(E)-N′-Hy­droxy-N,N-dimethyl-2-(3-nitro­phen­yl)­acetimidamide

In the crystal of the title compound, C₁₀H₁₃N₂O₃, inversion dimers linked by pairs of N—H...O hydrogen bonds generate R₂²(6) loops. The dimers are linked by weak C—H...O and C—H...π inter­actions, resulting in a three-dimensional network. A short NO₂...NO₂ contact [3.107 (2) Å] is also seen.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.059
• wR factor = 0.157
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.507 Check
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as      mixed Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.006 Degree
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2018 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   5 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
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(E)-N'-Hydroxy-N,N-dimethyl-2-(3-nitrophenyl)acetimidamide

Crystal data

C10H13N3O3	Z = 2
Mr = 223.23	F(000) = 236
Triclinic, P1	Dx = 1.318 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7740 (6) Å	Cell parameters from 2839 reflections
b = 8.4772 (5) Å	θ = 4.1–28.1°
c = 9.6599 (7) Å	µ = 0.10 mm^−1
α = 66.595 (6)°	T = 293 K
β = 77.917 (6)°	Block, colourless
γ = 76.113 (6)°	0.25 × 0.22 × 0.12 mm
V = 562.49 (7) Å^3

Data collection

Bruker APEXII CCD diffractometer	2097 independent reflections
Radiation source: fine-focus sealed tube	1722 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω scans	θmax = 25.5°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2015)	h = −9→9
Tmin = 0.976, Tmax = 0.988	k = −10→10
6503 measured reflections	l = −11→11

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.085P)^2 + 0.0695P] where P = (Fo^2 + 2Fc^2)/3
2097 reflections	(Δ/σ)max < 0.001
148 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.2028 (2)	1.0701 (2)	−0.00206 (19)	0.0528 (5)
O2	0.1524 (2)	1.07407 (18)	−0.11426 (17)	0.0637 (5)
O1	0.1824 (3)	1.1983 (2)	0.0307 (2)	0.0957 (7)
C2	0.2750 (2)	0.7507 (2)	0.08584 (18)	0.0391 (4)
H2	0.2107	0.7551	0.0129	0.047*
C3	0.3558 (2)	0.5920 (2)	0.18285 (18)	0.0382 (4)
C1	0.2920 (2)	0.9027 (2)	0.09979 (19)	0.0407 (4)
C4	0.4542 (3)	0.5915 (3)	0.2875 (2)	0.0483 (5)
H4	0.5103	0.4856	0.3519	0.058*
C6	0.3873 (3)	0.9029 (3)	0.2038 (2)	0.0504 (5)
H6	0.3958	1.0069	0.2109	0.060*
C5	0.4703 (3)	0.7449 (3)	0.2977 (2)	0.0557 (5)
H5	0.5374	0.7417	0.3683	0.067*
C8	0.2728 (2)	0.2961 (2)	0.32899 (19)	0.0404 (4)
C7	0.3362 (3)	0.4217 (2)	0.17492 (19)	0.0473 (5)
H7A	0.2516	0.4460	0.1051	0.057*
H7B	0.4505	0.3681	0.1357	0.057*
N2	0.3767 (2)	0.16518 (18)	0.41274 (17)	0.0453 (4)
O3	0.55854 (18)	0.15786 (19)	0.34362 (18)	0.0665 (5)
H3	0.6176	0.0640	0.3900	0.100*
N3	0.0994 (2)	0.3282 (2)	0.38795 (19)	0.0583 (5)
C10	0.0425 (4)	0.2126 (4)	0.5410 (3)	0.0842 (8)
H10A	0.0344	0.1025	0.5387	0.126*
H10B	−0.0722	0.2645	0.5782	0.126*
H10C	0.1280	0.1947	0.6070	0.126*
C9	−0.0412 (3)	0.4295 (4)	0.2971 (3)	0.0848 (8)
H9A	0.0017	0.5260	0.2141	0.127*
H9B	−0.1400	0.4726	0.3584	0.127*
H9C	−0.0796	0.3576	0.2579	0.127*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0528 (10)	0.0383 (9)	0.0583 (10)	−0.0045 (7)	−0.0095 (8)	−0.0092 (8)
O2	0.0677 (10)	0.0513 (9)	0.0571 (9)	−0.0024 (7)	−0.0219 (7)	−0.0022 (7)
O1	0.1332 (18)	0.0386 (9)	0.1205 (15)	0.0089 (9)	−0.0488 (13)	−0.0320 (9)
C2	0.0387 (10)	0.0398 (10)	0.0346 (8)	−0.0017 (7)	−0.0061 (7)	−0.0116 (7)
C3	0.0347 (9)	0.0367 (9)	0.0356 (8)	−0.0014 (7)	−0.0007 (7)	−0.0102 (7)
C1	0.0390 (10)	0.0351 (9)	0.0401 (9)	−0.0046 (7)	−0.0014 (7)	−0.0084 (7)
C4	0.0432 (10)	0.0466 (11)	0.0431 (10)	−0.0056 (8)	−0.0117 (8)	−0.0022 (8)
C6	0.0540 (12)	0.0489 (11)	0.0503 (11)	−0.0186 (9)	−0.0032 (9)	−0.0166 (9)
C5	0.0571 (13)	0.0636 (13)	0.0488 (11)	−0.0222 (10)	−0.0172 (9)	−0.0111 (9)
C8	0.0478 (11)	0.0308 (9)	0.0410 (9)	0.0010 (7)	−0.0087 (8)	−0.0144 (7)
C7	0.0591 (12)	0.0357 (10)	0.0402 (9)	0.0032 (8)	−0.0065 (8)	−0.0131 (8)
N2	0.0419 (9)	0.0355 (8)	0.0483 (9)	0.0013 (6)	−0.0071 (7)	−0.0085 (6)
O3	0.0435 (8)	0.0507 (9)	0.0762 (10)	0.0071 (6)	−0.0023 (7)	−0.0045 (7)
N3	0.0421 (10)	0.0573 (10)	0.0576 (10)	0.0055 (8)	−0.0053 (7)	−0.0110 (8)
C10	0.0610 (15)	0.0939 (19)	0.0661 (14)	−0.0061 (13)	0.0136 (12)	−0.0117 (13)
C9	0.0521 (14)	0.0740 (16)	0.108 (2)	0.0076 (12)	−0.0260 (14)	−0.0152 (14)

Geometric parameters (Å, º)

N1—O2	1.213 (2)	C8—N3	1.357 (2)
N1—O1	1.214 (2)	C8—C7	1.509 (2)
N1—C1	1.472 (2)	C7—H7A	0.9700
C2—C3	1.386 (2)	C7—H7B	0.9700
C2—C1	1.387 (2)	N2—O3	1.429 (2)
C2—H2	0.9300	O3—H3	0.8200
C3—C4	1.387 (3)	N3—C9	1.434 (3)
C3—C7	1.521 (2)	N3—C10	1.458 (3)
C1—C6	1.368 (3)	C10—H10A	0.9600
C4—C5	1.379 (3)	C10—H10B	0.9600
C4—H4	0.9300	C10—H10C	0.9600
C6—C5	1.378 (3)	C9—H9A	0.9600
C6—H6	0.9300	C9—H9B	0.9600
C5—H5	0.9300	C9—H9C	0.9600
C8—N2	1.292 (2)
O2—N1—O1	122.95 (17)	C8—C7—C3	111.66 (14)
O2—N1—C1	118.80 (15)	C8—C7—H7A	109.3
O1—N1—C1	118.24 (18)	C3—C7—H7A	109.3
C3—C2—C1	118.62 (16)	C8—C7—H7B	109.3
C3—C2—H2	120.7	C3—C7—H7B	109.3
C1—C2—H2	120.7	H7A—C7—H7B	107.9
C4—C3—C2	118.85 (16)	C8—N2—O3	111.70 (14)
C4—C3—C7	120.66 (15)	N2—O3—H3	109.5
C2—C3—C7	120.50 (16)	C8—N3—C9	123.55 (18)
C6—C1—C2	122.78 (17)	C8—N3—C10	117.97 (17)
C6—C1—N1	119.16 (16)	C9—N3—C10	115.5 (2)
C2—C1—N1	118.06 (16)	N3—C10—H10A	109.5
C5—C4—C3	121.24 (17)	N3—C10—H10B	109.5
C5—C4—H4	119.4	H10A—C10—H10B	109.5
C3—C4—H4	119.4	N3—C10—H10C	109.5
C1—C6—C5	118.26 (18)	H10A—C10—H10C	109.5
C1—C6—H6	120.9	H10B—C10—H10C	109.5
C5—C6—H6	120.9	N3—C9—H9A	109.5
C6—C5—C4	120.23 (18)	N3—C9—H9B	109.5
C6—C5—H5	119.9	H9A—C9—H9B	109.5
C4—C5—H5	119.9	N3—C9—H9C	109.5
N2—C8—N3	117.67 (16)	H9A—C9—H9C	109.5
N2—C8—C7	123.72 (16)	H9B—C9—H9C	109.5
N3—C8—C7	118.47 (15)
C1—C2—C3—C4	−1.6 (2)	C1—C6—C5—C4	−1.0 (3)
C1—C2—C3—C7	178.20 (15)	C3—C4—C5—C6	0.4 (3)
C3—C2—C1—C6	0.9 (3)	N2—C8—C7—C3	−101.67 (19)
C3—C2—C1—N1	−178.90 (14)	N3—C8—C7—C3	73.9 (2)
O2—N1—C1—C6	164.10 (17)	C4—C3—C7—C8	51.8 (2)
O1—N1—C1—C6	−16.2 (3)	C2—C3—C7—C8	−128.00 (17)
O2—N1—C1—C2	−16.1 (3)	N3—C8—N2—O3	−173.71 (15)
O1—N1—C1—C2	163.65 (19)	C7—C8—N2—O3	1.9 (2)
C2—C3—C4—C5	1.0 (3)	N2—C8—N3—C9	−159.9 (2)
C7—C3—C4—C5	−178.82 (17)	C7—C8—N3—C9	24.3 (3)
C2—C1—C6—C5	0.4 (3)	N2—C8—N3—C10	−0.2 (3)
N1—C1—C6—C5	−179.78 (16)	C7—C8—N3—C10	−176.0 (2)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2^i	0.82	2.11	2.8292 (19)	146
C10—H10C···O2^ii	0.96	2.51	3.288 (3)	139
C10—H10B···Cg1	0.96	2.85	3.718 (3)	151

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