Crystal structure of bis­{N′-[(E)-4-hy­droxy­benzyl­idene]pyridine-4-carbohydrazide-κN¹}di­iodidocadmium methanol disolvate

In the title structure, the Cd^II atom is located on a twofold rotation axis and is coordinated by two I atoms and two N atoms of two carboxyl­ate groups of two planar N′-[(E)-4-hy­droxy­benzyl­idene]pyridine-4-carbohydrazide ligands. N—H...O, O—H...O, C—H...O and C—H...I hydrogen bonding assembles the mol­ecules into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 213 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.040
• wR factor = 0.094
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full value Low .      0.943 Note

Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        Cd1 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1     ..  I1      ..       3.11 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.841 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600        164 Report
PLAT971_ALERT_2_C Check Calcd Residual Density  1.00A From     Cd1       1.55 eA-3

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT432_ALERT_2_G Short Inter X...Y Contact  C13    ..  C13     ..       3.14 Ang.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note
PLAT881_ALERT_1_G Missing datum for _diffrn_reflns_av_R_equivalents    Please Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         34 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Note

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: EXPOSE (Stoe & Cie, 2000); cell refinement: CELL (Stoe & Cie, 2000); data reduction: SELECT (Stoe & Cie, 2000) and INTEGRATE (Stoe & Cie, 2000); program(s) used to solve structure: SHELXT-2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and WinGX (Farrugia, 2012).

Bis{N'-[(E)-4-hydroxybenzylidene]pyridine-4-carbohydrazide-κN¹}diiodidocadmium methanol disolvate

Crystal data

[CdI2(C13H11N3O2)2]·2CH4O	F(000) = 1768
Mr = 912.79	Dx = 1.873 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 428 reflections
a = 8.0245 (4) Å	θ = 2.9–27.6°
b = 13.2482 (9) Å	µ = 2.63 mm^−1
c = 30.4540 (19) Å	T = 213 K
V = 3237.6 (3) Å^3	Prism, colorless
Z = 4	0.5 × 0.3 × 0.3 mm

Data collection

Stoe IPDS1 diffractometer	3511 independent reflections
Radiation source: fine-focus sealed tube	2542 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
phi scan	θmax = 27.6°, θmin = 2.9°
Absorption correction: numerical Stoe XRED32 (Stoe & Cie, 2000)	h = 0→9
Tmin = 0.337, Tmax = 0.453	k = 0→17
3511 measured reflections	l = 0→39

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.0655P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.094	(Δ/σ)max < 0.001
S = 0.88	Δρmax = 1.68 e Å^−3
3511 reflections	Δρmin = −1.47 e Å^−3
206 parameters	Extinction correction: SHELXL-2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001XFc^2λ^3/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0026 (2)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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
I1	−0.24029 (5)	0.11226 (3)	0.20424 (2)	0.0555 (1)
Cd1	0.00000	0.20717 (2)	0.25000	0.0250 (1)
O1	0.3473 (4)	0.62436 (18)	0.12617 (10)	0.0359 (9)
O2	1.0000 (4)	0.70774 (18)	−0.10066 (9)	0.0310 (8)
N1	0.1497 (5)	0.3244 (2)	0.21085 (10)	0.0284 (10)
N2	0.5039 (5)	0.4973 (2)	0.09734 (10)	0.0263 (9)
N3	0.5712 (5)	0.5598 (2)	0.06532 (10)	0.0269 (10)
C1	0.0746 (6)	0.4087 (3)	0.19639 (12)	0.0295 (11)
C2	0.1550 (5)	0.4791 (3)	0.17078 (12)	0.0280 (11)
C3	0.3166 (5)	0.4612 (2)	0.15733 (12)	0.0247 (10)
O3	0.6488 (4)	0.3011 (2)	0.09399 (12)	0.0431 (11)
C4	0.3962 (6)	0.3747 (3)	0.17287 (13)	0.0302 (11)
C5	0.3096 (6)	0.3093 (3)	0.19927 (13)	0.0319 (13)
C6	0.3943 (5)	0.5354 (2)	0.12611 (12)	0.0262 (10)
C7	0.6539 (5)	0.5138 (3)	0.03593 (12)	0.0265 (10)
C8	0.7372 (5)	0.5675 (3)	−0.00022 (11)	0.0244 (10)
C9	0.7230 (5)	0.6713 (3)	−0.00636 (13)	0.0290 (13)
C10	0.8101 (6)	0.7194 (3)	−0.03945 (13)	0.0293 (13)
C11	0.9119 (5)	0.6642 (2)	−0.06770 (11)	0.0230 (10)
C12	0.9264 (6)	0.5601 (3)	−0.06211 (12)	0.0263 (10)
C13	0.8388 (5)	0.5132 (3)	−0.02870 (12)	0.0268 (13)
C14	0.5662 (7)	0.2065 (3)	0.09320 (17)	0.0450 (16)
H1	−0.03730	0.42000	0.20410	0.0350*
H2	0.10030	0.53890	0.16250	0.0340*
H2N	0.541 (6)	0.444 (4)	0.0984 (14)	0.0320*
H2O	0.967 (7)	0.765 (2)	−0.1033 (17)	0.0460*
H4	0.50760	0.36150	0.16530	0.0360*
H5	0.36440	0.25140	0.20980	0.0380*
H7	0.66220	0.44310	0.03730	0.0320*
H9	0.65340	0.70910	0.01220	0.0350*
H10	0.80070	0.78960	−0.04290	0.0350*
H12	0.99500	0.52210	−0.08090	0.0320*
H13	0.84820	0.44290	−0.02520	0.0320*
H3O	0.748 (3)	0.294 (5)	0.095 (2)	0.0650*
H14A	0.62690	0.15860	0.11120	0.0670*
H14B	0.56100	0.18190	0.06320	0.0670*
H14C	0.45410	0.21430	0.10460	0.0670*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0416 (3)	0.0625 (2)	0.0624 (2)	−0.0191 (2)	0.0021 (2)	−0.0255 (2)
Cd1	0.0250 (2)	0.0179 (2)	0.0320 (2)	0.0000	0.0051 (2)	0.0000
O1	0.041 (2)	0.0198 (12)	0.0469 (16)	0.0042 (12)	0.0127 (14)	0.0091 (11)
O2	0.0326 (17)	0.0217 (11)	0.0386 (13)	0.0017 (13)	0.0098 (13)	0.0098 (10)
N1	0.035 (2)	0.0209 (13)	0.0292 (16)	0.0023 (13)	0.0071 (14)	0.0038 (12)
N2	0.031 (2)	0.0184 (12)	0.0294 (14)	0.0000 (14)	0.0067 (15)	0.0076 (11)
N3	0.027 (2)	0.0232 (13)	0.0306 (16)	−0.0034 (13)	0.0036 (14)	0.0093 (12)
C1	0.027 (2)	0.0294 (18)	0.0321 (19)	0.0061 (16)	0.0084 (16)	0.0039 (14)
C2	0.028 (2)	0.0216 (16)	0.0345 (19)	0.0068 (15)	0.0037 (16)	0.0054 (14)
C3	0.028 (2)	0.0198 (15)	0.0264 (17)	−0.0006 (14)	0.0006 (15)	0.0019 (12)
O3	0.031 (2)	0.0273 (14)	0.071 (2)	0.0040 (13)	0.0092 (16)	0.0070 (14)
C4	0.024 (2)	0.0267 (18)	0.040 (2)	0.0058 (15)	0.0078 (17)	0.0102 (15)
C5	0.034 (3)	0.0256 (18)	0.036 (2)	0.0079 (16)	0.0064 (17)	0.0066 (15)
C6	0.026 (2)	0.0202 (16)	0.0323 (18)	0.0002 (14)	−0.0008 (16)	0.0055 (13)
C7	0.028 (2)	0.0210 (16)	0.0304 (18)	−0.0032 (15)	0.0004 (16)	0.0062 (14)
C8	0.026 (2)	0.0224 (15)	0.0249 (16)	−0.0054 (15)	−0.0014 (15)	0.0041 (13)
C9	0.027 (3)	0.0241 (17)	0.0360 (19)	0.0039 (15)	0.0084 (16)	0.0031 (14)
C10	0.031 (3)	0.0180 (16)	0.039 (2)	0.0031 (15)	0.0057 (17)	0.0062 (14)
C11	0.022 (2)	0.0199 (15)	0.0271 (17)	−0.0009 (14)	−0.0007 (15)	0.0050 (13)
C12	0.032 (2)	0.0184 (15)	0.0285 (17)	0.0034 (15)	0.0018 (16)	0.0005 (13)
C13	0.033 (3)	0.0164 (15)	0.0310 (18)	−0.0025 (15)	−0.0038 (16)	0.0022 (13)
C14	0.044 (3)	0.036 (2)	0.055 (3)	−0.003 (2)	−0.003 (2)	0.003 (2)

Geometric parameters (Å, º)

I1—Cd1	2.6909 (5)	C8—C13	1.391 (5)
Cd1—I1^i	2.6909 (5)	C8—C9	1.393 (6)
Cd1—N1	2.297 (3)	C9—C10	1.382 (6)
Cd1—N1^i	2.297 (3)	C10—C11	1.394 (5)
O1—C6	1.237 (4)	C11—C12	1.395 (5)
O2—C11	1.357 (4)	C12—C13	1.384 (6)
N1—C1	1.343 (5)	C1—H1	0.9400
N1—C5	1.346 (6)	C2—H2	0.9400
N2—N3	1.389 (4)	O3—H3O	0.80 (3)
N2—C6	1.340 (5)	C4—H4	0.9400
O2—H2O	0.81 (3)	C5—H5	0.9400
N3—C7	1.270 (5)	C7—H7	0.9400
C1—C2	1.376 (6)	C9—H9	0.9400
C2—C3	1.380 (6)	C10—H10	0.9400
N2—H2N	0.77 (5)	C12—H12	0.9400
C3—C4	1.395 (5)	C13—H13	0.9400
C3—C6	1.503 (5)	C14—H14A	0.9700
O3—C14	1.418 (5)	C14—H14B	0.9700
C4—C5	1.371 (6)	C14—H14C	0.9700
C7—C8	1.471 (5)
I1—Cd1—N1	114.95 (8)	O2—C11—C12	117.9 (3)
I1—Cd1—I1^i	124.29 (2)	O2—C11—C10	122.6 (3)
I1—Cd1—N1^i	102.12 (9)	C10—C11—C12	119.5 (3)
I1^i—Cd1—N1	102.12 (9)	C11—C12—C13	119.4 (4)
N1—Cd1—N1^i	94.92 (11)	C8—C13—C12	121.6 (4)
I1^i—Cd1—N1^i	114.95 (8)	N1—C1—H1	119.00
Cd1—N1—C1	119.9 (3)	C2—C1—H1	119.00
Cd1—N1—C5	122.3 (2)	C1—C2—H2	120.00
C1—N1—C5	117.7 (3)	C3—C2—H2	120.00
N3—N2—C6	119.3 (3)	C14—O3—H3O	111 (5)
C11—O2—H2O	108 (4)	C5—C4—H4	121.00
N2—N3—C7	114.3 (3)	C3—C4—H4	120.00
N1—C1—C2	122.6 (4)	N1—C5—H5	119.00
C1—C2—C3	119.5 (4)	C4—C5—H5	119.00
C6—N2—H2N	125 (3)	C8—C7—H7	119.00
N3—N2—H2N	115 (3)	N3—C7—H7	119.00
C2—C3—C4	118.1 (3)	C8—C9—H9	120.00
C2—C3—C6	117.7 (3)	C10—C9—H9	120.00
C4—C3—C6	124.2 (4)	C11—C10—H10	120.00
C3—C4—C5	119.1 (4)	C9—C10—H10	120.00
N1—C5—C4	122.9 (4)	C11—C12—H12	120.00
N2—C6—C3	116.1 (3)	C13—C12—H12	120.00
O1—C6—C3	119.7 (3)	C8—C13—H13	119.00
O1—C6—N2	124.0 (3)	C12—C13—H13	119.00
N3—C7—C8	122.2 (4)	O3—C14—H14A	110.00
C7—C8—C9	122.7 (3)	O3—C14—H14B	109.00
C7—C8—C13	118.9 (4)	O3—C14—H14C	109.00
C9—C8—C13	118.4 (3)	H14A—C14—H14B	110.00
C8—C9—C10	120.8 (4)	H14A—C14—H14C	109.00
C9—C10—C11	120.3 (4)	H14B—C14—H14C	109.00
I1—Cd1—N1—C1	66.6 (3)	C2—C3—C6—O1	27.7 (5)
I1^i—Cd1—N1—C1	−156.1 (3)	C2—C3—C4—C5	2.5 (6)
N1^i—Cd1—N1—C1	−39.2 (3)	C6—C3—C4—C5	−176.2 (4)
I1—Cd1—N1—C5	−109.3 (3)	C2—C3—C6—N2	−147.5 (4)
I1^i—Cd1—N1—C5	28.1 (3)	C4—C3—C6—O1	−153.5 (4)
N1^i—Cd1—N1—C5	144.9 (3)	C3—C4—C5—N1	0.4 (6)
C1—N1—C5—C4	−1.5 (6)	N3—C7—C8—C9	−4.1 (6)
Cd1—N1—C1—C2	−176.4 (3)	N3—C7—C8—C13	173.8 (4)
C5—N1—C1—C2	−0.4 (6)	C7—C8—C9—C10	176.7 (4)
Cd1—N1—C5—C4	174.5 (3)	C13—C8—C9—C10	−1.2 (6)
C6—N2—N3—C7	−170.1 (4)	C7—C8—C13—C12	−177.1 (4)
N3—N2—C6—O1	0.2 (6)	C9—C8—C13—C12	0.9 (6)
N3—N2—C6—C3	175.1 (3)	C8—C9—C10—C11	1.0 (6)
N2—N3—C7—C8	−178.8 (4)	C9—C10—C11—O2	−180.0 (4)
N1—C1—C2—C3	3.3 (6)	C9—C10—C11—C12	−0.5 (6)
C1—C2—C3—C6	174.6 (3)	O2—C11—C12—C13	179.8 (4)
C1—C2—C3—C4	−4.3 (5)	C10—C11—C12—C13	0.3 (6)
C4—C3—C6—N2	31.2 (5)	C11—C12—C13—C8	−0.5 (6)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O3	0.77 (5)	2.09 (5)	2.849 (4)	174 (4)
O2—H2O···O1^ii	0.81 (3)	1.89 (4)	2.656 (4)	159 (5)
O3—H3O···O2^iii	0.80 (3)	2.03 (2)	2.828 (5)	173 (4)
C4—H4···O3	0.94	2.58	3.291 (5)	133
C7—H7···O3	0.94	2.56	3.327 (5)	140
C1—H1···I1^iv	0.94	3.11	3.811 (4)	133

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