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The title compound, C8H14N2O2, exists in the solid state in a zwitterionic form. The imidazolidinium fragment adopts an envelope conformation. The carboxyl­ate group is involved in an intra­molecular N+—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806027346/rz2059sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806027346/rz2059Isup2.hkl
Contains datablock I

CCDC reference: 618313

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.029
  • wR factor = 0.071
  • Data-to-parameter ratio = 9.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.37 From the CIF: _reflns_number_total 1005 Count of symmetry unique reflns 1008 Completeness (_total/calc) 99.70% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 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

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004; cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation (Siemens, 1989) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

(R,R)-Perhydrobenzimidazolium-2-carboxylate top
Crystal data top
C8H14N2O2Dx = 1.366 Mg m3
Mr = 170.21Melting point: 453 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3652 reflections
a = 5.6176 (4) Åθ = 4–25°
b = 9.1414 (5) ŵ = 0.10 mm1
c = 16.1195 (7) ÅT = 150 K
V = 827.78 (8) Å3Plate, colourless
Z = 40.4 × 0.25 × 0.08 mm
F(000) = 368
Data collection top
Kuma KM4 CCD κ geometry
diffractometer
Rint = 0.017
ω scansθmax = 26.4°, θmin = 3.8°
5897 measured reflectionsh = 67
1005 independent reflectionsk = 117
988 reflections with I > 2σ(I)l = 1920
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: difference Fourier map
wR(F2) = 0.071H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0379P)2 + 0.2085P]
where P = (Fo2 + 2Fc2)/3
1005 reflections(Δ/σ)max < 0.001
109 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.17 e Å3
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
O10.6565 (2)0.66458 (12)0.48708 (9)0.0337 (4)
O20.83759 (19)0.46996 (13)0.42995 (6)0.0189 (3)
N10.2438 (2)0.53370 (13)0.51308 (8)0.0152 (3)
H1NA0.28810.62830.51430.018*
H1NB0.11660.52450.47960.018*
C20.4488 (3)0.43702 (16)0.48305 (10)0.0158 (3)
H2A0.40140.38230.43340.019*
N30.5063 (3)0.33674 (13)0.55064 (8)0.0193 (3)
H3N0.42920.25110.54460.023*
C40.4247 (3)0.41455 (17)0.62499 (9)0.0182 (3)
H4A0.53570.49490.63600.022*
C50.1873 (3)0.48007 (17)0.59862 (9)0.0164 (3)
H5A0.07160.40030.59370.020*
C60.0924 (3)0.58922 (19)0.66091 (10)0.0256 (4)
H6A0.05940.62820.64260.031*
H6B0.20320.66970.66780.031*
C70.0631 (4)0.5051 (2)0.74287 (11)0.0350 (5)
H7A0.01300.57280.78580.042*
H7B0.06180.43270.73620.042*
C80.2913 (4)0.4280 (2)0.77112 (10)0.0305 (4)
H8A0.25720.37090.82040.037*
H8B0.40900.50110.78580.037*
C90.3956 (3)0.32667 (18)0.70422 (10)0.0248 (4)
H9A0.54860.28900.72210.030*
H9B0.28970.24460.69470.030*
C100.6662 (3)0.53467 (17)0.46410 (9)0.0163 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0232 (7)0.0136 (5)0.0645 (9)0.0037 (5)0.0125 (7)0.0039 (6)
O20.0135 (5)0.0208 (5)0.0225 (5)0.0009 (5)0.0020 (4)0.0008 (4)
N10.0112 (6)0.0123 (5)0.0222 (6)0.0002 (6)0.0003 (5)0.0003 (5)
C20.0122 (7)0.0124 (7)0.0229 (7)0.0009 (6)0.0004 (6)0.0029 (6)
N30.0180 (6)0.0108 (6)0.0292 (7)0.0008 (5)0.0027 (6)0.0040 (5)
C40.0155 (7)0.0145 (7)0.0248 (8)0.0015 (7)0.0030 (6)0.0016 (6)
C50.0145 (7)0.0159 (7)0.0187 (7)0.0017 (6)0.0010 (6)0.0010 (6)
C60.0284 (9)0.0258 (8)0.0226 (7)0.0071 (8)0.0005 (7)0.0054 (7)
C70.0420 (12)0.0405 (11)0.0225 (8)0.0058 (10)0.0053 (8)0.0056 (8)
C80.0419 (11)0.0283 (9)0.0214 (8)0.0053 (9)0.0057 (8)0.0013 (7)
C90.0257 (9)0.0212 (8)0.0274 (8)0.0024 (7)0.0046 (8)0.0060 (7)
C100.0135 (7)0.0153 (7)0.0202 (7)0.0005 (7)0.0016 (6)0.0025 (6)
Geometric parameters (Å, º) top
O1—C101.245 (2)C5—C61.512 (2)
O2—C101.2572 (18)C5—H5A0.9800
N1—C51.4975 (19)C6—C71.538 (2)
N1—C21.5301 (19)C6—H6A0.9700
N1—H1NA0.9000C6—H6B0.9700
N1—H1NB0.9000C7—C81.532 (3)
C2—N31.4601 (19)C7—H7A0.9700
C2—C101.543 (2)C7—H7B0.9700
C2—H2A0.9800C8—C91.538 (2)
N3—C41.467 (2)C8—H8A0.9700
N3—H3N0.9000C8—H8B0.9700
C4—C91.518 (2)C9—H9A0.9700
C4—C51.523 (2)C9—H9B0.9700
C4—H4A0.9800
C5—N1—C2105.18 (11)C5—C6—C7106.15 (13)
C5—N1—H1NA110.7C5—C6—H6A110.5
C2—N1—H1NA110.7C7—C6—H6A110.5
C5—N1—H1NB110.7C5—C6—H6B110.5
C2—N1—H1NB110.7C7—C6—H6B110.5
H1NA—N1—H1NB108.8H6A—C6—H6B108.7
N3—C2—N1107.04 (12)C8—C7—C6113.31 (16)
N3—C2—C10109.62 (12)C8—C7—H7A108.9
N1—C2—C10108.91 (11)C6—C7—H7A108.9
N3—C2—H2A110.4C8—C7—H7B108.9
N1—C2—H2A110.4C6—C7—H7B108.9
C10—C2—H2A110.4H7A—C7—H7B107.7
C2—N3—C4103.65 (11)C7—C8—C9112.80 (14)
C2—N3—H3N111.0C7—C8—H8A109.0
C4—N3—H3N111.1C9—C8—H8A109.0
N3—C4—C9117.68 (13)C7—C8—H8B109.0
N3—C4—C5103.67 (12)C9—C8—H8B109.0
C9—C4—C5110.41 (13)H8A—C8—H8B107.8
N3—C4—H4A108.2C4—C9—C8108.21 (13)
C9—C4—H4A108.2C4—C9—H9A110.1
C5—C4—H4A108.2C8—C9—H9A110.1
N1—C5—C6118.04 (13)C4—C9—H9B110.1
N1—C5—C4101.54 (11)C8—C9—H9B110.1
C6—C5—C4112.51 (13)H9A—C9—H9B108.4
N1—C5—H5A108.1O1—C10—O2127.75 (15)
C6—C5—H5A108.1O1—C10—C2117.29 (14)
C4—C5—H5A108.1O2—C10—C2114.88 (12)
N1—C2—N3—C424.89 (15)C7—C8—C9—C453.2 (2)
C2—N3—C4—C541.71 (14)C8—C9—C4—C557.06 (18)
N3—C4—C5—N142.04 (13)C9—C4—C5—C663.90 (17)
C4—C5—N1—C225.92 (13)N1—C2—C10—O2172.28 (11)
C5—N1—C2—N31.42 (14)N1—C2—C10—O110.69 (19)
C4—C5—C6—C759.59 (18)N3—C2—C10—O1106.12 (16)
C5—C6—C7—C854.6 (2)N3—C2—C10—O270.91 (16)
C6—C7—C8—C954.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1NA···O10.902.142.6425 (18)114
N1—H1NA···O1i0.902.032.8014 (17)143
N1—H1NB···O2ii0.901.832.7098 (17)167
N3—H3N···O2iii0.902.132.9760 (17)157
Symmetry codes: (i) x1/2, y+3/2, z+1; (ii) x1, y, z; (iii) x1/2, y+1/2, z+1.
 

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