N-Benzoyl-r-2,c-6-di-2-furyl-t-3-methyl­piperidin-4-one

Thiruvalluvar, A.; Balamurugan, S.; Manimekalai, A.; Selvaraju, K.; Maruthavanan, T.

doi:10.1107/S1600536807022398

N-Benzoyl-r-2,c-6-di-2-furyl-t-3-methylpiperidin-4-one

A. Thiruvalluvar, S. Balamurugan, A. Manimekalai, K. Selvaraju and T. Maruthavanan

In the title molecule, C₂₁H₁₉NO₄, the piperidine ring adopts a chair conformation. The benzoyl group has a bisectional orientation. The planar furyl rings and the methyl group each have an axial orientation. The structure is stabilized by inter- and intramolecular C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022398/at2288sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022398/at2288Isup2.hkl Contains datablock I

CCDC reference: 651443

checkCIF report

Key indicators

Single-crystal X-ray study
T = 160 K
Mean (C-C) = 0.003 Å
R factor = 0.056
wR factor = 0.156
Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C2     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C3     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C6     = ...          S

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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

The title compound, (I), has been analysed as part of our crystallographic studies on substitued piperidines (Balamurugan et al., 2006; 2007). The present X-ray diffraction study was undertaken to determine how the conformation of the system is affected by the substitution of a benzoyl group at the first position (N), furyl rings at 2 and 6 and a methyl group at 3 of the piperidin-4-one.

In the title molecule, (I), the piperidine ring adopts a chair conformation. The furyl rings at positons 2,6, and the methyl group at position 3 have an axial orientation. The benzoyl group at N has a bisectional orientation. The dihedral angle between the two planar furyl rings is 25.6 (1)°. The phenyl ring makes dihedral angles of 55.2 (1)° and 63.6 (1)° between the furyl ring at 2 and 6 respectively. In the solid state, the molecules are linked by inter- and intramolecular C–H···O hydrogen bonds.

Related literature top

For related literature, see: Balamurugan et al. (2006, 2007); Kumar & Pillay (1993).

Experimental top

The title compound was prepared by following the general procedure reported by Kumar & Pillay (1993). A mixture of t(3)-methyl-r(2),c(6)-(2'-furyl)piperidin-4-one (2.45 g, 0.01 mol) benzoylchoride (1.16 ml, 0.01 mol) and triethylamine (3 ml, 0.03 mol) in benzene were refluxed for 8–10 h. The precipitated ammonium salt was filtered off and the solvent was washed with dilute HCl (2 N) followed by water and then removed at low pressure. The solid mass filtered off, dried and recrystallized from petroleum-ether (333–353 K). The yield of the isolated product was 2.44 g (70%).

Structure description top

For related literature, see: Balamurugan et al. (2006, 2007); Kumar & Pillay (1993).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

Fig. 1. View of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

N-Benzoyl-r-2,c-6-di-2-furyl-t-3-methylpiperidin-4-one top

Crystal data top

C₂₁H₁₉NO₄	F(000) = 1472
M_r = 349.37	D_x = 1.324 Mg m⁻³
Monoclinic, C2/c	Melting point: 427 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 20.5162 (5) Å	Cell parameters from 4257 reflections
b = 8.9727 (3) Å	θ = 2.0–27.5°
c = 19.0466 (6) Å	µ = 0.09 mm⁻¹
β = 91.395 (2)°	T = 160 K
V = 3505.17 (18) Å³	Tiny_blocks, colourless
Z = 8	0.30 × 0.20 × 0.15 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	2961 reflections with I > 2σ(I)
Radiation source: Nonius FR590 sealed tube generator	R_int = 0.076
Horizontally mounted graphite crystal monochromator	θ_max = 27.5°, θ_min = 2.1°
Detector resolution: 9 pixels mm^-1	h = −26→26
φ and ω scans with κ offsets	k = −11→11
37792 measured reflections	l = −24→24
4025 independent reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0737P)² + 3.1099P] where P = (F_o² + 2F_c²)/3
4025 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₁H₁₉NO₄	V = 3505.17 (18) Å³
M_r = 349.37	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.5162 (5) Å	µ = 0.09 mm⁻¹
b = 8.9727 (3) Å	T = 160 K
c = 19.0466 (6) Å	0.30 × 0.20 × 0.15 mm
β = 91.395 (2)°

Data collection top

Nonius KappaCCD area-detector diffractometer	2961 reflections with I > 2σ(I)
37792 measured reflections	R_int = 0.076
4025 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.06	Δρ_max = 0.25 e Å⁻³
4025 reflections	Δρ_min = −0.24 e Å⁻³
235 parameters

Special details top

Experimental. Solvent used: Mixture of Petroleum-ether Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.995 (2) Frames collected: 456 Seconds exposure per frame: 41 Degrees rotation per frame: 1.3 Crystal-Detector distance (mm): 30.0

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O4	0.44450 (7)	0.31744 (17)	0.09889 (9)	0.0463 (5)
O11	0.26740 (7)	−0.08170 (18)	0.25095 (7)	0.0433 (5)
O22	0.36694 (6)	−0.23026 (15)	0.10441 (7)	0.0319 (4)
O62	0.26918 (7)	−0.03856 (17)	0.00725 (7)	0.0408 (5)
N1	0.30183 (7)	0.03966 (16)	0.15425 (7)	0.0218 (4)
C2	0.37023 (8)	−0.0006 (2)	0.17102 (9)	0.0236 (5)
C3	0.41222 (9)	0.1392 (2)	0.18472 (10)	0.0307 (6)
C4	0.40042 (9)	0.2555 (2)	0.12821 (11)	0.0315 (6)
C5	0.32971 (9)	0.2907 (2)	0.11244 (11)	0.0321 (6)
C6	0.28968 (8)	0.1487 (2)	0.09787 (9)	0.0245 (5)
C11	0.25465 (8)	−0.0072 (2)	0.19834 (9)	0.0260 (5)
C21	0.39848 (8)	−0.09842 (19)	0.11577 (9)	0.0232 (5)
C23	0.40031 (10)	−0.3035 (2)	0.05332 (10)	0.0347 (6)
C24	0.45082 (10)	−0.2228 (2)	0.03307 (11)	0.0367 (6)
C25	0.44997 (10)	−0.0897 (2)	0.07390 (11)	0.0363 (6)
C31	0.39855 (11)	0.2062 (3)	0.25692 (12)	0.0440 (7)
C61	0.30274 (9)	0.0875 (2)	0.02632 (9)	0.0292 (6)
C63	0.28507 (13)	−0.0700 (3)	−0.06067 (11)	0.0532 (9)
C64	0.32643 (12)	0.0321 (3)	−0.08387 (11)	0.0551 (9)
C65	0.33858 (11)	0.1355 (3)	−0.02753 (11)	0.0422 (7)
C111	0.18492 (8)	0.0335 (2)	0.18188 (9)	0.0250 (5)
C112	0.15183 (9)	0.1149 (2)	0.23184 (10)	0.0315 (6)
C113	0.08644 (9)	0.1474 (3)	0.22100 (11)	0.0376 (7)
C114	0.05335 (9)	0.0957 (3)	0.16204 (11)	0.0391 (7)
C115	0.08574 (9)	0.0133 (3)	0.11304 (11)	0.0386 (7)
C116	0.15167 (9)	−0.0167 (2)	0.12244 (10)	0.0328 (6)
H2	0.37034	−0.05811	0.21475	0.0283*
H3	0.45821	0.10989	0.18408	0.0368*
H5A	0.32655	0.35584	0.07184	0.0385*
H5B	0.31167	0.34319	0.15204	0.0385*
H6	0.24347	0.17604	0.09874	0.0294*
H23	0.38914	−0.39661	0.03533	0.0416*
H24	0.48070	−0.24809	−0.00089	0.0440*
H25	0.47959	−0.01144	0.07188	0.0435*
H31A	0.40609	0.13207	0.29256	0.0660*
H31B	0.35402	0.23878	0.25798	0.0660*
H31C	0.42698	0.28954	0.26544	0.0660*
H63	0.26932	−0.15067	−0.08665	0.0639*
H64	0.34415	0.03583	−0.12831	0.0661*
H65	0.36565	0.21860	−0.02810	0.0506*
H112	0.17357	0.14731	0.27244	0.0377*
H113	0.06465	0.20459	0.25371	0.0450*
H114	0.00922	0.11643	0.15544	0.0469*
H115	0.06337	−0.02233	0.07345	0.0463*
H116	0.17359	−0.07083	0.08869	0.0394*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0396 (8)	0.0398 (9)	0.0606 (10)	−0.0118 (7)	0.0212 (7)	−0.0038 (7)
O11	0.0345 (8)	0.0630 (10)	0.0327 (8)	0.0069 (7)	0.0083 (6)	0.0233 (7)
O22	0.0355 (7)	0.0296 (7)	0.0311 (7)	−0.0072 (6)	0.0087 (6)	−0.0048 (5)
O62	0.0544 (9)	0.0388 (8)	0.0291 (8)	0.0037 (7)	−0.0012 (6)	−0.0043 (6)
N1	0.0218 (7)	0.0230 (8)	0.0206 (7)	0.0012 (6)	0.0033 (5)	0.0028 (6)
C2	0.0215 (8)	0.0275 (9)	0.0219 (9)	0.0002 (7)	0.0015 (7)	0.0004 (7)
C3	0.0248 (9)	0.0326 (11)	0.0347 (10)	−0.0013 (8)	0.0008 (8)	−0.0085 (8)
C4	0.0309 (10)	0.0242 (10)	0.0399 (11)	−0.0056 (8)	0.0120 (8)	−0.0107 (8)
C5	0.0363 (10)	0.0228 (10)	0.0376 (11)	0.0012 (8)	0.0115 (8)	0.0021 (8)
C6	0.0245 (8)	0.0260 (9)	0.0231 (9)	0.0028 (7)	0.0042 (7)	0.0054 (7)
C11	0.0271 (9)	0.0293 (10)	0.0219 (9)	−0.0009 (7)	0.0045 (7)	0.0023 (7)
C21	0.0233 (8)	0.0209 (9)	0.0255 (9)	0.0012 (7)	0.0002 (7)	0.0009 (7)
C23	0.0458 (12)	0.0277 (10)	0.0308 (10)	0.0018 (9)	0.0050 (9)	−0.0080 (8)
C24	0.0396 (11)	0.0325 (11)	0.0386 (11)	0.0072 (9)	0.0154 (9)	−0.0035 (9)
C25	0.0341 (10)	0.0264 (10)	0.0491 (12)	−0.0026 (8)	0.0173 (9)	−0.0025 (9)
C31	0.0426 (12)	0.0492 (13)	0.0402 (12)	−0.0045 (10)	−0.0004 (9)	−0.0159 (10)
C61	0.0313 (10)	0.0318 (10)	0.0245 (9)	0.0081 (8)	0.0040 (7)	0.0056 (7)
C63	0.0726 (17)	0.0608 (16)	0.0260 (11)	0.0274 (14)	−0.0054 (11)	−0.0113 (11)
C64	0.0580 (15)	0.086 (2)	0.0217 (11)	0.0368 (14)	0.0086 (10)	0.0035 (12)
C65	0.0410 (11)	0.0548 (14)	0.0312 (11)	0.0118 (10)	0.0122 (9)	0.0132 (10)
C111	0.0239 (9)	0.0273 (9)	0.0241 (9)	−0.0032 (7)	0.0050 (7)	0.0029 (7)
C112	0.0260 (9)	0.0361 (11)	0.0324 (10)	−0.0051 (8)	0.0040 (8)	−0.0076 (8)
C113	0.0273 (10)	0.0419 (12)	0.0438 (12)	−0.0024 (8)	0.0082 (8)	−0.0115 (10)
C114	0.0228 (9)	0.0523 (13)	0.0424 (12)	−0.0009 (9)	0.0032 (8)	−0.0035 (10)
C115	0.0309 (10)	0.0545 (14)	0.0303 (11)	−0.0062 (9)	−0.0022 (8)	−0.0063 (9)
C116	0.0315 (10)	0.0404 (11)	0.0268 (10)	−0.0010 (8)	0.0059 (8)	−0.0043 (8)

Geometric parameters (Å, º) top

O4—C4	1.210 (2)	C3—H3	0.9800
O11—C11	1.227 (2)	C5—H5A	0.9700
O22—C21	1.363 (2)	C5—H5B	0.9700
O22—C23	1.371 (2)	C6—H6	0.9800
O62—C61	1.369 (2)	C111—C112	1.390 (3)
O62—C63	1.371 (3)	C111—C116	1.383 (3)
N1—C2	1.477 (2)	C112—C113	1.384 (3)
N1—C6	1.470 (2)	C113—C114	1.378 (3)
N1—C11	1.363 (2)	C114—C115	1.375 (3)
C2—C3	1.540 (3)	C115—C116	1.387 (3)
C2—C21	1.498 (2)	C23—H23	0.9300
C3—C4	1.514 (3)	C24—H24	0.9300
C3—C31	1.533 (3)	C25—H25	0.9300
C4—C5	1.508 (3)	C31—H31A	0.9600
C5—C6	1.538 (3)	C31—H31B	0.9600
C6—C61	1.499 (2)	C31—H31C	0.9600
C11—C111	1.502 (2)	C63—H63	0.9300
C21—C25	1.341 (3)	C64—H64	0.9300
C23—C24	1.329 (3)	C65—H65	0.9300
C24—C25	1.426 (3)	C112—H112	0.9300
C61—C65	1.347 (3)	C113—H113	0.9300
C63—C64	1.332 (4)	C114—H114	0.9300
C64—C65	1.436 (3)	C115—H115	0.9300
C2—H2	0.9800	C116—H116	0.9300

O4···C115ⁱ	3.394 (3)	C65···H6^v	2.7200
O11···C112ⁱⁱ	3.200 (2)	C111···H31Bⁱⁱ	3.0000
O11···C64ⁱⁱⁱ	3.373 (3)	C111···H6	2.3800
O22···O62	3.1977 (19)	C113···H2^vii	3.0400
O22···N1	2.9348 (19)	C114···H31Cⁱⁱ	3.1000
O62···C116	3.305 (2)	C114···H113^xii	3.1000
O62···O22	3.1977 (19)	C115···H65^v	3.0800
O62···C21	3.366 (2)	C115···H23^xi	3.0700
O62···N1	2.9477 (19)	C115···H31Cⁱⁱ	3.0800
O4···H115ⁱ	2.8800	C116···H6	2.6000
O4···H24^iv	2.5200	H2···O11	2.2500
O11···H2	2.2500	H2···H31A	2.3700
O11···H5Bⁱⁱ	2.5800	H2···C113ⁱⁱ	3.0400
O11···H64ⁱⁱⁱ	2.7900	H2···H113ⁱⁱ	2.5800
O11···H112	2.8500	H3···C25	2.7600
O11···H112ⁱⁱ	2.7600	H3···H25	2.4500
O22···H112ⁱⁱ	2.7400	H5A···C65	2.7500
O62···H116	2.5500	H5A···H65	2.4200
N1···O22	2.9348 (19)	H5A···C63^v	2.9900
N1···O62	2.9477 (19)	H5B···C31	2.9200
N1···H31B	2.8500	H5B···H31B	2.3700
C4···C25	3.428 (3)	H5B···O11^vii	2.5800
C4···C65	3.374 (3)	H6···C111	2.3800
C5···C63^v	3.562 (3)	H6···C116	2.6000
C6···C116	3.241 (2)	H6···C64^v	3.0000
C6···C65^v	3.507 (3)	H6···C65^v	2.7200
C21···C61	3.063 (2)	H23···C115^xi	3.0700
C21···O62	3.366 (2)	H23···H115^xi	2.4200
C24···C114^vi	3.586 (3)	H24···O4^iv	2.5200
C25···C65	3.581 (3)	H25···C3	2.9200
C25···C4	3.428 (3)	H25···H3	2.4500
C25···C61	3.513 (3)	H31A···H2	2.3700
C31···C116^vii	3.555 (3)	H31A···H64ⁱⁱⁱ	2.5000
C61···C21	3.063 (2)	H31B···N1	2.8500
C61···C25	3.513 (3)	H31B···C5	2.8400
C63···C5^v	3.562 (3)	H31B···H5B	2.3700
C64···O11^viii	3.373 (3)	H31B···C111^vii	3.0000
C65···C4	3.374 (3)	H31C···C114^vii	3.1000
C65···C6^v	3.507 (3)	H31C···C115^vii	3.0800
C65···C25	3.581 (3)	H64···O11^viii	2.7900
C3···H25	2.9200	H64···H31A^viii	2.5000
C4···H65	3.0600	H65···C4	3.0600
C5···H31B	2.8400	H65···C5	2.8700
C5···H65	2.8700	H65···H5A	2.4200
C6···H116	3.0900	H65···C115^v	3.0800
C112···O11^vii	3.200 (2)	H112···O11	2.8500
C114···C24^ix	3.586 (3)	H112···O11^vii	2.7600
C115···O4^x	3.394 (3)	H112···O22^vii	2.7400
C116···O62	3.305 (2)	H113···C114^xii	3.1000
C116···C6	3.241 (2)	H113···H114^xii	2.4600
C116···C31ⁱⁱ	3.555 (3)	H113···H2^vii	2.5800
C23···H115^xi	2.9900	H114···H113^xii	2.4600
C23···H114^vi	3.0100	H114···C23^ix	3.0100
C24···H115^xi	3.0700	H114···C24^ix	2.9700
C24···H114^vi	2.9700	H115···O4^x	2.8800
C25···H3	2.7600	H115···C23^xi	2.9900
C31···H5B	2.9200	H115···C24^xi	3.0700
C63···H5A^v	2.9900	H115···H23^xi	2.4200
C64···H6^v	3.0000	H116···O62	2.5500
C65···H5A	2.7500	H116···C6	3.0900

C21—O22—C23	106.58 (14)	C6—C5—H5B	109.00
C61—O62—C63	106.91 (16)	H5A—C5—H5B	108.00
C2—N1—C6	117.67 (13)	N1—C6—H6	108.00
C2—N1—C11	118.47 (14)	C5—C6—H6	108.00
C6—N1—C11	123.03 (14)	C61—C6—H6	108.00
N1—C2—C3	111.23 (14)	C112—C111—C116	119.49 (16)
N1—C2—C21	111.92 (14)	C11—C111—C112	117.61 (15)
C3—C2—C21	111.83 (14)	C11—C111—C116	122.68 (16)
C2—C3—C4	111.20 (15)	C111—C112—C113	119.78 (18)
C2—C3—C31	110.95 (16)	C112—C113—C114	120.5 (2)
C4—C3—C31	109.74 (16)	C113—C114—C115	119.84 (18)
O4—C4—C3	122.44 (17)	C114—C115—C116	120.20 (19)
O4—C4—C5	122.57 (18)	C111—C116—C115	120.18 (18)
C3—C4—C5	114.98 (16)	O22—C23—H23	125.00
C4—C5—C6	111.69 (15)	C24—C23—H23	125.00
N1—C6—C5	109.85 (14)	C23—C24—H24	127.00
N1—C6—C61	112.92 (14)	C25—C24—H24	127.00
C5—C6—C61	111.17 (15)	C21—C25—H25	126.00
O11—C11—N1	122.04 (16)	C24—C25—H25	126.00
O11—C11—C111	119.06 (15)	C3—C31—H31A	109.00
N1—C11—C111	118.90 (15)	C3—C31—H31B	109.00
O22—C21—C2	115.45 (14)	C3—C31—H31C	109.00
O22—C21—C25	109.51 (15)	H31A—C31—H31B	109.00
C2—C21—C25	135.02 (16)	H31A—C31—H31C	109.00
O22—C23—C24	110.56 (16)	H31B—C31—H31C	110.00
C23—C24—C25	106.15 (18)	O62—C63—H63	125.00
C21—C25—C24	107.20 (17)	C64—C63—H63	125.00
O62—C61—C6	116.36 (15)	C63—C64—H64	126.00
O62—C61—C65	110.03 (17)	C65—C64—H64	126.00
C6—C61—C65	133.46 (18)	C61—C65—H65	127.00
O62—C63—C64	109.9 (2)	C64—C65—H65	127.00
C63—C64—C65	107.3 (2)	C111—C112—H112	120.00
C61—C65—C64	105.9 (2)	C113—C112—H112	120.00
C21—C2—H2	107.00	C112—C113—H113	120.00
N1—C2—H2	107.00	C114—C113—H113	120.00
C3—C2—H2	107.00	C113—C114—H114	120.00
C31—C3—H3	108.00	C115—C114—H114	120.00
C2—C3—H3	108.00	C114—C115—H115	120.00
C4—C3—H3	108.00	C116—C115—H115	120.00
C4—C5—H5B	109.00	C111—C116—H116	120.00
C4—C5—H5A	109.00	C115—C116—H116	120.00
C6—C5—H5A	109.00

C23—O22—C21—C2	−179.24 (15)	C3—C2—C21—C25	−3.2 (3)
C23—O22—C21—C25	−0.5 (2)	C2—C3—C4—O4	−131.7 (2)
C21—O22—C23—C24	0.2 (2)	C2—C3—C4—C5	49.6 (2)
C63—O62—C61—C6	176.40 (17)	C31—C3—C4—O4	105.2 (2)
C63—O62—C61—C65	0.3 (2)	C31—C3—C4—C5	−73.5 (2)
C61—O62—C63—C64	−0.5 (3)	O4—C4—C5—C6	129.7 (2)
C6—N1—C2—C3	52.52 (19)	C3—C4—C5—C6	−51.6 (2)
C6—N1—C2—C21	−73.38 (19)	C4—C5—C6—N1	50.5 (2)
C11—N1—C2—C3	−117.37 (17)	C4—C5—C6—C61	−75.2 (2)
C11—N1—C2—C21	116.73 (17)	N1—C6—C61—O62	56.6 (2)
C2—N1—C6—C5	−53.57 (19)	N1—C6—C61—C65	−128.4 (2)
C2—N1—C6—C61	71.13 (19)	C5—C6—C61—O62	−179.38 (15)
C11—N1—C6—C5	115.82 (17)	C5—C6—C61—C65	−4.4 (3)
C11—N1—C6—C61	−119.47 (17)	O11—C11—C111—C112	58.9 (2)
C2—N1—C11—O11	−0.3 (3)	O11—C11—C111—C116	−115.8 (2)
C2—N1—C11—C111	179.83 (15)	N1—C11—C111—C112	−121.19 (18)
C6—N1—C11—O11	−169.58 (17)	N1—C11—C111—C116	64.1 (2)
C6—N1—C11—C111	10.5 (2)	O22—C21—C25—C24	0.7 (2)
N1—C2—C3—C4	−47.42 (19)	C2—C21—C25—C24	179.02 (19)
N1—C2—C3—C31	75.02 (19)	O22—C23—C24—C25	0.2 (2)
C21—C2—C3—C4	78.53 (18)	C23—C24—C25—C21	−0.5 (2)
C21—C2—C3—C31	−159.03 (16)	O62—C61—C65—C64	0.0 (3)
N1—C2—C21—O22	−59.31 (19)	C6—C61—C65—C64	−175.2 (2)
N1—C2—C21—C25	122.4 (2)	O62—C63—C64—C65	0.5 (3)
C3—C2—C21—O22	175.12 (14)	C63—C64—C65—C61	−0.3 (3)

Symmetry codes: (i) x+1/2, y+1/2, z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x, −y, z+1/2; (iv) −x+1, −y, −z; (v) −x+1/2, −y+1/2, −z; (vi) x+1/2, y−1/2, z; (vii) −x+1/2, y+1/2, −z+1/2; (viii) x, −y, z−1/2; (ix) x−1/2, y+1/2, z; (x) x−1/2, y−1/2, z; (xi) −x+1/2, −y−1/2, −z; (xii) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O11	0.98	2.25	2.730 (2)	109
C5—H5B···O11^vii	0.97	2.58	3.508 (2)	161
C24—H24···O4^iv	0.93	2.52	3.452 (3)	176
C116—H116···O62	0.93	2.55	3.305 (2)	139

Symmetry codes: (iv) −x+1, −y, −z; (vii) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₉NO₄
M_r	349.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	160
a, b, c (Å)	20.5162 (5), 8.9727 (3), 19.0466 (6)
β (°)	91.395 (2)
V (Å³)	3505.17 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.15

Data collection
Diffractometer	Nonius KappaCCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	37792, 4025, 2961
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.156, 1.06
No. of reflections	4025
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.24

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).