1,5-Di­amino­naphthalene

The title compound, C₁₀H₁₀N₂, crystallizes with one and a half mol­ecules in the asymmetric unit, one lying on a general position and the other on an inversion centre. The dihedral angle between these two mol­ecules is 73.30 (4)°.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.118
• Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.65 mm
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1B    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N5     -   H5A    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N5     -   H5B    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N11    -   H11A   ...          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   4 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

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Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.

1,5-Diaminonaphthalene

Crystal data

C10H10N2	F(000) = 504
Mr = 158.20	Dx = 1.302 Mg m^−3
Monoclinic, P21/c	Melting point: 458 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.1790 (7) Å	Cell parameters from 75 reflections
b = 11.0081 (18) Å	θ = 5.1–11.9°
c = 21.238 (3) Å	µ = 0.08 mm^−1
β = 90.679 (10)°	T = 296 K
V = 1210.7 (3) Å^3	Plate, brown
Z = 6	0.65 × 0.18 × 0.08 mm

Data collection

Bruker P4 diffractometer	Rint = 0.023
Radiation source: fine-focus sealed tube, FN4	θmax = 25.0°, θmin = 1.9°
Graphite monochromator	h = −6→2
ω scans	k = −1→13
3277 measured reflections	l = −25→25
2117 independent reflections	3 standard reflections every 97 reflections
1259 reflections with I > 2σ(I)	intensity decay: <1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: geom + difmap
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0551P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
2117 reflections	Δρmax = 0.11 e Å^−3
188 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXTL-Plus (Sheldrick, 1998), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (3)

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
N1	0.1882 (4)	0.7292 (2)	0.14149 (12)	0.0745 (6)
H1A	0.130 (5)	0.764 (2)	0.1771 (12)	0.089 (9)*
H1B	0.076 (4)	0.723 (2)	0.1124 (10)	0.081 (8)*
C1	0.3564 (4)	0.63152 (18)	0.14524 (9)	0.0594 (6)
C2	0.3801 (5)	0.5513 (2)	0.09579 (9)	0.0722 (6)
H2A	0.2713	0.5587	0.0608	0.087*
C3	0.5650 (5)	0.4593 (2)	0.09746 (10)	0.0759 (7)
H3A	0.5775	0.4066	0.0634	0.091*
C4	0.7272 (4)	0.44450 (18)	0.14756 (9)	0.0661 (6)
H4A	0.8502	0.3830	0.1473	0.079*
C5	0.8711 (4)	0.51086 (18)	0.25458 (9)	0.0564 (5)
N5	1.0532 (4)	0.41626 (19)	0.25897 (13)	0.0747 (6)
H5A	1.108 (5)	0.397 (2)	0.2196 (12)	0.104 (10)*
H5B	1.158 (5)	0.430 (2)	0.2900 (11)	0.085 (9)*
C6	0.8388 (4)	0.58686 (19)	0.30511 (9)	0.0632 (6)
H6A	0.9440	0.5777	0.3406	0.076*
C7	0.6508 (4)	0.67771 (19)	0.30422 (9)	0.0614 (6)
H7A	0.6322	0.7278	0.3392	0.074*
C8	0.4946 (4)	0.69413 (18)	0.25311 (9)	0.0583 (5)
H8A	0.3712	0.7555	0.2531	0.070*
C9	0.5196 (4)	0.61744 (16)	0.19953 (8)	0.0507 (5)
C10	0.7086 (4)	0.52369 (17)	0.20057 (8)	0.0528 (5)
N11	0.5825 (4)	0.5536 (3)	0.59806 (9)	0.0740 (6)
H11A	0.534 (5)	0.481 (2)	0.5995 (11)	0.089 (9)*
H11B	0.462 (5)	0.614 (2)	0.6061 (10)	0.091 (8)*
C11	0.7452 (4)	0.5774 (2)	0.54805 (8)	0.0566 (5)
C12	0.7622 (4)	0.69414 (19)	0.52448 (9)	0.0638 (6)
H12A	0.6519	0.7540	0.5394	0.077*
C13	0.9433 (4)	0.7233 (2)	0.47848 (9)	0.0660 (6)
H13A	0.9521	0.8024	0.4632	0.079*
C14	1.1068 (4)	0.63739 (19)	0.45573 (9)	0.0610 (6)
H14A	1.2299	0.6590	0.4262	0.073*
C20	1.0915 (3)	0.51567 (18)	0.47650 (8)	0.0509 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0709 (14)	0.0785 (14)	0.0737 (14)	0.0047 (12)	−0.0126 (12)	0.0084 (11)
C1	0.0598 (14)	0.0560 (12)	0.0623 (12)	−0.0112 (11)	0.0026 (11)	0.0088 (10)
C2	0.0850 (17)	0.0733 (15)	0.0582 (12)	−0.0154 (14)	−0.0068 (11)	0.0055 (11)
C3	0.0965 (19)	0.0684 (15)	0.0629 (13)	−0.0143 (14)	0.0104 (13)	−0.0091 (11)
C4	0.0743 (15)	0.0577 (13)	0.0666 (13)	−0.0032 (11)	0.0130 (12)	−0.0054 (10)
C5	0.0478 (12)	0.0511 (12)	0.0704 (12)	−0.0033 (10)	0.0073 (10)	0.0046 (10)
N5	0.0621 (13)	0.0711 (13)	0.0908 (16)	0.0079 (11)	−0.0006 (12)	0.0015 (12)
C6	0.0622 (14)	0.0653 (13)	0.0620 (12)	−0.0063 (12)	−0.0036 (10)	0.0036 (11)
C7	0.0675 (14)	0.0589 (13)	0.0580 (12)	−0.0058 (12)	0.0039 (11)	−0.0063 (10)
C8	0.0588 (13)	0.0508 (12)	0.0655 (12)	0.0006 (10)	0.0067 (11)	0.0003 (10)
C9	0.0467 (11)	0.0499 (11)	0.0557 (11)	−0.0118 (10)	0.0047 (9)	0.0058 (9)
C10	0.0501 (12)	0.0507 (12)	0.0579 (11)	−0.0094 (10)	0.0100 (9)	0.0015 (9)
N11	0.0673 (14)	0.0798 (16)	0.0753 (13)	0.0057 (13)	0.0167 (10)	0.0016 (11)
C11	0.0477 (12)	0.0718 (14)	0.0501 (10)	0.0014 (11)	−0.0042 (9)	−0.0022 (10)
C12	0.0633 (14)	0.0660 (14)	0.0619 (12)	0.0102 (11)	−0.0038 (11)	−0.0056 (10)
C13	0.0767 (16)	0.0575 (13)	0.0637 (12)	−0.0006 (12)	−0.0062 (12)	0.0039 (10)
C14	0.0613 (14)	0.0655 (13)	0.0561 (11)	−0.0075 (12)	−0.0009 (10)	0.0042 (10)
C20	0.0441 (11)	0.0594 (12)	0.0491 (10)	−0.0022 (10)	−0.0078 (8)	−0.0013 (9)

Geometric parameters (Å, º)

N1—C1	1.385 (3)	C7—C8	1.358 (3)
N1—H1A	0.90 (2)	C7—H7A	0.9300
N1—H1B	0.85 (2)	C8—C9	1.424 (2)
C1—C2	1.379 (3)	C8—H8A	0.9300
C1—C9	1.430 (3)	C9—C10	1.423 (3)
C2—C3	1.394 (3)	N11—C11	1.388 (3)
C2—H2A	0.9300	N11—H11A	0.84 (3)
C3—C4	1.358 (3)	N11—H11B	0.93 (3)
C3—H3A	0.9300	C11—C12	1.383 (3)
C4—C10	1.428 (3)	C11—C20^i	1.431 (3)
C4—H4A	0.9300	C12—C13	1.400 (3)
C5—C6	1.373 (3)	C12—H12A	0.9300
C5—N5	1.407 (3)	C13—C14	1.362 (3)
C5—C10	1.421 (3)	C13—H13A	0.9300
N5—H5A	0.91 (2)	C14—C20	1.413 (3)
N5—H5B	0.86 (2)	C14—H14A	0.9300
C6—C7	1.396 (3)	C20—C20^i	1.427 (4)
C6—H6A	0.9300	C20—C11^i	1.431 (3)
C1—N1—H1A	119.7 (15)	C7—C8—C9	120.05 (19)
C1—N1—H1B	113.7 (16)	C7—C8—H8A	120.0
H1A—N1—H1B	114 (2)	C9—C8—H8A	120.0
C2—C1—N1	121.0 (2)	C10—C9—C8	119.13 (17)
C2—C1—C9	119.2 (2)	C10—C9—C1	119.43 (17)
N1—C1—C9	119.72 (19)	C8—C9—C1	121.43 (19)
C1—C2—C3	120.9 (2)	C5—C10—C9	119.04 (17)
C1—C2—H2A	119.6	C5—C10—C4	122.05 (19)
C3—C2—H2A	119.6	C9—C10—C4	118.90 (18)
C4—C3—C2	121.7 (2)	C11—N11—H11A	113.1 (17)
C4—C3—H3A	119.1	C11—N11—H11B	114.8 (14)
C2—C3—H3A	119.1	H11A—N11—H11B	118 (2)
C3—C4—C10	119.9 (2)	C12—C11—N11	119.6 (2)
C3—C4—H4A	120.1	C12—C11—C20^i	119.55 (18)
C10—C4—H4A	120.1	N11—C11—C20^i	120.7 (2)
C6—C5—N5	119.1 (2)	C11—C12—C13	120.8 (2)
C6—C5—C10	119.60 (18)	C11—C12—H12A	119.6
N5—C5—C10	121.1 (2)	C13—C12—H12A	119.6
C5—N5—H5A	108.9 (16)	C14—C13—C12	120.8 (2)
C5—N5—H5B	109.6 (17)	C14—C13—H13A	119.6
H5A—N5—H5B	123 (2)	C12—C13—H13A	119.6
C5—C6—C7	121.17 (19)	C13—C14—C20	120.69 (19)
C5—C6—H6A	119.4	C13—C14—H14A	119.7
C7—C6—H6A	119.4	C20—C14—H14A	119.7
C8—C7—C6	121.00 (18)	C14—C20—C20^i	119.2 (2)
C8—C7—H7A	119.5	C14—C20—C11^i	121.97 (18)
C6—C7—H7A	119.5	C20^i—C20—C11^i	118.8 (2)
N1—C1—C2—C3	174.46 (19)	N5—C5—C10—C9	177.18 (17)
C9—C1—C2—C3	−1.7 (3)	C6—C5—C10—C4	−177.73 (17)
C1—C2—C3—C4	0.3 (3)	N5—C5—C10—C4	−2.1 (3)
C2—C3—C4—C10	0.7 (3)	C8—C9—C10—C5	−1.3 (3)
N5—C5—C6—C7	−176.45 (19)	C1—C9—C10—C5	179.61 (16)
C10—C5—C6—C7	−0.7 (3)	C8—C9—C10—C4	177.96 (16)
C5—C6—C7—C8	−0.3 (3)	C1—C9—C10—C4	−1.1 (3)
C6—C7—C8—C9	0.5 (3)	C3—C4—C10—C5	178.98 (18)
C7—C8—C9—C10	0.3 (3)	C3—C4—C10—C9	−0.3 (3)
C7—C8—C9—C1	179.34 (17)	N11—C11—C12—C13	173.49 (18)
C2—C1—C9—C10	2.1 (3)	C20^i—C11—C12—C13	−2.2 (3)
N1—C1—C9—C10	−174.14 (17)	C11—C12—C13—C14	0.1 (3)
C2—C1—C9—C8	−176.94 (17)	C12—C13—C14—C20	2.2 (3)
N1—C1—C9—C8	6.8 (3)	C13—C14—C20—C20^i	−2.3 (3)
C6—C5—C10—C9	1.5 (3)	C13—C14—C20—C11^i	177.89 (17)

Symmetry code: (i) −x+2, −y+1, −z+1.