Crystal structure of 1-anilino-5-methyl-1H-1,2,3-triazole-4-carb­oxy­lic acid monohydrate

The water mol­ecule connects the mol­ecules in the crystal packing. The crystal structure exhibits N—H...O, O—H...O and O—H...N inter­actions, resulting in the formation of a three-dimensional framework.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.100
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.498 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT300_ALERT_4_G Atom Site Occupancy of H10A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H10B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H10C       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H10D       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H10E       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H10F       Constrained at        0.5 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by .          1 Units

   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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Bruker, 2004); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

1-Anilino-5-methyl-1H-1,2,3-triazole-4-carboxylic acid monohydrate

Crystal data

C10H10N4O2·H2O	F(000) = 496
Mr = 236.24	Dx = 1.345 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.2288 (14) Å	Cell parameters from 11378 reflections
b = 6.8265 (14) Å	θ = 3.1–25.2°
c = 23.922 (5) Å	µ = 0.10 mm^−1
β = 98.69 (3)°	T = 298 K
V = 1167.0 (4) Å^3	Block, colourless
Z = 4	0.24 × 0.20 × 0.06 mm

Data collection

Bruker KappaCCD diffractometer	2207 independent reflections
Horizonally mounted graphite crystal monochromator	1559 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm^-1	Rint = 0.042
CCD scans	θmax = 25.7°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −8→8
Tmin = 0.701, Tmax = 0.745	k = −8→7
11378 measured reflections	l = −28→29

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)] = 0.041	w = 1/[σ^2(Fo^2) + (0.0451P)^2 + 0.2317P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.100	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.18 e Å^−3
2207 reflections	Δρmin = −0.15 e Å^−3
191 parameters	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.016 (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	Occ. (<1)
N1	0.1134 (2)	0.5773 (2)	0.07579 (6)	0.0470 (4)
N2	0.1952 (2)	0.4253 (2)	0.10201 (7)	0.0490 (4)
N3	0.0553 (2)	0.3016 (2)	0.11042 (6)	0.0408 (4)
N4	0.0956 (2)	0.1211 (2)	0.13675 (6)	0.0456 (4)
O1	−0.11452 (18)	0.8386 (2)	0.01606 (6)	0.0548 (4)
O2	−0.37050 (18)	0.6983 (2)	0.03987 (6)	0.0626 (4)
C1	−0.2030 (3)	0.7017 (3)	0.04017 (7)	0.0416 (4)
C2	−0.0763 (2)	0.5512 (3)	0.06831 (7)	0.0379 (4)
C3	−0.1165 (2)	0.3727 (2)	0.09034 (7)	0.0375 (4)
C4	0.1777 (2)	0.1351 (2)	0.19481 (7)	0.0387 (4)
C5	0.3163 (3)	0.0044 (3)	0.21538 (9)	0.0536 (5)
C6	0.3937 (3)	0.0088 (3)	0.27196 (9)	0.0608 (6)
C7	0.3320 (3)	0.1427 (3)	0.30781 (9)	0.0552 (6)
C8	0.1928 (3)	0.2721 (3)	0.28731 (9)	0.0575 (5)
C9	0.1139 (3)	0.2681 (3)	0.23076 (8)	0.0502 (5)
C10	−0.2922 (3)	0.2638 (3)	0.09330 (8)	0.0507 (5)
H10A	−0.397146	0.341238	0.076648	0.076*	0.5
H10B	−0.290788	0.142584	0.073046	0.076*	0.5
H10C	−0.302575	0.237247	0.132110	0.076*	0.5
H10D	−0.263193	0.139474	0.111221	0.076*	0.5
H10E	−0.369552	0.338129	0.114823	0.076*	0.5
H10F	−0.357764	0.243466	0.055760	0.076*	0.5
O1W	0.3100 (2)	0.9111 (2)	0.05054 (6)	0.0509 (4)
H1	−0.199 (3)	0.926 (4)	−0.0049 (10)	0.081 (7)*
H9	0.022 (3)	0.353 (3)	0.2172 (8)	0.058 (6)*
H5	0.359 (3)	−0.091 (3)	0.1907 (9)	0.067 (6)*
H6	0.495 (3)	−0.078 (3)	0.2851 (9)	0.076 (7)*
H7	0.388 (3)	0.149 (3)	0.3456 (10)	0.067 (6)*
H8	0.139 (3)	0.367 (4)	0.3125 (10)	0.083 (7)*
H4	0.170 (3)	0.056 (3)	0.1157 (9)	0.063 (6)*
H1WA	0.415 (4)	0.876 (4)	0.0455 (10)	0.074 (8)*
H1WB	0.241 (4)	0.800 (4)	0.0552 (10)	0.089 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0395 (9)	0.0483 (9)	0.0530 (9)	0.0066 (7)	0.0060 (7)	0.0148 (8)
N2	0.0410 (9)	0.0486 (9)	0.0570 (10)	0.0059 (8)	0.0067 (7)	0.0150 (8)
N3	0.0423 (9)	0.0390 (8)	0.0404 (8)	0.0054 (7)	0.0043 (6)	0.0064 (7)
N4	0.0573 (10)	0.0355 (9)	0.0431 (9)	0.0114 (7)	0.0046 (7)	0.0046 (7)
O1	0.0467 (8)	0.0527 (8)	0.0641 (9)	0.0101 (7)	0.0057 (7)	0.0233 (7)
O2	0.0394 (8)	0.0704 (10)	0.0785 (10)	0.0141 (7)	0.0102 (7)	0.0187 (8)
C1	0.0426 (11)	0.0450 (11)	0.0374 (9)	0.0082 (9)	0.0068 (8)	0.0011 (8)
C2	0.0361 (10)	0.0419 (10)	0.0355 (9)	0.0054 (8)	0.0051 (7)	0.0020 (8)
C3	0.0407 (10)	0.0403 (10)	0.0313 (9)	0.0053 (8)	0.0053 (7)	−0.0019 (8)
C4	0.0390 (10)	0.0348 (9)	0.0428 (10)	0.0029 (8)	0.0080 (8)	0.0070 (8)
C5	0.0580 (13)	0.0519 (12)	0.0522 (12)	0.0201 (10)	0.0129 (10)	0.0078 (10)
C6	0.0533 (13)	0.0678 (15)	0.0594 (14)	0.0172 (11)	0.0027 (10)	0.0192 (12)
C7	0.0569 (13)	0.0638 (14)	0.0433 (11)	−0.0076 (11)	0.0022 (10)	0.0109 (11)
C8	0.0658 (14)	0.0566 (13)	0.0506 (12)	0.0041 (11)	0.0107 (10)	−0.0039 (11)
C9	0.0498 (12)	0.0487 (12)	0.0512 (12)	0.0146 (10)	0.0045 (9)	0.0020 (10)
C10	0.0478 (11)	0.0478 (11)	0.0557 (12)	−0.0048 (9)	0.0053 (9)	−0.0045 (9)
O1W	0.0430 (9)	0.0445 (8)	0.0649 (9)	0.0073 (7)	0.0074 (7)	0.0108 (7)

Geometric parameters (Å, º)

N1—N2	1.307 (2)	C5—H5	0.96 (2)
N1—C2	1.367 (2)	C6—C7	1.373 (3)
N2—N3	1.356 (2)	C6—H6	0.96 (2)
N3—C3	1.352 (2)	C7—C8	1.372 (3)
N3—N4	1.394 (2)	C7—H7	0.93 (2)
N4—C4	1.429 (2)	C8—C9	1.387 (3)
N4—H4	0.91 (2)	C8—H8	1.00 (2)
O1—C1	1.314 (2)	C9—H9	0.90 (2)
O1—H1	0.94 (2)	C10—H10A	0.9600
O2—C1	1.210 (2)	C10—H10B	0.9600
C1—C2	1.470 (2)	C10—H10C	0.9600
C2—C3	1.376 (2)	C10—H10D	0.9600
C3—C10	1.482 (2)	C10—H10E	0.9600
C4—C5	1.376 (3)	C10—H10F	0.9600
C4—C9	1.377 (3)	O1W—H1WA	0.82 (3)
C5—C6	1.385 (3)	O1W—H1WB	0.92 (3)
N2—N1—C2	109.36 (14)	C6—C7—H7	120.2 (13)
N1—N2—N3	105.80 (14)	C7—C8—C9	120.5 (2)
C3—N3—N2	112.91 (14)	C7—C8—H8	122.1 (13)
C3—N3—N4	126.55 (15)	C9—C8—H8	117.3 (14)
N2—N3—N4	120.53 (14)	C4—C9—C8	119.66 (19)
N3—N4—C4	114.07 (14)	C4—C9—H9	119.7 (13)
N3—N4—H4	106.5 (13)	C8—C9—H9	120.6 (13)
C4—N4—H4	112.3 (14)	C3—C10—H10A	109.5
C1—O1—H1	111.4 (14)	C3—C10—H10B	109.5
O2—C1—O1	124.32 (17)	H10A—C10—H10B	109.5
O2—C1—C2	122.91 (17)	C3—C10—H10C	109.5
O1—C1—C2	112.77 (15)	H10A—C10—H10C	109.5
N1—C2—C3	109.33 (15)	H10B—C10—H10C	109.5
N1—C2—C1	120.80 (15)	C3—C10—H10D	109.5
C3—C2—C1	129.87 (16)	H10A—C10—H10D	141.1
N3—C3—C2	102.58 (14)	H10B—C10—H10D	56.3
N3—C3—C10	123.43 (16)	H10C—C10—H10D	56.3
C2—C3—C10	133.97 (16)	C3—C10—H10E	109.5
C5—C4—C9	119.92 (18)	H10A—C10—H10E	56.3
C5—C4—N4	118.51 (16)	H10B—C10—H10E	141.1
C9—C4—N4	121.46 (16)	H10C—C10—H10E	56.3
C4—C5—C6	120.0 (2)	H10D—C10—H10E	109.5
C4—C5—H5	120.3 (13)	C3—C10—H10F	109.5
C6—C5—H5	119.7 (13)	H10A—C10—H10F	56.3
C7—C6—C5	120.3 (2)	H10B—C10—H10F	56.3
C7—C6—H6	120.8 (13)	H10C—C10—H10F	141.1
C5—C6—H6	118.8 (13)	H10D—C10—H10F	109.5
C8—C7—C6	119.7 (2)	H10E—C10—H10F	109.5
C8—C7—H7	120.1 (13)	H1WA—O1W—H1WB	108 (2)
C2—N1—N2—N3	0.73 (19)	N1—C2—C3—N3	0.32 (18)
N1—N2—N3—C3	−0.55 (19)	C1—C2—C3—N3	−179.89 (16)
N1—N2—N3—N4	178.75 (14)	N1—C2—C3—C10	−178.06 (18)
C3—N3—N4—C4	−114.38 (18)	C1—C2—C3—C10	1.7 (3)
N2—N3—N4—C4	66.4 (2)	N3—N4—C4—C5	−141.88 (17)
N2—N1—C2—C3	−0.69 (19)	N3—N4—C4—C9	41.9 (2)
N2—N1—C2—C1	179.51 (15)	C9—C4—C5—C6	−1.1 (3)
O2—C1—C2—N1	−168.96 (17)	N4—C4—C5—C6	−177.43 (18)
O1—C1—C2—N1	10.7 (2)	C4—C5—C6—C7	0.3 (3)
O2—C1—C2—C3	11.3 (3)	C5—C6—C7—C8	0.1 (3)
O1—C1—C2—C3	−169.10 (17)	C6—C7—C8—C9	0.2 (3)
N2—N3—C3—C2	0.13 (18)	C5—C4—C9—C8	1.4 (3)
N4—N3—C3—C2	−179.11 (15)	N4—C4—C9—C8	177.62 (18)
N2—N3—C3—C10	178.74 (15)	C7—C8—C9—C4	−1.0 (3)
N4—N3—C3—C10	−0.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1W^i	0.94 (2)	1.68 (3)	2.6030 (19)	167 (2)
N4—H4···O1W^ii	0.91 (2)	2.22 (2)	3.111 (2)	169.2 (19)
O1W—H1WA···O2^iii	0.82 (3)	1.99 (3)	2.773 (2)	159 (2)
O1W—H1WB···N1	0.92 (3)	1.88 (3)	2.800 (2)	172 (2)

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