2,3-Dihydro-1H-indole-2,3-dione 3-isonicotinoylhydrazone

In the title compound, C₁₄H₁₀N₄O₂, the pyridine ring and the isatin unit (indoline-2,3-dione) are nearly coplanar, the dihedral angle being 3.79 (11)°. Inter- and intra­molecular N—H...O hydrogen bonding and weak inter­molecular C—H...O hydrogen bonding occur in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.026
• wR factor = 0.073
• Data-to-parameter ratio = 6.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.54
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.03
           From the CIF: _reflns_number_total               1191
           Count of symmetry unique reflns         1192
           Completeness (_total/calc)             99.92%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; 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.

2,3-dihydro-1H-indole-2,3-dione 3-isonicotinoylhydrazone

Crystal data

C14H10N4O2	F(000) = 552
Mr = 266.26	Dx = 1.469 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2489 reflections
a = 8.007 (5) Å	θ = 2.6–24.1°
b = 28.561 (16) Å	µ = 0.10 mm^−1
c = 5.266 (3) Å	T = 293 K
V = 1204.2 (12) Å^3	Block, red
Z = 4	0.28 × 0.22 × 0.18 mm

Data collection

Bruker APEX-II CCD area-detector diffractometer	1109 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 25.0°, θmin = 2.6°
φ and ω scans	h = −9→9
6229 measured reflections	k = −31→34
1191 independent reflections	l = −6→6

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.026	H-atom parameters constrained
wR(F^2) = 0.073	w = 1/[σ^2(Fo^2) + (0.0461P)^2 + 0.107P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
1191 reflections	Δρmax = 0.13 e Å^−3
182 parameters	Δρmin = −0.09 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (2)

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	0.09952 (18)	0.71433 (5)	0.8958 (3)	0.0507 (4)
O2	0.4092 (2)	0.64382 (4)	0.1771 (4)	0.0550 (4)
N1	0.1096 (2)	0.79515 (5)	0.8724 (4)	0.0427 (4)
H1	0.0489	0.8020	1.0019	0.051*
N2	0.31698 (18)	0.72244 (5)	0.4284 (4)	0.0393 (4)
N3	0.28090 (19)	0.67819 (5)	0.5118 (4)	0.0418 (4)
H3A	0.2260	0.6742	0.6504	0.050*
N4	0.2107 (3)	0.50460 (8)	0.6674 (6)	0.0804 (8)
C1	0.1841 (2)	0.82829 (6)	0.7106 (4)	0.0372 (4)
C2	0.1757 (2)	0.87659 (7)	0.7222 (5)	0.0450 (5)
H2	0.1171	0.8918	0.8506	0.054*
C3	0.2583 (3)	0.90144 (7)	0.5343 (5)	0.0492 (5)
H3	0.2541	0.9340	0.5371	0.059*
C4	0.3470 (2)	0.87936 (7)	0.3421 (5)	0.0464 (5)
H4	0.4005	0.8971	0.2185	0.056*
C5	0.3561 (2)	0.83088 (7)	0.3336 (5)	0.0427 (5)
H5	0.4163	0.8158	0.2067	0.051*
C6	0.2734 (2)	0.80567 (6)	0.5187 (4)	0.0369 (4)
C7	0.2543 (2)	0.75563 (6)	0.5642 (4)	0.0357 (4)
C8	0.1462 (2)	0.75102 (7)	0.7974 (4)	0.0393 (5)
C9	0.3320 (2)	0.64080 (6)	0.3753 (5)	0.0400 (5)
C10	0.2873 (2)	0.59395 (7)	0.4868 (5)	0.0430 (5)
C11	0.3539 (3)	0.55484 (7)	0.3737 (6)	0.0618 (7)
H11	0.4247	0.5575	0.2345	0.074*
C12	0.3130 (4)	0.51130 (9)	0.4716 (8)	0.0801 (10)
H12	0.3602	0.4850	0.3956	0.096*
C13	0.1492 (3)	0.54249 (9)	0.7726 (7)	0.0722 (8)
H13	0.0777	0.5388	0.9104	0.087*
C14	0.1833 (3)	0.58745 (8)	0.6925 (6)	0.0581 (6)
H14	0.1368	0.6130	0.7760	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0632 (9)	0.0392 (7)	0.0496 (10)	−0.0031 (6)	0.0122 (9)	0.0040 (7)
O2	0.0710 (10)	0.0379 (7)	0.0561 (10)	−0.0011 (7)	0.0190 (9)	−0.0009 (8)
N1	0.0524 (9)	0.0384 (9)	0.0372 (10)	0.0022 (7)	0.0061 (9)	−0.0016 (8)
N2	0.0433 (8)	0.0305 (8)	0.0442 (10)	−0.0020 (6)	0.0017 (8)	0.0003 (8)
N3	0.0499 (8)	0.0293 (8)	0.0462 (10)	−0.0032 (7)	0.0080 (9)	0.0014 (8)
N4	0.1065 (17)	0.0448 (13)	0.090 (2)	−0.0185 (12)	−0.0195 (18)	0.0182 (15)
C1	0.0410 (9)	0.0352 (10)	0.0355 (11)	−0.0004 (8)	−0.0038 (9)	−0.0007 (9)
C2	0.0521 (11)	0.0364 (10)	0.0464 (13)	0.0049 (8)	−0.0019 (11)	−0.0047 (10)
C3	0.0596 (12)	0.0330 (10)	0.0549 (14)	−0.0007 (9)	−0.0036 (13)	0.0009 (12)
C4	0.0552 (11)	0.0374 (11)	0.0466 (13)	−0.0063 (9)	−0.0012 (11)	0.0045 (10)
C5	0.0451 (10)	0.0409 (10)	0.0421 (12)	−0.0010 (8)	0.0008 (10)	−0.0001 (10)
C6	0.0391 (9)	0.0334 (9)	0.0381 (11)	0.0004 (7)	−0.0036 (9)	−0.0015 (10)
C7	0.0373 (9)	0.0315 (9)	0.0385 (12)	0.0003 (8)	−0.0020 (9)	−0.0006 (10)
C8	0.0428 (10)	0.0345 (10)	0.0407 (12)	−0.0002 (8)	−0.0009 (9)	0.0013 (9)
C9	0.0401 (10)	0.0332 (10)	0.0467 (14)	−0.0010 (7)	0.0010 (11)	−0.0001 (9)
C10	0.0455 (10)	0.0324 (10)	0.0512 (14)	−0.0039 (8)	−0.0097 (10)	0.0020 (9)
C11	0.0810 (15)	0.0344 (11)	0.0700 (18)	−0.0012 (10)	−0.0017 (15)	−0.0023 (13)
C12	0.111 (2)	0.0357 (13)	0.094 (3)	0.0009 (13)	−0.017 (2)	−0.0026 (16)
C13	0.0869 (18)	0.0524 (15)	0.077 (2)	−0.0171 (12)	−0.0023 (16)	0.0207 (15)
C14	0.0632 (13)	0.0459 (12)	0.0652 (16)	−0.0066 (10)	0.0019 (13)	0.0084 (14)

Geometric parameters (Å, º)

O1—C8	1.227 (2)	C3—H3	0.9300
O2—C9	1.216 (3)	C4—C5	1.387 (3)
N1—C8	1.353 (3)	C4—H4	0.9300
N1—C1	1.406 (3)	C5—C6	1.381 (3)
N1—H1	0.8600	C5—H5	0.9300
N2—C7	1.289 (3)	C6—C7	1.457 (3)
N2—N3	1.369 (2)	C7—C8	1.508 (3)
N3—C9	1.351 (3)	C9—C10	1.504 (3)
N3—H3A	0.8600	C10—C11	1.374 (3)
N4—C13	1.312 (4)	C10—C14	1.379 (4)
N4—C12	1.331 (4)	C11—C12	1.385 (4)
C1—C2	1.382 (3)	C11—H11	0.9300
C1—C6	1.396 (3)	C12—H12	0.9300
C2—C3	1.385 (3)	C13—C14	1.379 (3)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.388 (3)	C14—H14	0.9300
C8—N1—C1	111.01 (17)	C1—C6—C7	106.32 (17)
C8—N1—H1	124.5	N2—C7—C6	126.09 (19)
C1—N1—H1	124.5	N2—C7—C8	127.65 (17)
C7—N2—N3	114.76 (18)	C6—C7—C8	106.25 (16)
C9—N3—N2	119.70 (18)	O1—C8—N1	127.4 (2)
C9—N3—H3A	120.2	O1—C8—C7	126.36 (18)
N2—N3—H3A	120.2	N1—C8—C7	106.28 (17)
C13—N4—C12	116.1 (2)	O2—C9—N3	123.68 (19)
C2—C1—C6	121.25 (19)	O2—C9—C10	121.25 (19)
C2—C1—N1	128.6 (2)	N3—C9—C10	115.1 (2)
C6—C1—N1	110.13 (16)	C11—C10—C14	117.7 (2)
C1—C2—C3	117.1 (2)	C11—C10—C9	117.5 (2)
C1—C2—H2	121.4	C14—C10—C9	124.7 (2)
C3—C2—H2	121.4	C10—C11—C12	118.5 (3)
C2—C3—C4	122.16 (19)	C10—C11—H11	120.8
C2—C3—H3	118.9	C12—C11—H11	120.8
C4—C3—H3	118.9	N4—C12—C11	124.3 (3)
C5—C4—C3	120.3 (2)	N4—C12—H12	117.9
C5—C4—H4	119.9	C11—C12—H12	117.9
C3—C4—H4	119.9	N4—C13—C14	124.4 (3)
C6—C5—C4	118.20 (19)	N4—C13—H13	117.8
C6—C5—H5	120.9	C14—C13—H13	117.8
C4—C5—H5	120.9	C10—C14—C13	119.0 (3)
C5—C6—C1	120.99 (17)	C10—C14—H14	120.5
C5—C6—C7	132.68 (18)	C13—C14—H14	120.5
C7—N2—N3—C9	176.10 (17)	C1—N1—C8—O1	−179.25 (19)
C8—N1—C1—C2	179.53 (19)	C1—N1—C8—C7	−0.2 (2)
C8—N1—C1—C6	0.3 (2)	N2—C7—C8—O1	−0.3 (3)
C6—C1—C2—C3	0.6 (3)	C6—C7—C8—O1	179.06 (19)
N1—C1—C2—C3	−178.6 (2)	N2—C7—C8—N1	−179.40 (19)
C1—C2—C3—C4	−0.3 (3)	C6—C7—C8—N1	0.0 (2)
C2—C3—C4—C5	−0.3 (3)	N2—N3—C9—O2	−0.4 (3)
C3—C4—C5—C6	0.7 (3)	N2—N3—C9—C10	179.22 (16)
C4—C5—C6—C1	−0.5 (3)	O2—C9—C10—C11	7.6 (3)
C4—C5—C6—C7	178.78 (19)	N3—C9—C10—C11	−172.0 (2)
C2—C1—C6—C5	−0.1 (3)	O2—C9—C10—C14	−171.7 (2)
N1—C1—C6—C5	179.15 (18)	N3—C9—C10—C14	8.7 (3)
C2—C1—C6—C7	−179.59 (18)	C14—C10—C11—C12	0.0 (4)
N1—C1—C6—C7	−0.3 (2)	C9—C10—C11—C12	−179.3 (2)
N3—N2—C7—C6	179.88 (17)	C13—N4—C12—C11	−1.2 (5)
N3—N2—C7—C8	−0.9 (3)	C10—C11—C12—N4	1.1 (4)
C5—C6—C7—N2	0.2 (4)	C12—N4—C13—C14	0.3 (4)
C1—C6—C7—N2	179.61 (19)	C11—C10—C14—C13	−0.9 (3)
C5—C6—C7—C8	−179.2 (2)	C9—C10—C14—C13	178.5 (2)
C1—C6—C7—C8	0.2 (2)	N4—C13—C14—C10	0.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.86	2.12	2.861 (3)	144
N3—H3A···O1	0.86	2.00	2.695 (3)	137
C5—H5···O1^ii	0.93	2.36	3.283 (3)	172

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