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In the title compound, C3H7NO2·NH4+·NO3-, the sarcosine zwitterions have an almost perfectly planar N-C-COO main chain and assemble in chains via hydrogen bonds. The ammonium and nitrate ions are arranged in sheets that alternate with sheets of sarcosine chains. The whole structure is stabilized by an extensive three-dimensional network of hydrogen bonds.
Supporting information
CCDC reference: 274391
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.041
- wR factor = 0.130
- Data-to-parameter ratio = 11.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged .... H1A
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged .... H1B
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged .... H2A
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged .... H2B
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged .... H3A
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged .... H3B
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged .... H3C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
10 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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
7 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: PLATON (Spek, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
'
N-methylglycine ammonium nitrate'
top
Crystal data top
C3H7NO2·H4N+·NO3− | F(000) = 360 |
Mr = 169.15 | Dx = 1.452 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71074 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 5.7208 (9) Å | θ = 6.6–17.3° |
b = 7.9144 (8) Å | µ = 0.14 mm−1 |
c = 17.447 (2) Å | T = 293 K |
β = 101.682 (13)° | Block, colourless |
V = 773.58 (17) Å3 | 0.43 × 0.40 × 0.39 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.037 |
Radiation source: fine-focus sealed tube | θmax = 25.5°, θmin = 2.8° |
Graphite monochromator | h = −6→6 |
profile data from ω–2θ scans | k = −9→9 |
2819 measured reflections | l = −21→6 |
1423 independent reflections | 3 standard reflections every 7200 min |
901 reflections with I > 2σ(I) | intensity decay: 0.3% |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0885P)2] where P = (Fo2 + 2Fc2)/3 |
1423 reflections | (Δ/σ)max < 0.001 |
121 parameters | Δρmax = 0.19 e Å−3 |
10 restraints | Δρmin = −0.26 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 | 0.9102 (3) | 0.23951 (19) | 0.13575 (9) | 0.0392 (4) | |
O2 | 0.7208 (3) | 0.1325 (2) | 0.02244 (9) | 0.0442 (5) | |
C1 | 0.7251 (4) | 0.1963 (2) | 0.08725 (13) | 0.0306 (5) | |
N1 | 0.2800 (3) | 0.1830 (2) | 0.05347 (10) | 0.0332 (5) | |
H1A | 0.154 (2) | 0.1719 (3) | 0.0763 (4) | 0.040* | |
H1B | 0.3046 (5) | 0.0830 (19) | 0.0326 (4) | 0.040* | |
C2 | 0.4902 (3) | 0.2253 (3) | 0.11365 (13) | 0.0325 (5) | |
H2A | 0.4887 (3) | 0.1597 (11) | 0.1582 (8) | 0.039* | |
H2B | 0.4808 (4) | 0.3387 (19) | 0.1277 (3) | 0.039* | |
C3 | 0.2213 (4) | 0.3082 (4) | −0.01002 (16) | 0.0563 (8) | |
H3A | 0.195 (4) | 0.418 (2) | 0.0119 (4) | 0.084* | |
H3B | 0.078 (3) | 0.2733 (14) | −0.0464 (9) | 0.084* | |
H3C | 0.353 (3) | 0.3163 (19) | −0.0374 (9) | 0.084* | |
N3 | 0.0319 (3) | 0.0545 (2) | 0.28475 (11) | 0.0389 (5) | |
H4 | 0.066 (4) | −0.055 (3) | 0.3039 (15) | 0.083 (10)* | |
H5 | −0.008 (5) | 0.051 (4) | 0.2295 (11) | 0.082 (10)* | |
H6 | −0.097 (5) | 0.098 (4) | 0.3025 (17) | 0.109 (14)* | |
H7 | 0.173 (4) | 0.118 (4) | 0.2998 (19) | 0.128 (16)* | |
O3 | 0.3624 (3) | 0.3477 (2) | 0.31995 (13) | 0.0661 (6) | |
O4 | 0.5828 (3) | 0.1282 (2) | 0.33614 (14) | 0.0686 (7) | |
O5 | 0.7443 (3) | 0.3697 (2) | 0.32930 (13) | 0.0610 (6) | |
N2 | 0.5642 (3) | 0.2840 (2) | 0.32817 (11) | 0.0399 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0262 (8) | 0.0469 (9) | 0.0442 (9) | −0.0024 (7) | 0.0066 (7) | −0.0111 (7) |
O2 | 0.0351 (9) | 0.0528 (10) | 0.0484 (10) | −0.0038 (7) | 0.0172 (7) | −0.0215 (8) |
C1 | 0.0315 (12) | 0.0232 (10) | 0.0389 (12) | −0.0003 (8) | 0.0113 (9) | −0.0040 (9) |
N1 | 0.0251 (9) | 0.0345 (9) | 0.0428 (11) | −0.0015 (7) | 0.0139 (8) | −0.0078 (8) |
C2 | 0.0294 (12) | 0.0322 (11) | 0.0378 (11) | −0.0012 (9) | 0.0116 (9) | −0.0058 (9) |
C3 | 0.0394 (15) | 0.0800 (19) | 0.0498 (15) | 0.0097 (13) | 0.0100 (11) | 0.0121 (14) |
N3 | 0.0380 (12) | 0.0382 (11) | 0.0406 (12) | 0.0023 (9) | 0.0079 (9) | 0.0023 (9) |
O3 | 0.0413 (11) | 0.0556 (11) | 0.1012 (16) | 0.0079 (9) | 0.0136 (10) | 0.0064 (11) |
O4 | 0.0630 (13) | 0.0314 (10) | 0.1206 (19) | 0.0006 (8) | 0.0406 (12) | −0.0009 (10) |
O5 | 0.0514 (12) | 0.0541 (11) | 0.0840 (14) | −0.0157 (9) | 0.0294 (10) | 0.0037 (10) |
N2 | 0.0408 (12) | 0.0384 (11) | 0.0440 (11) | −0.0015 (9) | 0.0166 (9) | 0.0009 (9) |
Geometric parameters (Å, º) top
O1—C1 | 1.261 (3) | C3—H3B | 0.9710 |
O2—C1 | 1.234 (3) | C3—H3C | 0.9710 |
C1—C2 | 1.524 (3) | N3—H4 | 0.94 (2) |
N1—C2 | 1.466 (3) | N3—H5 | 0.945 (19) |
N1—C3 | 1.474 (3) | N3—H6 | 0.92 (2) |
N1—H1A | 0.8942 | N3—H7 | 0.94 (2) |
N1—H1B | 0.8942 | O3—N2 | 1.241 (3) |
C2—H2A | 0.9351 | O4—N2 | 1.243 (3) |
C2—H2B | 0.9351 | O5—N2 | 1.231 (2) |
C3—H3A | 0.9710 | | |
| | | |
O2—C1—O1 | 125.72 (19) | N1—C3—H3A | 109.5 |
O2—C1—C2 | 118.90 (19) | N1—C3—H3B | 109.5 |
O1—C1—C2 | 115.37 (19) | H3A—C3—H3B | 109.5 |
C2—N1—C3 | 114.45 (19) | N1—C3—H3C | 109.5 |
C2—N1—H1A | 108.6 | H3A—C3—H3C | 109.5 |
C3—N1—H1A | 108.6 | H3B—C3—H3C | 109.5 |
C2—N1—H1B | 108.6 | H4—N3—H5 | 108.8 (19) |
C3—N1—H1B | 108.6 | H4—N3—H6 | 110.5 (19) |
H1A—N1—H1B | 107.6 | H5—N3—H6 | 108.1 (19) |
N1—C2—C1 | 113.26 (18) | H4—N3—H7 | 106.9 (18) |
N1—C2—H2A | 108.9 | H5—N3—H7 | 109 (2) |
C1—C2—H2A | 108.9 | H6—N3—H7 | 114 (2) |
N1—C2—H2B | 108.9 | O5—N2—O3 | 122.30 (19) |
C1—C2—H2B | 108.9 | O5—N2—O4 | 119.5 (2) |
H2A—C2—H2B | 107.7 | O3—N2—O4 | 118.2 (2) |
| | | |
C3—N1—C2—C1 | −75.5 (2) | O1—C1—C2—N1 | 176.4 (2) |
O2—C1—C2—N1 | −4.4 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.89 | 1.97 | 2.822 (2) | 158 |
N1—H1A···O2i | 0.89 | 2.49 | 3.160 (2) | 132 |
N1—H1B···O2ii | 0.89 | 1.95 | 2.826 (2) | 167 |
N3—H4···O1iii | 0.94 (2) | 1.92 (2) | 2.839 (2) | 164 (2) |
N3—H5···O1i | 0.95 (2) | 2.20 (2) | 2.942 (2) | 135 (2) |
N3—H5···O5iii | 0.95 (2) | 2.45 (3) | 2.961 (3) | 114 (2) |
N3—H5···O3iv | 0.95 (2) | 2.59 (3) | 3.072 (3) | 112 (2) |
N3—H6···O4i | 0.92 (2) | 2.05 (2) | 2.946 (3) | 164 (3) |
N3—H6···O5i | 0.92 (2) | 2.42 (3) | 3.171 (3) | 139 (3) |
N3—H6···N2i | 0.92 (2) | 2.55 (2) | 3.443 (3) | 164 (3) |
N3—H7···O3 | 0.94 (2) | 2.11 (2) | 2.977 (3) | 153 (3) |
N3—H7···O4 | 0.94 (2) | 2.31 (2) | 3.151 (3) | 149 (3) |
N3—H7···N2 | 0.94 (2) | 2.56 (2) | 3.494 (3) | 175 (3) |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z; (iii) −x+1, y−1/2, −z+1/2; (iv) −x, y−1/2, −z+1/2. |
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