Naphthalene-2,7-diol–1,2,4-triazole (2/1)

In the crystal structure of the title compound, 2C₁₀H₈O₂·C₂H₃N₃, inter­molecular N—H...O, O—H...N and O—H...O hydrogen bonds connect naphthalene-2,7-diol mol­ecules and 1,2,4-tridazole mol­ecules into a linear ribbon motif.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.076
• wR factor = 0.215
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         38 Perc.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

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

   1 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
   2 ALERT type 3 Indicator that the structure quality may be low
   0 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, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

Naphthalene-2,7-diol–1,2,4-triazole (2/1)

Crystal data

2C10H8O2·C2H3N3	F(000) = 816
Mr = 389.40	Dx = 1.328 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 542 reflections
a = 20.754 (4) Å	θ = 2.5–19.2°
b = 5.890 (1) Å	µ = 0.09 mm^−1
c = 16.273 (4) Å	T = 295 K
β = 101.682 (6)°	Bar, colorless
V = 1948.0 (7) Å^3	0.4 × 0.3 × 0.3 mm
Z = 4

Data collection

Bruker SMART 1K area-detector diffractometer	1489 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.090
Graphite monochromator	θmax = 26.3°, θmin = 2.6°
φ and ω scans	h = −25→23
8911 measured reflections	k = −7→5
3918 independent reflections	l = −20→19

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)] = 0.076	H-atom parameters constrained
wR(F^2) = 0.215	w = 1/[σ^2(Fo^2) + (0.0838P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max = 0.001
3918 reflections	Δρmax = 0.22 e Å^−3
267 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (2)

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

	x	y	z	Uiso*/Ueq
O1	0.6149 (2)	1.0277 (7)	0.4834 (2)	0.094 (1)
O2	0.9477 (1)	0.6577 (6)	0.6623 (2)	0.080 (1)
O3	0.4134 (1)	0.4996 (6)	0.7602 (2)	0.077 (1)
O4	0.0725 (1)	0.8055 (5)	0.7295 (2)	0.070 (1)
N1	0.5625 (2)	0.6792 (7)	0.5624 (3)	0.071 (1)
N2	0.5033 (2)	0.5226 (9)	0.6438 (3)	0.079 (1)
N3	0.5549 (2)	0.3862 (7)	0.6456 (3)	0.075 (1)
C1	0.7231 (2)	0.8969 (8)	0.5460 (3)	0.059 (1)
C2	0.6817 (3)	1.0523 (9)	0.5017 (3)	0.066 (1)
C3	0.7061 (3)	1.2504 (9)	0.4705 (3)	0.078 (2)
C4	0.7724 (4)	1.2826 (9)	0.4835 (3)	0.080 (2)
C5	0.8172 (3)	1.1228 (8)	0.5272 (3)	0.065 (1)
C6	0.7915 (2)	0.9271 (7)	0.5598 (2)	0.052 (1)
C7	0.8361 (2)	0.7693 (7)	0.6052 (3)	0.053 (1)
C8	0.9019 (2)	0.8030 (8)	0.6173 (3)	0.061 (1)
C9	0.9264 (3)	0.998 (1)	0.5832 (3)	0.080 (2)
C10	0.8860 (3)	1.155 (1)	0.5402 (3)	0.081 (2)
C11	0.3009 (2)	0.6012 (7)	0.7533 (3)	0.052 (1)
C12	0.3471 (2)	0.4537 (8)	0.7372 (3)	0.054 (1)
C13	0.3282 (3)	0.2482 (8)	0.6962 (3)	0.066 (1)
C14	0.2639 (3)	0.1959 (8)	0.6712 (3)	0.065 (1)
C15	0.2147 (2)	0.3437 (8)	0.6865 (3)	0.052 (1)
C16	0.2338 (2)	0.5526 (7)	0.7290 (2)	0.047 (1)
C17	0.1839 (2)	0.7024 (7)	0.7426 (3)	0.050 (1)
C18	0.1195 (2)	0.6510 (8)	0.7145 (3)	0.053 (1)
C19	0.0997 (2)	0.4481 (8)	0.6715 (3)	0.065 (1)
C20	0.1474 (2)	0.2983 (8)	0.6587 (3)	0.065 (1)
C21	0.5081 (2)	0.6925 (9)	0.5917 (3)	0.066 (1)
C22	0.5883 (2)	0.486 (1)	0.5965 (3)	0.071 (2)
H1o	0.6037	0.9247	0.5144	0.113*
H2o	0.9293	0.5744	0.6936	0.096*
H3o	0.4313	0.4824	0.7180	0.093*
H4o	0.0343	0.7501	0.7127	0.084*
H3n	0.5638	0.2628	0.6725	0.090*
H1	0.7059	0.7691	0.5673	0.071*
H3	0.6774	1.3577	0.4413	0.094*
H4	0.7886	1.4137	0.4630	0.096*
H7	0.8201	0.6400	0.6271	0.063*
H9	0.9716	1.0179	0.5908	0.096*
H10	0.9032	1.2828	0.5192	0.097*
H11	0.3141	0.7368	0.7809	0.062*
H13	0.3601	0.1470	0.6862	0.079*
H14	0.2521	0.0596	0.6434	0.078*
H17	0.1953	0.8379	0.7711	0.060*
H19	0.0554	0.4159	0.6522	0.078*
H20	0.1347	0.1627	0.6307	0.077*
H21	0.4768	0.8067	0.5778	0.079*
H22	0.6273	0.4263	0.5860	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.103 (3)	0.082 (3)	0.097 (3)	0.039 (2)	0.022 (2)	0.034 (2)
O2	0.056 (2)	0.078 (3)	0.102 (3)	−0.012 (2)	0.004 (2)	0.018 (2)
O3	0.053 (2)	0.091 (3)	0.091 (3)	0.012 (2)	0.022 (2)	−0.009 (2)
O4	0.047 (2)	0.056 (2)	0.105 (3)	−0.003 (2)	0.010 (2)	−0.013 (2)
N1	0.056 (2)	0.072 (3)	0.083 (3)	0.012 (2)	0.007 (2)	0.008 (2)
N2	0.050 (2)	0.087 (4)	0.097 (3)	0.013 (2)	0.006 (2)	−0.004 (3)
N3	0.060 (2)	0.071 (3)	0.095 (3)	0.026 (2)	0.015 (2)	0.022 (3)
C1	0.079 (3)	0.044 (3)	0.054 (3)	0.012 (3)	0.015 (3)	0.011 (2)
C2	0.086 (4)	0.057 (4)	0.054 (3)	0.017 (3)	0.014 (3)	0.003 (3)
C3	0.139 (5)	0.042 (4)	0.056 (3)	0.022 (4)	0.025 (4)	0.014 (3)
C4	0.145 (5)	0.041 (4)	0.056 (3)	−0.016 (4)	0.025 (4)	−0.004 (3)
C5	0.114 (4)	0.038 (3)	0.040 (3)	−0.011 (3)	0.007 (3)	−0.004 (2)
C6	0.080 (3)	0.033 (3)	0.044 (3)	−0.004 (2)	0.013 (2)	0.003 (2)
C7	0.069 (3)	0.035 (3)	0.056 (3)	−0.005 (2)	0.015 (2)	0.004 (2)
C8	0.065 (3)	0.056 (4)	0.062 (3)	−0.019 (3)	0.013 (3)	−0.007 (3)
C9	0.080 (4)	0.076 (4)	0.080 (4)	−0.036 (3)	0.009 (3)	0.006 (3)
C10	0.109 (5)	0.065 (4)	0.063 (3)	−0.038 (4)	0.005 (3)	0.012 (3)
C11	0.061 (3)	0.040 (3)	0.054 (3)	−0.001 (2)	0.011 (2)	−0.003 (2)
C12	0.064 (3)	0.048 (3)	0.052 (3)	0.009 (3)	0.015 (2)	0.003 (2)
C13	0.084 (4)	0.049 (3)	0.070 (3)	0.012 (3)	0.030 (3)	−0.009 (3)
C14	0.090 (4)	0.045 (3)	0.063 (3)	0.000 (3)	0.026 (3)	−0.013 (2)
C15	0.069 (3)	0.043 (3)	0.048 (3)	−0.010 (3)	0.019 (2)	0.002 (2)
C16	0.058 (3)	0.033 (3)	0.051 (3)	−0.001 (2)	0.010 (2)	−0.001 (2)
C17	0.052 (3)	0.038 (3)	0.055 (3)	−0.009 (2)	0.003 (2)	−0.011 (2)
C18	0.064 (3)	0.037 (3)	0.057 (3)	−0.005 (2)	0.006 (2)	−0.001 (2)
C19	0.072 (3)	0.051 (3)	0.068 (3)	−0.026 (3)	0.005 (3)	−0.009 (3)
C20	0.082 (4)	0.044 (3)	0.067 (3)	−0.017 (3)	0.014 (3)	−0.012 (2)
C21	0.043 (3)	0.057 (4)	0.095 (4)	0.018 (2)	0.005 (3)	0.010 (3)
C22	0.056 (3)	0.081 (4)	0.079 (4)	0.012 (3)	0.018 (3)	0.009 (3)

Geometric parameters (Å, º)

O1—C2	1.365 (6)	C15—C20	1.404 (6)
O2—C8	1.375 (5)	C15—C16	1.428 (5)
O3—C12	1.378 (5)	C16—C17	1.411 (5)
O4—C18	1.392 (5)	C17—C18	1.355 (5)
N1—C21	1.313 (5)	C18—C19	1.404 (6)
N1—C22	1.332 (6)	C19—C20	1.373 (6)
N2—C21	1.327 (6)	O1—H1o	0.85
N2—N3	1.333 (5)	O2—H2o	0.85
N3—C22	1.299 (5)	O3—H3o	0.85
C1—C2	1.358 (6)	O4—H4o	0.85
C1—C6	1.402 (6)	N3—H3n	0.85
C2—C3	1.408 (7)	C1—H1	0.93
C3—C4	1.362 (7)	C3—H3	0.93
C4—C5	1.410 (7)	C4—H4	0.93
C5—C10	1.412 (7)	C7—H7	0.93
C5—C6	1.418 (6)	C9—H9	0.93
C6—C7	1.411 (6)	C10—H10	0.93
C7—C8	1.353 (6)	C11—H11	0.93
C8—C9	1.412 (6)	C13—H13	0.93
C9—C10	1.345 (7)	C14—H14	0.93
C11—C12	1.358 (6)	C17—H17	0.93
C11—C16	1.399 (5)	C19—H19	0.93
C12—C13	1.399 (6)	C20—H20	0.93
C13—C14	1.348 (6)	C21—H21	0.93
C14—C15	1.403 (6)	C22—H22	0.93
C21—N1—C22	101.7 (4)	C19—C20—C15	122.0 (4)
C21—N2—N3	107.8 (4)	N1—C21—N2	111.5 (4)
C22—N3—N2	103.9 (4)	N3—C22—N1	115.0 (4)
C2—C1—C6	120.7 (5)	C2—O1—H1o	109.5
C1—C2—O1	123.4 (5)	C8—O2—H2o	109.5
C1—C2—C3	120.9 (5)	C12—O3—H3o	109.5
O1—C2—C3	115.7 (5)	C18—O4—H4o	109.5
C4—C3—C2	119.1 (5)	C22—N3—H3n	128.0
C3—C4—C5	121.9 (5)	N2—N3—H3n	128.0
C4—C5—C10	122.0 (5)	C2—C1—H1	119.6
C4—C5—C6	118.1 (5)	C6—C1—H1	119.6
C10—C5—C6	119.9 (5)	C4—C3—H3	120.5
C1—C6—C7	122.5 (4)	C2—C3—H3	120.5
C1—C6—C5	119.3 (4)	C3—C4—H4	119.1
C7—C6—C5	118.2 (4)	C5—C4—H4	119.1
C8—C7—C6	121.1 (4)	C8—C7—H7	119.5
C7—C8—O2	123.7 (4)	C6—C7—H7	119.5
C7—C8—C9	119.7 (5)	C10—C9—H9	119.1
O2—C8—C9	116.7 (4)	C8—C9—H9	119.1
C10—C9—C8	121.7 (5)	C9—C10—H10	120.3
C9—C10—C5	119.4 (5)	C5—C10—H10	120.3
C12—C11—C16	121.1 (4)	C12—C11—H11	119.5
C11—C12—O3	121.8 (4)	C16—C11—H11	119.5
C11—C12—C13	120.3 (4)	C14—C13—H13	119.8
O3—C12—C13	117.9 (4)	C12—C13—H13	119.8
C14—C13—C12	120.4 (4)	C13—C14—H14	119.5
C13—C14—C15	121.1 (4)	C15—C14—H14	119.5
C14—C15—C20	122.6 (5)	C18—C17—H17	119.6
C14—C15—C16	118.7 (4)	C16—C17—H17	119.6
C20—C15—C16	118.7 (4)	C20—C19—H19	120.8
C11—C16—C17	123.2 (4)	C18—C19—H19	120.8
C11—C16—C15	118.4 (4)	C19—C20—H20	119.0
C17—C16—C15	118.3 (4)	C15—C20—H20	119.0
C18—C17—C16	120.8 (4)	N1—C21—H21	124.2
C17—C18—O4	118.2 (4)	N2—C21—H21	124.2
C17—C18—C19	121.8 (4)	N3—C22—H22	122.5
O4—C18—C19	120.0 (4)	N1—C22—H22	122.5
C20—C19—C18	118.4 (4)
C21—N2—N3—C22	1.8 (5)	C11—C12—C13—C14	1.1 (7)
C6—C1—C2—O1	177.3 (4)	O3—C12—C13—C14	−179.1 (4)
C6—C1—C2—C3	−1.7 (7)	C12—C13—C14—C15	−0.9 (7)
C1—C2—C3—C4	1.5 (7)	C13—C14—C15—C20	177.7 (4)
O1—C2—C3—C4	−177.6 (4)	C13—C14—C15—C16	0.2 (6)
C2—C3—C4—C5	0.2 (7)	C12—C11—C16—C17	−178.5 (4)
C3—C4—C5—C10	179.4 (5)	C12—C11—C16—C15	−0.2 (6)
C3—C4—C5—C6	−1.7 (7)	C14—C15—C16—C11	0.3 (6)
C2—C1—C6—C7	−179.8 (4)	C20—C15—C16—C11	−177.2 (4)
C2—C1—C6—C5	0.2 (6)	C14—C15—C16—C17	178.7 (4)
C4—C5—C6—C1	1.5 (6)	C20—C15—C16—C17	1.2 (6)
C10—C5—C6—C1	−179.6 (4)	C11—C16—C17—C18	177.1 (4)
C4—C5—C6—C7	−178.6 (4)	C15—C16—C17—C18	−1.2 (6)
C10—C5—C6—C7	0.3 (6)	C16—C17—C18—O4	−179.9 (4)
C1—C6—C7—C8	179.8 (4)	C16—C17—C18—C19	0.4 (6)
C5—C6—C7—C8	−0.1 (6)	C17—C18—C19—C20	0.6 (7)
C6—C7—C8—O2	178.6 (4)	O4—C18—C19—C20	−179.2 (4)
C6—C7—C8—C9	−0.8 (7)	C18—C19—C20—C15	−0.6 (7)
C7—C8—C9—C10	1.4 (7)	C14—C15—C20—C19	−177.7 (4)
O2—C8—C9—C10	−178.0 (5)	C16—C15—C20—C19	−0.3 (6)
C8—C9—C10—C5	−1.1 (8)	C22—N1—C21—N2	3.0 (6)
C4—C5—C10—C9	179.2 (5)	N3—N2—C21—N1	−3.1 (6)
C6—C5—C10—C9	0.3 (7)	N2—N3—C22—N1	0.1 (6)
C16—C11—C12—O3	179.6 (4)	C21—N1—C22—N3	−1.9 (6)
C16—C11—C12—C13	−0.5 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.85	1.93	2.760 (6)	167
O2—H2o···O4^i	0.85	2.02	2.806 (5)	153
O3—H3o···N2	0.85	2.12	2.920 (5)	157
O4—H4o···O2^ii	0.85	1.90	2.743 (4)	172
N3—H3n···O3^i	0.85	1.90	2.750 (5)	176

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