Synthesis, crystal structure and Hirshfeld surface analysis of 5-[2-(di­cyano­methyl­idene)hydrazin-1-yl]-2,4,6-tri­iodo­isophthalic acid ethanol monosolvate

In the crystal, pairs of mol­ecules are linked by O—H...O and N—H...O hydrogen bonds forming dimers with (14) motifs. These dimers are connected by O—H...O hydrogen bonds into chains along the a-axis direction, forming (16) ring motifs. Further O—H...O inter­actions involving the ethanol solvent mol­ecule connect the chains into a three-dimensional network.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.024
• wR factor = 0.054
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600        134 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         55 Note
PLAT977_ALERT_2_C Check Negative Difference Density on H12A      .      -0.35 eA-3

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT019_ALERT_1_G _diffrn_measured_fraction_theta_full/*_max < 1.0      0.995 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT431_ALERT_2_G Short Inter HL..A Contact  I1       ..N4       .       3.22 Ang.
                                                1-x,1-y,2-z  =      2_667 Check
PLAT431_ALERT_2_G Short Inter HL..A Contact  I2       ..N3       .       3.25 Ang.
                                             -1+x,-1+y,-1+z  =      1_444 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          2 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   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

   2 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX4 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXT2019/1 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/1 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

5-[2-(Dicyanomethylidene)hydrazin-1-yl]-2,4,6-triiodoisophthalic acid ethanol monosolvate

Crystal data

C11H3I3N4O4·C2H6O	Z = 2
Mr = 681.94	F(000) = 628
Triclinic, P1	Dx = 2.386 Mg m^−3
a = 9.1499 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8771 (3) Å	Cell parameters from 9873 reflections
c = 12.0440 (4) Å	θ = 2.3–26.4°
α = 113.512 (1)°	µ = 4.97 mm^−1
β = 95.399 (1)°	T = 296 K
γ = 103.462 (1)°	Prism, orange
V = 949.11 (5) Å^3	0.26 × 0.21 × 0.14 mm

Data collection

Bruker D8 Quest PHOTON 100 detector diffractometer	3375 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.025
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 26.4°, θmin = 2.3°
Tmin = 0.325, Tmax = 0.518	h = −11→11
20253 measured reflections	k = −12→12
3755 independent reflections	l = −15→15

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)] = 0.024	Hydrogen site location: mixed
wR(F^2) = 0.054	H-atom parameters constrained
S = 1.22	w = 1/[σ^2(Fo^2) + 2.2238P] where P = (Fo^2 + 2Fc^2)/3
3755 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.75 e Å^−3
0 restraints	Δρmin = −0.61 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.43837 (3)	0.36375 (3)	0.66860 (2)	0.03614 (8)
I2	0.00185 (3)	0.27921 (3)	0.22009 (2)	0.03995 (8)
I3	0.34230 (3)	0.92158 (3)	0.61552 (3)	0.04489 (9)
O1	0.0961 (3)	0.1098 (3)	0.4380 (3)	0.0419 (6)
H1	0.063676	0.171314	0.495416	0.063*
O2	0.2676 (3)	0.1256 (3)	0.3246 (2)	0.0380 (6)
O3	0.1880 (3)	0.6581 (4)	0.2734 (3)	0.0433 (7)
H3	0.165558	0.704626	0.231145	0.065*
O4	0.0089 (3)	0.7033 (4)	0.3831 (3)	0.0438 (7)
O5	1.0910 (4)	0.7945 (4)	0.1586 (3)	0.0600 (9)
H5	1.151655	0.834890	0.123379	0.090*
N1	0.4566 (3)	0.7189 (3)	0.7341 (3)	0.0315 (6)
H1N	0.532784	0.799315	0.735139	0.038*
N2	0.4222 (3)	0.7013 (4)	0.8311 (3)	0.0326 (6)
N3	0.7600 (5)	1.0028 (5)	0.9762 (4)	0.0656 (12)
N4	0.4455 (6)	0.7440 (5)	1.1278 (4)	0.0656 (12)
C1	0.3561 (4)	0.6188 (4)	0.6179 (3)	0.0260 (7)
C2	0.3273 (3)	0.4583 (4)	0.5705 (3)	0.0249 (6)
C3	0.2269 (4)	0.3621 (4)	0.4560 (3)	0.0262 (7)
C4	0.1576 (4)	0.4260 (4)	0.3895 (3)	0.0258 (7)
C5	0.1879 (4)	0.5859 (4)	0.4348 (3)	0.0267 (7)
C6	0.2875 (4)	0.6808 (4)	0.5487 (3)	0.0262 (7)
C7	0.5133 (4)	0.7872 (4)	0.9390 (3)	0.0348 (8)
C8	0.6530 (5)	0.9076 (5)	0.9622 (3)	0.0398 (9)
C9	0.4713 (5)	0.7606 (5)	1.0428 (4)	0.0437 (9)
C10	0.1991 (4)	0.1893 (4)	0.4015 (3)	0.0296 (7)
C11	0.1178 (4)	0.6559 (4)	0.3606 (3)	0.0294 (7)
C12	0.8376 (7)	0.6247 (7)	0.0688 (6)	0.0785 (17)
H12A	0.731327	0.619981	0.052211	0.118*
H12B	0.850672	0.568988	0.116680	0.118*
H12C	0.869243	0.579198	−0.008073	0.118*
C13	0.9323 (6)	0.7882 (7)	0.1389 (5)	0.0646 (14)
H13A	0.915521	0.846280	0.092754	0.078*
H13B	0.903196	0.833807	0.217868	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.04006 (14)	0.03692 (13)	0.03368 (13)	0.01326 (10)	0.00214 (10)	0.01774 (10)
I2	0.03979 (14)	0.03778 (14)	0.02815 (13)	0.00210 (10)	−0.00658 (10)	0.00856 (10)
I3	0.05157 (16)	0.02331 (12)	0.05002 (16)	0.00527 (10)	0.00314 (12)	0.01113 (11)
O1	0.0475 (16)	0.0294 (13)	0.0477 (16)	0.0067 (12)	0.0229 (13)	0.0155 (12)
O2	0.0432 (15)	0.0294 (13)	0.0371 (14)	0.0089 (11)	0.0160 (12)	0.0095 (11)
O3	0.0468 (16)	0.0641 (18)	0.0457 (16)	0.0286 (14)	0.0219 (13)	0.0408 (15)
O4	0.0432 (15)	0.0589 (18)	0.0422 (15)	0.0288 (14)	0.0164 (12)	0.0255 (14)
O5	0.0564 (19)	0.069 (2)	0.081 (2)	0.0197 (17)	0.0171 (17)	0.057 (2)
N1	0.0339 (15)	0.0276 (14)	0.0257 (14)	−0.0020 (12)	0.0005 (12)	0.0119 (12)
N2	0.0340 (16)	0.0339 (16)	0.0241 (14)	0.0074 (13)	0.0016 (12)	0.0092 (12)
N3	0.062 (3)	0.061 (3)	0.054 (2)	−0.010 (2)	−0.002 (2)	0.023 (2)
N4	0.082 (3)	0.072 (3)	0.033 (2)	0.004 (2)	0.0039 (19)	0.024 (2)
C1	0.0239 (15)	0.0290 (16)	0.0196 (15)	0.0023 (13)	0.0028 (12)	0.0087 (13)
C2	0.0204 (15)	0.0278 (16)	0.0241 (15)	0.0027 (12)	0.0015 (12)	0.0120 (13)
C3	0.0233 (15)	0.0291 (16)	0.0259 (16)	0.0038 (13)	0.0060 (13)	0.0137 (14)
C4	0.0261 (16)	0.0253 (16)	0.0209 (15)	0.0028 (13)	0.0038 (12)	0.0079 (13)
C5	0.0283 (16)	0.0293 (16)	0.0229 (15)	0.0068 (13)	0.0076 (13)	0.0122 (13)
C6	0.0281 (16)	0.0217 (15)	0.0269 (16)	0.0042 (13)	0.0066 (13)	0.0102 (13)
C7	0.0380 (19)	0.0336 (18)	0.0267 (17)	0.0075 (15)	0.0001 (15)	0.0102 (15)
C8	0.048 (2)	0.035 (2)	0.0275 (18)	0.0093 (18)	−0.0007 (16)	0.0084 (16)
C9	0.049 (2)	0.044 (2)	0.0283 (19)	0.0081 (18)	−0.0034 (17)	0.0112 (17)
C10	0.0291 (17)	0.0253 (16)	0.0278 (17)	0.0029 (14)	0.0030 (14)	0.0087 (14)
C11	0.0313 (17)	0.0289 (17)	0.0262 (16)	0.0062 (14)	0.0065 (14)	0.0116 (14)
C12	0.073 (4)	0.077 (4)	0.068 (4)	0.007 (3)	0.005 (3)	0.024 (3)
C13	0.063 (3)	0.072 (3)	0.058 (3)	0.016 (3)	−0.009 (2)	0.034 (3)

Geometric parameters (Å, º)

I1—C2	2.097 (3)	C1—C6	1.397 (5)
I2—C4	2.104 (3)	C1—C2	1.401 (5)
I3—C6	2.097 (3)	C2—C3	1.399 (4)
O1—C10	1.307 (4)	C3—C4	1.392 (5)
O1—H1	0.8499	C3—C10	1.511 (5)
O2—C10	1.214 (4)	C4—C5	1.396 (5)
O3—C11	1.287 (4)	C5—C6	1.390 (5)
O3—H3	0.8500	C5—C11	1.510 (5)
O4—C11	1.205 (4)	C7—C8	1.444 (6)
O5—C13	1.432 (6)	C7—C9	1.445 (6)
O5—H5	0.8500	C12—C13	1.481 (8)
N1—N2	1.303 (4)	C12—H12A	0.9600
N1—C1	1.419 (4)	C12—H12B	0.9600
N1—H1N	0.9222	C12—H12C	0.9600
N2—C7	1.300 (5)	C13—H13A	0.9700
N3—C8	1.134 (6)	C13—H13B	0.9700
N4—C9	1.136 (6)
C10—O1—H1	109.4	C1—C6—I3	119.1 (2)
C11—O3—H3	120.3	N2—C7—C8	124.6 (3)
C13—O5—H5	119.8	N2—C7—C9	117.6 (3)
N2—N1—C1	117.7 (3)	C8—C7—C9	117.8 (3)
N2—N1—H1N	125.8	N3—C8—C7	177.0 (4)
C1—N1—H1N	115.9	N4—C9—C7	176.6 (5)
C7—N2—N1	119.9 (3)	O2—C10—O1	120.9 (3)
C6—C1—C2	119.5 (3)	O2—C10—C3	121.4 (3)
C6—C1—N1	119.8 (3)	O1—C10—C3	117.6 (3)
C2—C1—N1	120.7 (3)	O4—C11—O3	125.5 (3)
C3—C2—C1	119.5 (3)	O4—C11—C5	122.5 (3)
C3—C2—I1	120.3 (2)	O3—C11—C5	112.0 (3)
C1—C2—I1	120.1 (2)	C13—C12—H12A	109.5
C4—C3—C2	120.0 (3)	C13—C12—H12B	109.5
C4—C3—C10	119.7 (3)	H12A—C12—H12B	109.5
C2—C3—C10	120.2 (3)	C13—C12—H12C	109.5
C3—C4—C5	120.9 (3)	H12A—C12—H12C	109.5
C3—C4—I2	119.4 (2)	H12B—C12—H12C	109.5
C5—C4—I2	119.7 (2)	O5—C13—C12	109.1 (5)
C6—C5—C4	118.8 (3)	O5—C13—H13A	109.9
C6—C5—C11	120.1 (3)	C12—C13—H13A	109.9
C4—C5—C11	121.0 (3)	O5—C13—H13B	109.9
C5—C6—C1	121.2 (3)	C12—C13—H13B	109.9
C5—C6—I3	119.6 (2)	H13A—C13—H13B	108.3
C1—N1—N2—C7	177.9 (3)	C4—C5—C6—C1	−0.3 (5)
N2—N1—C1—C6	121.9 (3)	C11—C5—C6—C1	−178.8 (3)
N2—N1—C1—C2	−59.3 (4)	C4—C5—C6—I3	177.5 (2)
C6—C1—C2—C3	−1.7 (5)	C11—C5—C6—I3	−1.0 (4)
N1—C1—C2—C3	179.5 (3)	C2—C1—C6—C5	1.6 (5)
C6—C1—C2—I1	176.7 (2)	N1—C1—C6—C5	−179.7 (3)
N1—C1—C2—I1	−2.0 (4)	C2—C1—C6—I3	−176.2 (2)
C1—C2—C3—C4	0.6 (5)	N1—C1—C6—I3	2.5 (4)
I1—C2—C3—C4	−177.8 (2)	N1—N2—C7—C8	1.6 (6)
C1—C2—C3—C10	177.7 (3)	N1—N2—C7—C9	−178.7 (3)
I1—C2—C3—C10	−0.7 (4)	C4—C3—C10—O2	79.7 (4)
C2—C3—C4—C5	0.6 (5)	C2—C3—C10—O2	−97.4 (4)
C10—C3—C4—C5	−176.5 (3)	C4—C3—C10—O1	−98.9 (4)
C2—C3—C4—I2	−178.2 (2)	C2—C3—C10—O1	84.0 (4)
C10—C3—C4—I2	4.7 (4)	C6—C5—C11—O4	−79.6 (5)
C3—C4—C5—C6	−0.8 (5)	C4—C5—C11—O4	102.0 (4)
I2—C4—C5—C6	178.0 (2)	C6—C5—C11—O3	100.3 (4)
C3—C4—C5—C11	177.6 (3)	C4—C5—C11—O3	−78.1 (4)
I2—C4—C5—C11	−3.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4^i	0.85	1.80	2.648 (4)	178
O3—H3···O5^ii	0.85	1.68	2.515 (4)	169
O5—H5···N3^iii	0.85	2.40	3.200 (5)	156
N1—H1N···O2^iv	0.92	2.11	2.937 (4)	149

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