(2-Acryloylamino­phen­yl)arsonic acid

The geometrical paramaters for the title compound, C₉H₁₀AsNO₄ or [As(C₉H₈NO)O(OH)₂], are normal. The dihedral angle between the benzene ring and the acrylamide group is 12.2 (2)°. A network of hydrogen bonds leads to a chain structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.038
• wR factor = 0.088
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      24.00 Deg.

Author Response: In view of the size of the crystal (0.14 X 0.11 X 0.07 mm) giving a poor diffracting sample, data were limited to 24.00 Deg.

Alert level B
THETM01_ALERT_3_B  The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5723
PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6].....      24.00 Deg.

Alert level C
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.90
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O3     -   H3     ...       1.03 Ang.

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

   2 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
   6 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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

(I)

Crystal data

C9H10AsNO4	Z = 2
Mr = 271.10	F(000) = 272
Triclinic, P1	Dx = 1.724 Mg m^−3
Hall symbol: -P 1	Melting point: > 573 K K
a = 8.2088 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3132 (4) Å	Cell parameters from 1641 reflections
c = 8.5259 (5) Å	θ = 2.5–24.0°
α = 99.432 (1)°	µ = 3.25 mm^−1
β = 97.766 (1)°	T = 293 K
γ = 111.390 (1)°	Prism, colorless
V = 522.25 (5) Å^3	0.14 × 0.11 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1641 independent reflections
Radiation source: fine-focus sealed tube	1322 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 24.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→9
Tmin = 0.579, Tmax = 0.800	k = −9→9
2862 measured reflections	l = −9→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: difmap and geom
wR(F^2) = 0.088	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0492P)^2] where P = (Fo^2 + 2Fc^2)/3
1641 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.55 e Å^−3
0 restraints	Δρmin = −0.54 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
As1	0.23569 (6)	0.36189 (6)	0.88492 (6)	0.0429 (2)
O1	−0.0461 (5)	−0.2986 (4)	0.5143 (4)	0.0600 (9)
O2	0.3923 (4)	0.2978 (4)	0.8343 (4)	0.0566 (9)
O3	0.2054 (5)	0.5123 (4)	0.7801 (4)	0.0587 (9)
H3	0.1471	0.4397	0.6629	0.088*
O4	0.2825 (4)	0.4761 (4)	1.0795 (4)	0.0481 (8)
H4	0.3751	0.5699	1.1097	0.072*
N1	0.1084 (5)	−0.0319 (4)	0.6902 (4)	0.0425 (9)
H1	0.2159	0.0665	0.7211	0.064*
C1	0.0941 (6)	−0.1725 (6)	0.5760 (5)	0.0421 (11)
C2	0.2690 (7)	−0.1596 (6)	0.5366 (6)	0.0517 (12)
H2B	0.3711	−0.0581	0.5865	0.062*
C3	0.2838 (8)	−0.2876 (7)	0.4332 (6)	0.0636 (15)
H3A	0.1830	−0.3899	0.3824	0.076*
H3B	0.3950	−0.2755	0.4111	0.076*
C4	−0.0273 (6)	−0.0015 (5)	0.7599 (5)	0.0384 (10)
C5	0.0138 (6)	0.1684 (5)	0.8569 (5)	0.0399 (10)
C6	−0.1141 (6)	0.2023 (6)	0.9324 (6)	0.0517 (12)
H6A	−0.0855	0.3146	0.9968	0.062*
C7	−0.2806 (6)	0.0738 (6)	0.9136 (6)	0.0539 (13)
H7A	−0.3654	0.0979	0.9642	0.065*
C8	−0.3219 (6)	−0.0937 (6)	0.8177 (6)	0.0551 (13)
H8A	−0.4355	−0.1820	0.8039	0.066*
C9	−0.1969 (6)	−0.1310 (6)	0.7429 (6)	0.0493 (12)
H9A	−0.2267	−0.2444	0.6803	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
As1	0.0354 (3)	0.0349 (3)	0.0460 (3)	0.0056 (2)	0.0113 (2)	−0.0056 (2)
O1	0.054 (2)	0.0424 (19)	0.058 (2)	−0.0001 (19)	0.0107 (18)	−0.0097 (18)
O2	0.0332 (17)	0.0496 (19)	0.066 (2)	0.0057 (16)	0.0108 (16)	−0.0174 (17)
O3	0.068 (2)	0.0400 (18)	0.050 (2)	0.0062 (18)	0.0118 (18)	0.0010 (17)
O4	0.0334 (16)	0.0419 (17)	0.049 (2)	0.0032 (15)	0.0047 (14)	−0.0125 (15)
N1	0.034 (2)	0.0306 (19)	0.048 (2)	0.0030 (17)	0.0055 (18)	−0.0064 (18)
C1	0.050 (3)	0.033 (2)	0.035 (3)	0.011 (2)	0.006 (2)	0.002 (2)
C2	0.053 (3)	0.044 (3)	0.050 (3)	0.015 (3)	0.015 (3)	0.000 (2)
C3	0.067 (4)	0.060 (3)	0.064 (4)	0.027 (3)	0.023 (3)	0.003 (3)
C4	0.035 (2)	0.034 (2)	0.039 (3)	0.008 (2)	0.005 (2)	0.005 (2)
C5	0.034 (2)	0.036 (2)	0.043 (3)	0.007 (2)	0.009 (2)	0.005 (2)
C6	0.046 (3)	0.047 (3)	0.060 (3)	0.017 (3)	0.018 (3)	0.007 (3)
C7	0.038 (3)	0.058 (3)	0.066 (4)	0.016 (3)	0.020 (3)	0.016 (3)
C8	0.034 (3)	0.052 (3)	0.072 (4)	0.006 (2)	0.013 (3)	0.020 (3)
C9	0.047 (3)	0.035 (2)	0.054 (3)	0.007 (2)	0.010 (2)	0.001 (2)

Geometric parameters (Å, º)

As1—O2	1.643 (3)	C3—H3A	0.9300
As1—O4	1.687 (3)	C3—H3B	0.9300
As1—O3	1.720 (3)	C4—C9	1.385 (6)
As1—C5	1.892 (4)	C4—C5	1.410 (6)
O1—C1	1.215 (5)	C5—C6	1.391 (6)
O3—H3	1.0267	C6—C7	1.361 (6)
O4—H4	0.8373	C6—H6A	0.9300
N1—C1	1.350 (5)	C7—C8	1.389 (6)
N1—C4	1.412 (5)	C7—H7A	0.9300
N1—H1	0.9258	C8—C9	1.379 (6)
C1—C2	1.488 (6)	C8—H8A	0.9300
C2—C3	1.319 (6)	C9—H9A	0.9300
C2—H2B	0.9300
O2—As1—O4	114.58 (15)	H3A—C3—H3B	120.0
O2—As1—O3	112.57 (17)	C9—C4—C5	118.1 (4)
O4—As1—O3	101.50 (15)	C9—C4—N1	123.7 (4)
O2—As1—C5	112.33 (17)	C5—C4—N1	118.2 (4)
O4—As1—C5	105.84 (16)	C6—C5—C4	120.1 (4)
O3—As1—C5	109.27 (17)	C6—C5—As1	116.7 (3)
As1—O3—H3	104.6	C4—C5—As1	123.2 (3)
As1—O4—H4	117.5	C7—C6—C5	121.1 (4)
C1—N1—C4	128.6 (4)	C7—C6—H6A	119.4
C1—N1—H1	118.9	C5—C6—H6A	119.4
C4—N1—H1	112.0	C6—C7—C8	119.0 (4)
O1—C1—N1	123.6 (4)	C6—C7—H7A	120.5
O1—C1—C2	123.3 (4)	C8—C7—H7A	120.5
N1—C1—C2	113.0 (4)	C9—C8—C7	120.9 (4)
C3—C2—C1	122.1 (5)	C9—C8—H8A	119.5
C3—C2—H2B	119.0	C7—C8—H8A	119.5
C1—C2—H2B	119.0	C8—C9—C4	120.8 (4)
C2—C3—H3A	120.0	C8—C9—H9A	119.6
C2—C3—H3B	120.0	C4—C9—H9A	119.6
C4—N1—C1—O1	0.3 (7)	O3—As1—C5—C6	−69.7 (4)
C4—N1—C1—C2	−178.2 (4)	O2—As1—C5—C4	−17.8 (4)
O1—C1—C2—C3	−1.4 (8)	O4—As1—C5—C4	−143.6 (4)
N1—C1—C2—C3	177.0 (4)	O3—As1—C5—C4	107.8 (4)
C1—N1—C4—C9	12.8 (7)	C4—C5—C6—C7	−0.5 (7)
C1—N1—C4—C5	−169.4 (4)	As1—C5—C6—C7	177.1 (4)
C9—C4—C5—C6	0.1 (6)	C5—C6—C7—C8	0.3 (8)
N1—C4—C5—C6	−177.8 (4)	C6—C7—C8—C9	0.3 (8)
C9—C4—C5—As1	−177.4 (3)	C7—C8—C9—C4	−0.8 (7)
N1—C4—C5—As1	4.8 (6)	C5—C4—C9—C8	0.5 (7)
O2—As1—C5—C6	164.7 (3)	N1—C4—C9—C8	178.3 (4)
O4—As1—C5—C6	38.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.93	1.93	2.814 (4)	160
O3—H3···O1^i	1.03	1.65	2.669 (5)	172
O4—H4···O2^ii	0.84	1.77	2.561 (4)	157

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