidenced by TLC analysis. The solvent was removed in vacuum. The crude product was subjected to column chromatography on silica gel (100–200 mesh) using petroleum ether – ethyl acetate (7:3) as the eluent. Compound was recrystallized from methanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2/SAINT (Bruker, 2004); data reduction: SAINT/XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids
	Fig. 2. The packing of the molecules viewed down the a axis.

(3aS,9bR)-Methyl 1-methyl-3-phenyl-1,2,3,3a,4,9 b-hexahydrochromeno[4,3-b]pyrrole-3a-carboxylate top

Crystal data top

C₂₀H₂₁NO₃	Z = 2
M_r = 323.38	F(000) = 344
Triclinic, P1	D_x = 1.301 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9557 (4) Å	Cell parameters from 5117 reflections
b = 10.2575 (7) Å	θ = 2.6–28.1°
c = 10.2993 (8) Å	µ = 0.09 mm⁻¹
α = 79.626 (5)°	T = 293 K
β = 87.361 (5)°	Prism, colourless
γ = 88.744 (4)°	0.20 × 0.20 × 0.12 mm
V = 825.79 (9) Å³

Data collection top

Bruker KappaAPEX2 diffractometer	4126 independent reflections
Radiation source: fine-focus sealed tube	3051 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω and ϕ scans	θ_max = 28.4°, θ_min = 2.6°
Absorption correction: multi-scan (Blessing, 1995)	h = −10→10
T_min = 0.983, T_max = 0.990	k = −13→13
18704 measured reflections	l = −13→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.143	w = 1/[σ²(F_o²) + (0.0739P)² + 0.1492P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4126 reflections	Δρ_max = 0.23 e Å⁻³
218 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (5)

Crystal data top

C₂₀H₂₁NO₃	γ = 88.744 (4)°
M_r = 323.38	V = 825.79 (9) Å³
Triclinic, P1	Z = 2
a = 7.9557 (4) Å	Mo Kα radiation
b = 10.2575 (7) Å	µ = 0.09 mm⁻¹
c = 10.2993 (8) Å	T = 293 K
α = 79.626 (5)°	0.20 × 0.20 × 0.12 mm
β = 87.361 (5)°

Data collection top

Bruker KappaAPEX2 diffractometer	4126 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	3051 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.990	R_int = 0.030
18704 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.03	Δρ_max = 0.23 e Å⁻³
4126 reflections	Δρ_min = −0.21 e Å⁻³
218 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
C2	0.58609 (18)	0.33276 (15)	0.84198 (19)	0.0553 (4)
H2A	0.6321	0.3161	0.9291	0.066*
H2B	0.6651	0.2989	0.7811	0.066*
C3	0.41543 (16)	0.26557 (14)	0.84521 (15)	0.0396 (3)
H3	0.4205	0.2149	0.7730	0.047*
C4	0.29028 (15)	0.38426 (13)	0.80439 (13)	0.0347 (3)
C5	0.22346 (17)	0.44251 (15)	0.92274 (14)	0.0416 (3)
H5A	0.1512	0.3786	0.9785	0.050*
H5B	0.3170	0.4595	0.9742	0.050*
C6	0.19789 (18)	0.65300 (15)	0.78280 (15)	0.0437 (3)
C7	0.1233 (2)	0.77835 (17)	0.7635 (2)	0.0589 (5)
H7	0.0357	0.7975	0.8203	0.071*
C8	0.1789 (3)	0.87321 (18)	0.6611 (2)	0.0681 (5)
H8	0.1299	0.9574	0.6494	0.082*
C9	0.3069 (3)	0.84568 (17)	0.5748 (2)	0.0649 (5)
H9	0.3438	0.9106	0.5049	0.078*
C10	0.3803 (2)	0.72004 (15)	0.59337 (16)	0.0496 (4)
H10	0.4655	0.7010	0.5345	0.060*
C11	0.32870 (17)	0.62246 (13)	0.69811 (14)	0.0378 (3)
C12	0.40618 (15)	0.48584 (13)	0.71947 (13)	0.0342 (3)
H12	0.4335	0.4590	0.6342	0.041*
C13	0.36182 (15)	0.17036 (13)	0.96874 (14)	0.0366 (3)
C14	0.4024 (2)	0.18592 (16)	1.09382 (16)	0.0493 (4)
H14	0.4679	0.2571	1.1041	0.059*
C15	0.3472 (2)	0.09747 (18)	1.20362 (17)	0.0581 (4)
H15	0.3762	0.1092	1.2872	0.070*
C16	0.2497 (2)	−0.00770 (16)	1.19071 (18)	0.0549 (4)
H16	0.2121	−0.0669	1.2652	0.066*
C17	0.2083 (2)	−0.02486 (16)	1.06844 (19)	0.0545 (4)
H17	0.1417	−0.0957	1.0590	0.065*
C18	0.26509 (19)	0.06275 (14)	0.95821 (16)	0.0457 (4)
H18	0.2376	0.0491	0.8749	0.055*
C19	0.70301 (18)	0.53858 (16)	0.72905 (17)	0.0475 (4)
H19A	0.6792	0.6314	0.7017	0.071*
H19B	0.7314	0.4995	0.6528	0.071*
H19C	0.7958	0.5274	0.7866	0.071*
C20	0.14592 (16)	0.33900 (14)	0.73480 (15)	0.0402 (3)
C21	0.0540 (3)	0.2860 (3)	0.5379 (2)	0.0892 (8)
H21A	0.0932	0.2878	0.4480	0.134*
H21B	−0.0460	0.3399	0.5394	0.134*
H21C	0.0293	0.1965	0.5790	0.134*
N1	0.55638 (13)	0.47446 (11)	0.79846 (12)	0.0380 (3)
O1	0.13061 (13)	0.56333 (11)	0.88343 (11)	0.0525 (3)
O2	0.18247 (17)	0.33696 (15)	0.60870 (12)	0.0735 (4)
O3	0.01458 (14)	0.30253 (14)	0.78731 (13)	0.0663 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0314 (7)	0.0475 (9)	0.0774 (12)	0.0001 (6)	0.0029 (7)	0.0128 (8)
C3	0.0345 (6)	0.0368 (7)	0.0449 (8)	0.0008 (5)	0.0034 (5)	−0.0021 (6)
C4	0.0303 (6)	0.0362 (7)	0.0352 (7)	−0.0009 (5)	0.0013 (5)	−0.0008 (5)
C5	0.0375 (7)	0.0475 (8)	0.0367 (7)	0.0044 (6)	0.0044 (5)	−0.0014 (6)
C6	0.0445 (7)	0.0421 (8)	0.0459 (8)	0.0049 (6)	−0.0105 (6)	−0.0102 (6)
C7	0.0607 (10)	0.0490 (9)	0.0705 (12)	0.0145 (8)	−0.0175 (8)	−0.0182 (8)
C8	0.0816 (13)	0.0407 (9)	0.0842 (14)	0.0108 (8)	−0.0357 (11)	−0.0102 (9)
C9	0.0842 (13)	0.0419 (9)	0.0646 (11)	−0.0123 (8)	−0.0285 (10)	0.0087 (8)
C10	0.0588 (9)	0.0441 (8)	0.0440 (8)	−0.0119 (7)	−0.0114 (7)	0.0008 (6)
C11	0.0410 (7)	0.0357 (7)	0.0369 (7)	−0.0036 (5)	−0.0096 (5)	−0.0045 (5)
C12	0.0335 (6)	0.0364 (7)	0.0319 (7)	−0.0044 (5)	0.0026 (5)	−0.0044 (5)
C13	0.0317 (6)	0.0327 (6)	0.0436 (8)	0.0012 (5)	−0.0033 (5)	−0.0023 (5)
C14	0.0550 (9)	0.0426 (8)	0.0505 (9)	−0.0078 (6)	−0.0114 (7)	−0.0055 (7)
C15	0.0734 (11)	0.0560 (10)	0.0427 (9)	0.0043 (8)	−0.0094 (8)	−0.0016 (7)
C16	0.0571 (9)	0.0445 (9)	0.0544 (10)	0.0041 (7)	0.0048 (7)	0.0118 (7)
C17	0.0491 (8)	0.0374 (8)	0.0730 (12)	−0.0097 (6)	−0.0068 (8)	0.0034 (7)
C18	0.0488 (8)	0.0376 (7)	0.0502 (9)	−0.0050 (6)	−0.0110 (6)	−0.0039 (6)
C19	0.0357 (7)	0.0492 (8)	0.0560 (9)	−0.0088 (6)	0.0068 (6)	−0.0059 (7)
C20	0.0356 (6)	0.0371 (7)	0.0452 (8)	−0.0037 (5)	−0.0020 (6)	0.0007 (6)
C21	0.0921 (15)	0.122 (2)	0.0567 (12)	−0.0647 (15)	−0.0106 (11)	−0.0160 (12)
N1	0.0288 (5)	0.0415 (6)	0.0416 (6)	−0.0025 (4)	0.0015 (4)	−0.0022 (5)
O1	0.0496 (6)	0.0525 (6)	0.0521 (7)	0.0144 (5)	0.0101 (5)	−0.0058 (5)
O2	0.0680 (8)	0.1103 (11)	0.0448 (7)	−0.0518 (8)	0.0016 (6)	−0.0162 (7)
O3	0.0368 (6)	0.0932 (10)	0.0680 (8)	−0.0181 (6)	0.0043 (5)	−0.0116 (7)

Geometric parameters (Å, º) top

C2—N1	1.4593 (19)	C11—C12	1.5020 (18)
C2—C3	1.532 (2)	C12—N1	1.4672 (17)
C2—H2A	0.9700	C12—H12	0.9800
C2—H2B	0.9700	C13—C14	1.380 (2)
C3—C13	1.5083 (19)	C13—C18	1.382 (2)
C3—C4	1.5657 (17)	C14—C15	1.377 (2)
C3—H3	0.9800	C14—H14	0.9300
C4—C20	1.5058 (19)	C15—C16	1.371 (3)
C4—C5	1.5211 (19)	C15—H15	0.9300
C4—C12	1.5298 (17)	C16—C17	1.358 (3)
C5—O1	1.4326 (16)	C16—H16	0.9300
C5—H5A	0.9700	C17—C18	1.380 (2)
C5—H5B	0.9700	C17—H17	0.9300
C6—O1	1.3542 (19)	C18—H18	0.9300
C6—C7	1.389 (2)	C19—N1	1.4464 (17)
C6—C11	1.394 (2)	C19—H19A	0.9600
C7—C8	1.364 (3)	C19—H19B	0.9600
C7—H7	0.9300	C19—H19C	0.9600
C8—C9	1.379 (3)	C20—O3	1.1901 (17)
C8—H8	0.9300	C20—O2	1.3215 (19)
C9—C10	1.388 (2)	C21—O2	1.442 (2)
C9—H9	0.9300	C21—H21A	0.9600
C10—C11	1.386 (2)	C21—H21B	0.9600
C10—H10	0.9300	C21—H21C	0.9600

N1—C2—C3	106.72 (11)	N1—C12—C4	101.59 (10)
N1—C2—H2A	110.4	C11—C12—C4	111.76 (10)
C3—C2—H2A	110.4	N1—C12—H12	110.0
N1—C2—H2B	110.4	C11—C12—H12	110.0
C3—C2—H2B	110.4	C4—C12—H12	110.0
H2A—C2—H2B	108.6	C14—C13—C18	117.52 (13)
C13—C3—C2	118.02 (13)	C14—C13—C3	123.24 (13)
C13—C3—C4	114.69 (10)	C18—C13—C3	119.23 (13)
C2—C3—C4	103.54 (11)	C15—C14—C13	120.87 (15)
C13—C3—H3	106.6	C15—C14—H14	119.6
C2—C3—H3	106.6	C13—C14—H14	119.6
C4—C3—H3	106.6	C16—C15—C14	120.52 (16)
C20—C4—C5	109.80 (11)	C16—C15—H15	119.7
C20—C4—C12	115.64 (11)	C14—C15—H15	119.7
C5—C4—C12	108.18 (11)	C17—C16—C15	119.55 (15)
C20—C4—C3	109.63 (11)	C17—C16—H16	120.2
C5—C4—C3	112.03 (11)	C15—C16—H16	120.2
C12—C4—C3	101.36 (10)	C16—C17—C18	120.03 (15)
O1—C5—C4	111.89 (11)	C16—C17—H17	120.0
O1—C5—H5A	109.2	C18—C17—H17	120.0
C4—C5—H5A	109.2	C17—C18—C13	121.50 (15)
O1—C5—H5B	109.2	C17—C18—H18	119.3
C4—C5—H5B	109.2	C13—C18—H18	119.3
H5A—C5—H5B	107.9	N1—C19—H19A	109.5
O1—C6—C7	115.99 (14)	N1—C19—H19B	109.5
O1—C6—C11	123.19 (12)	H19A—C19—H19B	109.5
C7—C6—C11	120.76 (15)	N1—C19—H19C	109.5
C8—C7—C6	119.85 (17)	H19A—C19—H19C	109.5
C8—C7—H7	120.1	H19B—C19—H19C	109.5
C6—C7—H7	120.1	O3—C20—O2	122.50 (14)
C7—C8—C9	120.78 (16)	O3—C20—C4	124.50 (14)
C7—C8—H8	119.6	O2—C20—C4	112.91 (11)
C9—C8—H8	119.6	O2—C21—H21A	109.5
C8—C9—C10	119.33 (17)	O2—C21—H21B	109.5
C8—C9—H9	120.3	H21A—C21—H21B	109.5
C10—C9—H9	120.3	O2—C21—H21C	109.5
C11—C10—C9	121.17 (17)	H21A—C21—H21C	109.5
C11—C10—H10	119.4	H21B—C21—H21C	109.5
C9—C10—H10	119.4	C19—N1—C2	111.63 (11)
C10—C11—C6	118.09 (14)	C19—N1—C12	114.08 (11)
C10—C11—C12	121.91 (13)	C2—N1—C12	105.98 (11)
C6—C11—C12	119.97 (12)	C6—O1—C5	117.33 (11)
N1—C12—C11	113.14 (11)	C20—O2—C21	115.98 (14)

N1—C2—C3—C13	−129.88 (13)	C3—C4—C12—C11	−164.30 (11)
N1—C2—C3—C4	−1.93 (17)	C2—C3—C13—C14	33.72 (19)
C13—C3—C4—C20	−79.76 (15)	C4—C3—C13—C14	−88.74 (16)
C2—C3—C4—C20	150.25 (13)	C2—C3—C13—C18	−147.30 (14)
C13—C3—C4—C5	42.41 (16)	C4—C3—C13—C18	90.25 (16)
C2—C3—C4—C5	−87.58 (14)	C18—C13—C14—C15	−0.4 (2)
C13—C3—C4—C12	157.53 (12)	C3—C13—C14—C15	178.62 (14)
C2—C3—C4—C12	27.54 (14)	C13—C14—C15—C16	−0.4 (3)
C20—C4—C5—O1	−67.14 (15)	C14—C15—C16—C17	0.4 (3)
C12—C4—C5—O1	59.90 (14)	C15—C16—C17—C18	0.4 (3)
C3—C4—C5—O1	170.79 (11)	C16—C17—C18—C13	−1.1 (2)
O1—C6—C7—C8	−177.44 (15)	C14—C13—C18—C17	1.1 (2)
C11—C6—C7—C8	−0.4 (2)	C3—C13—C18—C17	−177.91 (13)
C6—C7—C8—C9	1.0 (3)	C5—C4—C20—O3	−28.52 (19)
C7—C8—C9—C10	−0.4 (3)	C12—C4—C20—O3	−151.25 (15)
C8—C9—C10—C11	−0.9 (3)	C3—C4—C20—O3	94.97 (17)
C9—C10—C11—C6	1.6 (2)	C5—C4—C20—O2	154.86 (13)
C9—C10—C11—C12	179.79 (14)	C12—C4—C20—O2	32.13 (17)
O1—C6—C11—C10	175.95 (13)	C3—C4—C20—O2	−81.65 (15)
C7—C6—C11—C10	−0.9 (2)	C3—C2—N1—C19	−150.89 (14)
O1—C6—C11—C12	−2.3 (2)	C3—C2—N1—C12	−26.14 (16)
C7—C6—C11—C12	−179.18 (13)	C11—C12—N1—C19	−72.87 (15)
C10—C11—C12—N1	87.51 (16)	C4—C12—N1—C19	167.17 (11)
C6—C11—C12—N1	−94.28 (15)	C11—C12—N1—C2	163.91 (12)
C10—C11—C12—C4	−158.54 (13)	C4—C12—N1—C2	43.96 (13)
C6—C11—C12—C4	19.67 (18)	C7—C6—O1—C5	−168.00 (14)
C20—C4—C12—N1	−161.84 (11)	C11—C6—O1—C5	15.0 (2)
C5—C4—C12—N1	74.57 (12)	C4—C5—O1—C6	−44.61 (17)
C3—C4—C12—N1	−43.38 (12)	O3—C20—O2—C21	−0.8 (3)
C20—C4—C12—C11	77.23 (14)	C4—C20—O2—C21	175.94 (17)
C5—C4—C12—C11	−46.35 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···N1	0.97	2.55	2.887 (2)	100
C12—H12···O2	0.98	2.43	2.781 (2)	101

Experimental details

Crystal data
Chemical formula	C₂₀H₂₁NO₃
M_r	323.38
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.9557 (4), 10.2575 (7), 10.2993 (8)
α, β, γ (°)	79.626 (5), 87.361 (5), 88.744 (4)
V (Å³)	825.79 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.12

Data collection
Diffractometer	Bruker KappaAPEX2 diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.983, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	18704, 4126, 3051
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.143, 1.03
No. of reflections	4126
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.21

Computer programs: APEX2 (Bruker, 2004), APEX2/SAINT (Bruker, 2004), SAINT/XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).