Bis(5-methyl-1-phenyl-1H-1,2,3-triazole-4-carb-oxy-lic acid) monohydrate.

The crystal structure of the title compound, 2C(10)H(9)N(3)O(2)·H(2)O, synthesized from azido-benzene and ethyl acetyl-acetate, is stabilized by O-H⋯O and O-H⋯N hydrogen bonds.

Related literature

The title compound was studied as part of our search for phase transition materials, see: Li et al. (2008 ▶); Zhang et al. (2009 ▶). For the preparation, see: El Khadem et al. (1968 ▶). For the biological activity of triazoles, see: Olesen et al. (2003 ▶) Tian et al. (2005 ▶). For a related structure, see: Lin (2008 ▶).

Experimental

Crystal data

2C10H9N3O2·H2O

M = 424.42

Monoclinic,

a = 6.7419 (13) Å

b = 15.842 (3) Å

c = 19.643 (4) Å

β = 99.82 (3)°

V = 2067.2 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.42 × 0.38 × 0.35 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.947, T max = 0.951

20838 measured reflections

4733 independent reflections

3206 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.172

S = 0.87

4733 reflections

292 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810026243/jh2161sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026243/jh2161Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

2C10H9N3O2·H2O	F(000) = 888
Mr = 424.42	Dx = 1.364 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8429 reflections
a = 6.7419 (13) Å	θ = 3.1–27.7°
b = 15.842 (3) Å	µ = 0.10 mm−1
c = 19.643 (4) Å	T = 293 K
β = 99.82 (3)°	Prism, colorless
V = 2067.2 (7) Å3	0.42 × 0.38 × 0.35 mm
Z = 4

Rigaku SCXmini diffractometer	4733 independent reflections
Radiation source: fine-focus sealed tube	3206 reflections with I > 2σ(I)
graphite	Rint = 0.056
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD_Profile_fitting scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −20→20
Tmin = 0.947, Tmax = 0.951	l = −25→25
20838 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	w = 1/[σ2(Fo2) + (0.1083P)2 + 0.6293P] where P = (Fo2 + 2Fc2)/3
4733 reflections	(Δ/σ)max < 0.001
292 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq
O4	−0.2245 (3)	0.25435 (10)	1.04831 (9)	0.0616 (5)
H4	−0.3031	0.2478	1.0754	0.092*
N1	0.3101 (2)	0.21148 (10)	0.20357 (8)	0.0427 (4)
O1	0.2105 (2)	0.44007 (10)	0.09705 (9)	0.0604 (5)
H1	0.2133	0.4802	0.0709	0.091*
O2	0.4704 (3)	0.39675 (10)	0.05055 (9)	0.0658 (5)
N3	0.4944 (3)	0.25050 (10)	0.13134 (10)	0.0505 (5)
O3	−0.1197 (3)	0.12701 (11)	1.08533 (9)	0.0725 (5)
N6	0.0253 (3)	0.25962 (11)	0.95482 (10)	0.0515 (5)
N4	0.2420 (2)	0.17006 (10)	0.93228 (9)	0.0426 (4)
C17	0.1698 (3)	0.13594 (13)	0.98605 (10)	0.0416 (5)
N5	0.1530 (3)	0.24561 (11)	0.91340 (10)	0.0542 (5)
C16	0.3809 (3)	0.13618 (13)	0.89167 (10)	0.0427 (5)
C7	0.2327 (3)	0.28716 (12)	0.18016 (10)	0.0387 (4)
C9	0.3516 (3)	0.38637 (12)	0.08889 (11)	0.0438 (5)
C8	0.3532 (3)	0.31110 (12)	0.13320 (10)	0.0407 (4)
C6	0.2526 (3)	0.15587 (12)	0.25486 (10)	0.0406 (4)
C18	0.0303 (3)	0.19342 (12)	0.99957 (10)	0.0397 (4)
C19	−0.1097 (3)	0.18755 (13)	1.04937 (10)	0.0435 (5)
N2	0.4702 (3)	0.18997 (11)	0.17417 (10)	0.0544 (5)
C4	0.0066 (4)	0.07727 (15)	0.30104 (13)	0.0555 (6)
H4A	−0.1262	0.0602	0.2992	0.067*
C3	0.1503 (4)	0.04942 (14)	0.35351 (12)	0.0539 (6)
H3	0.1157	0.0135	0.3871	0.065*
C1	0.3999 (3)	0.12818 (13)	0.30735 (11)	0.0468 (5)
H1A	0.5329	0.1452	0.3096	0.056*
C11	0.5459 (3)	0.18340 (15)	0.88273 (12)	0.0535 (5)
H11	0.5721	0.2350	0.9051	0.064*
C5	0.0549 (3)	0.13048 (14)	0.25048 (11)	0.0495 (5)
H5	−0.0435	0.1487	0.2144	0.059*
C10	0.0630 (3)	0.32936 (14)	0.20576 (12)	0.0515 (5)
H10A	−0.0615	0.3140	0.1770	0.077*
H10B	0.0802	0.3895	0.2044	0.077*
H10C	0.0606	0.3119	0.2524	0.077*
C15	0.3431 (4)	0.05856 (14)	0.86021 (12)	0.0542 (6)
H15	0.2322	0.0268	0.8671	0.065*
C2	0.3460 (4)	0.07454 (14)	0.35661 (12)	0.0528 (5)
H2	0.4441	0.0552	0.3924	0.063*
C13	0.6347 (4)	0.0763 (2)	0.80763 (13)	0.0709 (8)
H13	0.7194	0.0565	0.7784	0.085*
C20	0.2496 (4)	0.05710 (17)	1.02157 (13)	0.0694 (8)
H20A	0.2171	0.0100	0.9909	0.104*
H20B	0.1901	0.0490	1.0621	0.104*
H20C	0.3931	0.0614	1.0346	0.104*
C12	0.6716 (4)	0.1527 (2)	0.83991 (14)	0.0705 (7)
H12	0.7827	0.1843	0.8329	0.085*
C14	0.4724 (4)	0.02880 (17)	0.81842 (12)	0.0644 (7)
H14	0.4496	−0.0237	0.7974	0.077*
O5	0.2055 (3)	0.58080 (13)	0.02879 (12)	0.0749 (6)
H5A	0.290 (5)	0.591 (2)	0.0025 (18)	0.098 (11)*
H5B	0.131 (6)	0.622 (3)	0.0310 (19)	0.111 (13)*

	U11	U22	U33	U12	U13	U23
O4	0.0721 (11)	0.0477 (9)	0.0777 (11)	0.0177 (8)	0.0487 (9)	0.0112 (8)
N1	0.0477 (9)	0.0344 (9)	0.0519 (10)	0.0046 (7)	0.0252 (8)	0.0031 (7)
O1	0.0609 (10)	0.0480 (9)	0.0805 (12)	0.0167 (8)	0.0356 (9)	0.0221 (8)
O2	0.0814 (12)	0.0502 (9)	0.0792 (11)	0.0107 (8)	0.0519 (10)	0.0132 (8)
N3	0.0571 (11)	0.0373 (9)	0.0654 (12)	0.0075 (8)	0.0342 (9)	0.0056 (8)
O3	0.0995 (14)	0.0625 (11)	0.0671 (11)	0.0289 (10)	0.0472 (10)	0.0255 (9)
N6	0.0569 (11)	0.0385 (9)	0.0674 (12)	0.0102 (8)	0.0337 (9)	0.0083 (8)
N4	0.0434 (9)	0.0380 (9)	0.0496 (10)	0.0080 (7)	0.0168 (7)	0.0025 (7)
C17	0.0434 (10)	0.0429 (11)	0.0397 (10)	0.0091 (8)	0.0107 (8)	0.0019 (8)
N5	0.0615 (11)	0.0382 (10)	0.0722 (13)	0.0129 (8)	0.0377 (10)	0.0119 (8)
C16	0.0426 (10)	0.0445 (11)	0.0434 (10)	0.0126 (9)	0.0143 (8)	0.0035 (8)
C7	0.0409 (10)	0.0353 (10)	0.0428 (10)	0.0008 (8)	0.0154 (8)	−0.0040 (8)
C9	0.0457 (11)	0.0377 (10)	0.0518 (12)	0.0008 (9)	0.0193 (9)	−0.0020 (8)
C8	0.0440 (10)	0.0341 (10)	0.0482 (11)	0.0017 (8)	0.0194 (9)	−0.0038 (8)
C6	0.0492 (11)	0.0319 (9)	0.0452 (11)	0.0011 (8)	0.0209 (9)	−0.0006 (8)
C18	0.0414 (10)	0.0377 (10)	0.0415 (10)	0.0045 (8)	0.0115 (8)	0.0006 (8)
C19	0.0514 (11)	0.0403 (11)	0.0414 (11)	0.0072 (9)	0.0155 (9)	0.0002 (8)
N2	0.0628 (12)	0.0400 (10)	0.0702 (12)	0.0116 (8)	0.0394 (10)	0.0097 (8)
C4	0.0495 (12)	0.0546 (13)	0.0659 (15)	−0.0092 (10)	0.0195 (11)	0.0070 (11)
C3	0.0665 (14)	0.0445 (12)	0.0555 (13)	−0.0007 (10)	0.0238 (11)	0.0096 (10)
C1	0.0434 (11)	0.0413 (11)	0.0586 (13)	0.0047 (9)	0.0169 (9)	−0.0021 (9)
C11	0.0489 (12)	0.0584 (13)	0.0560 (13)	0.0021 (10)	0.0169 (10)	−0.0043 (10)
C5	0.0487 (12)	0.0498 (12)	0.0508 (12)	−0.0049 (9)	0.0106 (9)	0.0055 (10)
C10	0.0534 (12)	0.0492 (12)	0.0579 (13)	0.0065 (10)	0.0271 (10)	−0.0006 (10)
C15	0.0613 (13)	0.0449 (12)	0.0584 (14)	0.0085 (10)	0.0157 (11)	−0.0012 (10)
C2	0.0604 (13)	0.0459 (12)	0.0528 (13)	0.0092 (10)	0.0120 (10)	0.0075 (10)
C13	0.0699 (17)	0.090 (2)	0.0589 (15)	0.0279 (15)	0.0283 (13)	−0.0044 (14)
C20	0.0859 (18)	0.0688 (16)	0.0585 (15)	0.0407 (14)	0.0265 (13)	0.0226 (12)
C12	0.0535 (14)	0.091 (2)	0.0744 (17)	0.0013 (13)	0.0306 (12)	−0.0034 (15)
C14	0.0805 (17)	0.0569 (14)	0.0582 (14)	0.0247 (13)	0.0186 (12)	−0.0081 (11)
O5	0.0685 (12)	0.0576 (11)	0.1075 (16)	0.0208 (10)	0.0409 (11)	0.0379 (10)

O4—C19	1.309 (2)	C4—C3	1.362 (3)
O4—H4	0.8200	C4—C5	1.383 (3)
N1—N2	1.352 (2)	C4—H4A	0.9300
N1—C7	1.356 (3)	C3—C2	1.370 (3)
N1—C6	1.440 (2)	C3—H3	0.9300
O1—C9	1.306 (2)	C1—C2	1.382 (3)
O1—H1	0.8200	C1—H1A	0.9300
O2—C9	1.201 (2)	C11—C12	1.381 (3)
N3—N2	1.304 (2)	C11—H11	0.9300
N3—C8	1.357 (2)	C5—H5	0.9300
O3—C19	1.200 (2)	C10—H10A	0.9600
N6—N5	1.300 (2)	C10—H10B	0.9600
N6—C18	1.365 (3)	C10—H10C	0.9600
N4—C17	1.349 (2)	C15—C14	1.378 (3)
N4—N5	1.362 (2)	C15—H15	0.9300
N4—C16	1.434 (2)	C2—H2	0.9300
C17—C18	1.367 (3)	C13—C12	1.370 (4)
C17—C20	1.486 (3)	C13—C14	1.373 (4)
C16—C11	1.376 (3)	C13—H13	0.9300
C16—C15	1.380 (3)	C20—H20A	0.9600
C7—C8	1.382 (3)	C20—H20B	0.9600
C7—C10	1.485 (3)	C20—H20C	0.9600
C9—C8	1.475 (3)	C12—H12	0.9300
C6—C1	1.376 (3)	C14—H14	0.9300
C6—C5	1.381 (3)	O5—H5A	0.85 (4)
C18—C19	1.474 (3)	O5—H5B	0.83 (4)
C19—O4—H4	109.5	C4—C3—H3	120.2
N2—N1—C7	111.55 (15)	C2—C3—H3	120.2
N2—N1—C6	118.32 (15)	C6—C1—C2	118.6 (2)
C7—N1—C6	130.07 (16)	C6—C1—H1A	120.7
C9—O1—H1	109.5	C2—C1—H1A	120.7
N2—N3—C8	109.73 (16)	C16—C11—C12	118.7 (2)
N5—N6—C18	109.01 (16)	C16—C11—H11	120.7
C17—N4—N5	111.38 (15)	C12—C11—H11	120.7
C17—N4—C16	129.99 (17)	C6—C5—C4	118.4 (2)
N5—N4—C16	118.46 (16)	C6—C5—H5	120.8
N4—C17—C18	103.72 (17)	C4—C5—H5	120.8
N4—C17—C20	123.68 (18)	C7—C10—H10A	109.5
C18—C17—C20	132.41 (19)	C7—C10—H10B	109.5
N6—N5—N4	106.70 (16)	H10A—C10—H10B	109.5
C11—C16—C15	121.2 (2)	C7—C10—H10C	109.5
C11—C16—N4	119.10 (19)	H10A—C10—H10C	109.5
C15—C16—N4	119.62 (19)	H10B—C10—H10C	109.5
N1—C7—C8	103.45 (16)	C14—C15—C16	119.0 (2)
N1—C7—C10	123.88 (17)	C14—C15—H15	120.5
C8—C7—C10	132.61 (18)	C16—C15—H15	120.5
O2—C9—O1	124.44 (19)	C3—C2—C1	120.9 (2)
O2—C9—C8	122.83 (18)	C3—C2—H2	119.6
O1—C9—C8	112.72 (17)	C1—C2—H2	119.6
N3—C8—C7	108.59 (17)	C12—C13—C14	120.0 (2)
N3—C8—C9	119.39 (17)	C12—C13—H13	120.0
C7—C8—C9	132.02 (17)	C14—C13—H13	120.0
C1—C6—C5	121.31 (19)	C17—C20—H20A	109.5
C1—C6—N1	118.25 (18)	C17—C20—H20B	109.5
C5—C6—N1	120.44 (19)	H20A—C20—H20B	109.5
N6—C18—C17	109.19 (17)	C17—C20—H20C	109.5
N6—C18—C19	121.87 (17)	H20A—C20—H20C	109.5
C17—C18—C19	128.80 (18)	H20B—C20—H20C	109.5
O3—C19—O4	124.27 (19)	C13—C12—C11	120.7 (3)
O3—C19—C18	123.24 (18)	C13—C12—H12	119.6
O4—C19—C18	112.46 (17)	C11—C12—H12	119.6
N3—N2—N1	106.67 (15)	C13—C14—C15	120.4 (2)
C3—C4—C5	121.1 (2)	C13—C14—H14	119.8
C3—C4—H4A	119.4	C15—C14—H14	119.8
C5—C4—H4A	119.4	H5A—O5—H5B	112 (3)
C4—C3—C2	119.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N3i	0.82	1.89	2.704 (2)	170
O1—H1···O5	0.82	1.79	2.599 (2)	168
O5—H5A···O2ii	0.85 (4)	2.07 (4)	2.914 (3)	171 (3)
O5—H5B···N6iii	0.83 (4)	2.20 (4)	3.015 (3)	171 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯N3i	0.82	1.89	2.704 (2)	170
O1—H1⋯O5	0.82	1.79	2.599 (2)	168
O5—H5A⋯O2ii	0.85 (4)	2.07 (4)	2.914 (3)	171 (3)
O5—H5B⋯N6iii	0.83 (4)	2.20 (4)	3.015 (3)	171 (4)

Symmetry codes: (i) ; (ii) ; (iii) .