Methyl [(1E)-(4-methoxy­phen­yl)methyl­eneamino]acetate

In the title compound, C₁₁H₁₃NO₃, the methoxy­carbonyl group is rotated out of the plane of the 4-methoxy­benzyl group. The conformation found in the crystal structure differs from that computed in vacuo, where the two groups are coplanar. The crystal structure is stabilized by van der Waals inter­actions and weak inter­actions of the C—H...O type.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.050
• wR factor = 0.145
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96

Alert level C
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.84
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           69.09
           From the CIF: _reflns_number_total               1911
           From the CIF: _diffrn_reflns_limit_ max hkl   12.    9.   14.
           From the CIF: _diffrn_reflns_limit_ min hkl   -1.   -1.  -14.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   14.    9.   14.
           Calculated minimum hkl  -14.   -9.  -14.
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
   1 ALERT level B = Potentially serious problem
   2 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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

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Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PLATON (Spek, 2003).

Methyl [(1E)-(4-methoxyphenyl)methyleneamino]acetate

Crystal data

C11H13NO3	F(000) = 440
Mr = 207.22	Dx = 1.290 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 38 reflections
a = 11.6716 (4) Å	θ = 12.8–28.0°
b = 7.6043 (3) Å	µ = 0.78 mm^−1
c = 12.0400 (4) Å	T = 293 K
β = 92.776 (4)°	Prism, colourless
V = 1067.35 (7) Å^3	0.52 × 0.33 × 0.24 mm
Z = 4

Data collection

Siemens P4 four-circle diffractometer	1650 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 69.1°, θmin = 3.8°
ω/2θ scans	h = −1→12
Absorption correction: ψ scan (North et al., 1968) (XEMP; Siemens, 1989)	k = −1→9
Tmin = 0.585, Tmax = 0.829	l = −14→14
2565 measured reflections	3 standard reflections every 100 reflections
1911 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.145	w = 1/[σ^2(Fo^2) + (0.0752P)^2 + 0.2269P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
1911 reflections	Δρmax = 0.21 e Å^−3
139 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0139 (16)

Special details

Experimental. Spectroscopic analysis: ¹H NMR (CDCl₃): δ 9.58 (s, 1H, H8), 7.61 (δ, 2H, H4, H6, J = 7.9 Hz), 7.15 (δ, 2H, H3, H7, J = 7.9 Hz), 4.28 (s, 2H, CH2), 3.70 (s, 3H, CH3), 3.56 (s, 3H, CH3). ¹³C NMR (CDCl₃): δ 170.7 (C11), 160.2 (C8), 157.8 (C2), 134.7 (C5), 129.2 (C4, C6), 113.7 (C3, C7), 55.3 (OCH3), 50.7 (OCH3), 49.8 (C9).

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.90522 (11)	0.02030 (19)	0.39624 (10)	0.0578 (4)
O2	0.52528 (14)	0.1912 (3)	−0.22099 (12)	0.0843 (6)
O3	0.59595 (11)	0.13487 (19)	−0.38580 (10)	0.0580 (4)
N1	0.71075 (14)	0.0137 (2)	−0.11336 (13)	0.0598 (5)
C1	0.82631 (18)	−0.0488 (3)	0.47142 (16)	0.0651 (6)
H1A	0.7581	0.0219	0.4687	0.098*
H1B	0.8606	−0.0473	0.5455	0.098*
H1C	0.8070	−0.1674	0.4508	0.098*
C2	0.87198 (14)	0.0284 (2)	0.28618 (14)	0.0450 (4)
C3	0.76931 (15)	−0.0370 (2)	0.24016 (15)	0.0486 (4)
H3	0.7167	−0.0897	0.2853	0.058*
C4	0.74559 (15)	−0.0237 (2)	0.12688 (15)	0.0495 (4)
H4	0.6772	−0.0695	0.0964	0.059*
C5	0.82184 (14)	0.0569 (2)	0.05747 (14)	0.0453 (4)
C6	0.92327 (15)	0.1244 (2)	0.10591 (15)	0.0526 (5)
H6	0.9749	0.1802	0.0612	0.063*
C7	0.94893 (15)	0.1106 (3)	0.21815 (15)	0.0532 (5)
H7	1.0175	0.1559	0.2486	0.064*
C8	0.79928 (15)	0.0714 (2)	−0.06285 (15)	0.0489 (4)
H8	0.8540	0.1267	−0.1043	0.059*
C10	0.59766 (15)	0.1282 (3)	−0.27568 (14)	0.0510 (4)
C9	0.70328 (18)	0.0325 (3)	−0.23331 (16)	0.0580 (5)
H9A	0.7041	−0.0835	−0.2669	0.070*
H9B	0.7704	0.0954	−0.2564	0.070*
C11	0.50316 (17)	0.2307 (4)	−0.44114 (17)	0.0712 (6)
H11A	0.4338	0.1631	−0.4392	0.107*
H11B	0.5208	0.2518	−0.5170	0.107*
H11C	0.4930	0.3410	−0.4041	0.107*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0466 (8)	0.0754 (9)	0.0510 (7)	−0.0036 (6)	−0.0008 (5)	0.0014 (6)
O2	0.0760 (11)	0.1250 (15)	0.0534 (8)	0.0263 (10)	0.0181 (7)	−0.0003 (8)
O3	0.0536 (8)	0.0777 (9)	0.0431 (6)	0.0085 (6)	0.0058 (5)	0.0029 (6)
N1	0.0599 (10)	0.0685 (10)	0.0507 (8)	−0.0118 (8)	0.0000 (7)	0.0101 (7)
C1	0.0641 (13)	0.0805 (14)	0.0513 (10)	−0.0067 (10)	0.0072 (9)	0.0044 (10)
C2	0.0374 (9)	0.0471 (9)	0.0506 (9)	0.0048 (6)	0.0019 (7)	−0.0013 (7)
C3	0.0407 (10)	0.0507 (9)	0.0548 (10)	−0.0056 (7)	0.0062 (7)	0.0037 (7)
C4	0.0397 (10)	0.0533 (10)	0.0553 (10)	−0.0079 (7)	−0.0001 (7)	0.0022 (7)
C5	0.0397 (9)	0.0438 (8)	0.0528 (9)	0.0013 (7)	0.0047 (7)	0.0021 (7)
C6	0.0391 (10)	0.0586 (10)	0.0607 (10)	−0.0052 (7)	0.0086 (7)	0.0049 (8)
C7	0.0342 (9)	0.0648 (11)	0.0606 (10)	−0.0057 (7)	0.0010 (7)	−0.0017 (8)
C8	0.0455 (10)	0.0477 (9)	0.0539 (10)	0.0025 (7)	0.0066 (7)	0.0062 (7)
C10	0.0505 (10)	0.0580 (10)	0.0452 (8)	−0.0065 (8)	0.0086 (7)	0.0016 (8)
C9	0.0629 (12)	0.0612 (11)	0.0499 (10)	0.0016 (9)	0.0026 (8)	0.0028 (8)
C11	0.0521 (12)	0.1018 (17)	0.0595 (11)	0.0100 (11)	0.0012 (9)	0.0135 (11)

Geometric parameters (Å, º)

O1—C2	1.364 (2)	C4—C5	1.392 (2)
O1—C1	1.423 (2)	C4—H4	0.9300
O2—C10	1.196 (2)	C5—C6	1.392 (3)
O3—C10	1.326 (2)	C5—C8	1.464 (2)
O3—C11	1.442 (2)	C6—C7	1.374 (3)
N1—C8	1.253 (2)	C6—H6	0.9300
N1—C9	1.450 (2)	C7—H7	0.9300
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600	C10—C9	1.500 (3)
C1—H1C	0.9600	C9—H9A	0.9700
C2—C3	1.388 (3)	C9—H9B	0.9700
C2—C7	1.392 (3)	C11—H11A	0.9600
C3—C4	1.382 (2)	C11—H11B	0.9600
C3—H3	0.9300	C11—H11C	0.9600
C2—O1—C1	118.18 (15)	C5—C6—H6	119.2
C10—O3—C11	117.13 (14)	C6—C7—C2	119.79 (16)
C8—N1—C9	117.23 (16)	C6—C7—H7	120.1
O1—C1—H1A	109.5	C2—C7—H7	120.1
O1—C1—H1B	109.5	N1—C8—C5	123.97 (16)
H1A—C1—H1B	109.5	N1—C8—H8	118.0
O1—C1—H1C	109.5	C5—C8—H8	118.0
H1A—C1—H1C	109.5	O2—C10—O3	123.94 (18)
H1B—C1—H1C	109.5	O2—C10—C9	126.73 (17)
O1—C2—C3	124.82 (16)	O3—C10—C9	109.32 (15)
O1—C2—C7	115.50 (15)	N1—C9—C10	113.29 (16)
C3—C2—C7	119.67 (16)	N1—C9—H9A	108.9
C4—C3—C2	119.69 (16)	C10—C9—H9A	108.9
C4—C3—H3	120.2	N1—C9—H9B	108.9
C2—C3—H3	120.2	C10—C9—H9B	108.9
C3—C4—C5	121.43 (16)	H9A—C9—H9B	107.7
C3—C4—H4	119.3	O3—C11—H11A	109.5
C5—C4—H4	119.3	O3—C11—H11B	109.5
C4—C5—C6	117.78 (16)	H11A—C11—H11B	109.5
C4—C5—C8	122.51 (16)	O3—C11—H11C	109.5
C6—C5—C8	119.70 (16)	H11A—C11—H11C	109.5
C7—C6—C5	121.62 (16)	H11B—C11—H11C	109.5
C7—C6—H6	119.2
C1—O1—C2—C3	−4.7 (2)	C2—C3—C4—C5	−1.1 (2)
C1—O1—C2—C7	174.8 (2)	C3—C4—C5—C6	−0.1 (2)
C11—O3—C10—O2	2.7 (3)	C3—C4—C5—C8	179.5 (2)
C11—O3—C10—C9	−176.8 (2)	C4—C5—C8—N1	0.1 (3)
C9—N1—C8—C5	−177.7 (2)	C6—C5—C8—N1	179.6 (2)
C8—N1—C9—C10	−124.2 (2)	C8—C5—C6—C7	−178.7 (2)
C7—C2—C3—C4	1.5 (2)	C4—C5—C6—C7	0.9 (3)
O1—C2—C7—C6	179.7 (2)	C5—C6—C7—C2	−0.4 (3)
O1—C2—C3—C4	−179.0 (2)	N1—C9—C10—O3	−178.1 (2)
C3—C2—C7—C6	−0.8 (3)	N1—C9—C10—O2	2.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O2^i	0.96	2.50	3.443 (3)	169

Symmetry code: (i) x, −y+1/2, z−1/2.