Ethanaminium 3,4,5,6-tetra­bromo-2-(meth­oxy­carbon­yl)benzoate methanol monosolvate

Li, J.

doi:10.1107/S1600536810052591

organic compounds

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Volume 67| Part 1| January 2011| Page o200

https://doi.org/10.1107/S1600536810052591

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Ethanaminium 3,4,5,6-tetrabromo-2-(methoxycarbonyl)benzoate methanol monosolvate

Jian Li ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ljwfu@163.com

(Received 10 December 2010; accepted 15 December 2010; online 18 December 2010)

In the crystal structure of the title compound, C₂H₈N⁺·C₉H₃Br₄O₄⁻·CH₄O, intermolecular N—H⋯O and O—H⋯O hydrogen bonds link the components into chains along [001]. Additional stabilization is supplied by weak C—H⋯O and C—H⋯Br interactions.

Related literature

For a related structure, see: Liang (2008 ).

Experimental

Crystal data

C₂H₈N⁺·C₉H₃Br₄O₄⁻·CH₄O
M_r = 572.89
Monoclinic, P 2₁ /c
a = 9.4651 (8) Å
b = 25.6544 (19) Å
c = 8.3365 (6) Å
β = 112.787 (1)°
V = 1866.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 8.64 mm⁻¹
T = 298 K
0.40 × 0.35 × 0.33 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.130, T_max = 0.163
9436 measured reflections
3295 independent reflections
1454 reflections with I > 2σ(I)
R_int = 0.086

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.068
S = 0.99
3295 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4ⁱ	0.89	1.94	2.772 (9)	155
N1—H1B⋯O5	0.89	1.92	2.810 (9)	174
N1—H1C⋯O3ⁱⁱ	0.89	1.99	2.871 (7)	170
N1—H1C⋯O4ⁱⁱ	0.89	2.58	3.249 (8)	132
O5—H5⋯O3	0.82	1.90	2.705 (8)	165
C10—H10A⋯Br3ⁱⁱⁱ	0.97	2.92	3.736 (8)	143
C11—H11B⋯O2^iv	0.96	2.47	3.357 (10)	153
Symmetry codes: (i) x, y, z+1; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+2, -z+1; (iv) x-1, y, z.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810052591/lh5189sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810052591/lh5189Isup2.hkl

checkCIF report

Comment top

4,5,6,7-Tetrabromo-2-ethylisoindoline-1,3-dione is an important flame retardant. 2-(Methoxycarbonyl)-3,4,5,6-tetrabromobenzoic acid is an intermediate in the sytnthesis of this flame retardant. In this paper, the structure of the title compound is reported. The asymmetric unit of the title compound (I) contains one ethanaminium cation, one 2-(methoxycarbonyl)-3,4,5,6-tetrabromobenzoate anion and one methanol solvent molecule (Fig. 1). The bond lengths and angles agree with those in ethane-1,2-diaminium 2-(methoxycarbonyl)-3,4,5,6-tetrabromo benzoate methanol solvate (Liang, 2008). In the crystal structure, intermolecular N—H···O and O—H···O hydrogen bonds link the components of the structure into one-dimensional chains along [001](see fig. 2). Additional stabilization is supplied by weak C—H···O and C—H···Br interactions.

Related literature top

For a related structure, see: Liang (2008).

Experimental top

A mixture of 4,5,6,7-tetrabromoisobenzofuran-1,3-dione (4.64 g, 0.01 mol) and methanol (15 ml) was refluxed for 0.5 h. And then ethanamine (0.45 g, 0.01 mol) was added to the above solution, and mixed for 10 min at room temperature. The solution was kept at room temperature for 3 d. Natural evaporation gave colourless single crystals of the title compound, suitable for X-ray analysis.

Structure description top

For a related structure, see: Liang (2008).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I), drawn with 30% probability ellipsoids.
	Fig. 2. The crystal packing of (I). Hydrogen bonds are indicated by dashed lines.

Ethanaminium 3,4,5,6-tetrabromo-2-(methoxycarbonyl)benzoate methanol monosolvate top

Crystal data top

C₂H₈N⁺·C₉H₃Br₄O₄⁻·CH₄O	F(000) = 1096
M_r = 572.89	D_x = 2.039 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1513 reflections
a = 9.4651 (8) Å	θ = 2.3–20.6°
b = 25.6544 (19) Å	µ = 8.64 mm⁻¹
c = 8.3365 (6) Å	T = 298 K
β = 112.787 (1)°	Block, colorless
V = 1866.3 (2) Å³	0.40 × 0.35 × 0.33 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3295 independent reflections
Radiation source: fine-focus sealed tube	1454 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
φ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→11
T_min = 0.130, T_max = 0.163	k = −30→30
9436 measured reflections	l = −9→8

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.068	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0024P)²] where P = (F_o² + 2F_c²)/3
3295 reflections	(Δ/σ)_max = 0.001
200 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₂H₈N⁺·C₉H₃Br₄O₄⁻·CH₄O	V = 1866.3 (2) Å³
M_r = 572.89	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4651 (8) Å	µ = 8.64 mm⁻¹
b = 25.6544 (19) Å	T = 298 K
c = 8.3365 (6) Å	0.40 × 0.35 × 0.33 mm
β = 112.787 (1)°

Data collection top

Bruker SMART CCD diffractometer	3295 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	1454 reflections with I > 2σ(I)
T_min = 0.130, T_max = 0.163	R_int = 0.086
9436 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.068	H-atom parameters constrained
S = 0.99	Δρ_max = 0.49 e Å⁻³
3295 reflections	Δρ_min = −0.51 e Å⁻³
200 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
Br1	0.32729 (8)	0.90633 (3)	0.26426 (13)	0.0702 (3)
Br2	0.40752 (9)	1.03175 (3)	0.25156 (12)	0.0705 (3)
Br3	0.73585 (10)	1.06551 (3)	0.23297 (14)	0.0807 (3)
Br4	0.98266 (9)	0.97499 (3)	0.23443 (13)	0.0773 (3)
N1	0.5436 (6)	0.7996 (2)	0.8034 (8)	0.0546 (19)
H1A	0.5376	0.8133	0.8986	0.082*
H1B	0.6186	0.8151	0.7820	0.082*
H1C	0.5631	0.7656	0.8196	0.082*
O1	0.8313 (6)	0.8333 (2)	0.1273 (8)	0.0672 (18)
O2	0.9937 (7)	0.8565 (2)	0.3871 (9)	0.101 (3)
O3	0.6431 (6)	0.8063 (2)	0.3863 (8)	0.076 (2)
O4	0.4945 (6)	0.8125 (2)	0.1079 (8)	0.0713 (19)
O5	0.7663 (7)	0.8481 (2)	0.7090 (7)	0.104 (2)
H5	0.7413	0.8383	0.6081	0.157*
C1	0.8783 (9)	0.8620 (3)	0.2667 (14)	0.050 (3)
C2	0.5820 (10)	0.8306 (3)	0.2499 (14)	0.050 (3)
C3	0.7630 (7)	0.9042 (3)	0.2521 (9)	0.0369 (19)
C4	0.6200 (8)	0.8886 (3)	0.2517 (9)	0.040 (2)
C5	0.5158 (7)	0.9276 (3)	0.2534 (9)	0.040 (2)
C6	0.5515 (7)	0.9794 (3)	0.2527 (9)	0.047 (2)
C7	0.6915 (8)	0.9947 (3)	0.2450 (10)	0.045 (2)
C8	0.7960 (7)	0.9565 (3)	0.2469 (9)	0.040 (2)
C9	0.9329 (9)	0.7886 (3)	0.1323 (11)	0.097 (3)
H9A	1.0367	0.8006	0.1685	0.146*
H9B	0.9010	0.7734	0.0185	0.146*
H9C	0.9266	0.7629	0.2131	0.146*
C10	0.3935 (9)	0.8076 (3)	0.6508 (10)	0.056 (2)
H10A	0.3730	0.8447	0.6333	0.068*
H10B	0.4018	0.7937	0.5466	0.068*
C11	0.2643 (8)	0.7820 (3)	0.6773 (10)	0.081 (3)
H11A	0.2763	0.7449	0.6766	0.121*
H11B	0.1697	0.7919	0.5854	0.121*
H11C	0.2630	0.7926	0.7872	0.121*
C12	0.8988 (9)	0.8774 (3)	0.7572 (12)	0.104 (4)
H12A	0.9141	0.8959	0.8627	0.155*
H12B	0.8899	0.9019	0.6667	0.155*
H12C	0.9844	0.8548	0.7757	0.155*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0399 (5)	0.0808 (7)	0.1016 (9)	−0.0038 (5)	0.0403 (6)	0.0061 (6)
Br2	0.0615 (6)	0.0617 (6)	0.0956 (8)	0.0286 (5)	0.0386 (6)	0.0063 (6)
Br3	0.0898 (7)	0.0337 (5)	0.1331 (10)	−0.0058 (5)	0.0592 (7)	−0.0010 (6)
Br4	0.0455 (6)	0.0699 (7)	0.1306 (10)	−0.0122 (5)	0.0496 (6)	−0.0070 (6)
N1	0.061 (5)	0.042 (4)	0.072 (6)	−0.011 (3)	0.039 (4)	0.000 (4)
O1	0.057 (4)	0.063 (4)	0.077 (5)	0.027 (3)	0.022 (4)	−0.014 (4)
O2	0.068 (4)	0.114 (6)	0.085 (6)	0.048 (4)	−0.011 (4)	−0.033 (4)
O3	0.101 (5)	0.044 (4)	0.070 (5)	−0.006 (3)	0.020 (4)	0.019 (4)
O4	0.094 (5)	0.062 (4)	0.062 (5)	−0.038 (3)	0.035 (4)	−0.021 (4)
O5	0.101 (5)	0.150 (6)	0.074 (6)	−0.064 (4)	0.048 (4)	−0.018 (4)
C1	0.036 (6)	0.042 (6)	0.072 (9)	0.003 (5)	0.020 (6)	−0.009 (6)
C2	0.047 (6)	0.036 (6)	0.075 (9)	−0.006 (5)	0.035 (6)	−0.005 (6)
C3	0.031 (4)	0.028 (4)	0.057 (6)	−0.003 (4)	0.023 (4)	−0.005 (5)
C4	0.043 (5)	0.032 (5)	0.043 (6)	0.007 (4)	0.017 (5)	−0.002 (4)
C5	0.026 (4)	0.038 (5)	0.060 (6)	−0.007 (4)	0.021 (4)	−0.004 (5)
C6	0.035 (5)	0.045 (6)	0.058 (6)	0.014 (4)	0.016 (5)	−0.001 (4)
C7	0.032 (5)	0.033 (5)	0.068 (6)	−0.003 (4)	0.019 (5)	0.003 (4)
C8	0.016 (4)	0.041 (5)	0.062 (6)	−0.001 (4)	0.014 (4)	−0.002 (5)
C9	0.090 (7)	0.080 (7)	0.106 (9)	0.045 (6)	0.022 (6)	−0.025 (6)
C10	0.077 (6)	0.046 (6)	0.040 (6)	0.018 (5)	0.015 (6)	0.009 (5)
C11	0.052 (6)	0.097 (7)	0.085 (8)	−0.013 (5)	0.017 (6)	0.016 (6)
C12	0.082 (7)	0.100 (8)	0.144 (10)	−0.050 (6)	0.060 (7)	−0.030 (7)

Geometric parameters (Å, º) top

Br1—C5	1.902 (6)	C3—C4	1.411 (8)
Br2—C6	1.911 (6)	C4—C5	1.410 (8)
Br3—C7	1.876 (6)	C5—C6	1.370 (8)
Br4—C8	1.871 (6)	C6—C7	1.408 (7)
N1—C10	1.509 (8)	C7—C8	1.389 (8)
N1—H1A	0.8900	C9—H9A	0.9600
N1—H1B	0.8900	C9—H9B	0.9600
N1—H1C	0.8900	C9—H9C	0.9600
O1—C1	1.301 (9)	C10—C11	1.478 (8)
O1—C9	1.487 (7)	C10—H10A	0.9700
O2—C1	1.171 (9)	C10—H10B	0.9700
O3—C2	1.227 (9)	C11—H11A	0.9600
O4—C2	1.241 (9)	C11—H11B	0.9600
O5—C12	1.381 (7)	C11—H11C	0.9600
O5—H5	0.8200	C12—H12A	0.9600
C1—C3	1.507 (9)	C12—H12B	0.9600
C2—C4	1.530 (9)	C12—H12C	0.9600
C3—C8	1.381 (7)

C10—N1—H1A	109.5	C6—C7—Br3	120.5 (5)
C10—N1—H1B	109.5	C3—C8—C7	121.2 (6)
H1A—N1—H1B	109.5	C3—C8—Br4	118.6 (5)
C10—N1—H1C	109.5	C7—C8—Br4	120.2 (5)
H1A—N1—H1C	109.5	O1—C9—H9A	109.5
H1B—N1—H1C	109.5	O1—C9—H9B	109.5
C1—O1—C9	114.7 (6)	H9A—C9—H9B	109.5
C12—O5—H5	109.5	O1—C9—H9C	109.5
O2—C1—O1	125.5 (8)	H9A—C9—H9C	109.5
O2—C1—C3	124.2 (9)	H9B—C9—H9C	109.5
O1—C1—C3	110.4 (7)	C11—C10—N1	112.1 (6)
O3—C2—O4	126.6 (8)	C11—C10—H10A	109.2
O3—C2—C4	117.4 (8)	N1—C10—H10A	109.2
O4—C2—C4	116.0 (8)	C11—C10—H10B	109.2
C8—C3—C4	120.3 (6)	N1—C10—H10B	109.2
C8—C3—C1	122.3 (6)	H10A—C10—H10B	107.9
C4—C3—C1	117.4 (6)	C10—C11—H11A	109.5
C5—C4—C3	118.2 (6)	C10—C11—H11B	109.5
C5—C4—C2	121.9 (7)	H11A—C11—H11B	109.5
C3—C4—C2	119.9 (6)	C10—C11—H11C	109.5
C6—C5—C4	121.0 (6)	H11A—C11—H11C	109.5
C6—C5—Br1	121.0 (5)	H11B—C11—H11C	109.5
C4—C5—Br1	118.0 (5)	O5—C12—H12A	109.5
C5—C6—C7	120.6 (6)	O5—C12—H12B	109.5
C5—C6—Br2	120.3 (5)	H12A—C12—H12B	109.5
C7—C6—Br2	119.0 (6)	O5—C12—H12C	109.5
C8—C7—C6	118.8 (6)	H12A—C12—H12C	109.5
C8—C7—Br3	120.8 (5)	H12B—C12—H12C	109.5

C9—O1—C1—O2	3.5 (13)	C2—C4—C5—Br1	2.8 (10)
C9—O1—C1—C3	−176.8 (6)	C4—C5—C6—C7	1.9 (11)
O2—C1—C3—C8	64.3 (12)	Br1—C5—C6—C7	179.9 (5)
O1—C1—C3—C8	−115.3 (8)	C4—C5—C6—Br2	179.1 (5)
O2—C1—C3—C4	−112.9 (10)	Br1—C5—C6—Br2	−2.9 (9)
O1—C1—C3—C4	67.5 (9)	C5—C6—C7—C8	−3.2 (11)
C8—C3—C4—C5	−2.7 (10)	Br2—C6—C7—C8	179.6 (6)
C1—C3—C4—C5	174.6 (7)	C5—C6—C7—Br3	177.0 (6)
C8—C3—C4—C2	177.5 (7)	Br2—C6—C7—Br3	−0.2 (8)
C1—C3—C4—C2	−5.3 (11)	C4—C3—C8—C7	1.4 (11)
O3—C2—C4—C5	−104.5 (9)	C1—C3—C8—C7	−175.7 (8)
O4—C2—C4—C5	77.2 (10)	C4—C3—C8—Br4	−176.4 (5)
O3—C2—C4—C3	75.3 (10)	C1—C3—C8—Br4	6.4 (11)
O4—C2—C4—C3	−103.0 (8)	C6—C7—C8—C3	1.5 (11)
C3—C4—C5—C6	1.0 (10)	Br3—C7—C8—C3	−178.7 (5)
C2—C4—C5—C6	−179.1 (7)	C6—C7—C8—Br4	179.3 (5)
C3—C4—C5—Br1	−177.0 (5)	Br3—C7—C8—Br4	−0.9 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.89	1.94	2.772 (9)	155
N1—H1B···O5	0.89	1.92	2.810 (9)	174
N1—H1C···O3ⁱⁱ	0.89	1.99	2.871 (7)	170
N1—H1C···O4ⁱⁱ	0.89	2.58	3.249 (8)	132
O5—H5···O3	0.82	1.90	2.705 (8)	165
C10—H10A···Br3ⁱⁱⁱ	0.97	2.92	3.736 (8)	143
C11—H11B···O2^iv	0.96	2.47	3.357 (10)	153

Symmetry codes: (i) x, y, z+1; (ii) x, −y+3/2, z+1/2; (iii) −x+1, −y+2, −z+1; (iv) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂H₈N⁺·C₉H₃Br₄O₄⁻·CH₄O
M_r	572.89
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.4651 (8), 25.6544 (19), 8.3365 (6)
β (°)	112.787 (1)
V (Å³)	1866.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	8.64
Crystal size (mm)	0.40 × 0.35 × 0.33

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.130, 0.163
No. of measured, independent and observed [I > 2σ(I)] reflections	9436, 3295, 1454
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.068, 0.99
No. of reflections	3295
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.51

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.89	1.94	2.772 (9)	155
N1—H1B···O5	0.89	1.92	2.810 (9)	174
N1—H1C···O3ⁱⁱ	0.89	1.99	2.871 (7)	170
N1—H1C···O4ⁱⁱ	0.89	2.58	3.249 (8)	132
O5—H5···O3	0.82	1.90	2.705 (8)	165
C10—H10A···Br3ⁱⁱⁱ	0.97	2.92	3.736 (8)	143
C11—H11B···O2^iv	0.96	2.47	3.357 (10)	153

Symmetry codes: (i) x, y, z+1; (ii) x, −y+3/2, z+1/2; (iii) −x+1, −y+2, −z+1; (iv) x−1, y, z.

Acknowledgements

The author thanks Shandong Provincial Natural Science Foundation, China (ZR2009BL027) for support.

References

Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liang, Z.-P. (2008). Acta Cryst. E64, o2416. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethanaminium 3,4,5,6-tetra­bromo-2-(meth­­oxy­carbon­yl)benzoate methanol monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethanaminium 3,4,5,6-tetrabromo-2-(methoxycarbonyl)benzoate methanol monosolvate