2,2'-o-Phenyl­enebis(1,3-di­meth­ylguanidine)

The title compound, C₁₆H₂₈N₆, was obtained from the reaction of o-phenyl­enediamine with N,N,N',N'-tetra­methyl­form­amidinium chloride. The two guanidyl groups are almost coplanar with the benzene ring. Both C-N bonds adjacent to the benzene ring were found to be double bonds, while the others were identified as single bonds, based on their bond distances.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.047
• wR factor = 0.137
• Data-to-parameter ratio = 19.3

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

(I)

Crystal data

C16H28N6	F(000) = 664
Mr = 304.44	Dx = 1.144 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2861 reflections
a = 7.6337 (12) Å	θ = 2.5–27.2°
b = 8.5800 (13) Å	µ = 0.07 mm^−1
c = 27.199 (4) Å	T = 150 K
β = 97.000 (2)°	Prism, colorless
V = 1768.2 (5) Å^3	0.50 × 0.40 × 0.30 mm
Z = 4

Data collection

Bruker SMART 1000 CCD area detector diffractometer	3015 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
Graphite monochromator	θmax = 27.5°, θmin = 2.5°
φ and ω scans	h = −9→9
10296 measured reflections	k = −10→11
3996 independent reflections	l = −26→34

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0671P)^2 + 0.1667P] where P = (Fo^2 + 2Fc^2)/3
3996 reflections	(Δ/σ)max < 0.001
207 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Experimental. ¹H NMR (400 MHz, CDCl₃): 2.67 (s, 24H), 6.49–6.53 (m, 2H), 6.71–6.75 (m, 2H); ¹³C NMR (100 MHz, CDCl₃): 39.5 (CH₃), 120.3 (CH), 121.9 (CH), 144.0 (C), 159.1 (C=N)

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	0.23274 (16)	0.68186 (14)	0.13970 (5)	0.0246 (3)
C2	0.16967 (17)	0.77484 (14)	0.09827 (5)	0.0242 (3)
C3	0.19594 (19)	0.72384 (15)	0.05104 (5)	0.0298 (3)
C4	0.28004 (19)	0.58354 (16)	0.04379 (6)	0.0336 (3)
C5	0.33775 (18)	0.49135 (15)	0.08417 (6)	0.0329 (3)
C6	0.31210 (17)	0.53948 (15)	0.13133 (5)	0.0293 (3)
C7	0.24667 (16)	0.85403 (14)	0.20772 (5)	0.0248 (3)
C8	−0.0071 (2)	0.8366 (2)	0.25257 (6)	0.0465 (4)
C9	0.2565 (2)	0.96686 (19)	0.29065 (5)	0.0422 (4)
C10	0.52725 (18)	0.88165 (17)	0.17281 (6)	0.0353 (3)
C11	0.3720 (2)	1.11413 (16)	0.19474 (6)	0.0368 (3)
C12	−0.06544 (17)	0.94950 (14)	0.08343 (4)	0.0235 (3)
C13	0.0170 (2)	1.22317 (15)	0.08569 (6)	0.0353 (3)
C14	−0.2921 (2)	1.15529 (17)	0.08286 (6)	0.0376 (3)
C15	−0.19606 (19)	0.69007 (15)	0.09159 (6)	0.0337 (3)
C16	−0.3026 (2)	0.85247 (17)	0.02032 (6)	0.0390 (4)
N1	0.19831 (15)	0.72093 (12)	0.18765 (4)	0.0270 (3)
N2	0.15726 (15)	0.91146 (14)	0.24502 (4)	0.0316 (3)
N3	0.38589 (15)	0.94542 (12)	0.19744 (4)	0.0283 (3)
N4	0.09075 (14)	0.92062 (12)	0.10542 (4)	0.0258 (3)
N5	−0.11661 (14)	1.10351 (12)	0.07491 (4)	0.0270 (3)
N6	−0.19425 (14)	0.84153 (12)	0.06781 (4)	0.0275 (3)
H3	0.1554	0.7865	0.0232	0.036*
H4	0.2977	0.5513	0.0113	0.040*
H5	0.3950	0.3950	0.0796	0.039*
H6	0.3495	0.4738	0.1587	0.035*
H8A	0.0177	0.7371	0.2697	0.056*
H8B	−0.0769	0.8177	0.2204	0.056*
H8C	−0.0736	0.9042	0.2727	0.056*
H9A	0.3698	1.0096	0.2835	0.051*
H9B	0.2777	0.8800	0.3140	0.051*
H9C	0.1890	1.0483	0.3052	0.051*
H10A	0.4975	0.8918	0.1369	0.042*
H10B	0.5435	0.7713	0.1815	0.042*
H10C	0.6367	0.9386	0.1833	0.042*
H11A	0.2627	1.1474	0.2072	0.044*
H11B	0.3703	1.1477	0.1602	0.044*
H11C	0.4734	1.1611	0.2150	0.044*
H13A	0.1301	1.1851	0.0769	0.042*
H13B	0.0290	1.2483	0.1211	0.042*
H13C	−0.0180	1.3169	0.0664	0.042*
H14A	−0.2900	1.1932	0.1169	0.045*
H14B	−0.3749	1.0680	0.0774	0.045*
H14C	−0.3297	1.2396	0.0597	0.045*
H15A	−0.1320	0.6963	0.1250	0.040*
H15B	−0.1390	0.6132	0.0722	0.040*
H15C	−0.3183	0.6585	0.0936	0.040*
H16A	−0.2713	0.7682	−0.0013	0.047*
H16B	−0.2824	0.9533	0.0050	0.047*
H16C	−0.4273	0.8433	0.0252	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0220 (6)	0.0224 (6)	0.0289 (7)	−0.0031 (5)	0.0014 (5)	−0.0012 (5)
C2	0.0234 (6)	0.0206 (6)	0.0282 (7)	−0.0018 (5)	0.0019 (5)	−0.0013 (5)
C3	0.0318 (7)	0.0282 (7)	0.0290 (7)	−0.0036 (5)	0.0024 (5)	−0.0013 (5)
C4	0.0352 (8)	0.0325 (7)	0.0346 (8)	−0.0053 (6)	0.0102 (6)	−0.0098 (6)
C5	0.0273 (7)	0.0240 (6)	0.0477 (9)	0.0001 (5)	0.0059 (6)	−0.0092 (6)
C6	0.0268 (7)	0.0221 (6)	0.0375 (8)	−0.0004 (5)	−0.0021 (6)	0.0006 (5)
C7	0.0242 (6)	0.0247 (6)	0.0245 (7)	0.0004 (5)	−0.0007 (5)	0.0027 (5)
C8	0.0408 (9)	0.0560 (10)	0.0462 (10)	−0.0088 (7)	0.0189 (7)	−0.0091 (8)
C9	0.0550 (10)	0.0431 (8)	0.0272 (8)	−0.0029 (7)	−0.0004 (7)	−0.0069 (6)
C10	0.0239 (7)	0.0340 (7)	0.0485 (9)	−0.0021 (6)	0.0058 (6)	−0.0026 (6)
C11	0.0400 (8)	0.0246 (7)	0.0464 (9)	−0.0044 (6)	0.0082 (7)	−0.0001 (6)
C12	0.0291 (7)	0.0214 (6)	0.0205 (6)	−0.0002 (5)	0.0057 (5)	−0.0002 (5)
C13	0.0388 (8)	0.0239 (7)	0.0423 (9)	−0.0022 (6)	0.0009 (6)	0.0012 (6)
C14	0.0370 (8)	0.0325 (7)	0.0446 (9)	0.0074 (6)	0.0101 (6)	0.0001 (6)
C15	0.0321 (8)	0.0261 (7)	0.0433 (9)	−0.0047 (5)	0.0066 (6)	0.0051 (6)
C16	0.0419 (9)	0.0378 (8)	0.0343 (8)	−0.0067 (6)	−0.0066 (6)	0.0007 (6)
N1	0.0303 (6)	0.0247 (5)	0.0257 (6)	−0.0024 (4)	0.0016 (4)	0.0003 (4)
N2	0.0324 (6)	0.0357 (6)	0.0272 (6)	−0.0056 (5)	0.0064 (5)	−0.0047 (5)
N3	0.0265 (6)	0.0238 (5)	0.0348 (6)	−0.0020 (4)	0.0044 (5)	−0.0007 (5)
N4	0.0297 (6)	0.0208 (5)	0.0261 (6)	0.0017 (4)	0.0003 (4)	−0.0007 (4)
N5	0.0291 (6)	0.0211 (5)	0.0309 (6)	0.0026 (4)	0.0037 (5)	0.0014 (4)
N6	0.0277 (6)	0.0251 (5)	0.0288 (6)	−0.0025 (4)	0.0001 (4)	0.0023 (4)

Geometric parameters (Å, º)

C2—C1	1.4162 (18)	C6—H6	0.9500
C2—C3	1.3947 (19)	C8—H8A	0.9800
C3—C4	1.3896 (19)	C8—H8B	0.9800
C5—C4	1.381 (2)	C8—H8C	0.9800
C6—C5	1.384 (2)	C9—H9A	0.9800
C6—C1	1.3945 (18)	C9—H9B	0.9800
N1—C1	1.4023 (17)	C9—H9C	0.9800
N1—C7	1.2996 (16)	C10—H10A	0.9800
N2—C7	1.3808 (18)	C10—H10B	0.9800
N2—C8	1.4467 (19)	C10—H10C	0.9800
N2—C9	1.4531 (17)	C11—H11A	0.9800
N3—C7	1.3765 (16)	C11—H11B	0.9800
N3—C10	1.4453 (18)	C11—H11C	0.9800
N3—C11	1.4526 (17)	C13—H13A	0.9800
N4—C2	1.4120 (16)	C13—H13B	0.9800
N4—C12	1.2910 (16)	C13—H13C	0.9800
N5—C12	1.3893 (15)	C14—H14A	0.9800
N5—C13	1.4515 (17)	C14—H14B	0.9800
N5—C14	1.4520 (18)	C14—H14C	0.9800
N6—C12	1.3798 (16)	C15—H15A	0.9800
N6—C15	1.4523 (17)	C15—H15B	0.9800
N6—C16	1.4495 (17)	C15—H15C	0.9800
C3—H3	0.9500	C16—H16A	0.9800
C4—H4	0.9500	C16—H16B	0.9800
C5—H5	0.9500	C16—H16C	0.9800
C3—C2—C1	118.88 (12)	N2—C9—H9C	109.5
C3—C2—N4	121.09 (11)	N3—C10—H10A	109.5
C3—C4—C5	119.44 (13)	N3—C10—H10B	109.5
C4—C3—C2	121.55 (13)	N3—C10—H10C	109.5
C5—C6—C1	121.73 (12)	N3—C11—H11A	109.5
C6—C1—C2	118.43 (12)	N3—C11—H11B	109.5
C6—C5—C4	119.91 (13)	N3—C11—H11C	109.5
C7—N1—C1	121.65 (11)	N5—C13—H13A	109.5
C7—N2—C8	117.44 (11)	N5—C13—H13B	109.5
C7—N2—C9	119.43 (12)	N5—C13—H13C	109.5
C7—N3—C10	121.12 (11)	N5—C14—H14A	109.5
C7—N3—C11	121.63 (11)	N5—C14—H14B	109.5
C8—N2—C9	113.27 (13)	N5—C14—H14C	109.5
C11—N3—C10	114.08 (11)	N6—C15—H15A	109.5
C12—N4—C2	119.45 (10)	N6—C15—H15B	109.5
C12—N5—C13	117.56 (11)	N6—C15—H15C	109.5
C12—N5—C14	120.79 (11)	N6—C16—H16A	109.5
C12—N6—C15	120.58 (11)	N6—C16—H16B	109.5
C12—N6—C16	122.60 (11)	N6—C16—H16C	109.5
C13—N5—C14	113.05 (11)	H8A—C8—H8B	109.5
C15—N6—C16	114.80 (11)	H8A—C8—H8C	109.5
N1—C1—C2	121.42 (11)	H8B—C8—H8C	109.5
N1—C1—C6	119.71 (12)	H9A—C9—H9B	109.5
N1—C7—N2	118.78 (12)	H9A—C9—H9C	109.5
N1—C7—N3	127.03 (12)	H9B—C9—H9C	109.5
N2—C7—N3	114.13 (11)	H10A—C10—H10B	109.5
N4—C2—C1	119.93 (11)	H10A—C10—H10C	109.5
N4—C12—N5	119.00 (11)	H10B—C10—H10C	109.5
N4—C12—N6	126.66 (11)	H11A—C11—H11B	109.5
N5—C12—N6	114.32 (11)	H11A—C11—H11C	109.5
C1—C6—H6	119.1	H11B—C11—H11C	109.5
C2—C3—H3	119.2	H13A—C13—H13B	109.5
C3—C4—H4	120.3	H13A—C13—H13C	109.5
C4—C3—H3	119.2	H13B—C13—H13C	109.5
C4—C5—H5	120.0	H14A—C14—H14B	109.5
C5—C4—H4	120.3	H14A—C14—H14C	109.5
C5—C6—H6	119.1	H14B—C14—H14C	109.5
C6—C5—H5	120.0	H15A—C15—H15B	109.5
N2—C8—H8A	109.5	H15A—C15—H15C	109.5
N2—C8—H8B	109.5	H15B—C15—H15C	109.5
N2—C8—H8C	109.5	H16A—C16—H16B	109.5
N2—C9—H9A	109.5	H16A—C16—H16C	109.5
N2—C9—H9B	109.5	H16B—C16—H16C	109.5
C1—C2—C3—C4	0.9 (2)	C10—N3—C7—N1	−18.4 (2)
C1—C6—C5—C4	−1.7 (2)	C10—N3—C7—N2	158.77 (12)
C1—N1—C7—N2	155.99 (12)	C11—N3—C7—N1	140.33 (14)
C1—N1—C7—N3	−27.01 (19)	C11—N3—C7—N2	−42.55 (17)
C2—C3—C4—C5	0.6 (2)	C12—N4—C2—C3	58.28 (18)
C2—N4—C12—N5	−156.27 (11)	C12—N4—C2—C1	−125.35 (13)
C2—N4—C12—N6	25.5 (2)	C13—N5—C12—N4	7.64 (18)
C3—C2—C1—C6	−2.70 (19)	C13—N5—C12—N6	−173.90 (11)
C3—C2—C1—N1	−175.00 (11)	C14—N5—C12—N4	−137.97 (14)
C5—C6—C1—C2	3.13 (19)	C14—N5—C12—N6	40.50 (16)
C5—C6—C1—N1	175.56 (12)	C15—N6—C12—N4	25.5 (2)
C6—C5—C4—C3	−0.3 (2)	C15—N6—C12—N5	−152.84 (12)
C7—N1—C1—C2	−58.19 (17)	C16—N6—C12—N4	−137.47 (15)
C7—N1—C1—C6	129.61 (13)	C16—N6—C12—N5	44.20 (18)
C8—N2—C7—N1	−12.47 (19)	N4—C2—C1—C6	−179.15 (11)
C8—N2—C7—N3	170.16 (12)	N4—C2—C1—N1	8.55 (18)
C9—N2—C7—N1	131.06 (13)	N4—C2—C3—C4	177.30 (12)
C9—N2—C7—N3	−46.32 (17)