Guanidinium 2-amino-4-nitro­benzoate monohydrate at 130 K

Guanidinium 4-nitro­anthranilate monohydrate, CH₆N₃⁺·C₇H₅N₂O₄^-·H₂O, determined at 130 K, forms a primary hydrogen-bonded ribbon structure through cyclic hydrogen-bonding inter­actions involving all six protons of the guanidinium cation with the amino N-atom and carboxyl­ate O-atom acceptors of the anion, and the water mol­ecule of solvation. Other inter­actions, including the water mol­ecule bridging the primary ribbons, give a three-dimensional structure.

Key indicators

• Single-crystal X-ray study
• T = 130 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.108
• Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.68

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

   1 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
   1 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: SMART (Bruker, 2000); cell refinement: SMART; 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: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

guanidinium 2-amino-4-nitrobenzoate monohydrate

Crystal data

CH6N3^+·C7H5N2O4^−·H2O	F(000) = 544
Mr = 259.23	Dx = 1.525 Mg m^−3
Monoclinic, P21/n	Melting point = 524–525 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 16.122 (5) Å	Cell parameters from 2122 reflections
b = 3.7796 (11) Å	θ = 2.7–27.8°
c = 19.715 (5) Å	µ = 0.13 mm^−1
β = 110.006 (5)°	T = 130 K
V = 1128.8 (6) Å^3	Plate, yellow
Z = 4	0.45 × 0.40 × 0.10 mm

Data collection

Bruker CCD area-detector diffractometer	1966 independent reflections
Radiation source: sealed tube	1677 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −19→17
Tmin = 0.92, Tmax = 0.98	k = −4→4
5221 measured reflections	l = −23→22

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.066P)^2] where P = (Fo^2 + 2Fc^2)/3
1966 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O41	0.36608 (8)	0.4094 (3)	0.47301 (6)	0.0412 (4)
O42	0.27127 (8)	0.6702 (4)	0.38458 (7)	0.0472 (5)
O71	0.50181 (7)	0.2266 (3)	0.16451 (6)	0.0294 (4)
O72	0.61594 (7)	0.0487 (3)	0.25716 (6)	0.0289 (4)
N2	0.60292 (9)	0.0208 (3)	0.38653 (8)	0.0256 (4)
N4	0.33826 (9)	0.5017 (3)	0.41022 (7)	0.0285 (4)
C1	0.48933 (9)	0.2550 (3)	0.27992 (8)	0.0206 (5)
C2	0.52125 (9)	0.1695 (4)	0.35351 (8)	0.0204 (4)
C3	0.47011 (10)	0.2523 (4)	0.39568 (8)	0.0221 (4)
C4	0.38975 (10)	0.4128 (4)	0.36407 (8)	0.0223 (5)
C5	0.35669 (10)	0.4984 (4)	0.29270 (8)	0.0227 (5)
C6	0.40726 (10)	0.4151 (4)	0.25135 (8)	0.0223 (4)
C7	0.53946 (10)	0.1708 (4)	0.23010 (8)	0.0228 (5)
N11	0.78397 (10)	0.4026 (4)	0.33388 (8)	0.0282 (5)
N21	0.76734 (10)	0.4825 (4)	0.44316 (9)	0.0285 (5)
N31	0.89382 (9)	0.6570 (4)	0.42606 (9)	0.0288 (4)
C11	0.81492 (10)	0.5117 (4)	0.40054 (8)	0.0230 (5)
O1W	0.90079 (9)	0.7701 (4)	0.57151 (7)	0.0369 (4)
H3	0.49060	0.19820	0.44580	0.0270*
H5	0.30100	0.61100	0.27240	0.0270*
H6	0.38520	0.46920	0.20130	0.0270*
H2A	0.6092 (12)	−0.087 (5)	0.4263 (10)	0.032 (5)*
H2B	0.6236 (13)	−0.076 (5)	0.3542 (11)	0.047 (6)*
H11	0.7312 (13)	0.315 (4)	0.3139 (10)	0.033 (5)*
H12	0.8126 (14)	0.429 (5)	0.3059 (11)	0.042 (5)*
H21	0.7179 (14)	0.360 (5)	0.4284 (11)	0.048 (6)*
H22	0.7934 (11)	0.543 (4)	0.4844 (10)	0.025 (5)*
H31	0.9161 (12)	0.716 (5)	0.4697 (12)	0.045 (6)*
H32	0.9241 (12)	0.694 (4)	0.3997 (11)	0.038 (5)*
H11W	0.9251 (15)	0.964 (7)	0.5948 (13)	0.067 (8)*
H12W	0.9331 (17)	0.608 (7)	0.6043 (14)	0.085 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O41	0.0426 (8)	0.0611 (8)	0.0250 (7)	0.0035 (6)	0.0183 (6)	0.0031 (6)
O42	0.0386 (7)	0.0684 (9)	0.0420 (8)	0.0211 (7)	0.0232 (7)	0.0073 (7)
O71	0.0296 (6)	0.0377 (7)	0.0226 (7)	0.0052 (5)	0.0112 (5)	0.0013 (5)
O72	0.0233 (6)	0.0375 (6)	0.0269 (7)	0.0046 (5)	0.0099 (5)	−0.0011 (5)
N2	0.0249 (7)	0.0287 (7)	0.0226 (8)	0.0030 (5)	0.0073 (7)	0.0057 (6)
N4	0.0294 (8)	0.0325 (7)	0.0273 (8)	−0.0024 (6)	0.0143 (7)	−0.0010 (6)
C1	0.0208 (8)	0.0182 (7)	0.0226 (9)	−0.0039 (6)	0.0071 (7)	−0.0014 (6)
C2	0.0200 (7)	0.0167 (7)	0.0235 (8)	−0.0040 (6)	0.0060 (7)	−0.0004 (6)
C3	0.0250 (8)	0.0216 (7)	0.0191 (8)	−0.0054 (6)	0.0068 (7)	0.0002 (6)
C4	0.0247 (8)	0.0207 (7)	0.0249 (9)	−0.0045 (6)	0.0128 (7)	−0.0027 (6)
C5	0.0202 (8)	0.0211 (8)	0.0263 (9)	−0.0005 (6)	0.0075 (7)	−0.0003 (6)
C6	0.0248 (8)	0.0198 (7)	0.0222 (8)	−0.0034 (6)	0.0079 (7)	0.0006 (6)
C7	0.0241 (8)	0.0210 (7)	0.0231 (9)	−0.0018 (6)	0.0077 (7)	−0.0002 (6)
N11	0.0240 (8)	0.0373 (8)	0.0246 (8)	−0.0050 (6)	0.0099 (7)	0.0000 (6)
N21	0.0254 (8)	0.0360 (8)	0.0258 (9)	−0.0037 (6)	0.0108 (7)	−0.0036 (6)
N31	0.0244 (7)	0.0400 (8)	0.0237 (8)	−0.0057 (6)	0.0105 (7)	−0.0026 (7)
C11	0.0242 (8)	0.0214 (7)	0.0240 (9)	0.0025 (6)	0.0091 (7)	0.0031 (6)
O1W	0.0444 (8)	0.0366 (7)	0.0270 (7)	−0.0015 (6)	0.0089 (6)	−0.0049 (6)

Geometric parameters (Å, º)

O41—N4	1.2147 (17)	N21—H22	0.810 (18)
O42—N4	1.206 (2)	N21—H21	0.88 (2)
O71—C7	1.2442 (19)	N31—H31	0.84 (2)
O72—C7	1.252 (2)	N31—H32	0.84 (2)
O1W—H11W	0.88 (3)	C1—C7	1.504 (2)
O1W—H12W	0.91 (3)	C1—C6	1.387 (2)
N2—C2	1.374 (2)	C1—C2	1.401 (2)
N4—C4	1.465 (2)	C2—C3	1.392 (2)
N2—H2B	0.89 (2)	C3—C4	1.372 (2)
N2—H2A	0.858 (19)	C4—C5	1.362 (2)
N11—C11	1.303 (2)	C5—C6	1.372 (2)
N21—C11	1.322 (2)	C3—H3	0.9500
N31—C11	1.317 (2)	C5—H5	0.9500
N11—H12	0.84 (2)	C6—H6	0.9500
N11—H11	0.87 (2)
H11W—O1W—H12W	98 (2)	N2—C2—C3	118.46 (14)
O41—N4—O42	122.98 (15)	N2—C2—C1	122.55 (14)
O42—N4—C4	118.51 (13)	C2—C3—C4	119.23 (14)
O41—N4—C4	118.48 (14)	N4—C4—C5	118.84 (14)
C2—N2—H2A	114.9 (14)	N4—C4—C3	117.83 (13)
C2—N2—H2B	111.2 (14)	C3—C4—C5	123.31 (15)
H2A—N2—H2B	120.1 (18)	C4—C5—C6	117.20 (15)
C11—N11—H12	121.3 (15)	C1—C6—C5	122.47 (14)
H11—N11—H12	114.9 (19)	O72—C7—C1	118.07 (13)
C11—N11—H11	123.6 (13)	O71—C7—O72	124.37 (15)
C11—N21—H21	119.4 (14)	O71—C7—C1	117.57 (14)
C11—N21—H22	113.6 (13)	C2—C3—H3	120.00
H21—N21—H22	125.5 (19)	C4—C3—H3	120.00
H31—N31—H32	117 (2)	C6—C5—H5	121.00
C11—N31—H32	121.6 (14)	C4—C5—H5	121.00
C11—N31—H31	121.3 (14)	C5—C6—H6	119.00
C6—C1—C7	118.56 (13)	C1—C6—H6	119.00
C2—C1—C6	118.85 (14)	N11—C11—N21	120.63 (16)
C2—C1—C7	122.57 (13)	N11—C11—N31	120.25 (16)
C1—C2—C3	118.93 (14)	N21—C11—N31	119.12 (15)
O42—N4—C4—C3	173.60 (15)	C2—C1—C7—O72	−6.6 (2)
O41—N4—C4—C5	176.48 (14)	C6—C1—C2—N2	−177.93 (14)
O42—N4—C4—C5	−5.2 (2)	C6—C1—C2—C3	−0.9 (2)
O41—N4—C4—C3	−4.7 (2)	C1—C2—C3—C4	0.4 (2)
C7—C1—C2—C3	−179.10 (13)	N2—C2—C3—C4	177.64 (14)
C7—C1—C6—C5	179.42 (14)	C2—C3—C4—N4	−179.00 (13)
C2—C1—C7—O71	173.25 (14)	C2—C3—C4—C5	−0.3 (2)
C2—C1—C6—C5	1.1 (2)	N4—C4—C5—C6	179.19 (13)
C6—C1—C7—O71	−5.0 (2)	C3—C4—C5—C6	0.5 (2)
C6—C1—C7—O72	175.20 (14)	C4—C5—C6—C1	−0.9 (2)
C7—C1—C2—N2	3.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O71^i	0.88 (3)	1.90 (3)	2.755 (2)	162 (2)
O1W—H12W···O71^ii	0.91 (3)	1.83 (3)	2.738 (2)	175 (2)
N2—H2A···O41^iii	0.858 (19)	2.246 (19)	3.101 (2)	174.2 (17)
N2—H2B···O72	0.89 (2)	1.93 (2)	2.632 (2)	133.9 (17)
N11—H11···O72	0.87 (2)	2.07 (2)	2.935 (2)	170.1 (18)
N11—H12···O72^iv	0.84 (2)	2.01 (2)	2.848 (2)	173.5 (18)
N21—H21···N2	0.88 (2)	2.17 (2)	3.049 (2)	174 (2)
N21—H22···O1W	0.810 (18)	2.156 (18)	2.914 (2)	155.7 (18)
N31—H31···O1W	0.84 (2)	2.11 (2)	2.863 (2)	148.1 (19)
N31—H32···O71^iv	0.84 (2)	2.02 (2)	2.854 (2)	173.9 (15)
C6—H6···O71	0.95	2.42	2.747 (2)	100

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