4-Acetyl-2,N-di­benzoyl­aniline

Usman, A.; Razak, I.A.; Fun, H.-K.; Chantrapromma, S.; Tian, J.-Z.; Zhang, Y.; Xu, J.-H.

doi:10.1107/S1600536802005433

4-Acetyl-2,N-dibenzoylaniline

A. Usman, I. A. Razak, H.-K. Fun, S. Chantrapromma, J.-Z. Tian, Y. Zhang and J.-H. Xu

In the crystal structure of the title compound, C₂₂H₁₇NO₃, the N-benzoyl and 4-acetylaniline moieties are coplanar. The aromatic ring of the other benzoyl is twisted with respect to the attached 4-acetylaniline. The molecular structure is maintained by intramolecular C—H

O and N—H

O interactions, and the packing is stabilized by a weak C—H

O interaction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802005433/cv6101sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802005433/cv6101Isup2.hkl Contains datablock I

CCDC reference: 185772

checkCIF report

Key indicators

Single-crystal X-ray study
T = 213 K
Mean (C-C) = 0.003 Å
R factor = 0.067
wR factor = 0.172
Data-to-parameter ratio = 14.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

Comment top

Photoinduced electron transfer (PET) reactions of organic compounds have been extensively investigated in recent years (Scheinbaum, 1964; Kavarnos & Turro, 1986; D'Auria et al., 1996). Nitroaromatic compounds have been found to undergo PET reactions with 1,2-diphenylacetylene to give benzenamine derivatives among the other products (Tian & Xu, 2002). The crystal structures of the benzenamine derivatives have also been reported in our previous studies (Usman et al., 2002a,b). In our ongoing study on the PET reactions of nitroaromatic compounds, we have carried out a similar reaction for 4-nitroacetophenone and isolated the title compound, (I), which was structurally analyzed in order to elucidate its conformation.

The bond lengths and angles in (I) are within normal ranges (Allen et al., 1987), and are comparable with those in the related compound 4-acetyl-N,N-dibenzoylphenylamine (Usman et al., 2002b). The N-benzoyl and 4-acetylaniline moieties, corresponding to the two aromatic rings A (C1–C6) and B (C15–C20, and the O2/C14/C15/N1 plane, are nearly planar. The dihedral angles of between A and B, between A and O2/C14/C15/N1, and between B and O2/C14/C15/N1 are 8.6 (1), 3.8 (1), and 5.7 (1)°, respectively.

In the title compound, the acetyl group is twisted out about the C4—C21 bond from the attached phenyl by 4.3 (1)°, indicating that this group is coplanar with the attached aromatic ring A.

Aromatic ring C (C8–C13) of another benzoyl (C7–C13/O1) makes a dihedral angle of 59.2 (1)° with the attached aromatic ring A. The carbonyl group (atoms O1 and C7) of the benzoyl is extremely twisted from the aromatic ring C, with the O1 atom deviating by -0.875 (2) Å, and the O1/C6/C7/C8 plane being twisted by 48.9 (1)°.

There are two intramolecular interactions, N1—H1···O1 and C2—H2···O2 (Fig. 1), forming closed six-membered rings O1—C7—C6—C1—N1—H1 and O2—C14—N1—C1—C2—H2.

In the packing, the molecules are linked by weak C22—H22C···O2ⁱ [symmetry code: (i) 1 - x, 1 - y, -z] interactions into dimers which are stacked parallel to the b direction (Fig. 2). The packing is stabilized by this interaction, as -well as by dipole-dipole and van der Waals interactions

Experimental top

The title compound was isolated using silica-gel column chromatography from the photoinduced reaction mixtures of 4-nitroaceptophenone with 1,2-diphenylacetylene. Single crystals were obtained by slow evaporation of a chloroform–ethyl acetate (4:1) solution.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures top

	Fig. 1. A view of the title compound with displacement ellipsoids at the 50% probability level. The dashed lines denote the intramolecular interactions.
	Fig. 2. Packing diagram of the title compound viewed down the a axis, showing the formation of dimers, which are stacked parallel to the b direction.

4-acetyl-2,N-dibenzoylaniline top

Crystal data top

C₂₂H₁₇NO₃	D_x = 1.324 Mg m⁻³
M_r = 343.37	Melting point: 450(1)K K
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.6177 (6) Å	Cell parameters from 4602 reflections
b = 4.6546 (2) Å	θ = 2.6–28.3°
c = 31.9119 (16) Å	µ = 0.09 mm⁻¹
β = 93.047 (1)°	T = 213 K
V = 1723.22 (14) Å³	Needle, colorless
Z = 4	0.50 × 0.14 × 0.12 mm
F(000) = 720

Data collection top

Siemens SMART CCD area-detector diffractometer	2132 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.093
Graphite monochromator	θ_max = 28.4°, θ_min = 2.6°
Detector resolution: 8.33 pixels mm^-1	h = −12→15
ω scans	k = −6→6
9733 measured reflections	l = −42→37
4139 independent reflections

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)] = 0.067	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.172	w = 1/[σ²(F_o²) + (0.0586P)²] where P = (F_o² + 2F_c²)/3
S = 0.87	(Δ/σ)_max < 0.001
4139 reflections	Δρ_max = 0.34 e Å⁻³
293 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (2)

Crystal data top

C₂₂H₁₇NO₃	V = 1723.22 (14) Å³
M_r = 343.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.6177 (6) Å	µ = 0.09 mm⁻¹
b = 4.6546 (2) Å	T = 213 K
c = 31.9119 (16) Å	0.50 × 0.14 × 0.12 mm
β = 93.047 (1)°

Data collection top

Siemens SMART CCD area-detector diffractometer	2132 reflections with I > 2σ(I)
9733 measured reflections	R_int = 0.093
4139 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	Δρ_max = 0.34 e Å⁻³
4139 reflections	Δρ_min = −0.33 e Å⁻³
293 parameters

Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
N1	0.30666 (15)	0.4023 (4)	0.09561 (6)	0.0324 (5)
O1	0.29918 (15)	0.5481 (5)	0.17556 (5)	0.0634 (7)
O2	0.27950 (15)	0.2502 (4)	0.02778 (5)	0.0463 (5)
O3	0.71316 (14)	1.3093 (4)	0.12624 (5)	0.0465 (5)
C1	0.40055 (18)	0.5907 (5)	0.09366 (6)	0.0281 (5)
C2	0.45231 (19)	0.6522 (5)	0.05651 (7)	0.0326 (6)
C3	0.5433 (2)	0.8433 (5)	0.05622 (7)	0.0314 (6)
C4	0.58543 (17)	0.9789 (5)	0.09285 (7)	0.0270 (5)
C5	0.53508 (18)	0.9103 (5)	0.13019 (7)	0.0287 (5)
C6	0.44393 (17)	0.7167 (5)	0.13172 (6)	0.0272 (5)
C7	0.39519 (19)	0.6594 (6)	0.17299 (7)	0.0366 (6)
C8	0.46019 (19)	0.7417 (6)	0.21260 (7)	0.0326 (6)
C9	0.4014 (2)	0.8888 (7)	0.24303 (8)	0.0430 (7)
C10	0.4582 (2)	0.9653 (7)	0.28052 (8)	0.0512 (8)
C11	0.5721 (2)	0.8874 (7)	0.28854 (8)	0.0480 (8)
C12	0.6298 (2)	0.7332 (6)	0.25903 (8)	0.0434 (7)
C13	0.5748 (2)	0.6654 (6)	0.22089 (8)	0.0379 (6)
C14	0.25087 (19)	0.2495 (5)	0.06431 (7)	0.0314 (5)
C15	0.15023 (18)	0.0776 (5)	0.07751 (7)	0.0295 (5)
C16	0.0960 (2)	−0.0982 (6)	0.04795 (8)	0.0416 (7)
C17	0.0011 (2)	−0.2607 (7)	0.05771 (8)	0.0495 (8)
C18	−0.0412 (2)	−0.2448 (6)	0.09724 (8)	0.0410 (7)
C19	0.0119 (2)	−0.0700 (6)	0.12706 (8)	0.0419 (7)
C20	0.1077 (2)	0.0880 (6)	0.11737 (8)	0.0390 (6)
C21	0.68295 (19)	1.1879 (5)	0.09369 (7)	0.0315 (5)
C22	0.7426 (2)	1.2415 (6)	0.05396 (7)	0.0444 (7)
H22A	0.8197	1.3075	0.0607	0.067*
H22B	0.7012	1.3849	0.0376	0.067*
H22C	0.7453	1.0665	0.0381	0.067*
H5	0.5653 (17)	1.012 (5)	0.1555 (7)	0.028 (6)*
H11	0.613 (2)	0.938 (6)	0.3156 (8)	0.046 (7)*
H18	−0.110 (2)	−0.363 (6)	0.1054 (8)	0.055 (8)*
H1	0.277 (2)	0.399 (6)	0.1244 (8)	0.057 (8)*
H10	0.415 (2)	1.074 (6)	0.3001 (9)	0.062 (9)*
H13	0.611 (2)	0.574 (5)	0.2011 (7)	0.041 (7)*
H12	0.709 (3)	0.669 (6)	0.2648 (8)	0.066 (9)*
H2	0.4239 (18)	0.562 (5)	0.0302 (7)	0.032 (6)*
H20	0.141 (2)	0.208 (6)	0.1385 (8)	0.057 (8)*
H16	0.124 (2)	−0.111 (7)	0.0189 (9)	0.071 (9)*
H19	−0.021 (2)	−0.053 (6)	0.1544 (8)	0.054 (8)*
H3	0.5771 (19)	0.886 (5)	0.0306 (7)	0.036 (6)*
H17	−0.036 (2)	−0.369 (6)	0.0362 (8)	0.054 (8)*
H9	0.316 (3)	0.941 (7)	0.2367 (9)	0.083 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0297 (10)	0.0429 (14)	0.0248 (10)	−0.0098 (9)	0.0026 (8)	−0.0005 (9)
O1	0.0419 (10)	0.116 (2)	0.0339 (10)	−0.0385 (11)	0.0114 (8)	−0.0101 (11)
O2	0.0544 (11)	0.0523 (13)	0.0333 (9)	−0.0222 (9)	0.0126 (8)	−0.0100 (8)
O3	0.0496 (11)	0.0555 (13)	0.0347 (9)	−0.0206 (9)	0.0050 (8)	−0.0098 (9)
C1	0.0279 (11)	0.0298 (14)	0.0265 (11)	−0.0023 (9)	0.0019 (9)	0.0020 (10)
C2	0.0362 (13)	0.0364 (16)	0.0252 (11)	−0.0074 (11)	0.0018 (10)	0.0001 (11)
C3	0.0365 (12)	0.0332 (15)	0.0248 (11)	−0.0052 (10)	0.0044 (10)	0.0024 (10)
C4	0.0272 (11)	0.0270 (13)	0.0269 (11)	−0.0018 (9)	0.0024 (9)	0.0006 (9)
C5	0.0288 (11)	0.0323 (14)	0.0250 (11)	−0.0026 (10)	0.0016 (9)	−0.0020 (10)
C6	0.0258 (11)	0.0330 (14)	0.0234 (10)	−0.0013 (9)	0.0049 (9)	−0.0008 (10)
C7	0.0306 (12)	0.0502 (18)	0.0295 (12)	−0.0059 (11)	0.0073 (10)	0.0007 (11)
C8	0.0315 (12)	0.0424 (16)	0.0245 (11)	−0.0072 (10)	0.0065 (9)	0.0022 (11)
C9	0.0338 (13)	0.062 (2)	0.0335 (13)	−0.0025 (12)	0.0062 (11)	−0.0052 (13)
C10	0.0449 (16)	0.078 (2)	0.0316 (14)	−0.0044 (15)	0.0105 (12)	−0.0159 (14)
C11	0.0468 (16)	0.069 (2)	0.0279 (13)	−0.0115 (14)	−0.0009 (12)	−0.0015 (13)
C12	0.0375 (14)	0.0520 (19)	0.0402 (14)	−0.0039 (12)	−0.0018 (12)	0.0071 (13)
C13	0.0360 (13)	0.0446 (17)	0.0336 (13)	0.0000 (12)	0.0073 (11)	−0.0026 (12)
C14	0.0358 (12)	0.0292 (14)	0.0297 (12)	−0.0010 (10)	0.0046 (10)	−0.0012 (10)
C15	0.0318 (12)	0.0285 (14)	0.0285 (11)	−0.0022 (9)	0.0040 (9)	0.0020 (10)
C16	0.0427 (14)	0.0476 (18)	0.0354 (13)	−0.0156 (12)	0.0110 (11)	−0.0080 (13)
C17	0.0472 (16)	0.060 (2)	0.0416 (15)	−0.0256 (14)	0.0099 (13)	−0.0121 (15)
C18	0.0410 (14)	0.0427 (17)	0.0398 (14)	−0.0118 (12)	0.0077 (12)	0.0007 (13)
C19	0.0492 (15)	0.0432 (17)	0.0342 (13)	−0.0103 (12)	0.0122 (12)	0.0011 (12)
C20	0.0444 (14)	0.0408 (17)	0.0323 (13)	−0.0142 (12)	0.0059 (11)	−0.0030 (12)
C21	0.0326 (12)	0.0320 (15)	0.0302 (12)	−0.0038 (10)	0.0041 (10)	−0.0014 (10)
C22	0.0473 (15)	0.0488 (18)	0.0380 (14)	−0.0198 (13)	0.0114 (12)	−0.0032 (12)

Geometric parameters (Å, º) top

N1—C14	1.362 (3)	C10—H10	0.97 (3)
N1—C1	1.403 (3)	C11—C12	1.385 (4)
N1—H1	1.00 (3)	C11—H11	0.99 (2)
O1—C7	1.237 (3)	C12—C13	1.381 (3)
O2—C14	1.229 (3)	C12—H12	0.98 (3)
O3—C21	1.218 (3)	C13—H13	0.88 (2)
C1—C2	1.387 (3)	C14—C15	1.496 (3)
C1—C6	1.417 (3)	C15—C16	1.376 (3)
C2—C3	1.382 (3)	C15—C20	1.390 (3)
C2—H2	0.98 (2)	C16—C17	1.386 (3)
C3—C4	1.394 (3)	C16—H16	1.00 (3)
C3—H3	0.95 (2)	C17—C18	1.380 (3)
C4—C5	1.392 (3)	C17—H17	0.94 (3)
C4—C21	1.492 (3)	C18—C19	1.373 (3)
C5—C6	1.393 (3)	C18—H18	1.02 (3)
C5—H5	0.98 (2)	C19—C20	1.382 (3)
C6—C7	1.485 (3)	C19—H19	0.98 (2)
C7—C8	1.488 (3)	C20—H20	0.94 (3)
C8—C13	1.389 (3)	C21—C22	1.498 (3)
C8—C9	1.396 (3)	C22—H22A	0.9600
C9—C10	1.381 (3)	C22—H22B	0.9600
C9—H9	1.03 (3)	C22—H22C	0.9600
C10—C11	1.383 (4)

C14—N1—C1	129.38 (18)	C13—C12—C11	120.0 (3)
C14—N1—H1	119.7 (16)	C13—C12—H12	119.0 (17)
C1—N1—H1	110.8 (16)	C11—C12—H12	121.0 (16)
C2—C1—N1	122.7 (2)	C12—C13—C8	120.2 (2)
C2—C1—C6	119.8 (2)	C12—C13—H13	121.7 (15)
N1—C1—C6	117.54 (18)	C8—C13—H13	118.1 (15)
C3—C2—C1	120.4 (2)	O2—C14—N1	123.5 (2)
C3—C2—H2	119.5 (13)	O2—C14—C15	121.6 (2)
C1—C2—H2	120.1 (13)	N1—C14—C15	114.93 (19)
C2—C3—C4	121.3 (2)	C16—C15—C20	118.4 (2)
C2—C3—H3	119.5 (14)	C16—C15—C14	117.5 (2)
C4—C3—H3	119.1 (14)	C20—C15—C14	124.1 (2)
C5—C4—C3	118.0 (2)	C15—C16—C17	120.8 (2)
C5—C4—C21	119.17 (19)	C15—C16—H16	120.5 (17)
C3—C4—C21	122.83 (19)	C17—C16—H16	118.7 (17)
C4—C5—C6	122.2 (2)	C18—C17—C16	120.1 (3)
C4—C5—H5	116.3 (12)	C18—C17—H17	121.4 (16)
C6—C5—H5	121.4 (12)	C16—C17—H17	118.2 (16)
C5—C6—C1	118.30 (19)	C19—C18—C17	119.7 (2)
C5—C6—C7	118.3 (2)	C19—C18—H18	118.3 (14)
C1—C6—C7	123.4 (2)	C17—C18—H18	122.0 (15)
O1—C7—C6	121.4 (2)	C18—C19—C20	119.9 (2)
O1—C7—C8	118.07 (19)	C18—C19—H19	118.7 (15)
C6—C7—C8	120.47 (19)	C20—C19—H19	121.3 (15)
C13—C8—C9	119.5 (2)	C19—C20—C15	121.0 (2)
C13—C8—C7	122.3 (2)	C19—C20—H20	117.2 (16)
C9—C8—C7	118.2 (2)	C15—C20—H20	121.7 (16)
C10—C9—C8	120.0 (2)	O3—C21—C4	120.12 (19)
C10—C9—H9	121.2 (17)	O3—C21—C22	121.3 (2)
C8—C9—H9	118.8 (17)	C4—C21—C22	118.6 (2)
C9—C10—C11	120.0 (3)	C21—C22—H22A	109.5
C9—C10—H10	117.2 (16)	C21—C22—H22B	109.5
C11—C10—H10	122.8 (16)	H22A—C22—H22B	109.5
C10—C11—C12	120.2 (2)	C21—C22—H22C	109.5
C10—C11—H11	120.7 (14)	H22A—C22—H22C	109.5
C12—C11—H11	119.1 (14)	H22B—C22—H22C	109.5

C14—N1—C1—C2	0.5 (4)	C8—C9—C10—C11	−2.3 (5)
C14—N1—C1—C6	−178.4 (2)	C9—C10—C11—C12	0.2 (5)
N1—C1—C2—C3	178.9 (2)	C10—C11—C12—C13	2.2 (4)
C6—C1—C2—C3	−2.2 (4)	C11—C12—C13—C8	−2.5 (4)
C1—C2—C3—C4	−0.1 (4)	C9—C8—C13—C12	0.4 (4)
C2—C3—C4—C5	1.8 (4)	C7—C8—C13—C12	−176.5 (2)
C2—C3—C4—C21	−179.6 (2)	C1—N1—C14—O2	2.3 (4)
C3—C4—C5—C6	−1.2 (4)	C1—N1—C14—C15	−177.6 (2)
C21—C4—C5—C6	−179.9 (2)	O2—C14—C15—C16	5.0 (4)
C4—C5—C6—C1	−1.1 (3)	N1—C14—C15—C16	−175.1 (2)
C4—C5—C6—C7	−179.4 (2)	O2—C14—C15—C20	−174.1 (3)
C2—C1—C6—C5	2.8 (3)	N1—C14—C15—C20	5.8 (3)
N1—C1—C6—C5	−178.3 (2)	C20—C15—C16—C17	0.1 (4)
C2—C1—C6—C7	−179.0 (2)	C14—C15—C16—C17	−179.1 (2)
N1—C1—C6—C7	0.0 (3)	C15—C16—C17—C18	0.9 (5)
C5—C6—C7—O1	162.4 (3)	C16—C17—C18—C19	−0.9 (5)
C1—C6—C7—O1	−15.8 (4)	C17—C18—C19—C20	−0.2 (4)
C5—C6—C7—C8	−16.2 (3)	C18—C19—C20—C15	1.2 (4)
C1—C6—C7—C8	165.6 (2)	C16—C15—C20—C19	−1.2 (4)
O1—C7—C8—C13	130.8 (3)	C14—C15—C20—C19	177.9 (2)
C6—C7—C8—C13	−50.6 (4)	C5—C4—C21—O3	−4.4 (4)
O1—C7—C8—C9	−46.1 (4)	C3—C4—C21—O3	176.9 (2)
C6—C7—C8—C9	132.5 (3)	C5—C4—C21—C22	175.0 (2)
C13—C8—C9—C10	2.0 (4)	C3—C4—C21—C22	−3.6 (4)
C7—C8—C9—C10	179.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	1.00 (3)	1.78 (3)	2.646 (3)	143 (2)
C2—H2···O2	0.98 (2)	2.22 (2)	2.860 (3)	122 (2)
C22—H22C···O2ⁱ	0.96	2.57	3.469 (3)	156

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇NO₃
M_r	343.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	213
a, b, c (Å)	11.6177 (6), 4.6546 (2), 31.9119 (16)
β (°)	93.047 (1)
V (Å³)	1723.22 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.14 × 0.12

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9733, 4139, 2132
R_int	0.093
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.172, 0.87
No. of reflections	4139
No. of parameters	293
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.33

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT and SADABS (Sheldrick, 1996), SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Selected geometric parameters (Å, º) top

N1—C14	1.362 (3)	N1—C1	1.403 (3)

C14—N1—C1	129.38 (18)	C1—N1—H1	110.8 (16)
C14—N1—H1	119.7 (16)