3,5-Bis(salicylideneamino)-1H-1,2,4-triazole methanol solvate

In the crystal structure of the title compound, C₁₆H₁₃N₅O₂·CH₄O, there are intra- and inter­molecular hydrogen bonds. Mol­ecules form dimers, which are extended to afford a ribbon structure. These ribbons are further packed, forming a three-dimensional grid structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.065
• wR factor = 0.159
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O1     -   H1A    ...       1.06 Ang.
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O2     -   H2A    ...       1.04 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15    ..  O2      ..       2.79 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14    ..  O1      ..       2.81 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4     ..  N4      ..       2.64 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C H4 O

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   0 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
   3 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

3,5-Bis(salicylideneamino)-1H-1,2,4-triazole methanol solvate

Crystal data

C16H13N5O2·CH4O	F(000) = 712
Mr = 339.36	Dx = 1.316 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 428 reflections
a = 5.8562 (7) Å	θ = 2.3–17.5°
b = 9.1651 (12) Å	µ = 0.09 mm^−1
c = 31.907 (4) Å	T = 293 K
β = 90.332 (3)°	Block, colourless
V = 1712.5 (4) Å^3	0.28 × 0.24 × 0.22 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3374 independent reflections
Radiation source: sealed tube	1686 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→6
Tmin = 0.97, Tmax = 0.98	k = −7→11
9110 measured reflections	l = −39→30

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0643P)^2] where P = (Fo^2 + 2Fc^2)/3
3374 reflections	(Δ/σ)max < 0.001
240 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.18 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

2.9453 (0.0073) x + 7.2897 (0.0079) y + 10.7001 (0.0396) z = 6.6354 (0.0098)

* 0.0104 (0.0025) C1 * -0.0084 (0.0028) C2 * 0.0013 (0.0028) C3 * 0.0039 (0.0026) C4 * -0.0019 (0.0024) C5 * -0.0053 (0.0023) C6

Rms deviation of fitted atoms = 0.0062

3.2637 (0.0064) x + 7.0279 (0.0085) y + 10.0583 (0.0424) z = 6.7486 (0.0022)

Angle to previous plane (with approximate e.s.d.) = 3.70 (1/5)

* -0.0012 (0.0016) N1 * 0.0027 (0.0016) N2 * -0.0032 (0.0017) C8 * 0.0023 (0.0017) N4 * -0.0006 (0.0017) C9

Rms deviation of fitted atoms = 0.0022

3.5359 (0.0063) x + 6.7679 (0.0085) y + 9.4679 (0.0428) z = 6.6826 (0.0079)

Angle to previous plane (with approximate e.s.d.) = 3.29 (1/5)

* -0.0124 (0.0022) C11 * 0.0115 (0.0024) C12 * -0.0010 (0.0024) C13 * -0.0086 (0.0026) C14 * 0.0075 (0.0026) C15 * 0.0030 (0.0024) C16

Rms deviation of fitted atoms = 0.0084

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
C1	1.1721 (5)	0.1470 (4)	0.19836 (9)	0.0652 (8)
C2	1.2701 (6)	0.0591 (4)	0.22949 (11)	0.0790 (10)
H2	1.4055	0.0092	0.2244	0.095*
C3	1.1631 (7)	0.0473 (4)	0.26788 (11)	0.0796 (10)
H3	1.2297	−0.0096	0.2888	0.096*
C4	0.9612 (6)	0.1174 (4)	0.27589 (10)	0.0745 (10)
H4	0.8917	0.1082	0.3019	0.089*
C5	0.8627 (5)	0.2017 (4)	0.24505 (9)	0.0662 (9)
H5	0.7254	0.2491	0.2504	0.079*
C6	0.9648 (5)	0.2175 (3)	0.20585 (9)	0.0576 (7)
C7	0.8511 (5)	0.3055 (3)	0.17455 (8)	0.0559 (7)
H7	0.7088	0.3451	0.1806	0.067*
C8	0.8159 (5)	0.4212 (3)	0.11162 (8)	0.0541 (7)
C9	0.5763 (5)	0.5677 (3)	0.08722 (8)	0.0496 (7)
C10	0.2655 (5)	0.6937 (3)	0.11037 (9)	0.0560 (7)
H10	0.2905	0.6456	0.1357	0.067*
C11	0.0777 (5)	0.7952 (3)	0.10708 (9)	0.0561 (7)
C12	−0.0566 (5)	0.8191 (4)	0.14269 (10)	0.0705 (9)
H12	−0.0231	0.7704	0.1676	0.085*
C13	−0.2383 (5)	0.9147 (4)	0.14086 (11)	0.0742 (10)
H13	−0.3299	0.9294	0.1642	0.089*
C14	−0.2829 (6)	0.9889 (4)	0.10366 (12)	0.0804 (10)
H14	−0.4062	1.0528	0.1024	0.097*
C15	−0.1486 (6)	0.9701 (4)	0.06862 (11)	0.0802 (10)
H15	−0.1794	1.0224	0.0442	0.096*
C16	0.0318 (5)	0.8732 (4)	0.07009 (10)	0.0657 (9)
C17	1.3512 (8)	0.2341 (5)	0.03626 (13)	0.1053 (15)
H17A	1.3444	0.2278	0.0663	0.158*
H17B	1.5074	0.2273	0.0275	0.158*
H17C	1.2649	0.1556	0.0241	0.158*
N1	0.7299 (4)	0.5392 (3)	0.05723 (7)	0.0585 (7)
H1B	0.746 (5)	0.576 (3)	0.0301 (10)	0.070*
N2	0.8900 (4)	0.4436 (3)	0.07248 (7)	0.0586 (7)
N3	0.9409 (4)	0.3308 (3)	0.13849 (7)	0.0564 (6)
N4	0.6240 (4)	0.4962 (3)	0.12198 (6)	0.0529 (6)
N5	0.4002 (4)	0.6673 (3)	0.07929 (7)	0.0550 (6)
O1	1.2836 (4)	0.1605 (3)	0.16170 (7)	0.0864 (8)
H1A	1.184 (6)	0.216 (4)	0.1388 (11)	0.104*
O2	0.1601 (5)	0.8552 (3)	0.03571 (7)	0.0970 (9)
H2A	0.282 (7)	0.774 (5)	0.0403 (12)	0.116*
O3	1.2594 (4)	0.3676 (3)	0.02309 (7)	0.0820 (8)
H3A	1.133 (6)	0.374 (4)	0.0384 (11)	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0613 (19)	0.076 (2)	0.0582 (18)	0.0121 (18)	0.0069 (15)	0.0075 (15)
C2	0.070 (2)	0.087 (3)	0.080 (2)	0.0285 (19)	0.0074 (18)	0.0123 (19)
C3	0.091 (3)	0.074 (3)	0.074 (2)	0.009 (2)	−0.0081 (19)	0.0164 (18)
C4	0.094 (3)	0.071 (2)	0.0576 (19)	0.002 (2)	0.0055 (17)	0.0119 (16)
C5	0.0617 (19)	0.077 (2)	0.0601 (18)	0.0072 (17)	0.0104 (15)	0.0118 (15)
C6	0.0541 (16)	0.0614 (19)	0.0575 (17)	0.0046 (15)	0.0070 (13)	0.0065 (14)
C7	0.0580 (17)	0.0562 (19)	0.0537 (17)	0.0038 (15)	0.0055 (14)	−0.0023 (13)
C8	0.0547 (16)	0.065 (2)	0.0431 (15)	0.0082 (15)	0.0019 (12)	0.0001 (13)
C9	0.0493 (16)	0.0578 (18)	0.0417 (15)	0.0027 (14)	0.0050 (11)	0.0008 (12)
C10	0.0560 (17)	0.0601 (19)	0.0521 (16)	0.0063 (15)	0.0072 (13)	0.0012 (13)
C11	0.0567 (17)	0.0533 (18)	0.0585 (17)	0.0048 (14)	0.0036 (13)	−0.0057 (13)
C12	0.066 (2)	0.084 (3)	0.0617 (18)	0.0126 (18)	0.0138 (15)	0.0002 (16)
C13	0.056 (2)	0.089 (3)	0.077 (2)	0.0000 (19)	0.0142 (16)	−0.0130 (19)
C14	0.066 (2)	0.074 (2)	0.101 (3)	0.0194 (19)	0.008 (2)	−0.006 (2)
C15	0.079 (2)	0.082 (3)	0.079 (2)	0.024 (2)	0.0036 (19)	0.0150 (18)
C16	0.064 (2)	0.063 (2)	0.070 (2)	0.0119 (17)	0.0071 (16)	0.0072 (16)
C17	0.125 (4)	0.094 (3)	0.097 (3)	0.043 (3)	0.018 (2)	0.022 (2)
N1	0.0582 (14)	0.0713 (19)	0.0460 (13)	0.0119 (13)	0.0110 (12)	0.0096 (12)
N2	0.0553 (15)	0.0697 (17)	0.0510 (13)	0.0122 (13)	0.0086 (11)	0.0072 (12)
N3	0.0583 (14)	0.0621 (17)	0.0488 (13)	0.0120 (12)	0.0044 (11)	0.0015 (11)
N4	0.0575 (14)	0.0570 (15)	0.0443 (12)	0.0080 (12)	0.0067 (10)	0.0032 (10)
N5	0.0544 (14)	0.0606 (17)	0.0501 (13)	0.0080 (12)	0.0050 (11)	0.0050 (11)
O1	0.0736 (16)	0.116 (2)	0.0698 (15)	0.0360 (15)	0.0201 (12)	0.0233 (13)
O2	0.101 (2)	0.122 (2)	0.0672 (14)	0.0505 (17)	0.0238 (13)	0.0233 (14)
O3	0.0807 (16)	0.103 (2)	0.0622 (14)	0.0301 (15)	0.0224 (12)	0.0177 (12)

Geometric parameters (Å, º)

C1—O1	1.349 (3)	C10—H10	0.9300
C1—C6	1.397 (4)	C11—C12	1.403 (4)
C1—C2	1.399 (4)	C11—C16	1.404 (4)
C2—C3	1.383 (5)	C12—C13	1.380 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.371 (5)	C13—C14	1.391 (5)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.375 (4)	C14—C15	1.381 (5)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.397 (4)	C15—C16	1.381 (4)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.443 (4)	C16—O2	1.343 (4)
C7—N3	1.289 (3)	C17—O3	1.400 (5)
C7—H7	0.9300	C17—H17A	0.9600
C8—N2	1.340 (3)	C17—H17B	0.9600
C8—N4	1.360 (3)	C17—H17C	0.9600
C8—N3	1.397 (3)	N1—N2	1.371 (3)
C9—N4	1.317 (3)	N1—H1B	0.94 (3)
C9—N1	1.343 (3)	N2—O3	2.773 (3)
C9—N5	1.399 (3)	O1—H1A	1.06 (4)
C10—N5	1.293 (3)	O2—H2A	1.05 (4)
C10—C11	1.444 (4)	O3—H3A	0.89 (4)
O1—C1—C6	122.1 (3)	C13—C12—H12	120.0
O1—C1—C2	118.0 (3)	C11—C12—H12	120.0
C6—C1—C2	119.9 (3)	C12—C13—C14	119.2 (3)
C3—C2—C1	119.2 (3)	C12—C13—H13	120.4
C3—C2—H2	120.4	C14—C13—H13	120.4
C1—C2—H2	120.4	C15—C14—C13	121.6 (3)
C4—C3—C2	121.6 (3)	C15—C14—H14	119.2
C4—C3—H3	119.2	C13—C14—H14	119.2
C2—C3—H3	119.2	C16—C15—C14	119.4 (3)
C3—C4—C5	119.3 (3)	C16—C15—H15	120.3
C3—C4—H4	120.4	C14—C15—H15	120.3
C5—C4—H4	120.4	O2—C16—C15	118.8 (3)
C4—C5—C6	121.2 (3)	O2—C16—C11	121.2 (3)
C4—C5—H5	119.4	C15—C16—C11	119.9 (3)
C6—C5—H5	119.4	O3—C17—H17A	109.5
C1—C6—C5	118.8 (3)	O3—C17—H17B	109.5
C1—C6—C7	122.6 (3)	H17A—C17—H17B	109.5
C5—C6—C7	118.6 (3)	O3—C17—H17C	109.5
N3—C7—C6	121.9 (3)	H17A—C17—H17C	109.5
N3—C7—H7	119.0	H17B—C17—H17C	109.5
C6—C7—H7	119.0	C9—N1—N2	109.3 (2)
N2—C8—N4	114.9 (2)	C9—N1—H1B	131.4 (19)
N2—C8—N3	119.4 (2)	N2—N1—H1B	119.2 (19)
N4—C8—N3	125.6 (2)	C8—N2—N1	101.8 (2)
N4—C9—N1	111.3 (3)	C8—N2—O3	138.50 (19)
N4—C9—N5	129.0 (2)	N1—N2—O3	119.55 (16)
N1—C9—N5	119.6 (2)	C7—N3—C8	116.1 (2)
N5—C10—C11	122.1 (3)	C9—N4—C8	102.6 (2)
N5—C10—H10	118.9	C10—N5—C9	115.8 (2)
C11—C10—H10	118.9	C1—O1—H1A	112.1 (19)
C12—C11—C16	119.7 (3)	C16—O2—H2A	111 (2)
C12—C11—C10	118.2 (3)	C17—O3—N2	110.4 (2)
C16—C11—C10	122.1 (3)	C17—O3—H3A	102 (2)
C13—C12—C11	120.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N5	1.05 (4)	1.72 (4)	2.618 (3)	141 (3)
O1—H1A···N3	1.06 (4)	1.77 (4)	2.645 (3)	137 (3)
O3—H3A···N2	0.89 (4)	1.91 (4)	2.773 (3)	164 (4)
N1—H1B···O3^i	0.94 (3)	1.77 (3)	2.702 (3)	172 (3)
C15—H15···O2^ii	0.93	2.79	3.694 (4)	164
C14—H14···O1^iii	0.93	2.81	3.522 (4)	134
C4—H4···N4^iv	0.93	2.64	3.481 (4)	151

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