Synthesis, crystal structure at 219 K and Hirshfeld surface analyses of 1,4,6-tri­methyl­quinoxaline-2,3(1H,4H)-dione monohydrate

The asymmetric unit of the title compound, C₁₁H₁₂N₂O₂·H₂O, contains a disordered mol­ecule of 1,4,6-trimethyl-1,4-di­hydro-quinoxaline-2,3-dione and a solvent water mol­ecule. In the crystal, mol­ecules are linked by O—H...O and C—H...O hydrogen bonds into layers lying parallel to (10). The Hirshfeld surface analysis is carried out.

Key indicators

• Single-crystal X-ray study
• T = 219 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.067
• wR factor = 0.147
• Data-to-parameter ratio = 9.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.63 Note
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0045 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      8.305 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.182 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.598         17 Report
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          5 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        33% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          6 Note
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              H2 O
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         30 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        54% Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   9 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2020); software used to prepare material for publication: WinGX (Farrugia, 2012), PLATON (Spek, 2020) and publCIF (Westrip, 2010).

1,4,6-Trimethylquinoxaline-2,3(1H,4H)-dione monohydrate

Crystal data

C11H12N2O2·H2O	F(000) = 472
Mr = 222.24	Dx = 1.363 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.0695 (4) Å	Cell parameters from 7373 reflections
b = 10.8321 (5) Å	θ = 2.4–24.7°
c = 14.4349 (6) Å	µ = 0.10 mm^−1
β = 101.556 (3)°	T = 219 K
V = 1082.98 (9) Å^3	Parallelepiped, yellow
Z = 4	0.30 × 0.18 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer	1563 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.062
φ and ω scans	θmax = 25.2°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −8→8
	k = −12→12
32798 measured reflections	l = −17→17
1935 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.067	H-atom parameters constrained
wR(F^2) = 0.147	w = 1/[σ^2(Fo^2) + (0.0097P)^2 + 1.8308P] where P = (Fo^2 + 2Fc^2)/3
S = 1.24	(Δ/σ)max < 0.001
1935 reflections	Δρmax = 0.21 e Å^−3
201 parameters	Δρmin = −0.18 e Å^−3
30 restraints	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (9)

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)
O1	0.3712 (4)	1.3409 (2)	0.00205 (17)	0.0479 (7)
O2	0.3853 (4)	1.2710 (3)	0.18106 (17)	0.0581 (8)
C1	0.2612 (4)	0.9861 (3)	0.0618 (3)	0.0409 (8)
C2A	0.2177 (14)	0.8598 (10)	0.0725 (6)	0.034 (2)	0.706 (7)
H2A	0.219201	0.830335	0.133895	0.041*	0.706 (7)
C2B	0.228 (5)	0.879 (3)	0.1074 (16)	0.048 (7)	0.294 (7)
H2B	0.237848	0.867991	0.172811	0.057*	0.294 (7)
C3A	0.1723 (13)	0.7756 (12)	−0.0031 (7)	0.037 (2)	0.706 (7)
C3B	0.175 (4)	0.788 (3)	0.0367 (16)	0.037 (5)	0.294 (7)
H3B	0.152151	0.706837	0.055446	0.045*	0.294 (7)
C4A	0.1703 (14)	0.8174 (10)	−0.0933 (6)	0.038 (2)	0.706 (7)
H4A	0.142000	0.761812	−0.144148	0.045*	0.706 (7)
C4B	0.156 (3)	0.811 (2)	−0.0554 (16)	0.035 (6)	0.294 (7)
C5A	0.210 (2)	0.9418 (16)	−0.1111 (9)	0.039 (3)	0.706 (7)
H5A	0.207157	0.970180	−0.172834	0.047*	0.706 (7)
C5B	0.193 (5)	0.923 (4)	−0.087 (2)	0.032 (6)	0.294 (7)
H5B	0.176018	0.933494	−0.153049	0.038*	0.294 (7)
C6	0.2535 (4)	1.0233 (3)	−0.0314 (2)	0.0369 (8)
N1	0.2915 (4)	1.1465 (2)	−0.05089 (18)	0.0359 (7)
C9	0.3382 (4)	1.2324 (3)	0.0177 (2)	0.0354 (7)
C10	0.3472 (5)	1.1936 (3)	0.1182 (2)	0.0402 (8)
N2	0.3101 (4)	1.0729 (3)	0.1354 (2)	0.0440 (7)
C8	0.2761 (6)	1.1869 (4)	−0.1493 (2)	0.0540 (10)
H8A	0.223018	1.120497	−0.191729	0.081*	0.22 (4)
H8B	0.403194	1.208575	−0.159941	0.081*	0.22 (4)
H8C	0.191973	1.258317	−0.161254	0.081*	0.22 (4)
H8D	0.322439	1.271095	−0.150220	0.081*	0.78 (4)
H8E	0.142263	1.183017	−0.182009	0.081*	0.78 (4)
H8F	0.353484	1.133275	−0.180695	0.081*	0.78 (4)
C11	0.3169 (7)	1.0381 (4)	0.2335 (3)	0.0696 (13)
H11A	0.279949	0.952205	0.236449	0.104*	0.24 (5)
H11B	0.228285	1.089532	0.259797	0.104*	0.24 (5)
H11C	0.446948	1.049549	0.269709	0.104*	0.24 (5)
H11D	0.356839	1.108652	0.274187	0.104*	0.76 (5)
H11E	0.408503	0.971326	0.250839	0.104*	0.76 (5)
H11F	0.189839	1.011308	0.240928	0.104*	0.76 (5)
O3	0.3982 (6)	1.4989 (3)	−0.1600 (2)	0.0833 (11)
H3A	0.382975	1.460410	−0.109907	0.125*
H3C	0.477462	1.559146	−0.144450	0.125*
C7A	0.1315 (8)	0.6428 (5)	0.0165 (4)	0.0528 (17)	0.706 (7)
H7A2	0.035271	0.639039	0.055782	0.079*	0.706 (7)
H7A3	0.249382	0.603381	0.049019	0.079*	0.706 (7)
H7A1	0.083495	0.600399	−0.042761	0.079*	0.706 (7)
C7B	0.0926 (19)	0.7135 (13)	−0.1317 (10)	0.062 (5)	0.294 (7)
H7B1	0.025634	0.753011	−0.189272	0.093*	0.294 (7)
H7B2	0.006626	0.655227	−0.110056	0.093*	0.294 (7)
H7B3	0.205065	0.670198	−0.143967	0.093*	0.294 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0528 (15)	0.0419 (15)	0.0475 (14)	−0.0027 (12)	0.0067 (11)	0.0004 (12)
O2	0.0675 (18)	0.0632 (18)	0.0414 (14)	−0.0097 (14)	0.0057 (12)	−0.0075 (14)
C1	0.0219 (15)	0.0408 (19)	0.059 (2)	0.0014 (14)	0.0050 (14)	0.0022 (17)
C2A	0.026 (3)	0.038 (6)	0.038 (5)	0.003 (3)	0.007 (4)	0.000 (5)
C2B	0.051 (9)	0.040 (10)	0.051 (13)	−0.009 (7)	0.008 (11)	−0.016 (11)
C3A	0.029 (3)	0.039 (5)	0.043 (8)	−0.003 (3)	0.006 (5)	−0.005 (6)
C3B	0.040 (8)	0.034 (10)	0.036 (13)	0.003 (7)	0.003 (10)	−0.004 (11)
C4A	0.035 (3)	0.039 (4)	0.037 (5)	0.003 (2)	0.002 (4)	−0.005 (4)
C4B	0.033 (7)	0.042 (11)	0.029 (14)	−0.002 (7)	0.008 (10)	−0.013 (11)
C5A	0.038 (5)	0.038 (5)	0.039 (6)	−0.002 (4)	0.002 (4)	0.006 (4)
C5B	0.014 (7)	0.042 (14)	0.038 (13)	0.005 (7)	0.003 (8)	0.005 (10)
C6	0.0200 (15)	0.0367 (18)	0.050 (2)	0.0025 (13)	−0.0020 (13)	−0.0011 (15)
N1	0.0297 (14)	0.0393 (15)	0.0358 (15)	0.0005 (12)	−0.0002 (11)	−0.0006 (12)
C9	0.0259 (16)	0.0385 (19)	0.0407 (18)	0.0022 (14)	0.0037 (13)	−0.0001 (15)
C10	0.0318 (17)	0.052 (2)	0.0362 (18)	−0.0002 (15)	0.0048 (14)	−0.0006 (16)
N2	0.0360 (15)	0.0523 (18)	0.0448 (17)	0.0004 (14)	0.0108 (13)	0.0091 (14)
C8	0.063 (3)	0.057 (2)	0.037 (2)	0.002 (2)	−0.0016 (17)	0.0010 (17)
C11	0.081 (3)	0.078 (3)	0.054 (3)	0.002 (3)	0.023 (2)	0.017 (2)
O3	0.127 (3)	0.069 (2)	0.0480 (17)	−0.041 (2)	0.0053 (18)	0.0030 (16)
C7A	0.055 (3)	0.041 (3)	0.063 (4)	−0.001 (2)	0.013 (3)	0.002 (3)
C7B	0.048 (8)	0.063 (9)	0.077 (10)	−0.005 (7)	0.014 (7)	−0.045 (8)

Geometric parameters (Å, º)

O1—C9	1.228 (4)	N1—C8	1.470 (4)
O2—C10	1.226 (4)	C9—C10	1.499 (5)
C1—C2B	1.38 (3)	C10—N2	1.365 (5)
C1—C6	1.394 (5)	N2—C11	1.458 (5)
C1—N2	1.409 (4)	C8—H8A	0.9700
C1—C2A	1.418 (12)	C8—H8B	0.9700
C2A—C3A	1.409 (11)	C8—H8C	0.9700
C2A—H2A	0.9400	C8—H8D	0.9700
C2B—C3B	1.41 (2)	C8—H8E	0.9700
C2B—H2B	0.9400	C8—H8F	0.9700
C3A—C4A	1.375 (11)	C11—H11A	0.9700
C3A—C7A	1.504 (14)	C11—H11B	0.9700
C3B—C4B	1.34 (3)	C11—H11C	0.9700
C3B—H3B	0.9400	C11—H11D	0.9700
C4A—C5A	1.41 (2)	C11—H11E	0.9700
C4A—H4A	0.9400	C11—H11F	0.9700
C4B—C5B	1.34 (4)	O3—H3A	0.8603
C4B—C7B	1.53 (2)	O3—H3C	0.8598
C5A—C6	1.434 (17)	C7A—H7A2	0.9700
C5A—H5A	0.9400	C7A—H7A3	0.9700
C5B—C6	1.37 (4)	C7A—H7A1	0.9700
C5B—H5B	0.9400	C7B—H7B1	0.9700
C6—N1	1.401 (4)	C7B—H7B2	0.9700
N1—C9	1.351 (4)	C7B—H7B3	0.9700
C2B—C1—C6	136.5 (10)	H8B—C8—H8C	109.5
C2B—C1—N2	104.1 (10)	N1—C8—H8D	109.5
C6—C1—N2	119.4 (3)	H8A—C8—H8D	141.1
C6—C1—C2A	114.6 (5)	H8B—C8—H8D	56.3
N2—C1—C2A	126.0 (5)	H8C—C8—H8D	56.3
C3A—C2A—C1	124.1 (8)	N1—C8—H8E	109.5
C3A—C2A—H2A	117.9	H8A—C8—H8E	56.3
C1—C2A—H2A	117.9	H8B—C8—H8E	141.1
C1—C2B—C3B	107 (2)	H8C—C8—H8E	56.3
C1—C2B—H2B	126.6	H8D—C8—H8E	109.5
C3B—C2B—H2B	126.6	N1—C8—H8F	109.5
C4A—C3A—C2A	118.5 (11)	H8A—C8—H8F	56.3
C4A—C3A—C7A	121.8 (10)	H8B—C8—H8F	56.3
C2A—C3A—C7A	119.7 (9)	H8C—C8—H8F	141.1
C4B—C3B—C2B	123 (3)	H8D—C8—H8F	109.5
C4B—C3B—H3B	118.5	H8E—C8—H8F	109.5
C2B—C3B—H3B	118.5	N2—C11—H11A	109.5
C3A—C4A—C5A	121.5 (11)	N2—C11—H11B	109.5
C3A—C4A—H4A	119.2	H11A—C11—H11B	109.5
C5A—C4A—H4A	119.2	N2—C11—H11C	109.5
C3B—C4B—C5B	122 (3)	H11A—C11—H11C	109.5
C3B—C4B—C7B	123 (2)	H11B—C11—H11C	109.5
C5B—C4B—C7B	115 (2)	N2—C11—H11D	109.5
C4A—C5A—C6	117.4 (9)	H11A—C11—H11D	141.1
C4A—C5A—H5A	121.3	H11B—C11—H11D	56.3
C6—C5A—H5A	121.3	H11C—C11—H11D	56.3
C4B—C5B—C6	125 (2)	N2—C11—H11E	109.5
C4B—C5B—H5B	117.5	H11A—C11—H11E	56.3
C6—C5B—H5B	117.5	H11B—C11—H11E	141.1
C5B—C6—C1	106.7 (11)	H11C—C11—H11E	56.3
C5B—C6—N1	133.4 (11)	H11D—C11—H11E	109.5
C1—C6—N1	119.8 (3)	N2—C11—H11F	109.5
C1—C6—C5A	123.8 (6)	H11A—C11—H11F	56.3
N1—C6—C5A	116.4 (6)	H11B—C11—H11F	56.3
C9—N1—C6	122.5 (3)	H11C—C11—H11F	141.1
C9—N1—C8	117.6 (3)	H11D—C11—H11F	109.5
C6—N1—C8	119.9 (3)	H11E—C11—H11F	109.5
O1—C9—N1	123.5 (3)	H3A—O3—H3C	109.5
O1—C9—C10	118.3 (3)	C3A—C7A—H7A2	109.5
N1—C9—C10	118.2 (3)	C3A—C7A—H7A3	109.5
O2—C10—N2	122.8 (3)	H7A2—C7A—H7A3	109.5
O2—C10—C9	119.0 (3)	C3A—C7A—H7A1	109.5
N2—C10—C9	118.2 (3)	H7A2—C7A—H7A1	109.5
C10—N2—C1	121.9 (3)	H7A3—C7A—H7A1	109.5
C10—N2—C11	117.0 (3)	C4B—C7B—H7B1	109.5
C1—N2—C11	121.0 (3)	C4B—C7B—H7B2	109.5
N1—C8—H8A	109.5	H7B1—C7B—H7B2	109.5
N1—C8—H8B	109.5	C4B—C7B—H7B3	109.5
H8A—C8—H8B	109.5	H7B1—C7B—H7B3	109.5
N1—C8—H8C	109.5	H7B2—C7B—H7B3	109.5
H8A—C8—H8C	109.5
C6—C1—C2A—C3A	0.8 (11)	C5B—C6—N1—C9	175.2 (19)
N2—C1—C2A—C3A	−179.0 (7)	C1—C6—N1—C9	0.7 (4)
C6—C1—C2B—C3B	1 (4)	C5A—C6—N1—C9	−178.8 (8)
N2—C1—C2B—C3B	179.2 (19)	C5B—C6—N1—C8	−3 (2)
C1—C2A—C3A—C4A	0.2 (15)	C1—C6—N1—C8	−177.6 (3)
C1—C2A—C3A—C7A	179.0 (7)	C5A—C6—N1—C8	2.8 (9)
C1—C2B—C3B—C4B	−3 (4)	C6—N1—C9—O1	−179.7 (3)
C2A—C3A—C4A—C5A	−0.9 (17)	C8—N1—C9—O1	−1.3 (5)
C7A—C3A—C4A—C5A	−179.7 (10)	C6—N1—C9—C10	−0.6 (4)
C2B—C3B—C4B—C5B	2 (5)	C8—N1—C9—C10	177.8 (3)
C2B—C3B—C4B—C7B	−178 (2)	O1—C9—C10—O2	0.6 (5)
C3A—C4A—C5A—C6	0.5 (19)	N1—C9—C10—O2	−178.5 (3)
C3B—C4B—C5B—C6	0 (5)	O1—C9—C10—N2	179.9 (3)
C7B—C4B—C5B—C6	−179 (2)	N1—C9—C10—N2	0.8 (4)
C4B—C5B—C6—C1	−2 (3)	O2—C10—N2—C1	178.2 (3)
C4B—C5B—C6—N1	−177.0 (19)	C9—C10—N2—C1	−1.0 (4)
C2B—C1—C6—C5B	1 (2)	O2—C10—N2—C11	0.1 (5)
N2—C1—C6—C5B	−176.8 (15)	C9—C10—N2—C11	−179.1 (3)
C2B—C1—C6—N1	177.2 (19)	C2B—C1—N2—C10	−177.6 (14)
N2—C1—C6—N1	−0.9 (4)	C6—C1—N2—C10	1.1 (4)
C2A—C1—C6—N1	179.2 (5)	C2A—C1—N2—C10	−179.0 (5)
N2—C1—C6—C5A	178.5 (9)	C2B—C1—N2—C11	0.4 (14)
C2A—C1—C6—C5A	−1.3 (10)	C6—C1—N2—C11	179.1 (3)
C4A—C5A—C6—C1	0.7 (17)	C2A—C1—N2—C11	−1.1 (7)
C4A—C5A—C6—N1	−179.8 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1	0.86	2.09	2.936 (4)	170
O3—H3C···O1^i	0.86	2.38	3.062 (4)	137
O3—H3C···O2^i	0.86	2.19	2.972 (5)	150
C5A—H5A···O3^ii	0.94	2.40	3.298 (13)	160
C8—H8E···O2^iii	0.97	2.45	3.335 (4)	151

Symmetry codes: (i) −x+1, −y+3, −z; (ii) −x+1/2, y−1/2, −z−1/2; (iii) x−1/2, −y+5/2, z−1/2.