Redetermination of phenyl­biguanide hydro­chloride

The crystal structure of the title compound, N-phenyl­imidocarbonimidic di­amide hydro­chloride (phenyl­biguanide hydro­chloride), C₈H₁₂N₅⁺·Cl^-, (BIGH)⁺·Cl^-, has been redetermined with higher precision and with the location and free refinement of all H atoms.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.063
• wR factor = 0.192
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level A
REFLT03_ALERT_3_A  Reflection count < 85% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           35.00
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               2672
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         4557
           Completeness (_total/calc)             58.64%
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.58

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

   2 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XCS (Colapietro et al., 1992); cell refinement: XCS; data reduction: XCS; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

N-phenylimidocarbonimidic diamide hydrochloride

Crystal data

C8H12N5^+·Cl^−	F(000) = 448
Mr = 213.68	Dx = 1.374 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
a = 9.3421 (14) Å	Cell parameters from 30 reflections
b = 6.6804 (11) Å	θ = 10.0–21.0°
c = 17.297 (6) Å	µ = 0.34 mm^−1
β = 106.82 (2)°	T = 298 K
V = 1033.3 (4) Å^3	Tablets, colourless
Z = 4	0.30 × 0.30 × 0.10 mm

Data collection

Huber CS four-circle diffractometer	Rint = 0.043
Radiation source: x-RAY tube	θmax = 35.0°, θmin = 2.3°
Graphite monochromator	h = 0→14
ω scan	k = 0→10
5323 measured reflections	l = −26→25
2672 independent reflections	3 standard reflections every 97 reflections
2659 reflections with I > 2σ(I)	intensity decay: <3%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.063	Only H-atom coordinates refined
wR(F^2) = 0.192	w = 1/[σ^2(Fo^2) + (0.122P)^2 + 0.6386P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max = 0.001
2672 reflections	Δρmax = 0.36 e Å^−3
163 parameters	Δρmin = −0.38 e Å^−3
0 restraints

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
Cl1	0.26817 (7)	0.48856 (10)	0.77031 (4)	0.03783 (18)
N1	0.6007 (2)	0.3423 (4)	0.89499 (13)	0.0354 (4)
N2	0.8380 (2)	0.4522 (4)	0.90092 (13)	0.0352 (4)
N3	0.6259 (3)	0.5585 (4)	0.79669 (15)	0.0421 (5)
N4	1.0699 (3)	0.5653 (4)	0.90350 (16)	0.0434 (5)
N5	0.9246 (3)	0.4277 (4)	0.78597 (14)	0.0414 (5)
C1	0.6539 (3)	0.2033 (4)	0.95920 (13)	0.0317 (4)
C2	0.7536 (3)	0.0529 (4)	0.95403 (18)	0.0413 (5)
C3	0.8052 (4)	−0.0805 (5)	1.0180 (2)	0.0524 (7)
C4	0.7549 (4)	−0.0648 (5)	1.08568 (19)	0.0505 (7)
C5	0.6536 (4)	0.0830 (5)	1.09018 (16)	0.0440 (6)
C6	0.6029 (3)	0.2177 (4)	1.02676 (15)	0.0362 (5)
C7	0.6917 (3)	0.4513 (4)	0.86267 (14)	0.0306 (4)
C8	0.9406 (3)	0.4830 (4)	0.86207 (14)	0.0312 (4)
H2	0.784 (4)	0.030 (5)	0.907 (2)	0.041*
H3	0.885 (4)	−0.175 (6)	1.015 (2)	0.052*
H4	0.797 (4)	−0.146 (6)	1.129 (2)	0.051*
H5	0.612 (4)	0.102 (6)	1.137 (2)	0.044*
H6	0.529 (4)	0.341 (5)	1.0297 (19)	0.036*
H11	0.504 (4)	0.386 (5)	0.8817 (19)	0.035*
H31	0.533 (4)	0.555 (6)	0.776 (2)	0.042*
H32	0.671 (4)	0.645 (6)	0.775 (2)	0.042*
H41	1.146 (4)	0.566 (6)	0.878 (2)	0.043*
H42	1.081 (4)	0.580 (6)	0.954 (2)	0.043*
H51	0.999 (4)	0.427 (6)	0.771 (2)	0.042*
H52	0.853 (4)	0.344 (6)	0.764 (2)	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0324 (3)	0.0409 (3)	0.0425 (3)	0.0028 (2)	0.0145 (2)	0.0008 (2)
N1	0.0253 (8)	0.0439 (11)	0.0377 (10)	−0.0010 (8)	0.0101 (7)	0.0077 (8)
N2	0.0280 (9)	0.0447 (11)	0.0322 (9)	−0.0063 (8)	0.0077 (7)	0.0023 (8)
N3	0.0314 (10)	0.0468 (12)	0.0468 (12)	−0.0014 (9)	0.0094 (9)	0.0166 (10)
N4	0.0321 (10)	0.0557 (14)	0.0430 (12)	−0.0131 (10)	0.0118 (9)	−0.0088 (11)
N5	0.0314 (10)	0.0595 (15)	0.0337 (10)	−0.0069 (10)	0.0099 (8)	−0.0047 (10)
C1	0.0312 (10)	0.0336 (10)	0.0300 (10)	−0.0054 (8)	0.0086 (8)	−0.0001 (8)
C2	0.0468 (14)	0.0391 (13)	0.0407 (13)	0.0042 (11)	0.0170 (11)	0.0040 (10)
C3	0.0562 (18)	0.0440 (15)	0.0568 (18)	0.0109 (14)	0.0159 (15)	0.0096 (14)
C4	0.0583 (18)	0.0481 (15)	0.0388 (14)	−0.0068 (14)	0.0039 (13)	0.0123 (12)
C5	0.0551 (16)	0.0448 (14)	0.0318 (11)	−0.0163 (12)	0.0119 (11)	−0.0010 (10)
C6	0.0385 (12)	0.0367 (12)	0.0346 (11)	−0.0085 (10)	0.0127 (9)	−0.0030 (9)
C7	0.0302 (10)	0.0318 (10)	0.0307 (10)	−0.0023 (8)	0.0103 (8)	0.0001 (8)
C8	0.0289 (9)	0.0310 (10)	0.0329 (10)	−0.0028 (8)	0.0077 (8)	0.0007 (8)

Geometric parameters (Å, º)

N1—C7	1.357 (3)	N5—H52	0.87 (4)
N1—C1	1.422 (3)	C1—C6	1.387 (3)
N1—H11	0.91 (3)	C1—C2	1.391 (4)
N2—C7	1.335 (3)	C2—C3	1.394 (4)
N2—C8	1.336 (3)	C2—H2	0.95 (4)
N3—C7	1.337 (3)	C3—C4	1.385 (5)
N3—H31	0.84 (4)	C3—H3	0.99 (4)
N3—H32	0.86 (4)	C4—C5	1.385 (5)
N4—C8	1.332 (3)	C4—H4	0.91 (4)
N4—H41	0.93 (4)	C5—C6	1.392 (4)
N4—H42	0.85 (4)	C5—H5	1.00 (3)
N5—C8	1.333 (3)	C6—H6	1.08 (3)
N5—H51	0.81 (4)
C7—N1—C1	123.6 (2)	C4—C3—C2	119.9 (3)
C7—N1—H11	115 (2)	C4—C3—H3	123 (2)
C1—N1—H11	120 (2)	C2—C3—H3	117 (2)
C7—N2—C8	122.1 (2)	C5—C4—C3	120.4 (3)
C7—N3—H31	121 (3)	C5—C4—H4	121 (2)
C7—N3—H32	124 (2)	C3—C4—H4	118 (2)
H31—N3—H32	114 (3)	C4—C5—C6	119.9 (3)
C8—N4—H41	116 (2)	C4—C5—H5	124 (2)
C8—N4—H42	115 (2)	C6—C5—H5	116 (2)
H41—N4—H42	127 (3)	C1—C6—C5	119.8 (3)
C8—N5—H51	117 (3)	C1—C6—H6	118.0 (17)
C8—N5—H52	118 (2)	C5—C6—H6	122.0 (17)
H51—N5—H52	118 (3)	N2—C7—N3	124.9 (2)
C6—C1—C2	120.3 (2)	N2—C7—N1	118.2 (2)
C6—C1—N1	119.0 (2)	N3—C7—N1	116.8 (2)
C2—C1—N1	120.7 (2)	N4—C8—N5	118.1 (2)
C1—C2—C3	119.7 (3)	N4—C8—N2	117.6 (2)
C1—C2—H2	123 (2)	N5—C8—N2	124.2 (2)
C3—C2—H2	117 (2)
C7—N1—C1—C6	128.2 (3)	N1—C1—C6—C5	180.0 (2)
C7—N1—C1—C2	−52.9 (4)	C4—C5—C6—C1	0.0 (4)
C6—C1—C2—C3	−1.7 (4)	C8—N2—C7—N3	−30.8 (4)
N1—C1—C2—C3	179.4 (3)	C8—N2—C7—N1	153.0 (2)
C1—C2—C3—C4	1.2 (5)	C1—N1—C7—N2	−10.9 (4)
C2—C3—C4—C5	−0.1 (5)	C1—N1—C7—N3	172.5 (2)
C3—C4—C5—C6	−0.5 (5)	C7—N2—C8—N4	151.8 (3)
C2—C1—C6—C5	1.1 (4)	C7—N2—C8—N5	−31.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···Cl1	0.91 (3)	2.57 (3)	3.373 (2)	148 (3)
N3—H31···Cl1	0.84 (4)	2.49 (4)	3.273 (3)	156 (3)
N3—H32···Cl1^i	0.86 (4)	2.54 (4)	3.353 (3)	157 (3)
N4—H41···Cl1^ii	0.93 (4)	2.51 (4)	3.387 (3)	157 (3)
N4—H42···N2^iii	0.85 (4)	2.41 (4)	3.243 (4)	164 (3)
N5—H51···Cl1^ii	0.81 (4)	2.55 (4)	3.324 (3)	160 (3)
N5—H52···Cl1^iv	0.87 (4)	2.62 (4)	3.432 (3)	155 (3)

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