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The title compound, C16H16N2O2·CH4O, exists in the solid state in a zwitterionic form. Inter­molecular hydrogen bonds assemble the mol­ecules into a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806025955/fl2034sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806025955/fl2034Isup2.hkl
Contains datablock I

CCDC reference: 618966

Key indicators

  • Single-crystal X-ray study
  • T = 130 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.046
  • wR factor = 0.091
  • Data-to-parameter ratio = 7.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.41 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 5
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 25.02 From the CIF: _reflns_number_total 1616 Count of symmetry unique reflns 1624 Completeness (_total/calc) 99.51% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 3 ALERT type 4 Improvement, methodology, query or suggestion

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 Operation Manual (Siemens, 1989) and Mercury (Version 1.4; Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

(4R,5R)-4,5-Diphenylimidazolidinium-2-carboxylate methanol solvate top
Crystal data top
C16H16N2O2·CH4ODx = 1.289 Mg m3
Mr = 300.35Melting point: 427-433K, dec. K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 5.9624 (4) ÅCell parameters from 5684 reflections
b = 8.8288 (6) Åθ = 4.1–25.0°
c = 29.4086 (19) ŵ = 0.09 mm1
V = 1548.09 (18) Å3T = 130 K
Z = 4Prism, colourless
F(000) = 6400.4 × 0.3 × 0.05 mm
Data collection top
Kuma KM-4-CCD κ-geometry
diffractometer
1528 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
Graphite monochromatorθmax = 25.0°, θmin = 4.1°
ω scansh = 67
11990 measured reflectionsk = 1010
1616 independent reflectionsl = 3532
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)] = 0.046Hydrogen site location: difference Fourier map
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.16 w = 1/[σ2(Fo2) + (0.0376P)2 + 0.5565P]
where P = (Fo2 + 2Fc2)/3
1616 reflections(Δ/σ)max = 0.002
218 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.18 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
O10.8989 (3)0.6806 (2)0.20786 (7)0.0270 (5)
O20.7832 (3)0.8665 (2)0.25388 (7)0.0273 (5)
N10.4936 (4)0.5502 (3)0.19973 (8)0.0194 (5)
H1NA0.627 (6)0.525 (4)0.1942 (11)0.031 (9)*
H1NB0.413 (5)0.480 (4)0.2189 (10)0.033 (9)*
C20.5050 (5)0.7056 (3)0.22249 (9)0.0205 (6)
H2A0.43160.70140.25230.025*
N30.3841 (4)0.8094 (3)0.19289 (8)0.0213 (5)
H3N0.244 (6)0.801 (3)0.1983 (10)0.021 (8)*
C40.4168 (5)0.7461 (3)0.14696 (9)0.0199 (6)
H4A0.57340.76270.13820.024*
C50.3824 (5)0.5737 (3)0.15443 (9)0.0187 (6)
H5A0.22140.55540.15820.022*
C60.2695 (5)0.8109 (3)0.11010 (9)0.0219 (6)
C70.0614 (5)0.8761 (3)0.11864 (10)0.0266 (7)
H7A0.00860.88260.14830.032*
C80.0685 (5)0.9317 (3)0.08297 (11)0.0305 (7)
H8A0.20610.97680.08920.037*
C90.0039 (6)0.9210 (3)0.03873 (10)0.0298 (7)
H9A0.08510.95690.01510.036*
C100.2108 (6)0.8562 (3)0.02970 (11)0.0331 (8)
H10A0.26170.84910.00010.040*
C110.3426 (5)0.8019 (3)0.06520 (9)0.0266 (7)
H11A0.48160.75900.05880.032*
C120.4679 (5)0.4671 (3)0.11814 (9)0.0207 (6)
C130.6812 (5)0.4817 (3)0.09926 (10)0.0265 (7)
H130.77790.55680.10970.032*
C140.7487 (6)0.3842 (4)0.06494 (10)0.0334 (8)
H140.88980.39560.05190.040*
C150.6081 (6)0.2699 (4)0.04995 (10)0.0380 (9)
H150.65520.20430.02710.046*
C160.3976 (6)0.2532 (4)0.06893 (11)0.0374 (8)
H160.30290.17620.05910.045*
C170.3283 (5)0.3527 (3)0.10286 (10)0.0298 (7)
H170.18610.34220.11540.036*
C180.7520 (5)0.7532 (3)0.22832 (9)0.0192 (6)
O1M0.8434 (4)0.3362 (2)0.19607 (8)0.0330 (6)
H1M0.971 (7)0.354 (5)0.2163 (13)0.061 (12)*
C2M0.8616 (7)0.1879 (4)0.17818 (11)0.0412 (9)
H1MA1.01780.16810.16200.049*
H2MB0.74310.17250.15660.049*
H2MC0.84230.11570.20230.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0217 (11)0.0273 (11)0.0321 (11)0.0017 (10)0.0030 (9)0.0054 (9)
O20.0241 (11)0.0211 (10)0.0367 (12)0.0010 (9)0.0054 (9)0.0110 (10)
N10.0173 (13)0.0180 (12)0.0228 (13)0.0013 (11)0.0005 (11)0.0002 (11)
C20.0221 (15)0.0198 (14)0.0196 (14)0.0010 (13)0.0003 (13)0.0030 (12)
N30.0200 (14)0.0212 (12)0.0227 (13)0.0034 (11)0.0019 (11)0.0037 (10)
C40.0205 (15)0.0171 (13)0.0220 (14)0.0003 (12)0.0001 (12)0.0005 (12)
C50.0178 (15)0.0196 (14)0.0188 (14)0.0003 (13)0.0017 (12)0.0002 (12)
C60.0244 (15)0.0138 (13)0.0277 (15)0.0025 (13)0.0051 (13)0.0003 (12)
C70.0254 (16)0.0271 (16)0.0274 (16)0.0005 (14)0.0011 (13)0.0054 (13)
C80.0237 (17)0.0244 (15)0.0435 (19)0.0028 (14)0.0068 (15)0.0068 (14)
C90.0369 (19)0.0228 (15)0.0298 (17)0.0017 (15)0.0138 (15)0.0000 (13)
C100.047 (2)0.0280 (16)0.0239 (16)0.0070 (17)0.0073 (15)0.0056 (14)
C110.0296 (17)0.0252 (15)0.0249 (16)0.0071 (14)0.0008 (13)0.0004 (13)
C120.0243 (16)0.0181 (14)0.0197 (14)0.0038 (13)0.0040 (12)0.0003 (12)
C130.0263 (17)0.0234 (15)0.0298 (16)0.0038 (13)0.0025 (13)0.0014 (13)
C140.0349 (18)0.0383 (19)0.0270 (16)0.0146 (16)0.0038 (15)0.0021 (15)
C150.058 (2)0.0320 (19)0.0237 (17)0.0209 (19)0.0064 (16)0.0064 (14)
C160.052 (2)0.0248 (16)0.0359 (18)0.0014 (17)0.0103 (17)0.0084 (15)
C170.0326 (18)0.0270 (16)0.0297 (17)0.0056 (15)0.0038 (14)0.0023 (14)
C180.0211 (15)0.0182 (13)0.0184 (13)0.0004 (13)0.0008 (12)0.0023 (12)
O1M0.0346 (13)0.0242 (12)0.0402 (13)0.0074 (10)0.0132 (11)0.0062 (10)
C2M0.056 (2)0.0321 (17)0.0356 (18)0.0011 (18)0.0054 (17)0.0017 (16)
Geometric parameters (Å, º) top
O1—C181.241 (3)C9—C101.386 (5)
O2—C181.265 (3)C9—H9A0.9300
N1—C51.502 (4)C10—C111.392 (4)
N1—C21.528 (3)C10—H10A0.9300
N1—H1NA0.84 (3)C11—H11A0.9300
N1—H1NB0.97 (3)C12—C171.383 (4)
C2—N31.455 (4)C12—C131.394 (4)
C2—C181.541 (4)C13—C141.387 (4)
C2—H2A0.9800C13—H130.9300
N3—C41.475 (4)C14—C151.384 (5)
N3—H3N0.85 (3)C14—H140.9300
C4—C61.508 (4)C15—C161.381 (5)
C4—C51.551 (4)C15—H150.9300
C4—H4A0.9800C16—C171.392 (4)
C5—C121.512 (4)C16—H160.9300
C5—H5A0.9800C17—H170.9300
C6—C71.391 (4)O1M—C2M1.416 (4)
C6—C111.393 (4)O1M—H1M0.98 (4)
C7—C81.393 (4)C2M—H1MA1.0600
C7—H7A0.9300C2M—H2MB0.9600
C8—C91.374 (4)C2M—H2MC0.9600
C8—H8A0.9300
C5—N1—C2106.5 (2)C8—C9—H9A120.3
C5—N1—H1NA106 (2)C10—C9—H9A120.3
C2—N1—H1NA107 (2)C9—C10—C11120.1 (3)
C5—N1—H1NB112.8 (18)C9—C10—H10A120.0
C2—N1—H1NB110.1 (18)C11—C10—H10A120.0
H1NA—N1—H1NB114 (3)C10—C11—C6121.0 (3)
N3—C2—N1106.3 (2)C10—C11—H11A119.5
N3—C2—C18111.6 (2)C6—C11—H11A119.5
N1—C2—C18109.7 (2)C17—C12—C13119.2 (3)
N3—C2—H2A109.7C17—C12—C5118.8 (3)
N1—C2—H2A109.7C13—C12—C5122.1 (3)
C18—C2—H2A109.7C14—C13—C12119.8 (3)
C2—N3—C4104.1 (2)C14—C13—H13120.1
C2—N3—H3N108 (2)C12—C13—H13120.1
C4—N3—H3N105 (2)C15—C14—C13120.6 (3)
N3—C4—C6115.9 (2)C15—C14—H14119.7
N3—C4—C5103.0 (2)C13—C14—H14119.7
C6—C4—C5113.4 (2)C16—C15—C14120.0 (3)
N3—C4—H4A108.0C16—C15—H15120.0
C6—C4—H4A108.0C14—C15—H15120.0
C5—C4—H4A108.0C15—C16—C17119.5 (3)
N1—C5—C12113.0 (2)C15—C16—H16120.3
N1—C5—C4101.7 (2)C17—C16—H16120.3
C12—C5—C4117.8 (2)C12—C17—C16121.0 (3)
N1—C5—H5A107.9C12—C17—H17119.5
C12—C5—H5A107.9C16—C17—H17119.5
C4—C5—H5A107.9O1—C18—O2126.4 (3)
C7—C6—C11118.3 (3)O1—C18—C2118.7 (2)
C7—C6—C4123.2 (3)O2—C18—C2115.0 (2)
C11—C6—C4118.5 (3)C2M—O1M—H1M108 (2)
C6—C7—C8120.4 (3)O1M—C2M—H1MA112.7
C6—C7—H7A119.8O1M—C2M—H2MB108.7
C8—C7—H7A119.8H1MA—C2M—H2MB109.1
C9—C8—C7120.9 (3)O1M—C2M—H2MC109.3
C9—C8—H8A119.5H1MA—C2M—H2MC109.1
C7—C8—H8A119.5H2MB—C2M—H2MC107.8
C8—C9—C10119.3 (3)
C5—N1—C2—N35.4 (3)C8—C9—C10—C110.4 (4)
C5—N1—C2—C18115.4 (2)C9—C10—C11—C60.3 (5)
N1—C2—N3—C430.2 (3)C7—C6—C11—C100.2 (4)
C18—C2—N3—C489.3 (3)C4—C6—C11—C10178.3 (3)
C2—N3—C4—C6167.4 (2)N1—C5—C12—C17109.1 (3)
C2—N3—C4—C542.9 (3)C4—C5—C12—C17132.6 (3)
C2—N1—C5—C12147.3 (2)N1—C5—C12—C1371.7 (3)
C2—N1—C5—C420.0 (3)C4—C5—C12—C1346.5 (4)
N3—C4—C5—N138.5 (3)C17—C12—C13—C141.3 (4)
C6—C4—C5—N1164.6 (2)C5—C12—C13—C14177.8 (3)
N3—C4—C5—C12162.6 (2)C12—C13—C14—C151.5 (4)
C6—C4—C5—C1271.3 (3)C13—C14—C15—C160.6 (5)
N3—C4—C6—C725.5 (4)C14—C15—C16—C170.5 (5)
C5—C4—C6—C793.4 (3)C13—C12—C17—C160.3 (4)
N3—C4—C6—C11156.1 (3)C5—C12—C17—C16178.9 (3)
C5—C4—C6—C1185.0 (3)C15—C16—C17—C120.6 (5)
C11—C6—C7—C80.5 (4)N3—C2—C18—O1104.8 (3)
C4—C6—C7—C8178.9 (3)N1—C2—C18—O112.7 (3)
C6—C7—C8—C91.2 (4)N3—C2—C18—O274.5 (3)
C7—C8—C9—C101.1 (5)N1—C2—C18—O2167.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1NA···O10.84 (3)2.17 (3)2.687 (3)120 (3)
N1—H1NA···O1M0.84 (3)2.11 (3)2.816 (3)142 (3)
N1—H1NB···O2i0.97 (3)1.74 (4)2.686 (3)167 (3)
N3—H3N···O1ii0.85 (3)2.33 (3)3.139 (3)158 (3)
O1M—H1M···O2iii0.98 (4)1.71 (4)2.683 (3)171 (4)
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x1, y, z; (iii) x+2, y1/2, z+1/2.
 

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