Benzamidinium dihydrogenphosphate

Cations and anions of benzamidinium dihydrogenphosphate, C₇H₉N₂⁺·H₂PO₄, are connected by NH₂...O=P and NH₂...O(H)—P hydrogen bonds between benzamidinium NH₂ groups and dihydrogenphosphate O atoms into an infinite three-dimensional network. The anions are connected through P—OH...O=P inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.067
• wR factor = 0.172
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C7 H9 N2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: R3m/V (Siemens, 1989); cell refinement: R3m/V; data reduction: XDISK (Siemens, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1995); software used to prepare material for publication: SHELXL97.

Benzamidinium dihydrogenphosphate

Crystal data

C7H9N2^+·H2O4P^−	F(000) = 456
Mr = 218.15	Dx = 1.457 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 24 reflections
a = 12.259 (3) Å	θ = 7.2–13.8°
b = 10.067 (2) Å	µ = 0.27 mm^−1
c = 8.0578 (16) Å	T = 294 K
β = 91.28 (3)°	Broken prism, colourless
V = 994.2 (3) Å^3	0.49 × 0.30 × 0.23 mm
Z = 4

Data collection

Siemens P4 four-circle diffractometer	1071 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
Graphite monochromator	θmax = 25.0°, θmin = 2.6°
φ? ω? scans	h = −14→14
Absorption correction: ψ scan (XPREP; Sheldrick, 1995)	k = −11→0
Tmin = 0.877, Tmax = 0.939	l = 0→9
1875 measured reflections	3 standard reflections every 100 reflections
1739 independent reflections	intensity decay: 2%

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)] = 0.067	H-atom parameters constrained
wR(F^2) = 0.172	w = 1/[σ^2(Fo^2) + (0.0866P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
1739 reflections	Δρmax = 0.40 e Å^−3
128 parameters	Δρmin = −0.38 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: 0.007 (2)

Special details

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
C1	1.2329 (4)	0.2628 (4)	0.2716 (6)	0.0421 (12)
C11	1.3430 (4)	0.2501 (4)	0.2044 (6)	0.0403 (11)
N1	1.4081 (3)	0.3547 (4)	0.2014 (5)	0.0496 (11)
H11	1.4731	0.3472	0.1642	0.060*
H12	1.3856	0.4303	0.2366	0.060*
N2	1.3790 (3)	0.1354 (4)	0.1500 (5)	0.0504 (11)
H21	1.4441	0.1292	0.1132	0.060*
H22	1.3375	0.0666	0.1513	0.060*
C2	1.1760 (5)	0.1512 (5)	0.3254 (7)	0.0591 (15)
H2	1.2081	0.0676	0.3201	0.071*
C3	1.0726 (5)	0.1648 (7)	0.3864 (8)	0.0757 (19)
H3	1.0349	0.0897	0.4200	0.091*
C4	1.0240 (5)	0.2871 (7)	0.3984 (8)	0.080 (2)
H4	0.9549	0.2952	0.4426	0.096*
C5	1.0789 (5)	0.3976 (7)	0.3442 (8)	0.0721 (18)
H5	1.0461	0.4808	0.3502	0.086*
C6	1.1823 (4)	0.3862 (5)	0.2810 (6)	0.0529 (14)
H6	1.2184	0.4616	0.2444	0.063*
P1	0.67912 (10)	0.19593 (11)	0.03753 (15)	0.0356 (4)
O1	0.7181 (3)	0.1181 (3)	−0.1080 (4)	0.0425 (8)
O2	0.6146 (2)	0.1188 (3)	0.1629 (4)	0.0428 (9)
O3	0.6006 (3)	0.3125 (3)	−0.0218 (4)	0.0497 (9)
H3'	0.6095	0.3272	−0.1206	0.070*
O4	0.7804 (3)	0.2625 (3)	0.1218 (4)	0.0523 (9)
H4'	0.7623	0.2989	0.2079	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.047 (3)	0.035 (3)	0.044 (3)	−0.004 (2)	0.005 (2)	−0.011 (2)
C11	0.044 (3)	0.030 (2)	0.047 (3)	−0.002 (2)	0.003 (2)	−0.004 (2)
N1	0.049 (2)	0.026 (2)	0.075 (3)	0.0004 (17)	0.019 (2)	−0.010 (2)
N2	0.052 (2)	0.028 (2)	0.072 (3)	0.0000 (18)	0.016 (2)	−0.013 (2)
C2	0.074 (4)	0.041 (3)	0.063 (3)	−0.008 (3)	0.017 (3)	−0.006 (3)
C3	0.074 (4)	0.080 (4)	0.075 (4)	−0.034 (4)	0.028 (3)	−0.010 (4)
C4	0.051 (3)	0.107 (6)	0.082 (5)	−0.009 (4)	0.028 (3)	−0.030 (4)
C5	0.053 (3)	0.075 (4)	0.090 (5)	0.014 (3)	0.014 (3)	−0.009 (4)
C6	0.055 (3)	0.040 (3)	0.064 (4)	0.002 (2)	0.011 (3)	−0.010 (3)
P1	0.0453 (7)	0.0215 (6)	0.0404 (7)	0.0004 (5)	0.0117 (5)	0.0001 (5)
O1	0.062 (2)	0.0234 (15)	0.0423 (19)	0.0028 (14)	0.0140 (15)	−0.0046 (14)
O2	0.0549 (19)	0.0257 (16)	0.048 (2)	−0.0047 (14)	0.0152 (15)	0.0013 (14)
O3	0.067 (2)	0.0358 (18)	0.047 (2)	0.0190 (16)	0.0173 (16)	0.0110 (16)
O4	0.051 (2)	0.057 (2)	0.050 (2)	−0.0085 (17)	0.0148 (16)	−0.0111 (18)

Geometric parameters (Å, º)

C1—C6	1.391 (6)	C3—H3	0.9300
C1—C2	1.396 (7)	C4—C5	1.377 (8)
C1—C11	1.472 (7)	C4—H4	0.9300
C11—N2	1.315 (5)	C5—C6	1.381 (7)
C11—N1	1.322 (5)	C5—H5	0.9300
N1—H11	0.8600	C6—H6	0.9300
N1—H12	0.8600	P1—O1	1.498 (3)
N2—H21	0.8600	P1—O2	1.512 (3)
N2—H22	0.8600	P1—O4	1.554 (3)
C2—C3	1.377 (8)	P1—O3	1.585 (3)
C2—H2	0.9300	O3—H3'	0.8200
C3—C4	1.371 (9)	O4—H4'	0.8200
C6—C1—C2	118.4 (5)	C3—C4—C5	119.1 (5)
C6—C1—C11	120.7 (4)	C3—C4—H4	120.4
C2—C1—C11	120.9 (4)	C5—C4—H4	120.4
N2—C11—N1	119.1 (4)	C4—C5—C6	120.6 (6)
N2—C11—C1	121.1 (4)	C4—C5—H5	119.7
N1—C11—C1	119.8 (4)	C6—C5—H5	119.7
C11—N1—H11	120.0	C5—C6—C1	120.6 (5)
C11—N1—H12	120.0	C5—C6—H6	119.7
H11—N1—H12	120.0	C1—C6—H6	119.7
C11—N2—H21	120.0	O1—P1—O2	115.82 (17)
C11—N2—H22	120.0	O1—P1—O4	107.58 (18)
H21—N2—H22	120.0	O2—P1—O4	110.78 (19)
C3—C2—C1	120.1 (5)	O1—P1—O3	110.69 (18)
C3—C2—H2	120.0	O2—P1—O3	104.97 (18)
C1—C2—H2	120.0	O4—P1—O3	106.7 (2)
C4—C3—C2	121.3 (6)	P1—O3—H3'	109.5
C4—C3—H3	119.4	P1—O4—H4'	109.5
C2—C3—H3	119.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H12···O2^i	0.86	2.06	2.891 (5)	161
N1—H11···O3^ii	0.86	2.22	3.028 (5)	157
N2—H22···O1^iii	0.86	2.01	2.833 (5)	160
N2—H21···O2^ii	0.86	2.12	2.892 (5)	149
O3—H3′···O2^iv	0.82	1.83	2.643 (4)	171
O4—H4′···O1^v	0.82	1.80	2.616 (4)	178

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