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In the mol­ecule of the title compound, C8H11NO2, the cyclo­hexane ring adopts a chair conformation, while the pyrrole ring has an envelope conformation. In the crystal structure, inter­molecular N—H...O hydrogen bonds link the mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042742/hk2317sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042742/hk2317Isup2.hkl
Contains datablock I

CCDC reference: 663714

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.033
  • wR factor = 0.090
  • Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT024_ALERT_4_B Merging of Friedel Pairs is STRONGLY Indicated . !
Alert level G REFLT03_ALERT_4_G ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases. From the CIF: _diffrn_reflns_theta_max 28.18 From the CIF: _reflns_number_total 1843 Count of symmetry unique reflns 1110 Completeness (_total/calc) 166.04% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 733 Fraction of Friedel pairs measured 0.660 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . R
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 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 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

Comment top

Hexahydrophthalimide is a key intermediate for the synthesis of hypoglycemic drug mitiglinide (Yamaguchi et al., 1998). As part of our studies in this area, we report herein the synthesis and crystal structure of the title compound, (I).

In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987).

Ring A (C1—C6) is not planar, having total puckering amplitude, QT, of 0.519 (3) Å, and chair conformation [φ = -47.93 (3)° and θ = 161.98 (3)°] (Cremer & Pople, 1975). Ring B (C1/C6—C8/N1) has envelope conformation with atom C6 displaced by -0.394 (3) Å from the plane of the other four ring atoms.

In the crystal structure, the intermolecular N—H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they seem to be effective in the stabilization of the structure.

Related literature top

For related literature, see: Yamaguchi et al. (1998). For general background, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).

Experimental top

Hexahydrophthalic anhydride (20 mmol) and urea (10 mmol) was added to a 25 ml flask. After the mixture was heated at reflux for 1 h, 5 ml of ice water was added, then the crystals of (I) were obtained by filtration. Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate solution.

Refinement top

H1A (for NH) was located in difference syntheses and only its position was refined [N—H = 0.860 (17) Å, Uiso(H) = 0.044 Å2]. The remaining H atoms were positioned geometrically, with C—H = 0.98 and 0.97 Å for methine, and methylene H, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Structure description top

Hexahydrophthalimide is a key intermediate for the synthesis of hypoglycemic drug mitiglinide (Yamaguchi et al., 1998). As part of our studies in this area, we report herein the synthesis and crystal structure of the title compound, (I).

In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987).

Ring A (C1—C6) is not planar, having total puckering amplitude, QT, of 0.519 (3) Å, and chair conformation [φ = -47.93 (3)° and θ = 161.98 (3)°] (Cremer & Pople, 1975). Ring B (C1/C6—C8/N1) has envelope conformation with atom C6 displaced by -0.394 (3) Å from the plane of the other four ring atoms.

In the crystal structure, the intermolecular N—H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they seem to be effective in the stabilization of the structure.

For related literature, see: Yamaguchi et al. (1998). For general background, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. A drawing of the title molecular structure, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.
Perhydrophthalimide top
Crystal data top
C8H11NO2F(000) = 328
Mr = 153.18Dx = 1.333 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 6.7574 (12) Åθ = 2.8–18.0°
b = 7.8615 (14) ŵ = 0.10 mm1
c = 14.371 (3) ÅT = 273 K
V = 763.4 (2) Å3Block, colorless
Z = 40.30 × 0.26 × 0.24 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1699 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.057
Graphite monochromatorθmax = 28.2°, θmin = 2.8°
φ and ω scansh = 88
Absorption correction: ψ scan
(North et al., 1968)
k = 106
Tmin = 0.97, Tmax = 0.98l = 1914
4773 measured reflections3 standard reflections every 120 min
1843 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.0566P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
1843 reflectionsΔρmax = 0.22 e Å3
104 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.42 (2)
Crystal data top
C8H11NO2V = 763.4 (2) Å3
Mr = 153.18Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.7574 (12) ŵ = 0.10 mm1
b = 7.8615 (14) ÅT = 273 K
c = 14.371 (3) Å0.30 × 0.26 × 0.24 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1699 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.057
Tmin = 0.97, Tmax = 0.983 standard reflections every 120 min
4773 measured reflections intensity decay: 1%
1843 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.22 e Å3
1843 reflectionsΔρmin = 0.14 e Å3
104 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.47695 (15)0.91918 (12)0.12610 (7)0.0494 (3)
O20.03151 (14)0.63013 (12)0.25855 (7)0.0477 (3)
N10.20581 (16)0.80816 (13)0.20032 (7)0.0368 (3)
H1A0.148 (2)0.903 (2)0.2135 (11)0.044*
C10.26087 (16)0.51872 (14)0.17742 (8)0.0325 (3)
H10.27800.42250.22000.039*
C20.16634 (17)0.46046 (16)0.08509 (8)0.0385 (3)
H2A0.06230.37890.09820.046*
H2B0.10660.55770.05450.046*
C30.3167 (2)0.37982 (18)0.02014 (9)0.0454 (3)
H3A0.37150.27870.04900.055*
H3B0.25210.34610.03720.055*
C40.48208 (18)0.50434 (17)0.00141 (8)0.0454 (3)
H4A0.42700.60530.03030.054*
H4B0.57370.45280.04510.054*
C50.59260 (17)0.55445 (19)0.08653 (10)0.0455 (3)
H5A0.68580.64430.07170.055*
H5B0.66780.45740.10850.055*
C60.45644 (16)0.61537 (15)0.16426 (8)0.0350 (3)
H60.53050.60430.22260.042*
C70.38956 (17)0.79860 (15)0.15769 (7)0.0344 (3)
C80.12617 (18)0.65170 (15)0.21917 (8)0.0340 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0569 (6)0.0393 (5)0.0521 (5)0.0139 (5)0.0103 (4)0.0003 (4)
O20.0505 (5)0.0376 (5)0.0551 (5)0.0033 (4)0.0209 (4)0.0017 (4)
N10.0439 (5)0.0273 (5)0.0393 (5)0.0005 (4)0.0070 (4)0.0023 (4)
C10.0356 (5)0.0284 (5)0.0334 (5)0.0012 (4)0.0010 (4)0.0028 (4)
C20.0345 (5)0.0386 (6)0.0424 (6)0.0026 (5)0.0014 (5)0.0081 (5)
C30.0486 (7)0.0418 (7)0.0459 (7)0.0001 (6)0.0026 (6)0.0123 (5)
C40.0481 (7)0.0446 (7)0.0435 (7)0.0051 (6)0.0121 (6)0.0024 (6)
C50.0320 (5)0.0462 (7)0.0584 (8)0.0024 (5)0.0070 (5)0.0020 (6)
C60.0318 (5)0.0369 (6)0.0363 (5)0.0003 (5)0.0047 (4)0.0001 (5)
C70.0380 (6)0.0349 (6)0.0304 (5)0.0050 (5)0.0011 (4)0.0025 (4)
C80.0400 (6)0.0316 (5)0.0303 (5)0.0023 (5)0.0027 (4)0.0004 (4)
Geometric parameters (Å, º) top
C1—C81.5104 (16)C4—H4B0.9700
C1—C61.5360 (15)C5—C61.5243 (17)
C1—C21.5423 (16)C5—H5A0.9700
C1—H10.9800C5—H5B0.9700
C2—C31.5186 (17)C6—C71.5127 (17)
C2—H2A0.9700C6—H60.9800
C2—H2B0.9700C7—O11.2055 (14)
C3—C41.5173 (18)C7—N11.3867 (15)
C3—H3A0.9700C8—O21.2183 (15)
C3—H3B0.9700C8—N11.3696 (14)
C4—C51.5199 (19)N1—H1A0.860 (17)
C4—H4A0.9700
C8—C1—C6103.01 (9)H4A—C4—H4B108.0
C8—C1—C2107.32 (9)C4—C5—C6113.21 (10)
C6—C1—C2113.41 (9)C4—C5—H5A108.9
C8—C1—H1110.9C6—C5—H5A108.9
C6—C1—H1110.9C4—C5—H5B108.9
C2—C1—H1110.9C6—C5—H5B108.9
C3—C2—C1112.06 (10)H5A—C5—H5B107.7
C3—C2—H2A109.2C7—C6—C5115.70 (10)
C1—C2—H2A109.2C7—C6—C1102.81 (9)
C3—C2—H2B109.2C5—C6—C1117.01 (10)
C1—C2—H2B109.2C7—C6—H6106.9
H2A—C2—H2B107.9C5—C6—H6106.9
C4—C3—C2110.42 (10)C1—C6—H6106.9
C4—C3—H3A109.6O1—C7—N1124.22 (12)
C2—C3—H3A109.6O1—C7—C6128.75 (11)
C4—C3—H3B109.6N1—C7—C6106.95 (9)
C2—C3—H3B109.6O2—C8—N1124.09 (11)
H3A—C3—H3B108.1O2—C8—C1127.97 (11)
C3—C4—C5111.06 (10)N1—C8—C1107.83 (10)
C3—C4—H4A109.4C8—N1—C7112.99 (10)
C5—C4—H4A109.4C8—N1—H1A123.5 (10)
C3—C4—H4B109.4C7—N1—H1A123.5 (10)
C5—C4—H4B109.4
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.860 (17)1.995 (17)2.8537 (15)175.8 (14)
Symmetry code: (i) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC8H11NO2
Mr153.18
Crystal system, space groupOrthorhombic, P212121
Temperature (K)273
a, b, c (Å)6.7574 (12), 7.8615 (14), 14.371 (3)
V3)763.4 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.30 × 0.26 × 0.24
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.97, 0.98
No. of measured, independent and
observed [I > 2σ(I)] reflections
4773, 1843, 1699
Rint0.057
(sin θ/λ)max1)0.664
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.090, 1.07
No. of reflections1843
No. of parameters104
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.14

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.860 (17)1.995 (17)2.8537 (15)175.8 (14)
Symmetry code: (i) x, y+1/2, z+1/2.
 

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