2-(1H-1,2,3-Benzotriazol-1-yl)-1-benz­oyl­ethyl 4-methyl­benzoate

Zeng, W.-L.; Zhang, Y.-C.; Hong, Y.-M.

doi:10.1107/S1600536807036331

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2-(1H-1,2,3-Benzotriazol-1-yl)-1-benzoylethyl 4-methylbenzoate

W.-L. Zeng, Y.-C. Zhang and Y.-M. Hong

In the crystal structure of the title compound, C₂₃H₁₉N₃O₃, molecules are linked into chains parallel to the c axis by C—H

O hydrogen bonds. Adjacent chains are assembled into two-dimensional layers via C—H

N hydrogen bonds. The packing is further stabilized by π–π interactions between triazole and phenyl rings.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036331/rz2151sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036331/rz2151Isup2.hkl Contains datablock I

CCDC reference: 660215

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.004 Å
R factor = 0.049
wR factor = 0.140
Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C16    -   C17     ..       5.63 su

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C8     = ...          S

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

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

1H-Benzotriazole and its derivatives are an important class of compounds because they exhibit a broad spectrum of pharmacological activities such as antifungal, antitumor and antineoplastic activities (Chen & Wu, 2005). We report here the synthesis and crystal structure of the title compound as part of our ongoing studies on new benzotriazole compounds with higher bioactivity.

In the title compound (Fig. 1), all bond lengths and angles are within normal ranges (Allen et al., 1987). The benzotriazole ring system is essentially planar, with a dihedral angle of 2.67 (1)° between the triazole ring (atoms N1—N3/C1/C6) and the benzene ring (C1—C6). The dihedral angles between the mean planes of the benzotriazole system and the six-membered aromatic rings C10—C15 and C17—C22 are 6.85 (1) and 66.06 (1)°, respectively. The dihedral angle between these two latter rings is 61.7 (2)°. In the crystal structure, intermolecular C—H···O hydrogen bonds (Table1) link the molecules into chains running parallel to the c axis. Adjacent chains are assembled into two-dimensional layers via C—H···N hydrogen bonds (Fig. 2). The packing is further stabilized by π···π interactions occurring between symmetry-related triazole and phenyl rings [Cg1···Cg2ⁱ = 3.578 (3) Å; perpendicular interplanar distance = 3.568 (3) Å; Cg1 and Cg2 are the centroids of the N1—N3/C1/C6 triazole ring and C10—C15 phenyl ring, respectively; symmetry code: (i) 1/2 - x, 1/2 - y, 2 - z].

Related literature top

For a general background on the pharmacological activities of benzotriazoles, see: Chen & Wu (2005). For related literature, see: Allen et al. (1987).

Experimental top

Bromine (3.2 g, 0.02 mol) was added dropwise to a solution of 3-(1H-benzo[d][1,2,3]triazol-1-yl)-1-phenylpropan-1-one (5.0 g, 0.02 mol) and sodium acetate (1.6 g, 0.02 mol) in acetic acid (50 ml). The reaction proceeded for 7 h. Water (50 ml) and chloroform (20 ml) were then added. The organic layer was washed successively with a saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and the chloroform solution filtered. This fraction was cooled with ice-water, then a solution of 4-methylbenzoic acid (2.7 g, 0.02 mol) in acetone (10 ml) and triethylamine (2.8 ml) was added. The mixture was stirred with ice-water for about 6 h. The solution was then filtered and concentrated. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an acetone-ethylacetate (1:1 v/v) solution at room temperature over a period of one week.

Structure description top

For a general background on the pharmacological activities of benzotriazoles, see: Chen & Wu (2005). For related literature, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of title compound with 30% probability ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed along the c axis. Intermolecular hydrogen bonds are shown as dashed lines.

2-(1H-1,2,3-Benzotriazol-1-yl)-1-benzoylethyl 4-methylbenzoate top

Crystal data top

C₂₃H₁₉N₃O₃	F(000) = 1616
M_r = 385.41	D_x = 1.314 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1885 reflections
a = 20.376 (4) Å	θ = 2.3–22.6°
b = 19.648 (4) Å	µ = 0.09 mm⁻¹
c = 10.213 (2) Å	T = 294 K
β = 107.605 (4)°	Block, colourless
V = 3897.3 (13) Å³	0.22 × 0.18 × 0.12 mm
Z = 8

Data collection top

Siemens SMART CCD area-detector diffractometer	3994 independent reflections
Radiation source: fine-focus sealed tube	2014 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
φ and ω scans	θ_max = 26.4°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→25
T_min = 0.981, T_max = 0.989	k = −24→20
11106 measured reflections	l = −12→9

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.063P)² + 0.064P] where P = (F_o² + 2F_c²)/3
3994 reflections	(Δ/σ)_max = 0.004
263 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₃H₁₉N₃O₃	V = 3897.3 (13) Å³
M_r = 385.41	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.376 (4) Å	µ = 0.09 mm⁻¹
b = 19.648 (4) Å	T = 294 K
c = 10.213 (2) Å	0.22 × 0.18 × 0.12 mm
β = 107.605 (4)°

Data collection top

Siemens SMART CCD area-detector diffractometer	3994 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2014 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.989	R_int = 0.046
11106 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.00	Δρ_max = 0.26 e Å⁻³
3994 reflections	Δρ_min = −0.17 e Å⁻³
263 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	0.20658 (8)	0.12677 (8)	0.70219 (18)	0.0703 (5)
O2	0.14502 (7)	0.05617 (7)	0.86281 (16)	0.0550 (4)
O3	0.05904 (9)	0.06461 (9)	0.6674 (2)	0.0879 (6)
N1	0.36982 (10)	0.14012 (10)	1.0086 (2)	0.0598 (5)
N2	0.30975 (10)	0.16959 (9)	0.9822 (2)	0.0581 (5)
N3	0.26645 (9)	0.12819 (9)	1.02305 (18)	0.0471 (5)
C1	0.36587 (11)	0.07846 (11)	1.0694 (2)	0.0475 (6)
C2	0.41650 (11)	0.02937 (13)	1.1214 (3)	0.0624 (7)
H2	0.4608	0.0342	1.1146	0.075*
C3	0.39807 (13)	−0.02585 (13)	1.1825 (3)	0.0703 (8)
H3	0.4306	−0.0596	1.2180	0.084*
C4	0.33142 (12)	−0.03349 (12)	1.1938 (3)	0.0648 (7)
H4	0.3213	−0.0718	1.2377	0.078*
C5	0.28111 (11)	0.01386 (11)	1.1421 (2)	0.0538 (6)
H5	0.2368	0.0086	1.1482	0.065*
C6	0.30000 (10)	0.07063 (10)	1.0794 (2)	0.0431 (5)
C7	0.19630 (11)	0.14953 (11)	1.0045 (2)	0.0542 (6)
H7A	0.1953	0.1987	1.0130	0.065*
H7B	0.1808	0.1300	1.0773	0.065*
C8	0.14636 (11)	0.12887 (11)	0.8666 (2)	0.0519 (6)
H8	0.1003	0.1457	0.8609	0.062*
C9	0.16798 (11)	0.15841 (12)	0.7499 (2)	0.0524 (6)
C10	0.14402 (11)	0.22827 (11)	0.7005 (2)	0.0500 (6)
C11	0.18920 (13)	0.27258 (14)	0.6695 (3)	0.0662 (7)
H11	0.2345	0.2593	0.6824	0.079*
C12	0.16787 (18)	0.33635 (15)	0.6197 (3)	0.0817 (9)
H12	0.1990	0.3665	0.6008	0.098*
C13	0.1012 (2)	0.35565 (15)	0.5977 (3)	0.0873 (10)
H13	0.0868	0.3988	0.5632	0.105*
C14	0.05536 (15)	0.31160 (16)	0.6266 (3)	0.0809 (9)
H14	0.0097	0.3245	0.6106	0.097*
C15	0.07713 (12)	0.24794 (13)	0.6795 (3)	0.0642 (7)
H15	0.0463	0.2183	0.7009	0.077*
C16	0.09767 (11)	0.02871 (13)	0.7527 (3)	0.0605 (7)
C17	0.09855 (10)	−0.04588 (12)	0.7526 (2)	0.0522 (6)
C18	0.05402 (11)	−0.08051 (14)	0.6424 (2)	0.0627 (7)
H18	0.0250	−0.0563	0.5694	0.075*
C19	0.05285 (12)	−0.15056 (14)	0.6412 (3)	0.0636 (7)
H19	0.0227	−0.1730	0.5670	0.076*
C20	0.09510 (12)	−0.18837 (13)	0.7469 (3)	0.0597 (7)
C21	0.13932 (12)	−0.15321 (13)	0.8558 (3)	0.0611 (6)
H21	0.1684	−0.1776	0.9284	0.073*
C22	0.14135 (12)	−0.08347 (12)	0.8595 (2)	0.0597 (7)
H22	0.1716	−0.0613	0.9340	0.072*
C23	0.09377 (14)	−0.26485 (13)	0.7461 (3)	0.0859 (9)
H23A	0.1385	−0.2819	0.7507	0.129*
H23B	0.0607	−0.2806	0.6632	0.129*
H23C	0.0812	−0.2809	0.8241	0.129*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0719 (11)	0.0785 (12)	0.0655 (12)	0.0248 (9)	0.0282 (10)	0.0047 (9)
O2	0.0508 (9)	0.0517 (10)	0.0530 (11)	−0.0020 (7)	0.0011 (8)	0.0017 (8)
O3	0.0787 (13)	0.0800 (13)	0.0767 (14)	−0.0005 (10)	−0.0187 (10)	0.0139 (11)
N1	0.0540 (12)	0.0652 (14)	0.0566 (14)	−0.0139 (10)	0.0112 (10)	0.0065 (10)
N2	0.0613 (13)	0.0522 (12)	0.0573 (14)	−0.0143 (10)	0.0124 (10)	0.0042 (10)
N3	0.0496 (11)	0.0458 (11)	0.0425 (12)	−0.0046 (9)	0.0087 (9)	−0.0003 (9)
C1	0.0451 (13)	0.0523 (14)	0.0410 (14)	−0.0127 (11)	0.0065 (10)	−0.0011 (11)
C2	0.0433 (13)	0.0721 (18)	0.0647 (18)	−0.0037 (13)	0.0059 (12)	0.0003 (14)
C3	0.0598 (17)	0.0604 (17)	0.077 (2)	0.0031 (13)	0.0007 (14)	0.0091 (14)
C4	0.0644 (17)	0.0558 (16)	0.0639 (18)	−0.0124 (13)	0.0040 (13)	0.0122 (13)
C5	0.0488 (13)	0.0560 (15)	0.0517 (16)	−0.0076 (12)	0.0079 (11)	0.0042 (12)
C6	0.0437 (12)	0.0437 (13)	0.0363 (13)	−0.0070 (10)	0.0037 (10)	−0.0021 (10)
C7	0.0607 (15)	0.0494 (14)	0.0532 (16)	0.0033 (11)	0.0182 (12)	0.0002 (11)
C8	0.0467 (13)	0.0529 (15)	0.0520 (16)	0.0078 (11)	0.0087 (11)	0.0023 (12)
C9	0.0439 (13)	0.0620 (16)	0.0468 (15)	0.0083 (12)	0.0072 (11)	−0.0041 (12)
C10	0.0558 (14)	0.0502 (14)	0.0396 (14)	0.0047 (12)	0.0079 (11)	−0.0036 (11)
C11	0.0646 (16)	0.0695 (18)	0.0588 (17)	−0.0023 (14)	0.0101 (13)	−0.0005 (14)
C12	0.111 (3)	0.065 (2)	0.068 (2)	−0.0196 (18)	0.0262 (18)	−0.0009 (16)
C13	0.136 (3)	0.0563 (18)	0.062 (2)	0.024 (2)	0.019 (2)	0.0025 (15)
C14	0.084 (2)	0.084 (2)	0.070 (2)	0.0360 (18)	0.0181 (16)	0.0020 (17)
C15	0.0630 (16)	0.0662 (17)	0.0630 (18)	0.0133 (13)	0.0183 (13)	0.0049 (14)
C16	0.0463 (14)	0.0723 (19)	0.0525 (17)	−0.0045 (13)	−0.0007 (12)	0.0066 (14)
C17	0.0469 (13)	0.0599 (16)	0.0456 (15)	−0.0069 (11)	0.0074 (11)	0.0016 (12)
C18	0.0523 (15)	0.079 (2)	0.0481 (16)	−0.0104 (13)	0.0026 (12)	0.0011 (13)
C19	0.0606 (16)	0.079 (2)	0.0513 (17)	−0.0233 (14)	0.0168 (13)	−0.0140 (14)
C20	0.0667 (16)	0.0667 (17)	0.0547 (17)	−0.0143 (13)	0.0319 (14)	−0.0076 (14)
C21	0.0711 (17)	0.0628 (17)	0.0472 (16)	−0.0055 (13)	0.0145 (13)	−0.0017 (13)
C22	0.0612 (15)	0.0623 (17)	0.0468 (16)	−0.0076 (12)	0.0033 (12)	−0.0037 (13)
C23	0.106 (2)	0.071 (2)	0.090 (2)	−0.0212 (16)	0.0433 (18)	−0.0181 (16)

Geometric parameters (Å, º) top

O1—C9	1.214 (2)	C10—C11	1.372 (3)
O2—C16	1.353 (3)	C11—C12	1.373 (4)
O2—C8	1.429 (2)	C11—H11	0.9300
O3—C16	1.209 (3)	C12—C13	1.362 (4)
N1—N2	1.306 (2)	C12—H12	0.9300
N1—C1	1.375 (3)	C13—C14	1.369 (4)
N2—N3	1.356 (2)	C13—H13	0.9300
N3—C6	1.356 (3)	C14—C15	1.381 (4)
N3—C7	1.446 (3)	C14—H14	0.9300
C1—C6	1.385 (3)	C15—H15	0.9300
C1—C2	1.395 (3)	C16—C17	1.466 (3)
C2—C3	1.360 (3)	C17—C22	1.386 (3)
C2—H2	0.9300	C17—C18	1.391 (3)
C3—C4	1.405 (3)	C18—C19	1.377 (3)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.367 (3)	C19—C20	1.377 (3)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.397 (3)	C20—C21	1.386 (3)
C5—H5	0.9300	C20—C23	1.503 (3)
C7—C8	1.522 (3)	C21—C22	1.371 (3)
C7—H7A	0.9700	C21—H21	0.9300
C7—H7B	0.9700	C22—H22	0.9300
C8—C9	1.507 (3)	C23—H23A	0.9600
C8—H8	0.9800	C23—H23B	0.9600
C9—C10	1.493 (3)	C23—H23C	0.9600
C10—C15	1.370 (3)

C16—O2—C8	115.11 (18)	C10—C11—C12	120.4 (2)
N2—N1—C1	107.75 (18)	C10—C11—H11	119.8
N1—N2—N3	109.08 (18)	C12—C11—H11	119.8
N2—N3—C6	109.84 (17)	C13—C12—C11	120.2 (3)
N2—N3—C7	119.70 (18)	C13—C12—H12	119.9
C6—N3—C7	130.46 (18)	C11—C12—H12	119.9
N1—C1—C6	108.76 (19)	C12—C13—C14	120.0 (3)
N1—C1—C2	130.1 (2)	C12—C13—H13	120.0
C6—C1—C2	121.1 (2)	C14—C13—H13	120.0
C3—C2—C1	116.8 (2)	C13—C14—C15	119.8 (3)
C3—C2—H2	121.6	C13—C14—H14	120.1
C1—C2—H2	121.6	C15—C14—H14	120.1
C2—C3—C4	122.1 (2)	C10—C15—C14	120.2 (3)
C2—C3—H3	119.0	C10—C15—H15	119.9
C4—C3—H3	119.0	C14—C15—H15	119.9
C5—C4—C3	121.7 (2)	O3—C16—O2	120.8 (2)
C5—C4—H4	119.1	O3—C16—C17	126.0 (2)
C3—C4—H4	119.1	O2—C16—C17	113.2 (2)
C4—C5—C6	116.3 (2)	C22—C17—C18	118.5 (2)
C4—C5—H5	121.9	C22—C17—C16	122.5 (2)
C6—C5—H5	121.9	C18—C17—C16	119.0 (2)
N3—C6—C1	104.56 (18)	C19—C18—C17	120.1 (2)
N3—C6—C5	133.4 (2)	C19—C18—H18	120.0
C1—C6—C5	122.0 (2)	C17—C18—H18	120.0
N3—C7—C8	113.69 (18)	C18—C19—C20	121.8 (2)
N3—C7—H7A	108.8	C18—C19—H19	119.1
C8—C7—H7A	108.8	C20—C19—H19	119.1
N3—C7—H7B	108.8	C19—C20—C21	117.4 (2)
C8—C7—H7B	108.8	C19—C20—C23	122.0 (2)
H7A—C7—H7B	107.7	C21—C20—C23	120.6 (3)
O2—C8—C9	111.77 (18)	C22—C21—C20	121.8 (2)
O2—C8—C7	107.09 (18)	C22—C21—H21	119.1
C9—C8—C7	110.83 (19)	C20—C21—H21	119.1
O2—C8—H8	109.0	C21—C22—C17	120.3 (2)
C9—C8—H8	109.0	C21—C22—H22	119.8
C7—C8—H8	109.0	C17—C22—H22	119.8
O1—C9—C10	121.4 (2)	C20—C23—H23A	109.5
O1—C9—C8	120.0 (2)	C20—C23—H23B	109.5
C10—C9—C8	118.51 (19)	H23A—C23—H23B	109.5
C15—C10—C11	119.3 (2)	C20—C23—H23C	109.5
C15—C10—C9	121.4 (2)	H23A—C23—H23C	109.5
C11—C10—C9	119.2 (2)	H23B—C23—H23C	109.5

C1—N1—N2—N3	−0.6 (2)	C7—C8—C9—C10	−87.0 (2)
N1—N2—N3—C6	0.9 (2)	O1—C9—C10—C15	138.4 (2)
N1—N2—N3—C7	−179.93 (18)	C8—C9—C10—C15	−44.9 (3)
N2—N1—C1—C6	0.2 (2)	O1—C9—C10—C11	−38.5 (3)
N2—N1—C1—C2	−177.3 (2)	C8—C9—C10—C11	138.1 (2)
N1—C1—C2—C3	176.8 (2)	C15—C10—C11—C12	0.9 (4)
C6—C1—C2—C3	−0.4 (3)	C9—C10—C11—C12	177.9 (2)
C1—C2—C3—C4	−0.2 (4)	C10—C11—C12—C13	−1.4 (4)
C2—C3—C4—C5	0.9 (4)	C11—C12—C13—C14	0.6 (4)
C3—C4—C5—C6	−1.0 (3)	C12—C13—C14—C15	0.8 (4)
N2—N3—C6—C1	−0.7 (2)	C11—C10—C15—C14	0.5 (4)
C7—N3—C6—C1	−179.8 (2)	C9—C10—C15—C14	−176.4 (2)
N2—N3—C6—C5	176.6 (2)	C13—C14—C15—C10	−1.3 (4)
C7—N3—C6—C5	−2.4 (4)	C8—O2—C16—O3	−1.6 (3)
N1—C1—C6—N3	0.3 (2)	C8—O2—C16—C17	179.55 (18)
C2—C1—C6—N3	178.1 (2)	O3—C16—C17—C22	−175.4 (3)
N1—C1—C6—C5	−177.4 (2)	O2—C16—C17—C22	3.4 (3)
C2—C1—C6—C5	0.3 (3)	O3—C16—C17—C18	3.5 (4)
C4—C5—C6—N3	−176.6 (2)	O2—C16—C17—C18	−177.7 (2)
C4—C5—C6—C1	0.4 (3)	C22—C17—C18—C19	0.3 (3)
N2—N3—C7—C8	89.4 (2)	C16—C17—C18—C19	−178.6 (2)
C6—N3—C7—C8	−91.6 (3)	C17—C18—C19—C20	−0.2 (4)
C16—O2—C8—C9	−65.0 (2)	C18—C19—C20—C21	0.1 (3)
C16—O2—C8—C7	173.46 (19)	C18—C19—C20—C23	179.8 (2)
N3—C7—C8—O2	63.2 (2)	C19—C20—C21—C22	0.1 (4)
N3—C7—C8—C9	−58.9 (2)	C23—C20—C21—C22	−179.7 (2)
O2—C8—C9—O1	−29.6 (3)	C20—C21—C22—C17	0.0 (4)
C7—C8—C9—O1	89.8 (3)	C18—C17—C22—C21	−0.2 (4)
O2—C8—C9—C10	153.67 (18)	C16—C17—C22—C21	178.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	0.93	2.50	3.157 (3)	128
C7—H7A···N2ⁱⁱ	0.97	2.59	3.560 (3)	176
C18—H18···O3ⁱⁱⁱ	0.93	2.51	3.317 (3)	145

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

Experimental details

Crystal data
Chemical formula	C₂₃H₁₉N₃O₃
M_r	385.41
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	294
a, b, c (Å)	20.376 (4), 19.648 (4), 10.213 (2)
β (°)	107.605 (4)
V (Å³)	3897.3 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.22 × 0.18 × 0.12

Data collection
Diffractometer	Siemens SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	11106, 3994, 2014
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.140, 1.00
No. of reflections	3994
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.17

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	0.93	2.50	3.157 (3)	127.8
C7—H7A···N2ⁱⁱ	0.97	2.59	3.560 (3)	176.1
C18—H18···O3ⁱⁱⁱ	0.93	2.51	3.317 (3)	145.3

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

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