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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
CCDC reference: 618966
Key indicators
- Single-crystal X-ray study
- T = 130 K
- Mean (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
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.
(4
R,5
R)-4,5-Diphenylimidazolidinium-2-carboxylate methanol solvate
top
Crystal data top
C16H16N2O2·CH4O | Dx = 1.289 Mg m−3 |
Mr = 300.35 | Melting point: 427-433K, dec. K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.9624 (4) Å | Cell parameters from 5684 reflections |
b = 8.8288 (6) Å | θ = 4.1–25.0° |
c = 29.4086 (19) Å | µ = 0.09 mm−1 |
V = 1548.09 (18) Å3 | T = 130 K |
Z = 4 | Prism, colourless |
F(000) = 640 | 0.4 × 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 tube | Rint = 0.041 |
Graphite monochromator | θmax = 25.0°, θmin = 4.1° |
ω scans | h = −6→7 |
11990 measured reflections | k = −10→10 |
1616 independent reflections | l = −35→32 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.091 | H 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 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.8989 (3) | 0.6806 (2) | 0.20786 (7) | 0.0270 (5) | |
O2 | 0.7832 (3) | 0.8665 (2) | 0.25388 (7) | 0.0273 (5) | |
N1 | 0.4936 (4) | 0.5502 (3) | 0.19973 (8) | 0.0194 (5) | |
H1NA | 0.627 (6) | 0.525 (4) | 0.1942 (11) | 0.031 (9)* | |
H1NB | 0.413 (5) | 0.480 (4) | 0.2189 (10) | 0.033 (9)* | |
C2 | 0.5050 (5) | 0.7056 (3) | 0.22249 (9) | 0.0205 (6) | |
H2A | 0.4316 | 0.7014 | 0.2523 | 0.025* | |
N3 | 0.3841 (4) | 0.8094 (3) | 0.19289 (8) | 0.0213 (5) | |
H3N | 0.244 (6) | 0.801 (3) | 0.1983 (10) | 0.021 (8)* | |
C4 | 0.4168 (5) | 0.7461 (3) | 0.14696 (9) | 0.0199 (6) | |
H4A | 0.5734 | 0.7627 | 0.1382 | 0.024* | |
C5 | 0.3824 (5) | 0.5737 (3) | 0.15443 (9) | 0.0187 (6) | |
H5A | 0.2214 | 0.5554 | 0.1582 | 0.022* | |
C6 | 0.2695 (5) | 0.8109 (3) | 0.11010 (9) | 0.0219 (6) | |
C7 | 0.0614 (5) | 0.8761 (3) | 0.11864 (10) | 0.0266 (7) | |
H7A | 0.0086 | 0.8826 | 0.1483 | 0.032* | |
C8 | −0.0685 (5) | 0.9317 (3) | 0.08297 (11) | 0.0305 (7) | |
H8A | −0.2061 | 0.9768 | 0.0892 | 0.037* | |
C9 | 0.0039 (6) | 0.9210 (3) | 0.03873 (10) | 0.0298 (7) | |
H9A | −0.0851 | 0.9569 | 0.0151 | 0.036* | |
C10 | 0.2108 (6) | 0.8562 (3) | 0.02970 (11) | 0.0331 (8) | |
H10A | 0.2617 | 0.8491 | −0.0001 | 0.040* | |
C11 | 0.3426 (5) | 0.8019 (3) | 0.06520 (9) | 0.0266 (7) | |
H11A | 0.4816 | 0.7590 | 0.0588 | 0.032* | |
C12 | 0.4679 (5) | 0.4671 (3) | 0.11814 (9) | 0.0207 (6) | |
C13 | 0.6812 (5) | 0.4817 (3) | 0.09926 (10) | 0.0265 (7) | |
H13 | 0.7779 | 0.5568 | 0.1097 | 0.032* | |
C14 | 0.7487 (6) | 0.3842 (4) | 0.06494 (10) | 0.0334 (8) | |
H14 | 0.8898 | 0.3956 | 0.0519 | 0.040* | |
C15 | 0.6081 (6) | 0.2699 (4) | 0.04995 (10) | 0.0380 (9) | |
H15 | 0.6552 | 0.2043 | 0.0271 | 0.046* | |
C16 | 0.3976 (6) | 0.2532 (4) | 0.06893 (11) | 0.0374 (8) | |
H16 | 0.3029 | 0.1762 | 0.0591 | 0.045* | |
C17 | 0.3283 (5) | 0.3527 (3) | 0.10286 (10) | 0.0298 (7) | |
H17 | 0.1861 | 0.3422 | 0.1154 | 0.036* | |
C18 | 0.7520 (5) | 0.7532 (3) | 0.22832 (9) | 0.0192 (6) | |
O1M | 0.8434 (4) | 0.3362 (2) | 0.19607 (8) | 0.0330 (6) | |
H1M | 0.971 (7) | 0.354 (5) | 0.2163 (13) | 0.061 (12)* | |
C2M | 0.8616 (7) | 0.1879 (4) | 0.17818 (11) | 0.0412 (9) | |
H1MA | 1.0178 | 0.1681 | 0.1620 | 0.049* | |
H2MB | 0.7431 | 0.1725 | 0.1566 | 0.049* | |
H2MC | 0.8423 | 0.1157 | 0.2023 | 0.049* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0217 (11) | 0.0273 (11) | 0.0321 (11) | −0.0017 (10) | 0.0030 (9) | −0.0054 (9) |
O2 | 0.0241 (11) | 0.0211 (10) | 0.0367 (12) | 0.0010 (9) | −0.0054 (9) | −0.0110 (10) |
N1 | 0.0173 (13) | 0.0180 (12) | 0.0228 (13) | −0.0013 (11) | −0.0005 (11) | 0.0002 (11) |
C2 | 0.0221 (15) | 0.0198 (14) | 0.0196 (14) | 0.0010 (13) | 0.0003 (13) | −0.0030 (12) |
N3 | 0.0200 (14) | 0.0212 (12) | 0.0227 (13) | 0.0034 (11) | −0.0019 (11) | −0.0037 (10) |
C4 | 0.0205 (15) | 0.0171 (13) | 0.0220 (14) | 0.0003 (12) | 0.0001 (12) | 0.0005 (12) |
C5 | 0.0178 (15) | 0.0196 (14) | 0.0188 (14) | −0.0003 (13) | −0.0017 (12) | −0.0002 (12) |
C6 | 0.0244 (15) | 0.0138 (13) | 0.0277 (15) | −0.0025 (13) | −0.0051 (13) | −0.0003 (12) |
C7 | 0.0254 (16) | 0.0271 (16) | 0.0274 (16) | −0.0005 (14) | 0.0011 (13) | 0.0054 (13) |
C8 | 0.0237 (17) | 0.0244 (15) | 0.0435 (19) | 0.0028 (14) | −0.0068 (15) | 0.0068 (14) |
C9 | 0.0369 (19) | 0.0228 (15) | 0.0298 (17) | 0.0017 (15) | −0.0138 (15) | 0.0000 (13) |
C10 | 0.047 (2) | 0.0280 (16) | 0.0239 (16) | 0.0070 (17) | −0.0073 (15) | −0.0056 (14) |
C11 | 0.0296 (17) | 0.0252 (15) | 0.0249 (16) | 0.0071 (14) | −0.0008 (13) | −0.0004 (13) |
C12 | 0.0243 (16) | 0.0181 (14) | 0.0197 (14) | 0.0038 (13) | −0.0040 (12) | 0.0003 (12) |
C13 | 0.0263 (17) | 0.0234 (15) | 0.0298 (16) | 0.0038 (13) | −0.0025 (13) | 0.0014 (13) |
C14 | 0.0349 (18) | 0.0383 (19) | 0.0270 (16) | 0.0146 (16) | 0.0038 (15) | 0.0021 (15) |
C15 | 0.058 (2) | 0.0320 (19) | 0.0237 (17) | 0.0209 (19) | −0.0064 (16) | −0.0064 (14) |
C16 | 0.052 (2) | 0.0248 (16) | 0.0359 (18) | −0.0014 (17) | −0.0103 (17) | −0.0084 (15) |
C17 | 0.0326 (18) | 0.0270 (16) | 0.0297 (17) | −0.0056 (15) | −0.0038 (14) | −0.0023 (14) |
C18 | 0.0211 (15) | 0.0182 (13) | 0.0184 (13) | 0.0004 (13) | 0.0008 (12) | 0.0023 (12) |
O1M | 0.0346 (13) | 0.0242 (12) | 0.0402 (13) | 0.0074 (10) | −0.0132 (11) | −0.0062 (10) |
C2M | 0.056 (2) | 0.0321 (17) | 0.0356 (18) | −0.0011 (18) | 0.0054 (17) | −0.0017 (16) |
Geometric parameters (Å, º) top
O1—C18 | 1.241 (3) | C9—C10 | 1.386 (5) |
O2—C18 | 1.265 (3) | C9—H9A | 0.9300 |
N1—C5 | 1.502 (4) | C10—C11 | 1.392 (4) |
N1—C2 | 1.528 (3) | C10—H10A | 0.9300 |
N1—H1NA | 0.84 (3) | C11—H11A | 0.9300 |
N1—H1NB | 0.97 (3) | C12—C17 | 1.383 (4) |
C2—N3 | 1.455 (4) | C12—C13 | 1.394 (4) |
C2—C18 | 1.541 (4) | C13—C14 | 1.387 (4) |
C2—H2A | 0.9800 | C13—H13 | 0.9300 |
N3—C4 | 1.475 (4) | C14—C15 | 1.384 (5) |
N3—H3N | 0.85 (3) | C14—H14 | 0.9300 |
C4—C6 | 1.508 (4) | C15—C16 | 1.381 (5) |
C4—C5 | 1.551 (4) | C15—H15 | 0.9300 |
C4—H4A | 0.9800 | C16—C17 | 1.392 (4) |
C5—C12 | 1.512 (4) | C16—H16 | 0.9300 |
C5—H5A | 0.9800 | C17—H17 | 0.9300 |
C6—C7 | 1.391 (4) | O1M—C2M | 1.416 (4) |
C6—C11 | 1.393 (4) | O1M—H1M | 0.98 (4) |
C7—C8 | 1.393 (4) | C2M—H1MA | 1.0600 |
C7—H7A | 0.9300 | C2M—H2MB | 0.9600 |
C8—C9 | 1.374 (4) | C2M—H2MC | 0.9600 |
C8—H8A | 0.9300 | | |
| | | |
C5—N1—C2 | 106.5 (2) | C8—C9—H9A | 120.3 |
C5—N1—H1NA | 106 (2) | C10—C9—H9A | 120.3 |
C2—N1—H1NA | 107 (2) | C9—C10—C11 | 120.1 (3) |
C5—N1—H1NB | 112.8 (18) | C9—C10—H10A | 120.0 |
C2—N1—H1NB | 110.1 (18) | C11—C10—H10A | 120.0 |
H1NA—N1—H1NB | 114 (3) | C10—C11—C6 | 121.0 (3) |
N3—C2—N1 | 106.3 (2) | C10—C11—H11A | 119.5 |
N3—C2—C18 | 111.6 (2) | C6—C11—H11A | 119.5 |
N1—C2—C18 | 109.7 (2) | C17—C12—C13 | 119.2 (3) |
N3—C2—H2A | 109.7 | C17—C12—C5 | 118.8 (3) |
N1—C2—H2A | 109.7 | C13—C12—C5 | 122.1 (3) |
C18—C2—H2A | 109.7 | C14—C13—C12 | 119.8 (3) |
C2—N3—C4 | 104.1 (2) | C14—C13—H13 | 120.1 |
C2—N3—H3N | 108 (2) | C12—C13—H13 | 120.1 |
C4—N3—H3N | 105 (2) | C15—C14—C13 | 120.6 (3) |
N3—C4—C6 | 115.9 (2) | C15—C14—H14 | 119.7 |
N3—C4—C5 | 103.0 (2) | C13—C14—H14 | 119.7 |
C6—C4—C5 | 113.4 (2) | C16—C15—C14 | 120.0 (3) |
N3—C4—H4A | 108.0 | C16—C15—H15 | 120.0 |
C6—C4—H4A | 108.0 | C14—C15—H15 | 120.0 |
C5—C4—H4A | 108.0 | C15—C16—C17 | 119.5 (3) |
N1—C5—C12 | 113.0 (2) | C15—C16—H16 | 120.3 |
N1—C5—C4 | 101.7 (2) | C17—C16—H16 | 120.3 |
C12—C5—C4 | 117.8 (2) | C12—C17—C16 | 121.0 (3) |
N1—C5—H5A | 107.9 | C12—C17—H17 | 119.5 |
C12—C5—H5A | 107.9 | C16—C17—H17 | 119.5 |
C4—C5—H5A | 107.9 | O1—C18—O2 | 126.4 (3) |
C7—C6—C11 | 118.3 (3) | O1—C18—C2 | 118.7 (2) |
C7—C6—C4 | 123.2 (3) | O2—C18—C2 | 115.0 (2) |
C11—C6—C4 | 118.5 (3) | C2M—O1M—H1M | 108 (2) |
C6—C7—C8 | 120.4 (3) | O1M—C2M—H1MA | 112.7 |
C6—C7—H7A | 119.8 | O1M—C2M—H2MB | 108.7 |
C8—C7—H7A | 119.8 | H1MA—C2M—H2MB | 109.1 |
C9—C8—C7 | 120.9 (3) | O1M—C2M—H2MC | 109.3 |
C9—C8—H8A | 119.5 | H1MA—C2M—H2MC | 109.1 |
C7—C8—H8A | 119.5 | H2MB—C2M—H2MC | 107.8 |
C8—C9—C10 | 119.3 (3) | | |
| | | |
C5—N1—C2—N3 | 5.4 (3) | C8—C9—C10—C11 | 0.4 (4) |
C5—N1—C2—C18 | −115.4 (2) | C9—C10—C11—C6 | 0.3 (5) |
N1—C2—N3—C4 | −30.2 (3) | C7—C6—C11—C10 | −0.2 (4) |
C18—C2—N3—C4 | 89.3 (3) | C4—C6—C11—C10 | 178.3 (3) |
C2—N3—C4—C6 | 167.4 (2) | N1—C5—C12—C17 | 109.1 (3) |
C2—N3—C4—C5 | 42.9 (3) | C4—C5—C12—C17 | −132.6 (3) |
C2—N1—C5—C12 | 147.3 (2) | N1—C5—C12—C13 | −71.7 (3) |
C2—N1—C5—C4 | 20.0 (3) | C4—C5—C12—C13 | 46.5 (4) |
N3—C4—C5—N1 | −38.5 (3) | C17—C12—C13—C14 | 1.3 (4) |
C6—C4—C5—N1 | −164.6 (2) | C5—C12—C13—C14 | −177.8 (3) |
N3—C4—C5—C12 | −162.6 (2) | C12—C13—C14—C15 | −1.5 (4) |
C6—C4—C5—C12 | 71.3 (3) | C13—C14—C15—C16 | 0.6 (5) |
N3—C4—C6—C7 | −25.5 (4) | C14—C15—C16—C17 | 0.5 (5) |
C5—C4—C6—C7 | 93.4 (3) | C13—C12—C17—C16 | −0.3 (4) |
N3—C4—C6—C11 | 156.1 (3) | C5—C12—C17—C16 | 178.9 (3) |
C5—C4—C6—C11 | −85.0 (3) | C15—C16—C17—C12 | −0.6 (5) |
C11—C6—C7—C8 | −0.5 (4) | N3—C2—C18—O1 | −104.8 (3) |
C4—C6—C7—C8 | −178.9 (3) | N1—C2—C18—O1 | 12.7 (3) |
C6—C7—C8—C9 | 1.2 (4) | N3—C2—C18—O2 | 74.5 (3) |
C7—C8—C9—C10 | −1.1 (5) | N1—C2—C18—O2 | −167.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1NA···O1 | 0.84 (3) | 2.17 (3) | 2.687 (3) | 120 (3) |
N1—H1NA···O1M | 0.84 (3) | 2.11 (3) | 2.816 (3) | 142 (3) |
N1—H1NB···O2i | 0.97 (3) | 1.74 (4) | 2.686 (3) | 167 (3) |
N3—H3N···O1ii | 0.85 (3) | 2.33 (3) | 3.139 (3) | 158 (3) |
O1M—H1M···O2iii | 0.98 (4) | 1.71 (4) | 2.683 (3) | 171 (4) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1, y, z; (iii) −x+2, y−1/2, −z+1/2. |
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