3,4,5-Trimethyl-1,2,4-triazole trihydrate

The title compound, C₅H₉N₃·3H₂O, features an extensive network of hydrogen bonding, but is otherwise unexceptional. The structure was determined from data collected on a non-merohedrally twinned crystal.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.049
• wR factor = 0.149
• Data-to-parameter ratio = 41.7

checkCIF/PLATON results

No syntax errors found



Datablock: 05adb19m



Alert level A
REFLT03_ALERT_3_A  Reflection count > 15% excess reflns - sys abs data present?
           From the CIF: _diffrn_reflns_theta_max           30.68
           From the CIF: _diffrn_reflns_theta_full          30.68
           From the CIF: _reflns_number_total               5341
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2765
           Completeness (_total/calc)            193.16%

Author Response: The crystal under investigation was non-merohedrally twinned with a BASF value of 0.1344(5) and the hklf 5 procedure was used for the refinement (see _exptl_special_details for details). The data were integrated using TWINSAINT, equivalent reflections were merged in TWINABS, and all reflections having at least one contribution from the major component had been used for the hklf 5 refinement. Due to "twin pairing errors" (equivalent reflections being counted as overlapping for one reflection, but as not overlaped for an eqivalent one) the merging in TWINABS is incomplete, thus resulting in too many independent reflections.

Alert level B
PLAT021_ALERT_1_B Ratio Unique / Expected Reflections too High ...       1.93

Author Response: The crystal under investigation was non-merohedrally twinned with a BASF value of 0.1344(5) and the hklf 5 procedure was used for the refinement (see _exptl_special_details for details). The data were integrated using TWINSAINT, equivalent reflections were merged in TWINABS, and all reflections having at least one contribution from the major component had been used for the hklf 5 refinement. Due to "twin pairing errors" (equivalent reflections being counted as overlapping for one reflection, but as not overlaped for an eqivalent one) the merging in TWINABS is incomplete, thus resulting in too many independent reflections.

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   0 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
   1 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, 2003); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and publCIF (Westrip, 2007).

3,4,5-Trimethyl-1,2,4-triazole trihydrate

Crystal data

C5H9N3·3H2O	F(000) = 360
Mr = 165.2	Dx = 1.233 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7270 reflections
a = 10.0587 (4) Å	θ = 2.6–30.7°
b = 6.5923 (2) Å	µ = 0.1 mm^−1
c = 13.4209 (5) Å	T = 100 K
β = 91.183 (1)°	Block, colourless
V = 889.75 (6) Å^3	0.38 × 0.36 × 0.23 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer	3958 reflections with I > 2σ(I)
ω scans	Rint = 0
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003)	θmax = 30.7°, θmin = 2.5°
Tmin = 0.966, Tmax = 0.977	h = −14→14
17695 measured reflections	k = 0→9
5341 independent reflections	l = 0→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.049	w = 1/[σ^2(Fo^2) + (0.1015P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.149	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.48 e Å^−3
5341 reflections	Δρmin = −0.39 e Å^−3
128 parameters

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.

Refinement. The crystals under investigation were found to be non-merohedrally twinned. A crystal with only two well defined twin components was selected for the data collection and its two components were identified using the program GEMINI (Sparks, 1999), integrated using SAINT-Plus (Bruker, 2003) and merged and corrected for absorption using TWINABS (Bruker, 2003). 7284 data (2281 unique) involved component 1 only (mean I/σ 19.0), 7155 data (2243 unique) involved component 2 only (mean I/σ 7.4), and 3256 data (1230 unique) involved both components (mean I/σ 19.5). The structure was solved using the reflections of only component 1 using direct methods and was refined with reflections containing at least one contribution of component 1 using the hklf 5 method. The twin operation involves a 180 degree rotation, and the twin matrix was found to be 0.28746 0.00210 - 0.71298, 0.00195 - 0.99981 - 0.00024, -1.28592 - 0.00555 - 0.28824. The BASF factor refined to 0.1350 (6).

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

	x	y	z	Uiso*/Ueq
N1	0.63048 (7)	0.15687 (10)	0.23095 (5)	0.01905 (16)
N2	0.73510 (7)	0.15563 (10)	0.16438 (5)	0.02019 (16)
C3	0.84600 (8)	0.15397 (11)	0.21729 (6)	0.01866 (17)
N4	0.81871 (6)	0.15437 (10)	0.31612 (5)	0.01783 (16)
C5	0.68335 (8)	0.15592 (11)	0.32118 (6)	0.01763 (17)
C6	0.98224 (9)	0.15140 (13)	0.17707 (7)	0.0261 (2)
H6A	0.9771	0.1462	0.1041	0.031*
H6B	1.03	0.0318	0.2023	0.031*
H6C	1.0297	0.2745	0.1982	0.031*
C7	0.91311 (9)	0.15041 (14)	0.39952 (7)	0.0280 (2)
H7A	0.8925	0.0363	0.4434	0.034*
H7B	0.9072	0.2777	0.4369	0.034*
H7C	1.0034	0.1346	0.3745	0.034*
C8	0.61061 (9)	0.15678 (13)	0.41608 (6)	0.02398 (19)
H8A	0.5147	0.1509	0.4018	0.029*
H8B	0.6316	0.2813	0.4531	0.029*
H8C	0.6374	0.0388	0.4561	0.029*
O1	0.76661 (7)	0.44373 (11)	0.85164 (5)	0.02738 (16)
O2	0.63598 (6)	0.81171 (9)	0.83098 (5)	0.02416 (16)
O3	0.72608 (8)	0.09621 (11)	0.95808 (5)	0.03501 (19)
H1A	0.7994 (13)	0.406 (2)	0.7918 (11)	0.052 (4)*
H1B	0.7267 (13)	0.546 (2)	0.8390 (10)	0.048 (4)*
H2A	0.5460 (13)	0.8271 (17)	0.8170 (9)	0.041 (3)*
H2B	0.6582 (11)	0.9033 (18)	0.8786 (9)	0.033 (3)*
H3A	0.7407 (13)	0.221 (2)	0.9294 (9)	0.053 (4)*
H3B	0.7076 (17)	0.118 (2)	1.0237 (14)	0.081 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0195 (3)	0.0203 (3)	0.0174 (3)	−0.0005 (2)	−0.0002 (2)	0.0010 (2)
N2	0.0230 (4)	0.0212 (3)	0.0164 (3)	−0.0001 (2)	0.0008 (3)	0.0009 (2)
C3	0.0216 (4)	0.0160 (3)	0.0184 (4)	−0.0012 (3)	0.0016 (3)	0.0005 (3)
N4	0.0178 (3)	0.0187 (3)	0.0170 (3)	−0.0004 (2)	−0.0012 (2)	−0.0005 (2)
C5	0.0184 (4)	0.0166 (3)	0.0179 (4)	−0.0003 (3)	−0.0001 (3)	−0.0001 (3)
C6	0.0227 (4)	0.0279 (4)	0.0278 (4)	−0.0007 (3)	0.0058 (3)	−0.0002 (3)
C7	0.0231 (4)	0.0393 (5)	0.0213 (4)	0.0022 (3)	−0.0063 (3)	−0.0028 (3)
C8	0.0242 (4)	0.0292 (4)	0.0187 (4)	−0.0007 (3)	0.0030 (3)	0.0009 (3)
O1	0.0315 (3)	0.0277 (3)	0.0230 (3)	0.0034 (3)	0.0016 (2)	0.0033 (2)
O2	0.0228 (3)	0.0258 (3)	0.0238 (3)	0.0013 (2)	−0.0032 (2)	−0.0035 (2)
O3	0.0596 (5)	0.0273 (4)	0.0179 (3)	−0.0080 (3)	−0.0035 (3)	−0.0004 (3)

Geometric parameters (Å, º)

N1—C5	1.3125 (11)	C7—H7B	0.98
N1—N2	1.3945 (9)	C7—H7C	0.98
N2—C3	1.3098 (11)	C8—H8A	0.98
C3—N4	1.3601 (10)	C8—H8B	0.98
C3—C6	1.4833 (11)	C8—H8C	0.98
N4—C5	1.3646 (10)	O1—H1A	0.908 (14)
N4—C7	1.4530 (11)	O1—H1B	0.800 (15)
C5—C8	1.4819 (11)	O2—H2A	0.926 (14)
C6—H6A	0.98	O2—H2B	0.904 (13)
C6—H6B	0.98	O3—H3A	0.923 (15)
C6—H6C	0.98	O3—H3B	0.915 (18)
C7—H7A	0.98
C5—N1—N2	107.12 (7)	H6B—C6—H6C	109.5
C3—N2—N1	107.35 (7)	N4—C7—H7A	109.5
N2—C3—N4	109.99 (7)	N4—C7—H7B	109.5
N2—C3—C6	125.85 (7)	H7A—C7—H7B	109.5
N4—C3—C6	124.16 (8)	N4—C7—H7C	109.5
C3—N4—C5	105.68 (7)	H7A—C7—H7C	109.5
C3—N4—C7	127.54 (7)	H7B—C7—H7C	109.5
C5—N4—C7	126.77 (7)	C5—C8—H8A	109.5
N1—C5—N4	109.86 (7)	C5—C8—H8B	109.5
N1—C5—C8	126.52 (7)	H8A—C8—H8B	109.5
N4—C5—C8	123.62 (7)	C5—C8—H8C	109.5
C3—C6—H6A	109.5	H8A—C8—H8C	109.5
C3—C6—H6B	109.5	H8B—C8—H8C	109.5
H6A—C6—H6B	109.5	H1A—O1—H1B	103.3 (12)
C3—C6—H6C	109.5	H2A—O2—H2B	107.2 (10)
H6A—C6—H6C	109.5	H3A—O3—H3B	107.3 (12)
C5—N1—N2—C3	0.00 (8)	N2—N1—C5—N4	0.08 (8)
N1—N2—C3—N4	−0.09 (8)	N2—N1—C5—C8	179.96 (7)
N1—N2—C3—C6	179.74 (7)	C3—N4—C5—N1	−0.13 (8)
N2—C3—N4—C5	0.13 (8)	C7—N4—C5—N1	−179.17 (7)
C6—C3—N4—C5	−179.70 (7)	C3—N4—C5—C8	179.98 (7)
N2—C3—N4—C7	179.17 (7)	C7—N4—C5—C8	0.94 (12)
C6—C3—N4—C7	−0.66 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O3^i	0.904 (13)	1.786 (13)	2.6804 (9)	169.6 (10)
O3—H3A···O1	0.923 (15)	1.822 (14)	2.7349 (10)	169.7 (12)
O2—H2A···N1^ii	0.926 (14)	1.878 (14)	2.7974 (10)	171.2 (11)
O1—H1A···O2^iii	0.908 (14)	1.890 (15)	2.7971 (9)	176.4 (13)
O3—H3B···N2^iv	0.915 (18)	1.92 (2)	2.7959 (10)	159.9 (16)
O1—H1B···O2	0.800 (15)	1.978 (15)	2.7700 (9)	170.3 (14)

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