N-o-Tolyl-benzamidine.

The asymmetric unit of the title compound, C(14)H(14)N(2), contains two independent mol-ecules with slightly different conformations; the dihedral angles formed by aromatic rings in the two mol-ecules are 73.2 (1) and 75.0 (1)°. Inter-molecular N-H⋯N hydrogen bonds link the mol-ecules into chains extended in the [100] direction.

Related literature

For general background, see Bourget-Merle et al. (2002 ▶). For a related crystal structure, see Surma et al. (1988 ▶).

Experimental

Crystal data

C14H14N2

M = 210.27

Triclinic,

a = 10.347 (2) Å

b = 10.697 (2) Å

c = 11.495 (2) Å

α = 97.088 (4)°

β = 103.184 (4)°

γ = 95.898 (4)°

V = 1218.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 298 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.980, T max = 0.986

4978 measured reflections

4158 independent reflections

2913 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.235

S = 1.09

4158 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.46 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017625/cv2419sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017625/cv2419Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H14N2	Z = 4
Mr = 210.27	F000 = 448
Triclinic, P1	Dx = 1.147 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 10.347 (2) Å	Cell parameters from 2024 reflections
b = 10.697 (2) Å	θ = 2.4–27.7º
c = 11.495 (2) Å	µ = 0.07 mm−1
α = 97.088 (4)º	T = 298 (2) K
β = 103.184 (4)º	Plate, colourless
γ = 95.898 (4)º	0.30 × 0.20 × 0.20 mm
V = 1218.0 (4) Å3

Siemens SMART CCD area-detector diffractometer	4158 independent reflections
Radiation source: fine-focus sealed tube	2913 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.021
T = 298(2) K	θmax = 25.0º
ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1997)	h = −10→12
Tmin = 0.980, Tmax = 0.986	k = −12→12
4978 measured reflections	l = −13→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.073	H-atom parameters constrained
wR(F2) = 0.235	w = 1/[σ2(Fo2) + (0.1497P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
4158 reflections	Δρmax = 0.44 e Å−3
291 parameters	Δρmin = −0.46 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
N1	0.90491 (17)	0.79986 (19)	0.88806 (17)	0.0538 (5)
N2	0.69224 (19)	0.8197 (2)	0.9148 (2)	0.0688 (6)
H2A	0.6726	0.8582	0.8530	0.083*
H2B	0.6343	0.8055	0.9564	0.083*
C1	0.7749 (4)	0.6552 (3)	0.6545 (3)	0.1043 (12)
H1A	0.7196	0.6274	0.5744	0.156*
H1B	0.7251	0.6362	0.7126	0.156*
H1C	0.8527	0.6121	0.6659	0.156*
C2	0.8172 (3)	0.7949 (3)	0.6711 (2)	0.0644 (7)
C3	0.8023 (3)	0.8623 (3)	0.5739 (3)	0.0852 (9)
H3	0.7654	0.8180	0.4965	0.102*
C4	0.8387 (4)	0.9873 (4)	0.5865 (3)	0.0972 (11)
H4	0.8248	1.0285	0.5189	0.117*
C5	0.8971 (4)	1.0561 (3)	0.7000 (3)	0.0927 (10)
H5	0.9236	1.1433	0.7096	0.111*
C6	0.9149 (3)	0.9920 (3)	0.7983 (3)	0.0680 (7)
H6	0.9543	1.0371	0.8749	0.082*
C7	0.8762 (2)	0.8639 (2)	0.7862 (2)	0.0508 (6)
C8	0.81298 (19)	0.7817 (2)	0.9464 (2)	0.0478 (5)
C9	0.8415 (2)	0.7144 (2)	1.05346 (19)	0.0490 (6)
C10	0.9449 (3)	0.6419 (2)	1.0709 (2)	0.0647 (7)
H10	0.9974	0.6353	1.0152	0.078*
C11	0.9718 (3)	0.5790 (3)	1.1693 (3)	0.0786 (8)
H11	1.0427	0.5313	1.1796	0.094*
C12	0.8962 (3)	0.5858 (3)	1.2516 (3)	0.0787 (8)
H12	0.9148	0.5427	1.3177	0.094*
C13	0.7939 (3)	0.6555 (4)	1.2367 (3)	0.0889 (10)
H13	0.7411	0.6594	1.2922	0.107*
C14	0.7669 (3)	0.7217 (3)	1.1390 (3)	0.0772 (8)
H14	0.6977	0.7715	1.1312	0.093*
N3	0.42879 (17)	0.78365 (18)	0.99087 (16)	0.0513 (5)
N4	0.20510 (18)	0.8125 (2)	0.96875 (18)	0.0692 (7)
H4A	0.2161	0.8348	1.0452	0.083*
H4B	0.1275	0.8098	0.9206	0.083*
C15	0.3694 (4)	0.5807 (3)	1.1207 (3)	0.0896 (9)
H15A	0.3615	0.5260	1.1796	0.134*
H15B	0.4309	0.5519	1.0755	0.134*
H15C	0.2832	0.5790	1.0667	0.134*
C16	0.4201 (2)	0.7134 (3)	1.1833 (2)	0.0616 (7)
C17	0.4444 (3)	0.7462 (4)	1.3083 (3)	0.0825 (9)
H17	0.4277	0.6830	1.3538	0.099*
C18	0.4913 (3)	0.8661 (4)	1.3665 (3)	0.0901 (10)
H18	0.5050	0.8843	1.4500	0.108*
C19	0.5182 (3)	0.9601 (3)	1.3013 (3)	0.0863 (9)
H19	0.5513	1.0424	1.3405	0.104*
C20	0.4963 (2)	0.9325 (3)	1.1778 (2)	0.0642 (7)
H20	0.5155	0.9965	1.1340	0.077*
C21	0.44635 (19)	0.8118 (2)	1.1180 (2)	0.0495 (6)
C22	0.3093 (2)	0.7819 (2)	0.9244 (2)	0.0484 (6)
C23	0.2832 (2)	0.7442 (2)	0.7916 (2)	0.0515 (6)
C24	0.1744 (3)	0.7776 (3)	0.7119 (2)	0.0671 (7)
H24	0.1161	0.8262	0.7416	0.081*
C25	0.1519 (3)	0.7395 (3)	0.5887 (3)	0.0783 (8)
H25	0.0783	0.7621	0.5364	0.094*
C26	0.2365 (3)	0.6692 (3)	0.5435 (3)	0.0816 (9)
H26	0.2214	0.6442	0.4606	0.098*
C27	0.3439 (3)	0.6357 (3)	0.6208 (3)	0.0833 (9)
H27	0.4020	0.5878	0.5900	0.100*
C28	0.3671 (3)	0.6717 (3)	0.7434 (2)	0.0671 (7)
H28	0.4402	0.6471	0.7947	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0370 (9)	0.0696 (13)	0.0553 (11)	0.0099 (8)	0.0100 (8)	0.0120 (9)
N2	0.0402 (10)	0.0939 (16)	0.0826 (15)	0.0198 (10)	0.0210 (9)	0.0325 (12)
C1	0.136 (3)	0.0662 (19)	0.087 (2)	−0.0047 (19)	−0.008 (2)	0.0009 (16)
C2	0.0606 (15)	0.0661 (16)	0.0609 (16)	0.0095 (12)	0.0040 (12)	0.0082 (12)
C3	0.097 (2)	0.090 (2)	0.0601 (17)	0.0134 (18)	−0.0004 (15)	0.0146 (15)
C4	0.113 (3)	0.091 (2)	0.085 (2)	0.006 (2)	0.0080 (19)	0.0392 (19)
C5	0.104 (2)	0.0664 (18)	0.102 (3)	−0.0002 (17)	0.011 (2)	0.0254 (18)
C6	0.0624 (15)	0.0669 (17)	0.0694 (17)	0.0030 (12)	0.0100 (12)	0.0065 (13)
C7	0.0348 (10)	0.0583 (14)	0.0591 (14)	0.0068 (9)	0.0100 (9)	0.0097 (11)
C8	0.0341 (10)	0.0521 (12)	0.0541 (13)	0.0056 (9)	0.0086 (9)	0.0012 (10)
C9	0.0395 (11)	0.0524 (13)	0.0521 (13)	0.0010 (9)	0.0099 (9)	0.0036 (10)
C10	0.0629 (15)	0.0667 (15)	0.0732 (17)	0.0202 (12)	0.0252 (12)	0.0186 (13)
C11	0.084 (2)	0.0766 (19)	0.085 (2)	0.0262 (15)	0.0248 (16)	0.0298 (16)
C12	0.081 (2)	0.083 (2)	0.0711 (18)	0.0027 (16)	0.0123 (15)	0.0273 (15)
C13	0.081 (2)	0.129 (3)	0.0676 (18)	0.020 (2)	0.0328 (15)	0.0283 (18)
C14	0.0590 (16)	0.111 (2)	0.0723 (18)	0.0303 (16)	0.0254 (13)	0.0215 (16)
N3	0.0377 (10)	0.0634 (12)	0.0546 (11)	0.0068 (8)	0.0148 (8)	0.0084 (9)
N4	0.0381 (10)	0.1089 (17)	0.0584 (12)	0.0166 (11)	0.0105 (9)	0.0006 (12)
C15	0.102 (2)	0.0692 (19)	0.097 (2)	−0.0074 (16)	0.0294 (18)	0.0172 (16)
C16	0.0501 (13)	0.0753 (17)	0.0631 (16)	0.0099 (12)	0.0184 (11)	0.0142 (13)
C17	0.0803 (19)	0.113 (3)	0.0645 (18)	0.0232 (18)	0.0261 (15)	0.0285 (18)
C18	0.091 (2)	0.119 (3)	0.0580 (17)	0.020 (2)	0.0182 (16)	−0.0026 (19)
C19	0.083 (2)	0.092 (2)	0.074 (2)	0.0097 (17)	0.0135 (16)	−0.0152 (17)
C20	0.0555 (14)	0.0655 (16)	0.0695 (17)	0.0087 (12)	0.0147 (12)	0.0029 (13)
C21	0.0333 (10)	0.0609 (14)	0.0554 (14)	0.0077 (9)	0.0138 (9)	0.0066 (11)
C22	0.0373 (11)	0.0519 (12)	0.0572 (14)	0.0038 (9)	0.0151 (9)	0.0086 (10)
C23	0.0422 (12)	0.0549 (13)	0.0571 (14)	−0.0001 (10)	0.0140 (10)	0.0094 (10)
C24	0.0588 (15)	0.0825 (18)	0.0636 (16)	0.0168 (13)	0.0156 (12)	0.0177 (13)
C25	0.0736 (18)	0.097 (2)	0.0599 (17)	0.0079 (16)	0.0039 (14)	0.0204 (15)
C26	0.083 (2)	0.100 (2)	0.0561 (16)	−0.0026 (17)	0.0186 (15)	0.0018 (15)
C27	0.0714 (18)	0.102 (2)	0.0710 (19)	0.0136 (16)	0.0196 (15)	−0.0133 (16)
C28	0.0532 (14)	0.0801 (17)	0.0639 (16)	0.0121 (12)	0.0113 (12)	−0.0014 (13)

N1—C8	1.295 (3)	N3—C22	1.294 (3)
N1—C7	1.417 (3)	N3—C21	1.421 (3)
N2—C8	1.338 (3)	N4—C22	1.346 (3)
N2—H2A	0.8600	N4—H4A	0.8600
N2—H2B	0.8600	N4—H4B	0.8600
C1—C2	1.490 (4)	C15—C16	1.493 (4)
C1—H1A	0.9600	C15—H15A	0.9600
C1—H1B	0.9600	C15—H15B	0.9600
C1—H1C	0.9600	C15—H15C	0.9600
C2—C3	1.391 (4)	C16—C17	1.394 (4)
C2—C7	1.402 (3)	C16—C21	1.405 (3)
C3—C4	1.332 (4)	C17—C18	1.357 (5)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.386 (5)	C18—C19	1.368 (5)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.379 (4)	C19—C20	1.375 (4)
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.369 (3)	C20—C21	1.374 (3)
C6—H6	0.9300	C20—H20	0.9300
C8—C9	1.489 (3)	C22—C23	1.485 (3)
C9—C10	1.377 (3)	C23—C28	1.384 (3)
C9—C14	1.381 (3)	C23—C24	1.388 (3)
C10—C11	1.375 (4)	C24—C25	1.383 (4)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.359 (4)	C25—C26	1.359 (4)
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.347 (4)	C26—C27	1.364 (4)
C12—H12	0.9300	C26—H26	0.9300
C13—C14	1.391 (4)	C27—C28	1.373 (4)
C13—H13	0.9300	C27—H27	0.9300
C14—H14	0.9300	C28—H28	0.9300
C8—N1—C7	118.20 (18)	C22—N3—C21	116.93 (17)
C8—N2—H2A	120.0	C22—N4—H4A	120.0
C8—N2—H2B	120.0	C22—N4—H4B	120.0
H2A—N2—H2B	120.0	H4A—N4—H4B	120.0
C2—C1—H1A	109.5	C16—C15—H15A	109.5
C2—C1—H1B	109.5	C16—C15—H15B	109.5
H1A—C1—H1B	109.5	H15A—C15—H15B	109.5
C2—C1—H1C	109.5	C16—C15—H15C	109.5
H1A—C1—H1C	109.5	H15A—C15—H15C	109.5
H1B—C1—H1C	109.5	H15B—C15—H15C	109.5
C3—C2—C7	117.1 (3)	C17—C16—C21	116.7 (3)
C3—C2—C1	121.9 (3)	C17—C16—C15	122.3 (3)
C7—C2—C1	121.0 (3)	C21—C16—C15	121.1 (2)
C4—C3—C2	123.0 (3)	C18—C17—C16	122.9 (3)
C4—C3—H3	118.5	C18—C17—H17	118.5
C2—C3—H3	118.5	C16—C17—H17	118.5
C3—C4—C5	120.2 (3)	C17—C18—C19	119.4 (3)
C3—C4—H4	119.9	C17—C18—H18	120.3
C5—C4—H4	119.9	C19—C18—H18	120.3
C6—C5—C4	118.3 (3)	C18—C19—C20	119.8 (3)
C6—C5—H5	120.9	C18—C19—H19	120.1
C4—C5—H5	120.9	C20—C19—H19	120.1
C7—C6—C5	121.8 (3)	C21—C20—C19	121.0 (3)
C7—C6—H6	119.1	C21—C20—H20	119.5
C5—C6—H6	119.1	C19—C20—H20	119.5
C6—C7—C2	119.5 (2)	C20—C21—C16	120.1 (2)
C6—C7—N1	120.1 (2)	C20—C21—N3	120.4 (2)
C2—C7—N1	120.2 (2)	C16—C21—N3	119.4 (2)
N1—C8—N2	123.3 (2)	N3—C22—N4	123.7 (2)
N1—C8—C9	118.86 (18)	N3—C22—C23	119.19 (19)
N2—C8—C9	117.84 (19)	N4—C22—C23	117.14 (19)
C10—C9—C14	117.2 (2)	C28—C23—C24	117.7 (2)
C10—C9—C8	120.7 (2)	C28—C23—C22	120.2 (2)
C14—C9—C8	122.1 (2)	C24—C23—C22	122.1 (2)
C11—C10—C9	121.2 (3)	C25—C24—C23	120.7 (3)
C11—C10—H10	119.4	C25—C24—H24	119.7
C9—C10—H10	119.4	C23—C24—H24	119.7
C12—C11—C10	120.8 (3)	C26—C25—C24	120.5 (3)
C12—C11—H11	119.6	C26—C25—H25	119.8
C10—C11—H11	119.6	C24—C25—H25	119.8
C13—C12—C11	119.5 (3)	C25—C26—C27	119.5 (3)
C13—C12—H12	120.3	C25—C26—H26	120.2
C11—C12—H12	120.3	C27—C26—H26	120.2
C12—C13—C14	120.5 (3)	C26—C27—C28	120.8 (3)
C12—C13—H13	119.8	C26—C27—H27	119.6
C14—C13—H13	119.8	C28—C27—H27	119.6
C9—C14—C13	120.9 (3)	C27—C28—C23	120.9 (3)
C9—C14—H14	119.6	C27—C28—H28	119.6
C13—C14—H14	119.6	C23—C28—H28	119.6
C7—C2—C3—C4	−1.5 (5)	C21—C16—C17—C18	−0.1 (4)
C1—C2—C3—C4	179.6 (3)	C15—C16—C17—C18	179.6 (3)
C2—C3—C4—C5	1.5 (6)	C16—C17—C18—C19	−0.9 (5)
C3—C4—C5—C6	−0.6 (6)	C17—C18—C19—C20	0.7 (5)
C4—C5—C6—C7	−0.2 (5)	C18—C19—C20—C21	0.6 (4)
C5—C6—C7—C2	0.2 (4)	C19—C20—C21—C16	−1.6 (3)
C5—C6—C7—N1	175.4 (3)	C19—C20—C21—N3	−177.7 (2)
C3—C2—C7—C6	0.6 (4)	C17—C16—C21—C20	1.4 (3)
C1—C2—C7—C6	179.5 (3)	C15—C16—C21—C20	−178.3 (3)
C3—C2—C7—N1	−174.6 (2)	C17—C16—C21—N3	177.5 (2)
C1—C2—C7—N1	4.3 (4)	C15—C16—C21—N3	−2.2 (3)
C8—N1—C7—C6	95.6 (3)	C22—N3—C21—C20	−98.8 (2)
C8—N1—C7—C2	−89.2 (3)	C22—N3—C21—C16	85.1 (3)
C7—N1—C8—N2	0.4 (3)	C21—N3—C22—N4	4.2 (3)
C7—N1—C8—C9	179.91 (19)	C21—N3—C22—C23	−175.76 (19)
N1—C8—C9—C10	−18.2 (3)	N3—C22—C23—C28	22.1 (3)
N2—C8—C9—C10	161.3 (2)	N4—C22—C23—C28	−157.9 (2)
N1—C8—C9—C14	161.7 (2)	N3—C22—C23—C24	−159.0 (2)
N2—C8—C9—C14	−18.8 (3)	N4—C22—C23—C24	21.1 (3)
C14—C9—C10—C11	0.3 (4)	C28—C23—C24—C25	−0.1 (4)
C8—C9—C10—C11	−179.8 (2)	C22—C23—C24—C25	−179.1 (2)
C9—C10—C11—C12	0.6 (5)	C23—C24—C25—C26	−0.4 (4)
C10—C11—C12—C13	−0.3 (5)	C24—C25—C26—C27	0.4 (5)
C11—C12—C13—C14	−1.0 (5)	C25—C26—C27—C28	0.2 (5)
C10—C9—C14—C13	−1.5 (4)	C26—C27—C28—C23	−0.7 (5)
C8—C9—C14—C13	178.5 (3)	C24—C23—C28—C27	0.7 (4)
C12—C13—C14—C9	1.9 (5)	C22—C23—C28—C27	179.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N3	0.86	2.25	3.049 (3)	156
N4—H4B···N1i	0.86	2.24	3.016 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯N3	0.86	2.25	3.049 (3)	156
N4—H4B⋯N1i	0.86	2.24	3.016 (3)	151

Symmetry code: (i) .