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In the title compound, C
12H
20N
4O
4·C
2H
4O
2·H
2O, the main fragment contains two
L-alanine residues with a zwitterionic structure. The crystal structure is characterized by a two-dimensional network of O—H
O, O—H
N and N—H
O hydrogen bonds.
Supporting information
CCDC reference: 263679
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.041
- wR factor = 0.117
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT771_ALERT_2_A Suspect N-H Bond in CIF: N3 -H3 .. 1.51 Ang.
| Author Response: This bond length does not correspond to a valence bond
but to a component of a strong O23---H3...N3 hydrogen bond.
See _publ_section_exptl_refinement.
|
Alert level C
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C22
PLAT355_ALERT_3_C Long O-H Bond (0.82A) O23 - H3 ... 1.06 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D H15A .. H252 .. 2.12 Ang.
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 30.00
From the CIF: _reflns_number_total 3107
Count of symmetry unique reflns 3113
Completeness (_total/calc) 99.81%
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
1 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
2 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
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus and Mercury (CCDC, 2004); software used to prepare material for publication: SHELXTL-Plus.
4,4'-(2-Methyl-1
H-imidazole-4,5-diyl)bis[2(
S)-methyl-3-azoniabutanoate] acetic acid monohydrate
top
Crystal data top
C12H20N4O4·C2H4O2·H2O | F(000) = 388 |
Mr = 362.39 | Dx = 1.242 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 38 reflections |
a = 13.337 (3) Å | θ = 3.3–13.1° |
b = 5.3977 (14) Å | µ = 0.10 mm−1 |
c = 14.312 (4) Å | T = 298 K |
β = 109.898 (19)° | Prism, colorless |
V = 968.8 (4) Å3 | 0.48 × 0.26 × 0.26 mm |
Z = 2 | |
Data collection top
Bruker P4 diffractometer | Rint = 0.032 |
Radiation source: fine-focus sealed tube, FN4 | θmax = 30.0°, θmin = 1.8° |
Graphite monochromator | h = −1→18 |
ω scans | k = −1→7 |
4070 measured reflections | l = −20→19 |
3107 independent reflections | 3 standard reflections every 97 reflections |
2403 reflections with I > 2σ(I) | intensity decay: 1% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: See text |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0655P)2 + 0.0268P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3107 reflections | Δρmax = 0.22 e Å−3 |
254 parameters | Δρmin = −0.21 e Å−3 |
1 restraint | Absolute structure: see text |
Primary atom site location: structure-invariant direct methods | |
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 | |
N1 | 0.25362 (13) | 0.7685 (4) | 0.45737 (12) | 0.0427 (5) | |
H1 | 0.235 (2) | 0.775 (7) | 0.512 (2) | 0.064* | |
C2 | 0.33517 (18) | 0.6503 (6) | 0.44365 (16) | 0.0488 (6) | |
N3 | 0.33876 (13) | 0.6967 (5) | 0.35367 (12) | 0.0458 (5) | |
H3 | 0.428 (3) | 0.597 (8) | 0.322 (2) | 0.069* | |
C4 | 0.25284 (16) | 0.8477 (5) | 0.30738 (13) | 0.0371 (4) | |
C5 | 0.19917 (15) | 0.8937 (4) | 0.37142 (12) | 0.0360 (4) | |
C6 | 0.4087 (2) | 0.4838 (9) | 0.5189 (2) | 0.0773 (10) | |
H6A | 0.4717 | 0.4558 | 0.5023 | 0.116* | |
H6B | 0.3738 | 0.3286 | 0.5196 | 0.116* | |
H6C | 0.4280 | 0.5595 | 0.5833 | 0.116* | |
C7 | 0.09830 (16) | 1.0277 (4) | 0.35994 (14) | 0.0387 (5) | |
H7A | 0.0817 | 1.1391 | 0.3035 | 0.046* | |
H7B | 0.1069 | 1.1260 | 0.4189 | 0.046* | |
N8 | 0.00847 (13) | 0.8471 (4) | 0.34451 (11) | 0.0345 (4) | |
H8A | 0.008 (2) | 0.747 (6) | 0.291 (2) | 0.052* | |
H8B | 0.023 (2) | 0.753 (6) | 0.4068 (19) | 0.052* | |
C9 | −0.09879 (16) | 0.9667 (5) | 0.31896 (13) | 0.0381 (5) | |
H9A | −0.1037 | 1.0995 | 0.2709 | 0.046* | |
C10 | −0.11489 (16) | 1.0792 (5) | 0.41069 (13) | 0.0373 (4) | |
O11 | −0.19280 (14) | 1.2257 (5) | 0.39006 (11) | 0.0573 (5) | |
O12 | −0.05559 (12) | 1.0158 (3) | 0.49437 (9) | 0.0425 (4) | |
C13 | −0.1846 (2) | 0.7782 (7) | 0.2713 (2) | 0.0686 (9) | |
H13A | −0.1767 | 0.7185 | 0.2110 | 0.103* | |
H13B | −0.2534 | 0.8540 | 0.2564 | 0.103* | |
H13C | −0.1784 | 0.6422 | 0.3162 | 0.103* | |
C14 | 0.22902 (18) | 0.9303 (4) | 0.20237 (13) | 0.0384 (5) | |
H14A | 0.2912 | 1.0113 | 0.1959 | 0.046* | |
H14B | 0.1710 | 1.0491 | 0.1849 | 0.046* | |
N15 | 0.19883 (14) | 0.7133 (4) | 0.13300 (11) | 0.0325 (3) | |
H15A | 0.142 (2) | 0.638 (6) | 0.1401 (18) | 0.049* | |
H15B | 0.256 (2) | 0.603 (6) | 0.1441 (19) | 0.049* | |
C16 | 0.16377 (16) | 0.7871 (4) | 0.02568 (12) | 0.0342 (4) | |
H16A | 0.1167 | 0.9313 | 0.0164 | 0.041* | |
C17 | 0.10002 (17) | 0.5753 (4) | −0.03866 (14) | 0.0364 (4) | |
O18 | 0.10392 (16) | 0.3681 (3) | −0.00159 (12) | 0.0525 (4) | |
O19 | 0.04880 (15) | 0.6309 (4) | −0.12722 (11) | 0.0513 (5) | |
C20 | 0.2584 (2) | 0.8595 (7) | −0.00444 (17) | 0.0559 (7) | |
H20A | 0.2923 | 1.0032 | 0.0324 | 0.084* | |
H20B | 0.2343 | 0.8963 | −0.0742 | 0.084* | |
H20C | 0.3084 | 0.7250 | 0.0094 | 0.084* | |
C21 | 0.5587 (3) | 0.3071 (15) | 0.1953 (3) | 0.136 (3) | |
H21A | 0.5561 | 0.3584 | 0.1303 | 0.204* | |
H21B | 0.5529 | 0.1300 | 0.1969 | 0.204* | |
H21C | 0.6252 | 0.3584 | 0.2435 | 0.204* | |
C22 | 0.4692 (2) | 0.4223 (8) | 0.2189 (2) | 0.0664 (9) | |
O23 | 0.49361 (16) | 0.5357 (8) | 0.30221 (16) | 0.1040 (13) | |
O24 | 0.37846 (15) | 0.4044 (5) | 0.16188 (15) | 0.0696 (6) | |
O25 | 0.01209 (13) | 0.5929 (4) | 0.17334 (11) | 0.0395 (3) | |
H251 | −0.015 (3) | 0.449 (8) | 0.152 (2) | 0.059* | |
H252 | −0.020 (3) | 0.689 (7) | 0.125 (2) | 0.059* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0353 (8) | 0.0640 (13) | 0.0273 (7) | −0.0042 (9) | 0.0089 (6) | 0.0043 (8) |
C2 | 0.0391 (10) | 0.0670 (17) | 0.0371 (9) | 0.0030 (12) | 0.0089 (8) | 0.0069 (11) |
N3 | 0.0347 (8) | 0.0661 (14) | 0.0347 (8) | 0.0034 (10) | 0.0092 (6) | 0.0015 (9) |
C4 | 0.0355 (9) | 0.0450 (12) | 0.0292 (7) | −0.0066 (9) | 0.0089 (7) | −0.0018 (9) |
C5 | 0.0350 (9) | 0.0449 (12) | 0.0273 (7) | −0.0044 (9) | 0.0096 (7) | −0.0016 (8) |
C6 | 0.0607 (15) | 0.108 (3) | 0.0565 (14) | 0.029 (2) | 0.0119 (12) | 0.0288 (19) |
C7 | 0.0422 (10) | 0.0420 (12) | 0.0324 (8) | −0.0027 (10) | 0.0135 (7) | −0.0019 (9) |
N8 | 0.0343 (8) | 0.0410 (9) | 0.0283 (6) | 0.0019 (8) | 0.0107 (6) | −0.0022 (7) |
C9 | 0.0366 (9) | 0.0497 (12) | 0.0278 (7) | 0.0075 (10) | 0.0108 (7) | −0.0012 (9) |
C10 | 0.0407 (10) | 0.0438 (12) | 0.0299 (8) | 0.0018 (10) | 0.0153 (7) | −0.0011 (9) |
O11 | 0.0568 (9) | 0.0823 (14) | 0.0354 (7) | 0.0288 (10) | 0.0190 (7) | 0.0029 (9) |
O12 | 0.0488 (8) | 0.0477 (10) | 0.0289 (6) | 0.0045 (8) | 0.0106 (6) | −0.0014 (7) |
C13 | 0.0402 (12) | 0.088 (2) | 0.0700 (16) | −0.0032 (15) | 0.0091 (11) | −0.0331 (18) |
C14 | 0.0471 (11) | 0.0395 (11) | 0.0295 (8) | −0.0074 (10) | 0.0140 (8) | −0.0024 (8) |
N15 | 0.0356 (8) | 0.0353 (9) | 0.0254 (6) | −0.0005 (8) | 0.0087 (6) | 0.0012 (7) |
C16 | 0.0423 (10) | 0.0346 (10) | 0.0239 (7) | 0.0024 (9) | 0.0092 (7) | 0.0019 (8) |
C17 | 0.0424 (10) | 0.0363 (11) | 0.0307 (8) | 0.0032 (9) | 0.0125 (8) | −0.0047 (8) |
O18 | 0.0687 (11) | 0.0366 (9) | 0.0434 (8) | −0.0029 (9) | 0.0078 (7) | −0.0005 (7) |
O19 | 0.0715 (11) | 0.0469 (10) | 0.0282 (7) | 0.0037 (9) | 0.0075 (7) | −0.0068 (7) |
C20 | 0.0596 (14) | 0.0706 (18) | 0.0413 (10) | −0.0138 (14) | 0.0222 (10) | 0.0029 (13) |
C21 | 0.0600 (18) | 0.238 (8) | 0.101 (3) | 0.033 (3) | 0.0166 (18) | −0.064 (4) |
C22 | 0.0422 (12) | 0.095 (3) | 0.0590 (14) | 0.0062 (16) | 0.0136 (10) | −0.0028 (17) |
O23 | 0.0454 (10) | 0.190 (4) | 0.0710 (13) | 0.0073 (17) | 0.0134 (9) | −0.049 (2) |
O24 | 0.0493 (10) | 0.0752 (16) | 0.0728 (11) | 0.0126 (11) | 0.0057 (8) | −0.0132 (11) |
O25 | 0.0448 (8) | 0.0394 (8) | 0.0316 (6) | −0.0004 (7) | 0.0093 (6) | −0.0024 (7) |
Geometric parameters (Å, º) top
N1—C2 | 1.332 (3) | C13—H13B | 0.9600 |
N1—C5 | 1.374 (3) | C13—H13C | 0.9600 |
N1—H1 | 0.90 (3) | C14—N15 | 1.499 (3) |
C2—N3 | 1.329 (3) | C14—H14A | 0.9700 |
C2—C6 | 1.487 (4) | C14—H14B | 0.9700 |
N3—C4 | 1.378 (3) | N15—C16 | 1.499 (2) |
N3—H3 | 1.51 (3) | N15—H15A | 0.89 (3) |
C4—C5 | 1.364 (3) | N15—H15B | 0.93 (3) |
C4—C14 | 1.494 (3) | C16—C20 | 1.517 (3) |
C5—C7 | 1.487 (3) | C16—C17 | 1.531 (3) |
C6—H6A | 0.9600 | C16—H16A | 0.9800 |
C6—H6B | 0.9600 | C17—O18 | 1.231 (3) |
C6—H6C | 0.9600 | C17—O19 | 1.255 (3) |
C7—N8 | 1.502 (3) | C20—H20A | 0.9600 |
C7—H7A | 0.9700 | C20—H20B | 0.9600 |
C7—H7B | 0.9700 | C20—H20C | 0.9600 |
N8—C9 | 1.497 (3) | C21—C22 | 1.484 (5) |
N8—H8A | 0.94 (3) | C21—H21A | 0.9600 |
N8—H8B | 0.99 (3) | C21—H21B | 0.9600 |
C9—C13 | 1.510 (4) | C21—H21C | 0.9600 |
C9—C10 | 1.527 (3) | C22—O24 | 1.212 (3) |
C9—H9A | 0.9800 | C22—O23 | 1.280 (4) |
C10—O11 | 1.259 (3) | O23—H3 | 1.06 (3) |
C10—O12 | 1.238 (2) | O25—H251 | 0.87 (4) |
C13—H13A | 0.9600 | O25—H252 | 0.85 (4) |
| | | |
C2—N1—C5 | 108.23 (17) | C9—C13—H13B | 109.5 |
C2—N1—H1 | 129 (2) | H13A—C13—H13B | 109.5 |
C5—N1—H1 | 123 (2) | C9—C13—H13C | 109.5 |
N3—C2—N1 | 110.7 (2) | H13A—C13—H13C | 109.5 |
N3—C2—C6 | 125.7 (2) | H13B—C13—H13C | 109.5 |
N1—C2—C6 | 123.6 (2) | C4—C14—N15 | 110.51 (19) |
C2—N3—C4 | 106.21 (18) | C4—C14—H14A | 109.5 |
C2—N3—H3 | 121.1 (12) | N15—C14—H14A | 109.5 |
C4—N3—H3 | 132.7 (12) | C4—C14—H14B | 109.5 |
C5—C4—N3 | 108.98 (17) | N15—C14—H14B | 109.5 |
C5—C4—C14 | 129.9 (2) | H14A—C14—H14B | 108.1 |
N3—C4—C14 | 121.14 (18) | C14—N15—C16 | 113.02 (17) |
C4—C5—N1 | 105.88 (19) | C14—N15—H15A | 109.1 (18) |
C4—C5—C7 | 132.56 (18) | C16—N15—H15A | 104.9 (16) |
N1—C5—C7 | 121.40 (17) | C14—N15—H15B | 111.3 (18) |
C2—C6—H6A | 109.5 | C16—N15—H15B | 107.1 (16) |
C2—C6—H6B | 109.5 | H15A—N15—H15B | 111 (3) |
H6A—C6—H6B | 109.5 | N15—C16—C20 | 111.10 (17) |
C2—C6—H6C | 109.5 | N15—C16—C17 | 109.48 (17) |
H6A—C6—H6C | 109.5 | C20—C16—C17 | 111.52 (18) |
H6B—C6—H6C | 109.5 | N15—C16—H16A | 108.2 |
C5—C7—N8 | 110.30 (18) | C20—C16—H16A | 108.2 |
C5—C7—H7A | 109.6 | C17—C16—H16A | 108.2 |
N8—C7—H7A | 109.6 | O18—C17—O19 | 125.5 (2) |
C5—C7—H7B | 109.6 | O18—C17—C16 | 119.05 (17) |
N8—C7—H7B | 109.6 | O19—C17—C16 | 115.4 (2) |
H7A—C7—H7B | 108.1 | C16—C20—H20A | 109.5 |
C9—N8—C7 | 113.85 (18) | C16—C20—H20B | 109.5 |
C9—N8—H8A | 108.2 (16) | H20A—C20—H20B | 109.5 |
C7—N8—H8A | 106.1 (17) | C16—C20—H20C | 109.5 |
C9—N8—H8B | 108.7 (16) | H20A—C20—H20C | 109.5 |
C7—N8—H8B | 107.5 (16) | H20B—C20—H20C | 109.5 |
H8A—N8—H8B | 113 (3) | C22—C21—H21A | 109.5 |
N8—C9—C13 | 109.5 (2) | C22—C21—H21B | 109.5 |
N8—C9—C10 | 111.33 (15) | H21A—C21—H21B | 109.5 |
C13—C9—C10 | 110.46 (19) | C22—C21—H21C | 109.5 |
N8—C9—H9A | 108.5 | H21A—C21—H21C | 109.5 |
C13—C9—H9A | 108.5 | H21B—C21—H21C | 109.5 |
C10—C9—H9A | 108.5 | O24—C22—O23 | 123.0 (3) |
O12—C10—O11 | 127.25 (18) | O24—C22—C21 | 120.7 (3) |
O12—C10—C9 | 119.45 (19) | O23—C22—C21 | 116.3 (3) |
O11—C10—C9 | 113.26 (16) | C22—O23—H3 | 115.3 (17) |
C9—C13—H13A | 109.5 | H251—O25—H252 | 103 (3) |
| | | |
C5—N1—C2—N3 | 1.6 (3) | C7—N8—C9—C13 | 160.63 (19) |
C5—N1—C2—C6 | −176.5 (3) | C7—N8—C9—C10 | −76.9 (2) |
N1—C2—N3—C4 | −1.6 (3) | N8—C9—C10—O12 | −16.6 (3) |
C6—C2—N3—C4 | 176.5 (3) | C13—C9—C10—O12 | 105.3 (3) |
C2—N3—C4—C5 | 1.0 (3) | N8—C9—C10—O11 | 165.6 (2) |
C2—N3—C4—C14 | −177.6 (2) | C13—C9—C10—O11 | −72.5 (3) |
N3—C4—C5—N1 | 0.0 (3) | C5—C4—C14—N15 | −112.8 (3) |
C14—C4—C5—N1 | 178.4 (2) | N3—C4—C14—N15 | 65.5 (3) |
N3—C4—C5—C7 | −175.2 (2) | C4—C14—N15—C16 | 174.45 (17) |
C14—C4—C5—C7 | 3.2 (4) | C14—N15—C16—C20 | 75.4 (2) |
C2—N1—C5—C4 | −0.9 (3) | C14—N15—C16—C17 | −160.94 (16) |
C2—N1—C5—C7 | 174.9 (2) | N15—C16—C17—O18 | −14.6 (3) |
C4—C5—C7—N8 | 100.3 (3) | C20—C16—C17—O18 | 108.7 (2) |
N1—C5—C7—N8 | −74.3 (2) | N15—C16—C17—O19 | 166.56 (18) |
C5—C7—N8—C9 | −172.39 (14) | C20—C16—C17—O19 | −70.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O23—H3···N3 | 1.06 (3) | 1.51 (3) | 2.569 (3) | 177 (3) |
N8—H8A···O25 | 0.94 (3) | 1.90 (3) | 2.823 (2) | 170 (3) |
N15—H15A···O25 | 0.89 (3) | 1.97 (3) | 2.817 (2) | 159 (3) |
N15—H15B···O24 | 0.93 (3) | 1.90 (3) | 2.832 (3) | 174 (3) |
N1—H1···O11i | 0.90 (3) | 1.70 (3) | 2.585 (2) | 168 (4) |
N8—H8B···O12i | 0.99 (3) | 1.85 (3) | 2.815 (2) | 167 (3) |
O25—H251···O19ii | 0.87 (4) | 1.78 (4) | 2.636 (3) | 169 (3) |
O25—H252···O18iii | 0.85 (4) | 1.99 (4) | 2.838 (2) | 172 (3) |
O25—H252···O19iii | 0.85 (4) | 2.42 (4) | 3.027 (3) | 129 (3) |
Symmetry codes: (i) −x, y−1/2, −z+1; (ii) −x, y−1/2, −z; (iii) −x, y+1/2, −z. |
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