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The crystal structure of the title compound, (C14H19N4O3)[AsO2(OH)(C6H4NO3)]·H2O, consists of substituted pyrimidine cations, roxarsone (3-nitro-4-hydr­oxyphenyl­arsonate) anions and water mol­ecules. Due to deprotonation of the arsonate group, the As—O bond distances in the anion are significantly different. An extensive network of O—H...O, N—H...O and N—H...N hydrogen bonds helps to stabilize the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032090/hb2119sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032090/hb2119Isup2.hkl
Contains datablock I

CCDC reference: 621332

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.057
  • wR factor = 0.119
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N1
Alert level C PLAT213_ALERT_2_C Atom O5A has ADP max/min Ratio ............. 3.30 prola PLAT213_ALERT_2_C Atom O5B has ADP max/min Ratio ............. 3.60 prola PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.69 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.22 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.05 Ratio PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.74 PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
C14H19N4O3·C6H5AsNO6·H2OF(000) = 2352
Mr = 571.38Dx = 1.565 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 15356 reflections
a = 8.1865 (13) Åθ = 2.2–25.2°
b = 20.9285 (16) ŵ = 1.47 mm1
c = 28.304 (2) ÅT = 294 K
V = 4849.3 (9) Å3Prism, yellow
Z = 80.34 × 0.30 × 0.25 mm
Data collection top
Bruker APEX II
diffractometer
4489 independent reflections
Radiation source: fine-focus sealed tube3922 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
φ and ω scanθmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan
SADABS (Sheldrick, 2002)
h = 99
Tmin = 0.622, Tmax = 0.700k = 2523
24891 measured reflectionsl = 2934
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: difmap and geom
wR(F2) = 0.119H-atom parameters constrained
S = 1.21 w = 1/[σ2(Fo2) + (0.0447P)2 + 5.6729P]
where P = (Fo2 + 2Fc2)/3
4489 reflections(Δ/σ)max = 0.001
347 parametersΔρmax = 0.64 e Å3
0 restraintsΔρmin = 0.51 e Å3
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
xyzUiso*/UeqOcc. (<1)
As0.13857 (4)0.079784 (17)0.018532 (13)0.02743 (14)
N10.4029 (5)0.2364 (2)0.14004 (14)0.0512 (10)
N20.1960 (4)0.26052 (16)0.00154 (12)0.0382 (8)
H2A0.14430.21990.00120.057*
H2B0.30150.26340.01310.057*
N30.1562 (4)0.32426 (18)0.11841 (12)0.0469 (9)
H3A0.18290.35650.13930.070*
H3B0.22240.28980.11160.070*
N40.0147 (4)0.29321 (15)0.05902 (11)0.0333 (7)
N50.2462 (4)0.35461 (16)0.04058 (10)0.0333 (7)
H5A0.34210.36270.02350.050*
O10.2200 (3)0.03098 (14)0.02431 (9)0.0443 (7)
H10.12940.01240.03890.067*
O20.0245 (3)0.03543 (14)0.05449 (9)0.0429 (7)
O30.0383 (4)0.14112 (13)0.00401 (12)0.0490 (8)
O40.7178 (3)0.18306 (14)0.12672 (10)0.0451 (7)
H4A0.81020.15860.12390.068*
O5A0.5041 (10)0.2753 (5)0.1478 (6)0.085 (5)0.60 (3)
O6A0.2608 (14)0.2436 (9)0.1536 (7)0.111 (6)0.60 (3)
O5B0.482 (3)0.2350 (17)0.1785 (8)0.136 (14)0.40 (3)
O6B0.303 (3)0.2719 (9)0.1348 (6)0.087 (8)0.40 (3)
O70.2024 (4)0.35980 (14)0.27862 (9)0.0455 (7)
O80.1198 (3)0.46733 (15)0.32319 (9)0.0439 (7)
O90.0217 (5)0.56423 (16)0.27743 (11)0.0625 (10)
O1W0.9565 (4)0.10540 (14)0.13160 (10)0.0456 (7)
H1A0.98860.08200.10840.068*
H1B0.94620.07870.15590.068*
C10.3258 (4)0.11069 (17)0.05114 (12)0.0261 (8)
C20.4810 (5)0.08592 (17)0.04496 (13)0.0313 (8)
H20.49690.05290.02340.038*
C30.6119 (4)0.10895 (18)0.06988 (13)0.0322 (8)
H30.71480.09120.06520.039*
C40.5925 (5)0.15888 (18)0.10219 (13)0.0308 (8)
C50.4358 (5)0.18346 (18)0.10778 (13)0.0321 (9)
C60.3028 (5)0.15973 (17)0.08284 (13)0.0305 (8)
H60.19920.17680.08750.037*
C70.0271 (5)0.33696 (19)0.09109 (13)0.0319 (9)
C80.1517 (5)0.30230 (18)0.03420 (13)0.0311 (8)
C90.1967 (5)0.40142 (19)0.07022 (13)0.0340 (9)
H90.25960.43830.07270.041*
C100.0590 (5)0.39663 (18)0.09637 (12)0.0309 (8)
C110.0010 (5)0.4511 (2)0.12613 (13)0.0397 (10)
H11A0.11870.45330.12240.048*
H11B0.04370.49010.11290.048*
C120.0349 (5)0.45144 (19)0.17873 (13)0.0338 (9)
C130.1072 (5)0.40140 (19)0.20259 (13)0.0343 (9)
H130.13790.36460.18640.041*
C140.1340 (5)0.40630 (19)0.25116 (14)0.0346 (9)
C150.0890 (5)0.4613 (2)0.27529 (13)0.0376 (10)
C160.0172 (5)0.5112 (2)0.25090 (15)0.0424 (10)
C170.0093 (5)0.5067 (2)0.20278 (14)0.0424 (10)
H170.05680.54060.18650.051*
C180.2569 (7)0.3034 (2)0.25595 (17)0.0565 (13)
H18A0.16590.28250.24110.085*
H18B0.30460.27520.27890.085*
H18C0.33700.31410.23250.085*
C190.0036 (6)0.4390 (2)0.35189 (15)0.0511 (12)
H19A0.10540.46070.34690.077*
H19B0.02690.44230.38450.077*
H19C0.01550.39470.34360.077*
C200.1030 (8)0.6156 (3)0.2553 (2)0.083 (2)
H20A0.03180.63490.23240.125*
H20B0.13290.64680.27860.125*
H20C0.19950.60010.23980.125*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
As0.0261 (2)0.0261 (2)0.0302 (2)0.00157 (15)0.00576 (15)0.00428 (15)
N10.043 (2)0.058 (3)0.053 (2)0.002 (2)0.005 (2)0.026 (2)
N20.041 (2)0.0344 (19)0.0390 (18)0.0015 (15)0.0078 (16)0.0037 (15)
N30.040 (2)0.054 (2)0.046 (2)0.0143 (17)0.0170 (17)0.0082 (17)
N40.0329 (18)0.0365 (19)0.0305 (16)0.0079 (14)0.0025 (14)0.0032 (14)
N50.0303 (17)0.0407 (19)0.0289 (16)0.0080 (14)0.0045 (14)0.0005 (14)
O10.0344 (16)0.0520 (19)0.0466 (17)0.0054 (14)0.0016 (13)0.0209 (14)
O20.0449 (17)0.0512 (18)0.0326 (15)0.0194 (14)0.0025 (13)0.0057 (13)
O30.0412 (18)0.0306 (16)0.075 (2)0.0001 (13)0.0259 (16)0.0010 (14)
O40.0319 (16)0.0437 (18)0.0597 (19)0.0025 (13)0.0146 (14)0.0154 (14)
O5A0.053 (5)0.057 (6)0.144 (11)0.016 (4)0.002 (5)0.066 (6)
O6A0.057 (5)0.141 (12)0.135 (12)0.011 (6)0.030 (6)0.104 (9)
O5B0.132 (14)0.18 (3)0.102 (14)0.098 (16)0.080 (12)0.106 (16)
O6B0.113 (17)0.076 (11)0.071 (9)0.070 (11)0.042 (9)0.038 (7)
O70.0568 (19)0.0482 (18)0.0316 (15)0.0068 (15)0.0002 (14)0.0030 (13)
O80.0415 (17)0.064 (2)0.0260 (14)0.0082 (14)0.0003 (12)0.0104 (13)
O90.089 (3)0.054 (2)0.0450 (18)0.0212 (18)0.0100 (18)0.0207 (16)
O1W0.0525 (19)0.0505 (18)0.0337 (15)0.0112 (15)0.0013 (14)0.0033 (13)
C10.0231 (19)0.0286 (19)0.0267 (18)0.0069 (15)0.0086 (14)0.0021 (15)
C20.039 (2)0.0244 (19)0.031 (2)0.0002 (16)0.0058 (16)0.0067 (15)
C30.026 (2)0.033 (2)0.038 (2)0.0022 (16)0.0037 (16)0.0035 (17)
C40.030 (2)0.030 (2)0.033 (2)0.0053 (16)0.0054 (16)0.0018 (16)
C50.037 (2)0.029 (2)0.030 (2)0.0003 (17)0.0017 (17)0.0061 (16)
C60.0266 (19)0.033 (2)0.032 (2)0.0005 (16)0.0016 (16)0.0022 (16)
C70.029 (2)0.040 (2)0.0271 (19)0.0014 (17)0.0017 (16)0.0029 (17)
C80.033 (2)0.033 (2)0.0272 (19)0.0010 (16)0.0016 (16)0.0055 (16)
C90.041 (2)0.034 (2)0.0272 (19)0.0109 (18)0.0037 (17)0.0011 (16)
C100.039 (2)0.032 (2)0.0214 (18)0.0013 (17)0.0052 (16)0.0018 (15)
C110.052 (3)0.040 (2)0.028 (2)0.001 (2)0.0000 (19)0.0025 (17)
C120.036 (2)0.036 (2)0.029 (2)0.0048 (17)0.0026 (17)0.0021 (17)
C130.037 (2)0.036 (2)0.030 (2)0.0054 (17)0.0083 (17)0.0068 (16)
C140.033 (2)0.039 (2)0.032 (2)0.0039 (17)0.0027 (17)0.0017 (17)
C150.033 (2)0.050 (3)0.029 (2)0.0076 (19)0.0031 (17)0.0058 (18)
C160.045 (3)0.045 (3)0.037 (2)0.000 (2)0.0007 (19)0.014 (2)
C170.048 (3)0.039 (2)0.040 (2)0.006 (2)0.002 (2)0.0023 (19)
C180.069 (3)0.053 (3)0.047 (3)0.017 (3)0.005 (2)0.002 (2)
C190.055 (3)0.063 (3)0.035 (2)0.008 (2)0.006 (2)0.005 (2)
C200.109 (5)0.063 (4)0.077 (4)0.034 (4)0.022 (4)0.028 (3)
Geometric parameters (Å, º) top
As—O11.720 (3)C1—C21.383 (5)
As—O21.664 (3)C2—C31.371 (5)
As—O31.652 (3)C2—H20.9300
As—C11.903 (3)C3—C41.398 (5)
N1—O6B1.113 (14)C3—H30.9300
N1—O5A1.181 (7)C4—C51.391 (5)
N1—O6A1.234 (11)C5—C61.389 (5)
N1—O5B1.268 (14)C6—H60.9300
N1—C51.461 (5)C7—C101.442 (5)
N2—C81.323 (5)C9—C101.352 (5)
N2—H2A0.9505C9—H90.9300
N2—H2B0.9591C10—C111.500 (5)
N3—C71.336 (5)C11—C121.518 (5)
N3—H3A0.9238C11—H11A0.9700
N3—H3B0.9225C11—H11B0.9700
N4—C71.334 (5)C12—C131.380 (6)
N4—C81.337 (5)C12—C171.390 (5)
N5—C91.352 (5)C13—C141.396 (5)
N5—C81.353 (5)C13—H130.9300
N5—H5A0.9369C14—C151.389 (6)
O1—H10.9332C15—C161.382 (6)
O4—C41.339 (4)C16—C171.382 (6)
O4—H4A0.9169C17—H170.9300
O7—C141.365 (5)C18—H18A0.9600
O7—C181.416 (5)C18—H18B0.9600
O8—C151.385 (5)C18—H18C0.9600
O8—C191.426 (5)C19—H19A0.9600
O9—C161.377 (5)C19—H19B0.9600
O9—C201.411 (6)C19—H19C0.9600
O1W—H1A0.8608C20—H20A0.9600
O1W—H1B0.8887C20—H20B0.9600
C1—C61.376 (5)C20—H20C0.9600
O1—As—C1103.38 (14)N2—C8—N5118.1 (3)
O1—As—O2108.51 (14)N4—C8—N5121.7 (3)
O1—As—O3112.45 (15)N5—C9—C10122.4 (4)
O2—As—O3113.01 (16)N5—C9—H9118.8
O2—As—C1110.18 (14)C10—C9—H9118.8
O3—As—C1108.88 (15)C9—C10—C7114.5 (3)
O5A—N1—O6A121.3 (8)C9—C10—C11121.6 (4)
O6B—N1—O5B120.3 (10)C7—C10—C11123.8 (4)
O6B—N1—C5123.9 (9)C10—C11—C12119.4 (3)
O5A—N1—C5120.6 (5)C10—C11—H11A107.5
O6A—N1—C5117.3 (6)C12—C11—H11A107.5
O5B—N1—C5115.1 (9)C10—C11—H11B107.5
C8—N2—H2A118.4C12—C11—H11B107.5
C8—N2—H2B120.5H11A—C11—H11B107.0
H2A—N2—H2B116.9C13—C12—C17120.2 (4)
C7—N3—H3A114.4C13—C12—C11124.0 (4)
C7—N3—H3B120.0C17—C12—C11115.7 (4)
H3A—N3—H3B124.4C12—C13—C14119.6 (4)
C7—N4—C8118.4 (3)C12—C13—H13120.2
C9—N5—C8119.8 (3)C14—C13—H13120.2
C9—N5—H5A116.1O7—C14—C15114.8 (3)
C8—N5—H5A123.9O7—C14—C13124.9 (4)
As—O1—H1104.5C15—C14—C13120.2 (4)
C4—O4—H4A112.1C16—C15—O8119.9 (4)
C14—O7—C18117.7 (3)C16—C15—C14119.5 (4)
C15—O8—C19113.0 (3)O8—C15—C14120.6 (4)
C16—O9—C20118.8 (4)O9—C16—C17123.8 (4)
H1A—O1W—H1B105.3O9—C16—C15115.7 (4)
C6—C1—C2119.2 (3)C17—C16—C15120.5 (4)
C6—C1—As117.3 (3)C16—C17—C12119.9 (4)
C2—C1—As123.5 (3)C16—C17—H17120.1
C3—C2—C1121.4 (3)C12—C17—H17120.1
C3—C2—H2119.3O7—C18—H18A109.5
C1—C2—H2119.3O7—C18—H18B109.5
C2—C3—C4120.7 (3)H18A—C18—H18B109.5
C2—C3—H3119.7O7—C18—H18C109.5
C4—C3—H3119.7H18A—C18—H18C109.5
O4—C4—C5120.6 (3)H18B—C18—H18C109.5
O4—C4—C3122.3 (3)O8—C19—H19A109.5
C5—C4—C3117.1 (3)O8—C19—H19B109.5
C6—C5—C4122.2 (3)H19A—C19—H19B109.5
C6—C5—N1116.4 (4)O8—C19—H19C109.5
C4—C5—N1121.4 (3)H19A—C19—H19C109.5
C1—C6—C5119.4 (3)H19B—C19—H19C109.5
C1—C6—H6120.3O9—C20—H20A109.5
C5—C6—H6120.3O9—C20—H20B109.5
N4—C7—N3117.4 (4)H20A—C20—H20B109.5
N4—C7—C10122.7 (3)O9—C20—H20C109.5
N3—C7—C10119.9 (4)H20A—C20—H20C109.5
N2—C8—N4120.2 (4)H20B—C20—H20C109.5
O3—As—C1—C649.6 (3)C8—N5—C9—C104.0 (5)
O2—As—C1—C674.8 (3)N5—C9—C10—C71.8 (5)
O1—As—C1—C6169.4 (3)N5—C9—C10—C11175.1 (3)
O3—As—C1—C2131.2 (3)N4—C7—C10—C97.5 (5)
O2—As—C1—C2104.3 (3)N3—C7—C10—C9173.7 (4)
O1—As—C1—C211.5 (3)N4—C7—C10—C11169.3 (3)
C6—C1—C2—C30.3 (6)N3—C7—C10—C119.4 (6)
As—C1—C2—C3178.8 (3)C9—C10—C11—C1299.1 (5)
C1—C2—C3—C40.6 (6)C7—C10—C11—C1284.3 (5)
C2—C3—C4—O4179.2 (4)C10—C11—C12—C136.5 (6)
C2—C3—C4—C50.2 (6)C10—C11—C12—C17173.3 (4)
O4—C4—C5—C6179.8 (4)C17—C12—C13—C140.7 (6)
C3—C4—C5—C60.4 (6)C11—C12—C13—C14179.5 (4)
O4—C4—C5—N10.5 (6)C18—O7—C14—C15177.6 (4)
C3—C4—C5—N1178.9 (4)C18—O7—C14—C132.9 (6)
O6B—N1—C5—C629 (2)C12—C13—C14—O7179.1 (4)
O5A—N1—C5—C6149.4 (12)C12—C13—C14—C150.3 (6)
O6A—N1—C5—C621.1 (15)C19—O8—C15—C1697.4 (5)
O5B—N1—C5—C6142 (2)C19—O8—C15—C1484.5 (5)
O6B—N1—C5—C4151 (2)O7—C14—C15—C16179.4 (4)
O5A—N1—C5—C429.9 (13)C13—C14—C15—C160.1 (6)
O6A—N1—C5—C4159.6 (14)O7—C14—C15—O82.5 (5)
O5B—N1—C5—C439 (2)C13—C14—C15—O8178.0 (3)
C2—C1—C6—C50.3 (5)C20—O9—C16—C174.3 (7)
As—C1—C6—C5179.4 (3)C20—O9—C16—C15176.7 (5)
C4—C5—C6—C10.6 (6)O8—C15—C16—O91.1 (6)
N1—C5—C6—C1178.7 (4)C14—C15—C16—O9179.2 (4)
C8—N4—C7—N3174.2 (3)O8—C15—C16—C17177.9 (4)
C8—N4—C7—C107.0 (5)C14—C15—C16—C170.2 (6)
C7—N4—C8—N2178.9 (4)O9—C16—C17—C12179.5 (4)
C7—N4—C8—N50.7 (5)C15—C16—C17—C120.6 (7)
C9—N5—C8—N2173.5 (3)C13—C12—C17—C160.8 (6)
C9—N5—C8—N44.8 (5)C11—C12—C17—C16179.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O30.951.872.817 (4)176
N2—H2B···N4i0.962.483.318 (5)146
N3—H3A···O7ii0.922.513.223 (4)135
N3—H3B···O4iii0.922.333.139 (5)147
N3—H3B···O5Aiii0.922.483.078 (10)123
N5—H5A···O3i0.941.702.607 (5)162
O1—H1···O2iv0.931.672.582 (4)165
O4—H4A···O1W0.921.652.545 (4)165
O1W—H1A···O2v0.861.832.687 (4)171
O1W—H1B···O8vi0.892.463.221 (4)143
O1W—H1B···O9vi0.892.012.767 (4)142
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x1/2, y, z+1/2; (iii) x1, y, z; (iv) x, y, z; (v) x+1, y, z; (vi) x+1, y1/2, z+1/2.
 

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