N-(3,4-Dimethoxy­benzyl­idene)-4-methyl­aniline

Li, Z.-J.; Gao, L.; Meng, A.; Huang, J.

doi:10.1107/S1600536807043784

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N-(3,4-Dimethoxybenzylidene)-4-methylaniline

Z.-J. Li, L. Gao, A. Meng and J. Huang

The title compound, C₁₆H₁₇NO₂, crystallizes with two independent molecules in the asymmetric unit. In these molecules, the two benzene rings form dihedral angles of 26.44 (15) and 35.97 (16)°. There are weak intermolecular C—H

O hydrogen-bonding interactions in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043784/at2373sup1.cif Contains datablocks 041001D, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043784/at2373Isup2.hkl Contains datablock I

CCDC reference: 663788

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.063
wR factor = 0.229
Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C32

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

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

   4 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Schiff base compounds and its derivatives have broad application in biological activity of antibacterial drugs, anti-virus, and anti-cancer (Tian, et al., 2006). Due to their important biological activities, these compounds have received a great deal of attention in connection with their syntheses and in the elucidation of their crystal structures. In search for new Schiff base compounds with higher biological activities, the title compound (I) was synthesized. We report herein its crystal structure.

The asymmetric unit of (I) contains two independent molecules (Fig. 1). In these molecules, the benzene rings A(C3—C8), B(C10—C15) and C(C19—C24), D(C26—C31) deviate only slightly from coplanarity with the dihedral angles of 26.44 (15) and 35.97 (16)°, respectively. The dihedral angles A/C and B/D are 11.42 (16) and 72.31 (15)°, respectively. In (I), all the bond lengths and angles are generally normal (Allen et al., 1987). In the title molecule, the average C═N, C—C and C—O bond distances [1.274 (4), 1.507 (4) and 1.374 (3) Å, respectively] are also in good agreement with an earlier report (Li et al., 2006). The torsion angles C10—N1═ C9—C6 and C26—N2═C25—C21 are -177.7 (2)° and 178.0 (2) °, respectively.

There are some weak intermolecular C—H···O hydrogen bonding interactions in the crystal structure, providing stabilization (Table 1, Fig. 2).

Related literature top

For related literature, see: Allen et al. (1987); Li et al. (2006); Tian et al. (2006).

Experimental top

The title compound (I) was prepared by reaction of [(3,4-dimethoxy-benzylidene)-amino]-ethanol and (right) toluidine in ethanol at room temperature. Single crystals of the title compound suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Structure description top

There are some weak intermolecular C—H···O hydrogen bonding interactions in the crystal structure, providing stabilization (Table 1, Fig. 2).

For related literature, see: Allen et al. (1987); Li et al. (2006); Tian et al. (2006).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL (Bruker, 1999).

Figures top

Fig. 1. View of the title compound (I), with displacement ellipsoids drawn at the 30% probability level.

N-(3,4-Dimethoxybenzylidene)-4-methylaniline top

Crystal data top

C₁₆H₁₇NO₂	Z = 4
M_r = 255.31	F(000) = 544
Triclinic, P1	D_x = 1.194 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.777 (2) Å	Cell parameters from 2566 reflections
b = 12.304 (3) Å	θ = 1.6–27.0°
c = 13.716 (3) Å	µ = 0.08 mm⁻¹
α = 67.84 (3)°	T = 293 K
β = 81.97 (3)°	Slice, colourless
γ = 68.41 (3)°	0.54 × 0.34 × 0.18 mm
V = 1420.9 (5) Å³

Data collection top

Bruker P4 diffractometer	R_int = 0.018
Radiation source: fine-focus sealed tube	θ_max = 27.0°, θ_min = 1.6°
Graphite monochromator	h = 0→11
ω scans	k = −14→14
6427 measured reflections	l = −16→16
6059 independent reflections	3 standard reflections every 200 reflections
2536 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.229	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.1145P)² + 0.0112P] where P = (F_o² + 2F_c²)/3
6059 reflections	(Δ/σ)_max < 0.001
343 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₆H₁₇NO₂	γ = 68.41 (3)°
M_r = 255.31	V = 1420.9 (5) Å³
Triclinic, P1	Z = 4
a = 9.777 (2) Å	Mo Kα radiation
b = 12.304 (3) Å	µ = 0.08 mm⁻¹
c = 13.716 (3) Å	T = 293 K
α = 67.84 (3)°	0.54 × 0.34 × 0.18 mm
β = 81.97 (3)°

Data collection top

Bruker P4 diffractometer	R_int = 0.018
6427 measured reflections	3 standard reflections every 200 reflections
6059 independent reflections	intensity decay: none
2536 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.229	H-atom parameters constrained
S = 1.01	Δρ_max = 0.21 e Å⁻³
6059 reflections	Δρ_min = −0.22 e Å⁻³
343 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	0.0106 (2)	0.25461 (19)	0.48495 (17)	0.0722 (6)
O2	0.1218 (2)	0.42907 (18)	0.42852 (17)	0.0717 (6)
N1	0.2567 (3)	−0.0024 (2)	0.24077 (19)	0.0627 (7)
C1	−0.0405 (4)	0.1520 (3)	0.5273 (3)	0.0725 (9)
H1B	−0.1079	0.1623	0.5838	0.109*
H1C	0.0414	0.0759	0.5534	0.109*
H1D	−0.0897	0.1484	0.4733	0.109*
C2	0.1898 (4)	0.5212 (3)	0.4088 (3)	0.0797 (10)
H2A	0.1461	0.5691	0.4536	0.120*
H2B	0.1753	0.5758	0.3365	0.120*
H2C	0.2932	0.4801	0.4233	0.120*
C3	0.1688 (3)	0.3528 (3)	0.3719 (2)	0.0593 (8)
C4	0.2673 (4)	0.3626 (3)	0.2896 (3)	0.0697 (9)
H4A	0.3061	0.4267	0.2682	0.084*
C5	0.3089 (4)	0.2773 (3)	0.2383 (2)	0.0706 (9)
H5A	0.3758	0.2848	0.1830	0.085*
C6	0.2528 (3)	0.1816 (3)	0.2678 (2)	0.0611 (8)
C7	0.1506 (3)	0.1716 (3)	0.3515 (2)	0.0584 (8)
H7A	0.1118	0.1077	0.3721	0.070*
C8	0.1082 (3)	0.2557 (3)	0.4025 (2)	0.0562 (7)
C9	0.3004 (3)	0.0904 (3)	0.2150 (2)	0.0650 (8)
H9A	0.3664	0.1007	0.1593	0.078*
C10	0.3127 (3)	−0.0892 (3)	0.1876 (2)	0.0555 (7)
C11	0.4502 (3)	−0.1165 (3)	0.1398 (2)	0.0644 (8)
H11A	0.5126	−0.0751	0.1405	0.077*
C12	0.4950 (3)	−0.2034 (3)	0.0918 (2)	0.0677 (9)
H12A	0.5875	−0.2200	0.0606	0.081*
C13	0.4047 (4)	−0.2682 (3)	0.0885 (2)	0.0650 (8)
C14	0.2682 (3)	−0.2403 (3)	0.1360 (2)	0.0670 (9)
H14A	0.2053	−0.2808	0.1344	0.080*
C15	0.2223 (3)	−0.1537 (3)	0.1862 (2)	0.0637 (8)
H15A	0.1309	−0.1386	0.2190	0.076*
C16	0.4536 (5)	−0.3650 (3)	0.0369 (3)	0.0969 (12)
H16A	0.3779	−0.3998	0.0442	0.145*
H16B	0.5420	−0.4302	0.0700	0.145*
H16C	0.4722	−0.3267	−0.0365	0.145*
O3	0.5841 (2)	0.44440 (17)	0.40783 (16)	0.0687 (6)
O4	0.5223 (2)	0.24385 (17)	0.49333 (16)	0.0646 (6)
N2	0.7675 (3)	−0.0204 (2)	0.25563 (19)	0.0574 (6)
C17	0.5994 (5)	0.5632 (3)	0.3599 (3)	0.0958 (13)
H17A	0.5550	0.6120	0.4039	0.144*
H17B	0.5516	0.6050	0.2926	0.144*
H17C	0.7019	0.5533	0.3508	0.144*
C18	0.4808 (4)	0.1364 (2)	0.5426 (2)	0.0670 (9)
H18A	0.4218	0.1435	0.6036	0.100*
H18B	0.5673	0.0632	0.5635	0.100*
H18C	0.4250	0.1298	0.4941	0.100*
C19	0.6072 (3)	0.2496 (2)	0.4041 (2)	0.0522 (7)
C20	0.6583 (3)	0.1595 (2)	0.3597 (2)	0.0536 (7)
H20A	0.6346	0.0871	0.3901	0.064*
C21	0.7467 (3)	0.1750 (3)	0.2685 (2)	0.0562 (7)
C22	0.7822 (4)	0.2827 (3)	0.2256 (3)	0.0709 (9)
H22A	0.8426	0.2930	0.1666	0.085*
C23	0.7294 (4)	0.3750 (3)	0.2692 (2)	0.0695 (9)
H23A	0.7531	0.4473	0.2386	0.083*
C24	0.6415 (3)	0.3607 (3)	0.3581 (2)	0.0553 (7)
C25	0.7994 (3)	0.0788 (3)	0.2206 (2)	0.0628 (8)
H25A	0.8595	0.0908	0.1615	0.075*
C26	0.8191 (3)	−0.1072 (3)	0.2028 (2)	0.0521 (7)
C27	0.8563 (3)	−0.2335 (3)	0.2632 (2)	0.0600 (8)
H27A	0.8492	−0.2584	0.3361	0.072*
C28	0.9039 (3)	−0.3226 (3)	0.2161 (3)	0.0638 (8)
H28A	0.9299	−0.4068	0.2579	0.077*
C29	0.9134 (3)	−0.2882 (3)	0.1071 (3)	0.0637 (8)
C30	0.8748 (3)	−0.1628 (3)	0.0483 (3)	0.0700 (9)
H30A	0.8808	−0.1382	−0.0247	0.084*
C31	0.8277 (3)	−0.0725 (3)	0.0934 (2)	0.0616 (8)
H31A	0.8016	0.0115	0.0511	0.074*
C32	0.9638 (4)	−0.3868 (4)	0.0562 (3)	0.0951 (12)
H32A	0.9644	−0.3470	−0.0189	0.143*
H32B	0.8977	−0.4331	0.0753	0.143*
H32C	1.0612	−0.4426	0.0800	0.143*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0888 (16)	0.0727 (14)	0.0692 (15)	−0.0405 (12)	0.0212 (13)	−0.0353 (12)
O2	0.0855 (16)	0.0604 (12)	0.0766 (15)	−0.0309 (11)	0.0077 (13)	−0.0291 (12)
N1	0.0647 (16)	0.0733 (17)	0.0546 (16)	−0.0276 (14)	0.0007 (13)	−0.0239 (14)
C1	0.083 (2)	0.079 (2)	0.064 (2)	−0.0421 (19)	0.0124 (18)	−0.0262 (18)
C2	0.078 (2)	0.071 (2)	0.103 (3)	−0.0294 (18)	−0.006 (2)	−0.039 (2)
C3	0.065 (2)	0.0547 (18)	0.0549 (19)	−0.0182 (15)	−0.0088 (16)	−0.0155 (15)
C4	0.079 (2)	0.065 (2)	0.065 (2)	−0.0329 (17)	0.0000 (19)	−0.0145 (17)
C5	0.082 (2)	0.080 (2)	0.0513 (19)	−0.0373 (19)	0.0063 (17)	−0.0174 (17)
C6	0.069 (2)	0.0673 (19)	0.0460 (17)	−0.0223 (16)	−0.0066 (16)	−0.0175 (15)
C7	0.0627 (19)	0.0593 (18)	0.0534 (19)	−0.0239 (15)	−0.0067 (16)	−0.0149 (15)
C8	0.0638 (19)	0.0568 (17)	0.0465 (17)	−0.0194 (15)	−0.0010 (15)	−0.0177 (15)
C9	0.072 (2)	0.082 (2)	0.0430 (18)	−0.0313 (18)	0.0042 (16)	−0.0216 (17)
C10	0.0565 (19)	0.0662 (18)	0.0445 (17)	−0.0235 (15)	0.0003 (14)	−0.0180 (15)
C11	0.0546 (19)	0.080 (2)	0.061 (2)	−0.0280 (16)	0.0021 (16)	−0.0241 (17)
C12	0.0541 (19)	0.080 (2)	0.063 (2)	−0.0200 (16)	0.0120 (16)	−0.0258 (18)
C13	0.078 (2)	0.071 (2)	0.0435 (17)	−0.0237 (18)	−0.0001 (17)	−0.0194 (16)
C14	0.067 (2)	0.084 (2)	0.061 (2)	−0.0358 (18)	0.0003 (17)	−0.0282 (18)
C15	0.0558 (18)	0.084 (2)	0.0563 (19)	−0.0318 (16)	0.0070 (15)	−0.0254 (17)
C16	0.119 (3)	0.102 (3)	0.077 (3)	−0.036 (2)	0.015 (2)	−0.046 (2)
O3	0.0907 (16)	0.0543 (12)	0.0674 (14)	−0.0357 (11)	0.0120 (12)	−0.0221 (11)
O4	0.0832 (15)	0.0566 (12)	0.0595 (14)	−0.0342 (11)	0.0207 (12)	−0.0237 (10)
N2	0.0576 (15)	0.0620 (15)	0.0515 (15)	−0.0195 (12)	0.0045 (12)	−0.0216 (13)
C17	0.172 (4)	0.069 (2)	0.064 (2)	−0.065 (2)	0.012 (2)	−0.0236 (18)
C18	0.085 (2)	0.0540 (18)	0.058 (2)	−0.0311 (16)	0.0137 (18)	−0.0136 (15)
C19	0.0545 (17)	0.0520 (16)	0.0482 (17)	−0.0224 (13)	0.0028 (14)	−0.0126 (14)
C20	0.0580 (18)	0.0483 (15)	0.0530 (18)	−0.0200 (13)	−0.0011 (15)	−0.0145 (14)
C21	0.0561 (18)	0.0637 (18)	0.0494 (17)	−0.0231 (15)	0.0018 (15)	−0.0187 (15)
C22	0.087 (2)	0.079 (2)	0.056 (2)	−0.0466 (19)	0.0202 (18)	−0.0237 (18)
C23	0.092 (2)	0.068 (2)	0.058 (2)	−0.0460 (19)	0.0091 (19)	−0.0188 (17)
C24	0.0635 (19)	0.0545 (17)	0.0502 (18)	−0.0257 (15)	−0.0024 (15)	−0.0151 (15)
C25	0.064 (2)	0.072 (2)	0.0532 (19)	−0.0241 (16)	0.0066 (16)	−0.0245 (17)
C26	0.0444 (16)	0.0606 (18)	0.0504 (17)	−0.0164 (13)	0.0037 (14)	−0.0214 (15)
C27	0.0542 (18)	0.074 (2)	0.0518 (18)	−0.0234 (15)	0.0014 (15)	−0.0211 (16)
C28	0.0553 (18)	0.0662 (19)	0.070 (2)	−0.0195 (15)	0.0021 (16)	−0.0259 (17)
C29	0.0544 (19)	0.082 (2)	0.067 (2)	−0.0250 (17)	0.0045 (17)	−0.0398 (19)
C30	0.070 (2)	0.091 (2)	0.053 (2)	−0.0255 (19)	−0.0013 (17)	−0.0310 (19)
C31	0.0617 (19)	0.0698 (19)	0.0503 (18)	−0.0208 (15)	−0.0022 (15)	−0.0192 (16)
C32	0.108 (3)	0.098 (3)	0.095 (3)	−0.033 (2)	0.015 (2)	−0.059 (2)

Geometric parameters (Å, º) top

O1—C8	1.374 (3)	O3—C24	1.356 (3)
O1—C1	1.418 (3)	O3—C17	1.414 (3)
O2—C3	1.352 (3)	O4—C19	1.373 (3)
O2—C2	1.440 (3)	O4—C18	1.420 (3)
N1—C9	1.274 (4)	N2—C25	1.270 (3)
N1—C10	1.420 (3)	N2—C26	1.416 (3)
C1—H1B	0.9600	C17—H17A	0.9600
C1—H1C	0.9600	C17—H17B	0.9600
C1—H1D	0.9600	C17—H17C	0.9600
C2—H2A	0.9600	C18—H18A	0.9600
C2—H2B	0.9600	C18—H18B	0.9600
C2—H2C	0.9600	C18—H18C	0.9600
C3—C4	1.377 (4)	C19—C20	1.366 (3)
C3—C8	1.424 (4)	C19—C24	1.416 (4)
C4—C5	1.387 (4)	C20—C21	1.410 (4)
C4—H4A	0.9300	C20—H20A	0.9300
C5—C6	1.381 (4)	C21—C22	1.384 (4)
C5—H5A	0.9300	C21—C25	1.464 (4)
C6—C7	1.412 (4)	C22—C23	1.382 (4)
C6—C9	1.461 (4)	C22—H22A	0.9300
C7—C8	1.372 (4)	C23—C24	1.382 (4)
C7—H7A	0.9300	C23—H23A	0.9300
C9—H9A	0.9300	C25—H25A	0.9300
C10—C11	1.391 (4)	C26—C27	1.389 (4)
C10—C15	1.394 (4)	C26—C31	1.396 (4)
C11—C12	1.370 (4)	C27—C28	1.382 (4)
C11—H11A	0.9300	C27—H27A	0.9300
C12—C13	1.405 (4)	C28—C29	1.392 (4)
C12—H12A	0.9300	C28—H28A	0.9300
C13—C14	1.383 (4)	C29—C30	1.375 (4)
C13—C16	1.507 (4)	C29—C32	1.518 (4)
C14—C15	1.388 (4)	C30—C31	1.376 (4)
C14—H14A	0.9300	C30—H30A	0.9300
C15—H15A	0.9300	C31—H31A	0.9300
C16—H16A	0.9600	C32—H32A	0.9600
C16—H16B	0.9600	C32—H32B	0.9600
C16—H16C	0.9600	C32—H32C	0.9600

C8—O1—C1	117.5 (2)	C24—O3—C17	118.5 (2)
C3—O2—C2	117.9 (3)	C19—O4—C18	117.4 (2)
C9—N1—C10	120.0 (3)	C25—N2—C26	120.0 (3)
O1—C1—H1B	109.5	O3—C17—H17A	109.5
O1—C1—H1C	109.5	O3—C17—H17B	109.5
H1B—C1—H1C	109.5	H17A—C17—H17B	109.5
O1—C1—H1D	109.5	O3—C17—H17C	109.5
H1B—C1—H1D	109.5	H17A—C17—H17C	109.5
H1C—C1—H1D	109.5	H17B—C17—H17C	109.5
O2—C2—H2A	109.5	O4—C18—H18A	109.5
O2—C2—H2B	109.5	O4—C18—H18B	109.5
H2A—C2—H2B	109.5	H18A—C18—H18B	109.5
O2—C2—H2C	109.5	O4—C18—H18C	109.5
H2A—C2—H2C	109.5	H18A—C18—H18C	109.5
H2B—C2—H2C	109.5	H18B—C18—H18C	109.5
O2—C3—C4	125.5 (3)	C20—C19—O4	125.7 (3)
O2—C3—C8	115.1 (3)	C20—C19—C24	120.1 (3)
C4—C3—C8	119.3 (3)	O4—C19—C24	114.2 (2)
C3—C4—C5	120.2 (3)	C19—C20—C21	120.7 (3)
C3—C4—H4A	119.9	C19—C20—H20A	119.7
C5—C4—H4A	119.9	C21—C20—H20A	119.7
C6—C5—C4	121.3 (3)	C22—C21—C20	118.6 (3)
C6—C5—H5A	119.4	C22—C21—C25	121.0 (3)
C4—C5—H5A	119.4	C20—C21—C25	120.4 (3)
C5—C6—C7	118.9 (3)	C23—C22—C21	121.0 (3)
C5—C6—C9	120.7 (3)	C23—C22—H22A	119.5
C7—C6—C9	120.4 (3)	C21—C22—H22A	119.5
C8—C7—C6	120.4 (3)	C22—C23—C24	120.5 (3)
C8—C7—H7A	119.8	C22—C23—H23A	119.8
C6—C7—H7A	119.8	C24—C23—H23A	119.8
C7—C8—O1	125.4 (3)	O3—C24—C23	125.7 (3)
C7—C8—C3	119.9 (3)	O3—C24—C19	115.3 (3)
O1—C8—C3	114.7 (3)	C23—C24—C19	119.0 (3)
N1—C9—C6	123.8 (3)	N2—C25—C21	123.4 (3)
N1—C9—H9A	118.1	N2—C25—H25A	118.3
C6—C9—H9A	118.1	C21—C25—H25A	118.3
C11—C10—C15	118.2 (3)	C27—C26—C31	118.3 (3)
C11—C10—N1	125.5 (3)	C27—C26—N2	118.1 (3)
C15—C10—N1	116.3 (3)	C31—C26—N2	123.6 (3)
C12—C11—C10	121.0 (3)	C28—C27—C26	120.8 (3)
C12—C11—H11A	119.5	C28—C27—H27A	119.6
C10—C11—H11A	119.5	C26—C27—H27A	119.6
C11—C12—C13	121.6 (3)	C27—C28—C29	121.0 (3)
C11—C12—H12A	119.2	C27—C28—H28A	119.5
C13—C12—H12A	119.2	C29—C28—H28A	119.5
C14—C13—C12	117.0 (3)	C30—C29—C28	117.6 (3)
C14—C13—C16	121.0 (3)	C30—C29—C32	121.9 (3)
C12—C13—C16	122.0 (3)	C28—C29—C32	120.5 (3)
C13—C14—C15	121.9 (3)	C29—C30—C31	122.5 (3)
C13—C14—H14A	119.0	C29—C30—H30A	118.8
C15—C14—H14A	119.0	C31—C30—H30A	118.8
C14—C15—C10	120.3 (3)	C30—C31—C26	119.9 (3)
C14—C15—H15A	119.9	C30—C31—H31A	120.1
C10—C15—H15A	119.9	C26—C31—H31A	120.1
C13—C16—H16A	109.5	C29—C32—H32A	109.5
C13—C16—H16B	109.5	C29—C32—H32B	109.5
H16A—C16—H16B	109.5	H32A—C32—H32B	109.5
C13—C16—H16C	109.5	C29—C32—H32C	109.5
H16A—C16—H16C	109.5	H32A—C32—H32C	109.5
H16B—C16—H16C	109.5	H32B—C32—H32C	109.5

C2—O2—C3—C4	−6.4 (4)	C18—O4—C19—C20	−1.6 (4)
C2—O2—C3—C8	173.8 (3)	C18—O4—C19—C24	178.6 (2)
O2—C3—C4—C5	179.1 (3)	O4—C19—C20—C21	−179.1 (3)
C8—C3—C4—C5	−1.1 (5)	C24—C19—C20—C21	0.6 (4)
C3—C4—C5—C6	0.3 (5)	C19—C20—C21—C22	0.9 (4)
C4—C5—C6—C7	0.4 (5)	C19—C20—C21—C25	−179.2 (3)
C4—C5—C6—C9	−178.4 (3)	C20—C21—C22—C23	−1.8 (5)
C5—C6—C7—C8	−0.1 (4)	C25—C21—C22—C23	178.3 (3)
C9—C6—C7—C8	178.6 (3)	C21—C22—C23—C24	1.1 (5)
C6—C7—C8—O1	−179.6 (3)	C17—O3—C24—C23	7.8 (4)
C6—C7—C8—C3	−0.8 (4)	C17—O3—C24—C19	−172.9 (3)
C1—O1—C8—C7	6.1 (4)	C22—C23—C24—O3	179.7 (3)
C1—O1—C8—C3	−172.8 (3)	C22—C23—C24—C19	0.4 (5)
O2—C3—C8—C7	−178.8 (2)	C20—C19—C24—O3	179.4 (2)
C4—C3—C8—C7	1.4 (4)	O4—C19—C24—O3	−0.8 (4)
O2—C3—C8—O1	0.2 (4)	C20—C19—C24—C23	−1.2 (4)
C4—C3—C8—O1	−179.6 (3)	O4—C19—C24—C23	178.5 (3)
C10—N1—C9—C6	−177.7 (2)	C26—N2—C25—C21	178.0 (2)
C5—C6—C9—N1	177.5 (3)	C22—C21—C25—N2	−178.5 (3)
C7—C6—C9—N1	−1.2 (5)	C20—C21—C25—N2	1.6 (4)
C9—N1—C10—C11	27.7 (4)	C25—N2—C26—C27	145.1 (3)
C9—N1—C10—C15	−154.0 (3)	C25—N2—C26—C31	−38.2 (4)
C15—C10—C11—C12	0.6 (4)	C31—C26—C27—C28	1.5 (4)
N1—C10—C11—C12	179.0 (3)	N2—C26—C27—C28	178.4 (3)
C10—C11—C12—C13	0.1 (5)	C26—C27—C28—C29	−1.1 (4)
C11—C12—C13—C14	0.0 (5)	C27—C28—C29—C30	0.5 (4)
C11—C12—C13—C16	−179.3 (3)	C27—C28—C29—C32	−179.2 (3)
C12—C13—C14—C15	−0.9 (5)	C28—C29—C30—C31	−0.2 (5)
C16—C13—C14—C15	178.4 (3)	C32—C29—C30—C31	179.4 (3)
C13—C14—C15—C10	1.7 (5)	C29—C30—C31—C26	0.6 (5)
C11—C10—C15—C14	−1.5 (4)	C27—C26—C31—C30	−1.2 (4)
N1—C10—C15—C14	−180.0 (3)	N2—C26—C31—C30	−177.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ⁱ	0.96	2.52	3.439 (4)	161
C17—H17A···O4ⁱⁱ	0.96	2.51	3.459 (4)	169

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇NO₂
M_r	255.31
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.777 (2), 12.304 (3), 13.716 (3)
α, β, γ (°)	67.84 (3), 81.97 (3), 68.41 (3)
V (Å³)	1420.9 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.54 × 0.34 × 0.18

Data collection
Diffractometer	Bruker P4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6427, 6059, 2536
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.229, 1.01
No. of reflections	6059
No. of parameters	343
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.22

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ⁱ	0.96	2.52	3.439 (4)	161
C17—H17A···O4ⁱⁱ	0.96	2.51	3.459 (4)	169

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

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