Ethyl 2-amino-4-(4-methyl­phenyl)-4H-benzo­[f]­chromene-3-carboxyl­ate

Shi, D.; Wu, H.; Wang, X.; Zhuang, Q.; Hu, H.

doi:10.1107/S1600536803017033

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Ethyl 2-amino-4-(4-methylphenyl)-4H-benzo[f]chromene-3-carboxylate

D. Shi, H. Wu, X. Wang, Q. Zhuang and H. Hu

The pyran ring of the title molecule, C₂₃H₂₁NO₃, adopts a flattened boat conformation. In the crystal structure, the amino group is involved in both intra- and intermolecular N—H

O hydrogen bonds. The molecules form centrosymmetric dimers which are interlinked by weak C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803017033/ci6251sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803017033/ci6251Isup2.hkl Contains datablock I

CCDC reference: 222849

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.003 Å
R factor = 0.041
wR factor = 0.117
Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ..          C20

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

   0 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

Comment top

4H-Chromene is a structural unit of some natural products. 4H-Chromenes with amino and cyano groups are also the synthons of some special natural products (Hatokeyama et al., 1998; Ocallaghan & McMurry, 1995). We have previously reported the synthesis of some 4H-chromene derivatives (Shi et al., 2002; Zhuang et al., 2002). We report here the X-ray crystal structure of the title compound, (I).

The bond lengths and angles in (I) show normal values (Table 1). In the title molecule, the naphthalene ring system is planar within ±0.014 (3) Å. The pyran ring adopts a flattened boat conformation, with atoms O1 and C3 deviating from the C1/C2/C4/C5 plane by 0.143 (1) and 0.299 (2) Å, respectively. The naphthalene and phenyl ring planes form dihedral angles of 7.60 (5) and 89.16 (6)°, respectively, with the C1/C2/C4/C5 plane. The sum of the bond angles [353.0 (2)°] around N indiactes a planar geometry. An intramolecular N—H1A···O3 hydrogen bond is formed between the amino N atom and O atom of the carbonyl group (Table 2). The other H atom of the amino group is involved in weak N—H1B···O3(-x, −y, 1 − z) interactions to form centrosymmetric dimers (Fig. 2). The dimers are interlinked by weak C—H···π interactions involving the symmetry-related phenyl rings.

Experimental top

The title compound was prepared by the reaction of 2-naphthol with 4-methylbenzaldehyde and ethyl cyanoactate in ethanol in the presence of piperidine as catalyst. Single crystals suitable for X-ray diffraction were obtained by slow evaporation from an N,N-dimethylformamide–water solution.

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The structure of the title compound, showing 50% probability of displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. A view of the molecular packing down the c axis.

Ethyl 2-amino-4-(4-methylphenyl)-4H-benzo[f]chromene-3-carboxylate top

Crystal data top

C₂₃H₂₁NO₃	Z = 2
M_r = 359.41	F(000) = 380
Triclinic, P1	D_x = 1.284 Mg m⁻³
Hall symbol: -P 1	Melting point: 474-475 K K
a = 9.394 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.396 (1) Å	Cell parameters from 31 reflections
c = 11.005 (2) Å	θ = 3.7–14.3°
α = 94.98 (1)°	µ = 0.09 mm⁻¹
β = 98.30 (1)°	T = 292 K
γ = 102.95 (1)°	Block, colorless
V = 929.6 (3) Å³	0.56 × 0.50 × 0.36 mm

Data collection top

Siemens P4 diffractometer	R_int = 0.012
Radiation source: normal-focus sealed tube	θ_max = 25.0°, θ_min = 1.9°
Graphite monochromator	h = 0→11
ω scans	k = −11→10
3602 measured reflections	l = −13→12
3264 independent reflections	3 standard reflections every 97 reflections
2205 reflections with I > 2σ(I)	intensity decay: 3.0%

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.064P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3264 reflections	Δρ_max = 0.16 e Å⁻³
255 parameters	Δρ_min = −0.15 e Å⁻³
2 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (4)

Crystal data top

C₂₃H₂₁NO₃	γ = 102.95 (1)°
M_r = 359.41	V = 929.6 (3) Å³
Triclinic, P1	Z = 2
a = 9.394 (2) Å	Mo Kα radiation
b = 9.396 (1) Å	µ = 0.09 mm⁻¹
c = 11.005 (2) Å	T = 292 K
α = 94.98 (1)°	0.56 × 0.50 × 0.36 mm
β = 98.30 (1)°

Data collection top

Siemens P4 diffractometer	R_int = 0.012
3602 measured reflections	3 standard reflections every 97 reflections
3264 independent reflections	intensity decay: 3.0%
2205 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.041	2 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.16 e Å⁻³
3264 reflections	Δρ_min = −0.15 e Å⁻³
255 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	0.13586 (14)	0.41521 (13)	0.47413 (11)	0.0584 (4)
O2	0.30717 (14)	0.20685 (12)	0.82157 (12)	0.0581 (4)
O3	0.10953 (15)	0.06869 (13)	0.69058 (13)	0.0686 (4)
N	0.00388 (19)	0.1946 (2)	0.4971 (2)	0.0658 (5)
C1	0.12097 (18)	0.30647 (18)	0.54773 (17)	0.0476 (4)
C2	0.21166 (18)	0.31503 (17)	0.65719 (15)	0.0432 (4)
C3	0.31937 (17)	0.45914 (16)	0.71206 (14)	0.0402 (4)
H3	0.4106	0.4373	0.7526	0.048*
C4	0.35729 (18)	0.55277 (17)	0.61128 (15)	0.0420 (4)
C5	0.26502 (19)	0.52851 (18)	0.50094 (16)	0.0488 (4)
C6	0.2873 (2)	0.6147 (2)	0.40432 (18)	0.0651 (5)
H6	0.2212	0.5930	0.3300	0.078*
C7	0.4071 (3)	0.7300 (2)	0.42154 (19)	0.0693 (6)
H7	0.4221	0.7887	0.3585	0.083*
C8	0.5094 (2)	0.76279 (19)	0.53287 (18)	0.0566 (5)
C9	0.6352 (3)	0.8834 (2)	0.5525 (2)	0.0743 (6)
H9	0.6513	0.9430	0.4903	0.089*
C10	0.7318 (3)	0.9131 (2)	0.6598 (3)	0.0810 (7)
H10	0.8128	0.9936	0.6714	0.097*
C11	0.7109 (2)	0.8234 (2)	0.7538 (2)	0.0698 (6)
H11	0.7794	0.8436	0.8268	0.084*
C12	0.59049 (19)	0.70610 (19)	0.73956 (18)	0.0563 (5)
H12	0.5775	0.6480	0.8033	0.068*
C13	0.48582 (18)	0.67258 (17)	0.62886 (16)	0.0462 (4)
C14	0.2013 (2)	0.18703 (18)	0.72085 (17)	0.0491 (4)
C15	0.3120 (2)	0.0805 (2)	0.88819 (19)	0.0688 (6)
H15A	0.2117	0.0241	0.8875	0.083*
H15B	0.3578	0.1143	0.9737	0.083*
C16	0.3969 (3)	−0.0152 (2)	0.8315 (2)	0.0857 (7)
H16A	0.3512	−0.0493	0.7471	0.103*
H16B	0.3976	−0.0980	0.8767	0.103*
H16C	0.4968	0.0399	0.8340	0.103*
C17	0.25595 (17)	0.54075 (16)	0.80972 (14)	0.0390 (4)
C18	0.3136 (2)	0.5597 (2)	0.93329 (17)	0.0649 (6)
H18	0.3965	0.5247	0.9595	0.078*
C19	0.2512 (3)	0.6299 (2)	1.02001 (18)	0.0753 (6)
H19	0.2933	0.6409	1.1031	0.090*
C20	0.1293 (2)	0.68350 (19)	0.98655 (18)	0.0602 (5)
C21	0.0721 (2)	0.6643 (2)	0.86325 (19)	0.0640 (5)
H21	−0.0109	0.6994	0.8373	0.077*
C22	0.1335 (2)	0.59448 (19)	0.77602 (16)	0.0546 (5)
H22	0.0912	0.5836	0.6929	0.065*
C23	0.0588 (3)	0.7582 (2)	1.0807 (2)	0.0945 (8)
H23A	0.0464	0.8508	1.0560	0.113*
H23B	0.1213	0.7746	1.1602	0.113*
H23C	−0.0362	0.6967	1.0857	0.113*
H1A	−0.003 (3)	0.119 (2)	0.540 (2)	0.126 (11)*
H1B	−0.021 (2)	0.193 (2)	0.4187 (10)	0.077 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0560 (8)	0.0594 (8)	0.0549 (8)	0.0123 (7)	−0.0018 (6)	0.0030 (6)
O2	0.0691 (9)	0.0427 (7)	0.0640 (8)	0.0158 (6)	0.0091 (7)	0.0118 (6)
O3	0.0687 (9)	0.0417 (7)	0.0898 (10)	0.0002 (7)	0.0187 (8)	0.0030 (7)
N	0.0537 (11)	0.0624 (12)	0.0700 (13)	0.0056 (9)	−0.0009 (9)	−0.0129 (11)
C1	0.0443 (10)	0.0424 (10)	0.0556 (11)	0.0130 (8)	0.0082 (9)	−0.0043 (8)
C2	0.0420 (9)	0.0380 (9)	0.0505 (10)	0.0122 (7)	0.0099 (8)	−0.0004 (7)
C3	0.0368 (9)	0.0390 (9)	0.0456 (9)	0.0121 (7)	0.0056 (7)	0.0041 (7)
C4	0.0436 (9)	0.0395 (9)	0.0473 (10)	0.0154 (8)	0.0143 (8)	0.0039 (7)
C5	0.0533 (11)	0.0462 (10)	0.0499 (10)	0.0174 (9)	0.0108 (9)	0.0043 (8)
C6	0.0845 (15)	0.0676 (13)	0.0503 (11)	0.0286 (12)	0.0144 (10)	0.0132 (10)
C7	0.0984 (17)	0.0594 (13)	0.0650 (14)	0.0288 (13)	0.0376 (13)	0.0223 (10)
C8	0.0683 (13)	0.0455 (10)	0.0660 (13)	0.0186 (9)	0.0360 (11)	0.0079 (9)
C9	0.0892 (17)	0.0521 (12)	0.0886 (16)	0.0083 (12)	0.0530 (14)	0.0065 (11)
C10	0.0686 (15)	0.0584 (13)	0.113 (2)	−0.0067 (11)	0.0529 (15)	−0.0104 (14)
C11	0.0477 (12)	0.0664 (13)	0.0884 (15)	0.0033 (10)	0.0202 (11)	−0.0151 (12)
C12	0.0468 (11)	0.0510 (11)	0.0709 (13)	0.0096 (9)	0.0175 (10)	−0.0008 (9)
C13	0.0460 (10)	0.0395 (9)	0.0577 (11)	0.0152 (8)	0.0199 (9)	0.0006 (8)
C14	0.0504 (11)	0.0393 (10)	0.0604 (12)	0.0114 (9)	0.0212 (9)	−0.0001 (8)
C15	0.0886 (16)	0.0563 (12)	0.0720 (14)	0.0251 (11)	0.0255 (12)	0.0258 (10)
C16	0.1012 (18)	0.0667 (14)	0.1074 (19)	0.0416 (14)	0.0318 (15)	0.0299 (13)
C17	0.0393 (9)	0.0346 (8)	0.0414 (9)	0.0068 (7)	0.0052 (7)	0.0039 (7)
C18	0.0636 (12)	0.0867 (15)	0.0485 (11)	0.0329 (11)	0.0013 (9)	0.0047 (10)
C19	0.0888 (16)	0.0941 (16)	0.0400 (11)	0.0218 (14)	0.0081 (11)	−0.0033 (10)
C20	0.0733 (14)	0.0473 (11)	0.0595 (13)	0.0074 (10)	0.0261 (11)	−0.0026 (9)
C21	0.0649 (13)	0.0682 (13)	0.0689 (13)	0.0340 (11)	0.0176 (10)	0.0045 (10)
C22	0.0579 (11)	0.0622 (12)	0.0479 (11)	0.0271 (10)	0.0066 (9)	0.0007 (9)
C23	0.120 (2)	0.0806 (16)	0.0892 (17)	0.0223 (15)	0.0543 (15)	−0.0126 (13)

Geometric parameters (Å, º) top

O1—C1	1.353 (2)	C10—H10	0.93
O1—C5	1.399 (2)	C11—C12	1.371 (2)
O2—C14	1.347 (2)	C11—H11	0.93
O2—C15	1.454 (2)	C12—C13	1.414 (2)
O3—C14	1.2305 (19)	C12—H12	0.93
N—C1	1.352 (2)	C15—C16	1.484 (3)
N—H1A	0.88 (1)	C15—H15A	0.97
N—H1B	0.86 (1)	C15—H15B	0.97
C1—C2	1.356 (2)	C16—H16A	0.96
C2—C14	1.435 (2)	C16—H16B	0.96
C2—C3	1.513 (2)	C16—H16C	0.96
C3—C4	1.508 (2)	C17—C18	1.370 (2)
C3—C17	1.531 (2)	C17—C22	1.373 (2)
C3—H3	0.98	C18—C19	1.383 (3)
C4—C5	1.355 (2)	C18—H18	0.93
C4—C13	1.431 (2)	C19—C20	1.367 (3)
C5—C6	1.403 (3)	C19—H19	0.93
C6—C7	1.354 (3)	C20—C21	1.366 (3)
C6—H6	0.93	C20—C23	1.512 (2)
C7—C8	1.408 (3)	C21—C22	1.380 (2)
C7—H7	0.93	C21—H21	0.93
C8—C9	1.418 (3)	C22—H22	0.93
C8—C13	1.422 (2)	C23—H23A	0.96
C9—C10	1.348 (3)	C23—H23B	0.96
C9—H9	0.93	C23—H23C	0.96
C10—C11	1.398 (3)

C1—O1—C5	118.11 (13)	C11—C12—H12	119.7
C14—O2—C15	116.99 (14)	C13—C12—H12	119.7
C1—N—H1A	111.7 (19)	C12—C13—C8	118.33 (17)
C1—N—H1B	113.3 (15)	C12—C13—C4	122.26 (16)
H1A—N—H1B	128 (2)	C8—C13—C4	119.40 (17)
N—C1—O1	110.26 (17)	O3—C14—O2	120.93 (17)
N—C1—C2	126.81 (19)	O3—C14—C2	126.33 (18)
O1—C1—C2	122.93 (15)	O2—C14—C2	112.74 (15)
C1—C2—C14	119.12 (16)	O2—C15—C16	111.19 (16)
C1—C2—C3	119.98 (15)	O2—C15—H15A	109.4
C14—C2—C3	120.88 (15)	C16—C15—H15A	109.4
C4—C3—C2	110.25 (13)	O2—C15—H15B	109.4
C4—C3—C17	111.12 (12)	C16—C15—H15B	109.4
C2—C3—C17	110.72 (13)	H15A—C15—H15B	108.0
C4—C3—H3	108.2	C15—C16—H16A	109.5
C2—C3—H3	108.2	C15—C16—H16B	109.5
C17—C3—H3	108.2	C15—C16—H16C	109.5
C5—C4—C13	117.62 (16)	C18—C17—C22	116.92 (16)
C5—C4—C3	119.96 (15)	C18—C17—C3	122.67 (15)
C13—C4—C3	122.36 (15)	C22—C17—C3	120.37 (14)
C4—C5—O1	122.42 (16)	C17—C18—C19	121.47 (18)
C4—C5—C6	123.92 (18)	C17—C18—H18	119.3
O1—C5—C6	113.65 (16)	C19—C18—H18	119.3
C7—C6—C5	118.63 (19)	C20—C19—C18	121.67 (19)
C7—C6—H6	120.7	C20—C19—H19	119.2
C5—C6—H6	120.7	C18—C19—H19	119.2
C6—C7—C8	121.34 (19)	C21—C20—C19	116.70 (18)
C6—C7—H7	119.3	C21—C20—C23	121.2 (2)
C8—C7—H7	119.3	C19—C20—C23	122.1 (2)
C7—C8—C9	122.0 (2)	C20—C21—C22	122.09 (18)
C7—C8—C13	119.05 (17)	C20—C21—H21	119.0
C9—C8—C13	118.9 (2)	C22—C21—H21	119.0
C10—C9—C8	121.2 (2)	C17—C22—C21	121.17 (17)
C10—C9—H9	119.4	C17—C22—H22	119.4
C8—C9—H9	119.4	C21—C22—H22	119.4
C9—C10—C11	120.3 (2)	C20—C23—H23A	109.5
C9—C10—H10	119.8	C20—C23—H23B	109.5
C11—C10—H10	119.8	H23A—C23—H23B	109.5
C12—C11—C10	120.7 (2)	C20—C23—H23C	109.5
C12—C11—H11	119.6	H23A—C23—H23C	109.5
C10—C11—H11	119.6	H23B—C23—H23C	109.5
C11—C12—C13	120.6 (2)

C5—O1—C1—N	−169.46 (14)	C11—C12—C13—C4	−178.81 (15)
C5—O1—C1—C2	11.8 (2)	C7—C8—C13—C12	179.31 (16)
N—C1—C2—C14	10.1 (3)	C9—C8—C13—C12	−0.9 (2)
O1—C1—C2—C14	−171.32 (15)	C7—C8—C13—C4	−1.4 (2)
N—C1—C2—C3	−168.46 (16)	C9—C8—C13—C4	178.45 (15)
O1—C1—C2—C3	10.1 (2)	C5—C4—C13—C12	−178.98 (15)
C1—C2—C3—C4	−25.5 (2)	C3—C4—C13—C12	3.7 (2)
C14—C2—C3—C4	155.90 (14)	C5—C4—C13—C8	1.7 (2)
C1—C2—C3—C17	97.84 (17)	C3—C4—C13—C8	−175.62 (14)
C14—C2—C3—C17	−80.72 (18)	C15—O2—C14—O3	3.0 (2)
C2—C3—C4—C5	21.5 (2)	C15—O2—C14—C2	−176.27 (14)
C17—C3—C4—C5	−101.67 (17)	C1—C2—C14—O3	−5.4 (3)
C2—C3—C4—C13	−161.22 (13)	C3—C2—C14—O3	173.17 (15)
C17—C3—C4—C13	75.62 (18)	C1—C2—C14—O2	173.86 (14)
C13—C4—C5—O1	−179.57 (13)	C3—C2—C14—O2	−7.6 (2)
C3—C4—C5—O1	−2.1 (2)	C14—O2—C15—C16	84.2 (2)
C13—C4—C5—C6	−0.8 (2)	C4—C3—C17—C18	−125.74 (18)
C3—C4—C5—C6	176.62 (15)	C2—C3—C17—C18	111.38 (18)
C1—O1—C5—C4	−16.0 (2)	C4—C3—C17—C22	56.43 (19)
C1—O1—C5—C6	165.14 (15)	C2—C3—C17—C22	−66.45 (19)
C4—C5—C6—C7	−0.6 (3)	C22—C17—C18—C19	0.0 (3)
O1—C5—C6—C7	178.31 (16)	C3—C17—C18—C19	−177.93 (18)
C5—C6—C7—C8	1.0 (3)	C17—C18—C19—C20	0.0 (3)
C6—C7—C8—C9	−179.81 (17)	C18—C19—C20—C21	0.0 (3)
C6—C7—C8—C13	0.0 (3)	C18—C19—C20—C23	179.01 (19)
C7—C8—C9—C10	179.94 (19)	C19—C20—C21—C22	0.0 (3)
C13—C8—C9—C10	0.1 (3)	C23—C20—C21—C22	−179.03 (18)
C8—C9—C10—C11	1.0 (3)	C18—C17—C22—C21	0.0 (3)
C9—C10—C11—C12	−1.4 (3)	C3—C17—C22—C21	177.98 (16)
C10—C11—C12—C13	0.7 (3)	C20—C21—C22—C17	0.0 (3)
C11—C12—C13—C8	0.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H1A···O3	0.88 (1)	1.98 (2)	2.697 (3)	137 (2)
N—H1B···O3ⁱ	0.86 (1)	2.54 (2)	2.969 (2)	112 (1)
C16—H16B···CgPⁱⁱ	0.96	3.01	3.785 (2)	138
C23—H23C···CgPⁱⁱⁱ	0.96	2.98	3.789 (2)	143

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₁NO₃
M_r	359.41
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	9.394 (2), 9.396 (1), 11.005 (2)
α, β, γ (°)	94.98 (1), 98.30 (1), 102.95 (1)
V (Å³)	929.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.56 × 0.50 × 0.36

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3602, 3264, 2205
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.117, 1.01
No. of reflections	3264
No. of parameters	255
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15

Computer programs: XSCANS (Siemens, 1994), XSCANS, SHELXTL (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top

O1—C1	1.353 (2)	N—C1	1.352 (2)
O1—C5	1.399 (2)	C1—C2	1.356 (2)
O2—C14	1.347 (2)	C2—C3	1.513 (2)
O2—C15	1.454 (2)	C3—C4	1.508 (2)
O3—C14	1.2305 (19)

N—C1—O1	110.26 (17)	C4—C3—C17	111.12 (12)
N—C1—C2	126.81 (19)	C2—C3—C17	110.72 (13)
C4—C3—C2	110.25 (13)	O3—C14—C2	126.33 (18)

C14—C2—C3—C17	−80.72 (18)	C1—C2—C14—O3	−5.4 (3)
C17—C3—C4—C13	75.62 (18)	C3—C2—C14—O2	−7.6 (2)
C15—O2—C14—O3	3.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H1A···O3	0.88 (1)	1.98 (2)	2.697 (3)	137 (2)
N—H1B···O3ⁱ	0.86 (1)	2.54 (2)	2.969 (2)	112 (1)
C16—H16B···CgPⁱⁱ	0.96	3.01	3.785 (2)	138
C23—H23C···CgPⁱⁱⁱ	0.96	2.98	3.789 (2)	143

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

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