2-[2-(Methyl­ammonio)ethyl­iminiometh­yl]-4-nitro­phenolate nitrate

The title compound, C₁₀H₁₄N₃O₃⁺·NO₃⁻, is a nitrate salt of the Schiff base 4-nitro-2-[2-(methyl­amino)ethyl­imino­meth­yl]phenol. The mol­ecule adopts a trans configuration about the C=N double bond. In the crystal structure, mol­ecules are linked through inter­molecular N—H...O hydrogen bonds, forming layers parallel to the ab plane.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.071
• wR factor = 0.164
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.103
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.10
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N4
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

2-[2-(Methylammonio)ethyliminiomethyl]-4-nitrophenolate nitrate

Crystal data

C10H14N3O3^+·NO3^−	F(000) = 1200
Mr = 286.25	Dx = 1.527 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 693 reflections
a = 7.119 (2) Å	θ = 2.4–24.3°
b = 16.922 (4) Å	µ = 0.13 mm^−1
c = 20.671 (5) Å	T = 298 K
V = 2490.2 (11) Å^3	Plate, yellow
Z = 8	0.16 × 0.10 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2564 independent reflections
Radiation source: fine-focus sealed tube	1430 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.103
ω scans	θmax = 26.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.980, Tmax = 0.994	k = −21→21
13625 measured reflections	l = −24→25

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0371P)^2 + 2.2208P] where P = (Fo^2 + 2Fc^2)/3
2564 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.26 e Å^−3
1 restraint	Δρmin = −0.24 e Å^−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
O1	0.6212 (6)	0.47863 (19)	0.27171 (18)	0.0992 (14)
O2	0.6643 (4)	0.48186 (15)	0.37410 (15)	0.0600 (9)
O3	1.0208 (3)	0.15519 (13)	0.31232 (11)	0.0394 (7)
O4	0.6855 (5)	0.09757 (17)	0.51453 (13)	0.0673 (9)
O5	0.8001 (5)	0.21127 (15)	0.54009 (14)	0.0692 (10)
O6	0.8237 (4)	0.11342 (15)	0.60515 (14)	0.0571 (8)
N1	0.6790 (5)	0.44867 (19)	0.32137 (19)	0.0505 (9)
N2	0.9874 (4)	0.16040 (16)	0.18660 (14)	0.0316 (7)
N3	0.7217 (4)	0.05317 (15)	0.10461 (13)	0.0319 (7)
H3A	0.6716	0.0045	0.1080	0.038*
H3B	0.6730	0.0828	0.1366	0.038*
N4	0.7695 (4)	0.14151 (18)	0.55242 (15)	0.0417 (8)
C1	0.8835 (5)	0.26283 (17)	0.25723 (16)	0.0276 (8)
C2	0.9404 (5)	0.22234 (19)	0.31476 (17)	0.0317 (8)
C3	0.9009 (5)	0.2614 (2)	0.37426 (17)	0.0411 (9)
H3	0.9324	0.2367	0.4130	0.049*
C4	0.8182 (5)	0.3338 (2)	0.37600 (19)	0.0439 (10)
H4	0.7953	0.3581	0.4156	0.053*
C5	0.7675 (5)	0.3720 (2)	0.31888 (19)	0.0383 (9)
C6	0.7998 (5)	0.33723 (19)	0.25997 (17)	0.0349 (9)
H6	0.7660	0.3632	0.2221	0.042*
C7	0.9143 (5)	0.22933 (18)	0.19488 (17)	0.0303 (8)
H7	0.8802	0.2585	0.1586	0.036*
C8	1.0275 (5)	0.12536 (19)	0.12326 (17)	0.0357 (9)
H8A	1.1619	0.1175	0.1189	0.043*
H8B	0.9877	0.1615	0.0895	0.043*
C9	0.9280 (5)	0.04709 (19)	0.11460 (18)	0.0349 (9)
H9A	0.9826	0.0201	0.0777	0.042*
H9B	0.9511	0.0148	0.1525	0.042*
C10	0.6638 (6)	0.0874 (2)	0.04214 (18)	0.0494 (11)
H10A	0.7101	0.1405	0.0389	0.074*
H10B	0.5291	0.0877	0.0394	0.074*
H10C	0.7143	0.0562	0.0075	0.074*
H2	1.020 (6)	0.134 (2)	0.2232 (13)	0.083 (17)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.155 (4)	0.064 (2)	0.079 (3)	0.057 (2)	−0.032 (3)	−0.0162 (18)
O2	0.0510 (18)	0.0506 (17)	0.078 (2)	0.0021 (14)	0.0060 (16)	−0.0342 (16)
O3	0.0495 (16)	0.0307 (14)	0.0378 (15)	0.0077 (12)	−0.0070 (12)	0.0014 (11)
O4	0.102 (3)	0.0552 (18)	0.0449 (18)	−0.0122 (17)	−0.0273 (18)	−0.0036 (14)
O5	0.105 (3)	0.0349 (16)	0.068 (2)	−0.0092 (16)	0.0114 (19)	0.0114 (14)
O6	0.082 (2)	0.0414 (15)	0.0475 (17)	0.0004 (14)	−0.0235 (16)	0.0038 (13)
N1	0.047 (2)	0.044 (2)	0.061 (2)	0.0047 (17)	−0.0023 (19)	−0.0180 (19)
N2	0.0306 (16)	0.0307 (17)	0.0335 (18)	0.0008 (13)	−0.0020 (14)	−0.0056 (14)
N3	0.0308 (17)	0.0302 (15)	0.0347 (17)	−0.0024 (13)	0.0050 (14)	−0.0058 (13)
N4	0.049 (2)	0.0372 (18)	0.038 (2)	0.0045 (16)	0.0056 (17)	0.0025 (15)
C1	0.0270 (18)	0.0288 (17)	0.027 (2)	−0.0040 (15)	−0.0001 (15)	−0.0037 (15)
C2	0.0280 (19)	0.031 (2)	0.036 (2)	−0.0077 (15)	−0.0010 (17)	−0.0017 (16)
C3	0.049 (2)	0.045 (2)	0.029 (2)	−0.0071 (19)	−0.0050 (19)	−0.0009 (17)
C4	0.044 (2)	0.051 (2)	0.037 (2)	−0.003 (2)	−0.0009 (19)	−0.0158 (19)
C5	0.0304 (19)	0.036 (2)	0.048 (2)	0.0020 (16)	−0.0002 (18)	−0.0139 (17)
C6	0.032 (2)	0.0318 (18)	0.041 (2)	0.0015 (16)	−0.0058 (17)	−0.0007 (16)
C7	0.0291 (19)	0.0258 (19)	0.036 (2)	−0.0027 (15)	−0.0015 (16)	−0.0003 (15)
C8	0.032 (2)	0.040 (2)	0.035 (2)	−0.0025 (17)	0.0064 (17)	−0.0116 (17)
C9	0.033 (2)	0.0331 (19)	0.039 (2)	0.0023 (16)	0.0009 (17)	−0.0069 (16)
C10	0.059 (3)	0.047 (2)	0.042 (2)	0.000 (2)	−0.009 (2)	0.0051 (19)

Geometric parameters (Å, º)

O1—N1	1.217 (4)	C2—C3	1.424 (5)
O2—N1	1.231 (4)	C3—C4	1.360 (5)
O3—C2	1.273 (4)	C3—H3	0.9300
O4—N4	1.235 (4)	C4—C5	1.393 (5)
O5—N4	1.227 (4)	C4—H4	0.9300
O6—N4	1.250 (4)	C5—C6	1.372 (5)
N1—C5	1.444 (5)	C6—H6	0.9300
N2—C7	1.289 (4)	C7—H7	0.9300
N2—C8	1.465 (4)	C8—C9	1.513 (4)
N2—H2	0.91 (3)	C8—H8A	0.9700
N3—C10	1.474 (4)	C8—H8B	0.9700
N3—C9	1.487 (4)	C9—H9A	0.9700
N3—H3A	0.9000	C9—H9B	0.9700
N3—H3B	0.9000	C10—H10A	0.9600
C1—C6	1.394 (4)	C10—H10B	0.9600
C1—C7	1.425 (5)	C10—H10C	0.9600
C1—C2	1.431 (5)
O1—N1—O2	121.9 (4)	C6—C5—C4	120.7 (3)
O1—N1—C5	119.5 (3)	C6—C5—N1	119.4 (4)
O2—N1—C5	118.6 (4)	C4—C5—N1	119.9 (3)
C7—N2—C8	124.3 (3)	C5—C6—C1	119.6 (3)
C7—N2—H2	116 (3)	C5—C6—H6	120.2
C8—N2—H2	120 (3)	C1—C6—H6	120.2
C10—N3—C9	115.2 (3)	N2—C7—C1	122.9 (3)
C10—N3—H3A	108.5	N2—C7—H7	118.6
C9—N3—H3A	108.5	C1—C7—H7	118.6
C10—N3—H3B	108.5	N2—C8—C9	111.7 (3)
C9—N3—H3B	108.5	N2—C8—H8A	109.3
H3A—N3—H3B	107.5	C9—C8—H8A	109.3
O5—N4—O4	122.2 (3)	N2—C8—H8B	109.3
O5—N4—O6	119.5 (3)	C9—C8—H8B	109.3
O4—N4—O6	118.3 (3)	H8A—C8—H8B	108.0
C6—C1—C7	117.5 (3)	N3—C9—C8	114.7 (3)
C6—C1—C2	121.3 (3)	N3—C9—H9A	108.6
C7—C1—C2	121.2 (3)	C8—C9—H9A	108.6
O3—C2—C3	122.5 (3)	N3—C9—H9B	108.6
O3—C2—C1	121.4 (3)	C8—C9—H9B	108.6
C3—C2—C1	116.1 (3)	H9A—C9—H9B	107.6
C4—C3—C2	121.8 (3)	N3—C10—H10A	109.5
C4—C3—H3	119.1	N3—C10—H10B	109.5
C2—C3—H3	119.1	H10A—C10—H10B	109.5
C3—C4—C5	120.5 (3)	N3—C10—H10C	109.5
C3—C4—H4	119.8	H10A—C10—H10C	109.5
C5—C4—H4	119.8	H10B—C10—H10C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O6^i	0.90	2.00	2.838 (5)	155
N3—H3A···O2^ii	0.90	2.45	3.033 (4)	123
N3—H3B···O3^iii	0.90	1.95	2.824 (4)	165
N2—H2···O3	0.91 (3)	1.88 (3)	2.611 (4)	137 (4)

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