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Crystallization from a 20-year-old commercial source of 3-ethyl-4-methyl-3-pyrrolin-2-one afforded 1:1 co-crystals of this compound (C7H11NO) with its oxidized derivative, 3-ethyl-4-methyl-3-pyrroline-2,5-dione (C7H9NO2). The compound crystallizes in the space group P\overline{1}, with two mol­ecules of each species in the asymmetric unit. These four mol­ecules form a hydrogen-bonded tetra­mer with a dimer of 3-ethyl-4-methyl-3-pyrrolin-2-one as the core flanked by one mol­ecule of the dione on each side.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314619012094/hb4316sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314619012094/hb4316Isup2.hkl
Contains datablock I

mol

MDL mol file https://doi.org/10.1107/S2414314619012094/hb4316Isup3.mol
Supplementary material

mol

MDL mol file https://doi.org/10.1107/S2414314619012094/hb4316Isup4.mol
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314619012094/hb4316Isup5.cml
Supplementary material

CCDC reference: 1950911

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.049
  • wR factor = 0.129
  • Data-to-parameter ratio = 21.5

checkCIF/PLATON results

No syntax errors found



Alert level C CRYSC01_ALERT_1_C The word below has not been recognised as a standard identifier. off PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.4 Note
Alert level G PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 2 Note C7 H9 N O2 PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 5 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 19 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 3 ALERT level G = General information/check it is not something unexpected 1 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SAINT (Bruker, 2014); cell refinement: APEX2 (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL (Sheldrick, 2015a); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

3-Ethyl-4-methyl-3-pyrrolin-2-one–3-ethyl-4-methyl-3-pyrroline-2,5-dione (1/1) top
Crystal data top
C7H9NO2·C7H11NOZ = 4
Mr = 264.32F(000) = 568
Triclinic, P1Dx = 1.260 Mg m3
a = 10.2673 (17) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.885 (2) ÅCell parameters from 4195 reflections
c = 12.839 (2) Åθ = 2.2–30.4°
α = 90.601 (3)°µ = 0.09 mm1
β = 108.694 (2)°T = 100 K
γ = 108.797 (2)°Block, off-white
V = 1393.6 (4) Å30.5 × 0.4 × 0.4 mm
Data collection top
Bruker APEXII CCD
diffractometer
5738 reflections with I > 2σ(I)
φ and ω scansRint = 0.042
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
θmax = 29.6°, θmin = 1.7°
Tmin = 0.638, Tmax = 0.746h = 1414
22087 measured reflectionsk = 1616
7807 independent reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.129 w = 1/[σ2(Fo2) + (0.0602P)2 + 0.2427P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
7807 reflectionsΔρmax = 0.47 e Å3
363 parametersΔρmin = 0.31 e Å3
0 restraints
Special details top

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.

Refinement. 1. Fixed Uiso At 1.2 times of: All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C5(H5A,H5B), C19(H19A,H19B), C12(H12A,H12B), C11(H11A,H11B), C26(H26A,H26B) 2.b Idealised Me refined as rotating group: C6(H6A,H6B,H6C), C21(H21A,H21B,H21C), C28(H28A,H28B,H28C), C14(H14A,H14B, H14C), C7(H7A,H7B,H7C), C13(H13A,H13B,H13C), C20(H20A,H20B,H20C), C27(H27A, H27B,H27C)

The coordinates of the four hydrogen atoms (H1–H4) engaged in hydrogen bonds were refined while all others were treated with a riding model.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O20.21235 (10)0.36055 (8)0.67113 (8)0.0189 (2)
O60.01203 (11)0.43139 (9)0.40166 (8)0.0204 (2)
O40.75738 (11)0.53952 (9)1.01712 (8)0.0227 (2)
O10.56722 (10)0.62186 (9)0.75879 (8)0.0200 (2)
N10.38644 (12)0.55072 (10)0.58794 (9)0.0167 (2)
H10.3252 (18)0.4919 (15)0.6090 (13)0.020*
N30.83545 (13)0.71001 (10)0.93659 (10)0.0184 (2)
H30.7591 (19)0.6936 (14)0.8759 (14)0.022*
N20.41748 (13)0.39669 (10)0.82662 (9)0.0173 (2)
H20.4672 (18)0.4676 (15)0.8144 (13)0.021*
N40.07317 (13)0.28418 (11)0.50433 (10)0.0179 (2)
H40.0032 (19)0.3029 (14)0.5626 (14)0.021*
C171.05941 (14)0.79960 (12)1.07610 (10)0.0150 (3)
C220.08165 (14)0.34340 (12)0.41122 (11)0.0155 (3)
C150.84850 (15)0.63481 (12)1.01803 (11)0.0161 (3)
C160.99545 (14)0.69420 (11)1.10621 (10)0.0148 (3)
C40.35382 (14)0.58429 (12)0.47670 (10)0.0160 (3)
H4A0.2614650.6019240.4529210.019*
H4B0.3463180.5202590.4228510.019*
C250.19971 (14)0.18630 (12)0.48532 (11)0.0165 (3)
C80.28393 (14)0.33068 (11)0.75769 (10)0.0145 (3)
C20.57626 (14)0.71910 (11)0.59323 (11)0.0143 (3)
C90.23720 (14)0.21533 (11)0.80256 (10)0.0145 (3)
C10.51327 (14)0.62710 (11)0.65760 (11)0.0146 (3)
C30.48329 (14)0.69498 (12)0.48829 (11)0.0160 (3)
C180.95907 (15)0.81199 (12)0.96574 (11)0.0158 (3)
C230.22806 (14)0.27622 (12)0.32497 (11)0.0158 (3)
C50.72351 (14)0.81347 (12)0.64460 (11)0.0166 (3)
H5A0.7355310.8429000.7207040.020*
H5B0.7313640.8819510.6008890.020*
C100.34397 (15)0.21846 (12)0.89684 (11)0.0181 (3)
C240.29647 (14)0.18262 (12)0.36832 (11)0.0160 (3)
C191.04928 (15)0.63491 (12)1.20459 (11)0.0179 (3)
H19A0.9675780.5944561.2312840.022*
H19B1.1260800.6962031.2650120.022*
C120.09622 (15)0.11766 (12)0.74122 (11)0.0166 (3)
H12A0.0168300.1518050.7163280.020*
H12B0.0716840.0581960.7915710.020*
C110.46781 (15)0.33592 (12)0.92045 (11)0.0200 (3)
H11A0.4833130.3813710.9910250.024*
H11B0.5599780.3237720.9238190.024*
C60.84446 (15)0.76321 (13)0.64858 (13)0.0217 (3)
H6A0.8375830.7405550.5728850.033*
H6B0.8330630.6925350.6881080.033*
H6C0.9402130.8243330.6873160.033*
C260.27140 (16)0.31362 (13)0.21204 (11)0.0205 (3)
H26A0.2321830.4021050.2176770.025*
H26B0.3794990.2875460.1800190.025*
C211.20247 (15)0.89522 (12)1.13460 (12)0.0212 (3)
H21A1.2395590.8812281.2119390.032*
H21B1.1894810.9734181.1322490.032*
H21C1.2726300.8940041.0981760.032*
C280.44102 (15)0.08562 (13)0.31799 (12)0.0227 (3)
H28A0.4268900.0149640.2900580.034*
H28B0.5036160.1133950.2566250.034*
H28C0.4877040.0646460.3741650.034*
C140.34989 (17)0.12475 (13)0.97320 (12)0.0267 (3)
H14A0.3657960.1587891.0479560.040*
H14B0.4305050.0968710.9749600.040*
H14C0.2572350.0571540.9467430.040*
C70.49576 (17)0.76137 (14)0.39212 (12)0.0251 (3)
H7A0.4903890.7069040.3318310.038*
H7B0.5896130.8276690.4147150.038*
H7C0.4154650.7931870.3665740.038*
C130.10590 (18)0.05544 (14)0.64105 (12)0.0279 (3)
H13A0.1387380.1152450.5944650.042*
H13B0.0092830.0021380.5980840.042*
H13C0.1758990.0131670.6661470.042*
C201.11168 (19)0.54321 (14)1.17583 (12)0.0281 (3)
H20A1.0375660.4853501.1129930.042*
H20B1.1393360.5010841.2399940.042*
H20C1.1982100.5843091.1560190.042*
C270.21402 (19)0.25974 (17)0.13569 (13)0.0326 (4)
H27A0.2389180.2897680.0637390.049*
H27B0.2587900.1722310.1253210.049*
H27C0.1074190.2825250.1688590.049*
O30.98077 (11)0.89459 (9)0.91156 (8)0.0225 (2)
O50.22727 (11)0.11830 (9)0.55131 (8)0.0247 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0159 (5)0.0195 (5)0.0151 (5)0.0016 (4)0.0015 (4)0.0072 (4)
O60.0182 (5)0.0173 (5)0.0219 (5)0.0000 (4)0.0078 (4)0.0008 (4)
O40.0206 (5)0.0181 (5)0.0217 (5)0.0031 (4)0.0070 (4)0.0010 (4)
O10.0163 (5)0.0203 (5)0.0155 (5)0.0006 (4)0.0005 (4)0.0057 (4)
N10.0146 (5)0.0142 (5)0.0148 (5)0.0004 (4)0.0019 (4)0.0046 (4)
N30.0154 (6)0.0178 (6)0.0132 (5)0.0001 (5)0.0008 (5)0.0016 (4)
N20.0161 (6)0.0133 (5)0.0152 (5)0.0011 (5)0.0018 (4)0.0050 (4)
N40.0130 (5)0.0202 (6)0.0131 (5)0.0005 (5)0.0000 (4)0.0009 (4)
C170.0151 (6)0.0147 (6)0.0118 (6)0.0023 (5)0.0030 (5)0.0002 (5)
C220.0156 (6)0.0157 (6)0.0155 (6)0.0053 (5)0.0056 (5)0.0001 (5)
C150.0166 (6)0.0165 (6)0.0130 (6)0.0023 (5)0.0056 (5)0.0006 (5)
C160.0157 (6)0.0146 (6)0.0117 (6)0.0030 (5)0.0038 (5)0.0002 (5)
C40.0142 (6)0.0169 (6)0.0128 (6)0.0029 (5)0.0019 (5)0.0022 (5)
C250.0138 (6)0.0158 (6)0.0178 (6)0.0043 (5)0.0038 (5)0.0007 (5)
C80.0150 (6)0.0137 (6)0.0124 (6)0.0018 (5)0.0048 (5)0.0021 (5)
C20.0127 (6)0.0117 (6)0.0179 (6)0.0034 (5)0.0052 (5)0.0037 (5)
C90.0156 (6)0.0113 (6)0.0130 (6)0.0003 (5)0.0044 (5)0.0007 (5)
C10.0129 (6)0.0127 (6)0.0169 (6)0.0039 (5)0.0037 (5)0.0037 (5)
C30.0148 (6)0.0158 (6)0.0177 (6)0.0049 (5)0.0065 (5)0.0045 (5)
C180.0151 (6)0.0161 (6)0.0134 (6)0.0034 (5)0.0031 (5)0.0004 (5)
C230.0132 (6)0.0149 (6)0.0171 (6)0.0049 (5)0.0022 (5)0.0012 (5)
C50.0136 (6)0.0117 (6)0.0198 (7)0.0005 (5)0.0032 (5)0.0031 (5)
C100.0179 (7)0.0144 (6)0.0158 (6)0.0006 (5)0.0025 (5)0.0032 (5)
C240.0134 (6)0.0143 (6)0.0182 (6)0.0051 (5)0.0024 (5)0.0001 (5)
C190.0213 (7)0.0182 (7)0.0116 (6)0.0042 (5)0.0048 (5)0.0042 (5)
C120.0157 (6)0.0153 (6)0.0133 (6)0.0003 (5)0.0034 (5)0.0030 (5)
C110.0173 (7)0.0168 (7)0.0169 (7)0.0002 (5)0.0003 (5)0.0051 (5)
C60.0156 (7)0.0205 (7)0.0268 (7)0.0044 (6)0.0062 (6)0.0049 (6)
C260.0186 (7)0.0218 (7)0.0179 (7)0.0061 (6)0.0027 (5)0.0043 (5)
C210.0181 (7)0.0175 (7)0.0185 (7)0.0013 (5)0.0014 (5)0.0030 (5)
C280.0170 (7)0.0171 (7)0.0256 (7)0.0021 (5)0.0002 (6)0.0015 (6)
C140.0234 (8)0.0197 (7)0.0240 (8)0.0009 (6)0.0026 (6)0.0101 (6)
C70.0218 (7)0.0309 (8)0.0195 (7)0.0049 (6)0.0070 (6)0.0109 (6)
C130.0292 (8)0.0215 (7)0.0223 (7)0.0047 (6)0.0086 (6)0.0056 (6)
C200.0371 (9)0.0300 (8)0.0190 (7)0.0177 (7)0.0059 (7)0.0050 (6)
C270.0367 (9)0.0478 (10)0.0173 (7)0.0218 (8)0.0071 (7)0.0050 (7)
O30.0255 (5)0.0181 (5)0.0179 (5)0.0032 (4)0.0036 (4)0.0060 (4)
O50.0225 (5)0.0241 (5)0.0230 (5)0.0039 (4)0.0061 (4)0.0090 (4)
Geometric parameters (Å, º) top
O2—C81.2467 (15)C5—C61.530 (2)
O6—C221.2100 (16)C10—C111.5026 (19)
O4—C151.2115 (16)C10—C141.4945 (18)
O1—C11.2495 (15)C24—C281.4887 (19)
N1—H10.887 (16)C19—H19A0.9900
N1—C41.4500 (16)C19—H19B0.9900
N1—C11.3395 (17)C19—C201.526 (2)
N3—H30.875 (17)C12—H12A0.9900
N3—C151.3846 (17)C12—H12B0.9900
N3—C181.3838 (17)C12—C131.523 (2)
N2—H20.879 (16)C11—H11A0.9900
N2—C81.3391 (17)C11—H11B0.9900
N2—C111.4491 (17)C6—H6A0.9800
N4—H40.856 (17)C6—H6B0.9800
N4—C221.3865 (17)C6—H6C0.9800
N4—C251.3848 (17)C26—H26A0.9900
C17—C161.3389 (18)C26—H26B0.9900
C17—C181.5023 (18)C26—C271.523 (2)
C17—C211.4874 (18)C21—H21A0.9800
C22—C231.5047 (18)C21—H21B0.9800
C15—C161.5028 (18)C21—H21C0.9800
C16—C191.4899 (18)C28—H28A0.9800
C4—H4A0.9900C28—H28B0.9800
C4—H4B0.9900C28—H28C0.9800
C4—C31.5040 (18)C14—H14A0.9800
C25—C241.5031 (18)C14—H14B0.9800
C25—O51.2132 (16)C14—H14C0.9800
C8—C91.4871 (17)C7—H7A0.9800
C2—C11.4842 (17)C7—H7B0.9800
C2—C31.3415 (18)C7—H7C0.9800
C2—C51.4936 (18)C13—H13A0.9800
C9—C101.3380 (19)C13—H13B0.9800
C9—C121.4934 (18)C13—H13C0.9800
C3—C71.4900 (18)C20—H20A0.9800
C18—O31.2124 (16)C20—H20B0.9800
C23—C241.3419 (18)C20—H20C0.9800
C23—C261.4918 (18)C27—H27A0.9800
C5—H5A0.9900C27—H27B0.9800
C5—H5B0.9900C27—H27C0.9800
C4—N1—H1124.0 (10)H19A—C19—H19B108.0
C1—N1—H1123.9 (10)C20—C19—H19A109.4
C1—N1—C4111.72 (11)C20—C19—H19B109.4
C15—N3—H3123.6 (11)C9—C12—H12A109.4
C18—N3—H3126.2 (11)C9—C12—H12B109.4
C18—N3—C15110.15 (11)C9—C12—C13111.30 (11)
C8—N2—H2122.8 (10)H12A—C12—H12B108.0
C8—N2—C11111.70 (11)C13—C12—H12A109.4
C11—N2—H2125.5 (10)C13—C12—H12B109.4
C22—N4—H4123.8 (11)N2—C11—C10102.71 (11)
C25—N4—H4125.6 (11)N2—C11—H11A111.2
C25—N4—C22110.40 (11)N2—C11—H11B111.2
C16—C17—C18108.26 (11)C10—C11—H11A111.2
C16—C17—C21130.11 (12)C10—C11—H11B111.2
C21—C17—C18121.63 (11)H11A—C11—H11B109.1
O6—C22—N4126.14 (12)C5—C6—H6A109.5
O6—C22—C23127.07 (12)C5—C6—H6B109.5
N4—C22—C23106.79 (11)C5—C6—H6C109.5
O4—C15—N3125.76 (13)H6A—C6—H6B109.5
O4—C15—C16127.26 (12)H6A—C6—H6C109.5
N3—C15—C16106.98 (11)H6B—C6—H6C109.5
C17—C16—C15107.82 (11)C23—C26—H26A109.4
C17—C16—C19130.63 (12)C23—C26—H26B109.4
C19—C16—C15121.53 (11)C23—C26—C27111.36 (12)
N1—C4—H4A111.2H26A—C26—H26B108.0
N1—C4—H4B111.2C27—C26—H26A109.4
N1—C4—C3102.76 (10)C27—C26—H26B109.4
H4A—C4—H4B109.1C17—C21—H21A109.5
C3—C4—H4A111.2C17—C21—H21B109.5
C3—C4—H4B111.2C17—C21—H21C109.5
N4—C25—C24106.64 (11)H21A—C21—H21B109.5
O5—C25—N4126.34 (13)H21A—C21—H21C109.5
O5—C25—C24127.01 (12)H21B—C21—H21C109.5
O2—C8—N2125.99 (12)C24—C28—H28A109.5
O2—C8—C9126.30 (12)C24—C28—H28B109.5
N2—C8—C9107.71 (11)C24—C28—H28C109.5
C1—C2—C5121.51 (11)H28A—C28—H28B109.5
C3—C2—C1108.08 (11)H28A—C28—H28C109.5
C3—C2—C5130.31 (12)H28B—C28—H28C109.5
C8—C9—C12121.34 (11)C10—C14—H14A109.5
C10—C9—C8107.89 (11)C10—C14—H14B109.5
C10—C9—C12130.69 (12)C10—C14—H14C109.5
O1—C1—N1125.75 (12)H14A—C14—H14B109.5
O1—C1—C2126.53 (12)H14A—C14—H14C109.5
N1—C1—C2107.71 (11)H14B—C14—H14C109.5
C2—C3—C4109.72 (11)C3—C7—H7A109.5
C2—C3—C7128.87 (13)C3—C7—H7B109.5
C7—C3—C4121.41 (12)C3—C7—H7C109.5
N3—C18—C17106.77 (11)H7A—C7—H7B109.5
O3—C18—N3125.96 (12)H7A—C7—H7C109.5
O3—C18—C17127.27 (12)H7B—C7—H7C109.5
C24—C23—C22107.84 (11)C12—C13—H13A109.5
C24—C23—C26131.04 (12)C12—C13—H13B109.5
C26—C23—C22121.03 (12)C12—C13—H13C109.5
C2—C5—H5A109.6H13A—C13—H13B109.5
C2—C5—H5B109.6H13A—C13—H13C109.5
C2—C5—C6110.49 (11)H13B—C13—H13C109.5
H5A—C5—H5B108.1C19—C20—H20A109.5
C6—C5—H5A109.6C19—C20—H20B109.5
C6—C5—H5B109.6C19—C20—H20C109.5
C9—C10—C11109.98 (11)H20A—C20—H20B109.5
C9—C10—C14128.69 (13)H20A—C20—H20C109.5
C14—C10—C11121.33 (12)H20B—C20—H20C109.5
C23—C24—C25108.31 (11)C26—C27—H27A109.5
C23—C24—C28130.25 (12)C26—C27—H27B109.5
C28—C24—C25121.43 (12)C26—C27—H27C109.5
C16—C19—H19A109.4H27A—C27—H27B109.5
C16—C19—H19B109.4H27A—C27—H27C109.5
C16—C19—C20110.95 (11)H27B—C27—H27C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.89 (2)1.97 (2)2.8487 (15)173 (2)
N2—H2···O10.88 (2)2.05 (2)2.9222 (15)171 (2)
N3—H3···O10.88 (2)1.97 (2)2.8202 (15)165 (2)
N4—H4···O20.86 (2)2.03 (2)2.8677 (15)165 (2)
 

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