2′-(2-Hydr­oxy-3,5-diiodo­benzyl­idene)isonicotinohydrazide methanol solvate

In the title compound, C₁₃H₉I₂N₃O₂·CH₃OH, the Schiff base mol­ecule displays a trans configuration with respect to the C=N double bond. The dihedral angle between the benzene and pyridine rings is 24.6 (2)°. The crystal structure is stabilized by inter­molecular N—H...O, O—H...N and C—H...O hydrogen bonds, forming a network.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.038
• wR factor = 0.093
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.93
PLAT431_ALERT_2_C Short Inter HL..A Contact  I2     ..  O2      ..       3.36 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C13 H9 I2 N3 O2

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.926
            Tmax scaled      0.517 Tmin scaled      0.450

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 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: SAINT (Bruker, 1998); 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'-(2-Hydroxy-3,5-diiodobenzylidene)isonicotinohydrazide methanol solvate

Crystal data

C14H13I2N3O3	Z = 2
Mr = 525.07	F(000) = 496
Triclinic, P1	Dx = 2.027 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.977 (2) Å	Cell parameters from 1625 reflections
b = 9.114 (3) Å	θ = 2.3–24.9°
c = 11.387 (3) Å	µ = 3.67 mm^−1
α = 92.099 (2)°	T = 298 K
β = 111.455 (3)°	Block, yellow
γ = 95.638 (2)°	0.23 × 0.20 × 0.18 mm
V = 860.2 (4) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3490 independent reflections
Radiation source: fine-focus sealed tube	2579 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
ω scans	θmax = 26.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→9
Tmin = 0.486, Tmax = 0.558	k = −11→11
4887 measured reflections	l = −14→12

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0347P)^2 + 1.1556P] where P = (Fo^2 + 2Fc^2)/3
3490 reflections	(Δ/σ)max = 0.001
200 parameters	Δρmax = 0.96 e Å^−3
0 restraints	Δρmin = −1.09 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	−0.2213 (4)	0.2537 (4)	−0.2056 (3)	0.0568 (10)
H1	−0.2064	0.2021	−0.1458	0.085*
O2	−0.3059 (5)	−0.0410 (4)	−0.0088 (3)	0.0578 (10)
I1	−0.27691 (5)	0.41098 (5)	−0.45434 (4)	0.07798 (18)
I2	0.39320 (5)	0.68245 (4)	−0.13432 (4)	0.06503 (15)
N1	−0.0710 (5)	0.1723 (4)	0.0149 (4)	0.0431 (9)
N2	−0.0717 (5)	0.0936 (5)	0.1152 (4)	0.0452 (10)
H2	0.0061	0.1085	0.1877	0.054*
N3	−0.2324 (6)	−0.1983 (5)	0.4236 (4)	0.0594 (12)
C1	0.0488 (6)	0.3567 (5)	−0.0728 (4)	0.0381 (10)
C2	−0.0863 (6)	0.3457 (5)	−0.1864 (4)	0.0430 (11)
C3	−0.0808 (6)	0.4318 (5)	−0.2837 (4)	0.0428 (11)
C4	0.0561 (6)	0.5255 (5)	−0.2698 (5)	0.0468 (12)
H4	0.0591	0.5814	−0.3357	0.056*
C5	0.1890 (6)	0.5362 (5)	−0.1577 (5)	0.0432 (11)
C6	0.1841 (6)	0.4528 (5)	−0.0599 (5)	0.0427 (11)
H6	0.2731	0.4614	0.0157	0.051*
C7	0.0488 (6)	0.2691 (5)	0.0308 (4)	0.0421 (11)
H7	0.1351	0.2834	0.1081	0.050*
C8	−0.2012 (6)	−0.0092 (6)	0.0947 (4)	0.0430 (11)
C9	−0.2059 (6)	−0.0779 (5)	0.2113 (4)	0.0432 (11)
C10	−0.3549 (7)	−0.1196 (7)	0.2161 (5)	0.0581 (15)
H10	−0.4485	−0.1088	0.1477	0.070*
C11	−0.3634 (8)	−0.1774 (7)	0.3237 (6)	0.0664 (17)
H11	−0.4644	−0.2032	0.3272	0.080*
C12	−0.0915 (7)	−0.1618 (6)	0.4150 (5)	0.0535 (13)
H12	0.0005	−0.1775	0.4829	0.064*
C13	−0.0720 (7)	−0.1016 (6)	0.3115 (5)	0.0481 (12)
H13	0.0304	−0.0776	0.3101	0.058*
O3	0.2132 (5)	0.1820 (5)	0.3264 (4)	0.0642 (11)
H3	0.2288	0.2174	0.3978	0.10 (3)*
C14	0.3470 (9)	0.1146 (9)	0.3283 (7)	0.087 (2)
H14A	0.3253	0.0666	0.2463	0.130*
H14B	0.3687	0.0428	0.3901	0.130*
H14C	0.4389	0.1882	0.3497	0.130*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.042 (2)	0.066 (2)	0.050 (2)	−0.0141 (17)	0.0071 (16)	0.0164 (18)
O2	0.052 (2)	0.075 (3)	0.0382 (19)	−0.0109 (19)	0.0111 (17)	0.0078 (18)
I1	0.0654 (3)	0.0871 (3)	0.0529 (2)	−0.0132 (2)	−0.00758 (19)	0.0242 (2)
I2	0.0404 (2)	0.0661 (3)	0.0866 (3)	−0.00550 (17)	0.02275 (19)	0.0211 (2)
N1	0.043 (2)	0.049 (2)	0.040 (2)	0.0054 (19)	0.0175 (18)	0.0110 (18)
N2	0.041 (2)	0.058 (3)	0.035 (2)	−0.0012 (19)	0.0126 (17)	0.0135 (19)
N3	0.071 (4)	0.063 (3)	0.047 (3)	0.003 (3)	0.026 (2)	0.014 (2)
C1	0.037 (3)	0.042 (3)	0.034 (2)	0.002 (2)	0.013 (2)	0.002 (2)
C2	0.040 (3)	0.046 (3)	0.041 (3)	−0.003 (2)	0.015 (2)	0.003 (2)
C3	0.039 (3)	0.045 (3)	0.037 (3)	0.001 (2)	0.005 (2)	0.007 (2)
C4	0.051 (3)	0.050 (3)	0.041 (3)	0.004 (2)	0.018 (2)	0.012 (2)
C5	0.039 (3)	0.043 (3)	0.050 (3)	0.002 (2)	0.020 (2)	0.004 (2)
C6	0.034 (3)	0.047 (3)	0.044 (3)	0.001 (2)	0.010 (2)	0.003 (2)
C7	0.036 (3)	0.053 (3)	0.037 (2)	0.006 (2)	0.012 (2)	0.005 (2)
C8	0.041 (3)	0.052 (3)	0.037 (3)	0.001 (2)	0.016 (2)	0.007 (2)
C9	0.048 (3)	0.044 (3)	0.036 (2)	−0.004 (2)	0.017 (2)	0.003 (2)
C10	0.047 (3)	0.077 (4)	0.044 (3)	−0.009 (3)	0.013 (2)	0.010 (3)
C11	0.054 (4)	0.088 (4)	0.058 (4)	−0.012 (3)	0.026 (3)	0.014 (3)
C12	0.059 (4)	0.057 (3)	0.043 (3)	0.007 (3)	0.015 (3)	0.013 (2)
C13	0.049 (3)	0.051 (3)	0.046 (3)	0.004 (2)	0.020 (2)	0.012 (2)
O3	0.064 (3)	0.083 (3)	0.036 (2)	−0.003 (2)	0.0119 (18)	0.004 (2)
C14	0.061 (4)	0.124 (6)	0.069 (4)	−0.009 (4)	0.023 (4)	−0.008 (4)

Geometric parameters (Å, º)

O1—C2	1.347 (6)	C5—C6	1.383 (7)
O1—H1	0.82	C6—H6	0.93
O2—C8	1.211 (6)	C7—H7	0.93
I1—C3	2.078 (5)	C8—C9	1.501 (6)
I2—C5	2.084 (5)	C9—C13	1.364 (7)
N1—C7	1.275 (6)	C9—C10	1.375 (7)
N1—N2	1.372 (5)	C10—C11	1.376 (7)
N2—C8	1.362 (6)	C10—H10	0.93
N2—H2	0.86	C11—H11	0.93
N3—C12	1.315 (7)	C12—C13	1.379 (7)
N3—C11	1.340 (7)	C12—H12	0.93
C1—C6	1.384 (6)	C13—H13	0.93
C1—C2	1.405 (6)	O3—C14	1.396 (8)
C1—C7	1.448 (6)	O3—H3	0.82
C2—C3	1.392 (7)	C14—H14A	0.96
C3—C4	1.381 (7)	C14—H14B	0.96
C4—C5	1.384 (7)	C14—H14C	0.96
C4—H4	0.93
C2—O1—H1	109.5	C1—C7—H7	120.4
C7—N1—N2	118.6 (4)	O2—C8—N2	122.8 (4)
C8—N2—N1	117.0 (4)	O2—C8—C9	122.6 (5)
C8—N2—H2	121.5	N2—C8—C9	114.6 (4)
N1—N2—H2	121.5	C13—C9—C10	118.6 (5)
C12—N3—C11	117.0 (5)	C13—C9—C8	123.9 (5)
C6—C1—C2	119.3 (4)	C10—C9—C8	117.5 (5)
C6—C1—C7	119.5 (4)	C9—C10—C11	119.0 (5)
C2—C1—C7	121.2 (4)	C9—C10—H10	120.5
O1—C2—C3	118.4 (4)	C11—C10—H10	120.5
O1—C2—C1	122.4 (4)	N3—C11—C10	122.8 (6)
C3—C2—C1	119.2 (4)	N3—C11—H11	118.6
C4—C3—C2	120.7 (4)	C10—C11—H11	118.6
C4—C3—I1	119.8 (3)	N3—C12—C13	124.0 (5)
C2—C3—I1	119.5 (4)	N3—C12—H12	118.0
C3—C4—C5	120.1 (4)	C13—C12—H12	118.0
C3—C4—H4	120.0	C9—C13—C12	118.6 (5)
C5—C4—H4	120.0	C9—C13—H13	120.7
C6—C5—C4	119.8 (5)	C12—C13—H13	120.7
C6—C5—I2	120.1 (4)	C14—O3—H3	109.5
C4—C5—I2	120.2 (4)	O3—C14—H14A	109.5
C5—C6—C1	121.0 (4)	O3—C14—H14B	109.5
C5—C6—H6	119.5	H14A—C14—H14B	109.5
C1—C6—H6	119.5	O3—C14—H14C	109.5
N1—C7—C1	119.3 (4)	H14A—C14—H14C	109.5
N1—C7—H7	120.4	H14B—C14—H14C	109.5
C7—N1—N2—C8	−179.8 (4)	N2—N1—C7—C1	−177.9 (4)
C6—C1—C2—O1	179.5 (5)	C6—C1—C7—N1	−174.5 (4)
C7—C1—C2—O1	−0.4 (8)	C2—C1—C7—N1	5.5 (7)
C6—C1—C2—C3	0.1 (7)	N1—N2—C8—O2	6.2 (7)
C7—C1—C2—C3	−179.9 (5)	N1—N2—C8—C9	−172.5 (4)
O1—C2—C3—C4	−178.6 (5)	O2—C8—C9—C13	148.8 (5)
C1—C2—C3—C4	0.9 (8)	N2—C8—C9—C13	−32.4 (7)
O1—C2—C3—I1	−1.6 (7)	O2—C8—C9—C10	−30.9 (8)
C1—C2—C3—I1	177.9 (4)	N2—C8—C9—C10	147.9 (5)
C2—C3—C4—C5	−0.9 (8)	C13—C9—C10—C11	2.8 (8)
I1—C3—C4—C5	−177.9 (4)	C8—C9—C10—C11	−177.5 (5)
C3—C4—C5—C6	0.0 (8)	C12—N3—C11—C10	−0.5 (9)
C3—C4—C5—I2	−178.1 (4)	C9—C10—C11—N3	−1.6 (10)
C4—C5—C6—C1	0.9 (8)	C11—N3—C12—C13	1.3 (9)
I2—C5—C6—C1	179.0 (4)	C10—C9—C13—C12	−2.1 (8)
C2—C1—C6—C5	−1.0 (7)	C8—C9—C13—C12	178.2 (5)
C7—C1—C6—C5	179.0 (5)	N3—C12—C13—C9	0.0 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.84	2.555 (5)	146
N2—H2···O3	0.86	1.98	2.814 (6)	163
O3—H3···N3^i	0.82	2.04	2.786 (6)	152
C7—H7···O3	0.93	2.56	3.305 (5)	138

Symmetry code: (i) −x, −y, −z+1.